SUBSTITUTED UREAS

UREES SUBSTITUEES

English Abstract

The invention relates to substituted ureas of general formula (Ia) and (Ib),
wherein variables X, Z, m, R and RA have the meaning cited in claim 1 and Q
represents one of radicals Q1 to Q6: (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6),
wherein R3, R4, R5, R6, R7, R8, R9, Y, Y', T and U have the meaning cited in
claim 1. The invention also relates to the utilization of the inventive
compounds as herbicides, to agents containing said inventive compounds and to
methods for controlling harmful plants.

French Abstract

L'invention concerne des urées substituées de formules générales (Ia) et (Ib) dans lesquelles les variables X, Z, m, R et R?A¿ ont la signification indiquée dans la revendication 1, et Q représente un des groupes Q1 à Q6: (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6) où R?3¿, R?4¿, R?5¿, R?6¿, R?7¿, R?8¿, R?9¿, Y, Y', T et U ont la signification indiquée dans la revendication 1. L'invention concerne également l'utilisation desdits composés comme herbicides, ainsi que des agents contenant lesdits composés, et des procédés pour lutter contre les plantes nuisibles.

Claims

167
we claim:-
1. A substituted urea of the formula Ia or Ib
<IMG>
in which the variables X, Z, m, R and R A are as defined
below:
X is S or O;
Z is O, S, S=O or SO2;
m has the value 0, 1, 2 or 3;
R is C(O)OR10, C(O)SR10, C(S)OR10, C(S)SR10, CO2H, CHO,
cyano, C(O)NR11R12, C(S)NR11R12, C(O)NHC(O)C1,
C(O)NHS(O)2C1, C(O)NHC(O)OR12', C(O)NHS(O)2R12',
C(O)NHS(O)2OR12', C(O)R2, P(O)R1(OR1), P(O)(OR1)2, S(O)n R2
where n = 0, 1 or 2, or SO2NHR1;
R A is hydroxyl, CO2R1, halogen, cyano, C(O)N(R1)2, where the
radicals R1 are, if appropriate, different from one
another, is OR2, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-alkenyl, C3-C6-alkynyl, COR1, S(O)n R1 where n = 0, 1
or 2, or is C(O)SR1;
and in which
Q is one of the radicals Q1 to Q6:
<IMG>

168
<IMG>
in which
Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O, S, SO or SO2;
and the radicals R1 to R30 are as defined below:
R1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl or C3-C6=alkynyl;
R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl,
hydroxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkylthio-C1-C6-alkyl,
C1-C6-alkylsulfinyl-C1-C6-alkyl,
C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-cycloalkyl,
C3-C6-cycloalkyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl,
C3-C6-cycloalkoxy-C1-C6-alkyl,
C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl,
C1-C6-haloalkoxy-C1-C6-alkyl,
C3-C6-haloalkenyloxy-C1-C6-alkyl,
C3-C6-haloalkynyloxy-C1-C6-alkyl,
C3-C6-cycloalkyl-C1-C6-thioalkyl,
C3-C6-alkenylthio-C1-C6-alkyl,
C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
C3-C6-halocycloalkyl-C1-C6-alkyl, halo-C2-C6-alkenyl,
C1-C6-alkoxy-C3-C6-alkenyl,
C1-C6-haloalkoxy-C3-C6-alkenyl,
C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl,
C1-C6-alkoxy-C3-C6-alkynyl,

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C1-C6-haloalkoxy-C3-C6-alkynyl,
C1-C6-alkylthio-C3-C6-alkynyl, C1-C6-alkylcarbonyl,
CHR1COR7, CHR1P(O)(OR7)2, P(O)(OR7)2, CHR1P(S)(OR7)2,
CHR1C(O)NR11R12, CHR1C(O)NH2, phenoxy-C1-C6-alkyl or
benzyloxy-C1-C6-alkyl, where the benzene rings of the two
last-mentioned groups may for their part be substituted
by halogen, C1-C4-alkyl or C1-C4-haloalkyl; is benzyl
which may be substituted by halogen, C1-C4-alkyl or
C1-C4-haloalkyl or is phenyl or pyridyl, each of which
may be substituted by halogen, C1-C4-alkyl,
C1-C4-haloalkyl or C1-C4-alkoxy;
R3 is hydrogen or halogen;
R4 is C1-C6-alkyl, C1-C6-haloalkyl, OCH3, SCH3, OCHF2,
halogen, cyano or NO2;
R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen,
C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio,
C1-C6-alkoxy-(C1-C6-alkyl)carbonyl,
C1-C6-alkylthio-(C1-C6-alkyl)carbonyl,
(C1-C6-alkyl)iminooxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxyamino-C1-C6-alkyl,
C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl,
is C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy,
C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio,
C2-C6-alkynyloxy, C2-C6-alkynylthio,
(C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio,
(C1-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy,
(C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy,
(C2-C6-alkynyl)carbonylthio, C1-C6-alkylsulfonyloxy or
C1-C6-alkylsulfonyl, where each of the 17 last-mentioned
radicals may, if desired, carry one, two or three
substituents selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl,
C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy,
C1-C6-alkylthio, C1-C6-alkylsulfinyl,
C1-C6-alkylsulfonyl, C1-C6-alkylideneaminooxy, oxo,
=N-OR13;
- phenyl, phenoxy or phenylsulfonyl, where the three
last-mentioned groups may carry one, two or three
substituents selected from the group consisting of

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halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
- -CO-R14. -CO-OR14, -CO-SR14, -CO-N(R14)-R15, -OCO-R14,
-OCO-OR14', -OCO-SR14', -OCO-N(R14)-R15, -N(R14)-R15,
and -C(R16)=N-OR13;
is C(Z1)-R17, -C(=NR18)R17, C(R17)(Z2R19)(Z3R20),
C(R17)=C(R21)-CN, C(R17)=C(R21)-CO-R22,
-CH(R17)-CH(R21)-COR22, -C(R17)=C(R21)-CH2-CO-R22,
-C(R17)=C(R21)-C(R23)=C(R24)-CO-R22,
-C(R17)=C(R21)-CH2-CH(R25)-CO-R22, -CO-OR26, -CO-SR26,
-CON(R26)-OR13, -CSC-CO-NHOR13, -CSC-CO-N(R26)-OR13,
-C=C-CS-NH-OR13, -C=C-CS-N(R26)-OR13,
-C(R17)=C(R21)-CO-NHOR13, -C(R17)=C(R21)-CO-N(R26)-OR13,
-C(R17)=C(R21)-CS-NHOR13, -C(R17)=C(R21)-CS-N(R26)-OR13,
-C(R17)=C(R21)-C(R16)=N-OR13, C(R16)=N-OR13,
-CwC-C(R16)=NOR13, C(Z2R19)(Z3R20)-OR26,
-C(Z2R19)(Z2R20)SR26, C(Z2R19)(Z3R20)-N(R27)R28, -N(R27)-R28,
-CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; where Z1, Z2,
Z3 independently of one another are oxygen or sulfur;
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl,
C1-C3-alkoxy-C3-C6-alkenyl, C3-C6-haloalkenyl,
C3-C6-alkynyl, C1-C3-alkoxy-C3-C6-alkynyl,
C3-C6-haloalkynyl, C3-C7-cycloalkyl, 3- to 7-membered
saturated heterocyclyl, where each cycloalkyl and each
heterocyclyl ring may contain a carbonyl or thiocarbonyl
ring member where each cycloalkyl and heterocyclyl ring
may be unsubstituted or may carry one, two, three or four
substitutents, selected from the group consisting of
cyano, nitro, amino, hydroxyl, halogen, C1-C4-alkyl,
C1-C4-haloalkyl, C1-C4-cyanoalkyl, C1-C4-hydroxyalkyl,
C1-C4-aminoalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy,
C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl,
C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl,
(C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)carbonyl,
(C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy,
(C1-C4-haloalkyl)carbonyloxy, di(C1-C4-alkyl)amino,
C3-C6-alkenyl, C3-C6-alkynyl, C3-C4-alkenyloxy,
C3-C4-alkenylthio, C3-C4-alkynyloxy and C3-C4-alkynylthio;
R7 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C3-alkoxy-C1-C3-alkyl, C2-C6-cyanoalkyl, C3-C6-alkenyl,
C3-C6-alkynyl;

171
R8 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl or halogen;
R9 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl; or
R8 and R9 together are C=O;
R10 is C1-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl,
C3-C10-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkylthio-C1-C6-alkyl,
C1-C6-alkylsulfinyl-C1-C6-alkyl,
C1-C6-alkylsulfonyl-C1-C6-alkyl,
C1-C3-alkoxy-C1-C3-alkoxy-C1-C3-alkyl,
C3-C6-cycloalkyl-C1-C6-alkyl, carboxyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C2-C6-alkenyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl,
C3-C8-cycloalkoxy-C1-C6-alkyl,
C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl,
C1-C6-haloalkoxy-C1-C6-alkyl,
C3-C6-haloalkenyloxy-C1-C6-alkyl,
C3-C6-haloalkynyloxy-C1-C6-alkyl,
C3-C6-cycloalkyl-C1-C6-thioalkyl,
C3-C6-alkenylthio-C1-C6-alkyl,
C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
C3-C6-halocyclo-C1-C6-alkyl, halo-C3-C6-alkenyl,
C1-C6-alkoxy-C3-C6-alkenyl,
C1-C6-haloalkoxy-C3-C6-alkenyl,
C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl,
C1-C6-alkoxy-C3-C6-alkynyl,
C1-C6-haloalkoxy-C3-C6-alkynyl,
C1-C6-alkylthio-C3-C6-alkynyl, CHR1COR7, CHR1P(O)(OR7)2,
P(O)(OR7)2, CHR1P(S)(OR7)2, CHR1C(O)NR11R12, CHR1C(O)NH2,
C1-C6-alkyl, which is substituted by phenoxy or
benzyloxy, where the benzene rings of the two
last-mentioned groups may for their part be substituted
by halogen, C1-C4-alkyl or C1-C4-haloalkyl;
is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl,
quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl,
2-methylindazolyl, benzofuranyl, benzothienyl,
benzoxazolyl, benzthiazolyl, benzyl, which may carry a
divalent substituent, such as methylenedioxy,
difluoromethylenedioxy, chlorofluoromethylenedioxy,
dichloromethylenedioxy, in adjacent positions or which
may in each case be mono- to pentasubstituted by halogen,

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C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio,
amino, C1-C4-monoalkylamino, C1-C4-dialkylamino,
C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl,
C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or
cyano;
R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C2-C6-alkenyl, where the alkenyl
chain may additionally carry one to three halogen and/or
cyano radicals, are phenyl or benzyl which may carry a
divalent substituent, such as methylenedioxy,
difluoromethylenedioxy, chlorofluoromethylenedioxy,
dichloromethylenedioxy, in adjacent positions or which
may be mono- to pentasubstituted by halogen, C1-C4-alkyl,
C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy,
C1-C4-alkylthio, C1-C4-haloalkylthio, amino,
C1-C4-monoalkylamino, C1-C4-dialkylamino,
C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl,
C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano
or
R11 and R12 together with the common nitrogen atom are a
saturated or unsaturated 4- to 7-membered azaheterocycle
which, in addition to carbon ring members, may, if
desired, contain one of the following members: -O-, -S-,
-N=, -NH- or N-(C1-C6-alkyl)-;
R12' is as defined for R12, but excluding hydrogen;
R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,.
hydroxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C2-C6-alkenyl,
(C1-C6-alkyl)carbonyloxy-C1-C6-alkyl or
phenyl-C1-C6-alkyl, in which the phenyl ring may, if
desired, carry one, two or three substituents selected
from the group consisting of cyano, nitro, halogen,

173
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
R14 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C3-C6-alkenyloxy)carbonyl-C1-C6-alkyl, phenyl or
phenyl-C1-C6-alkyl, where the phenyl ring of the two
last-mentioned groups may be unsubstituted or may carry
one, two or three radicals selected from the group
consisting of halogen, nitro, cyano, C1-C6-alkyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl;
R14' is as defined for R14, but excluding hydrogen;
R15 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-cycloalkyl,
C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy,
C3-C6-alkenyl or C3-C6-alkenyloxy;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio,
(C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy,
C1-C6-alkylsulfonyloxy or C1-C6-haloalkylsulfonyloxy,
where the 12 last-mentioned radicals may carry one of the
following substituents: hydroxyl, cyano, hydroxycarbonyl,
C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl,
di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkyl)carbonyloxy,
C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl;
is (C1-C6-alkyl)carbonyl, (C1-C6-haloalkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyloxy,
(C1-C6-alkyl)carbonylthio, (C1-C6-haloalkyl)carbonylthio,
(C1-C6-alkoxy)carbonylthio, C2-C6-alkenyl,
(C2-C6-alkenyl)carbonyloxy, C2-C6-alkenylthio,
C3-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-alkynylthio,
(C2-C6-alkynyl)carbonyloxy, C3-C6-alkynylsulfonyloxy,
C3-C6-cycloalkyl, C3-C6-cycloalkyloxy,
C3-C6-cycloalkylthio, (C3-C6-cycloalkyl)carbonyloxy,
C3-C6-cycloalkylsulfonyloxy;
is phenyl, phenoxy, phenylthio, benzoyloxy,
phenylsulfonyloxy, phenyl-C1-C6-alkyl,
phenyl-C1-C6-alkoxy, phenyl-C1-C6-alkylthio,
phenyl-(C1-C6-alkyl)carbonyloxy or
phenyl-(C1-C6-alkyl)sulfonyloxy, where the phenyl rings

174
of the 10 last-mentioned radicals may be unsubstituted or
may for their part carry one to three substituents, in
each case selected from the group consisting of cyano,
nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy
and (C1-C6-alkoxy)carbonyl;
R17 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R18 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C3-C6-cycloalkoxy,
C5-C7-cycloalkenyloxy, C1-C6-haloalkoxy,
C3-C6-haloalkenyloxy, hydroxy-C1-C6-alkoxy,
cyano-C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-alkoxy,
C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxy-C3-C6-alkenyloxy,
(C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy,
(C1-C6-alkyl)carbamoyloxy, (C1-C6-haloalkyl)carbamoyloxy,
(C1-C6-alkyl)carbonyl-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl-C1-C6-alkoxy,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkoxy,
C1-C6-alkylthio-C1-C6-alkoxy,
di(C1-C6-alkyl)amino-C1-C6-alkoxy, -N(R29)R30, phenyl
which for its part may carry one, two or three
substituents, in each case selected from the group
consisting of cyano, nitro, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
is phenyl-C1-C6-alkoxy, phenyl-(C1-C6-alkyl),
phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where
in each case one or two methylene groups of the carbon
chains in the four last-mentioned groups may be replaced
by -O-, -S- or -N(C1-C6-alkyl)- and where the phenyl
rings in the four last-mentioned groups may be
unsubstituted or may for their part carry one to three
substituents, selected from the group consisting of
cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
is C3-C7-heterocyclyl, C3-C7-heterocyclyl-C1-C6-alkyl,
C3-C7-heterocyclyl-C1-C6-alkoxy,
C3-C7-heterocyclyl-C3-C6-alkenyloxy or
C3-C7-heterocyclyl-C3-C6-alkynyloxy, where in each case

175
one or two methylene groups of the carbon chains in the
four last-mentioned groups may be replaced by -O-, -S- or
-N(C1-C6-alkyl)- and where each heterocycle may be
saturated, unsaturated or aromatic and is either
unsubstituted or for its part carries one to three
substituents, selected from the group consisting of
cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R19, R20 independently of one another are C1-C6-alkyl,
C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl or together are a saturated or
unsaturated 2- to 4-membered carbon chain which may carry
an oxo substituent, where a member of this chain which is
not adjacent to the variables Z2 and Z3 may be replaced
by -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)- and where the
carbon chain may carry one to three substituents selected
from the group consisting of cyano, nitro, amino,
halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy,
C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkyl,
cyano-C1-C6-alkyl, hydroxy-C1-C6-alkyl,
C1-C6-alkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl,
C3-C6-cycloalkoxy, carboxyl, (C1-C6-alkoxy)carbonyl,
(C1-C6-alkyl)carbonyloxy-C1-C6-alkyl and phenyl;
are unsubstituted or substituted phenyl where the carbon
chain may also be substituted by a fused-on or
spiro-linked 3- to 7-membered ring which may contain, as
ring members, one or two heteroatoms selected from the
group consisting of oxygen, sulfur, nitrogen and
C1-C6-alkyl-substituted nitrogen and which may for its
part, if desired, carry one or two of the following
substituents: cyano, C1-C6-alkyl, C2-C6-alkenyl,
C1-C6-alkoxy, cyano-C1-C6-alkyl, C1-C6-haloalkyl and
(C1-C6-alkoxy)carbonyl;
R21 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;
R22 is hydrogen, O-R31, S-R31, C1-C6-alkyl which may carry one
or two C1-C6-alkoxy substituents, is C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl,
C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyliminooxy,
-N(R27)R28 or phenyl which may be unsubstituted or may
carry one to three substituents, in each case selected

176
from the group consisting of cyano, nitro, halogen,
C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-alkoxy
and (C1-C6-alkoxy)carbonyl;
R23 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, -N(R27)R28
or phenyl which for its part may carry one to three
substituents selected from the group consisting of cyano,
nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy,
C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;
R25 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R26, R31 independently of one another are hydrogen,
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or
C2-C6-alkynyl, where the 4 last-mentioned groups may in
each case carry one or two of the following radicals:
cyano, halogen, hydroxyl, hydroxycarbonyl, C1-C6-alkoxy,
C1-C6-alkylthio, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyloxy,
(C3-C6-alkenyloxy)carbonyl;
are (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl,
C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl,
C1-C6-alkyloximino-C1-C6-alkyl, C3-C6-cycloalkyl;
are phenyl or phenyl-C1-C6-alkyl, where the phenyl rings
may be unsubstituted or may for their part carry one to
three substituents, in each case selected from the group
consisting of cyano, nitro, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R27, R28, R29, R30 independently of one another are hydrogen,
C1-C6-alkyl, C3-C6-alkenyl, C2-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
are (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the
alkenyl chain may additionally carry one to three halogen
and/or cyano radicals, are C1-C6-alkylsulfonyl,

177
(C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl, phenyl or
phenylsulfonyl, where the phenyl rings of the two
last-mentioned radicals may be unsubstituted or may for
their part carry one to three substituents, in each case
selected from the group consisting of cyano, nitro,
halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl; or
R27 and R28 and/or
R29 and R30 together with the respective common nitrogen atom
are a saturated or unsaturated 4- to 7-membered
azaheterocycle which, in addition to carbon ring members,
may, if desired, contain one of the following members:
-O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)-;
and the agriculturally useful salts of the compounds of the
formulae Ia and Ib.
2. A compound of the formula Ia or Ib as claimed in claim 1
where the variables are as defined below:
Z is O or S
R A is CO2R1, halogen, cyano, OR2 or C1-C3-alkyl;
m is 0, 1, 2 or 3;
Q is Q1, Q2 or Q4;
x, Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O or S;
R is C(O)OR10, C(O)SR10, C(S)OR10, C(S)SR10, CHO, CN, C(O)R2,
C(O)NR11R12, C(S)NR11R12, C(O)NHC(O)OR12', C(O)NHS(O)2R12',
C(O)NHS(O)2OR12';
R1 is hydrogen or C1-C3-alkyl;
R2 is C1-C3-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C3-haloalkyl,
C1-C3-alkoxycarbonyl-C1-C3-alkyl, cyano-C1-C3-alkyl,
benzyl, which may be substituted by halogen, C1-C4-alkyl
or trifluoromethyl, or

178
is phenyl, which may be substituted by halogen,
C1-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
R3 is hydrogen, fluorine or chlorine;
R4 is chlorine, trifluoromethyl or cyano;
R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy,
C1-C6-haloalkylthio, C1-C6-alkoxy-(C1-C6-alkyl)carbonyl,
C1-C6-alkylthio-(C1-C6-alkyl)carbonyl,
(C1-C6-alkyl)iminooxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxyamino-C1-C6-alkyl,
C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl,
is C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy,
C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio,
C2-C6-alkynyloxy, C2-C6-alkynylthio,
(C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio,
(C1-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy,
(C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy,
(C2-C6-alkynyl)carbonylthio, C1-C6-alkylsulfonyloxy or
C1-C6-alkylsulfonyl, where each of these 17 radicals may,
if desired, carry one, two or three substituents,
selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl,
C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy,
C1-C6-alkylthio, C1-C6-alkylsulfinyl,
C1-C6-alkylsuifonyl, C1-C6-alkylideneaminooxy, oxo,
=N-OR13
- phenyl, phenoxy or phenylsulfonyl, where the three
last-mentioned substituents may for their part carry
one, two or three substituents, in each case selected
from the group consisting of halogen, nitro, cyano,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
- -CO-R14, -CO-OR14, -CO-SR14, -CO-N(R14)-R15, -OCO-R14,
-OCO-OR14', -OCO-SR14', -OCO-N(R14)-R15, -N(R14)-R15,
and -C(R16)=N-OR13;

179
is C(Z1)-R17, -C(=NR18)R17, C(R17)(Z2R19)(Z3R20),
C(R17)=C(R21)-CN, C(R17)=C(R21)-CO-R22,
-CH(R17)-CH(R21)-COR22, -C(R17)=C(R21)-CH2-CO-R22,
-C(R17)=C(R21)-C(R23)=C(R24)-CO-R22,
-C(R17)=C(R21)-CH2-CH(R25)-CO-R22, -CO-OR26, -CO-SR26,
-CON(R26)-OR13, -C=C-CO-NHOR13, -C=C-CO-N(R26)-OR13,
-C=C-CS-NH-OR13, -C=C-CS-N(R26)-OR13,
-C(R17)=C(R21)-CO-NHOR13, -C(R17)=C(R21)-CO-N(R26)-OR13,
-C(R17)=C(R21)-CS-NHOR13, -C(R17)=C(R21)-CS-N(R26)-OR13,
-C(R17)=C(R21)-C(R16)=N-OR13, C(R16)=N-OR13,
-C=C-C(R16)=NOR13, C(Z2R19)(Z3R20)-OR26,
-C(Z2R19)(Z2R20)SR26, C(Z2R19)(Z3R20)-N(R27)R28, -N(R27)-R28,
-CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; in which Z1,
Z2, Z3 independently of one another are oxygen or sulfur;
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C3-C7-cycloalkyl, or is 3- to 7-membered
saturated heterocyclyl which contains one or more oxygen
and/or sulfur atoms;
R7 is hydrogen or C1-C6-alkyl;
R8 is hydrogen or C1-C3-alkyl;
R9 is hydrogen, C1-C3-alkyl
R8 and R9 together are C=O;
R10 is C1-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl,
C3-C10-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl, cyano-C1-C6-alkyl,
is phenyl or benzyl which may in each case be mono- to
pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl,
C1-C4-alkoxy, C1-C4-haloalkoxy, amino,
C2-C4-monoalkylamino, C1-C4-dialkylamino,
C1-C4-alkoxycarbonyl, nitro or cyano;
R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, phenyl or
benzyl which may be mono- to pentasubstituted by halogen,
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,

180
C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;
or
R12 is as defined for R12, but excluding hydrogen;
R11 and R12 together with the common nitrogen atom are a
saturated or unsaturated 4- to 7-membered azaheterocycle;
R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl, cyano-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl or phenylalkyl, where
the phenyl ring may be mono- to trisubstituted by
halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or
C1-C3-alkoxy;
R14 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
is phenyl or benzyl which may be unsubstituted on the
phenyl ring or may be mono- to trisubstituted by halogen,
cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or
C1-C3-alkoxy;
R14' is as defined for R14, but excluding hydrogen;
R15 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy,
(C1-C3-alkoxy)carbonyl-C1-C3-alkoxy, C3-C6-alkenyl or
C3-C6-alkynyl;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, C3-C6-alkenyloxy,
(C1-C6-alkoxy)carbonylalkoxy, C2-C6-alkenyl,
(C2-C6-alkenyl)carbonyloxy, C3-C6-alkynyl,
(C2-C6-alkynyl)carbonyloxy,
is phenyl, phenoxy or benzyl, where the phenyl rings of
the 3 last-mentioned radicals may be unsubstituted or
mono- to trisubstituted by halogen, cyano, nitro,
C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or
(C1-C3-alkoxy)carbonyl;

181
R17 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or
(C1-C6-alkoxy)carbonyl;
R18 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
is phenyl or phenyl-(C1-C6-alkyl), where the two
last-mentioned phenyl radicals may be substituted by
halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl,
C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;
R19, R20 independently of one another are C1-C6-alkyl,
C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl, or
R19 and R20 together are a saturated 2- to 4-membered carbon
chain which may carry an oxo substituent, where a carbon
atom of this chain which is not adjacent to the variables
Z2 and Z3 may be replaced by -O-, -S-, -N=, -NH- or
-N(C1-C6-alkyl)- and where the carbon chain may be
substituted once to three times by halogen or
C1-C6-alkyl;
R21 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl
or C1-C6-alkoxy;
R22 is hydrogen, OR31, S-R31, C1-C6-alkyl, which may carry one
or two C1-C6-alkoxy substituents, is C2-C6-alkenyl,
C2-C6-alkynyl, C1-C6-haloalkyl or C3-C6-cycloalkyl;
R23 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl;
R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy or
C1-C6-haloalkyl;
R25 is hydrogen, cyano or C2-C6-alkyl;
R26, R31 independently of one another axe hydrogen,
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or
C2-C6-alkynyl, where the 4 last-mentioned groups may in
each case carry one or two of the following radicals:
cyano, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyl,
(C1-C6-alkoxy)carbonyl;

182
or are (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl,
phenyl or phenyl-C1-C6-alkyl;
R27, R28, R29, R30 independently of one another are hydrogen,
C1-C6-alkyl, C3-C6-alkenyl, C2-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl,
(Cl-C6-alkoxy)carbonyl, or
R27 and R28 and/or R29 and R30 together with the respective
common nitrogen atom are a saturated or unsaturated 4- to
7-membered azaheterocycle which, in addition to carbon
ring members, may, if desired, contain an oxygen atom or
an -NH- group.
3. A compound of the formula Ia or Ib as claimed in claim 1 or 2
in which Q is Q1 and
R5 is C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy,
where each of the 3 last-mentioned radicals may, if
desired, carry one to three substituents, in each case
selected from the group consisting of halogen,
C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy,
C1-C6-alkylsulfonyl, -CO-R14, -CO-OR14, -CO-N(R14)-R15,
-N(R14)-R15 and -C(R16)=N-OR13;
is -CO-R17, -C(NR18)-R17, -C(R17)(OR19)(OR20),
-C(R17)=C(R21)-CO-R22, -CH(R17)-CH(R21)-CO-R22, -CO-OR26,
-CO-N(R26)-OR13, -C(R17)=C(R21)-CO-N(R26)-OR13,
-C(R16)=N-OR13, -C(OR19)(OR20)-OR26, -N(R27)R28, -CON(R27)R28
or -C(R17)=C(R27)CO-N(R27)R28;
in which R13 to R22 and R26 to R28 are as defined above.
4. A compound of the formula Ia or Ib as claimed in any of the
preceding claims in which
R is C1-C6-alkyloxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, -C(O)NR11R12,
-C(O)NHC(O)Cl, -C(O)NHS(O)2Cl, C(O)NHC(O)OR12',
C(O)NHS(O)2R12', C(O)R2, P(O)R1(OR1), P(O)(OR1)2; S(O)R2,
S(O)2R2 or S(O)2NHR2
in which the variables R1, R2, R11, R12 and R12' are as
defined below:

183
R1 is C1-C6-alkyl
R2 is C1-C6-alkyl
R11 is hydrogen or C1-C6-alkyl
R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and
R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S,
X is O or S, and
m has the value 0.
5. A compound as claimed in claim 4 in which Q is Q1,
R3 is hydrogen or halogen
R4 is hydrogen, halogen or cyano,
and
R5 is C1-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl,
C3-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, haloalkenyloxy, alkenylthio,
haloalkenylthio, C1-C6-alkoxycarbonyl-C1-C6-alkoxy,
C3-C6-alkenyloxycarbonyl-C1-C6-alkoxy,
C3-C6-alkynyloxycarbonyl-C1-C6-alkoxy,
C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkoxy,
(C3-C6-alkenyloxy)carbonyl-C1-C6-alkoxycarbonyl-C1-C4-
alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkylthio,
C1-C6-alkenyloxycarbonyl-C1-C6-alkylthio,
C1-C6-alkynyloxycarbonyl-C1-C6-alkylthio,
C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkylthio,
C1-C6-alkoxyamino-C1-C6-alkyl,
N-C1-C6-alkoxy-N-(C1-C6-alkyl)amino-C1-C6-alkyl,
C1-C6-alkylsulfonylamino, -COOR26, -CONR27R28,
-C(=NR18)R17, -C(R16)=NOR13, C(R17)=C(R21)-CO-R22,
where the variables R13, R16, R17, R21, R22, R26 to R28 are as
defined below:

184
R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-haloalkeryl, C3-C6-alkynyl, C1-C6-cyanoalkyl or
C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R16 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkoxy or
phenoxycarbonyl-C1-C6-alkoxy;
R17 is hydrogen, C1-C6-alkyl;
R21 is hydrogen, halogen, C1-C6-alkyl;
R22 is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio,
C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R27 is hydrogen, C1-C6-alkyl;
R28 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
or R27 and R28 together are a 6-membered saturated
azaheterocycle which may have one or two not adjacent
oxygen atoms in the ring.
6. A compound of the formula Ia or Ib as claimed in claim 4 in
which
Q is Q2 or Q3, where
R3 is hydrogen or halogen,
R4 is hydrogen or halogen,
Y is O or S,
U is a single bond, oxygen or C1-C4-alkylene, and
R6 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C7-cycloalkyl, saturated C3-C7-heterocyclyl which has
one or two heteroatoms selected from the group consisting
of oxygen and sulfur in the ring, is C1-C6-alkoxyalkyl,
cyano-C1-C6-alkyl, CO2H, C1-C6-alkoxycarbonyl,

185
C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl.
7. A compound of the formula Ia or Ib as claimed in claim 4 in
which
Q is Q4 or Q5, in which
R3 is hydrogen or halogen
Y is O or S
Y' in the formula Q5 is oxygen or sulfur
T is a single bond, oxygen or C1-C4-alkylene and
R7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C7-cycloalkyl, saturated C3-C7-heterocyclyl which has
one or two heteroatoms selected from the group consisting
of oxygen and sulfur in the ring, is C1-C6-alkoxyalkyl,
cyano-C1-C6-alkyl, CO2H, C1-C6-alkoxycarbonyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl.
8. A compound of the formula Ia or Ib as claimed in claim 4 in
which
Q is Q6
R3 is hydrogen or halogen
R4 is hydrogen or halogen
R8 and R9 independently of one another are hydrogen,
C1-C6-alkyl, halogen, cycloalkyl or C1-C6-haloalkyl, or
R8 and R9 together with the carbon atom to which they are
attached are a carbonyl group.
9. A compound of the formula Ia or Ib as claimed in any of the
preceding claims in which
Q is Q1,
Z is oxygen,

186
X is oxygen or sulfur,
m has the value 0,
R is C1-C4-alkoxycarbonyl or
(C1-C4-alkoxycarbonyl)iminocarbonyl,
R3 is fluorine, chlorine or hydrogen,
R4 is halogen, and
R5 is CN, COOH, C1-C4-alkoxyiminomethyl, C1-C4-alkoxy,
C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy,
C3-C6-alkenyloxyiminomethyl,
(C1-C4-alkoxycarbonyl)-C2-C6-alkenyloxy,
C3-C6-alkynyloxyiminomethyl,
2-[C1-C4-alkoxycarbonyl]-2-chloroethyl,
2-[C1-C4-alkoxycarbonyl]-2-chloroethenyl,
C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy,
(C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl,
is COOR26 where R26 = C1-C4-alkoxy-C1-C4-alkyl or
C3-C6-alkenyloxycarbonyl-C1-C4-alkyl,
is CONR27R28 where R27 = hydrogen or C1-C4-alkyl and R28 =
hydrogen, C1-C4-alkyl or C1-C4-alkoxy,
is C(=NR17)R18 in which R17 is C1-C4-alkoxy and R18 is
C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.
10. A composition comprising at least one substituted urea of the
formula Ia or Ib in which the variables are as defined in any
of claims 1 to 9 or an agriculturally useful salt of Ia or Ib
and customary auxiliaries.
11. A method for controlling undesirable vegetation, which
comprises allowing a herbicidally effective amount of at
least one substituted urea of the formula Ia or Ib in which
the variables are as defined in any of claims 1 to 9 or an
agriculturally useful salt of Ia or Ib to act on plants,
their habitat and/or on seed.
12. The use of substituted ureas of the formula Ia or Ib in which
the variables are as defined in any of claims 1 to 9 or their
agriculturally useful salts as herbicides.

187
13. A compound of the general formula Ia or Ib as claimed in
claim 1, in which Q is Q1,
R is C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)imino-
carbonyl,
Z is O and
X is O or S,
m has the value 0,
R3 is fluorine or chlorine,
R4 is halogen, and
R5 is C1-C4-alkoxyiminomethyl, C1-C4-alkoxy, C3-C6-cyclo-
alkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-
alkenyloxyiminomethyl, (C1-C4-alkoxycarbonyl)-C2-C6-
alkenyloxy, C3-C6-alkynyloxyiminomethyl, 2-[C1-C4-alkoxy-
carbonyl]-2-chloroethyl, 2-[C1-C4-alkoxycarbonyl]-2-
chloroethenyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy,
(C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl.
14. A compound of the formula Ia or Ib as claimed in claim 1, in
which
R is C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)imino-
carbonyl,
Z is O and
X is O or S,
m has the value 0 and
Q is Q4, in which
R3 is halogen and
Y is O,
T is a single bond and
R7 is C3-C6-alkynyl.

188
15. A method for controlling undesirable vegetation, which
comprises allowing a herbicidally effective amount of at
least one substituted urea of the general formula Ia or Ib,
in which the variables are as defined in any of claims 13 or
14, or an agriculturally useful salt of Ia or Ib, to act on
plants, their habitat and/or seeds.
16. The use of substituted ureas of the formula Ia or Ib in which
the variables are as defined in any of claims 13 or 14 or
agriculturally useful salts thereof as herbicides.
17. A composition, comprising at least one substituted urea of
the formula Ia or Ib in which the variables are as defined in
any of claims 13 or 14 or an agriculturally useful salt of Ia
or Ib and customary auxiliaries.
18. A substituted urea of the formula Ia or Ib
<IMGS>
in which the variables X, Z, m, R, R A and Q are as defined in
any of claims 1 to 10, 14 or 15 and R is hydrogen,
except for those compounds of the formula Ia in which Z and X
are oxygen, m has the value 0, R is hydrogen and Q is a
radical of the formula Q1 in which R3 = fluorine and R4 =
chlorine and R5 is selected from the group consisting of
isopropoxy, propargyloxy, allyloxy, benzyloxy,
isopropoxycarbonyl, hydroxyiminomethyl, methoxyiminomethyl,
CH=NOCH2CO2CH3, -CH=N-O-C(CH3)2-CO2CH3, propargyloxyimino-
methyl, -CH=C(C1)-CO2CH3, -CH=C(C1)CO2C2H5,
-CH=C(C1)-CO2-CH2-CO2CH3, -CH=C(C1)-CO2-CH(CH3)CO2CH3,
-CH=C(C1)-CO2-CH2-CO2-tert-butyl, -CH=C(C1)-CO2H,
-CH=C(C1)-CONHOCH3, -CH=C(C1)-CONHOC2H5 or
-CH=N-O-CH(CH3)-CO2CH3;
or Q is a radical of the formula Q1 where R3 = R5 = hydrogen
and R5 = chlorine,
or Q is a radical of the formula Q1 where R3 = R4 = chlorine
and R5 = H, methoxyiminomethyl, -CH=C(C1)CO2H or
-CH=C(C1)-CO2C(CH3)3;

189
furthermore excluding compounds of the formula Ia in which Z
is oxygen and X is sulfur, m has the value 0, R is hydrogen
and Q is a radical of the formula Q4, where R3 = fluorine, Y
= oxygen and T-R7 = propargyl, allyl or 3-(ethoxycarbonyl)-
prop-2-yl or Q is a radical of the formula Q1 where R3 = R4 =
chlorine and R5 = hydrogen;
furthermore excluding N-(2,4-dichlorophenyl)tetrahydro-
4H-1,3,4-oxadiazine-4-carbothiamide;
furthermore excluding 2,2-dimethyl-4-(p-tolylcarbamoyl)-
tetrahydro-4H-1,3,4-oxadiazine.

Description

CA 02377143 2001-12-19
1
Substituted ureas
The present invention relates to substituted ureas having a
semicarbazide structure in which the hydrazino group is
incorporated into a 6-membered saturated heterocycle which has a
further heteroatom selected from the group consisting of oxygen
and sulfur in a position which is not adjacent to the nitrogen
atoms.
Moreover, the invention relates to the use of such substituted
ureas as herbicidal compositions comprising these compounds as
active substances, and to methods for controlling undesirable
vegetation using compounds of this type.
JP 9082-372 describes herbicidally active
tetrahydropyridazinecarboxylic acid derivatives and processes for
their preparation.
WO 94/10173 and the German Patent Application P 198.29.745.9
describe herbicidally active bicyclic triazolinediones and
processes for their preparation.
Surprisingly, it has now been found that substituted ureas of the
formula Ia and Ib, as defined below, have particularly good
herbicidal action. Furthermore, we have found herbicidal
compositions comprising the compounds Ia and Ib and having very
good herbicidal action. Moreover, we have found processes for
preparing these compositions and methods for controlling
undesirable vegetation using the compounds I.
Accordingly, the present invention relates to substituted ureas
of the formula Ia and Ib
X
~RA~m ~-NH_Q Z~N~~-NH- D
N'
~N ~Nw
U ~R ~RA~m R
la Ib
in which the variables X, Z, m, R and RA are as defined
below:
X is S or O;

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Z is O, S, S=O or 502;
m has the value 0, 1, 2 or 3;
R is hydrogen, C(0)ORlp, C(O)SRlo, C(S)ORlo, G(S)SR1~, C02H,
CHO, cyano, C(0)NR11R12, C(S)NR11R12, G(O)NHC(O)C1,
C(O)NHS(0)2C1, C(O)NHC(0)OR12', C(O)NHS(O)2R12~,
C(O)NHS(0)20R12', C(O)R2, P(O}R1(ORl), P(O)(OR1)2, S(O)nR2
where n = 0, 1 or 2, or S02NHR1;
RA is hydroxyl, C02R1, halogen, cyano, C(O)N(R1)2, where the
radicals R1 are, if appropriate, different from one
another, is OR2, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-alkenyl, C3-C6-alkynyl, COR1, S(O)nRl where n = 0, 1
or 2, or is C(O}SR1;
Q is one of the radicals Q1 to Q6:
3 3
~ ~ R4 ~ ~ Ra ~ ~ Ra
RS YY N N \ 'Y
URB ~IU'Re
Q-1 D-2 D-3
Y'
D-4 D-5 O-6
in Which
Y and Y' independently of one another are 0 or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O, S, SO or S02;

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and the radicals R1 to R3~ are as defined below:
R1 is hydrogen, C1-C6-alkyl, C1-Cs-haloalkyl,
C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl,
hydroxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkylthio-C1-C6-alkyl,
C1-C6-alkylsulfinyl-C1-C6-alkyl,
C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-cycloalkyl,
C3-C6-cycloalkyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl,
C3-C6-cycloalkoxy-C1-C6-alkyl,
C3-C6-alkenyloxy-Cl-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl,
G1-C6-haloalkoxy-C1-C6-alkyl,
C3-C6-haloalkenyloxy-C1-C6-alkyl,
C3-C6-haloalkynyloxy-C1-C6-alkyl,
C3-C6-cycloalkyl-C1-C6-thioalkyl,
C3-C6-alkenylthio-C1-C6-alkyl,
C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
C3-C6-halocycloalkyl-C1-C6-alkyl, halo-CZ-C6-alkenyl,
C1-C6-alkoxy-C3-C6-alkenyl,
C1-C6-haloalkoxy-C3-C6-alkenyl,
C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl,
C1-C6-alkoxy-C3-C6-alkynyl,
C1-C6-haloalkoxy-C3-C6-alkynyl,
C1-C6-alkylthio-C3-C6-alkynyl, C1-C6-alkylcarbonyl,
CHR1COR7, CHR1P(O)(OR7)Z, P(O)(OR7)2, CHR1P(S)(OR~)2,
CHR1C(O)NR11R12, CHR1C(O)NH2, phenoxy-C1-C6-alkyl or
benzyloxy-C1-C6-alkyl, where the benzene rings of the two
last-mentioned groups may for their part be substituted
by halogen, C1-C4-alkyl or C1-C4-haloalkyl; is benzyl
which may be substituted by halogen, C1-C4-alkyl or
C1-C4-haloalkyl or is phenyl or pyridyl, each of which
may be substituted by halogen, C1-C4-alkyl,
C1-C4-haloalkyl or C1-C4-alkoxy;
R3 is hydrogen or halogen;
R4 is C1-G6-alkyl, C1-C6-haloalkyl, OCH3, SCH3, OCHF2,
halogen, cyano or NOZ;

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R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-haloalkyl, Ci-C6-haloalkoxy, C1-C6-haloalkylthio,
Ci-C6-alkoxy-(C1-C6-alkyl)carbonyl,
Ci-C6-alkylthio-(Ci-C6-alkyl)carbonyl,
(C1-C6-alkyl)iminooxycarbonyl, Ci-C6-alkoxy-C1-C6-alkyl,
Ci-C6-alkoxyamino-Ci-C6-alkyl,
Ci-C6-alkoxy-Ci-C6-alkylamino-Ci-C6-alkyl,
is C1-C6-alkoxy, Ci-C6-alkylthio, C3-C6-cycloalkoxy,
C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio,
C2-C6-alkynyloxy, C2-C6-alkynylthio,
(Ci-C6-alkyl)carbonyloxy, (Ci-C6-alkyl)carbonylthio,
(Ci-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy,
(C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy,
(C2-C6-alkynyl)carbonylthio, Ci-C6-alkylsulfonyloxy or
Ci-C6-alkylsulfonyl, where each of the 17 last-mentioned
radicals may, if desired, carry one, two or three
substituents selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl,
Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy,
Ci-C6-alkylthio, Ci-C6-alkylsulfinyl,
Ci-C6-alkylsulfonyl, Ci-C6-alkylideneaminooxy, oxo,
=N-ORi 3 ;
- phenyl, phenoxy or phenylsulfonyl, where the three
last-mentioned groups may carry one, two or three
substituents selected from the group consisting of
halogen, nitro, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl;
- _C0_Rl4r _C0_OR14, -CO-SR14, -CO-N(R14)-Rl5r _OCO-R14,
-OCO-OR14 ~ , -OCO-SR14 ~ , -OCO-N ( R14 ) -R15 r _N ( R14 ) _R15 r
and -C(R16)=N-OR13~
C(Zi)-R17, -C(=NRi$)R17, C(R17)(Z2R19)(Z3R20)r
C(R17)=C(R21)_CN, C(R17)=C(R21)_C0_R22r
-CH(R17)-CH(R21)-COR22, -C(Ri7)=C(R21)_CHZ_CO_R22r
-C(R17)=C(R21)_C(R23)=C(R24)_C0_R22r
-C(R17)=C(R21)_CHZ_CH(R25)_C0_R22r _C0_OR26, -CO-SR26,
-CON(R26)-OR13, -CSC-CO-NHOR13, -CSC-CO-N(R26)-ORl3r
-CSC-CS-NH-OR13, -CiC-CS-N(R26)-ORl3r
_C(R17)=C(R21)_C0_NHOR13, -C(R17)=C(R21)_C0_N(R26)_0R13r
-C ( R17 ) =C ( R21 ) _CS_NHOR13 , -C ( R17 ) =C ( R21 ) _CS_N ( R26 ) _0813 r
-C ( R17 ) =C ( R21 ) _C ( R16 ) =N_OR13 r C ( R16 ) =N_OR13 r

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-CSC-C(Ris)=NOR13, C(Z2R19)(Z3R2o)_OR26~
-C(Z2R19) (Z2R2o)SR26, C(Z2R19) (Z3R20)_N(R27)R28~ _N(R27)-R2B~
-CO-N(RZ7)_RZe or _C(R17)=C(R21)CO-N(R2~)R28; where Zi, Z2,
Z3 independently of one another are oxygen or sulfur;
5
R6 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-alkenyl,
Ci-C3-alkoxy-C3-C6-alkenyl, C3-C6-haloalkenyl,
C3-C6-alkynyl, Ci-C3-alkoxy-C3-C6-alkynyl,
C3-C6-haloalkynyl, C3-C~-cycloalkyl, 3- to 7-membered
saturated heterocyclyl, where each cycloalkyl and each
heterocyclyl ring may contain a carbonyl or thiocarbonyl
ring member where each cycloalkyl and heterocyclyl ring
may be unsubstituted or may carry one, two, three or four
substitutents, selected from the group consisting of
cyano, nitro, amino, hydroxyl, halogen, Ci-C4-alkyl,
Ci-C4-haloalkyl, Ci-C4-cyanoalkyl, Ci-C4-hydroxyalkyl,
Ci-C4-aminoalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl,
Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl,
(Ci-C4-alkoxy)carbonyl, (Ci-C4-alkyl)carbonyl,
(Ci-C4-haloalkyl)carbonyl, (Ci-C4-alkyl)carbonyloxy,
(Ci-C4-haloalkyl)carbonyloxy, di(Ci-C4-alkyl)amino,
C3-C6-alkenyl, C3-C6-alkynyl, C3-C4-alkenyloxg,
C3-C4-alkenylthio, C3-C4-alkynyloxy and C3-C4-alkynylthio;
R7 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl,
C1-C3-alkoxy-Ci-C3-alkyl, C2-C6-cyanoalkyl, C3-C6-alkenyl,
C3-C6-alkynyl;
R8 is hydrogen, Ci-C3-alkyl, Ci-C3-haloalkyl or halogen;
R9 is hydrogen, Ci-C3-alkyl, Ci-C3-haloalkyl; or
R8 and R9 together are C=O;
R10 is Ci-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl,
C3-Cio-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl,
Ci-C6-alkylthio-Ci-C6-alkyl,
Ci-C6-alkylsulfinyl-Ci-C6-alkyl,
Ci-C6-alkylsulfonyl-Ci-C6-alkyl,
Ci-C3-alkoxy-Ci-C3-alkoxy-Ci-C3-alkyl,
C3-C6-cycloalkyl-C1-C6-alkyl, carboxyl-Ci-C6-alkyl,
Ci-C6-alkoxycarbonyl-Ci-C6-alkyl,
Ci-C6-alkoxycarbonyl-C2-C6-alkenyl,
C3-C6-alkenyloxycarbonyl-Ci-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl,

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C3-C8-cycloalkoxy-C1-C6-alkyl,
C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl,
C1-C6-haloalkoxy-C1-C6-alkyl,
C3-C6-haloalkenyloxy-C1-C6-alkyl,
C3-C6-haloalkynyloxy-C1-C6-alkyl,
C3-C6-cycloalkyl-C1-C6-thioalkyl,
C3-C6-alkenylthio-C1-C6-alkyl,
C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
C3-C6-halocyclo-C1-C6-alkyl, halo-C3-C6-alkenyl,
C1-C6-alkoxy-C3-C6-alkenyl,
C1-C6-haloalkoxy-C3-C6-alkenyl,
C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl,
C1-C6-alkoxy-C3-C6-alkynyl,
Cl-C6-haloalkoxy-C3-C6-alkynyl,
C1-C6-alkylthio-C3-C6-alkynyl, CHR1COR7, CHR1P(0)(OR~)2,
P(O)(OR7)2, CHR1P(S)(OR~)y, CHR1C(O)NR11R12, CHR1C(O)NH2,
C1-C6-alkyl, which is substituted by phenoxy or
benzyloxy, where the benzene rings of the two
last-mentioned groups may for their part be substituted
by halogen, C1-C4-alkyl or C1-CQ-haloalkyl;
is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl,
quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl,
2-methylindazolyl, benzofuranyl, benzothienyl,
benzoxazolyl, benzthiazolyl, benzyl, which may carry a
divalent substituent, such as methylenedioxy,
difluoromethylenedioxy, chlorofluoromethylenedioxy,
dichloromethylenedioxy, in adjacent positions or which
may in each case be mono- to pentasubstituted by halogen,
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio,
amino, C1-C4-monoalkylarnino, C1-C4-dialkylamino,
C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl,
C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or
cyano;
R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C2-C6-alkenyl, where the alkenyl
chain may additionally carry one to three halogen and/or
cyano radicals, are phenyl or benzyl which may carry a
divalent substituent, such as methylenedioxy,

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difluoromethylenedioxy, chlorofluoromethylenedioxy,
dichloromethylenedioxy, in adjacent positions or which
may be mono- to pentasubstituted by halogen, C1-C4-alkyl,
C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy,
C1-C4-alkylthio, C1-C4-haloalkylthio, amino,
C1-C4-monoalkylamino, C1-C4-dialkylamino,
C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl,
C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano
or
R11 and R1z together with the common nitrogen atom are a
saturated or unsaturated 4- to 7-membered azaheterocycle
which, in addition to carbon ring members, may, if
desired, contain one of the following members: -0-, -S-,
-N=, -NH- or N-(C1-C6-alkyl)-;
R12' is as defined for R12, but excluding hydrogen;
R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
hydroxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkylthio-C1-C6-alkyl, cyano-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C2-C6-alkenyl,
(C1-C6-alkyl)carbonyloxy-C1-C6-alkyl or
phenyl-C1-C6-alkyl, in which the phenyl ring may, if
desired, carry one, two or three substituents selected
from the group consisting of cyano, nitro, halogen,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
R14 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-CI-C6-alkyl,
(C3-C6-alkenyloxy)carbonyl-C1-C6-alkyl, phenyl or
phenyl-C1-C6-alkyl, where the phenyl ring of the two
last-mentioned groups may be unsubstituted or may carry
one, two or three radicals selected from the group
consisting of halogen, nitro, cyano, C1-C6-alkyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl;
R14' is as defined for R14, but excluding hydrogen;

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R15 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-cycloalkyl,
C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy,
C3-C6-alkenyl or C3-C6-alkenyloxy;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio,
(C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy,
C1-C6-alkylsulfonyloxy or C1-C6-haloalkylsulfonyloxy,
where the 12 last-mentioned radicals may carry one of the
following substituents: hydroxyl, cyano, hydroxycarbonyl,
C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)aminocarbonyl,
di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkyl)carbonyloxy.,
C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl;
is (C1-C6-alkyl)carbonyl, (C1-C6-haloalkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyloxy,
(C1-C6-alkyl)carbonylthio, (C1-C6-haloalkyl)carbonylthio,
(C1-C6-alkoxy)carbonylthio, C2-C6-alkenyl,
(C2-C6-alkenyl)carbonyloxy, CZ-C6-alkenylthio,
C3-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-alkynylthio,
(C2-C6-alkynyl)carbonyloxy, C3-C6-alkynylsulfonyloxy,
C3-C6-cycloalkyl, C3-C6-cycloalkyloxy,
C3-C6-cycloalkylthio, (C3-C6-cycloalkyl)carbonyloxy,
C3-C6-cycloalkylsulfonyloxy;
is phenyl, phenoxy, phenylthio, benzoyloxy,
phenylsulfonyloxy, phenyl-C1-C6-alkyl,
phenyl-C1-C6-alkoxy, phenyl-C1-C6-alkylthio,
phenyl-(C1-C6-alkyl)carbonyloxy or
phenyl-(C1-C6-alkyl)sulfonyloxy, where the phenyl rings
of the 10 last-mentioned radicals may be unsubstituted or
may for their part carry one to three substituents, in
each case selected from the group consisting of cyano,
nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy
and (C1-C6-alkoxy)carbonyl;
R17 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
CZ-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R18 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C3-C6-cycloalkoxy,
C5-C7-Cycl~alkenyloxy, C1-C6-haloalkoxy, w-

CA 02377143 2001-12-19
0050/50080
9
C3-C6-haloalkenyloxy, hydroxy-C1-C6-alkoxy,
cyano-C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-alkoxy,
C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxy-C3-C6-alkenyloxy,
(C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy,
(C1-C6-alkyl)carbamoyloxy, (C1-C6-haloalkyl)carbamoyloxy,
(C1-C6-alkyl)carbonyl-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl-C1-C6-alkoxy,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkoxy,
C1-C6-alkylthio-C1-C6-alkoxy,
di(Cl-C6-alkyl)amino-C1-C6-alkoxy, -N(R29)R3o, phenyl
which for its part may carry one, two or three
substituents, in each case selected from the group
consisting of cyano, vitro, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, CZ-C6-alkenyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
is phenyl-C1-C6-alkoxy, phenyl-(C1-C6-alkyl),
phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where
in each case one or two methylene groups of the carbon
chains in the four last-mentioned groups may be replaced
by -O-, -S- or -N(C1-C6-alkyl)- and where the phenyl
rings in the four last-mentioned groups may be
unsubstituted or may for their part carry one to three
substituents, selected from the group consisting of
cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
is C3-C~-heterocyclyl, C3-C~-heterocyclyl-C1-C6-alkyl,
C3-C7-heterocyclyl-C1-C6-alkoxy,
C3-C7-heterocyclyl-C3-C6-alkenyloxy or
C3-C7-heterocyclyl-C3-C6-alkynyloxy, where in each case
one or two methylene groups of the carbon chains in the
four last-mentioned groups may be replaced by -O-, -S- or
-N(C1-C6-alkyl)- and where each heterocycle may be
saturated, unsaturated or aromatic and is either
unsubstituted or for its part carries one to three
substituents, selected from the group consisting of
cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
CZ-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R19, R2o independently of one another are C1-C6-alkyl,
C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl or together are a saturated or
unsaturated 2- to 4-membered carbon chain which may carry
an oxo substituent, where a member of this chain which is
not adjacent/ to t~~e vaiiables Z2 and Z3 may be replaced

0050/50080
CA 02377143 2001-12-19
by -O-, -S-, -N=, -NH- or -N(G1-C6-alkyl)- and where the
carbon chain may carry one to three substituents selected
from the group consisting of cyano, nitro, amino,
halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy,
5 C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkyl,
cyano-C1-C6-alkyl, hydroxy-C1-C6-alkyl,
C1-C6-alkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl,
C3-C6-cycloalkoxy, carboxyl, (C1-C6-alkoxy)carbonyl,
10 (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl and phenyl; are
unsubstituted or substituted phenyl where the carbon
chain may also be substituted by a fused-on or
spiro-linked 3- to 7-membered ring which may contain, as
ring members, one or two heteroatoms selected from the
group consisting of oxygen, sulfur, nitrogen and
C1-C6-alkyl-substituted nitrogen and which may for its
part, if desired, carry one or two of the following
substituents: cyano, C1-C6-alkyl, CZ-C6-alkenyl,
C1-C6-alkoxy, cyano-C1-C6-alkyl, C1-C6-haloalkyl and
(C1-C6-alkoxy)carbonyl;
Rzl is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;
R22 is hydrogen, O-R31, S-R31, C1-C6-alkyl which may carry one
or two C1-C6-alkoxy substituents, is CZ-C6-alkenyl,
C2-C6-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl,
C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyliminooxy,
-N(R2~)R28 or phenyl which may be unsubstituted or may
carry one to three substituents, in each case selected
from the group consisting of cyano, nitro, halogen,
C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-alkoxy
and (C1-C6-alkoxy)carbonyl;
R23 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, -N(R27)R2e
or phenyl which for its part may carry one to three
substituents selected from the group consisting of cyano,
nitro, halogen, C1-C6-alkyl, C1-Cb-haloalkyl,
C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy,
C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;

0050/50080
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11
R25 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R2s~ R31 independently of one another are hydrogen,
C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or
CZ-C6-alkynyl, where the 4 last-mentioned groups may in
each case carry one or two of the following radicals:
cyano, halogen, hydroxyl, hydroxycarbonyl, C1-C6-alkoxy,
C1-C6-alkylthio, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyloxy,
(C3-C6-alkenyloxy)carbonyl;
are (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl,
C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl,
C1-C6-alkyloximino-C1-C6-alkyl, C3-C6-cycloalkyl;
are phenyl or phenyl-C1-C6-alkyl, where the phenyl rings
may be unsubstituted or may for their part carry one to
three substituents, in each case selected from the group
consisting of cyano, vitro, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R2~, R28, R29, R3~ independently of one another are hydrogen,
C1-C6-alkyl, C3-C6-alkenyl, C2-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl,
(C1-C6-alkoxy)carbonyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
are (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the
alkenyl chain may additionally carry one to three halogen
and/or cyano radicals, are C1-C6-alkylsulfonyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl, phenyl or
phenylsulfonyl, where the phenyl rings of the two
last-mentioned radicals may be unsubstituted or may for
their part carry one to three substituents, in each case
selected from the group consisting of cyano, vitro,
halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl; or
R2~ and R28 and/or
R29 and R3~ together with the respective common nitrogen atom
are a saturated or unsaturated 4- to 7-membered
azaheterocycle which, in addition to carbon ring members,
may, if desired, contain one of the following members:
-O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)-;

0050!50080
CA 02377143 2001-12-19
12
and the agriculturally useful salts of the compounds Ia and
Ib.
Such compounds are provided by the present invention, except for
those compounds of the formula Ia in which Z and X are oxygen, m
has the value 0, R is hydrogen and Q is a radical of the formula
Q1 where R3 = fluorine and R4 = chlorine and R5 is selected from
the group comprising isopropoxy, propargyloxy, allyloxy,
benzyloxy and isopropoxycarbonyl, hydroxyiminomethyl,
methoxyiminomethyl, CH=NOCH2C02CH3, -CH=N-O-C(CH3)2-COzCH3,
propargyloxyiminomethyl, -CH=C(C1)-COZCH3, -CH=C(C1)C02C2H5,
-CH=C(C1)-COZ-CHZ-COyCH3, -CH=C(C1)-COZ-CH(CH3)COZCH3,
-CH=C(C1)-C02-CH2-C02-tert-butyl, -CH=C(Cl)-C02H,
-CH=C(C1)-CONHOCH3, -CH=C(C1)-CONHOCZH5 or -CH=N-O-CH(CH3)-COZCH3;
or Q is a radical of the formula Q1 where R3 = R5 = hydrogen and
R5 = chlorine, or Q is a radical of the formula Q1 where R3 = R4 =
chlorine and RS = H, methoxyiminomethyl, -CH=C(Cl)COZH or
-CH=C(Cl)-C02C(CH3)3; furthermore excluding compounds of the
formula Ia in which Z is oxygen and X is sulfur, m has the value
0, R is hydrogen and Q is a radical of the formula Q4 where R3 =
fluorine, Y = oxygen and T-R~ = propargyl, ally! or
3-(ethoxycarbonyl)prop-2-yl or Q is a radical Q1 where R3 = R4 =
chlorine and R5 = hydrogen.
Depending on the substitution pattern, the compounds of the
formulae Ia and Ib can contain one or more chiral centers, in
which case they are present as enantiomer or diastereomer
mixtures. In the case of compounds Ia and Ib having at least one
olefinic radical, E/Z isomers are, if appropriate, also possible.
The invention provides both the pure enantiomers or diastereomers
and their mixtures.
Among the agriculturally useful salts, the salts of those cations
or the acid addition salts of those acids are particularly
suitable whose cations and anions, respectively, do not adversely
affect the herbicidal action of the compounds Ia and Ib. Thus,
suitable cations are in particular the ions of the alkali metals,
preferably lithium, sodium and potassium, of the alkaline earth
metals, preferably calcium, magnesium and barium, and of the
transition metals, preferably manganese, copper, zinc and iron,
and also the ammonium ion which may, if desired, carry one to
four C1-C4-alkyl substituents and/or one phenyl or benzyl
substituent, preferably diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, furthermore
phosphonium ions, sulfonium ions, preferably .

0050/50080
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13
tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably
tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride,
bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen
phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen
carbonate, carbonate, hexafluorosilicate, hexafluorophosphate,
benzoate, and the anions of C1-C4-alkanoic acids, preferably
formate, acetate, propionate and butyrate. They can be formed by
reacting the compounds of the formulae Ia and Ib with an acid of
the corresponding anion, preferably of hydrochloric acid,
hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic molecular moieties mentioned in the definitions of R1
to R2, R4 to R31 and on phenyl, cycloalkyl and heterocyclyl rings
are collective terms for individual enumerations of the
individual group members. All carbon chains, i.e. all
(unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties
can be straight-chain or branched.
Halogenated substituents preferably carry one to five identical
or different halogen atoms.
The term halogen denotes in each case fluorine, bromine, chlorine
or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
- C1-C4-alkyl: CH3, CZHS, n-propyl, CH(CH3)2, n-butyl,
CH(CH3)-C2H5, 2-methylpropyl or C(CH3)3, in particular CH3,
C2H5 or CH(CH3)2:
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above
which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example, CH2F,
CHF2, CF3, CH2C1, dichloromethyl, trichloromethyl,
chlorofluoromethyl, dichlorofluoromethyl,
chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl,
2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,
2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
2,2,2-trichloroethyl, C2F5, 2-fluoropropyl, 3-fluoropropyl,
2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,
3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,
3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,
2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,
1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-
2-chloro~thyl, 1-(b~~momethyl)-2-bromoethyl, 4-fluorobuLyl,

0050/50080
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14
4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular
CH2F, CHF2, CF3, CH2C1, 2-fluoroethyl, 2-chloroethyl or
2,2,2-trifluoroethyl;
- C1-C6-alkyl: Ci-C4-alkyl as mentioned above, and also, for
example, n-pentyl, 1-methylbutyl, 2-methylbutyl,
3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,
1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,
2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or
1-ethyl-2-methylpropyl, in particular CH3, C2H5, n-propyl,
CH(CH3)2, n-butyl, C(CH3)3, n-pentyl or n-hexyl;
- C1-C15-alkyl: C1-C6-alkyl as mentioned above, and also, for
example, n-heptyl, 1-methylhexyl, 2-methylhexyl,
3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl,
2-ethylpentyl, 3-ethylpentyl, 4-ethylpentyl,
1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl,
1,4-dimethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl,
3-methylheptyl, 4-methylheptyl, 5-methylheptyl,
6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl,
4-ethylhexyl, 1,1-dimethylhexyl, 1,2-dimethylhexyl,
1,3-dimethylhexyl, 1,4-dimethylhexyl, 1,5-dimethylhexyl,
n-nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl,
4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 7-methyloctyl,
1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl,
5-ethylheptyl, 6-ethylheptyl, 1,1-dimethylheptyl,
1,2-dimethylheptyl, 1,3-dimethylheptyl, 1,4-dimethylheptyl,
1,5-dimethylheptyl, 1,6-dimethylheptyl, n-decyl,
1-methylnonyl, 2-methylnonyl, 3-methylnonyl, 7-methylnonyl,
8-methylnonyl, 1-ethyloctyl, 2-ethyloctyl, 3-ethyloctyl,
4-ethyloctyl, 5-ethyloctyl, 6-ethyloctyl, 7-ethyloctyl,
8-ethyloctyl, 1,1-dimethyloctyl, 1,2-dimethyloctyl,
1,3-dimethyloctyl, 1,4-dimethyloctyl, 1,5-dimethyloctyl,
1,6-dimethyloctyl, 1,7-dimethyloctyl, n-undecyl,
1-methyldecyl, 1-ethylnonyl, 1,1-dimethylnonyl,
1-propyloctyl, 1-butylheptyl, 6-undecyl, n-dodecyl,
1-methylundecyl, 1-ethyldecyl, 1,1-dimethyldecyl,
1-propylnonyl, 1-butyloctyl, 7-dodecyl, n-tridecyl,
1-methyldodecyl, 1-ethylundecyl, l,l-dimethylundecyl,
n-tetradecyl, 1-methyltridecyl, 1-ethyldodecyl,
1,1-dimethyldodecyl, n-pentadecyl, 1-methyltetradecyl,
1-ethyltridecyl, 1,1-dimethyltridecyl, in particular CH3,
C2Hg, n-propyi, CH(CH3)2, ~r-butyl, (CH3)3, n-pentyl, n-hexyl,

0050/50080
CA 02377143 2001-12-19
n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl,
n-tridecyl, n-tetradecyl, n-pentadecyl;
- C1-C6-haloalkyl: C1-C6-alkyl as mentioned above which is
5 partially or fully substituted by fluorine, chlorine, bromine
and/or iodine, i.e., for example, one of the radicals
mentioned under C1-C4-haloalkyl, or 5-fluoro-1-pentyl,
5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl,
5,5,5-trichloro-1-pentyl, undecafluoropentyl,
10 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl,
6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl,
in particular chloromethyl, fluoromethyl, difluoromethyl,
trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or
2,2,2-trifluoroethyl;
- hydroxy-C1-C6-alkyl: for example hydroxymethyl,
2-hydroxyeth-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl,
1-hydroxyprop-2-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl,
4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 1-hydroxybut-3-yl,
2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3-yl,
2-hydroxy-2-methylprop-3-yl or 2-hydroxymethylprop-2-yl, in
particular 2-hydroxyethyl;
- cyano-C1-C6-alkyl: for example cyanomethyl, 1-cyanoeth-1-yl,
2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl,
3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl,
1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl,
4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,
1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,
2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or
2-cyanomethylprop-2-yl, in particular cyanomethyl or
2-cyanoethyl;
phenyl-C1-C6-alkyl: for example benzyl, 1-phenylethyl,
2-phenylethyl, 1-phenylprop-1-y1, 2-phenylprop-1-yl,
3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl,
3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl,
2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,
1-(phenylmethyl)eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl
or 1-(phenylmethyl)prop-1-yl, in particular benzyl or
2-phenylethyl;
- phenyl-(C1-C6-alkyl)carbonyloxy: for example
benzylcarbonyloxy, 1-phenylethylcarbonyloxy,
2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy,
2-phenylprop-1-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy,
1-phemylbut-1-yluarbonyloxy, 2-phenylbut-1-ylcarbonyloxy; ~~

0050/50080
CA 02377143 2001-12-19
16
3-phenylbut-1-ylcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy,
1-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy,
3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy,
1-(phenylmethyl)eth-1-ylcarbonyloxy, 1-(phenylmethyl)-
1-(methyl)eth-1-ylcarbonyloxy or 1-(phenylmethyl)-
prop-1-ylcarbonyloxy, in particular benzylcarbonyloxy or
2-phenylethylcarbonyloxy;
- phenyl-C1-C6-alkylsulfonyloxy: for example benzylsulfonyloxy,
1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy,
1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy,
3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-1-ylsulfonyloxy,
2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy,
4-phenylbut-1-ylsulfonyloxy, 1-phenylbut-2-ylsulfonyloxy,
2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy,
4-phenylbut-2-ylsulfonyloxy, 1-(phenylmethyl)eth-1-
ylsulfonyloxy, 1-(phenylmethyl)-1-(methyl)eth-1-ylsulfonyloxy
or 1-(phenylmethyl)prop-1-ylsulfonyloxy, in particular
benzylsulfonyloxy or 2-phenylethylsulfonyloxy;
- (C1-C6-alkyl)carbonyl: CO-CH3, CO-C2H5, n-propylcarbonyl,
1-methylethylcarbonyl, n-butylcarbonyl,
1-methylpropylcarbonyl, 2-methylpropylcarbonyl,
1,1-dimethylethylcarbonyl, n-pentylcarbonyl,
1-methylbutylcarbonyl, 2-methylbutylcarbonyl,
3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl,
1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl,
1-ethylpropylcarbonyl, n-hexylcarbonyl,
1-rnethylpentylcarbonyl, 2-methylpentylcarbonyl,
3-methylpentylcarbonyl, 4-methylpentylcarbonyl,
1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,
1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,
2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl,
1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,
1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,
1-ethyl-1-methylpropylcarbonyl or
1-ethyl-2-methylpropylcarbonyl, in particular CO-CH3, CO-C2H5
or CO-CH(CH3)2:
- (C1-C6-alkyl)carbonyl-C1-C6-alkyl: C1-C6-alkyl which is
substituted by (C1-C6-alkyl)carbonyl as mentioned above, i.e.,
for example, methylcarbonylmethyl;
- (C1-C6-haloalkyl)carbonyl: a (C1-C6-alkyl)carbonyl radical as
mentioned above which is partially or fully substituted by
fluorine, chlorine, bromine and/or iodine, i.e., for example,
chioroacetyl, dichloroacetyl, trichloroacetyi, fluoroacetyl,-

0050/50080
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17
difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl,
dichlorofluoroacetyl, chlorodifluoroacetyl,
2-fluoroethylcarbonyl, 2-chloroethylcarbonyl,
2-bromoethylcarbonyl, 2 -iodoethylcarbonyl,
2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl,
2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoro-
ethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl,
2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl,
2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl,
2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl,
2-chloropropylcarbonyl, 3-chloropropylcarbonyl,
2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl,
3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl,
3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoro-
propylcarbonyl, heptafluoropropylcarbonyl,
1-(fluoromethyl)-2-fluoroethylcarbonyl,
1-(chloromethyl)-2-chloroethylcarbonyl,
1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl,
4-chlorobutylcarbonyl, 4-bromobutylcarbonyl,
nonafluorobutylcarbonyl, (5-fluoro-1-pentyl)carbonyl,
(5-chloro-1-pentyl)carbonyl, (5-bromo-1-pentyl)carbonyl,
(5-iodo-1-pentyl)carbonyl, (5,5,5-trichloro-
1-pentyl)carbonyl, undecafluoropentylcarbonyl,
(6-fluoro-1-hexyl)carbonyl, (6-chloro-1-hexyl)carbonyl,
(6-bromo-1-hexyl)carbonyl, (6-iodo-1-hexyl)carbonyl,
(6,6,6-trichloro-1-hexyl)carbonyl or
dodecafluorohexylcarbonyl, in particular trifluoroacetyl;
- (C1-C6-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,
n-propylcarbonyloxy, 1-methylethylcarbonyloxy,
n-butylcarbonyloxy, 1-methylpropylcarbonyloxy,
2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy,
n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy,
2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy,
1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy,
2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy,
n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy,
2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy,
4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy,
1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy,
2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy,
3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy,
2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy,
1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropyl-
carbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, in
particular acetyloxy;

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18
- (C1-C6-haloalkyl)carbonyloxy: a (C1-C6-alkyljcarbonyloxy
radical as mentioned above which is partially or fully
substituted by fluorine, chlorine, bromine and/or iodine,
i.e., for example, chloroacetyloxy, dichloroacetyloxy,
trichloroacetyloxy, fluoroacetyloxy, difluoroacetyloxy,
trifluoroacetyloxy, chlorofluoroacetyloxy,
dichlorofluoroacetyloxy,_chlorodifluoroacetyloxy,
2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy,
2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy,
2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethyl-
carbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy,
2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-
2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy,
pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy,
3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy,
2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy,
3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy,
2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy,
3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropyl-
carbonyloxy, 2,2,3,3,3-pentafluoropropylcarbonyloxy,
heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoro-
ethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy,
1-(bromomethyl)-2-bromoethylcarbonyloxy,
4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy,
4-bromobutyl or nonafluorobutyl, in particular
trifluoroacetoxy;
- (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl: C1-C6-alkyl which is
substituted by (C1-C6-alkyl)carbonyloxy as mentioned above,
i.e., for example, methylcarbonyloxymethyl,
ethylcarbonyloxymethyl, 1-(methylcarbonyloxy)ethyl,
2-(methylcarbonyloxy)ethyl, 2-(ethylcarbonyloxy)ethyl,
3-(methylcarbonyloxy)propyl, 4-(methoxycarbonyloxy)butyl,
5-(methoxycarbonyloxy)pentyl or 6-(methoxycarbonyloxy)hexyl;
- (C1-C6-alkyl)carbonylthio: acetylthio, ethylcarbonylthio,
n-propylcarbonylthio, 1-methylethylcarbonylthio,
n-butylcarbonylthio, 1-methylpropylcarbonylthio,
2-methylpropylcarbonylthio, 1,1-dimethylethylcarbonylthio,
n-pentylcarbonylthio, 1-methylbutylcarbonylthio,
2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio,
1,1-dimethylpropylcarbonylthio, 1,2-dimethylpropyl-
carbonylthio, 2,2-dimethylpropylcarbonylthio,
1-ethylpropylcarbonylthio, n-hexylcarbonylthio,
1-methylpentylcarbonylthio, 2-methylpentylcarbonylthio,
3-methylperrtylcarbonylthio, 4-methylpentylcarbonylthio,
i,l-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio,~

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19
1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio,
2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio,
1-ethylbutylcarbonylthio, 2-ethylbutylcarbonylthio,
1,1,2-trimethylpropylcarbonylthio, 1,2,2 -trimethylpropyl-
carbonylthio, 1-ethyl-1-methylpropylcarbonylthio or
1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;
(C1-C6-haloalkyl)carbonylthio: a (C1-C6-alkyl)carbonylthio
radical as mentioned above which is partially or fully
substituted by fluorine, chlorine, bromine and/or iodine,
i.e., for example, chloroacetylthio, dichloroacetylthio,
trichloroacetylthio, fluoroacetylthio, difluoroacetylthio,
trifluoroacetylthio, chlorofluoroacetylthio,
dichlorofluoroacetylthio, chlorodifluoroacetylthio,
2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio,
2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio,
2,2-difluoroethylcarbonylthio, 2,2,2-trifluoroethyl-
carbonylthio, 2-chloro-2-fluoroethylcarbonylthio,
2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-
2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio,
pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio,
3-fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio,
2,3-difluorapropylcarbonylthio, 2-chloropropylcarbonylthio,
3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio,
2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio,
3,3,3-trifluoropropylcarbonylthio, 3,3,3-trichloropropyl-
carbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio,
heptafluoropropylcarbonylthio, 1-(fluoromethyl)-
2-fluoroethylcarbonylthio, 1-(chloromethyl)-2-chloro-
ethylcarbonylthio, 1-(bromomethyl)-2-bromoethylcarbonylthio,
4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio,
4-bromobutylthio or nonafluorobutylthio, in particular
trifluoroacetylthio;
- (C1-C6-alkyl)carbamoyloxy: methylcarbarnoyloxy,
ethylcarbamoyloxy, n-propylcarbamoyloxy,
1-methylethylcarbamoyloxy, n-butylcarbamoyloxy,
1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy,
1,1-dimethylethylcarbamoyloxy, n-pentylcarbamoyloxy,
1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy,
3-methylbutylcarbamoyloxy, 1,1-dimethylpropylcarbamoyloxy,
1,2-dimethylpropylcarbamoyloxy, 2,2-dimethylpropyl-
carbamoyloxy, 1-ethylpropylcarbamoyloxy, n-hexylcarbamoyloxy,
1-methylpentylcarbamoyloxy, 2-methylpentylcarbamoyloxy,
3-methylpentylcarbamoyloxy, 4-methylpentylcarbamoyloxy,
1,1-dimethylbutylcarbamoyloxy, 1,2-dimethylbutylcarbamoyloxy,
i,3-dimethylbutylcarbamoyloxy, 2,2-dimethylbutylearbamoyloxy,

0050/50080
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2,3-dimethylbutylcarbamoyloxy, 3,3-dimethylbutylcarbamoyloxy,
1-ethylbutylcarbamoyloxy, 2-ethylbutylcarbamoyloxy,
1,1,2-trimethylpropylcarbamoyloxy, 1,2,2-trimethylpropyl-
carbamoyloxy, 1-ethyl-1-methylpropylcarbamoyloxy or
5 1-ethyl-2-methylpropylcarbamoyloxy, in particular
methylcarbamoyloxy;
- (C1-C6-haloalkyl)carbamoyloxy: a (C1-C6-alkyl)carbamoyloxy
radical as mentioned above which is partially or fully
10 substituted by fluorine, chlorine, bromine and/or iodine,
i.e., for example, chloromethylcarbamoyloxy,
dichloromethylcarbamoyloxy, trichloromethylcarbamoyloxy,
fluoromethylcarbamoyloxy, difluoromethylcarbamoyloxy,
trifluoromethylcarbamoyloxy, chlorofluoromethylcarbamoyloxy,
15 dichlorofluoromethylcarbamoyloxy, chlorodifluoromethyl-
carbamoyloxy, 2-fluoroethylcarbamoyloxy,
2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy,
2-iodoethylcarbamoyloxy, 2,2-difluoroethylcarbamoyloxy,
2,2,2-trifluoroethylcarbamoyloxy, 2-chloro-2-fluoroethyl-
20 carbamoyloxy, 2-chloro-2,2-difluoroethylcarbamoyloxy,
2,2-dichloro-2-fluoroethylcarbamoyloxy, 2,2,2-trichloroethyl-
carbamoyloxy, pentafluoroethylcarbamoyloxy, 2-fluoropropyl-
carbamoyloxy, 3-fluoropropylcarbamoyloxy, 2,2-difluoro-
propylcarbamoyloxy, 2,3-difluoropropylcarbamoyloxy,
2-chloropropylcarbamoyloxy, 3-chloropropylcarbamoyloxy,
2,3-dichloropropylcarbamoyloxy, 2-bromopropylcarbamoyloxy,
3-bromopropylcarbamoyloxy, 3,3,3-trifluoropropylcarbamoyloxy,
3,3,3-trichloropropylcarbamoyloxy, 2,2,3,3,3-pentafluoro-
propylcarbamoyloxy, heptafluoropropylcarbamoyloxy,
1-(fluoromethyl)-2-fluoroethylcarbamoyloxy, 1-(chloromethyl)-
2-chloroethylcarbamoyloxy, 1-(bromomethyl)-2-bromoethyl-
carbamoyloxy, 4-fluorobutylcarbamoyloxy, 4-chlorobutyl-
carbamoyloxy, 4-bromobutylcarbamoyloxy or nonafluorobutyl-
carbamoyloxy, in particular trifluoromethylcarbamoyloxy;
- C1-C6-alkoxy: for example OCH3, OCZHS, OCHz-C2H5, OCH(CH3)z.
n-butoxy, OCH(CH3)-CZHS, OCHz-CH(CH3)z, OC(CH3)3, n-pentoxy,
1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,
1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-
propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy,
2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,
1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,
2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,
1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,
1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and

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21
1-ethyl-2-methylpropoxy, in particular OCH3, OC2H5 or
OCH(CH3)Z;
- C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above
which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example,
chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy,
chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,
2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,
2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,
3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,
2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy,
3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy,
heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy,
1-(chloromethyl)-2-chloroethoxy,
1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy,
4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in
particular 2-chloroethoxy or 2,2,2-trifluoroethoxy;
- C1-C6-haloalkoxy: a C1-C6-alkoxy radical as mentioned above
which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example, one of
the radicals mentioned under C1-C4-haloalkoxy, or
5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy,
5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy,
undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy,
6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy
or dodecafluorohexoxy, in particular chloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;
hydroxy-C1-C6-alkoxy: for example OCH2-OH, OCH(CH3)-OH,
OCHZ-CH2-OH, OCH(CZHS)-OH, OCHZ-CH(CH3)-OH,
3-hydroxyprop-I-yloxy, 1-hydroxybut-1-yloxy,
2-hydroxybut-1-yloxy, 3-hydroxybut-1-yloxy,
4-hydroxybut-1-yloxy, 1-hydroxybut-2-yloxy,
2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy,
4-hydroxybut-2-yloxy, 1-(CH2-OH)-eth-1-yloxy,
1-(CH2-OH)-1-(CH3)-eth-1-yloxy or 1-(CHZ-OH)-prop-Z-yloxy, in
particular OCH2-OH or OCH2-CH2-OH;

0050/50080
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22
- cyano-C1-C6-alkoxy: for example OCHZ-CN, OCH(CH3)-CN,
OCHz-CH2-CN, OCH(CpHS)-OH, OCH2-CH(CH3)-CN,
3-cyanoprop-1-yloxy, 1-cyanobut-1-yloxy, 2-cyanobut-1-yloxy,
3-cyanobut-1-yloxy, 4-cyanobut-1-yloxy, 1-cyanobut-2-yloxy,
2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy,
1-(CH2-CN)-eth-1-yloxy, 1-(CHZ-CN)-1-(CH3)-eth-1-yloxy or
1-(CH2-CN)-prop-1-yloxy, in particular OCHZ-CN or OCH2-CH2-CN;
- phenyl-C1-C6-alkoxy: for example benzyloxy, 1-phenylethoxy,
2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy,
3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy,
2-phenylbut-1-yloxy, 3-phenylbut-1-yloxy,
4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy,
2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy,
4-phenylbut-2-yloxy, 1-(benzyl)eth-1-yloxy,
1-(benzyl)-1-(methyl)eth-1-yloxy or 1-(benzyl)prop-1-yloxy,
in particular benzyloxy or 2-phenylethoxy;
- heterocyclyl-C1-C6-alkoxy: for example heterocyclylmethoxy,
1-(heterocyclyl)ethoxy, 2-(heterocyclyl)ethoxy,
1-(heterocyclyl)prop-1-yloxy, 2-(heterocyclyl)prop-1-yloxy,
3-(heterocyclyl)prop-1-yloxy, 1-(heterocyclyl)but-1-yloxy,
2-(heterocyclyl)but-1-yloxy, 3-(heterocyclyl)but-1-yloxy,
4-(heterocyclyl)but-1-yloxy, 1-(heterocyclyl)but-2-yloxy,
2-(heterocyclyl)but-2-yloxy, 3-(heterocyclyl)but-2-yloxy,
4-(heterocyclyl)but-2-yloxy,
1-(heterocyclylmethyl)-eth-1-yloxy,
1-(heterocyclylmethyl)-1-(methyl)-eth-1-yloxy or
1-(heterocyclylmethyl)-prop-1-yloxy, in particular
heterocyclylmethoxy or 2-(heterocyclyl)ethoxy;
- phenyl-C1-C6-alkylthio: for example benzylthio,
1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-1-ylthio,
2-phenylprop-1-ylthio, 3-phenylprop-1-ylthio,
1-phenylbut-1-ylthio, 2-phenylbut-1-ylthio,
3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio,
1-phenylbut-2-ylthio, 2-phenylbut-2-ylthio,
3-phenylbut-2-ylthio, 4-phenylbut-2-ylthio,
1-(phenylmethyl)eth-1-ylthio,
1-(phenylmethyl)-1-(methyl)eth-1-ylthio or
1-(phenylmethyl)prop-1-ylthio, in particular benzylthio or
2-phenylethylthio;
- (C1-C6-alkoxy)carbonyl: for example -CO-OCH3, CO-OC2H5,
COO-CH2-C2H5, CO-OCH(CH3)Z, n-butoxycarbonyl, CO-OCH(CH3)-C2H5,
CO-OCH2-CH(CH3)2, CO-OC(CH3)3, n-pentoxycarbonyl,
I-methyibutoxycarboryl, 2-~nethylbutoxycarbonyl,

0050/50080
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23
3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,
1-ethylpropoxycarbonyl, n-hexoxycarbonyl,
1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,
1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,
3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,
1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,
1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,
2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,
1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,
1,1,2-trimethylpropoxycarbonyl,
1,2,2-trimethylpropoxycarbonyl,
1-ethyl-1-methylpropoxycarbonyl or
1-ethyl-2-methylpropoxycarbonyl, in particular CO-OCH3,
CO-OC2H5, CO-OCH(CH3)z or CO-CHZ-CH(CH3)2:
- (C1-C6-alkoxy)carbonyloxy: methoxycarbonyloxy,
ethoxycarbonyloxy, n-propoxycarbonyloxy,
1-methylethoxycarbonyloxy, n-butoxycarbonyloxy,
1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy,
1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy,
1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy,
3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy,
1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy,
1,1-dimethylpropoxycarbonyloxy,
1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy,
2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy,
4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy,
1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy,
2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy,
3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy,
2-ethylbutoxycarbonyloxy, 1,1,2-trimethylpropoxycarbonyloxy,
1,2,2-trimethylpropoxycarbonyloxy,
1-ethyl-1-methylpropoxycarbonyloxy or
1-ethyl-2-methylpropoxycarbonyloxy, in particular
methoxycarbonyloxy, ethoxycarbonyloxy or
1-methylethoxycarbonyloxy;
- (C1-C6-alkoxy)carbonylthio: methoxycarbonylthio,
ethoxycarbonylthio, n-propoxycarbonylthio,
1-methylethoxycarbonylthio, n-butoxycarbonylthio,
1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio,
1,1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio,
1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio,
3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio,
1-ethylpropoxycarbonylthio, n-hexoxycarbonylthia,
1,1-dimethylpropoxycarbonylthio,
1, 2-dimethylpropoxycarboizylthi~, 1-methylpen'coxycarbaziylvhio,

0050/50080
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24
2-methylpentoxycarbonylthio, 3-methylpentoxycarbonylthio,
4-methylpentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio,
1,2-dimethylbutoxycarbonylthio,
1,3-dimethylbutoxycarbonylthio,
2,2-dimethylbutoxycarbonylthio,
2,3-dimethylbutoxycarbonylthio,
3,3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio,
2-ethylbutoxycarbonylthio,
1,1,2-trimethylpropoxycarbonylthio,
1,2,2-trimethylpropoxycarbonylthio, 1-ethyl-
1-methylpropoxycarbonylthio or
1-ethyl-2-methylpropoxycarbonylthio, in particular
methoxycarbonylthio, ethoxycarbonylthio or
1-methylethoxycarbonylthio;
- C1-C6-alkylthio: SCH3, SC2H5, SCH2-C2H5, SCH(CH3)2,
n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC(CH3)3.
n-pentylthio, 1-methylbutylthio, 2-methylbutylthio,
3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,
n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,
1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,
4-methylpentylthio, I,1-dimethylbutylthio,
1,2-dimethylbutylthio, 1,3-dimethylbutylthio,
2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,
1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,
1-ethyl-1-methylpropylthio and 1-ethyl-
2-methylpropylthio, in particular SCH3 or SC2H5;
- C1-C6-haloalkylthio: C1-C6-alkylthio as mentioned above which
is partially or fully substituted by fluorine, chlorine,
bromine and/or iodine, i.e., for example, SCHF2, SCF3,
chlorodifluoromethylthio, bromodifluoromethylthio,
2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,
2-iodoethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,
2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,
2,2-dichloro-2-fluoroethylthio, SC2F5, 2-fluoropropylthio,
3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,
2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio,
2,3-difluoropropylthio, 2,3-dichloropropylthio,
3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio,
2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio,
1-(fluoromethyl)-2-fluoroethylthio,
1-(chloromethyl)-2-chloroethylthio,
1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,
4-chlorobutyltl~io, 4-broiaobutylthio, nonafluorobutyl~chio,

0050/50080
CA 02377143 2001-12-19
5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,
5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio
or 6-chlorohexylthio, in particular SCHZF, SCHF2, SCF3,
SCHZC1, 2-fluoroethylthio, 2-chloroethylthio or
5 2,2,2-trifluoroethylthio;
C1-C6-alkylsulfinyl: SO-CH3, SO-C2H5, n-propylsulfinyl,
1-methylethylsulfinyl, n-butylsulfinyl,
1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
10 1,1-dimethylethylsulfinyl, n-pentylsulfinyl,
1-methylbutylsulfinyl, 2-methylbutylsulfinyl,
3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl,
1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl,
1-ethylpropylsulfinyl, n-hexylsulfinyl,
15 1-methylpentylsulfinyl, 2-methylpentylsulfinyl,
3-methylpentylsulfinyl, 4-methylpentylsulfinyl,
1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,
1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,
2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,
20 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,
1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,
1-ethyl-1-methylpropylsulfinyl or
1-ethyl-2-methylpropylsulfinyl, in particular SO-CH3;
25 - C1-C6-alkylsulfonyl: SOZ-CH3, S02-CzH5, n-propylsulfonyl,
S02-CH(CH3)2, n-butylsulfonyl, 1-methylpropylsulfonyl,
2-methylpropylsulfonyl, S02-C(CH3)3, n-pentylsulfonyl,
1-methylbutylsulfonyl, 2-methylbutylsulfonyl,
3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,
1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,
1-ethylpropylsulfonyl, n-hexylsulfonyl,
1-methylpentylsulfonyl, 2-methylpentylsulfonyl,
3-methylpentylsulfonyl, 4-methylpentylsulfonyl,
1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,
1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,
2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,
1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,
1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,
1-ethyl-1-methylpropylsulfonyl or
1-ethyl-2-methylpropylsulfonyl, in particular S02-CH3;
- C1-C6-alkylsulfonyloxy: O-S02-CH3, O-S02-C2H5,
n-propylsulfonyloxy, O-S02-CH(CH3)Z, n-butylsulfonyloxy,
1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy,
0-SOZ-C(CH3)3, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy,
2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy,
1,1-dimeihylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyluxy,

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2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy,
n-hexylsulfonyloxy, 1-methylpentylsulfonyloxy,
2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy,
4-methylpentylsulfonyloxy, 1,1-dimethylbutylsulfonyloxy,
1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutylsulfonyloxy,
2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutylsulfonyloxy,
3,3-dimethylbutylsulfonyloxy, 1-ethylbutylsulfonyloxy,
2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy,
1,2,2-trimethylpropylsulfonyloxy,
1-ethyl-1-methylpropylsulfonyloxy or
1-ethyl-2-methylpropylsulfonyloxy, in particular
methylsulfonyloxy;
C1-C6-haloalkylsulfonyloxy: C1-C6-alkylsulfonyloxy as
mentioned above which is partially or fully substituted by
fluorine, chlorine, bromine and/or iodine, i.e., for example,
C1CH2-S02-O-, CH(Cl)2-SOZ-O-, C(Cl)g-SOp-O-, FCHZ-S02-O-,
CHF2-S02-O-, CF3-SOz-O-, chlorofluoromethyl-SOZ-O-,
dichlorofluoromethyl-S02-O-, chlorodifluoromethyl-S02-O-,
1-fluoroethyl-S02-0-, 2-fluoroethyl-S02-O-,
2-chloroethyl-S02-O-, 2-bromoethyl-SOZ-0-, 2-iodoethyl-SOZ-O-,
2,2-difluoroethyl-S02-0-, 2,2,2-trifluoroethyl-SOZ-O-,
2-chloro-2-fluoroethyl-SOz-O-,
2-chloro-2,2-difluoroethyl-SOZ-O-,
2,2-dichloro-2-fluoroethyl-SOZ-O-,
2,2,2-trichloroethyl-S02-O-, C2F5-S02-0-,
2-fluoropropyl-S02-O-, 3-fluoropropyl-S02-O-,
2,2-difluoropropyl-S02-O-, 2,3-difluoropropyl-S02-O-,
2-chloropropyl-S02-0-, 3-chloropropyl-S02-O-,
2,3-dichloropropyl-S02-O-, 2-bromopropyl-S02-O-,
3-bromopropyl-S02-0-, 3,3,3-trifluoropropyl-S02-O-,
3,3,3-trichloropropyl-S02-O-,
2,2,3,3,3-pentafluoropropyl-S02-O-, CzFS-CFZ-S02-O-,
1-(fluoromethyl)-2-fluoroethyl-S02-0-,
1-(chloromethyl)-2-chloroethyl-S02-O-,
1-(bromomethyl)-2-bromoethyl-SOz-O-, 4-fluorobutyl-SOZ-O-,
4-chlorobutyl-SOZ-O-, 4-bromobutyl-S02-O-, CzFS-CF2-CF2-S02-0-,
5-fluoropentyl-SO2-O-, 5-chloropentyl-SO2-O-,
5-bromopentyl-S02-O-, 5-iodopentyl-S02-O-,
5,5,5-trichloropentyl-S02-0-, C2F5-CFZ-CF2-CF2-S02-O-,
6-fluorohexyl-SOZ-O-, 6-chlorohexyl-S02-0-,
6-bromohexyl-SOZ-O-, 6-iodohexyl-S02-O-,
6,6,6-trichlorohexyl-S02-0- or dodecafluorohexyl-S02-O-, in
particular CF3-S02-O-;

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27
- (C1-C6-alkyl)aminocarbonyl: (C1-C4-alkyl)aminocarbonyl as
mentioned above and also for example, n-pentylaminocarbonyl,
1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,
3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,
1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl,
1,1-dimethylpropylaminocarbonyl,
1,2-dimethylpropylaminocarbonyl, I-methylpentylaminocarbonyl,
2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,
4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,
1,2-dimethylbutylaminocarbonyl,
1,3-dimethylbutylaminocarbonyl,
2,2-dimethylbutylaminocarbonyl,
2,3-dimethylbutylaminocarbonyl,
3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,
2-ethylbutylaminocarbonyl,
1,1,2-trimethylpropylaminocarbonyl,
1,2,2-trimethylpropylaminocarbonyl,
1-ethyl-1-methylpropylaminocarbonyl or
1-ethyl-2-methylpropylaminocarbonyl, in particular CO-NH-CH3,
CO-NH-C2H5 or CO-NH-CH(CH3)2:
- di(C1-C6-alkyl)aminocarbonyl: for example
N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,
N,N-dipropylaminocarbonyl,
N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl,
N,N-di(1-rnethylpropyl)aminocarbonyl,
N,N-di(2-methylpropyl)aminocarbonyl,
N,N-di(1,1-dimethylethyl)aminocarbonyl,
N-ethyl-N-methylaminocarbonyl,
N-methyl-N-propylaminocarbonyl,
N-methyl-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-methylaminocarbonyl,
N-methyl-N-(1-methylpropyl)aminocarbonyl,
N-methyl-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-methylaminocarbonyl,
N-ethyl-N-propylaminocarbonyl,
N-ethyl-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-ethylaminocarbonyl,
N-ethyl-N-(1-methylpropyl)aminocarbonyl,
N-ethyl-N-(2-methylpropyl)aminocarbonyl,
N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,
N-(1-methylethyl)-N-propylaminocarbonyl,
N-butyl-N-propylaminocarbonyl,
N-(1-methylpropyl)-N-propylaminocarbonyl,
N-(2-methylpropyl)-N-propylaminocarbonyl,
N-(1,1-dimethylethyl)-N-propylaminocarbonyl,
N-butyl-N-~i-methylethyl)aminocarbonyl, - w

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N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,
N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,
N-butyl-N-(1-methylpropyl)aminocarbonyl,
N-butyl-N-(2-methylpropyl)aminocarbonyl,
N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,
N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in
particular N,N-dimethylaminocarbonyl or
N,N-diethylaminocarbonyl;
- (C1-C6-alkyl)iminooxycarbonyl: methyliminooxycarbonyl,
ethyliminooxycarbonyl, n-propyliminooxycarbonyl,
1-methylethyliminooxycarbonyl, n-butyliminooxycarbonyl,
1-methylpropyliminooxycarbonyl,
2-methylpropyliminooxycarbonyl,
1,1-dimethylethyliminooxycarbonyl, n-pentyliminooxycarbonyl,
1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl,
3-methylbutyliminooxycarbonyl,
1,1-dimethylpropyliminooxycarbonyl,
1,2-dimethylpropyliminooxycarbonyl,
2,2-dimethylpropyliminooxycarbonyl,
1-ethylpropyliminooxycarbonyl, n-hexyliminooxycarbonyl,
1-methylpentyliminooxycarbonyl,
2-methylpentyliminooxycarbonyl,
3-methylpentyliminooxycarbonyl,
4-methylpentyliminooxycarbonyl,
1,1-dimethylbutyliminooxycarbonyl,
1,2-dimethylbutyliminooxycarbonyl,
1,3-dimethylbutyliminooxycarbonyl,
2,2-dimethylbutyliminooxycarbonyl,
2,3-dimethylbutyliminooxycarbonyl,
3,3-dimethylbutyliminooxycarbonyl,
1-ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl,
1,1,2-trimethylpropyliminooxycarbonyl,
1,2,2-trimethylpropyliminooxycarbonyl,
1-ethyl-1-methylpropyliminooxycarbonyl or
1-ethyl-2-methylpropyliminooxycarbonyl, in particular
methyliminooxycarbonyl, ethyliminooxycarbonyl or
1-methylethyliminooxycarbonyl;
- C1-C6-alkylideneaminooxy: 1-propylideneaminooxy,
2-propylideneaminooxy, 1-butylideneaminooxy,
2-butylideneaminooxy or 2-hexylideneaminooxy, in particular
acetylideneaminooxy or 2-propylideneaminooxy;

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- C1-C6-alkyliminooxy: methyliminooxy, ethyliminooxy,
n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy,
1-methylpropyliminooxy, 2-methylpropyliminooxy,
n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy,
2-methylpentyliminooxy, 3-methylpentyliminooxy or
4-methylpentyliminooxy, in particular methyliminooxy,
ethyliminooxy or 1-methylethyliminooxy;
- C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl:
(C1-C6-alkyl)aminocarbonyl such as CO-NH-CH3, CO-NH-C2H5.
CO-NH-CH2-C2H5, CO-NH-CH(CH3)y, CO-NH-(CH2)3-CH3,
CO-NH-CH(CH3)-C2H5, CO-NH-CH2-CH(CH3)Z, CO-NH-C(CH3)3.
CO-NH-(CH2)4-CH3, 1-methylbutylaminocarbonyl,
2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,
2,2-dimethylpropylaminocarbonyl, 1-ethylpropylarninocarbonyl,
n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,
1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,
2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,
4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,
1,2-dimethyTbutylaminocarbonyl,
1,3-dimethylbutylaminocarbonyl,
2,2-dimethylbutylaminocarbonyl,
2,3-dimethylbutylaminocarbonyl,
3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,
2-ethylbutylaminocarbonyl,
1,1,2-trimethylpropylaminocarbonyl,
1,2,2-trimethylpropylaminocarbonyl,
1-ethyl-1-methylpropylaminocarbonyl and
1-ethyl-2-methylpropylaminocarbonyl, preferably
(C1-C4-alkyl)aminocarbonyl, which is substituted by
C1-C6-alkoxy as mentioned above, i.e., for example,
CO-NH-CHZ-OCH3 or CO-NH-CHZ-OCZH5;
- C1-C6-alkoxyamino-C1-C6-alkyl: for example CHZ-NH-OCH3,
CH2-NH-OCZHS, CHy-NH-OCH2-C2H5, CH2-NH-OCH(CH3)yr
CH2-NH-OCHp-CHZ-CyHS, CH2-NH-OCH(CH3)-C2H5,
CH2-NH-OCH2-CH(CHg)2, CH2-NH-OC(CH3)3, CHZ-NH-OCH2-(CHz)3-cH3,
(1-methylbutoxyamino)methyl, (2-methylbutoxyamino)methyl,
(3-methylbutoxyamino)methyl,
(2,2-dimethylpropoxyamino)methyl,
(1-ethylpropoxyamino)methyl, n-hexoxyaminomethyl,
(1,1-dimethylpropoxyamino)methyl,
(1,2-dimethylpropoxyamino)methyl,
(1-methylpentoxyamino)methyl, (2-methylpentoxyamino)methyl,
(3-methylpentoxyamino)methyl, (4-methylpentoxyamino)methyl,
(1,1-dimethylbutoxyamino)methyl,
(1,2-dimethylbutoxyamino)methyl,

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(1,3-dimethylbutoxyamino)methyl,
(2,2-dimethylbutoxyamino)methyl,
(2,3-dimethylbutoxyamino)methyl,
(3,3-dimethylbutoxyamino)methyl, (1-ethylbutoxyamino)methyl,
5 (2-ethylbutoxyamino)methyl,
(1,1,2-trimethylpropoxyamino)methyl,
(1,2,2-trimethylpropoxyamino)methyl,
(1-ethyl-1-methylpropoxyamino)methyl,
(1-ethyl-2-methylpropoxyamino)methyl, methoxyaminoethyl,
10 ethoxyaminoethyl, n-propoxyaminoethyl,
(1-methylethoxyamino)ethyl, n-butoxyaminoethyl,
(1-methylpropoxyamino)ethyl, (2-methylpropoxyamino)ethyl,
(l,l-dimethylethoxyamino)ethyl, n-pentoxyaminoethyl,
(1-methylbutoxyamino)ethyl, (2-methylbutoxyamino)ethyl,
15 (3-methylbutoxyamino)ethyl, (2,2-dimethylpropoxyamino)ethyl,
(1-ethylpropoxyamino)ethyl, n-hexoxyaminoethyl,
(1,1-dimethylpropoxyamino)ethyl,
(1,2-dimethylpropoxyamino)ethyl, (1-methylpentoxyamino)ethyl,
(2-methylpentoxyamino)ethyl, (3-methylpentoxyamino)ethyl,
20 (4-methylpentoxyamino)ethyl, (1,1-dimethylbutoxyamino)ethyl,
(1,2-dimethylbutoxyamino)ethyl,
(1,3-dimethylbutoxyamino)ethyl,
(2,2-dimethylbutoxyamino)ethyl,
(2,3-dimethylbutoxyamino)ethyl,
25 (3,3-dimethylbutoxyamino)ethyl, (1-ethylbutoxyamino)ethyl,
(2-ethylbutoxyamino)ethyl,
(1,1,2-trimethylpropoxyamino)ethyl,
(1,2,2-trimethylpropoxyamino)ethyl,
(1-ethyl-1-methylpropoxyamino)ethyl,
30 (1-ethyl-2-methylpropoxyamino)ethyl, 2-(methoxyamino)propyl,
3-(methoxyamino)propyl or 2-(ethoxyamino)propyl, preferably
C1-C6-alkoxyamino-C1-C2-alkyl;
- C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl:
C1-C6-alkylamino-C1-C6-alkyl, such as CHZ-NH-CH3, CHZ-NH-C2H5,
CHZ-NH-CH2-C2H5, CH2-NH-CH(CH3)Z, CH2-NH-(CHZ)3-CH3,
CHZ-NH-CH(CH3)-C2H5, CH2-NH-CHZ-CH(CH3)Z, CH2-NH-C(CH3)g,
CHy-NH-(CH2)4-CH3, (1-methylbutylamino)methyl,
(2-methylbutylamino)methyl, (3-methylbutylamino)methyl,
(2,2-dimethylpropylamino)methyl, (1-ethylpropylamino)methyl,
n-hexylamino-methyl, (1,1-dimethylpropylamino)methyl,
(1,2-dimethylpropylamino)methyl, (1-methylpentylamino)methyl,
(2-methylpentylamino)methyl, (3-methylpentylamino)methyl,
(4-methylpentylamino)methyl, (1,1-dimethylbutylamino)methyl,
(1,2-dimethylbutylamino)methyl,
(1,3-dimethylbutylamino)methyl,
(2,2-d~methylbutylamino)methyl,

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(2,3-dimethylbutylamino)methyl,
(3,3-dimethylbutylamino)methyl, (1-ethylbutylamino)methyl,
(2-ethylbutylamino)methyl,
(1,1,2-trimethylpropylamino)methyl,
(1,2,2-trimethylpropylamino)methyl,
(1-ethyl-1-methylpropylamino)methyl,
(1-ethyl-2-methylpropylamino)methyl, methylaminoethyl,
ethylaminoethyl, n-propylaminoethyl,
(1-methylethylamino)ethyl, n-butylaminoethyl,
(1-methylpropylamino)ethyl, (2-methylpropylamino)ethyl,
(l,l-dimethylethylamino)ethyl, n-pentylaminoethyl,
(1-methylbutylamino)ethyl, (2-methylbutylamino)ethyl,
(3-methylbutylamino)ethyl, (2,2-dimethylpropylamino)ethyl,
(1-ethylpropylamino)ethyl, n-hexylaminoethyl,
(1,1-dimethylpropylamino)ethyl,
(1,2-dimethylpropylamino)ethyl, (1-methylpentylamino)ethyl,
(2-methylpentylamino)ethyl, (3-methylpentylamino)ethyl,
(4-methylpentylamino)ethyl, (1,1-dimethylbutylamino)ethyl,
(1,2-dimethylbutylamino)ethyl, (1,3-dimethylbutylamino)ethyl,
(2,2-dimethylbutylamino)ethyl, (2,3-dimethylbutylamino)ethyl,
(3,3-dimethylbutylamino)ethyl, (1-ethylbutylamino)ethyl,
(2-ethylbutylamino)ethyl, (1,1,2-trimethylpropylarnino)ethyl,
(1,2,2-trimethylpropylamino)ethyl,
(1-ethyl-1-methylpropylamino)ethyl,
(1-ethyl-2-methylpropylamino)ethyl, 2-(methylamino)propyl,
3-(methylamino)propyl and 2-(ethylamino)propyl, preferably
C1-C6-alkylamino-C1-CZ-alkyl, which is substituted by
C1-C6-alkoxy as mentioned above, i.e., for example,
CH2-NH-CHZ-OCH3 or CH2-NH-CH2-OC2H5;
- C1-C6-alkyloximino-C1-C6-alkyl: C1-C6-alkyl which is
substituted by C1-C6-alkyloximino, such as methoxyimino,
ethoxyimino, 1-propoxyimino, 2-propoxyimino,
1-methylethoxyimino, n-butoxyimino, sec-butoxyimino,
tert-butoxyimino, 1-methyl-1-propoxyimino,
2-methyl-1-propoxyimino, 1-methyl-2-propoxyimino,
2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino,
3-pentoxyimino, 4-pentoxyimino, 1-methyl-1-butoxyimino,
2-methyl-1-butoxyimino, 3-methyl-1-butoxyimino,
1-methyl-2-butoxyimino, 2-methyl-2-butoxyimino,
3-methyl-2-butoxyimino, 1-methyl-3-butoxyimino,
2-methyl-3-butoxyimino, 3-methyl-3-butoxyimino,
1,1-dimethyl-2-propoxyimino, 1,2-dimethyl-1-propoxyimino,
1,2-dimethyl-2-propoxyimino, 1-ethyl-1-propoxyimino,
1-ethyl-2-propoxyimino, n-hexoxyimino, 2-hexoxyimino,
3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino,
1-mEthyl-1-pentoxyimino, 2-methyl-1-pentoxyimino,

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3-methyl-1-pentoxyimino, 4-methyl-J.-pentoxyimino,
1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino,
3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino,
1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino,
3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino,
1-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino,
3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino,
1,1-dimethyl-2-butoxyimino, 1,1-dimethyl-3-butoxyimino,
1,2-dimethyl-1-butoxyimino, 1,2-dimethyl-2-butoxyimino,
1,2-dimethyl-3-butoxyimino, 1,3-dimethyl-1-butoxyimino,
1,3-dimethyl-2-butoxyimino, 1,3-dimethyl-3-butoxyimino,
2,2-dimethyl-3-butoxyimino, 2,3-dimethyl-1-butoxyimino,
2,3-dimethyl-2-butoxyimino, 2,3-dimethyl-3-butoxyimino,
3,3-dimethyl-1-butoxyimino, 3,3-dimethyl-2-butoxyimino,
1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino,
1-ethyl-3-butoxyimino, 2-ethyl-1-butoxyimino,
2-ethyl-2-butoxyimino, 2-ethyl-3-butoxyimino,
1,1,2-trimethyl-2-propoxyimino,
1-ethyl-1-methyl-2-propoxyimino,
1-ethyl-2-methyl-1-propoxyimino and
1-ethyl-2-methyl-2-propoxyimino, i.e., for example,
methoxyiminomethyl;
- C1-C6-alkoxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by
C1-C6-alkoxy as mentioned above, i.e., for example, CH2-OCH3,
CH2-OC2H5, n-propoxymethyl, CHZ-OCH(CHg)2, n-butoxymethyl,
(1-methylpropoxy)methyl, (2-methylpropoxy)methyl,
CHZ-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,
2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl,
2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl,
2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl,
2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl,
2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl,
2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,
2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl,
3-(ethoxy)propyl, 3-(n-propoxy)propyl,
3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl,
3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,
3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl,
2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl,
2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl,
2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl,
3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl,
3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl,
3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,
3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl,
4-(e-~hoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl,

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4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl,
4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, in
particular CH2-OCH3 or 2-methoxyethyl;
- di(C1-C6-alkoxy)-C1-C6-alkyl: for example 2,2-dimethoxyethyl
or 2,2-diethoxyethyl;
Ci-C6-alkoxy-C1-C6-alkoxy: C1-C6-alkoxy which is substituted
by C1-C6-alkoxy as mentioned above, i.e., for example,
OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)Z.
n-butoxymethoxy, (1-methylpropoxy)methoxy,
(2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-(methoxy)ethoxy,
2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy,
2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy,
2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,
2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy,
2-(ethoxy)propoxy, 2-(n-propoxy)propoxy,
2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy,
2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,
2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy,
3-(ethoxy)propoxy, 3-(n-propoxy)propoxy,
3-(1-methylethoxy)propoxy, 3-(n-butoxy)propoxy,
3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,
3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,
2-(ethoxy)butoxy, 2-(n-propoxy)butoxy,
2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy,
2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,
2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy,
3-(ethoxy)butoxy, 3-(n-propoxy)butoxy,
3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy,
3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,
3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy,
4-(ethoxy)butoxy, 4-(n-propoxy)butoxy,
4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy,
4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy,
4-(I,1-dimethylethoxy)butoxy, 5-(methoxy)pentoxy,
5-(ethoxy)pentoxy, 5-(n-propoxy)pentoxy,
5-(1-methylethoxy)pentoxy, 5-(n-butoxy)pentoxy,
5-(1-methylpropoxy)pentoxy, 5-(2-methylpropoxy)pentoxy,
5-(l,l-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy,
6-(ethoxy)hexoxy, 6-(n-propoxy)hexoxy,
6-(1-methylethoxy)hexoxy, 6-(n-butoxy)hexoxy,
6-(1-methylpropoxy)hexoxy, 6-(2-methylpropoxy)hexoxy or
6-(1,1-dimethylethoxy)hexoxy, in particular OCHZ-OCH3 or
OCHZ-OCZH5;

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34
- (C1-C6-alkyl)carbonyl-C1-C6-alkoxy: C1-C6-alkoxy which is
substituted by (C1-C6-alkyl)carbonyl as mentioned above, i.e.,
for example, OCHZ-CO-CH3, OCHz-CO-C2H5, OCH2-CO-CHZ-C2H5,
OCHz-CO-CH(CH3)Z, n-butylcarbonyl-methoxy, 1-(CO-CH3)ethoxy,
2-(CO-CH3)ethoxy, 2-(CO-C2H5)ethoxy, 2-(CO-CHZ-C2H5)ethoxy,
2-(n-butylcarbonyl)ethoxy, 3-(CO-CH3)propoxy,
3-(CO-C2H5)-propoxy, 3-(CO-CH2-CZH5)propoxy,
3-(n-butylcarbonyl)propoxy, 4-(CO-CH3)butoxy,
4-(CO-C2H5)butoxy, 4-(CO-CHZ-C2H5)butoxy,
4-(n-butylcarbonyl)butoxy, 5-(CO-CH3)pentoxy,
5-(CO-C2H5)pentoxy, 5-(CO-CH2-G2H5)pentoxy,
5-(n-butylcarbonyl)butoxy, 6-(CO-CH3)hexoxy,
6-(CO-C2H5)hexoxy, 6-(CO-CH2-CZH5)hexoxy or
6-(n-butylcarbonyl)hexoxy, in particular OCH2-CO-OCH3 or
1-(CO-CH3)ethoxy;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy: C1-C6-alkoxy which is
substituted by (C1-C6-alkoxy)carbonyl as mentioned above,
i.e., for example, OCH2-CO-OCH3, OCHZ-CO-OCZHS,
OCH2-CO-OCHZ-C2H5, OCH2-CO-OCH(CH3)2, n-butoxycarbonylmethoxy,
1-(methoxycarbonyl)ethoxy, 2-(methoxycarbonyl)ethoxy,
2-(ethoxycarbonyl)ethoxy, 2-(n-propoxycarbonyl)ethoxy,
2-(n-butoxycarbonyl)ethoxy, 3-(methoxycarbonyl)propoxy,
3-(ethoxycarbonyl)propoxy, 3-(n-propoxycarbonyl)propoxy,
3-(n-butoxycarbonyl)propoxy, 4-(methoxycarbonyl)butaxy,
4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy,
4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentoxy,
5-(ethoxycarbonyl)pentoxy, 5-(n-propoxycarbonyl)pentoxy,
5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexoxy,
6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or
6-(n-butoxycarbonyl)hexoxy, in particular OCHZ-CO-OCH3 or
1-(methoxycarbonyl)ethoxy;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkyl: C1-C6-alkyl which is
substituted by (C1-C6-alkoxy)carbonyl as mentioned above,
i.e., for example, methoxycarbonylmethyl,
ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl,
2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl,
3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl,
5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl:
C1-C6-alkylsulfonyl which is substituted by
(C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example,
methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl,
1-(methoxycarbonyl)ethylsulfonyl,
2-(meth~xycarbonyl)ethylsulfonyl, w

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2-(ethoxycarbonyl)ethylsulfonyl,
3-(methoxycarbonyl)propylsulfonyl,
4-(methoxycarbonyl)butylsulfonyl,
5-(methoxycarbonyl)pentylsulfonyl or
5 6-(methoxycarbonyl)hexylsulfonyl;
C1-C6-alkylthio-C1-C6-alkyl: C1-C6-alkyl which is substituted
by C1-C6-alkylthio as mentioned above, i.e., for example,
CH2-SCH3, CHZ-SC2H5, CH2-SCHZ-CyHS, CH2-SCH(CH3)2r
10 n-butylthiomethyl, CH2-SCH(CH3)-C2H5, CH2-SCH2-CH(CH3)2,
CH2-SC(CH3)3, 2-(SCH3)ethyl, 2-(SC2H5)ethyl,
2-(SCH2-C2H5)ethyl, 2-[SCH(CH3)2]ethyl, 2-(n-butylthio)ethyl,
2-[SCH(CH3)-CaH5]ethyl, 2-(2-methylpropylthio)ethyl,
2-[SC(CH3)3]ethyl, 2-(SCH3)propyl, 3-(SCH3)propyl,
15 2-(SCZH5)propyl, 3-(SCZHS)propyl, 3-(SCH2-C2H5)propyl,
3-(butylthio)propyl, 4-(SCH3)butyl, 4-(SC2H5)butyl,
4-(SCHZ-C2H5)butyl or 4-(n-butylthio)butyl, in particular
2-(SCH3)ethyl;
20 - C1-C6-alkylthio-C1-C6-alkoxy: C1-C6-alkoxy which is
substituted by C1-C6-alkylthio as mentioned above, i.e., for
example, OCHZ-SCH3, OCHZ-SC2H5, OCH2-SGH2-C2H5, OCHy-SCH(CH3)2.
n-butylthiomethoxy, OCH2-SCH(CH3)-CzHS, OCH2-SCH2-CH(CH3)2,
OCH2-SC(CH3)3, 2-(SCH3)ethoxy, 2-(SC2Hg)ethoxy,
25 2-(SCH2-CZH5)ethoxy, 2-[SCH(CH3)2]ethoxy,
2-(n-butylthio)ethoxy, 2-[SCH(CH3)-CZHS]ethoxy,
2-(2-methylpropylthio)ethoxy, 2-[SC(CH3)3]ethoxy,
2-(SCH3)propoxy, 3-(SCH3)propoxy, 2-(SC2H5)propoxy,
3-(SC2H5)propoxy, 3-(SCH2-C2H5)propoxy, 3-(butylthio)propoxy,
30 4-(SCH3)butoxy, 4-(SC2H5)butoxy, 4-(CH2-CyHS)butoxy or
4-(n-butylthio)butoxy, in particular 2-(SCH3)ethoxy;
- C1-C6-alkylthio-(C1-C6-alkyl)carbonyl: (C1-C6-alkyl)carbonyl
which is substituted by C1-C6-alkylthio as mentioned above,
35 preferably by SCH3 or SC2H5, i.e., for example,
methylthiomethylcarbonyl, ethylthiomethylcarbonyl,
1-(methylthio)ethylcarbonyl, 2-(methylthio)ethylcarbonyl,
3-(methylthio)propylcarbonyl, 4-(methylthio)butylcarbonyl,
5-(methylthio)pentylcarbonyl or 6-(methylthio)hexylcarbonyl,
in particular CO-CHz-SCH3 or CO-CH(CH3)-SCH3;
- di(C1-C6-alkyl)amino-C1-C6-alkoxy: C1-C6-alkoxy which is
substituted by di(C1-C6-alkyl)amino, such as N(CH3)2, N(C2H5)2,
N,N-dipropylamino, N,N-di(1-methylethyl)amino,
N,N-dibutylamino, N,N-di(1-methylpropyl)amino,
N,N-di(2-methylpropyl)amino, N[C(CH3)312.
Iv-ethyl-N-methylami~~a, N-methyl-N-propylamino, -'

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N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino,
N-methyl-N-(1-methylpropyl)amino,
N-methyl-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,
N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,
N-ethyl-N-(1-methylpropyl)amino,
N-ethyl-N-(2-methylpropyl)amino,
N-ethyl-N-(1,1-dimethylethyl)amino,
N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,
N-(1-methylpropyl)-N-propylamino,
N-(2-methylpropyl)-N-propylamino,
N-(1,1-dimethylethyl)-N-propylamino,
N-butyl-N-(1-methylethyl)amino,
N-(1-methylethyl)-N-(1-methylpropyl)amino,
N-(1-methylethyl)-N-(2-methylpropyl)amino,
N-(l,l-dimethylethyl)-N-(1-methylethyl)amino,
N-butyl-N-(1-methylpropyl)amino,
N-butyl-N-(2-methylpropyl)amino,
N-butyl-N-(1,1-dimethylethyl)amino,
N-(1-methylpropyl)-N-(2-methylpropyl)amino,
N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or
N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably by
N,N-dimethylamino or N,N-diethylamino, i.e., for example,
OCH2-N(CH3)2, OCHZ-N(C2H5)Z, OCH(CHg)-N(CH3)2,
2-(dimethylamino)ethoxy, OCH(CH3)-N(CZHS)2.
3-(dimethylamino)propoxy, 9-(dimethylamino)butoxy,
5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in
particular OCH2-N(CH3)Z or OCH(CH3)-N(CH3)2:
- C3-C6-alkenyl: for example prop-2-en-1-yl, n-buten-4-yl,
1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl,
n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-yl,
2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,
1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,
3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,
1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl,
n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl,
1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,
3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,
1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,
3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,
1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,
1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,
1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,
2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,
2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl;
1-ethylbut-2-en-1-yl, 1-ethylbut-3-en--1-yl,

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2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,
1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl
or 1-ethyl-2-methylprop-2-en-1-yl, in particular
prop-2-en-1-yl or n-buten-4-yl;
- C3-C6-haloalkenyl: C3-C6-alkenyl as mentioned above which is
partially or fully substituted by fluorine, chlorine and/or
bromine, i.e., for example, 2-chloroallyl, 3-chloroallyl,
2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl,
2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl,
2,3-dibromoallyl, 3,3-dibromallyl, 2,3,3-tribromoallyl or
2,3-dibromobut-2-enyl, in particular 2-chloroallyl or
3,3-dichloroallyl;
- C2-C6-alkenyl: ethenyl or one of the radicals mentioned under
C3-C6-alkenyl, in particular ethenyl or prop-2-en-1-yl;
- C3-C6-alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy,
1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy,
n-buten-3-yloxy, 1-methylprop-1-en-1-yloxy,
2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy,
2-methylprop-2-en-1-yloxy, n-penten-1-yloxy,
n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy,
1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,
3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,
2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,
1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,
3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,
1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,
1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy,
n-hex-1-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy,
n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy,
1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy,
3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,
1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,
3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,
1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,
3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,
1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,
3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,
1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,
1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,
1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy,
1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,
2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy,
2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,
3,3-dimethylbut-1-eu-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,

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1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,
1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy,
2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,
1,1,2-trimethylprop-2-en-1-yloxy,
1-ethyl-1-methylprop-2-en-1-yloxy,
1-ethyl-2-methylprop-1-en-1-yloxy or
1-ethyl-2-methylprop-2-en-1-yloxy, in particular
prop-2-en-1-yloxy;
- C2-C6-alkenyloxy: ethenyloxy or one of the radicals mentioned
under C3-C6-alkenyloxy, in particular ethenyloxy or
prop-2-en-1-yloxy;
- C3-C6-haloalkenyloxy: C3-C6-alkenyloxy as mentioned above
which is partially or fully substituted by fluorine, chlorine
and/or bromine, i.e., for example, 2-chloroallyloxy,
3-chloroallyloxy, 2,3-dichloroallyloxy, 3,3-dichloroallyloxy,
2,3,3-trichloroallyloxy, 2,3-dichlorobut-2-enyloxy,
2-bromoallyloxy, 3-bromoallyloxy, 2,3-dibromoallyloxy,
3,3-dibromoallyloxy, 2,3,3-tribromoallyloxy or
2,3-dibromobut-2-enyloxy, in particular 2-chloroallyloxy or
3,3-dichloroallyloxy;
- phenyl-C3-C6-alkenyloxy: for example 3-phenylallyloxy,
4-phenylbut-2-enyloxy, 4-phenylbut-3-enyloxy or
5-phenylpent-4-enyloxy, preferably 3-phenylallyloxy or
4-phenylbut-2-enyloxy, in particular 3-phenylallyloxy;
- heterocyclyl-C3-C6-alkenyloxy: for example
3-heterocyclylallyloxy, 4-heterocyclylbut-2-enyloxy,
4-heterocyclylbut-3-enyloxy or 5-heterocyclylpent-4-enyloxy,
preferably 3-heterocyclylallyloxy or
4-heterocyclylbut-2-enyloxy, in particular
3-heterocyclylallyloxy;
C2-C6-alkenylthio: ethenylthio, prop-1-en-1-ylthio,
prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio,
n-buten-2-ylthio, n-buten-3-ylthio,
1-methylprop-1-en-1-ylthio, 2-methylprop-1-en-1-ylthio,
1-methylprop-2-en-1-ylthio, 2-methylprop-2-en-1-ylthio,
n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio,
n-penten-4-ylthio, 1-methylbut-1-en-1-ylthio,
2-methylbut-1-en-1-ylthio, 3-methylbut-1-en-1-ylthio,
1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio,
3-methylbut-2-en-1-ylthio, 1-methylbut-3-en-1-ylthio,
~2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio,
1,1-dime-chylprop-2-en-1-ylthio,

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1,2-dimethylprop-1-en-1-ylthio,
1,2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio,
1-ethylprop-2-en-1-ylthio, n-hex-1-en-1-ylthio,
n-hex-2-en-1-ylthio, n-hex-3-en-1-ylthio,
n-hex-4-en-1-ylthio, n-hex-5-en-1-ylthio,
1-methylpent-1-en-1-ylthio, 2-methylpent-1-en-1-ylthio,
3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio,
1-methylpent-2-en-1-ylthio, 2-methylpent-2-en-1-ylthio,
3-methylpent-2-en-1-ylthio, 4-methylpent-2-en-1-ylthio,
1-methylpent-3-en-1-ylthio, 2-methylpent-3-en-1-ylthio,
3-methylpent-3-en-1-ylthio, 4-methylpent-3-en-1-ylthio,
1-methylpent-4-en-1-ylthio, 2-methylpent-4-en-1-ylthio,
3-methylpent-4-en-1-ylthio, 4-methylpent-4-en-1-ylthio,
1,1-dimethylbut-2-en-1-ylthio, 1,1-dimethylbut-3-en-1-ylthio,
1,2-dimethylbut-1-en-1-ylthio, 1,2-dimethylbut-2-en-1-ylthio,
1,2-dimethylbut-3-en-1-ylthio, 1,3-dimethylbut-1-en-1-ylthio,
1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio,
2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethylbut-1-en-1-ylthio,
2,3-dimethylbut-2-en-1-ylthio, 2,3-dimethylbut-3-en-1-ylthio,
3,3-dimethylbut-1-en-1-ylthio, 3,3-dimethylbut-2-en-1-ylthio,
1-ethylbut-1-en-1-ylthio, 1-ethylbut-2-en-1-ylthio,
1-ethylbut-3-en-1-ylthio, 2-ethylbut-1-en-1-ylthio,
2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio,
1,1,2-trimethylprop-2-en-1-ylthio,
1-ethyl-1-methylprop-2-en-1-ylthio,
1-ethyl-2-methylprop-1-en-1-ylthio or
1-ethyl-2-methylprop-2-en-1-ylthio, in particular ethenylthio
or prop-2-en-1-ylthio;
- C3-C6-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl,
n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl,
n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-I-yn-3-yl,
n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,
n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,
3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,
n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl,
n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl,
n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl,
3-methylpent-I-yn-1-yl, 3-methylpent-1-yn-3-yl,
3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl,
4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or
4-methylpent-2-yn-5-yl, in particular prop-2-yn-1-yl;
- CZ-C6-alkynyl: ethynyl or one of the radicals mentioned under
C3-C6-alkynyl, in particular ethynyl or prop-2-yn-1-yl;

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C3-C6-alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy,
n-but-1-yn-I-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy,
n-but-2-yn-1-yloxy, n-pent-1-yn-I-yloxy, n-pent-1-yn-3-yloxy,
n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy,
5 n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy,
n-pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy,
3-methylbut-1-yn-4-yloxy, n-hex-1-yn-1-yloxy,
n-hex-1-yn-3-yloxy, n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy,.
n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy,
10 n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy,
n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy,
3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy,
3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy,
4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy, in
15 particular prop-2-yn-1-yloxy;
- C2-C6-alkynyloxy: ethynyloxy or one of the radicals mentioned
under C3-C6-alkynyloxy, in particular ethynyloxy or
prop-2-yn-1-yloxy;
- phenyl-C3-C6-alkynyloxy: for example
3-phenylprop-2-yn-1-yloxy, 4-phenylbut-2-yn-1-yloxy,
3-phenylbut-3-yn-2-yloxy, 5-phenylpent-3-yn-1-yloxy or
6-phenylhex-4-yn-1-yloxy, in particular
3-phenylprop-2-yn-1-yloxy or 3-phenylbut-3-yn-2-yloxy;
- heterocyclyl-C3-C6-alkynyloxy: for example
3-(heterocyclyl)prop-2-yn-1-yloxy,
4-(heterocyclyl)but-2-yn-I-yloxy,
3-(heterocyclyl)but-3-yn-2-yloxy,
5-(heterocyclyl)pent-3-yn-1-yloxy or
6-(heterocyclyl)hex-4-yn-1-yloxy, in particular
3-(heterocyclyl)prop-2-yn-1-yloxy or 3-(heterocyclyl)but-
3-yn-2-yloxy;
- C3-C6-alkynylthio: prop-1-yn-1-ylthio, prop-2-yn-1-ylthio,
n-but-1-yn-1-ylthio, n-but-1-yn-3-ylthio,
n-but-1-yn-4-ylthio, n-but-2-yn-1-ylthio,
n-pent-1-yn-1-ylthio, n-pent-1-yn-3-ylthio,
n-pent-1-yn-4-ylthio, n-pent-1-yn-5-ylthio,
n-pent-2-yn-1-ylthio, n-pent-2-yn-4-ylthio,
n-pent-2-yn-5-ylthio, 3-methylbut-1-yn-3-ylthio,
3-methylbut-1-yn-4-ylthio, n-hex-1-yn-1-ylthio,
n-hex-1-yn-3-ylthio, n-hex-1-yn-4-ylthio,
n-hex-1-yn-5-ylthio, n-hex-1-yn-6-ylthio,
n-hex-2-yn-1-ylthio, n-hex-2-yn-4-ylthio,
n-hex-2-yn-5-ylthio, n-hex-2-yn-6-ylthio,

CA 02377143 2001-12-19
41
n-hex-3-yn-1-ylthio, n-hex-3-yn-2-ylthio,
3-methylpent-1-yn-1-ylthio, 3-methylpent-1-yn-3-ylthio,
3-methylpent-1-yn-4-ylthio, 3-methylpent-1-yn-5-ylthio,
4-methylpent-1-yn-1-ylthio, 4-methylpent-2-yn-4-ylthio or
4-methylpent-2-yn-5-ylthio, in particular prop-2-yn-1-ylthio;
- C2-C6-alkynylthio: ethynylthio or one of the radicals
mentioned under C3-C6-alkynylthio, in particular ethynylthio
or prop-2-yn-1-ylthio;
- (C3-C6-alkenyloxy)carbonyl: prop-1-en-1-yloxycarbonyl,
prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl,
n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl,
n-buten-3-yloxycarbonyl, 1-methylprop-1-en-1-yloxycarbonyl,
2-methylprop-1-en-1-yloxycarbonyl,
1-methylprop-2-en-1-yloxycarbonyl,
2-methylprop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl,
n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl,
n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-yloxycarbonyl,
2-methylbut-1-en-1-yloxycarbonyl,
3-methylbut-1-en-1-yloxycarbonyl,
1-methylbut-2-en-1-yloxycarbonyl,
2-methylbut-2-en-1-yloxycarbonyl,
3-methylbut-2-en-1-yloxycarbonyl,
1-methylbut-3-en-1-yloxycarbonyl,
2-methylbut-3-en-1-yloxycarbonyl,
3-methylbut-3-en-1-yloxycarbonyl,
l,l-dimethylprop-2-en-1-yloxycarbonyl,
1,2-dimethylprop-1-en-1-yloxycarbonyl,
1,2-dimethylprop-2-en-1-yloxycarbonyl,
1-ethylprop-1-en-2-yloxycarbonyl,
1-ethylprop-2-en-1-yloxycarbonyl, n-hex-1-en-1-yloxycarbonyl,
n-hex-2-en-1-yloxycarbonyl, n-hex-3-en-1-yloxycarbonyl,
n-hex-4-en-1-yloxycarbonyl, n-hex-5-en-1-yloxycarbonyl,
1-methylpent-1-en-1-yloxycarbonyl,
2-methylpent-1-en-1-yloxycarbonyl,
3-methylpent-1-en-1-yloxycarbonyl,
4-methylpent-1-en-1-yloxycarbonyl,
1-methylpent-2-en-1-yloxycarbonyl,
2-methylpent-2-en-1-yloxycarbonyl,
3-methylpent-2-en-1-yloxycarbonyl,
4-methylpent-2-en-1-yloxycarbonyl,
1-methylpent-3-en-1-yloxycarbonyl,
2-methylpent-3-en-1-yloxycarbonyl,
3-methylpent-3-en-1-yloxycarbonyl,
4-methylpent-3-en-1-yloxycarbonyl,
1-methj~lpent-4-erg-1-yloxycarbonyl, ' '

0050~5~0$0 CA 02377143 2001-12-19
42
2-methylpent-4-en-1-yloxycarbonyl,
3-methylpent-4-en-1-yloxycarbonyl,
4-methylpent-4-en-1-yloxycarbonyl,
1,1-dimethylbut-2-en-1-yloxycarbonyl,
1,1-dimethylbut-3-en-1-yloxycarbonyl,
1,2-dimethylbut-1-en-1-yloxycarbonyl,
1,2-dimethylbut-2-en-1-yloxycarbonyl,
1,2-dimethylbut-3-en-1-yloxycarbonyl,
1,3-dimethylbut-1-en-1-yloxycarbonyl,
1,3-dimethylbut-2-en-1-yloxycarbonyl,
1,3-dimethylbut-3-en-1-yloxycarbonyl,
2,2-dimethylbut-3-en-1-yloxycarbonyl,
2,3-dimethylbut-1-en-1-yloxycarbonyl,
2,3-dimethylbut-2-en-1-yloxycarbonyl,
2,3-dimethylbut-3-en-1-yloxycarbonyl,
3,3-dimethylbut-1-en-1-yloxycarbonyl,
3,3-dimethylbut-2-en-1-yloxycarbonyl,
1-ethylbut-1-en-1-yloxycarbonyl,
1-ethylbut-2-en-1-yloxycarbonyl,
1-ethylbut-3-en-1-yloxycarbonyl,
2-ethylbut-1-en-1-yloxycarbonyl,
2-ethylbut-2-en-1-yloxycarbonyl,
2-ethylbut-3-en-1-yloxycarbonyl,
1,1,2-trimethylprop-2-en-1-yloxycarbonyl,
1-ethyl-1-methylprop-2-en-1-yloxycarbonyl,
1-ethyl-2-methylprop-1-en-1-yloxycarbonyl or
1-ethyl-2-methylprop-2-en-1-yloxycarbonyl, in particular
prop-2-en-1-yloxycarbonyl;
- (C3-C6-alkenyloxy)carbonyl-C1-C6-alkyl: C1-C6-alkyl which is
substituted by (C3-C6-alkenyloxy)carbonyl as mentioned above,
preferably by prop-2-en-1-yl-oxycarbonyl, i.e., for example,
prop-2-en-1-yl-oxycarbonylmethyl;
- (CZ-C6-alkenyl)carbonyloxy: ethenylcarbonyloxy,
prop-1-en-1-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy,
1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy,
n-buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy,
1-methylprop-1-en-1-ylcarbonyloxy,
2-methylprop-1-en-1-ylcarbonyloxy,
1-methylprop-2-en-1-ylcarbonyloxy,
2-methylprop-2-en-1-ylcarbonyloxy, n-penten-1-ylcarbonyloxy,
n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy,
n-penten-4-ylcarbonyloxy, 1-methylbut-1-en-1-ylcarbonyloxy,
2-methylbut-1-en-1-ylcarbonyloxy,
3-methylbut-1-en-1-ylcarbonyloxy,
1-methylbui:-2-en-1-ylcarbo~iyloxy,

CA 02377143 2001-12-19
43
2-methylbut-2-en-1-ylcarbonyloxy,
3-methylbut-2-en-1-ylcarbonyloxy,
1-methylbut-3-en-1-ylcarbonyloxy,
2-methylbut-3-en-1-ylcarbonyloxy,
3-methylbut-3-en-1-ylcarbonyloxy,
1,1-dimethylprop-2-en-1-ylcarbonyloxy,
1,2-dimethylprop-1-en-1-ylcarbonyloxy,
1,2-dimethylprop-2-en-1-ylcarbonyloxy,
1-ethylprop-1-en-2-ylcarbonyloxy,
1-ethylprop-2-en-1-ylcarbonyloxy, n-hex-1-en-1-ylcarbonyloxy,
n-hex-2-en-1-ylcarbonyloxy, n-hex-3-en-I-ylcarbonyloxy,
n-hex-4-en-1-ylcarbonyloxy, n-hex-5-en-1-ylcarbonyloxy,
1-methylpent-1-en-I-ylcarbonyloxy,
2-methylpent-1-en-1-ylcarbonyloxy,
3-methylpent-1-en-1-ylcarbonyloxy,
4-methylpent-1-en-1-ylcarbonyloxy,
1-methylpent-2-en-1-ylcarbonyloxy,
2-methylpent-2-en-1-ylcarbonyloxy,
3-methylpent-2-en-1-ylcarbonyloxy,
4-methylpent-2-en-1-ylcarbonyloxy,
1-methylpent-3-en-1-ylcarbonyloxy,
2-methylpent-3-en-1-ylcarbonyloxy,
3-methylpent-3-en-1-ylcarbonyloxy,
4-methylpent-3-en-1-ylcarbonyloxy,
1-methylpent-4-en-1-ylcarbonyloxy,
2-methylpent-4-en-1-ylcarbonyloxy,
3-methylpent-4-en-1-ylcarbonyloxy,
4-methylpent-4-en-1-ylcarbonyloxy,
1,1-dimethylbut-2-en-1-ylcarbonyloxy,
1,1-dimethylbut-3-en-1-ylcarbonyloxy,
1,2-dimethylbut-1-en-1-ylcarbonyloxy,
1,2-dimethylbut-2-en-1-ylcarbonyloxy,
1,2-dimethylbut-3-en-1-ylcarbonyloxy,
1,3-dimethylbut-1-en-1-ylcarbonyloxy,
1,3-dimethylbut-2-en-1-ylcarbonyloxy,
1,3-dimethylbut-3-en-1-ylcarbonyloxy,
2,2-dimethylbut-3-en-1-ylcarbonyloxy,
2,3-dimethylbut-1-en-1-ylcarbonyloxy,
2,3-dimethylbut-2-en-1-ylcarbonyloxy,
2,3-dimethylbut-3-en-1-ylcarbonyloxy,
3,3-dimethylbut-1-en-1-ylcarbonyloxy,
3,3-dimethylbut-2-en-1-ylcarbonyloxy,
1-ethylbut-1-en-1-ylcarbonyloxy,
1-ethylbut-2-en-1-ylcarbonyloxy,
1-ethylbut-3-en-1-ylcarbonyloxy,
2-ethylbut-1-en-1-ylcarbonyloxy,
2-ethylbut-2-en-1-ylcdrbon;~loxy,

0050/50080 CA 02377143 2001-12-19
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2-ethylbut-3-en-1-ylcarbonyloxy,
1,1,2-trimethylprop-2-en-1-ylcarbonyloxy,
1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy,
1-ethyl-2-methylprop-1-en-1-ylcarbonyloxy or
1-ethyl-2-methylprop-2-en-1-ylcarbonyloxy, in particular
ethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy;
- (CZ-C6-alkenyl)carbonylthio: ethenylcarbonylthio,
prop-1-en-1-ylcarbonylthio, prop-2-en-1-ylcarbonylthio,
1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio,
n-buten-2-ylcarbonylthio, n-buten-3-ylcarbonylthio,
1-methylprop-1-en-1-ylcarbonylthio,
2-methylprop-1-en-1-ylcarbonylthio,
1-methylprop-2-en-1-ylcarbonylthio,
2-methylprop-2-en-1-ylcarbonylthio,
n-penten-1-ylcarbonylthio, n-penten-2-ylcarbonylthio,
n-penten-3-ylcarbonylthio, n-penten-4-ylcarbonylthio,
1-methylbut-1-en-1-ylcarbonylthio,
2-methylbut-1-en-1-ylcarbonylthio,
3-methylbut-1-en-1-ylcarbonylthio,
1-methylbut-2-en-1-ylcarbonylthio,
2-rnethylbut-2-en-1-ylcarbonylthio,
3-methylbut-2-en-1-ylcarbonylthio,
1-methylbut-3-en-1-ylcarbonylthio,
2-methylbut-3-en-1-ylcarbonylthio,
3-methylbut-3-en-1-ylcarbonylthio,
1,1-dimethylprop-2-en-1-ylcarbonylthio,
1,2-dimethylprop-1-en-1-ylcarbonylthio,
1,2-dimethylprop-2-en-1-ylcarbonylthio,
1-ethylprop-1-en-2-ylcarbonylthio,
1-ethylprop-2-en-1-ylcarbonylthio,
n-hex-1-en-1-ylcarbonylthio, n-hex-2-en-1-ylcarbonylthio,
n-hex-3-en-1-ylcarbonylthio, n-hex-4-en-1-ylcarbonylthio,
n-hex-5-en-1-ylcarbonylthio,
1-methylpent-1-en-1-ylcarbonylthio,
2-methylpent-1-en-1-ylcarbonylthio,
3-methylpent-1-en-1-ylcarbonylthio,
4-methylpent-1-en-1-ylcarbonylthio,
1-methylpent-2-en-1-ylcarbonylthio,
2-methylpent-2-en-1-ylcarbonylthio,
3-methylpent-2-en-1-ylcarbonylthio,
4-methylpent-2-en-1-ylcarbonylthio,
1-methylpent-3-en-1-ylcarbonylthio,
2-methylpent-3-en-1-ylcarbonylthio,
3-methylpent-3-en-1-ylcarbonylthio,
4-methylpent-3-en-1-ylcarbonylthio,
1-methylYent-4-en-1-ylcarbonyltiiio,- rw

005050080 CA 02377143 2001-12-19
2-methylpent-4-en-1-ylcarbonylthio,
3-methylpent-4-en-1-ylcarbonylthio,
4-methylpent-4-en-1-ylcarbonylthio,
1,1-dimethylbut-2-en-1-ylcarbonylthio,
5 1,1-dimethylbut-3-en-1-ylcarbonylthio,
1,2-dimethylbut-1-en-1-ylcarbonylthio,
1,2-dimethylbut-2-en-1-ylcarbonylthio,
1,2-dimethylbut-3-en-1-ylcarbonylthio,
1,3-dimethylbut-1-en-1-ylcarbonylthio,
10 1,3-dimethylbut-2-en-1-ylcarbonylthio,
1,3-dimethylbut-3-en-1-ylcarbonylthio,
2,2-dimethylbut-3-en-1-ylcarbonylthio,
2,3-dimethylbut-1-en-1-ylcarbonylthio,
2,3-dimethylbut-2-en-1-ylcarbonylthio,
15 2,3-dimethylbut-3-en-1-ylcarbonylthio,
3,3-dimethylbut-1-en-1-ylcarbonylthio,
3,3-dimethylbut-2-en-1-ylcarbonylthio,
1-ethylbut-1-en-1-ylcarbonylthio, 1-ethylbut-
2-en-1-ylcarbonylthio, 1-ethylbut-3-en-1-ylcarbonylthio,
20 2-ethylbut-1-en-1-ylcarbonylthio,
2-ethylbut-2-en-1-ylcarbonylthio,
2-ethylbut-3-en-1-ylcarbonylthio,
1,1,2-trimethylprop-2-en-1-ylcarbonylthio,
1-ethyl-1-methylprop-2-en-1-ylcarbonylthio,
25 1-ethyl-2-methylprop-1-en-1-ylcarbonylthio or
1-ethyl-2-methylprop-2-en-1-ylcarbonylthio, in particular
ethenylcarbonylthio or prop-2-en-1-ylcarbonylthio;
- (CZ-C6-alkynyl)carbonyloxy: ethynylcarbonyloxy,
30 prop-1-yn-1-ylcarbonyloxy, prop-2-yn-1-ylcarbonyloxy,
n-but-1-yn-1-ylcarbonyloxy, n-but-1-yn-3-ylcarbonyloxy,
n-but-1-yn-4-ylcarbonyloxy, n-but-2-yn-1-ylcarbonyloxy,
n-pent-1-yn-1-ylcarbonyloxy, n-pent-1-yn-3-ylcarbonyloxy,
n-pent-1-yn-4-ylcarbonyloxy, n-pent-1-yn-5-ylcarbonyloxy,
35 n-pent-2-yn-1-ylcarbonyloxy, n-pent-2-yn-4-ylcarbonyloxy,
n-pent-2-yn-5-ylcarbonyloxy,
3-methylbut-1-yn-3-ylcarbonyloxy,
3-methylbut-1-yn-4-ylcarbonyloxy, n-hex-1-yn-1-ylcarbonyloxy,
n-hex-1-yn-3-ylcarbonyloxy, n-hex-1-yn-4-ylcarbonyloxy,
40 n-hex-1-yn-5-ylcarbonyloxy, n-hex-1-yn-6-ylcarbanyloxy,
n-hex-2-yn-1-ylcarbonyloxy, n-hex-2-yn-4-ylcarbonyloxy,
n-hex-2-yn-5-ylcarbonyloxy, n-hex-2-yn-6-ylcarbonyloxy,
n-hex-3-yn-1-ylcarbonyloxy, n-hex-3-yn-2-ylcarbonyloxy,
3-methylpent-1-yn-1-ylcarbonyloxy,
45 3-methylpent-1-yn-3-ylcarbonyloxy,
3-methylpent-1-yn-4-ylcarbonyloxy,.
3-methylpent-1-yn-5-ylcarbonyloxy,

CA 02377143 2001-12-19
0050/50080
46
4-methylpent-1-yn-1-ylcarbonyloxy,
4-methylpent-2-yn-4-ylcarbonyloxy or
4-methylpent-2-yn-5-ylcarbonyloxy, in particular
ethynylcarbonyloxy or prop-2-yn-1-ylcarbonyloxy;
_ C3-C6-alkynylsulfonyloxy: prop-1-yn-1-ylsulfonyloxy,
prop-2-yn-1-ylsulfonyloxy, n-but-1-yn-1-ylsulfonyloxy,
n-but-1-yn-3-ylsulfonyloxy, n-but-1-yn-4-ylsulfonyloxy,
n-but-2-yn-1-ylsulfonyloxy, n-pent-1-yn-1-ylsulfonyloxy,
n-pent-1-yn-3-ylsulfonyloxy, n-pent-1-yn-4-ylsulfonyloxy,
n-pent-1-yn-5-ylsulfonyloxy, n-pent-2-yn-1-ylsulfonyloxy,
n-pent-2-yn-4-ylsulfonyloxy, n-pent-2-yn-5-ylsulfonyloxy,
3-methylbut-1-yn-3-ylsulfonyloxy,
3-methylbut-1-yn-4-ylsulfonyloxy, n-hex-1-yn-1-ylsulfonyloxy,
n-hex-1-yn-3-ylsulfonyloxy, n-hex-1-yn-4-ylsulfonyloxy,
n-hex-1-yn-5-ylsulfonyloxy, n-hex-1-yn-6-ylsulfonyloxy,
n-hex-2-yn-1-ylsulfonyloxy, n-hex-2-yn-4-ylsulfonyloxy,
n-hex-2-yn-5-ylsulfonyloxy, n-hex-2-yn-6-ylsulfonyloxy,
n-hex-3-yn-1-ylsulfonyloxy, n-hex-3-yn-2-ylsulfonyloxy,
3-methylpent-1-yn-1-ylsulfonyloxy,
3-methylpent-1-yn-3-ylsulfonyloxy,
3-methylpent-1-yn-4-ylsulfonyloxy,
3-methylpent-1-yn-5-ylsulfonyloxy,
4-methylpent-1-yn-1-y.lsulfonyloxy,
4-methylpent-2-yn-4-ylsulfonyloxy or
4-methylpent-2-yn-5-ylsulfonyloxy, in particular
prop-2-yn-1-ylsulfonyloxy;
_ (Cz-C6-alkynyl)carbonylthio: ethynylcarbonylthio,
prop-1-yn-1-ylcarbonylthio, prop-2-yn-1-ylcarbonylthio,
n-but-1-yn-1-ylcarbonylthio, n-but-1-yn-3-ylcarbonylthio,
n-but-1-yn-4-ylcarbonylthio, n-but-2-yn-1-ylcarbonylthio,
n-pent-1-yn-1-ylcarbonylthio, n-pent-1-yn-3-ylcarbonylthio,
n-pent-1-yn-4-ylcarbonylthio, n-pent-1-yn-5-ylcarbonylthio,
n-pent-2-yn-1-ylcarbonylthio, n-pent-2-yn-4-ylcarbonylthio,
n-pent-2-yn-5-ylcarbonylthio,
3-methylbut-1-yn-3-ylcarbonylthio,
3-methylbut-1-yn-4-ylcarbonylthio,
n-hex-1-yn-1-ylcarbonylthio, n-hex-1-yn-3-ylcarbonylthio,
n-hex-1-yn-4-ylcarbonylthio, n-hex-1-yn-5-ylcarbonylthio,
n-hex-1-yn-6-ylcarbonylthio, n-hex-2-yn-1-ylcarbonylthio,
n-hex-2-yn-4-ylcarbonylthio, n-hex-2-yn-5-ylcarbonylthio,
n-hex-2-yn-6-ylcarbonylthio, n-hex-3-yn-1-ylcarbonylthio,
n-hex-3-yn-2-ylcarbonylthio,
3-methylpent-1-yn-1-ylcarbonylthio,
3-methylpent-1-yn-3-ylcarbonylthio, -.
3-methylpent-I-yn-4-ylcarbonylthio, '

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3-methylpent-1-yn-5-ylcarbonylthio,
4-methylpent-1-yn-1-ylcarbonylthio,
4-methylpent-2-yn-4-ylcarbonylthio or
4-methylpent-2-yn-5-ylcarbonylthio, in particular
prop-2-yn-1-ylcarbonylthio;
- (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl: C2-C6-alkenyl which is
substituted by (C1-C6-alkoxy)carbonyl as mentioned above,
i.e., for example, methoxycarbonylprop-2-en-1-y.l;
15
- (C1-C6-alkoxy)carbonyl-C2-C6-alkenyloxy: C2-C6-alkenyloxy
which is substituted by (C1-C6-alkoxy)carbonyl as mentioned
above, i.e., for example, 1-methoxycarbonylethen-1-yloxy and
methoxycarbonylprop-2-en-1-yloxy;
- C1-C6-alkoxy-C3-C6-alkenyloxy: C3-C6-alkenyloxy which is
substituted by C1-C6-alkoxy as mentioned above, i.e., for
example, methylprop-2-en-1-yloxy;
- C3-C6-alkenyloxy-C1-C6-alkyl: C1-C6-alkyl which is substituted
by C3-C6-alkenyloxy as mentioned above, preferably allyloxy,
2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy
or but-2-en-1-yloxy, i.e., for example, allyloxymethyl,
2-allyloxyethyl or but-1-en-4-yloxymethyl;
C3-C6-alkynyloxy-G1-C6-alkyl: C1-C6-alkyl which is substituted
by C3-C6-alkynyloxy as mentioned above, preferably
propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy or
but-2-yn-1-yloxy, i.e., for example, propargyloxymethyl or
2-propargyloxyethyl;
- C3-C6-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or
cyclohexyl;
- C3-C6-cycloalkyl-C1-C6-alkoxy: for example cyclopropylmethoxy,
cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy,
1-(cyclopropyl)ethoxy, 1-(cyclobutyl)ethoxy,
1-(cyclopentyl)ethoxy, 1-(cyclohexyl)ethoxy,
2-(cyclopropyl)ethoxy, 2-(cyclobutyl)ethoxy,
2-(cyclopentyl)ethoxy, 2-(cyclohexyl)ethoxy,
3-(cyclopropyl)propoxy, 3-(cyclobutyl)propoxy,
3-(cyclopentyl)propoxy, 3-(cyclohexyl)propoxy,
4-(cyclopropyl)butoxy, 4-(cyclobutyl)butoxy,
4-(cyclopentyl)butoxy, 4-(cyclohexyl)butoxy,
5-(cyclopropyl)pentoxy, 5-(cyclobutyl)pentoxy,
5-(cyclopentyl)pentoxy, 5-(cyclohexyl)pentoxy,
6-(cyclopropyl)hexoAy, 6-(cyclobutyl)hexoxy,

0050/50080
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48
6-(cyclopentyl)hexoxy or 6-(cyclohexyl)hexoxy, in particular
cyclopentylmethoxy or cyclohexylmethoxy;
- C3-C6-cycloalkyloxy: cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy or cyclohexyloxy;
- C3-C6-cycloalkylthio: cyclopropylthio, cyclobutylthio,
cyclopentylthio or cyclohexylthio;
- C3-C6-cycloalkylcarbonyloxy: cyclopropylcarbonyloxy,
cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or
cyclohexylcarbonyloxy;
- C3-C6-cycloalkylsulfonyloxy: cyclopropylsulfonyloxy,
cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or
cyclohexylsulfonyloxy;
- C5-C7-cycloalkenyloxy: cyclopent-1-enyloxy,
cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy,
cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1-enyloxy,
cyclohept-2-enyloxy, cyclohept-3-enyloxy or
cyclohept-4-enyloxy.
3- to 7-membered azaheterocycles which, in addition to carbon
ring members, may also comprise, as a ring member, an oxygen or
sulfur atom are, for example, pyrrolidin-1-yl, isoxazolidin-2-yl,
isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl,
piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and
azepin-1-yl.
3- to 7-membered heterocyclyl, which can be linked directly or
via an oxygen, alkoxy, alkenyloxy or alkynyloxy bridge, is to be
understood as meaning not only saturated, partially or fully
unsaturated, but also aromatic heterocycles having one to three
heteroatoms selected from a group consisting of
- one to three nitrogen atoms,
- one or two oxygen atoms and
- one or two sulfur atoms.
Examples of saturated heterocycles which can contain a carbonyl
or thiocarbonyl ring member are:
oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl,
diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl,
thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl,
azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,
tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl,
pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, w

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1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl,
1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl,
1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl,
1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl,
1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,
pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl,
tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl,
tetrahydropyrazol-4-yl, tetrahydropyran-2-yl,
tetrahydropyran-3-yl, tetrahydropyran-4-yl,
tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,
tetrahydrothiopyran-4-yl, piperidin-1-yl, piperidin-2-yl,
piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl,
1,3-dioxan-5-yl, 1,4-dioxan-2-y1, 1,3-oxathian-2-yl,
1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl,
1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl,
morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl,
hexahydropyridazin-3-yl, hexahydropyridazin-4-yl,
hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl,
hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl,
piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl,
hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl,
oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl,
1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl,
1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl,
1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl,
1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl,
hexahydroazepin-3-yl, hexahydroazepin-4-yl,
hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl,
hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and
hexahydro-1,4-diazepin-2-yl.
Examples of unsaturated heterocycles which can contain a carbonyl
or thiocarbonyl ring member are:
dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl,
1,3-oxazolin-2-yl.
Preferred amongst the heteroaromatic compounds are those with 5
and 6 members, i.e., for example
furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl
and 3-thienyl, pyrralyl, such as 2-pyrrolyl and 3-pyrrolyl,
isoxazolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl,
isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and
5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and
5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and
5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyl and
5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl,
oxadiazolyi, such as 1,2,4-oxadiazol-3-yi, 1,2,4-oxadiazol-5-yl~-

0050/50080
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and 1,3,4-oxadiazol-2-yl, thiadiazolyl, such as
1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and
1,3,4-thiadiazol-2-yl, triazolyl, such as 1,2,4-triazol-1-yl,
1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as
5 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as
3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as
2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore
2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in
particular pyridyl, pyrimidyl, furanyl and thienyl.
With a view to the use of the substituted ureas of the formulae
Ia and Ib according to the invention as herbicides, the variables
preferably have the following meanings, in each case on their own
or in combination:
Z is O or S
RA is C02R1, halogen, cyano, OR2 or C1-C3-alkyl;
Q is Q1. Qz or Q4.
X, Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O or S;
R is hydrogen, C(O)OR1~, C(O)SR1~, C(S)OR1~, C(S)SR1~, CHO,
CN, C(O)R2, C(O)NR11R12, C(S)NR11R1z, C(0)NHC(O)OR12~,
C(O)NHS(O)2R12~, C(O)NHS(O)yORl2~;
R1 is hydrogen or C1-C3-alkyl;
R2 is C1-C3-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C3-haloalkyl,
C1-C3-alkoxycarbonyl-C1-C3-alkyl, cyano-C1-C3-alkyl,
benzyl, which may be substituted by halogen, C1-C4-alkyl
or trifluoromethyl, or
is phenyl, which may be substituted by halogen,
C1-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
R3 is hydrogen, fluorine or chlorine;
R4 is chlorine, trifluoromethyl or cyano;

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51
R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen,
Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-haloalkoxy,
Ci-C6-haloalkylthio, Ci-C6-alkoxy-(C1-C6-alkyl)carbonyl,
Ci-C6-alkylthio-(Ci-C6-alkyl)carbonyl,
(Ci-C6-alkyl)iminooxycarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl,
Ci-C6-alkoxyamino-Ci-C6-alkyl,
Ci-C6-alkoxy-Ci-C6-alkylamino-Ci-C6-alkyl,
is Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C6-cycloalkoxy,
C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio,
C2-C6-alkynyloxy, C2-C6-alkynylthio,
(Ci-C6-alkyl)carbonyloxy, (Ci-C6-alkyl)carbonylthio,
(Ci-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy,
(C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy,
(C2-C6-alkynyl)carbonylthio, Ci-C6-alkylsulfonyloxy or
Ci-C6-alkylsulfonyl, where each of these 17 radicals may,
if desired, carry one, two or three substituents,
selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl,
Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy,
Ci-C6-alkylthio, Ci-C6-alkylsulfinyl,
Ci-C6-alkylsulfonyl, Ci-C6-alkylideneaminooxy, oxo,
=N-OR13
- phenyl, phenoxy or phenylsulfonyl, where the three
last-mentioned substituents may for their part carry
one, two or three substituents, in each case selected
from the group consisting of halogen, nitro, cyano,
Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and
(Ci-C6-alkoxy)carbonyl;
_ _CO_R14~ -CO_OR14, -CO-SR14, -CO-N(R14)-R15~ _pC0-R14,
-OCO-OR14' , -OCO-SR14' , -OCO-N ( R14 ) -R15 ~ _N ( R14 ) _R15 ~
and -C(Ri6)=N-OR13;
is C(Zi)-R17, -C(=NRi~)Ri7, C(R17) (Z2R19) (Z3R2o) ~
G ( R17 ) cc ( R21 ) _CN, f ( Ri 7 ) =G ( R21 ) _Gp_R22 ~
-CH(Ri7)-CH(R21)-COR22, -C(Ri7)=C(R21)_CHZ_CO_R22~
_G(R17)=G(R21)_G(R23)=G(R24)_GO_R22~
-G(Ri7)=C(R21)-CHZ_CH(R25)-CO_R22, -CO_OR26, -CO-SR26,
-CON(R26)-OR13~ _C~C-CO-NHORi3, -CSC-CO-N(R26)-OR13,
-G5C-CS-NH-OR13, -CSC-CS-N(R26)-OR13,
-C(R17)=C(R21)_CO-NHOR13, -C(R17)=C(R21)_CO_N(R26)_pRi3,
-G(R17)=G(R21)_Gg_NHOR13, -C(R17)=G(R21)_Gc~_N(R26)-pRi3,
-G ( R17 ) =G ( R21 ) -G ( R16 ) =N-OR13 ~ G ( R16 ) =N-GR13 ~ ,.

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0050/50080
52
-CSC-C(R16)=NOR13, C(z2R19)(Z3R2o)-pR26,
-C(Z2R19)(Z2R20)SR26, C(22R19)(Z3R20)-N(R27)R28~ -N(R27)-R28~
-CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; in which Z1.
Z2, Z3 independently of one another are oxygen or sulfur;
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C3-C7-cycloalkyl, or is 3- to 7-membered
saturated heterocyclyl which contains one or more oxygen
and/or sulfur atoms;
R7 is hydrogen or C1-C6-alkyl;
R8 is hydrogen or Ci-C3-alkyl;
R9 is hydrogen, C1-C3-alkyl
Re and R9 together are C=O;
Rlo is C1-C15-alkyl, C3-C8-cycloalkyl, C2-Clo-alkenyl,
Cs-Clo-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C3-C6-alkenyloxy-C1-C6-alkyl,
C3-C6-alkynyloxy-C1-C6-alkyl, cyano-C1-C6-alkyl,
is phenyl or benzyl which may in each case be mono- to
pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl,
C1-C4-alkoxy, C1-C4-haloalkoxy, amino,
C2-C4-monoalkylamino, C1-C4-dialkylamino,
C1-C4-alkoxycarbonyl, nitro or cyano;
R11 is hydrogen, C1-C6-alkyl or Cl-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, phenyl or
benzyl which may be mono- to pentasubstituted by halogen,
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,
C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;
or
R11 and R12 together with the common nitrogen atom are a
saturated or unsaturated 4- to 7-membered azaheterocycle;
R12' is as defined for R12, but excluding hydrogen;
R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl, cyanu-C1-C6-alkyl;

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53
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl or phenylalkyl, where
the phenyl ring may be mono- to trisubstituted by
halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or
C1-C3-alkoxy;
R14 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
is phenyl or benzyl which may be unsubstituted on the
phenyl ring or may be mono- to trisubstituted by halogen,
cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or
C1-C3-alkoxy;
R14' is as defined for R14, but excluding hydrogen;
Rl5 is hydrogen, hydroxyl, C1-C6-alkyl, Cl-C6-alkoxy,
(C1-C3-alkoxy)carbonyl-C1-C3-alkoxy, C3-C6-alkenyl or
C3-C6-alkynyl;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, C3-C6-alkenyloxy,
(C1-C6-alkoxy)carbonylalkoxy, CZ-C6-alkenyl,
(C2-C6-alkenyl)carbonyloxy, C3-C6-alkynyl,
(CZ-C6-alkynyl)carbonyloxy,
is phenyl, phenoxy or benzyl, where the phenyl rings of
the 3 last-mentioned radicals may be unsubstituted or
mono- to trisubstituted by halogen, cyano, nitro,
C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or
(C1-C3-alkoxy)carbonyl;
R1~ is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or
(C1-C6-alkoxy)carbonyl;
R18 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
is phenyl or phenyl-(C1-C6-alkyl), where the two
last-mentioned phenyl radicals may be substituted by
halogen, cyano, nitro, C1-C3-alkyl, C~_-C3-haloalkyl,
C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;

0~50~5~~8~ CA 02377143 2001-12-19
54
Rls~ Rzo independently of one another are C1-C6-alkyl,
C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy-C1-C6-alkyl, or
Rls and Rzo together are a saturated 2- to 4-membered carbon
chain which may carry an oxo substituent, where a carbon
atom of this chain which is not adjacent to the variables
Zz and Z3 may be replaced by -O-, -S-, -N=, -NH- or
-N(C1-C6-alkyl)- and where the carbon chain may be
substituted once to three times by halogen or
C1-C6-alkyl;
Rzl is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl
or C1-C6-alkoxy;
Rzz is hydrogen, OR31, S-R31, C1-C6-alkyl, which may carry one
or two C1-C6-alkoxy substituents, is Cz-C6-alkenyl,
Cz-C6-alkynyl, C1-C6-haloalkyl or C3-C6-cycloalkyl;
Rz3 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl;
Rz4 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy or
C1-C6-haloalkyl;
Rz5 is hydrogen, cyano or Cl-C6-alkyl;
Rz6, R31 independently of one another are hydrogen,
C1-C6-alkyl, C1-C6-haloalkyl, Cz-C6-alkenyl or
Cz-C6-alkynyl, where the 4 last-mentioned groups may in
each case carry one or two of the following radicals:
cyano, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyl,
(C1-C6-alkoxy)carbonyl;
or are (C1-C6-alkyl)carbonyl, (Cl-C6-alkoxy)carbonyl,
phenyl or phenyl-C1-C6-alkyl;
Rz~, Rzs, Rzs, R3o independently of one another are hydrogen,
C1-C6-alkyl, C3-C6-alkenyl, Cz-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl,
(C1-C6-alkoxy)carbonyl, or
Rz7 and Rzs and/or Rzs and R3o together with the respective
common nitrogen atom are a saturated or unsaturated 4- to
7-membered azaheterocycle which, in addition to carbon

0050/50080
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ring members, may, if desired, contain an oxygen atom or
an -NH- group;
m is 0, 1, 2 or 3.
5
R4 is in particular halogen and specifically fluorine or chlorine.
RA is in particular hydrogen, i.e. rn is 0.
In Q1, R5 is, in particular:
C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy, where
each of the 3 last-mentioned radicals may, if desired,
carry one to three substituents, in each case selected
from the group consisting of halogen, Ci_C6-alkoxy,
C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C6-alkylsulfonyl,
-CO-R14, -CO-OR14, -CO-N(R14)-R15~ -N(R14)_R15 and
_C ( Ri6 ) =N_ORi3
_Cp_R17 ~ -C ( NR18 ) _R17 ~ _C ( R17 ) ( pRl9 ) ( pR20 ) .
_C ( R17 ) =C ( R21 ) _Cp_R22 ~ _Cg ( R17 ) _Cg ( R21 ) _Cp_R22 ~ _Cp_OR26 ,
-Cp_N ( R26 ) _pRl3 ~ _C ( R17 ) =C ( R21 ) -L~p_N ( R26 ) _pRi3 ~
-C(R16)=N_pRl3~ -C(pRi9)(pR2o)_pg26~ _N(R27)R28~ _CON(R27)R28
or -C(R17)=C(R27)CO-N(R27)R28;
in which Ri3 to R22 and R26 to R28 are as defined above,
and specifically C2-C6-alkenyloxy, C2-C6-alkynyloxy,
_C(R17)(pRl9)(pR20)~ _C(R17)oC(R21)_C(p)R21~
_Cg(R17)_CH(R21)_C(O)R22~ C(O)OR26, -C(O)_N(R26)-OR13,
-C(R16)=N-OR13 and C(O)N(R27)R28, in which Ri3, Rls~ Ri7~ Rls~
R2o ~ R21 ~ R22 ~ R26 ~ R27 and R28 have the meanings mentioned
above and in particular those mentioned below:
R13 is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-haloalkenyl, C3-C6-alkynyl, Ci-C6-cyanoalkyl or
Ci-C6_alkoxycarbonyl_Ci-C6-alkyl;
R16 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy,
Ci-C6-alkoxycarbonyl-Ci-C6-alkyl,
Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy or
phenoxycarbonyl-Ci-C6-alkoxy;
R17 is hydrogen, Ci-C6-alkyl;
Ri9 and R2o independently of one another are Ci_C6-alkyl;

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56
R21 is hydrogen, halogen, C1-C6-alkyl;
R2z is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio,
C1-C6-alkoxycarbonyl-C1-C6-alkyl;
10
R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R27 is hydrogen, C1-C6-alkyl;
R2$ is hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
or R2~ and R28 together are a 6-membered saturated
azaheterocycle which may have one or two not adjacent
oxygen atoms in the ring.
R is preferably 'not hydrogen, in particular if Q is one of the
radicals Q1, Q4, Q5 or Q6, and if Z is oxygen.
R is, in particular:
C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12,
-C(O)NHC(O)C1, -C(O)NHS(O)zCl, C(O)NHC(O)OR12',
C(O)NHS(O)ZR12', C(O)R2, P(O)R1(OR1), P(0)(OR1)y; S(0)R2,
S(O)2R2 or S(O)ZNHR2
in which the variables R1, R2, R11, R12 and R12' have the
meanings mentioned above and specifically those listed
below:
R1 is C1-C6-alkyl
R2 is C1-C6-alkyl
R11 is hydrogen or C1-C6-alkyl
R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and
R12' is C1-C6-alkyl and C1-C6-alkyloxy.
R is particularly preferably:

005050080 CA 02377143 2001-12-19
57
hydrogen, or is C1-C6-alkoxycarbonyl or
(C1-C4-alkoxycarbonyl)iminocarbonyl.
A specific class relates to compounds of the formulae Ia and Ib
in which Q is Q1. Here, the variables have the meanings mentioned
above and particularly preferably those below:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12~
-C(0)NHC(O)C1, -C(O)NHS(O)2C1, C(O)NHC(O)OR12',
C(O)NHS(O)2R12~~ C(O)R2r ~''(O)R1(ORI)r p(O)(OR1)2i S(O)R2i
S(O)2R2 or S(O)2NHR2
in which the variables R1, R2, R11, R12 and R12' have the
following meanings:
R1 is C1-C6-alkyl,
R2 is C1-C6-alkyl,
R11 is hydrogen or C1-C6-alkyl,
R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and
R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O
35
X is O or S,
m has the value 0,
R3 is hydrogen or halogen, in particular fluorine or
chlorine,
R4 is hydrogen, halogen, in particular fluorine or chlorine,
or cyano, and
R5 is Cl-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl,
C3-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
Ci-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C1-C6-haloalkenyloxy, C3-C6-alkenylthio,
C3-C6-haloalkenylthio, C1-C6-alkoxycarbonyl-C1-C6-alkoxy,
C3-C6-alkenyloxycarbonyl-C1-C6-alkoxy,
C3-C6-alkynyloxycarbonyl-C1-C6-alkoxy,
C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkoxy,
C3-C6-alkenyloxycarbonyl-C1-C6-alkoxycarbonyl-

CA 02377143 2001-12-19
58
C1-C4-alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkylthio,
C1-C6-alkenyloxycarbonyl-C1-C6-alkylthio,
C1-C6-alkynyloxycarbonyl-C1-C6-alkylthio,
C1-C6-alkoxy-Cl-C6-alkoxycarbonyl-C1-C6-alkylthio,
C1-C6-alkoxyimino-C1-C6-alkyl,
N-C1-C6-alkoxy-N-(C1-C6-alkyl)amino-C1-C6-alkyl,
C1-C6-alkylsulfonylamino, -COOR26, -CONR2~R2~,
-C(=NRls)Rl~, -C(R16)=NOR13, C(Rl~)=C(R21)_CO-R22~
where the variables R13, Rls, R1~, R21, R22~ R2s to R28 have the
following meanings:
R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-cyanoalkyl or
C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R16 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
C1-G6-alkoxycarbonyl-C1-C6-alkyl,
C1-C6-alkoxycarbonyl-C1-C6-alkoxy or
phenoxycarbonyl-C1-C6-alkoxy;
R1~ is hydrogen, C1-C6-alkyl;
R1$ is C1-C6-alkoxy;
R21 is hydrogen, halogen, C1-C6-alkyl;
R22 is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio,
C1-C6-alkoxycarbonyl-C1-C6-alkyl;
35
R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl,
C3-C6-alkenyloxycarbonyl-C1-C6-alkyl,
C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R2~ is hydrogen, C1-C6-alkyl;
R2B is hydrogen, C1-C6-alkyl, C1-C6-alkoxy,
or R27 and R28 together are a 6-membered saturated
azaheterocycle which may have one or two not adjacent
oxygen atoms in the ring.
In particular, R5 has the following meaning:

0050/50080
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R5 is CN, COOH, C1-C4-alkoxyiminomethyl, C1-C4-alkoxy,
C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy,
C3-C6-alkenyloxyiminomethyl,
(C1-C4-alkoxycarbonyl)-C2-C6-alkenyloxy,
C3-C6-alkynyloxyiminomethyl,
2-[C1-C4-alkoxycarbonylj-2-chloroethyl,
2-[C1-C4-alkoxycarbonylj-2-chloroethenyl,
C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy,
(C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl,
is COOR26, where R26 = C1-C4-alkoxy-C1-C4-alkyl or
C3-C6-alkenyloxycarbonyl-C1-C4-alkyl,
is CONR2~R28, where R2~ = hydrogen or C1-C4-alkyl and R28 =
hydrogen, C1-C4-alkyl or C1-C4-alkoxy;
is C(=NR17)Ri8, in which Rl~ is C1-C4-alkoxy and R1$ is
C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.
Two further classes relate to compounds of the formulae Ia and I,b
in which Q is Q2 or Q3. Here, the variables, independently of one
another, particularly preferably have the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12,
-C(O)NHG(0)C1, -C(O)NHS(O)2C1, C(O)NHC(O)OR12~,
C(0)NHS(O)2R12~~ C(O)R2. p(O)R1(OR1). p(O)(OR1)2: S(O)R2.
S(O)2R2 or S(O)2NHR2
in which the variables R1, R2, R11, R12 and R12' have the
following meanings:
R1 is C1-C6-alkyl,
R2 is C1-C6-alkyl,
R11 is hydrogen or C1-C6-alkyl,
R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and
R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O,
X is O or S,

CA 02377143 2001-12-19
m has the value 0,
R3 is hydrogen or halogen,
R4 is hydrogen or halogen,
Y is O or S,
U is a single bond, oxygen or C1-C4-alkylene and
R6 is hydrogen, halogen, cyano, C1-C6-alkyl, Ci-C6-haloalkyl,
C3-C7-cycloalkyl, saturated C3-C~-heterocyclyl which has
one or two heteroatoms selected from the group consisting
of oxygen and sulfur in the ring, is Cl-C6-alkoxyalkyl,
cyano-C1-C6-alkyl, C02H, C1-C6-alkoxycarbonyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl.
Two further classes relate to compounds of the formulae Ia and Ib
in which Q is Q4 or Q5. Here, the variables, independently of one
another, particularly preferably have the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12,
-C(O)NHC(O)C1, -C(O)NHS(O)2C1, C(O)NHC(O)ORIZ',
C(O)NHS(O)ZRiz', C(O)R2, P(O)R1(OR1), P(O)(OR1)2: S(O)R2,
S(O)2R2 or S(O)2NHR2
in which the variables R'1, R2, R11, R12 and R12' have the
following meanings-.
R1 is C1-C6-alkyl,
R2 is C1-C6-alkyl,
R11 is hydrogen or C1-C6-alkyl,
R1z is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and
R12' is C1-C6-alkyl and C1-C6-alkyloxy;
Z is O or S, in particular O,
X is O or S,
m has the value 0,

0050/50080
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61
R3 is hydrogen or halogen,
Y is O or S,
Y' in the formula Q5 is oxygen or sulfur,
T is a single bond, oxygen or C1-C4-alkylene and
R7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C3-C~-cycloalkyl, saturated C3-C~-heterocyclyl which has
one or two heteroatoms selected from the group consisting
of oxygen and sulfur in the ring, C1-C6-alkoxyalkyl,
cyano-C1-C6-alkyl, C02H, C1-C6-alkoxycarbonyl,
C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or
C3-C6-alkynyl.
A further class relates to compounds of the formulae Ia and Ib in
which Q is Q6. Here, the variables have the meanings mentioned
above and, independently of one another, the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl,
(C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12~
-C(O)NHC(O)Cl, -C(O)NHS(O)2C1, C(O)NHC(O)OR12',
C(O)NHS(O)2R12~i C(Q)R2r P(~)R1(OR1)r 1'(~)(~R1)2: S(O)R2, .
S(O)2R2 or S(O)2NHR2
in which the variablea R1, R2, R11, Ri2 and R12' have the
following meanings:
R1 is C1-C6-alkyl,
R2 is C1-C6-alkyl,
R11 is hydrogen or C1-C6-alkyl,
R12 is hydrogen, C1-C6-alkyl or,Cl-C6-alkoxy, and
R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O,
X is O or S,
m has the value 0,
R3 is hydrogen or halogen,

0050/50080
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62
R4 is hydrogen or halogen, where
Rs and R9 independently of one another are hydrogen,
C1-C6-alkyl, halogen, cycloalkyl or C1-C6-haloalkyl, or
R8 and R9 together with the carbon atom to which they are
attached are a carbonyl group.
Particular preference is given to compounds of the formula Id, in
which the variables have the abovementioned meanings.
Very particular preference is given to compounds of the formula
Ib, in which the variables have the meanings mentioned above as
being preferred.
Specifically preferred are compounds of the formulae Ia and Ib
and amongst these in particular the compounds of the formula Ib,
in which
Q is Q1,
Z is oxygen,
X is oxygen or sulfur,
m has the value 0,
R is hydrogen, C1-C4-alkoxycarbonyl or
(C1-C4-alkoxycarbonyl)iminocarbonyl,
R3 is fluorine, chlorine or hydrogen,
R4 is halogen, and
R5 is CN, GOOH, C1-G4-alkoxyiminomethyl, C1-C4-alkoxy,
C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy,
C3-C6-alkenyloxyiminomethyl,
(C1-C4-alkoxycarbonyl)-CZ-C6-alkenyloxy,
C3-C6-alkynyloxyiminomethyl,
2-[C1-C4-alkoxycarbonyl]-2-chloroethyl,
2-(C1-C4-alkoxycarbonyl]-2-chloroethenyl,
C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy,
(C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl,
is COOR26, where R26 = C1-C4-alkoxy-C1-C4-alkyl or
C3-C6-alkenyloxycarbonyl-C1-C4-alkyl,

0050~5~~80 CA 02377143 2001-12-19
~3
is CONR2~R28, where R27 = hydrogen or C1-C4-alkyl and R2$ _
is hydrogen, C1-C4-alkyl or Ci-C4-alkoxy;
is C(=NR1~)R18, in which R1~ is C1-C4-alkoxy and R1s is
C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.
15
25
35
45

005050080
CA 02377143 2001-12-19
64
Particularly preferred compounds of the formula Ia are the
compounds Ial.l to Ia1.206 listed in Table 1 below.
Table 1
R3
X
~N~NH ~ ~ R4 I a
Z N
~02CH3
No . Z X R3 R4 R5
I a.1 O S H Cl OCH2C~CH
I a.2 O S H Cl OCH2CH=CH2
I a.3 O S H Cl OCH(CH3)C$CH
I a.4 O S F Cl OCH2CsCH
I a.5 O S F C1 OCH2CH=CH2
I a.6 O S F C1 OCH(CH3)C~CH
I a.7 O S H C1 COZCH3
I a.8 O S H C1 C02CHZCH=CHZ
I a.9 O S H Cl COZCH2C~CH
I a.10 O S H C1 C02CHZCHZOCH3
I a.11 O S F C1 C02CH3
I a.12 O S F C1 C02CH2CH=CHZ
I a.13 O S F C1 C02CHZC~CH
I a.14 O S F C1 C02CHZCHZOCH3
I a.15 0 S H CN OCHZC3CH
I a.16 O S F CN OCHZC~CH
I a.17 O S H C1 OCH2C02CH3
I a.18 O S H C1 OCHZCOZCHZC~CH
I a.19 O S H C1 OCHZC02CH2CHZOCH3
I a.20 O S H C1 OCH2COzC(CH3)2C02CHZCH=CHZ
I a.21 O S F Cl OCH2COZCH3
I a.22 0 S F Cl OCH2COZCHZC~CH
I a.23 O S F C1 OCH2C02CHZCHzOCH3
I a.24 0 S F C1 OCH(CH3)C02CH3
I a.25 O S F Cl OCH(CH3)COyC2H5
I I a.26 O S F I C1 OCH(CH3)C02CHzCH=CHz
I ~ I I

005~~5~080 CA 02377143 2001-12-19
No . Z X R3 R4 R5
I a.27 O S F C1 OCH(CH3)C02CHZC~CH
I a.28 O S F C1 OCH(CH3)C02CHZCH20CH3
5 I a.29 0 S F C1 OCH2C02-nC5Hi1
I a.30 O S F C1 OCH(CHg)C02-nC5Hi1
I a.31 O S H C1 COZCH2C02CH3
I a.32 O S H C1 COZCHZCO~GzH5
I a.33 O S H C1 C02C(CH3)2C02CH2CH=CHZ
10
I a.34 O S F C1 COZCH2C02CH3
I a.35 O S F C1 C02CHZC02C2Hg
I a . O S F C1 COZC ( CH3 ) 2COZCH2CH=CH2
3 6
I a.37 O S F CN C02CH3
15 I a , O S F CN C02C2H5
3 8
I a . O S F CN C02GHZCH20CH3
3 9
I a . 0 S F CN C02CHZC02CHg
4 0
I a.41 O S F CN C02CHZC02CyH5
20 I a.42 O S F CN C02C(CH3)2C02CH2CH=CH2
I a . O S F CN OCHZC02CH3
4 3
I a.44 O S F CN OCH2C02C2H5
I a . O S F CN OCH2C02CHZCeCH
4 5
25 I a.46 O S F CN OCH2C02CH2CHZOCH3
I a.47 O S F CN OCH(CH3)C02CH3
I a.48 O S F CN OCH(CH3)COZG2H5
I a.49 O O F CN OCH(CH3)C02CHZCH20CH3
I a.50 O S H C1 NHS02CHg
30 I a.51 O S H C1 NHS02C2H5
I a.52 O S H Cl NHSOZ-nC3H7
I a.53 O S H Cl NHS02-iC3H7
I a.54 O S F Cl NHS02CH3
35 I a.55 O S F C1 NHS02CZH5
I a.56 O S F C1 NHSOz-nC3H7
I a.57 O S F C1 NHSOZ-iC3H7
I a.58 O S F CN NHS02CH3
40 I a.59 O S F CN NHS02C2H5
I a.60 0 S F CN NHS02-nC3H7
I a.61 O S F CN NHS02-iC3H7
I a.62 O S H Cl OCH2C(C1)=CHz
I a.63 O S C1 C1 OCH~C(C1)=CHZ
45 I
I a.64 O S F Cl OCH2C(Cl)=CH2
I a.65 O S F CN OCH2C(C1)=CHZ

0050/50080
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66
NO. ~ Z X R3 Ft4 RS
'
I a.66 O S Cl C1 OCH2C~CH
I a.67 O S C1 C1 OCHzCH=CH2
I a.68 O S C1 Cl OCH2COZCH3
I a.69 O S C1 Cl OCH2C02nC5H11
I a.70 O S C1 C1 OCH(CH3)COZCH3
I a.71 O S C1 Cl OCH(GH3)C02CH2CH=CHZ
I a.72 O S C1 C1 OCH(CH3)COZCH2CH20CH3
0
1 I a.73 O S C1 C1 C02CH3
I a.74 O S C1 Cl C02C2H5
I a.75 O S C1 Cl C02CHZC02CH3
I a. 76 O 0 C1 C1 C02C ( CH3 ) 2C02CH3
15I a.77 O S H C1 SCH2C$CH
I a.78 O S H C1 SCH2CH=CH2
I a.79 O S H Cl SCHZC02CH3
I a.80 O S H C1 SCH2C02-nC5H11
20I a.81 O S H Cl SCH(CH3)C02CH3
I a.82 O S H C1 SCH(CH3)C02CH2CH20CH3
I a.83 O S H C1 SCHZC02CHZCH20CH3
I a.84 O S H Cl OCFyCHFCl
25I a.85 O S C1 Cl SCH2C~CH
I a.86 O S C1 Cl SCH2CH=CH2
I a.87 O S C1 Cl SCHZC02CH3
I a.88 O S C1 C1 SCH2G02-nC5H11
I a.89 O S C1 C1 SCH(CH3)COZCH3
30I a.90 O S Cl C1 SCH(CH3)C02CHzCH20CH3
I a.91 O S C1 C1 SCH2C02CHZCH20CH3
I a.92 O S C1 C1 OCF2CHFC1
I a.93 O S F Cl SCH2C~CH
35I a.94 O S F C1 SCH2CH=CH2
I a.95 O S F C1 SCH2COzCH3
I a.96 O S F C1 SCH2C02-nCSHli
I a.97 O S F C1 SCH(CH3)C02CH3
40I av98 O S F C1 SCH(CH3)C02CHZCHZOCHg
I a.99 O S F C1 SCH2C02CHZCH20CH3
I a.100 O S F C1 OCFZCHFCl
I a.101 O S F CN SCH2C~CH
I a.102 O S F CN SCH2CH=CH2
45
I a.103 O O F CN SCH2C02CH3
I a.104 O S F CN SCH2C02-nC5H11

0050/50080
CA 02377143 2001-12-19
67
No . Z X R3 R4 R5
I a.105 O S F CN SCH(CH3)C02CH3
I a.106 O S F CN SCH(CH3)COzCH2CH20CH3
I a.107 O S F CN SCH2COzCH2CHZOCH3
I a.108 O S H C1 C(O)N(CH3)z
I a.109 O S F C1 C(O)N(CH3)z
I a.110 O S F CN C(0)N(CH3)z
I a.lll O S H C1 C(O)-N(C2H4)z0
I x,112 O S H F C(O)-N(C2H4)z0
I a.113 O S H Cl CH=N-OCH3
I a.114 O S H Cl CH=N-OC2H5
I a.115 O S H C1 C(O)NHOCH3
I a.116 O S H C1 C(0)NHOC2H5
I a.117 O S H C1 C(=N-OCH3)OCH3
I a.118 0 S H C1 C(=N-OCH3)OC2H5
I a.119 0 S H C1 C(=N-OGH3)OCH2C02CH3
I a.120 O S H C1 C(=N-OCH3)OCH(CH3)C02CH3
I a.121 O S H C1 CH=CH-C02CH3
I a.122 0 S H C1 CH=CH-C02CzH5
I a.123 O S H C1 CH=C(CH3)C02CH3
I x124 O S H Cl CH=C(CH3)C02CzH5
I a.125 O S H Cl CH=C(C1)C02CH3
I a.126 O S H C1 CH=C(C1)COzC2H5
I a.127 O S H C1 CH=C(Br)CHZC2H5
I a.128 O S H Cl CH2N(CH3)OCH3
I x,129 O O H C1 C(=N-OCH3)OCH2COyPhenyl
I a.130 O S H F CH=N-OC2H5
I a.131 O S H F C(O)NHOCH3
I a.132 O S H F C(0)NHOCzHS
I a.133 0 S H F C(=N-OCH3)OCH3
I a.134 0 S H F C(=N-OCH3)OCZHS
I a.135 O S H F C(=N-OCH3)OCHzC02CH3
I a.136 0 S H F C(=N-OCH3)OCH(CH3)COzCH3
I x137 O S H F CH=CH-C02CH3
I a.138 O S H F CH=CH-COZC2H5
I a.139 0 S H F CH=C(CH3)C02CH3
I a.140 O S H F CH=C(CH3)C02C2H5
I a.141 O S H F CH=C(C1)C02CH3
I a.142 O S H F CH=C(C1)C02CZH5
I a.143 O S H F CH=C(Br)C02CZH5

0050/50080
CA 02377143 2001-12-19
6 ~3
N o . z x 3 R4 ~5
R
I a.144 O S F CHZN(CH3)OCH3
H
I a.145 O S F C(=N-OCH3)OCHzC02Phenyl
H
I a.146 O S F CH=N-OCH3
H
I a.147 O S CN CH=N-OCH3
F
I a.148 0 S F CN CH=N-OC2H5
I a.149 O 5 F CN C(O)NHOCH3
I a.150 O S F CN C(O)NHOC2H5
I a.151 O S F CN C(=N-OCH3)OCH3
I a.152 O S F CN C(=N-OCH3)OCZHS
I a.153 O S F CN C(=N-OCH3)OCHZC02CH3
I a.154 O S F GN C(=N-OCH3)OCH(CH3)COZCH3
I a.155 O O F CN CH=CH-C02CH3
I a.156 O S F CN CH=CH-C02CzH5
I a.157 O S F CN CH=C(CH3)COZCH3
I a.158 O S F CN CH=C(CH3)COzC2H5
I x159 O S F CN CH=C(Cl)C02CH3
I a.160 O S F CN CH=C(C1)COZC2H5
I a.161 O S F CN CH=C(Br)COZCZHS
I a.162 O S F CN CHZ-N(CH3)OCH3
I a.163 O S F CN C(N-OCH3)OCH2C02C6H5
I a.164 O S H C1 CH=N-OCH2-C=CH
I a.165 O S H G1 CH=N-OCHZ-C(C1)=CHZ
I a.166 O S F Cl CHZ-GH(C1)C02CZH5
I a.167 O S H C1 CH=N-OCHzC02CH3
I x.168 O 5 H C1 CH=N-OCHZC02CZH5
I a.169 O S H C1 CH=N-OCH2CHZC1
I a.170 O S H C1 CH=N-OCHzCN
I a.171 O S H C1 CH=N-OCH(CH3)COZCH3
I a.172 0 S H C1 CH=C(C1)COSCH3
I a.173 O S H C1 CH=C(Br)COSCH3
I a.174 O S H C1 CH=C(C1)C02CHZG02CH3
I a.175 O S H C1 CH=C(C1)C02CH(CH3)C02CH3
I a.176 O S H C1 C(CH3)=NOGH3
I a.177 O S H C1 C(CH3)=NOC2H5
I a.178 O S H C1 C(CH3)=NOCH2C02CH3
I a.179 O S F C1 CH=N-OCHZC~CH
I a.180 O S F C1 CH=N-OCH2-C(C1)=CH2
I a.181 O S F C1 CH=N-OCH2C02CH3
I a.182 O O F C1 CH=N-OCHZC02C2H5

0050/50080
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69
No . Z X R3 R4 R5
.
I a.183 0 S F C1 CH=N-OCH2CH2C1
I a.184 O S F C1 CH=N-OCH2CN
I a.185 O S F Cl CH=N-OCH(CH3)C02CH3
I a.186 O S F C1 CH=C(Cl)COSCH3
I a.187 0 S F C1 CH=C(Br)COSCH3
I a.188 0 S F C1 CH=C{C1}C02CHZC02CH3
I a.189 O S F C1 CH=C(C1)COZCH(CH3)C02CH3
I a.190 O S F C1 C(CH3)=N-OCH3
I a.191 O S F C1 C(CH3)=N-OCZH5
I a.192 O S F C1 C(CH3)=N-OCH2COZCH3
I a.193 O S C1 Cl CH=N-O-OCH2C~CH
15I x,194 O S C1 C1 CH=N-OCHZ-C(C1)=CH2
I a.195 O S C1 C1 CH=N-OCH2C02CH3
I a.196 O S C1 C1 CH=N-OCH2COZC2H5
I a.197 O S C1 C1 CH=N-OCHzCHZCl
20I a.198 O S C1 C1 CH=N-OCH2CN
I a.199 O S C1 C1 CH=N-OCH(CH3)C02CH3
I a.200 O S C1 C1 CH=C(C1)COSCH3
I a.201 0 S C1 C1 CH=C(Br)COSCH3
25I a.202 O S Cl C1 CH=C(C1)COZCH2C02CH3
I a.203 O S C1 C1 CH=C(C1)C02CH(CH3)COzCH3
I a.204 O S Cl C1 C(CH3)=NOCH3
I a.205 O S C1 C1 C(CH3)=NOC2H5
I a.206 O O C1 C1 C(CH3}=NOCH2COZCH3
30
Furthermore, particular preference is given to the substituted
ureas of the formula Ib, in particular to the compounds Ibl.l to
Ib1.206 which differ from the corresponding compounds Ial.l to
35 Ia1,206 only in that the N-substituents are inverted:
H3C02 i R3 / R4
Rs Ib1
45 preference is furthermore given to the compounds Ia2.1 to Ia2.206
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:

0050/50080
CA 02377143 2001-12-19
R3
X
I
N~~.~ ~ \ Ra laz
~N~
5 ~ C02CzH5 s
10 Preference is furthermore given to the compounds Ib2.1 to Ib2.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
C02C2H5
15 N R3
Ib2
Z~/N. -
\ / R
R5
Preference is furthermore given to the compounds Ia3.1 to Ia3.206,
in which the variables Z, X, R3, R4 and RS each have the meanings
mentioned in rows 1 to 206:
X
~I
N~~~ / \ R4 1a3
~I
LUN~Cp2 s
Preference is furthermore given to the compounds Ib3.1 to Ib3.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
~C~
~N\C~p R Ib3
X \ ~ Ra
R5

0050/50080
CA 02377143 2001-12-19
71
Preference is furthermore given to the compounds Ia4.1 to Ia4.206,
in which the variables Z, X, R3, R4 and RS each have the meanings
mentioned in rows 1 to 206:
X Rs
N~C.~ ~ ~ R4 1a4
~N
C02 s
~~4Ha
I0
Preference is furthermore given to the compounds Ib4.1 to Ib4.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
I5 mentioned in rows 1 to 206:
~'4H8
N,C~ Ra
Iba
~/N~C~ /
'R
Preference is furthermore given to the compounds Ia5.1 to Ia5.206,
in which the variables Z, X, R3, R4 and RS each have the meanings
mentioned in rows 1 to 206:
R3
X
I I
N~C~~ Ro las
FiI
~N~ s
C02
wt-CaHa
Preference is furthermore given to the compounds Ib5.1 to Ib5.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
45

0050/50080
CA 02377143 2001-12-19
72
~t-CaHs
N,C02 R3
~N~ ~~ Ib'
C /
a
'R
10 Preference is furthermore given to the compounds Ia6.1 to Ia6.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
R3
X
I
~~. / ~ Ra
~N ~ _ las
Z~N~C-SCH3 s
Preference is furthermore given to the compounds Ibs.l to Ib5.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
O
N~-SCH3 R3
~N
W/ ~C' /
X ~ I Ra
R5
Preference is furthermore given to the compounds Ia7.1 to Ia7.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
R3
X
I
N'~~~ / ~ Ra lay
Z~N~CHO 5

0050/50080 CA 02377143 2001-12-19
73
Preference is furthermore given to the compounds Ib7.1 to Ib7.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
~N~CHO Ra
zr~N.C.~ / Ib~
\ ~ Ra
s
Preference is furthermore given to the compounds Ias.l to Ia8.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
R3
X
1
N~~.~ ~ ~ Ra laa
~N\ 5
CN
Preference is furthermore given to the compounds Ibs.l to Ib8.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
N~CN Rs
~
~N~ .~ Iba
C
\ R4
5
Preference is furthermore given to the compounds Ia9.1 to Ia9.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
45

~050~5~~$0 CA 02377143 2001-12-19
74
R
N~"~ / \ Ra
~' - l as
~N
~C-NHCH3 s
Preference is furthermore given to the compounds Ib9.1 to Ibg.206,
in which the variables Z, X, R3, R4 and R5 each have the meanings
mentioned in rows 1 to 206:
~~ ~NHCH3
NBC Rs
~N~ ~~ Iba
O
a
R
Rs
Preference is furthermore given to the compounds Ial~.l to
Ia1~.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
R3
X
I
N.~.~ / \ Ra
~N H la,o
~C-NHOCH3 s
Preference is furthermore given to the compounds Ibl~.l to
Ib1~.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
~~ ~NHOCH3
I NiC Rs
Z~N\C~~ / Ib,o
X ~ ~ a
'R
5

005050080 CA 02377143 2001-12-19
7
Preference is furthermore given to the compounds Iali.l to
Ia11.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
X R3
I I
N~C~ ~ ~ Ra
N ~ 1a»
U ~ s
IC-~I-IC-CI
O O
Preference is furthermore given to the compounds Ibll.l to
Ib11.206, in which the variables Z, X, R3, R4 and RS each have the
meanings mentioned in rows 1 to 206:
O
O\~ N- ~- CI
If R3 Ib~~
~N~ ~~
C
X ~ a
'R
s
Preference is furthermore given to the compounds Ia12.1 to
Ia12.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
Ra
X
~I
N~~~ ~ ~ Ra
I ~ la~z
Z,~ N
s
C-NHS02CI
I I
O
Preference is furthermore given to the compounds Ib12.1 to
Ib12.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
45

CA 02377143 2001-12-19
~ ft
~~~ NHS02CI
R3
Ib~2
\~N..C. /
X \ Ra
s
Preference is furthermore given to the compounds Ia13.1 to
Ia13.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
R3
X
I
N~~~~ ~ \ Ra
H 1a13
5
C-NHC02CH3
I I
O
Preference is furthermore given to the compounds Ib13.1 to
Ib13~206, in which the variables Z, X, R3, R4 and RS each have the
meanings mentioned in rows 1 to 206:
~~~NHC02CH3
R3 Ib~3
~N~
C /
X \ R4
5
Preference is furthermore given to the compounds Ia14.1 to
Ia14.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
R3
X
I
\
~N~ \~ R4 lava
zu ~ s
C-NHSOzCH3
I I
O

~~r~~~r~~p8~ CA 02377143 2001-12-19
77
Preference is furthermore given to the compounds Ib14.1 to
Ib14.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
O
~~~NHS02CH3
R3 Ib~a
~/N~C~ /
Ra
5
Preference is furthermore given to the compounds Ia15.1 to
Ia15.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
Ra
X
~I
N~~~~ ~ ~ R4 ~a~s
HN
a ~ 5
C-CH3
I I
O
Preference is furthermore given to the compounds Ibl5.I to
Ib15.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
~~~ CH3
R3 ~b~s
~/N~C~ /
Ra
5
Preference is furthermore given to the compounds Ia16.1 to
Ia16.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
45

CA 02377143 2001-12-19
78
X
I
N'~~ ~ ~ R4 18
~N ~ la
\il 5
P(O)CH3(OCHa)
Preference is furthermore given to the compounds Ib16.1 to
Ia16.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
P(O)CH3(OCH3)
i R3 Ibis
~N~
C /
X \ inn
5
Preference is furthermore given to the compounds Ia17.1 to
Ia1~.206, in which the variables Z, X, R3, R4 and RS each have the
meanings mentioned in rows 1 to 206:
X
N'~~ ~ ~ R4 la~~
~I
5
P(O)(OCH3)2
Preference is furthermore given to the compounds Ibl~.l to
Ib17.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
P(O)(OCH3)2
~ IN ~ R3 Ib,~
Z\/N~C~~ /
X \ I R4
5

CA 02377143 2001-12-19
79
Preference is furthermore given to the compounds Iale.l to
Ia18.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
X R3
I
N~~~ ~ ~ Ra
~N ~ lace
5
S(O)CH3
Preference is furthermore given to the compounds Ib18.1 to
Ib18.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
S(O)CH3
R3 Ib~e
~I
~N~ .
C
X ~ Ra
R5
Preference is furthermore given to the compounds Ia19.1 to
Ia19.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
R3
X
I I
N~C.~ ~ ~ Ra
H lace
U 5
S02CH3
Preference is furthermore given to the compounds Ib19.1 to
Ib19.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
45

005050080 CA 02377143 2001-12-19
S02CH3
I
~N H R3 Ib~9
5 Z\/N~C~~ /
X \ I Ra
5
10 Preference is furthermore given to the compounds Ia2o.1 to
IaZO.206, in which the variables Z, X, R3, R4 and R5 each have the
meanings mentioned in rows 1 to 206:
R3
X
~N~ .~ ~ ~ Ra 20
t[ I la
\/ ~ s
S02NHCH3
Preference is furthermore given to the compounds IbZO.l to
Ib2o.206, in which the variables Z, X, R3, R4 and Rs each have the
meanings mentioned in rows 1 to 206:
S02NHCH3
H R3 Ib2o
Z\/N~C~~ /
X \ I Ra
5
Preference is furthermore given to the compounds Ia2i to 40,1 to
Ia21 to 40.206, in which the variables X, R3, R4 and RS each have
the meanings mentioned in rows 1 to 206 and the radical R has the
meaning mentioned in the formulae Tal to Ia2o:
R3
X
I
N~~.N ~ Ra laze wao
~I H
U 5
R

0050/50080
CA 02377143 2001-12-19
81
Preference is furthermore given tr. the compounds Ibzl to 40,1 to
Ibzl to 40,206, in which the variables X, R3, R4 and RS each have
the meanings mentioned in rows 1 to 206 and the radical R has the
meaning mentioned in the formulae Ibl to Ibzo:
R
R3 Iba~ ~oao
I H
~N~ ,N
0
Ra
5
Moreover, particular preference is given to the substituted ureas
of the formula Ia.bl
X
I
~N' ~~ ~ la.b~
Z~NH O
'YURS
in particular to the compounds listed in Table 2:
Table 2
No . -,, X Z Y U R6
Ia.bl 1 S S O H
Ia.bl 2 S S O CH3
Ia.bl 3 S S O CzHS
Ia.bl 4 S S 0 n-C3H7
Ia.bl 5 S S 0 i-C3H~
Ia.bl 6 S S O cyclopropyl
Ia.bl 7 S S O n-C4H9 __
Ia.bl 8 S S O sec-C4H9
Ia.bl 9 S S O I-C4H9
Ia.bl 10 S S O t-C4H9
Ia.bl 11 S S 0 CHZ cyclopropyl
Ia.bl 12 S S O cyclopentyl
Ia.bl 13 S S O cyclohexyl
Ia.bl 14 5 S 0 oxiran-2-yl
Ia.bl 15 5 S 0 oxetan-2-yl

CA 02377143 2001-12-19
82
No . X Z Y U R6
~
Ia.bl 16 S S 0 tetrahydrofuran-2-yl
Ia.bl 17 S S O tetrahydropyran-2-yl
~
Ia.bl 18 S S O oxepan-2-yl
Ia.bl 19 S S O thiiran-2-yl
Ia.bl 20 S S 0 thietan-2-yl
Ia.bl 21 S S O tetrahydrothiofuran-2-yl
Ia.bl 22 S S O tetrahydrothiopyran-2-yl
Ia.bl 23 S S O thiepan-2-yl
Ia.bl 24 S S O oxetan-3-yl
Ia.b1 25 S S O tetrahydrofuran-3-yl
Ia.bl 26 S S O tetrahydropyran-3-yl
Ia.bl 27 S S O oxepan-3-yl
Ia.b1 28 S S 0 thiethan-3-yl
Ia.bl 29 S S O tetrahydrothiofuran-3-yl
Ia.bl 30 S S 0 tetrahydrothiopyran-3-yl
Ia.bl 31 S S O thiepan-3-yl
Ia.bl 32 S S O tetrahydropyran-4-yl
Ia.bl 33 S S O oxepan-4-yl
Ia.bl 34 S S 0 tetrahydrothiopyran-4-yl
Ia'b1 35 S S O oxepan-4-yl
Ia.bl 36 S S O tetrahydrothiopyran-4-yl
Ia.bl 37 S S 0 O CH3
Ia.bl 38 S S O O CZHS
Ia.bl 39 S S O O n-C3H7
Ia.bl 40 S S O O i-C3H7
Ia.bl 41 S S O O cyclopropyl
Ia.bl 42 S S O COZH
Ia.bl 43 S S O COZCH3
Ia.bl 44 S S O COZC2H5
Ia.bl 45 S S O CHZCOZCH3
Ia.bl 46 S S O CH(CH3)C02CH3
Ia.bl 47 S S 0 O CH2GOyCH3
Ia.bl 48 S S O O CH(CH3)C02CH3
Ia.bl 49 S S 0 C1
Ia.bl 50 S S O CN
Ia.bl 51 S S 0 CHZC~CH
Ia.bl 52 S S O O CH2C=-CH
Ia.bl 53 S S O CHZOCH3
Ia.bl 54 S S O CH2CHZOCH3

0050500$0 CA 02377143 2001-12-19
83
No . ' X Z Y U R6
Ia.bl 55 S S O O CHpCHyOCH3
Ia.bl 56 S S O CH2 cyclopentyl
Ia.bl 57 S 0 O H
Ia. b1 58 S O O CH3
Ia.bl 59 S O 0 C2H5
Ia.bl 60 S O O n-C3H7
Ia.bl 61 S O 0 I-C3H7
Ia.bl 62 S O 0 cyclopropyl
Ia.bl 63 S O O n-C4H9
Ia.bl 64 S O O sec-C4Hg
Ia.bl 65 S O 0 i-C4H9
15Ia.bl 66 S O O t-C4H9
Ia.bl 67 S O O CH2 cyclopropyl
Ia.bl 68 S O O cyclopentyl
Ia.bl 69 S O O cyclohexyl
20Ia.bl 70 S O O oxiran-2-yl
Ia.bl 71 S O O oxetan-2-yl
Ia.bl 72 S O O tetrahydrofuran-2-yl
Ia.bl 73 S O O tetrahydropyran-2-yl
25Ia.bl 74 S O O oxepan-2-yl
Ia.bl 75 S O O thiiran-2-yl
Ia.bl 76 S O O thietan-2-yl
Ia.bl 77 S O O tetrahydrothiofuran-2-yl
Ia.bl 78 S O O tetrahydrothiopyran-2-yl
30Ia.bl 79 S O O thiepan-2-yl
Ia.bl 80 S O O oxetan-3-yl
Ia.bl 81 S O O tetrahydrofuran-3-yl
Ia.bl 82 S O O tetrahydropyran-3-yl
35Ia.bl 83 S O O oxepan-3-yl
Ia.bl 84 S O O thiethan-3-yl
Ia.bl 85 S O 0 tetrahydrothiofuran-3-yl
Ia.bl 86 S O 0 tetrahydrothiopyran-3-yl
40Ia.bl 87 S O O thiepan-3-yl
Ia.bl 88 S O O tetrahydropyran-4-yl
Ia.bl 89 S O O oxepan-4-yl
Ia.bl 90 S O O tetrahydrothiopyran-4-yl
Ia.bl 91 S O O oxepan-4-yl
45
Ia.bl 92 S O O tetrahydrothiopyran-4-yl
Ia.bl 93 S O O O CH3

~~5~~5~~$~ CA 02377143 2001-12-19
84
No . X Z Y U R6
Ia.bl 94 S O O O C2H5
Ia.bl 95 S 0 O O n-C3H~
Ia.bl 96 S 0 O O i-C3H~
Ia.bl 97 S O O O cyclopropyl
Ia.bl 98 S 0 O COZH
Ia.bl 99 S 0 O C02CH3
Ia.bl 100 S O O C02C2H5
Ia.bl 101 S O O CH2C02CH3
Ia.bl 102 S O O CH(CH3)C02CH3
Ia.bl 103 S O O O CHZC02CH3
Ia.bl 104 S O O O CH(CH3)COzCH3
Ia.bl 105 S O O C1
Ia.bl 106 S O O CN
Ia.bl 107 S O O CH2CcCH
Ia.bl 108 S O O O CHZC~CH
Ia.bl 109 S O O CH20CH3
Ia.bl 110 S O O CHZCHZOCH3
Ia.bl 111 S O O O CH2CHzOCH3
Ia.bl 112 S 0 O CHZ cyclopentyl
Ia.bl 113 O S O H
Ia.bl 114 O S O CH3
Ia.bl 115 O S O C2H5
Ia.bl 116 O S O n-C3H~
Ia.bl 117 O S O I-C3H~
Ia.bl 118 O S O cyclopropyl
Ia.bl 119 0 S O n-C4H9
Ia.bl 120 O S O sec-C4H9
Ia.bl 121 O S O i-CqH9
Ia.bl 122 0 S O t-C4H9
Ia.bl 123 O S 0 CH2 cyclopropyl
Ia.bl 124 O S O cyclopentyl
Ia.bl 125 0 S 0 cyclohexyl
Ia.bl 126 O S O oxiran-2-yl
Ia.bl 127 0 S 0 oxetan-2-yl
Ia.bl 128 O S 0 tetrahydrofuran-2-yl
Ia.bl 129 O S 0 tetrahydropyran-2-yl
Ia.bl 130 O S 0 - oxepan-2-yl
~
Ia.bl 131 O S O thiiran-2-yl
Ia.bl 132 O S O thietan-2-yl

005050080 CA 02377143 2001-12-19
No . ~ ~~ X Z Y U R6
Ia.bl 133 O S 0 tetrahydrothiofuran-2-yl
Ia.bl 134 O S O tetrahydrothiopyran-2-yl
5 Ia.bi 135 O S O thiepan-2-yl
Ia.bl 136 O S O oxetan-3-yl
Ia.bl 137 O S O tetrahydrofuran-3-yl
Ia.bl 138 O S O tetrahydropyran-3-yl
Ia.bl 139 O S O oxepan-3-yl
10
Ia.bl 140 O S O thiethan-3-yl
Ia.bl 141 O S 0 tetrahydrothiofuran-3-yl
Ia.bl 142 O S O tetrahydrothiopyran-3-yl
Ia.bl 143 O S O thiepan-3-yl
15Ia.bl 144 O S O tetrahydropyran-4-yl
Ia.bl 145 O S O oxepan-4-yl
Ia.bl 146 O S O tetrahydrothiopyran-4-yl
Ia.bl 147 O S O oxepan-4-yl
20Ia.bl 148 O S O tetrahydrothiopyran-4-yl
Ia.bl 149 O S O O CH3
Ia.bl 150 O S 0 O C2H5
Ia.bl 151 O S 0 O n-C3H~
25Ia.bl 152 O S O O i-C3H7
Ia.bl 153 O S O O cyclopropyl
Ia.bl 154 O S O COzH
Ia.bl 155 O S O C02CH3
Ia.bl 156 O S O C02C2H5
-_
30Ia.bl 157 O S O CHzCO2CH3
Ia.bl 158 O S O CH(CH3)C02CH3
Ia.bl 159 O S O O CH2C02CH3
Ia.bl 160 O S O O CH(CH3)C02CH3
35Ia.bl 161 O S 0 Cl
Ia.bl 162 O S O CN
Ia.bl 163 0 S O CH2C=CH
Ia.bl 164 O S O 0 CH2C~CH
40Ia.bl 165 O S O CHyOCH3
Ia.bl 166 O S O CHZCHzOCH3
Ia.bl 167 O S O O CHZCH20CH3
Ia.bl 168 O S O CHZ cyclopentyl
Ia.bl 169 O O O H
45
Ia.bl 170 O O O CH3
Ia.bl 171 O 0 0 n-C3H~

0050/50080
CA 02377143 2001-12-19
86
No . X Z Y U R6
Ia.bl 172 O O 0 i-C3H~
Ia.bl 173 O O O cyclopropyl
Ia.bl 174 O 0 0 n-C4H9
Ia.bl 175 O O O sec-C4Hg
Ia.bl 176 O 0 O 1-C4H9
Ia.bl 177 O O O t-C4H9
Ia.bl 178 O O O CH2 cyclopropyl
c clo entyl
Ia.bl 179 O O O Y p
Ia.bl 180 O O O cyclohexyl
Ia.bl 181 O O O oxiran-2-yl
Ia.bl 182 O O 0 oxetan-2-yl
Ia.bl 183 O O O tetrahydrofuran-2-yl
Ia.bl 184 O 0 O tetrahydropyran-2-yl
Ia.bl 185 O O O oxepan-2-yl
Ia.bl 186 O O O thiiran-2-yl
Ia.bl 187 O O O thietan-2-yl
Ia.bl 188 O O O tetrahydrothiofuran-2-yl
Ia.bl 189 O O O tetrahydrothiopyran-2-yl
Ia.bl 190 O O O thiepan-2-yl
Ia.bl 191 O O O oxetan-3-yl
Ia.bl 192 O O O tetrahydrofuran-3-yl
Ia.bl 193 O O O tetrahydropyran-3-yl
Ia.bl 194 O O O oxepan-3-yl
Ia.bl 195 O O 0 thiethan-3-yl
Ia.bl 196 O O O tetrahydrothiofuran-3-yl
Ia.bl 197 O O O tetrahydrothiopyran-3-yl
Ia.bl 198 O 0 0 thiepan-3-yl
Ia.bl 199 O O O tetrahydropyran-4-yl
Ia.bl 200 O O 0 oxepan-4-yl
Ia.bl 201 0 O 0 tetrahydrothiopyran-4-yl
Ia.bl 202 O O 0 oxepan-4-yl
Ia.bl 203 O O 0 tetrahydrothiopyran-4-yl
Ia.bl 204 O O 0 O CH3
Ia.bl 205 O 0 0 0 CZHS
Ia.bl 206 O O 0 O n-C3H~
Ia.bl 207 O O O 0 i-C3H~
Ia.bl 208 O 0 O O cyclopropyl
Ia.bl 209 O O 0 C02H
Ia.bl 210 O 0 O COzCH3

0050/50080
CA 02377143 2001-12-19
87
No . X Z Y U R6 -""
Ia.bl 211 0 O 0 C02C2H5
Ia. b1 212 0 O 0 CH2C02CH3
Ia.bl 213 0 0 O CH(CH3)C02CH3
Ia.bl 214 O O O O CHZCOZCH3
Ia.bl 215 O 0 O O CH(CH3)C02CH3
Ia.bl 216 O O O C1
Ia.bl 217 O O 0 CN
CH C~CH
Ia.bl 218 O o O 2
Ia.bl 219 O O 0 O CH2C=CH
Ia.bl 220 O O O CHaOCH3
Ia.bl 221 O O O C2H5
Ia.bl 222 O O O CH2CH20CH3
Ia.bl 223 O O O O CHZCH20CH3
Ia.bl 224 O O O CHZ cyclopentyl
Preference is furthermore given to the compounds Ib.bll to
Ib.b1224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
,H
~N
Z~N~C' ~ ~ I Ib.b~
U
YIURB
35
Preference is furthermore given to the compounds Ia.b21 to
Ia.b2224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
X
CI
la. b2
a
C02CH3 URs
Preference is furthermore given to the compounds Ib.b21 to
Ib.b2224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:

0050/50080
CA 02377143 2001-12-19
88
02CHa
N
~N~ ~~ ~ ~ Ib.b2
a C CI
X
VY
URB
Preference is furthermore given to the compounds Ia.b31 to
Ia.b3224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
X
I ~ ~ CI
N~~. _
~N ~ ~ ~ la.b3
a i
C02C2H5 ~ a
Preference is furthermore given to the compounds Ib.b31 to
Ib.b3224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
N
~N~ ~~ ~ ~ I Ib.b3
C C
\/ N
CURB
Preference is furthermore given to the compounds Ia.b41 to
Ia.b4224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CI
XI~
CI
N'
~ la.b4
~N O
a
C02Chi3 ~ s

0050/50080
CA 02377143 2001-12-19
89
Preference is furthermore given to the compounds Ib.b41 to
Ib.b4224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
C~2CH3
I
Ib.b4
Preference is furthermore given to the compounds Ia.b51 to
Ia.b5224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CI
X
CI
labs
ZEN
[
COaC2H5 YRe
Preference is furthermore given to the compounds Ib.b51 to
Ib.b5224, in which the variables X, Z, U and R6 each have the
meanings mentioned.in rows 1 to 224 of Table 2:
OaCxHs
N CI
~N\ ~~ / ~ Ib.bS
C CI
/N
Y'UR~
Preference is furthermore given to the compounds Ia.b61 to
Ia.b6224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
45

0050/50080
CA 02377143 2001-12-19
CI
I / ~ c1
~N~ '~ labs
N ~N
5 a
CN URs
10 Preference is furthermore given to the compounds Ib.bsl to
Ib.b6224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CN
N
15 ~ ~ Ib.bg
Preference is furthermore given to the compounds Ia.b71 to
Ia.b7224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
la.b~
Preference is furthermore given to the compounds Ib.b71 to
Ib.b~224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
O~C~NHC02CH3
CI
N Ib.b~
f
~N~ ~~ / ~ CI
C
I I
X
/N
YI~He

0050/50080
CA 02377143 2001-12-19
91
Preference is furthermore given to the compounds Ia.b81 to
Ia.bB224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CI
X
I ~ ~ CI
la.bB
a
URB
p' ~NHSOZCH3
Preference is furthermore given to the compounds Ib.bel to.
Ib.b8224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
O~ C~NHS02CH3
CI
Ib.be
uN~C~ ~ ~ CI
IXI
O' /'N
UY'RB
Preference is furthermore given to the compounds Ia.b91 to
Ia.b9224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
F
X / \
CI
~~~ _ la.b9
~N
~~02CH3 ~RB
Preference is furthermore given to the compounds Ib.b91 to
Ib.b9224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
45

CA 02377143 2001-12-19
92
O2rrf'13
N F
~N~ .~ ~ ~ Ib.bg
C CI
X
OY
URB
Preference is furthermore given to the compounds Ia.bl°1 to
Ia.bl°224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
F
X
~C\ ~ ~ CI
la.b~o
N N
~ ~~2C2H5 ~ 8
Preference is furthermore given to the compounds Ib.bl~l to
Ib.bl°224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
~ 02CZH5 .
N F
~N~ Ib.b~o
Preference is furthermore given to the compounds Ia.blll to
Ia.b11224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
F
X
CI
~N p ~ la.b~~
' /N
YIN
URg

0050/50080
CA 02377143 2001-12-19
93
Preference is furthermore given to the compounds Ib.blll to
Ib.b11224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CN
~ F
N
~N~ Ib.bl1
a
Preference is furthermore given to the compounds Ia.b121 to
Ia.b1z224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
F
X
I / ~ CI
la.bl2
Z'w/NI O / N
CHO
UR°
Preference is furthermore given to the compounds Ib.b121 to
Ib.b12224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
CHO
F
Z~N\C~a ~ ~ CI Ib.b~2
O' /'
~IU'RB
Preference is furthermore given to the compounds Ia.b131 to
Ia.b13224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
45

0050/50080
CA 02377143 2001-12-19
94
F
la.b~3
O~~~NHCOzCH3
Preference is furthermore given to the compounds Ib.b131 to
Ib.b13224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
O~NHC02CH3
F
Ib.b~3
~/N~C~ ~ ~ CI
I I
X
Preference is furthermore given to the compounds Ia.b141 to
Ia.b14224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
F
X
N~CL' ~ ~ CI
~ I ~ ~ la.b~4
W/N \ /N
CURB
O~~ ~NHSOaCH3
Preference is furthermore given to the compounds Ib.b141 to
Ib.b14224, in which the variables X, Z, U and R6 each have the
meanings mentioned in rows 1 to 224 of Table 2:
45

CA 02377143 2001-12-19
O~~C~NHS02CH3
N F
~N Ib.bya
5
Furthermore, preference is given to the compounds Ia.bls to Zal to
Ia.bls to za224 which differ from the compounds Ia.bl to 141 to Ia.bl
to 14224 only in that Y is S:
R3
l \ Ra
~N ~ la.b~s«xa
~Re
and the compounds Ib.bls to 2a1 to Ib.bls to 2a224 which differ from
the compounds Ia.bls to 2a1 to Ia.bls to 2e224 only in that the N
substituents are inverted:
R
Ra
~N~ .~ / \ a Ib.b~s~o2s
a C R
S~N
~~U('Rs
Moreover, particular preference is given to the substituted ureas
of the formula Ia.cl
R3
X
~~. / \ a
~N p R la.c~
w/ ~R N~~'
URB

0050/50080
CA 02377143 2001-12-19
96
in particular tv the compounds listed in Table 3 below:
Table 3
R R 3 4 U R 6
No R Y
.
~Z
X
I a.cl 1 S H H C 1 H
O O
I a.cl 2 S H H C l C H3
O O
I a.cl 3 S H Cl O C 2H5
O H
I a'cl 4 O S H C l O n-C3H~
H
Ia.cl O S H H Cl O i-C3H7
5
Ia.cl O S H H Cl O cyclopropyl
6
Ia.cl O S H H Cl O n-C4Hg
7
Ia.cl O S H H C1 O sec-C4Hg
8
Ia.cl O S H H Cl O i-C4Hg
9
Ia.cl O S H H Cl O t-C4Hg
10
Ia.cl O S H H Cl O CH2 cyclopropyl
11
Ia.cl O S H H C1 0 cyclopentyl
12
Ia,cl O S H H C1 0 cyclohexyl
13
Ia.cl O S H H C1 O oxiran-2-yl
14
Ia.cl O S H H Cl O oxetan-2-yl
15
Ia.cl O S H H Cl O tetrahydrofuran-2-yl
16
Ia.cl O S H H C1 O tetrahydropyran-2-yl
17
Ia.cl O S H H C1 0 oxepan-2-yl
18
Ia.cl O S H H C1 O thiiran-2-yl
19
Ia.cl O S H H C1 O thietan-2-yl
20
Ia.cl O S H H C1 O tetrahydrothiofuran-2-yl
21
tetrah drothio ran-2 1
Ia.cl O S H H C1 O Y pY -y
22
Ia.cl O S H H C1 O thiepan-2-yl
23
Ia.cl O S H H C1 O oxetan-3-yl
24
Ia.cl O S H H C1 O tetrahydrofuran-3-yl
25
Ia.ci O S H H G1 O tetrahydropyran-3-yl
26
Ia.cl O. S H H C1 0 oxepan-3-yl
27
Ia.cl O S H H C1 O thiethan-3-yl
28
Ia.cl O S H H C1 O tetrahydrothiofuran-3-yl
29
Ia.cl O S H H C1 0 tetrahydrothiopyran-3-yl
30
Ia.cl O S H H C1 O thiepan-3-yl
31
Ia.cl O S H H Cl O tetrahydropyran-4-yl
32
Ia.cl O S H H C1 O oxepan-4-yl
33
Ia.cl 0 S H H C1 O tetrahydrothiopyran-4-yl
34
Ia.cl O S H H C1 O oxepan-4-yl
35
Ia.cl O S H H C1 O tetrahydrothiopyran-4-yl
36

0050/50080
CA 02377143 2001-12-19
97
No Z X R R3 R4 Y U R6
.
Ia.cl O S H H C1 O 0 CH3
37
Ia.cl O S H H C1 O O C2H5
38
Ia.cl O S H H C1 0 0 n-C3Hy
39
Ia.cl O S H H C1 O O i-C3H~
40
Ia.cl O S H H Cl 0 O cyclopropyl
41
Ia.cl O S H H C1 O COZH
42
Ia.cl O S H H C1 0 C02CH3
43
Ia.cl O S H H Cl O C02C2H5
44
Ia.cl O S H H C1 O CHZC02CH3
45
Ia.cl O S H H C1 O CH(CH3)C02CH3
46
Ia.cl O S H H C1 0 O CH2C02CH3
47
5 Ia.cl O S H H C1 O O CH(CH3)COyCH3
48
Ia.cl 0 S H H Cl O C1
49
Ia.cl O S H H C1 O CN
50
Ia.cl O S H H C1 O CH2CCH
51
Ia.cl O S H H C1 O 0 CH2C~CH
52
Ia.cl O S H H Cl O CH20CH3
53
Ia.cl O S H H C1 O CH2CH20CH3
54
Ia.cl O S H H C1 O 0 CHZCH20CH3
55
Ia'cl O S H H C1 O CH2 cyclopentyl
56
35
45

0050'SOO8o CA 02377143 2001-12-19
98
Moreover, preference is given to the compounds Ib.cll to Ib.c156
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted:
4
R
Ib.c~
U R°
Moreover, preference is given to the compounds Ia.c21 to Ia.cz56
which differ from the compounds Ia.cll to Ia.c156 only in that R
is COZCH3:
X
~C~ ~ ~ CI
la.c2
I~/I N ~
C02CH3 ~ a
Moreover, preference is given to the compounds Ib.c21 to Ib.cz56
which differ from the compounds Ia.cll to Ia.cl56 only in that the
N substituents are inverted and R is C02CH3:
2 5 ~ 02CH3
N
~N~ ~~
C CI
X
30, N'\ 'O
'U~Re
Moreover, preference is given to the compounds Ia.c31 to Ia.c356
which differ from the compounds Ia.cll to Ia.c156 only in that R
35 is C02CH3 and R3 is Cl:
CI
X
CI
~N ~ la.c3
40 ~I N ~ O
C02CH3 uRe
Moreover, preference is given to the compounds Ib.c31 to Ib.c356
which differ from the compounds Ia.cll to Ia.c156 only in that the
45 N substituents are inverted and R is COZCH3 and R3 is C1:

~~50~,c~~80 CA 02377143 2001-12-19
99
C02CH3
CI
I
~N~ ~~
CI Ib.c3
Nw
a
Moreover, preference is given to the compounds Ia.c41 to Ia.c456
which differ from the compounds Ia.cll to Ia.c156 only in that R
is COZC2H5 and R3 is C1:
CI
X
I
CI
~N ~ la.c4
UN N ~ O
COZC2H5
Moreover, preference is given to the compounds Ib.c41 to Ib.c456
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted and R is COZC2H5 and R3 is C1:
~2''2H5
N CI
~N~ .~
2 5 ~ CI Ib.c4
N\'O
~U R°
Moreover, preference is given to the compounds Ia.c51 to Ia.c556
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHCOzCH3 and R3 is C1:
C!
X
~~~ ~ ~ CI
N
~N ~ N O la.c5
~RB
O~' ~NHC02CH3
Moreover, preference is given to the compounds Ib.csl to Ib.c556
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted and R is C(O)NHC02CH3 and R3 is C1:

0050/50080
CA 02377143 2001-12-19
100
NHC02CH3
CI
~N~ ~~
C CI Ib,cs
URe
Moreover, preference is given to the compounds Ia.csl to Ia.c656
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHS02CH3 and R3 is C1:
CI
X
I ~ ~ CI
lace
~N N_'
Y'URB
O' ~NHS02CH3
Moreover, preference is given to the compounds Ib.c61 to Ib.c656
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents .are inverted and R is C(O)NHSOZCH3 and R3 is C1:
O~~C~NHSOZCH3
CI Ib,cs
Moreover, preference is given to the compounds Ia.c71 to Ia.c756
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C02CH3 and R3 is F:
F
X
~N~CL\~ ~ ~ CI
hiI
ZEN N \ O la.c~
C02CH3 ~ a
Moreover, preference is given to the compounds Ib.c71 to Ib.c756
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted and R is C02CH3 and R3 is F:

005050080 CA 02377143 2001-12-19
101
OaCHs
N F
I
~N~
C ~ ~ CI Ib.d
X
N \ 'O
IYU Rs
Moreover, preference is given to the compounds Ia.c81 to Ia.c856
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C02CZH5 and R3 is F:
F
X
~C~ ~ ~ CI
~N ~ N O lace
C02C2H5
Moreover, preference is given to the compounds Ib.c81 to Ib.c856
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted and R is C02C2H5 and R3 is F:
OzCzHs
~N F
I
Z~N~C'~ ~ ~ CI Ib.cB
X
N \ 'O
~'U'Rs
Moreover, preference is given to the compounds Ia.c91 to Ia.c956
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHC02CH3 and R3 is F:
F
X
~C~ ~ ~ CI
N
~N ~ N O la.c9
O~' ~NHCOZCH3
Moreover, ~~ef=rence is given to the compounds Ib.c91 to Lb.cg56
which d.it_~swum the compounds Ia.cl1 to Ia.c156 only ~u r_hat the
N subst:i t!_i:~:1'~.~ a re inverted and R is C ( O ) NHCOZCH3 and E? ' ., F

0050/50080
CA 02377143 2001-12-19
102
O\~C~NHC02CH3
F
I H
Z~N~C~b / ~ CI Ib.c9
11
X
N~O
~U'Rs
Moreover, preference is given to the compounds Ia.cl°1 to
Ia.cl°56
which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHSO2CH3 and R3 is F:
F
CI
1 !, ~ I 1 la.c~o
U RB
NHS02CH3
Moreover, preference is given to the compounds Ib.clll to Ib.c1156
which differ from the compounds Ia.cll to Ia.c156 only in that the
N substituents are inverted and R is C(O)NHS02CH3 and R3 is F:
O\~C~NHS02CH3
~N F
I H
Z~N~C'~ ~ ~ CI Ib.co
i1
X
N\'O
3 0 C'U'RB
Moreover, preference is given to the compounds Ia.clz to zzl to
Ia.clz to zz56 which differ from the compounds Ia.cl to ill to Ia.cl
to 1156 only in that Y is S:
R
X
Il ~ \ Ra
~'~N'C~N
I H la.c~2 co 22
ZuN~R N w S
Moreover, preference is given to the compounds Ib.clz ~° -''~ to
Ib.clz to zz56 c.rhich differ from the compounds Ia.cl t° '-- l to
Ia.c
to m56 only in that the t7 substituents are inverted anc: Y L~ 5:

CA 02377143 2001-12-19
143
a
Ib.c~ztozz
Moreover, preference is given to the compounds Ia.c23 to 331 to
Ia.c23 to x356 which differ from the compounds Ia.cl to 111 to Ia.cl
to 1156 only in that X is 0:
R3
O
N~C' ~ ~ Ra
la.czs to 33
~N
w/ ~R N~S
U RB
Moreover, preference is given to the compounds Ib.c23 to 331 to
Ib.c23 to 3356 which differ from the compounds Ia.cl to 111 to Ia.cl
to 1156 only in that the N substituents are inverted and X is O:
~N~R Rs
a
z~N~C~ ~ ~ R4 Ib.C23to33
O
2 5 N \ 'S
IYURe
Moreover, preference is given to the compounds Ia.c34 to 441 to
Ia.c34 to 4456 which differ from the compounds Ia.cl to 111 to Ia.cl
to 1156 only in that Z is S
R3
O
~N~C\N ~ ~ R4
S~~\N~ H N S la.c3atoa4
R Y
UR
Moreover, preference is given to the compounds Ib.c34 to 441 to
Ib.c34 to 4456 which differ from the compounds Ia.cl to 111 to Ia.c1
to 1156 only in that the r1 substituents are inverted and Z is S:

0050/50080
CA 02377143 2001-12-19
104
~NiR Ra
I
S~N~Cr~~ / ~ R4 Ib.Ca4to44
I I
O
N'\'S
~5
UR6
Moreover, particular preference is given to the substituted ureas
of the formula Ia.dl
Ra
X
~N~ ~~ la.d~
I
Z~N~R
~~ O
in particular to the compounds listed in Table 4 below:
Table 4
No Z X R R3 Y T R7
. O S H H O CH3
dl 1
Ia
. O S H H O C2H5
dl 2
Ia
. O S H H O n-C3H7
Ia
dl 3
. O S H H O cyclopropyl
dl 4
Ia
. O S H H O n-C4H9
dl 5
Ia
. O S H H O sec-C4H9
dl 6
Ia
. O S H H O t C4H9
dl 7
0 Ia
. O S H H O CH2-CH=CHz
3
dl 8
Ia
. O S H H O CHz-C=CH
d1 9
Ia
. O S H H O CH2CH2C1
dl 10
Ia
. O S H H O CHZCH20CH3
dl 11
Ia
~ O S H H O CH2CHZCN
dl 12
Ia
. O S H H O H
dl 13
Ia
. O S H H O O H
dl 14
Ia
. O S H H 0 0 CH3
dl 15 _
Ia
. O 0 CzHs
O S H H
d1 16
Ia
. O S H H O O n-C3H7 _
dl 17
Ia
. O S H H - 0 cyclopropyl
dl 18 0 _j
Ia
. O S H H 0 C) n-C4H9 .~_.
dl 19
Ia
. O S H H 0 0 sec-C4H9 _~._
~S Ia
d'- 20
. O S H H - 0 ~ t C4H9 ~~-_
Ia.dl 21 -- O

0050/50080
CA 02377143 2001-12-19
105
No . Z X R Rs Y T R7
Ia.dl 22 O S H H O O CH2-CH=CH2
Ia.dl 23 O S H H O O CH2-C=CH
Ia. dl O S H H O O CH2CH2C1
24
Ia.dl 25 O S H H O O CHZCHZOCH3
Ia.dl 26 0 S H H 0 0 CHZCHZCN
Ia.dl 27 O S H H O O i-C3H7
Ia.dl 28 O S H H O 0 i-C4Hg
Ia.dl 29 O S H H 0 i-C3H7
Ia.dl 30 O S H H O i-C4Hg
Ia.dl 31 O S H H O O CH2COZCH3
Ia.dl 32 O S H H O O CH(CH3)C02CH3
Ia.dl 0 S H H 0 O CH(CH3)C02C2H5
33
Ia.dl 34 O S H H 0 CHZCOZCH3
Ia.dl 35 O S H H O CHzC02-n-C3H7
Moreover, preference is given to the compounds Ib.dll to Ib.d135
which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted:
N~R Rs
~N~ .~
C Y Ib.d~
1'R' O
30-Moreover, preference is given to the compounds Ia.dzl to Ia.d235
which differ from the compounds Ia.dll to Ia.d135 only in that R
is COZCH3:
R3
X
II ~ \
~N~C~~ Y la.dz
HI
Z~N~C02CH3 N
TR'
4~ Moreover, preference is given to the compo~_mds Ib.d21 to Ib.dz35
vahich differ from the compounds Ia.dl1 to :~a.d'-35 only in that the
r1 substituents are inverted and R is CO~C~I-j v

005050080 CA 02377143 2001-12-19
106
OxCHa
N R3
Ir _ I H
zuN~C.~ / ~ Y
I I Ib.d2
X
0
Moreover, preference is given to the compounds Ia.d31 to Ia.d335
which differ from the compounds Ia.dll to Ia.d135 only in that R
is C02CH3 and R3 is C1:
CI
X
~N~~\~ / ~ Y la.d3
Zu'N~C0h2iCH3 ~V
O
Moreover, preference is given to the compounds Ib.d31 to Ib.d335
which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted and R is C02CH3 and R3 is C1:
OZCH3
~N CI
I H
zuN~C~~ / ~ Y
X Ib.d3
O
Moreover, preference is given to the compounds Ia.d41 to Ia.d435
which differ from the compounds Ia.dll to Ia.d135 only in that R
is COZC2H5 and R3 is C1:
CI
X
~N~C\~ / ~ Y la.d4
3 5 Z~N~COZCzHS ~J
O
t~toreover, preference is given to the compounds Zb.d41 to Ib.d435
~~h.ich differ from the compounds Ia.dll to Ia_d135 only in that the
c1 subst.:ituents are inverted and R is CU~C ~H~ ~~nd Rj is C1
~5

0050~5008~ CA 02377143 2001-12-19
1~7
Z~
Ib,d4
Moreover, preference is given to the compounds Ia.d51 to Ia.d535
which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(O)NHC02CH3 and R3 is Cl:
CI
X
N'~~~ / \ Y la.d5
~N
a
O
.. .
O NHC02CH3
Moreover, preference is given to the compounds Ib.d51 to Ib.d535
which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted and R is C(O)NHC02CH3 and R3 is C1:
O\~C~NHC02CH3
CI
~I
~N.C~ / \ ~, Ib.ds
I I
X
O
Moreover, preference is given to the compounds Ia.dsl to Ia.d635
which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(0)NHS02CH3 and R3 is C1:
CI
X
~~' / \
~N ~ la.dd
. ZEN
0
O' ~NHSOZCH3
ivloreo~rer, preference is given to the compounds Ib.d«L to Ib.dti35
;,rhich differ from the compounds Ia.dl1 to Ia.a:-5 only in that the
~1 substituents are inverted and R is C(O)NHSO::~:E~3 .~{ad R3 is C1:

0050~5~080 CA 02377143 2001-12-19
l~$
O\ C~NWS02CH3
CI
~N~ .N ~ ~ Ib.de
v C Y
O
Moreover, preference is given to the compounds Ia.d71 to Ia.d~35
which differ from the compounds Ia.dll to Ia.d135 only in that R
is COzCH3 and R3 is F:
F
X
N~C~~ / \ Y la.d~
~N~C02CH3
O
Moreover, preference is given to the compounds Ib.d71 to Ib.d735
which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted and R is C02CH3 and R3 is F:
02CHs
~N F
I H
zuN~C~~ I ~ Y
II Ib.d~
X
O
Moreover, preference is given to the compounds Ia.dgl to Ia.d835
which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is COZCZH5 and R3 is F:
F
X
~N~C~~ ~ ~ Y lade
Z~N~C0h2iCzH5 ~J
TR' O
Moreover, preference is given to the compounds Ib.dgl to Ib.d835
which differ from the compounds Ia.dll to Ia.d1 35 only in that
the N substituents are inverted and R is CO?C-~H; and R' is F:

CA 02377143 2001-12-19
109
Ib.de
O
Moreover, preference is given to the compounds Ia.d91 to Ia.d935
Which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(O)NHCHZCH3 and R3 is F:
F
X
la. d9
~N
ZuN
O' ~NHC02CH3
Moreover, preference is given to the compounds Ib.d91 to Ib.d935
Which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted and R is C(O)NHCOZCH3 and R3 is F:
O\~C~NHC02CH3
Ib.d9
Moreover, preference is given to the compounds Ia.dl°1 to
Ia.dl°35
which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is C(O)NHSOZCH3 and R3 is F:
F
X
I I
N~C~N _ Y la.d~o
~N H
TRH O
O' C~NHSOZCH3
Moreover, preference is given to the compounds Ib,d'-'1 to Ib.d935
which differ :from the compounds Ia.dll to Ia.d'-?5 onl~~ in that the
N substituents are in=ferted and R is C(O)NHSOZCH_~ and R3 is F:

CA 02377143 2001-12-19
fb,d~~
Moreover, preference is given to the compounds Ia.dlll to Ia.d1135
Which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is COZCH3, R3 is F and Y is S:
F
X
' /_\ S la.d~,
Z~ 'CO~H3 ~ ~ O
Moreover, preference is given to the compounds Ib.dlll to Ib.d1135
Which differ from the compounds Ia.dll to Ia.d135 only in that the
N substituents are inverted and R is COzCH3, R3 is F and Y is S:
~CO~H3
~N F
I
Z~-N~~'b i v
~~ Ib.d~~
X
N
O
Moreover, preference is given to the compounds Ia.dlz to z21 to
Ia.dlz to z235 which differ from the compounds Ia.dl to 111 to Ia.dl
to 1135 only in that X is O:
R3
O
N'C'N / \ Y la.d~zcozz
W H
Z~N'R
TR' O
Moreover, preference is given to the compounds Ib.dlz to z21 t o
4p Ib.dlz to 2z35 which differ from the compounds Ia.d1 to '11 to Ia.dl
to 1135 only in that the N substituents are inverted and X is 0:
~1~
n muen ~u

4
CA 02377143 2001-12-19
111
N~H R3
~N~
C Y
I I
O
0
Ib.d~2 to ii
Moreover, preference is given to the compounds Ia.d23 to 331 to
Ia.d23 to 3335 which differ from the compounds Ia.dl to 111 to Ia.dl
to 1135 only in that Z is S:
R3
X
I
~ Y
_N ~ la.d23to33
\R ~~ O
Moreover, preference is given to the compounds Ib.d23 to 331 to
Ib.dz3 to 3335 which differ from the compounds Ia.dl to 111 to Ia.dl
to 1135 only in that the N substituents are inverted and Z is S:
-
N'
N
a
I b.d23 to 33
Moreover, particular preference is given to the substituted ureas
of the formula Ia.el
R3
X
I I
~N~C~~ Y la.e~
Hl
ZuN~R N~O
TR'
in particular to the compounds listed in Table 5 below:
Table 5
No . Z X R R3 Y T R7
~
Ia.el 0 S H H 0 CH3
1
Ia.el 0 S H H O C~H
2
Ia.el O S H H O w -C3H~
3 ~
Ia.e1 O S H H 0 cyclopropyl
4 -
Ia.el 0 S H H 0 n-C4H9
5 -
Ia.el O S H H O sec-C~H9
6

CA 02377143 2001-12-19
112
No Z X R R3 Y T R7
Ia.el O S H H O t-C4H9
7
Ia.el O S H H O CH2-CH=CH2
8 .
Ia.el O g H H ~ CHZ_~~CH -.
9
Ia.el O S H H O CH2CHZC1
Ia.el O S H H O CHZCH20CH3
11
Ia.el O S H H O CHZCH2CN
12
Ia.el O S H H O H
13
10
Ia.el O S H H O O H
14
Ia. e1 O S H H O O CH3
Ia.el O S H H O 0 CZH5
16
Ia.el O S H H O O n-C3H7
17
15 Ia.e1 O S H H O O cyclopropyl
18
Ia.el O S H H O O n-C4H9
19
Ia.el O S H H O O sec-C4H9
Ia.el O S H H O O t-C4H9
21
20 Ia.el O S H H O O CHZ-CH=CH2
22
Ia.el O S H H O O CH2-C=-CH
23
Ia.el O S H H O O CH2CH2C1
24
Ia.el 0 S H H O O CHZCH20CH3
25 Ia.el O S H H O O CH2CHZCN
26
Ia.el O S H H O O i-C3H7
27
Ia.el O S H H O O i-C4H9
28
Ia.el O S H H O i-C3H7
29
Ia.el O S H H O i-C4H9
30 Ia.el O S H H O O CHZC02CH3
31
Ia.el O S H H O O CH(CH3)COZCH3
32
Ia.el O S H H O O CH(CH3)C02CZH5
33
Ia.el 0 S H H O CHZCOZCH3
34
Ia.el O S H H O CHzC02-n-C3H7
35
Moreover., preference is given to the compounds Ib.ell to Ib.e135
which differ from the compounds Ia.el1 to Ia.e135 only in that the
N substituents are inverted:
~N~R R\,,
z N~ _ i J, ,
Ib.e~
,N ' 0
TR'

CA 02377143 2001-12-19
113
Moreover, preference is given to the compounds Ia.e21 to Ia.e235
which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3:
R3
~N' '~ Y la.ez
ZZ - 'O
~N'C02CH3 TR'
Moreover, preference is given to the compounds Ib.e21 to Ib.e235
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is COZCH3:
OzCHs
N R3
~N'
C ~ Ib.ez
N O
TRH
Moreover, preference is given to the compounds Ia.e31 to Ia.e335
which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3 and R3 is C1:
CI
X
~N' '~ Y la.e3
Z~N'COZCH3 N 7
~O
TR
Moreover, preference is given to the compounds Ib.e31 to Ib.e335
which differ from the compounds Ia.el 1 to Ia.el 35 only in that
the N substituents are inverted and R is C02CH3 and R3 is C1:
COZCH3
CI
H
ZuN'C'N
Ib.e3
N- \O
T R'
Moreover, preference is given to the compounds Ia.e=~1 to Ia.e435
~rhich differ from the compounds Ia.el1 to Ia.e135 only in that R
is CO~C~E!5 and R3 is Cl:

0050/50080 CA 02377143 2001-12-19
114
CI
X
I ~ \
' _ Y la.e~
~N' ~ ~N~O
~ C02C2H5 TR'
Moreover, preference is given to the compounds Ib.e41 to Ib.e435
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C02C2H5 and R3 is C1:
~ OzCzHs
~N CI
I H
zuN~C~~
Y lb.e4
1.5 TRH O
Moreover, preference is given to the compounds Ia.e51 to Ia.e535
which differ from the compounds Ia.ell to Ia.e135 only in that R
is C(O)NHCOzCH3 and R3 is C1:
CI
X
I I
~N~C'~ Y la.es
~Z~N Fi N' \ O
TR'
O NHC02CH3
Moreover, preference is given to the compounds Ib.esl to Ib.e535
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C(O)NHCOzCH3 and R3 is Cl:
O\~C~NHCOZCH3
CI
~I H
z~N~C~~ ~ \ Ib.es
X Y
N~O
TR'
Moreover, preference is given to the compounds Ia.e61 to Ia.e535
which differ from the compounds Ia.e'-1 to Ia.e135 only in that R
is C ( O ) NHSC~~CH3 and R3 is C1:

CA 02377143 2001-12-19
m
c1
x
c
~N~ '~ Y la.ee
LAN N!- 'O
TR'
O' 'NHS02CH3
Moreover, preference is given to the compounds Ib.e61 to Ib.e635
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C(O)NHS02CH3 and R3 is C1:
O~ C~NHS02CH3
CI
~N' ,N ~ ~ Ib.ee
C y
X ~
N' 'O
TR'
Moreover, preference is given to the compounds Ia.e71 to Ia.e735
which differ from the compounds Ia.ell to Ia.e135 only in that R
is COzCH3 and R3 is F:
F
X
C
N. '~ Y la.e~
~N' N~O
C02CH3 TR'
Moreover, preference is given to the compounds Ib.e71 to Ib.e735
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is COZCH3 and R3 is F:
C02CH3
~N F
I ~
ZuN'C
X Y Ib.e~
N- '' O
TR'
Moreover, preference is given to the compounds Ia.esl to Ia.e~35
which differ from the compounds Ia.ell to Ia.eL3~ only in than
is COzCzHS and R3 is F:

0050/50080
CA 02377143 2001-12-19
116
F
X
NBC' ~ ~ ~' la.ee
~N~ ~ ~N~O
CO2C2H5 TR'
Moreover, preference is given to the compounds Ib.eel to Ib.e835
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is COZCZHS and R3 is F:
~ 02CZH5
N F
~N~
a
C ~ Ib.ee
NI O
TR'
Moreover, preference is given to the compounds Ia.e91 to Ia.e935
which differ from the compounds Ia.ell to Ia.e135 only in that R
1s C(O)NHC02CH3 and R3 is F:
F
X
I I
Y la. e9
~N ~ N' \O
2 5 TRH
O NHC02CH3
Moreover, preference is given to the compounds Ib.e91 to Ib.e935
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C(O)NHCOZCH3 and R3 is F:
O\~C~NHC02CH3
F
~N~ ~~ / ~ ib.e9
~Y
N O
T~R'
Moreover, preference is given to the compounds Ia.el°1 to
Ia.e1°35
which differ from the compounds Ia.ell to Ia.e135 only in that R
is C(O)DIHSOzCH3 and R' is F:

0050~50~8~ CA 02377143 2001-12-19
117
F
X
NBC' ~ ~ Y la.e~o
~N N' \O
TR'
O' NHS02CH3
Moreover, preference is given to the compounds Ib.el~l to Ib.e1~35
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C(0)NHS02CH3 and R3 is F:
O\~C~NHS02CH3
F
~N~ ~~ ~ ~ Ib.e~o
I
TR'
Moreover, preference is given to the compounds Ia.elll to Ia.e1135
which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3, R3 is F and Y is S:
F
X
N~C~ / \ S la.e~~
~ I
Z~N~COzCH3 TR' O
Moreover, preference is given to the compounds Ib.elll to Ib.e1135
which differ from the compounds Ia.ell to Ia.e135 only in that the
N substituents are inverted and R is C02CH3, R3 is F and Y is S:
OzCHa
~N F
I
Z~N'C/ / \ S Ib.e"
X ~
N' \ O
TR'
NSoreover, preference _Ls given to the compounds Ia.el2 to 221 to
Ia.el2 to 2235 which dif.~er from the compounds Ia.el to 111 to Ia.e
to 1135 only in that x ; ~ O:

if
0050/50080
CA 02377143 2001-12-19
118
R3
O
,I~ ~ \
N~~~~ Y la.e~zcc2x
~N~ H N' \O
a R ~R~
Moreover, preference is given to the compounds Ia.elz to zzl to
Ia.elz to z235 which differ from the compounds Ia.el to 111 to Ia.el
to 1135 only in that the N substituents are inverted and X is O:
~N~R
I
~N~~~ Ib.e~2~o2z
X
Moreover, preference is given to the compounds Ia.ez3 to 331 to
Ia.ez3 to 3335 which differ from the compounds Ia.el to 111 to Ia.el
to 1135 only in that Z is S:
Rs
X
,I~
N~~~~ / \ Y la.e2s~aas
~N~ H N' \O
R TR'
Moreover, preference is given to the compounds Ia.ez3 to 331 to
Ia.ez3 to ss35 which differ from the compounds Ia.el to 111 to Ia.el
to 1135 only in that the N substituents are inverted and Z is S:
~R Rs
N
I
~N, ~b I \
Ib.e23 to 3a
N' \ O
T R'
Moreover, particular preference is given to the substituted ureas
oz the formula Ia.fl
R3
~~ / \ R'
~..ns! ~H
la.f~
Z~.. ~I .. ~ O
O~'
Rs~~Ra
in particular to the compof.incls listed in Table 5 below:

0050/50080
CA 02377143 2001-12-19
119
Table 6
N Z X
R R3 R4. R8 R9
o. 0 S H H G1 H H
fl l
Ia. 0 S H H C1 H CH3
f12
Ia. O S H H C1 H G2H5
f13
I
a. O S H H C1 H n-G3H7
f14
Ia. 0 S H H C1 H i G3H7
f15
I
a. O S H H C1 H n-C4H9
f16
I
a. O S H H C1 cyclopropyl H
f17
I
a. O S H H C1 CH3 H
flB
I
a. O S H H C1 CH3 CH3
f19
I
a. O S H H C1 CZHS H
f110
I
a. O S H H C1 C2H5 GH3
flll
I
a. O S H H C1 n-C3H7 C2H5
f112
I
a. O S H H C1 n_C3H7 n_C3H7
f113
Ia. O S H H C1 C1 H
f114
I
a. O S H H C1 H C1
Ia.f115 O S H H Cl C1 CH3
f116
I
a. O S H H C1 _____ Cep) _____
f117
Ia. O S H H C1 CH3 CHZCHZC1
f118
I
a. 0 S H H C1 C2H5 G2H5
f119
I
a. O S H H C1 i-C3H7 1-C3H7
f120
I
a. O S H H C1 i C3H7 H
f121
Ia.
Moreover, preference is given to the compounds Ib.fll to Ib.f121
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted:
NCR
~I H
Ib.f~
O
O
Rs ~~d
Moreover, preference is given to the compounds Ia.f21 to Ia.f221
T:rhich differ from the compounds Ia.fll to Ia.f121 only in that R
is COZCH3:

0050/50080 CA 02377143 2001-12-19
120
R3
X
R4 la.i~
~N
~ ~C02CH3 O
O
Rs" RB
Moreover, preference is given to the compounds Ib.f21 to Ib.f221
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C02CH3:
02CHa
Ra
C R Ib.f~
O
O
Rs~Re
Moreover, preference is given to the compounds Ia.f31 to Ia.f321
which differ from the compounds Ia.fll to Ia.f121 only in that R
is C02CH3 and R3 is Cl:
CI
X
II / \ Ra
2 5 . C. I a.f3
~N
Z~N~C02CH3 O
O
Rs~Re
Moreover, preference is given to the compounds Ib.f31 to Ib.f321
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is COZCH3 and R3 is Cl:
COZCH3
3 5 ~ CI
\
C R
Ib.fa
X
O
O\~
Rs~Rs
P-Ioreover, preference is given to the compounds Ia.f'~l to Ia.f421
which ~~tiffer from the compounds Ia.fLl to Ia.f121 only in that R
is CO-~C:ZH~ and R3 is C1:

0050/50080
CA 02377143 2001-12-19
121
CI
x
N~C~~ R la.f4
N. 0
a COzCxHs
~
Rs~Re
Moreover, preference is given to the compounds Ib.f41 to Ib.f421
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C02CzH5 and R3 is Cl:
IC02C2Hs
N CI
~N. .~ ~ ~ Ra
C . I b.f4
X
O
O
Rs~Rs
Moreover, preference is given to the compounds Ia.f51 to Ia.f521
which differ from the compounds Ia.fll to Ia.f121 only in that R
is C(O)NHC02CH3 and R3 is Cl:
CI
X
I / \ R4 la.fs
N'
O
O
Rs~Ra
O' ~NHC02CH3
Moreover, preference is given to the compounds Ib.f51 to Ib.f521
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C(O)NHCOZCH3 and R3 is Cl:
3 5 O ~C~NHCOZCH3
CI
~N. ~~ ~ ~ R,, Ib.fs
C
I I
X
O
O
Rs~Re
Mo.reove ~_~ . creference is given to the compounds Ia. f° 1 to -.C-
__m. f621
which differ L-rom the compounds Ia.fll to Ia.f121 only ~..n that R
is C ( O ) C1H~'yCu; and R3 is C1:

CA 02377143 2001-12-19
122
CI
X
Irl ~ \ Ra
Ia.fe
O
O~~
Rs~Ra
3
Moreover, preference is given to the compounds Ib.fsl to Ib.f621
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C(O)NHS02CH3 and R3 is Cl:
O\ C~NHS02CH3
CI
Z~N~C~~ ~ \ Ra Ib.fs
O
O~~
Ra/''Ra
Moreover, preference is given to the compounds Ia.f71 to Ia.f721
which differ from the compounds Ia.fll to Ia.f121 only in that R
is COZCH3 and R3 is F:
F
X
\ Ra la.f~
~N
~C02CH3 O
O
R9"Ra
Moreover, preference is given to the compounds Ib.f~l to Ib.f721
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is COZCH3 and R3 is F:
~ 02CH3
~N HF
I
Z~N~C~~ ~ \ Ra
II Ib.f~
X
O
O
Rs~Ra
Moreover, prezerence is given to the compounds Ia.f~l to Ia.~=~'<1
which differ srom the compounds Ia.fll to Ia.f121 on:Ly in .-.nat R
is C02CZH5 r:lnd R-'' is F

0050/50080
CA 02377143 2001-12-19
123
F
X
ICI ~ \ Ra
la.fe
~N
uN~C02C2H5 O O
Rs~Re
Moreover, preference is given to the compounds Ib.fel to Ib.f821
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C02C2H5 and R3 is F:
O2C2H5
N F
I
N~ ~~ ~ \ a
C R Ib.fe
X
O
O
Rs~Ra
Moreover, preference is given to the compounds Ia.f91 to Ia.f921
which differ from the compounds Ia.fll to Ia.f121 only in that R
is C(O)NHC02CH3 and R3 is F:
F
X
ICI / \ Ra
N~ ~N la.fs
N H
O
OJ
Rs~Rs
O C~NHC02CH3
Moreover, preference is given to the compounds Ib.f91 to Ib.f921
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C(0)NHCOZCH3 and R3 is F:
3 5 ~ C~NHCO2CH3
F
~I
zVN~C~~ ~ \ R.v Ib.fs
1 I
X
O
O
R9" Rg
Moreover, prefereclce i.s given to the compounds Ia. fl°1 to Ia.
f'-°~ 'L
cahieh differ from. W?_~ compounds Ia.fll to Ia.f121 only in that
is C ( O ) NHSOzCH; anti R.= is F

0050/50080
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124
F
X
ICI / \ Ra
~N~ ~~ la.f~o
ZEN p
O
Re~Ra
O' ~NHS02CH3
Moreover, preference is given to the compounds Ib.flol to Ib.flo21
which differ from the compounds Ia.fll to Ia.f121 only in that the
N substituents are inverted and R is C(O)NHS02CH3 and R3 is F:
O~ ~NHS02CH3
~C
F
~N\ ~a ~ \ a Ib.flo
a C R
I I
X
O
O~
Rs~Re
Moreover, preference is given to the compounds Ia.fll to 201 to
Ia. fli to 2021 which differ from the compounds Ia. fl to 101 to Ia. fl
to 1021 only in that X is O:
2 5 Ra
O
II ~ \ Ra
~N~C~~ la.fic co zo
Z~N~R Fi O
O\~
3 0 Rs~Ra
Moreover, preference is given to the compounds Ib.fl1 to 201 to
Ib.fli to 2o21 which differ from the compounds Ia.fl to lol to Ia.fl
to 1021 only in that the N substituents are inverted and X is O:
~R Rs
N
I
N
Z~ \C~ / \ Ra Ib.f» ca zo
O
O
O\~
Rs~Ra
a.to.reover, preference is given to the compounds Ia.fzi to 301 to
_L3. f2i to 3021 which differ from the compounds Ia.fl to iol to Ia.f'-
1'~21 anly in that Z is S:

;a
0050/50080
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125
R3
X
II ~ \ Ra
la.f~~ ec ao
HI
S~N~ O
R O'
R9x RB
M°reover, preference is given to the compounds Ib.fZl to aol to
Ib. f21 to 3021 which differ from the compounds Ia. fl to lol to Ia.fl
to 1021 only in that the N substituents are inverted and Z is S:
NCR F
~N~ ~~ ~ \ a Ib.f2~toso
C R
O
O
Ra~Ra
25
35
4S

0050/50080
CA 02377143 2001-12-19
12 fi
To prepare the compounds of the formula Ia according to the
invention where Z = O, it is possible, for example, to react the
N-(2-hydroxyethyl)-N-amino-N'-acylureas known from WO 94/10173
and the later German Patent Application 198 29 745.9 according to
scheme 1 with formaldehyde, for example an aqueous formaldehyde
solution, to give the N-methylimino-N-(2-hydroxyethyl)-
N'-acylureas, which are then cyclized in the presence of
catalytic amounts of acid or a surface-active metal oxide to give
the compound Ia according to the invention. For further details
about the cyclization, reference is made to WO 94/10173 and the
later patent application. Here and below, the variables used in
the formulae are as defined above unless specifically stated
otherwise.
Scheme 1
0 0
a HcHO _ ~~, , a
~N~ ~N~ ~N NH
HO NH2 H /N
0
~ A
H+ N' -NH (Ia,R=H)
~N
e.g. Si02) ~ ~H
Compounds of the formula Ia where R = hydrogen can be prepared by
reacting 1H,2H-perhydrodiazines of the formula IIa (R = H) with
an isocyanate (X = O) or an isothiocyanate (X = S) of the formula
III. In the same manner, it is also possible to obtain compounds
Ia where R ~ H if the corresponding nitrogen-substituted compounds
IIa (R ~ H) are used as starting materials.
Scheme 2 X
i1
~N'C~NHGl
+ X=C=N-D Z N
Z~NR ~ ~ R
II a Ill I a
Analogously, i~ is also possible to react N-substituted
perhydrodiazines :CIb with an isocyanate or isothiocyanate II~~ Y~>
give the end _~,-oclucts :CIb according to the following scheme:

0500/50080
CA 02377143 2001-12-19
127
Scheme 2a X
,H Z~N'C~H'C
Z N .1. X=C=N-D "' N
N\ (RA~
~R
(RA)m R
II b III 1 b
According to a further process, shown in scheme 3, substituted
triazolinediones (X = O) or -thiones (X = S) of the formula IV
can be ring-opened with an alkoxide or thiolate to give the
substituted ureas Ibll) (R = C(X)YR1~ where X = O or S and Y = O
or S).
Scheme 3 X
~.J Z~N'C~NH O
Z N~ + -YR~o --~- N
N N-D (RA)~ ~C(X)YR,a
(RA)m
IV V I b
In a corresponding manner, it is possible to prepare the
substituted ureas Ibl2> (R = C(O)NR11R12) according to the
invention by the process shown in scheme 3a, starting from
substituted triazolinediones (X = O) or -thiones (X = S) of the
formula IV by reaction with a basic amine VI.
X
Scheme 3a
Z~N~ + HNR~~R~2 --= Z~N'C~NHGl
N~'~N-D
(RA~N~C(O)NR~~ R,z
(RA)m
IV VI I b
According to the process shown in scheme 4, substituted ureas of
the formula Ia' where R = H can be reacted with a chlorocarbonyl
isocyanate VIIa or chlorosulfonyl isocyanate VIIb or with a
substituted carbonyl isocyanate VIIIa or sulfonyl isocyanate
VII Ib to give the subst ituted ureas Ian 3 ~ (where R = C ( O ) NHVC1 ) or
Ia141 (where R = C(O)NH~~~rRl2~).
NII~O 1 ~~)

~~50~5~~$0 CA 02377143 2001-12-19
1~$
Scheme 4
X
X=C=NVCI (RA)m II
C
~NH
~N~
+ Vlla V=CO -- ~ I
Z~N~
~NHVCI
C
X VII b V = SOz O
(RA) m I I G~
.C. 1 a(a)
H
N
~N
ZvN~
H
X
X=C=NWR~2' (RA)m ICI /O
'
I a ~N~ ~NH
(R = H) + VIII a W = COZ ~ Z N NHWR~2'
~
'
C
VIII b W = S02 Q
VIII c W = S03 1 a(4)
In a corresponding manner, it is possible to prepare the
substituted ureas Ia (R ~ H) according to the process shown in
scheme 5, starting with ureas of the formula Ia' (R = H), by
reaction with an acid derivative IX in which A is a leaving
group.
Scheme 5
A II
(R )m ~C. -D (RA)m N~C~NH O
N N H -E- R-A -
~N
Z~N~H R
la'(R= H) IX la
Furthermore, according to scheme 6, it is possible to hydrolyze
the ureas of the formula Ib which are substituted at the second
ring nitrogen and in which R is a radical which can easily be
removed, such as C(X)YR1~, CO2H or CHO, to give the ureas Ib'
where R = H. From these, it is then possible to prepare the
substituted ureas where R = C(X)YR1~, CHO, CN, C(X)NRllRlz, C(O)Rz,
P(O)(OR1)R1, P(O)(OR1)z, S(O)RB, S(O)ZR1 or S(O)zNHR1 by reaction
with an acid derivative R-A in which R is as defined above and A
is a nucleophilically displaceable leaving group.

0050/50080
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Scheme 6
X X
Z~N'C~NHGl H2O Z~N'C~NHGI
~, ~ -ROH ~N~H
(RA~N~R (RA)m
Ib Ib' (R=H)
X
X
1
Z~N'~~NHQ -I- R-A -----~- Z~N'~~NHCl
N
~~ ~ ~R
~N~H (Rn~
(R )
I b' (R = H) iX I b
The schemes 4 to 6 above also apply in an analogous manner to the
corresponding isomer in which Z is in the respective other
position, i.e. according to scheme 4, it is possible to prepare
the compounds Ib~3~ and Ib~4~ from Ib' (R = H), and according to
scheme 5, it is possible to prepare the compounds Ib from Ib'.
Correspondingly, according to scheme 6, the radical R in the
compounds Ia can be converted via hydrolysis to give the
compounds Ib' (R = H) followed by reaction with R-A. Hereinbelow,
the reaction conditions and the way in which the processes are
carried out are described for the preparation of the ureas Ia and
Ib substituted at the second ring nitrogen; however, the
instructions can be applied to the preparation of all compounds
of the formulae Ia and Ib in which R is hydrogen.
The solvents which are selected for these reactions are -
depending on the temperature range - hydrocarbons, such as
pentane, hexane, heptane, cyclohexane, aromatic compounds, for
example benzene, toluene, xylene, heteroaromatic compounds, for
exarnle pyridine, a,(3,y-picoline and quinoline, chlorinated
hydrocarbons, for example methylene chloride, 1,1-dichloroethane,
1,2-dichloroe-thane, 1,1,2,2-tetrachloroethane,
1,1-dichloroethylene, chlorobenzene, 1,2-, 1,3-,
1,4-dichlorobenzene, 1-chloronaphthalene and
1,2,x-trichlurobenzene, ethers, such as 1,4-ctioxane, anisole,
glycol ethers, such as dimethyl glycol ether, diethyl glycol
ether, diethylene glycol dimethyl ether, esters, such as ethyl
acetate, pr~:~c~y? acetate, methyl isobutvrate, isobutyl acetate,
cnrboxamide~~, such as DMF, N-methylpyrrolidone, ni_r_rated
hydrocarbons, s~_lch as nitromethane, nitroetWne, nitropropaae and

~pr~~~ ,r~0~8~ CA 02377143 2001-12-19
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nitrobenzene, ureas, such as tetraethylurea, tetrabutylurea,
dimethylethyleneurea, dimethylpropyleneurea, sulfoxides, such as
dimethyl sulfoxide, sulfones, such as dimethyl sulfone, diethyl
sulfone, tetramethylene sulfone, nitrites, such as acetonitrile,
propionitrile, butyronitrile or isobutyronitrile; water or else
mixtures of individual solvents.
The molar ratios at which the starting materials of the
individual reaction schemes are reacted with one another are
generally 0.9 to 1.4, preferably 0.95 to 1.2, particularly
preferably 0.98 to 1.15 for the ratio of aldehyde to
N-amino-N'-phenylurea; or for the ratio of perhydrodiazine IIa or
N-substituted perhydrodiazine IIb to isocyanate or isothiocyanate
III, of triazolinedione IV to the nucleophiles V and VI, of
substituted urea Ia' (where R = H) to the isocyanates VIIa or b
or VIIIa, VIIIb or VIIIc or the acid radical IX. The reaction of
the substituted urea Ib (where R x H) and water and of urea Ib' (R
- H) and the acid radical IX can likewise be carried out under
the molar ratios mentioned.
The hydrolysis of the substituted urea Ib in scheme 6 is
advantageously also carried out in an excess of water, for
example in aqueous solution.
The concentrations of the starting materials in the solvent are
generally from 0.1 to 5 mol/1, preferably from 0.2 to 2 mol/1.
The reaction sequence illustrated in scheme 1 is described in
more detail below.
The reaction of the N-amino-N'-arylureas according to scheme d
with formaldehyde or paraformaldehyde is advantageously carried
out in the presence of a solvent at 0 to 150°C, preferably 10 to
100°C, particularly preferably 20 to 60°C. Aqueous formaldehyde,
preferably as an about 37~ strength solution, is advantageously
added at 10 to 25°C and over 2 to 20 min to a mixture of the
N-amino-N'-arylurea in one of the abovementioned solvents, and
the mixture is then stirred for another 0.5 to 12 hours,
preferably 1 to 3 hours, at 20 to 60°C for the reaction to go to
completion. However, it is also possible to add the
N-amino-N'-arylurea to a mixture of formaldehyde in one of the
abovementioned solvents and then to complete the reaction as
above. Instead of aqueous formaldehyde, it is also possible to
use paraformaldehyde. It is generally not necessary to remove the
water of reaction; hovaever, the water of reaction can also be
removed during the reaction via a water separator. The reaction
with formaldehyde according to step 1 in scheme 1 is preferably

CA 02377143 2001-12-19
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carried out on exclusion of acidic catalysts, i.e. in neutral to
slightly alkaline medium. If appropriate, acidic impurities are
neutralized by addition of basic compounds, for example alkali
metal or alkaline earth.metal hydroxides or bicarbonates or
carbonates. If appropriate, it is also possible to add organic
bases or to carry out the reaction using a basic solvent
component, such as pyridine. The reaction can be carried out
under atmospheric pressure or superatmospheric pressure,
continuously or batchwise.
The cyclization of the N-methyleneimino-N'-arylureas to give the
4-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazines is
carried out with addition of, in general, 1 to 100 by weight of
an acid, based on the urea, advantageously in the presence of one
of the abovementioned solvents, at from 0 to 150°C, preferably 10
to 120°C, particularly preferably 20 to 80°C.
The acid used can be an aromatic sulfonic acid, for example
benzenesulfonic acid, p-chlorobenzene- or p-toluenesulfonic acid,
an aliphatic sulfonic acid, such as methanesulfonic acid,
trifluoromethanesulfonic acid, ethanesulfonic acid and
n-propylsulfonic acid, a sulfaminic acid, such as
methylsulfaminic acid, ethylsulfaminic acid or
isopropylsulfaminic acid, an aliphatic carboxylic acid, such as
acetic acid, trifluoroacetic acid, propionic acid, butyric acid
or isobutyric acid, and inorganic acid, such as hydrochloric
acid, sulfuric acid, nitric acid or boric acid.
The N-methyleneimino-N'-arylurea is advantageously added at 10 to
25°C and over 2 to 20 min to the organic acid, preferably acetic
acid, as reaction medium, and stirring is continued at 20 to 80°C
for 0.5 to 12 hours, preferably 1 to 3 hours. However, the acid
can also be added directly to the reaction solution of the
N-methyleneimino-N'-arylurea intermediate formed from
N-amino-N'-arylurea and formaldehyde, and the intermediate can be
cyclized without isolation, if appropriate after some of the
solvent has been distilled off, to give the
4-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazine.
The concentration of the starting materials in the solL~ent is
generally from 0.1 to 5 mo1/1, preferably from 0.2 to 2 mol/1.
Instead of an acid, it i~ also possible to use, as cat alys-t, a
neutral or acidic surface-active metal oxide, for example
aluminum oxide, iron o:ti.is, boron oxide, silicon dioxide;

0050/50080 CA 02377143 2001-12-19
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titanium dioxide, arsenic oxide, antimony oxide, chromium oxide
or manganese oxide.
The reaction can be carried out under atmospheric pressure or
superatmospheric pressure, continuously or batchwise.
If R represents hydrogen, the compounds of the formulae Ia and Ib
can be cyclized analogously to known processes to give bicyclic
triazolinediones (scheme la).
Scheme la
X O
"~~. w
~N NH ~N N - Q
w/N~H
I a' (R = H) IV
The cyclization of the 4-(arylcarbamoyl)tetrahydro-4H-
1,3,4-oxa(or thia)diazines according to scheme la is carrried out
using phosgene, thiophosgene or a phosgene substitute, for
example diphosgene (C1C(=O)OCC13), advantageously in the presence
of one of the abovementioned anhydrous solvents, at from -10 to
120~C, preferably from 0 to 80~C, particularly preferably from 10
to 60~C.
The phosgene is advantageously introduced at 10 to 60~C and with
stirring into a mixture of a
4-(phenylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazine and an
amount of from 0.5 to 5% by weight, based on the starting
material, of activated carbon as catalyst in one of the
abovementioned anhydrous solvents, over a period of 0.5 to 20
hours, preferably 1 to 12 hours.
The reaction can additionally be promoted by a basic amide
catalyst, for example DMF, which is usually employed in an amount
of from 0.3 to loo by weight, based on the starting material. The
basic catalyst used can also be an organic base, such as
triethylamine, tri-n-propylamine, N,.N -dimethyl.anil.ine or
N,N-dimethylcyclohexylamine. Also preferred is the use of
pyridine, if appropriate directly as solvent.
In place of phosgene, it is also possible to use diphosgene. The
diphosgene is advantageously added vap.th stirring, at from 0 to
-5~r and over a period of ? to 20 min, to the mixture of the
starting material and one of t he abovementioned solvents, if

0050/50080
CA 02377143 2001-12-19
13~
appropriate with addition of activated carbon, DMF or the organic
base, and the mixture is allowed to warm to 10°C over a period of
1 hour and then stirred at 10 to 60°C for another 1 to 12 hours.
The molar amount of phosgene or diphosgene is 0.98 to 5,
preferably 1 to 3, particularly preferably 1 to 1.3, per mol of
starting material.
The concentration of the starting materials in the solvent is
generally from 0.1 to 5 mol/1, preferably from 0.2 to 2 mol/1.
The reaction can be carried out under atmospheric pressure or
superatmospheric pressure, continuously or batchwise.
The multistep reaction according to schemes 1 and la can also be
carried out advantageously as a one-pot process, where, in the
first synthesis step, the water of reaction is removed during the
reaction of the N-amino-N'-phenylureas with formaldehyde, the
N-methyleneimino-N'-phenylureas formed are cyclized with addition
of a neutral or acidic catalyst to give the
4-(phenylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazines, and
these are then, if appropriate,. cyclized using phosgene or
diphosgene, if appropriate with addition of activated carbon or
an amide catalyst or in the presence of a base, to give the end
products Ia'. If appropriate, any acidic catalysts present are
removed prior to the phosgene cyclization by phase separation or
distillation, followed by ring closure to give the
triazolinediones IV.
For work-up, the intermediates are taken up in a water-immiscible
solvent, acidic impurities are extracted using dilute alkali or
water, the mixture is dried and the solvent is removed under
reduced pressure.
The reactions according to schemes 2 and 2a are illustrated in
more detail below.
In the reactions according to the invention, an isocyanate or
isothiocyanate III is advantageously added at 10 to 25°C and over
a period of 5 to 30 min to a mixture of the perhydrodiazine IIa
or IIb in one of the abovementioned solvents, and the mixture is
then stirred at 20 to 80°C for another 0.5 to 24 hours, preferably
1 to 10 hours, for the reaction to go to completion. However, in
the case of the reaction of the DI-su.bst.ituted perhydrodiazines
R # H), it. is also possible to initially charge the isocyanate or
isothiocyanate III in one of the abovementioned solvents, to add

0050/50080
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134
the N-substituted perhydrodiazine and then to complete the.
reaction as above.
In the ring opening of the triazolinedione IV with the
nucleophiles V and VI according to schemes 3 and 3a, the
nucleophile is advantageously added at 10 to 30°C and over a
period of 5 to 30 min to a mixture of the triazolinedione IV in
one of the abovementioned solvents, and the mixture is then
stirred at 20 to 60°C for 0.5 to 24 hours, preferably for 1 to 10
hours, for the reaction to go to completion. However, it is also
possible to add the triazolinedione IV to a mixture of the
nucleophile in one of the abovementioned solvents and then to
complete the reaction as above.
The alcohols or thiols of the formula V are advantageously
employed in the form of their alkali metal or alkaline metal
salts, i.e. their lithium, sodium, potassium, magnesium or
calcium salts. However, the reaction can also be carried out in
the presence of an organic base, for example triethylamine,
tri-n-propylamine, N-ethyldiisopropylamine, pyridine, a-, (3-,
~y-picoline, 2,4-, 2,6-lutidine, N-methylpyrrolidine,
triethylenediamine, dimethylaniline, N,N-dimethylcyclohexylamine,
quinoline or acridine. Salt formation can furthermore be carried
out using an alkali metal or alkaline earth metal hydride or
hydroxide. Using one of the abovementioned bases, the alcohols or
thiols are advantageously converted in an inert solvent into
their corresponding salts, followed by the reaction with the
triazolinedione. Depending on the reactivity of the alcohols or
thiols used, the water formed during the salt formation can
remain in the reaction medium or be removed azeotropically with a
solvent. It is also possible to carry out the salt formation from
the outset in aqueous phase and then to remove the water.
Furthermore, the salt formation can also be carried out using an
alkali metal or alkaline earth metal alkoxide, preferably sodium
methoxide or ethoxide, and to remove excess alcohol prior to the
reaction with the triazolinedione, or to carry out the reaction
directly using the same alcohol as solvent.
During the addition of the isocyanates VIIa or VIIb or VIIIa,
VIIIb or VIIIc according to scheme 4 or the acid derivative IX
according to scheme 5 to the substituted urea Ia' where R = H,
the isocyanates VIIa or VIIb or VIIIa, VIIIb or VIIIc or the acid
derivative IX - in 'the latter case preferably in the presence of
a base - are advantageously added to a mixture of the substituted
urea Ia' or Lb' where R = H in one of t'ne abovementioned
solvents, at 10 to 30°C, and the mixture is then stirred For

IF
0050/50080
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135
another 0.5 to 24 hours, preferably 1 to 10 hours, at 20 to 120~C
for the reaction to go to completion.
However, it is also possible to add the substituted urea Ia or Ib
where R = H to a mixture of the isocyanates VIIa or VIIb or
VIIIa, VIIIb or VIIIc or the acid derivative IX - in the latter
case preferably in the presence of a base - and then to complete
the reaction as above. When using the acid derivatives IX
according to scheme 5 or 6, the substituted urea Ia' is
preferably initially charged together with a base and the acid
derivative IX is then added as described above, or the
substituted urea Ia' or Ib' where R = H is added together with a
base to the acid derivative IX.
Suitable for use as base are the bases mentioned in the
illustrations to schemes 3 and 3a, preferably organic bases, such
as triethylamine or pyridine. However, it is also possible to
convert the urea Ia' or Ib' where R = H beforehand at the NH
group into its salt, using an alkali metal hydride or alkaline
earth metal hydride, preferably sodium hydride or potassium
hydride. If the reaction is carried out in a two-phase system,
aqueous solutions of alkali metal or alkaline earth metal
bicarbonates, carbonates or hydroxides, preferably sodium
hydroxide, are employed.
The base is advantageously employed in a molar ratio of from 0.9
to 1.4, preferably from 0.95 to 1.2, particularly preferably from
p,g8 to 1.15, for the ratio of substituted urea Ia' (where R = H)
to base.
The reaction of Ia' or Ib' with the acid derivatives IX according
to scheme 5 or 6 can also be carried out in a two-phase system in
the presence of a phase-transfer catalyst. Suitable
phase-transfer catalysts are quaternary ammonium or phosphonium
salts. Suitable compounds which may be mentioned are:
tetraalkyl-(C1-C1$)-ammonium chlorides, bromides or fluorides,
N-benzyltrialkyl-( C1-C1a)-ammonium chlorides, bromides or
fluorides, tetraalkyl-(C1-C18)-phosphonium chlorides or bromides,
tetraphenylphosphonium chloride or bromide,
(phenyl)o(a1kt11-(CL-Cls))P-phosphonium chlorides or bromides,
where o = 1 to 3, p = 3 to 1 and o + p = 4. Particular preference
is given to tetraethylammonium chloride and
N-benzyltriethylammonium chloride. The amount of phase-transcer
catalyst is generally up to 20°s by weight, preferably between 1
and 15o by weight and particularly preferably between 2 and 8~ ~%y
weight, based on the acid derivative IX.

0050/50080
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In the acid derivate IX, A is a leaving group, such as halogen,
for example fluorine, chlorine or bromine, preferably chlorine,
in the case of C(0)R2, it is an oxy-C1-C6-alkanoyl,
oxy-C3-C6-alkenoyl or oxy-C3-C6-alkynoyl radical, and in the case
of formyl, it is an oxy-C1-C6-alkanoyl radical.
If the starting material available is a substituted urea Ia or Ib
in which R is a radical that can easily be cleaved off, such as
C(O)OR1~, C(S)OR1~, C(S)SR1~, C(O)SR1~, COZH or CHO (urea Ib -
scheme 6), this radical R can be cleaved off according to scheme
6 by hydrolysis with water, advantageously in the presence of a
base, at from 10 to 100°C, advantageously from 20 to 80°C. Thus,
the substituted urea Ib(1) is initially charged in one of the
abovementioned solvents, for example water, the base is then
added and the reaction is completed, giving the urea Ib where R =
H.
Here, the base is advantageously employed in a molar ratio of
from 0.9 to 1.4, preferably from 0.95 to 1.2, particularly
preferably from 0.98 to 1.15, for the ratio of substituted urea
Ib to base. The bases used can be those mentioned above,
preferably alkali metal or alkaline earth metal hydroxide,
particularly preferably sodium hydroxide.
Finally, according to scheme 6, the resulting substituted urea Ib
(or Ia') where R = H can be substituted at the free amino group
by acid derivatives IX to give the novel substituted ureas Ib'
where R ~ H. To this end, the acid derivative IX is advantageously
added to a mixture of the substituted urea Ib where R = H in one
of the abovementioned solvents, at from 10 to 30°C, advantageously
in the presence of a base, and the mixture is then stirred at 20
to 120°C for another 0.5 to 24 hours, preferably 1 to 10 hours,
for the reaction to go to completion.
The reaction conditions that apply to this reaction step are the
same as those described for the reaction of the acid derivatives
IX with the inversely substituted ureas Ia' (according to scheme
5).
In principle, the substituted ureas -Ia and Ib can be prepared
according to the synthesis process according to the invention
mentioned above. However, for economical or technical .reasons, it
may be more advantageous to prepare some compounds :Ca and Ib from
similar substituted u.reas Ia and Ib which differ in the meaning
of one radical.

CA 02377143 2001-12-19
137
Work-up of the reaction mixtures is generally carried out by
methods known per se, for example by diluting the reaction
solution with water, followed by isolation of the product by
filtration, crystallization or solvent extraction, or by removing
the solvent, partitioning the residue in a mixture of water and a
suitable organic solvent and work-up of the organic phase to
afford the product.
The oxazine derivatives of the formula IIa used as starting
materials according to scheme 2 are novel and form part of the
subject matter of a parallel application. They are prepared, for
example, by initially reacting a substituted hydrazine of the
formula X
~RA)m
_ I H (x)
HZ NH2
in which Z is O or S and RA and m are as defined above in a first
step with an acid derivative R-A (formula IX), in which R is as
defined above and A is a nucleophilically displaceable leaving
group, or an isocyanate of the formula VIIa,b or VIIIa-c, and
cyclizing the resulting hydrazide in a second step with
formaldehyde in the presence of an acid to give the substituted
perhydrodiazines of the formula Ia where Z = O or S, which are,
if appropriate, in the case that z = S, oxidized in a further
reaction step to give the sulfoxides Z = SO or sulfones Z = 502,
or the radicals R are derivatized.
Examples of suitable nucleophilically displaceable leaving groups
are halogen, preferably chlorine or bromine, C1-C6-alkoxy, such as
methoxy, ethoxy, n-propoxy, n-butoxy, C1-C4-haloalkoxy, such as
trichloromethoxy, trifluoromethoxy, pentafluoroethoxy, N-bonded
heterocyclyl, such as imidazolyl, C1-C6-alkylcarbonyloxy (or
C1-C6-alkanoate), such as acetate, propionate, n-butyrate,
isobutyrate, pivalate and caproate, C1-C6-haloalkylcarbonyloxy,
such as mono-, di- and trichloroacetate, C1-C6-alkylsulfonyloxy,
such as methylsulfonyloxy, C1-C5-haloalkylsulfonyloxy, such as
trifluoromethylsulfonyloxy, phenylsulfonyloxy, where the phenyl
radical may, if appropriate, be mono- or disubstituted by halogen
or C1-C6-alkyl, such as phenylsulfonyloxy, p-toluenesulfonyloxy
and p-C1-phenylsulfony.Loxy, N-bonded nitrogen-C5-C6-heterocyclyl,
such as N-imidazolyl.

0050/50080
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Preferred leaving groups are halogen, in particular chlorine or
bromine, and furthermore acetate or trifluoroacetate.
The cyclization of the 2nd preparation step can be carried out
using both formaldehyde or a compound which releases formaldehyde
under acidic conditions, such as paraformaldehyde or
1,3,5-trioxane, in the presence of an acid.
However, it is also possible to react the hydrazides obtained in
the 1St reaction step with formaldehyde to give the Schiff base
which is then cyclized by addition of an acid.
The reaction described in the scheme below is an example of the
preparation of the compounds IIa where, starting from
2-hydrazinoethanol and methyl chloroformate as acid derivative,
firstly the N-amino-N-methoxycarbonyl-2-hydrazinoethanol is
prepared, which is cyclized in a subsequent reaction with
formaldehyde to give
tetrahydro-4-methoxycarbonyl-4H-1-oxa-3,4-diazine.
,COZCH3
/'~ C02CHy N
N I ~ - HCI ' [ N/ + HCHO H--'-~ I
O~NH + CI~COCH3 IOH NH O.~N~
Z H
Preferred embodiments of the process are mentioned below:
The first reaction step is explained in more detail below: The
reaction of the hydrazinoethanols/-thiols X with the acid
derivatives R-A is advantageously carried out in the presence of
a solvent at from -30 to 100°C, preferably from -10 to 80°C,
particularly preferably from 0 to 60°C.
The solvents used for these reactions are - depending on the
temperature range - hydrocarbons, such as pentane, hexane,
cyclopentane, cyclohexane, toluene, xylene, chlorinated
hydrocarbons, such as methylene chloride, chloroform,
1,2-dichloroethane, 1,1,2,2-t etrachloroethane, chlorobenzene,
1,2-, 1,3- or 1,4-dichlorobenzene, ethers, such as 1,4-dioxane,
anisole, glycol ethers, such as dimethyl glycol ether, diethyl
g!vcol ether, diethylene glycol dimethyl ether, esters, such as

005050080 CA 02377143 2001-12-19
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ethyl acetate, propyl acetate, methyl isobutyrate, isobutyl
acetate, carboxamides, such as DMF, N-methylpyrrolidone, nitrated
hydrocarbons, such as nitrobenzene, ureas, such as
tetraethylurea, tetrabutylurea, dimethylethyleneurea,
dimethylpropyleneurea, sulfoxides, such as dimethyl sulfoxide,
sulfones, such as dimethyl sulfone, diethyl sulfone,
tetramethylene sulfone, nitriles, such as acetonitrile,
propionitrile, butyronitrile or isobutyronitrile; water or else
mixtures of individual solvents.
The molar ratios in which the starting materials X and IX are
reacted with one another are generally from 0.9 to 1.2,
preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, for
the ratio of acid derivative of the formula IX to
hydrazinoethanol/-thiol X.
The first reaction step is advantageously carried out under
neutral conditions. If an acidic reaction product is formed in
the reaction, for example hydrogen halide if A in the formula IX
is halogen, this is removed by addition of basic compounds, for
example alkali metal or alkaline earth metal hydroxides or
bicarbonates or carbonates. However, the reaction can also be
carried out in the presence of an organic base, for example
triethylamine, tri-n-propylamine, N-ethyldiisopropylamine,
pyridine, a-, [3-, y-picoline, 2,4-, 2,6-lutidine,
N-methylpyrrolidine, dimethylaniline,
N,N-dimethylcyclohexylamine, quinoline or acridine.
Finally, the reaction can also be carried out in an aqueous
two-phase system, preferably in the presence of phase-transfer
catalysts, such as quaternary ammonium or phosphonium salts. The
reaction conditions mentioned above and in EP-A 556737, as well
as the abovementioned phase-transfer catalysts, are suitable for
the two-phase reaction.
Advantageously, the acid derivative IX is added, at 0 to 60~C and
over a period of 0.25 to 2 hours, to a mixture of the
hydrazinoethanol/-thiol X and the base in one of the
abovementioned solvents, and stirring at 0 to 60~C is continued
for 0.5 to 16 hours, preferably 2 to 8 hours, for the reaction to
go to completion.
If an aqueous two-phase system is used, the starting materials X
and IX can be added with stirring, in any order, to a mixture of
the phase-transfer catalyst in the tG~lo phases, and the .reaction

CA 02377143 2001-12-19
140
can then be completed in the temperature range mentioned by
adding base.
The reaction can be carried out under atmospheric pressure or
under superatmospheric pressure, continuously or batchwise.
For work-up, any precipitated salts are separated off, or their
removal is completed by addition of nonpolar solvents, and the
hydrazides are thus accomulated in the filtrate.
The second reaction step is explained below: the hydrazides are
subsequently reacted, advantageously under acidic conditions,
with a formaldehyde solution or paraformaldehyde in one of the
abovementioned solvents.
For the subsequent step, advantageously 0.9 to 1.2, preferably
0.95 to 1.1, particularly preferably 0.98 to 1.04, molar
equivalents of formaldehyde or paraformaldehyde are employed per
mole of hydrazide derivative. The concentration of the starting
materials in the solvent is 0.1 to 5 mol/1, preferably 0.2 to
2 mol/1.
The acid used can be an aromatic sulfonic acid, for example
benzenesulfonic acid, p-chlorobenzene- or p-toluenesulfonic acid,
an aliphatic sulfonic acid, such as methanesulfonic acid,
trifluoromethanesulfonic acid, ethanesulfonic acid and
n-propylsulfonic acid, a sulfaminic acid, such as
methylsulfaminic acid, ethylsulfaminic acid or
isopropylsulfaminic acid, an aliphatic carboxylic acid, such as
acetic acid, trifluoroacetic acid, propionic acid, butyric acid
or isobutyric acid, or an inorganic acid, such as hydrochloric
acid, sulfuric acid, nitric acid or boric acid. Advantageously,
it is also possible to use an acid such as acetic acid or
propionic acid directly as reaction medium. The acidic catalyst
is advantageously employed in an amount of from 1 to 20 mol%,
preferably 3 to 15 mol%, particularly preferably 5 to 10 mol%, of
acid per mole of hydrazide.
Preferably, a formaldehyde solution or paraformaldehyde is added
over a period of 2 to 60 min to a mixture of hydrazide and the
acidic catalyst in one of the abovementioned solvents at 0 to
100°C, advantageously 10 to 80°C, particularly preferably 2U to
50°C, and stirring is continued at 40 to 50°C: for 10 to 50
hours,
preferably 15 to 30 hours, to bring the reaction to completion.

~~5~~~~~$~ CA 02377143 2001-12-19
1~~
If an aqueous formaldehyde solution is used, the water is
advantageously removed, for example using a water separator.
However, it is also possible to add the acidic catalyst to a
mixture of hydrazide and paraformaldehyde in one of the
abovementioned solvents and then to complete the reaction as
described.
The reaction can be carried out under atmospheric pressure or
under superatmospheric pressure, continuously or batchwise.
The oxidation of the perhydrodiazines IIa where Z = S to the
sulfoxides (Z = S02), which follows, if appropriate, is preferably
carried out using hydrogen peroxide, the sulfoxides being
obtained with approximately equivalent amounts of oxidizing
agent, and the sulfones being obtained with about double the
molar quantities.
The oxidation with hydrogen peroxide can be catalyzed by suitable
metal compounds, for example transition metal oxides, such as
vanadium pentoxide, sodium tungstate, potassium dichromate, iron
oxide tungstate, sodium tungstate/molybdic acid, osmic acid,
titanium trichloride, selenium dioxide, phenylselenic acid,
oxovanadinyl-2,4-pentanedionate. The catalysts are generally
employed in an amount of from 0.5 to 10~, but it is also possible
to employ stoichiometric amounts because the inorganic catalysts
can easily be filtered off and recovered.
Solvents which are suitable for the oxidation with hydrogen
peroxide are, for example water, acetonitrile, alcohols, such as
methanol, ethanol, isopropanol, tert-butanol, chlorinated
hydrocarbons, such as methylene chloride,
1,1,2,2-tetrachloroethane, or ketones such as acetone or methyl
ethyl ketone.
In addition to hydrogen peroxide, it is also possible to use, as
oxidizing agents, peracids, such as perbenzoic acid,
monoperphthalic acid or 3-chloroperbenzoic acid. The reaction
with peracids is expediently carried out in chlorinated
hydrocarbons, such as methylene chloride or 1,2-dichloroethane.
Also very suitable for oxidizing the thiols to sulfo:Yi.des or
sulfones are chlorine and bromine. This oxidation is t~xpediewt:~y
carried out in polar solvents, such as water, acetoc:itrile,
dioxane, or in. two-phase systems, such as aqueous potassium
bicarbonate solution/dichloromethane, and also acetic acid. ~t Ls
furthermore ~ossihle to employ as sources of activ? halogen

tk
~05~I~50~$~ CA 02377143 2001-12-19
142
tert-butyl hypochlorite, hypochlorous and hypobromous acid, their
salts, and also N-halo compounds, such as N-bromo- and
N-chlorosuccinimide, or else sulfuryl chloride.
Also suitable for the oxidation is photosensitized oxygen
transfer, in which case the photosensitizers used are usually
organic dyes, for example porphyrines, such as
tetraphenylporphyrine, chlorophyll, protoporphyrine, xanthene
dyes, such as Rose Bengal or phenothiazine dyes, such as
Methylene Blue.
Suitable inert solvents are hydrocarbons, such as pentane,
hexane, heptane, cyclohexane, chlorinated hydrocarbons, such as
methylene chloride, 1,2-dichloroethane,
1,1,2,2-tetrachloroethane, alcohols, such as methanol, ethanol,
n-propanol or isopropanol, ketones, such as acetone, methyl ethyl
ketone, polar aprotic solvents, such as acetonitrile,
propionitrile or aromatic hydrocarbons, such as benzene, toluene,
chlorobenzene or xylene. In place of oxygen, it is also possible
to use ozone in the abovementioned solvents, plus ether,
1,4-dioxane or THF.
Besides photosensitization, catalysts are also suitable for the
oxidation with oxygen, for example oxides and sulfides of nickel,
copper, aluminum, tungsten, chromium, vanadium, ruthenium,
titanium, manganese, molybdenum, magnesium and iron.
Either the sulfoxides (IIa where Z = SO) or their sulfones (IIa
where Z = S02) are obtained, depending on the stoichiometry of the
oxidizing agents used. The molar ratios in which the starting
materials are reacted with one another are generally 0.9 to 1.8,
preferably 1.05 to 1.3, for the ratio of tetrahydrothiadiazine to
oxidizing agent in the case of the oxidation to the sulfoxide and
generally 1.9 to 3.5, preferably 2.05 to 2.9, in the case of
oxidation to the sulfone.
The concentration of the starting materials in the solvent is
generally 0.1 to 5 mol/1, preferably 0.2 to 2 moll.
It is advantageous to initially charge the 1-thiadiazine of the
formula IIa where Z = S or the sulfoxide, if appropriate together
with one of the abo~,rementioned catalysts, in one of the
abovementioned soi~rents, and then to add the oxidizing agent over
a period of 0.25 to 20 hours with stirring. The addition and t he
reaction temperature depends on the optimum efficiency of the
oxidizing agent .in question and on avoiding side reactions. If
photosensitized oxygen is used, the reaction is generally carried

CA 02377143 2001-12-19
143
out at from -20 to 80°C; however, if metal catalysis is employed,
the reaction is generally carried out at from 50 to 140°C, and if
ozone is used, the reaction is generally carried out at from -78
to 60°C. Owing to the limited solubility of the oxygen
derivatives, they are preferably introduced continuously into the
reaction mixture over a relatively long period of time (up to
20 h) until the oxidation has been completed at the sulfoxide or
sulfone stage. Liquid or easily soluble oxidizing agents, such as
hydrogen peroxide, hypochlorous or hypobromous acid, tert-butyl
hypochlorite, chlorine or bromine, furthermore N-chloro- or
N-bromosuccinimide, can be added to the reaction mixture of the
thiadiazine or thiadiazine sulfoxide over shorter periods of
time, such as 0.25 to 6 h, depending on the exothermic character
of the reaction, and the reaction is ended after a further 1 to
60 h. Preference is furthermore given to adding the liquid or
dissolved oxidizing agent gradually. In the case of hydrogen
peroxide, the reaction is generally carried out at from O to 90°C,
with tert-butyl hypochlorite, the reaction is generally carried
out at from -78 to 30°C, and with N-halo compounds generally at
from 0 to 30°C. In the case of chlorine or bromine, a reaction
temperature of from 0 to 40°C is recommended.
The oxidations can be carried out under atmospheric pressure or
under superatmospheric pressure, continuously or batchwise.
The multistep reaction can advantageously also be carried out as
a one-pot process, where the thiadiazines IIa (Z = S) are
converted directly, without isolation and purification, into the
sulfoxides IIa (Z = So) or the sulfones IIa (Z = S02).
Accordingly, the reaction product Ia is, if appropriate, allowed
to cool to from 90 to 20°C, a solvent, for example methylene
chloride and/or water, is added, if appropriate, and the
oxidizing agent is then added at the rate of its consumption.
Particularly preferred oxidizing agents are hydrogen peroxide and
sodium hypochlorite.
For work-up of the oxidation mixture, the end products IIa are
generally taken up in a cater-immiscible solvent, acidic
impurities and/or oxidizing agents are extracted using dilute
alkali or water, the mixture is dried and the solvent is removed
under reduced pressure.

~~5~~5~~$~ CA 02377143 2001-12-19
144
I. Preparation of the starting compounds
Methyl tetrahydro-N-(2,4-dichloro-5-methoxyimino-methylphenyl)-
4H-1,3,4-oxadiazine-3-thiocarboxamide-4-carboxylate
a) Methyl N-amino-N-2-hydroxyethylcarbamate
At from 0 to 5~C, 248.4 g (2.628 mol) of methyl chloroformate
were added with stirring, in the course of 30 min, to a mixture
of 200 g (2.628 mol) of 2-hydrazinoethanol and 266 g (2.628 mol)
of triethylamine in 1600 ml of methylene chloride. The mixture
was stirred at from 3 to 22~C for 3 h, and the precipitated
hydrochloride was then filtered off with suction and washed with
THF, and the filtrate was concentrated under reduced pressure.
The residue was again stirred with 800 ml of THF, filtered off
with suction and washed with 1 1 of THF, and the filtrate was
concentrated under reduced pressure. This gave 366 g of the title
compound as a colorless oil of an HPLC purity of 95.3,
corresponding to a yield of 98.9 of theory. According to GC, the
purity was 85.2.
1H-NMR (400 MHZ, d6-DMSO) 8(ppm): 4.4 - 4.8 (broad/3H) NHZ/OH; 3.6
(s/3H) CH30; 3.52 (t/2H) and. 3.35 (t/2H) CHz-CH2
b) Methyl tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate
Over the course of 2 min, 22.4 g (0.746 mol) of paraformaldehyde
were added with stirring to a mixture of 100 g (0.746 mol) of
methyl N-amino-N-2-hydroxyethylcarbamate in 1500 ml of methylene
chloride. 8.5 g (0.045 mol) of p-toluenesulfonic acid were added,
and the mixture was then stirred at 42~C for 21 h, until the
precipitate had dissolved. The mixture was cooled to 20~C,
magnesium sulfate was added, the mixture was filtered and the
filtrate was concentrated under reduced pressure. This gave
111.8 g of the title compound as a colorless resin of a GC purity
of 850, corresponding to a yield of 85.80 of theory.
1H-NMR (500 MHZ, CF3COZD) 8(ppm): 5.09 (s/2H) CHZ; 4.02 (s/3H)
CH30; 3.8 - 4.25 (m/4H) CHZCHz
IR a (cm-i): C=O 1703
The precursors of the formulae IIb and X listed in Tables a) and
b) below were prepared in a similar manner.

0050~50~80 CA 02377143 2001-12-19
145
Table a)
HO(CH2)2~N,R
(X)
NH2
0 Compound R nD23 v [ cm-1 ] Yield
X
No.
1 C02CH3 _ _ 98. 9
2 COzC2H5 C=O 1695 cm-1, 88
NH2 3336 cm-1
3 C(O)SCH3 1.5458 85
4 C(O)SCZHS 1.5345 86
5 COZ-i-C3H7 C=O 1694 cm-1, 69
NHZ 3338 cm-1
6 C02-t-C4H9
7 C02-phenyl
g COZ-p-C1-phenyl
9 COZ-benzyl 1.5442 C=O 1706 cm-1, 62
NH2 3336 cm-1
10 C(S)OCH3
11 C02-n-CgHl7
12 C02CH2CHZC1 1.4988 C=O 1706 cm-1 65
13 COZ-cyclopentyl 1.4981 C=O 1695 cm-1 50
14 C02-n-C14H19 C=O 1700 cm-1 88
15 COCH3 1.4938 22
nDZ3 = refractive index at 23~C
~' [ cm-1 l IR bands
Table b)
N , R
i
o~N~
H

~~r~0~~r~~8~ CA 02377143 2001-12-19
146
Compound R nn23 v [cm-1] 1H-NMR Yield
IIb No. b.p. [b(PPm)) [$J
[~C/mbar]
m.p. [QC]
1 C02CH3 - - s.o. 85.5
2 COzC2H5 100-105/0.5 C=0: 1701 4.05 78
(q/2H),
0-CH2-C;
1.18
(t/3H)
CH3
3 C(O)SCH3 103-111/0.4 C=O: 1659 75
1.5542
4 C(O)SCzHS 1.5428 C=O: 1657 74
5 C02-i-C3H7 C=O: 1702 61
6 COy-t-C4Hg
7 C02-phenyl
8 C02-p-C1-phenyl
9 C02-benzyl 7.4-7.24 43
(m, 5H)
5.1
(s,2H)
10 C(S)OCH3
11 COZ-n-C$H17
12 C02CHZCHZC1 1.5130 C=O 1709 53
13 C02-cylcopentyl145-150/0.5 C=0 1700 51
14 C02-n-C14H2g 77-81 59
15 COCH3 C=O 1683 34
nD23 = refractive index at 23~C
m.p. - melting point
b.p. - boiling point at the stated pressure
II. Preparation of the compounds Ia and Ib
Example 1 (Compound Ib, No. 1, Table 7)
Methyl ter_rahydro-N-(2,4-dichloro-5-methoxyiminomethyl-
phenyl)-4H-L,3,4-oxadiazine-3-thiocarboxamide-4-carboxylar.e
Over the course of 5 min, 9.11 g (0.035 mol) of
2,4-dichlnro-5-methoxyiminomethylphenyl isothincyanate w~:cP added
with sti:rc.inc~ to 10.22 g (0.07 mol) of the compound from f~: in
1~0 ml of ter.rahydrofuran, and the mixture teas stirred a:. 2;e=o' For

~~.rJ~~5~08~ CA 02377143 2001-12-19
147
h and then at 40 to 50°C for 2 h. The reaction mixture was
concentrated under reduced pressure. The residue was taken up in
methylene chloride and fractionated over silica gel. This gave
11.9 g (78~ of theory) of the title compound of m.p. 80-83°C.
5
IR v (cm-1): C=O/C=S 1733, 1705
Example 2 (Compound Ib.2, Table 7)
Tetrahydro-N-(4-chloro-5-methoxyiminomethylphenyl)-4H-1,3,4-
oxadiazine-3-carboxamide
6.3 g (17.66 mmol) of methyl tetrahydro-N-(4-chloro-5-methoxy-
iminomethylphenyl)-4H-1,3,4-oxadiazine-3-carboxamide-4-carboxy-
late were initially charged in 150 ml of ethanol, and over the
course of 20 min, a solution of 0.8 g (19.42 mmol) of sodium
hydroxide in 50 ml of water was then added with stirring at 60 to
70°C. After a further 10 min of stirring, the clear solution was
cooled and substantially concentrated under reduced pressure. The
residue was admixed with 50 ml of water and, with stirring,
acidified with 1N hydrochloric acid, which resulted in evolution
of gas with formation of foam and precipitation. The resulting
mixture was extracted three times with rnethylene chloride. The
combined organic extracts were dried over magnesium sulfate and
concentrated under reduced pressure. This gave 4.9 g (83.60 of
theory) of the title compound as a colorless resin.
1H-NMR (400 MHZ d6-DMSO)8 (ppm): 8.4 (s/1H) CH=N; 8.2 (s/1H), 7.7
(m/1H), 7.36 (m/1H) phenyl; 4.0 (s/3H) N=OCH3
IR v (cm-1): C=O 1681
Example 3 (Compound Ib.3, Table 7)
Methyl tetrahydro-N-(2,4-dichloro-5-methoxyphenyl)-4H-1,3,4-
oxadiazine-3-carboxamide-4-carboxylate
With stirring, 0.3 g (1.666 mmol) of 30o strength sodium
methoxide was added to a solution of 0.5 g (1.505 mmo1) of
8-(2',4'-dichloro-5'-methyloxyphenyl)-4-oxa-7,9-dioxo-1,2,8--
triazabicyclo[~.3.0)nonane in 50 ml of methanol. The mixture was
stirred at 22°C for another 6 h. The reaction mixture was
concentrated under reduced pressure and partitioned between
methylene chloride and 1N hydrochloric acid. The organic ph~s~
was dried over magnesium sulfate and concentrated under r edu~:_ed

~1
CA 02377143 2001-12-19
148
pressure, giving 0.5 g (88.5 of theory) of the title compound as
colorless crystals of m.p. 160-163°C.
IR v (cm-1): C=0 1730, 1693
Example 4 (Compound Ib.S, Table 7)
Ethyl tetrahydro-N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4H-
1,3,4-oxadiazine-3-thiocarboxamide-4-carboxylate
With stirring, 0.17 g (2.473 mmol) of sodium ethoxide was added
to a solution of 0.8 g (2.249 mmol) of
8-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4-oxa-7-oxo-9-
thioxo-1,2,8-triazabicyclo[4.3.0]nonane in a mixture of 30 ml of
ethanol and 30 ml of methylene chloride, and the mixture was
stirred at 22°C for 1 h. 100 ml of methylene chloride were then
added, and the mixture was extracted 2 x with 1N hydrochloric
acid. The organic phase was dried and concentrated, and 0.9 g
(99.4 of theory) of the title compound were isolated as a crude
resin. Filtration over silica gel using methylene chloride gave
0.7 g of m.p. 143-145°C.
Example 5 (Compound Ib.95, Table 7)
Tetrahydro-N-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4H-I,3,4
-oxadiazine-3-thiocarboxamide-4-(N'-methoxycarbonyl)carboxamide
At 22°C, 0.22 g of methoxycarbonyl isocyanate (90~) is added to a
solution of 0.6 g of
tetrahydro-N-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4H-1,3,4
-oxadiazine-3-thiocarboxamite (Compound Ib, No. 5 from Table 7,
prepared by hydrolysis of Compound No. Ib.4 (Table 7, Example 4)
by the method described in Example 2, and the mixture was stirred
for 22 h. Concentration of the mixture under reduced pressure,
digestion with ether and isolation of the residue by filtration
with suction gave 0.6 g of the title compound of melting point
195°C.
In addition to the compounds described above, further substituted
ureas of the formulae Ia and Ib which were prepared in an
analogous manner are listed in Tables 7 and 8 below,

0050/50080 CA 02377143 2001-12-19
149
Table 7 (Compounds Ib No.l to No. 101 where Q = Q-1 and Z = O)
R3
~N~R
O( ~N. .N ~ ~ R4 I b
X
to
No. R X R3 R4 R5 m.p.. [C] or
IR: v [cm-1)
1 C02CH3 S C1 C1 CH=NOCH3 80 - 83C
2 H O H C1 CH=NOCH3 1681
3 C02CH3 O Cl C1 OCH3 160 - 163C
No. R X R3 R4 R5 m.p.. [C] or
IR: v [cm-1)
4 COzCH3 S F C1 OCHzC=CH 156 - 160C
5 H S F Cl OCH2C=-CH 124 - 128C
6 C02CH3 S F Cl O-C(=CHZ)C02CH3 68 - 71C
7 C02CH3 S F C1 CH=NOCH3 150 - 153C
8 COZCH3 O F Cl CO-O-C(CH3)3 60 - 65C
9 COyCH3 O H CI CH=NOCH3 153 - 155C
10 C02CH3 O F C1 OCHZC~CH 130C
11 COZC2H5 S F C1 OCH2C---CH 143 - 145C
12 COZC2H5 O F C1 OCHzC~CH
13 C02-iC3H7 S F C1 OCH2C---CH 118 - 123C
14 C02-iC3H7 O F C1 OCHZC=CH
15 C02-nC3H7 O F C1 OCH2C---CH
16 C02-nC3H7 S F C1 OCHZC---CH
17 COZCH3 S C1 C1 OCHZC---CH 141 - 143C
18 C02CH3 O C1 C1 OCH2C---CH
19 C02CH j S H C1 OCHZC---CH
20 COZCH3 O H C1 OCHZC=CH
21 COZCH3 S H Cl OCHZCOZCH3
22 COzCH3 0 H C1 OCHzCO2CH3
0 - -_~._
4 23 COZCH3 S C1 I OCHZCOZCH3
C1
24 COzCH3 O CI ~ OCHzCO2CH3
-- ~ ~
-
-
25 COZCH3 S F C OCHzCO2CH3 142C
1
26 COZCH3 0 ~ LOCHZCOzCH3
C
L
4 27 COZCH3 S F~ C::L~ OCHZCOo-nC5H11
28 C02CH3~~ O F ~ OCH2COz-nCSHli
C1-

~~c~~~c~~0$~ CA 02377143 2001-12-19
150
No. R X R3 R4 R5 m.p.: [C] or
IR: v [cm-1]
29 C02CH3 S C1 C1 SCH2C02CH3
30 COzCH3 0 C1 C1 SCH2C02CH3
31 C02CH3 S F C1 SCHzCOzCH3 129-132C
32 C02CH3 0 F C1 SCHzCO2CH3 1737, 1701
cm-1
33 COyCH3 S H C1 OCH(CH3)COzCH3
34 COzCH3 O H Cl OCH(CH3)C02CH3
35 C02CH3 S Cl Cl OCH(CH3)COZCH3
36 C02CH3 O C1 C1 OCH(CH3)C02CH3
37 COZCH3 S F C1 OCH(CH3)C02CH3 73 - 76C
15~38 C02CH3 0 F C1 OCH(CH3)C02CH3
39 C02CH3 S F C1 SCH(CH3)COzCH3 1735 cm-1
40 C02CH3 0 F C1 SCH(CH3)C02CH3
41 COyCH3 S H Cl C02CH3
42 C02CH3 O H C1 C02CH3
43 C02CH3 S C1 Cl C02CH3
44 C02CH3 O C1 C1 C02CH3
45 COZCH3 S F Cl C02CH3 185-187C
46 C02CH3 0 F C1 COzCH3
4 COZCH3 S H C1 C02C ( CH3 ) 2C02CH2CH=CH2
7
4 COZCH3 0 H C1 C02C ( CH3 ) yC02CHZCH=CH2
8
49 C02CH3 S C1 C1 C02C(CH3)2COzCH2CH=CH2
50 C02CH3 O C1 C1 COzC ( CH3 ) 2COZCHZCH=CH2
51 C02CH3 S F C1 C02C(CH3)2C02CHZCH=CHz
52 COZCH3 O F Cl C02C ( CH3 ) 2COZCHzCH=CHz
53 C02CH3 S F C1 C02CH2CHZOCH1
54 C02CH3 O F C1 COZCH2CH20CH3
55 COZCH3 S F C1 C(=NOCH3)OCH3
56 C02CH3 O F C1 C(=NOCH3)OCH3
57 C02CH3 S F C1 C(=NOCH3)OCH2COzCH3
58 COzCH3 0 F C1 C(=NOCH3)OCH2COzCH3
59 COZCH3 S F C1 C(O)N(CH3)OCH3
60 C02CH3 O F Cl C(O)N(CHg)OCH3
51 COZCH3 S C1 C1 CH=NOCH3
62 COzCH3 0 F C1 CH=NOCH3
03 C02CH3 S F C1 CEI=NOCH3 150 - 153C
0l COzCH3 O F C1 CH=DIOCZH3
65 ICOzCH3 ~S IF IC1ICH=NOC2H5

0050~5008~ CA 02377143 2001-12-19
151
No R X R3 R4 R5 m . p . : [
. oC ] or- ,
IR: v [cm-1]
66 C02CH3 O F Cl CH=NOCHzC02CH3
67 C02CH3 S F C1 CH=NOCHZC02CH3
68 C02CH3 O F C1 CH=NOCH(CH3)C02CH3
69 COZCH3 S F C1 CH=NOCH(CH3)C02CH3
70 C02CH3 0 F C CH=C(C1)C02C2H5
1
71 COZCH3 S F C1 CH=C(C1)C02C2H5
72 C02CH3 O F C1 CHz-CH(C1)C02CyH5
73 COZCH3 S F C CHZ-CH(Cl)COzC2H5
1
74 C02CH3 O F C1 CH=NOCH2C~CH
75 C02CH3 S F C1 CH=NOCH2C~CH
76 C(O)NHC02Et S F C1 O-cyclopentyl 195C decomp.
77 C02Et S F C1 OCHZCH=CHZ 118 - 122C
78 C02CH3 S F C1 OCH2CH=CH2 158 - 159C
79 COZ-iC3H7 S F C OCH2CH=CHp 139 - 140C
1
80 H S F C1 O-cyclopentyl 115 - 118C
81 C02CH3 S F C1 O-cyclopentyl 177 - 179C
82 H S Cl C1 COzH 168-170C
decomp.
83 COZEt O F C1 OCH3 56 - 58C
84 C(O)NHC02Et 0 H C1 CH=NOCH3 214-215C
decomp.
85 C02-iC3H7 S C1 Cl CN 140 - 143C
86 COZCzHS S F Cl COZCH3 160 - 163C
87 C(O)NHC02CH3 S F C1 O-cyclopentyl 190C decomp.
88 C(O)NHCOzCZHSS F C1 OCHzC=CH 172 - 174C
89 COZ-benzyl S F C1 OCHZC---CH 49 - 51C
90 C02-cyclo- S F Cl OCH2C=CH 114 - 116 C
pentyl
91 COZ-CH2CHZC1 S F C1 OCH2C---CH 1730 cm-1
92 C02-n-C14Hz9 S F C1 OCHZC=CH 35 - 36C
93 H S F C1 COzH 160C decomp.
94 C(O)NHCOZCH3 S F C1 OCHzC=CH 195C decomp.
95 COZCH3 S F C1 COz-i-C3H7 149 - 151C
g6 C02CH3 O F F H 92 - 93C
97 C02CH3 O F F NOZ 1734,1700 cm-1
gg H S F C1 OH 153 - 156C
gg H S F C1 OCHZCOzCH3 188C
100 COZCH3 S C1 Cl OCH3 1730,1704 cm-1
101 COZCH3 S F CN F 175 - 176C ii

~pr~0~5~p8~ CA 02377143 2001-12-19
I52
Table 8:(Compounds Ia No. 1 to No. 94 wherk~ Q = Q-1 and Z = O)
X
I) _
~N ~ N \ / R l a
H
R RS
No. R X R3 R4 R5 m.p.. [C] or
IR: v [cm-i]
1 COZCH3 S C1 C1 CH=NOCH3
2 H O H C1 CH=NOCH3 58 - 60C
3 C02CH3 O C1 C1 OCH3 1746 cm-1
4 C02CH3 S F C1 OCH2C---CH
5 H S F C1 OCH2C=-CH 157 - 158C
6 COZCH3 S F Cl O-C(=CH2)COyCH3
7 C02CH3 S F Cl CH=NOCH3
8 COZCH3 O F C1 CO-O-C(CH3)3
9 COZCH3 O H C1 CH=NOCH3
10 C02CH3 O F C1 OCH2C---CH 112 - 115C
11 C02C2H5 S F C1 OCH2C---CH
12 C02C2H5 O F C1 OCHZC---CH
13 C02-iC3H7 S F C1 OCH2C=CH
14 C02-iC3H7 O F C1 OCH2C---CH
15 CO2-nC3H7 O F C1 OCHZC~CH
16 C02-nC3H7 S F C1 OCH2C-=CH
17 COZCH3 S C1 Cl OCH2C---CH
18 C02CH3 O Cl Cl OCH2C---CH
19 C02CH3 S H C1 OCH2C---CH
20 C02CH3 O H C1 OCH2C---CH
21 C02CH3 S H C1 OCHZCOZCH3
22 C02CH3 0 H C1 OCH2C02C H3
23 COzCH3 S Cl C1 OCH2COZCH3
24 COZCH3 O C1 C1 OCHZCOZCH3
25 COZCH3 S F Cl OCHZC02CH3
26 COzCH3 O F C1 OCHZCOzCH3
27 COZCH3 S F C1 OCHZCOZ-nCSHii
28 COZCH3 O F C1 OCHZCOZ-nC5Hii
29 COZCH3 S C1 C1 SCHZCOzCH3 ._
30 CC~ZCH3 O C1 C1 SCHZCOZCH3
31 COZCH3 S F Cl SCHzCOZCH3

~~5~~500$0 CA 02377143 2001-12-19
153
No. R g R3 R4 R5 _. m,p. : [C]
or
IR: v [cm-1]
32 C02CH3 O F C SCHZC02CH3
1
33 C02CH3 S H C OCH(CH3)COZCH3
1
34 COzCH3 O H C1 OCH(CH3)C02CH3
35 COzCH3 S C1 C1 OCH(CH3)COzCH3
36 COzCH3 O C1 C1 OCH(CH3)C02CH3
37 C02CH3 S F C1 OCH(CH3)C02CH3
38 C02CH3 0 F Cl OCH(CH3)COyCH3
39 C02CH3 S F C1 SCH(CH3)C02CH3
40 COZCH3 O F C1 SCH(CH3)C02CH3
41 COzCH3 S H C1 C02CH3
42 COzCH3 O H C1 COZCH3
43 COZCH3 S C1 C1 COZCH3
44 COzCH3 O C1 C1 C02CHg
45 COzCH3 S F C1 C02CH3
46 C02CH3 O F C1 C02CH3
4 C02CH3 S H C C02C ( CH3 ) 2COzCH2CH=CH2
7 1
4 C02CH3 O H C1 C02C ( CH3 ) 2COZCH2CH=CHZ
8
49 COZCH3 S C1 C1 C02C(CH3)2COzCH2CH=CHZ
50 C02CH3 O C1 C1 C02C(CH3)ZC02CHZCH=CH2
51 C02CH3 S F C1 C02C ( CH3 ) 2CO2CHZCH=CH2
52 COZCH3 O F C1 C02C ( CH3 ) 2C02CH2CH=CH2
53 COzCH3 S F C COZCH2CHZOCH3
1
54 C02CH3 O F C1 COyCH2CHzOCH3
55 COzCH3 S F C1 C(=NOCH3)OCH3
56 COZCH3 O F C1 C ( =NOCH3 ) OCH3
57 COZCH3 S F C1 C(=NOCH3)OCHZCOzCH3
58 COZCH3 O F C1 C(=NOCH3)OCHyC02CH3
59 COZCH3 S F C1 C(O)N(CH3)OCH3
60 COpCH3 O F C1 C(O)N(CH3)OCH3
61 C02CH3 S C1 C1 CH=NOCH3
62 COZCH3 O F Cl CH=NOCH3
63 COpCH3 S F C1 CH=NOCH3
64 C02CH3 O F C1 CH=NOCZHS
65 COZCH3 S F C1 CH=NOCZHS
66 COZCH3 O F Cl CH=NOCHzCOZCH3
67 COZCH3 S F C1 CH=NOCHZCOZCH3
68 C02CH3 O F C CH=NOCH(CH3)C02CH3
1
69 C02CH3 S F C1 CH=NOCH(CH3)COZCH3

005050080 CA 02377143 2001-12-19
154
No. R X R3 R4 R5 m.p.: [C] or
IR: v [cm-1]
70 C02CH3 O F C1 CH=C(C1)COZC2H5
71 COzCH3 S F C1 CH=C(Cl)COZCZHS
72 C02CH3 O F C1 CHZ-CH(C1)C02C2H5
73 C02CH3 S F C1 CHZ-CH(C1)C02CZH5
74 COyCH3 O F Cl CH=NOCH2C~CH
75 C02CH3 S F C1 CH=NOCH2C~CH
76 C(O)NHCOZEt S F C1 OCH2C = CH 175C decomp.
77 C(O)NHCOZEt O F C1 OCH3 189 - 190C
7g H O C1 C1 OCH3 128 - 130C
7g H O F Cl OCH3 147 - 150C
80 H O C1 Cl CH=N-OCH3 210 - 213C
81 H O F C1 CH=N-OCH3 170 - 172C
82 C(O)NHCOZEt O C1 C1 CH=N-OCH3 189C
83 C(O)NHCOZEt O F C1 CH=N-OCH3 179 - 180C
84 H S F Cl CH=N-OCH3 175 - 176C
85 C(O)NHC02Et S F C1 CH=N-OCH3 181C decomp.
86 H S F C1 OCH(CH3)C02CH3(R) 1753 cm-1
87 C(O)NHCOZCZHgS F C1 OCH(CH3)C02CH3(R) 158 - 163C
88 C(O)NHC02CH3S F C1 OCH(CH3)C02CH3(R) 174 - 178C
8g H S F Cl C02CH3 175 - 178C
90 C(O)NHC02CH3S F C1 OCHZC---CH 184C decomp.
91 C(O)NHCOzCH3S F C1 COZCH3 160C decomp.
92 C(O)NHCOzCZHSS F C1 COZCH3 159C decomp.
93 C(O)NHC02CH30 F C1 CH=N-OCH3 180-183C
decomp.
94 C02CH3 O F C1 OCH3 61 - 64C
Example 6
Moreover, the compound of the formula Ib where Z = O, X = S, m =
0, R = C02CH3, where Q is a radical of the formula Q4 where R3 =
F, y = O and TR7 = propargyl, was prepared by reacting
7-fluoro-6-isothiocyanato-4-(2-propargyl)-2H-1,4-benzoxazin-
3(4H)one with methyl tetrahydro-4H-1,3,4-oxadiazine-4-
carboxylate. Melting point 190-193°C.
Example 7
N-[4'-Chloro-2'-fluoro-5'-methoxyiminomethylphenyl)-4H-1,3,4-
thiadiazine-4-carboxamide

0050~500$~ CA 02377143 2001-12-19
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At 22~C, 0.7 g (5.7 mmol) of thionyl chloride was added to a
mixture of 1.2 g of N-methyleneimino-N-2-hydroxyethyl-
N'-[4'-chloro-2'-fluoro-5'-(methoxyiminomethyl)phenyl]urea -
prepared according to Example la of DE 198.29.745.9 in 100 ml of
1,2-dichloroethane, and the mixture was stirred at 83~C for 2 h.
After cooling, the mixture was worked up by aqueous extraction,
giving, after removal of the solvent, 1.3 g of N-methyleneimino-
N-2-chloroethyl-N'-[4'-chloro-2'-fluoro-5'-(methoxyimino-
methyl)phenyl]urea of melting point 120-122~C.
1.2 g of the resulting chloroethyl compound and 0.7 g of thiourea
in 50 ml of DMSO were reacted at 22~C for 12 h and at 50~C for
1 h. The reaction mixture was then, at room temperature, stirred
into 65 ml of lOg by weight strength aqueous sodium hydroxide
solution, and the mixture was stirred at 20-30~C for another hour.
At the same temperature, 75 ml of 10~ by weight strength aqueous
hydrochloric acid were added, and the mixture was extracted three
times with dichloromethane. The organic phase was isolated, dried
and filtered through a bed of silica gel. Goncentration of the
solution gave 0.2 g of the title compound. Melting point
155-162~C.
The compounds Ia and Ib and their agriculturally useful salts are
suitable, both in the form of isomer mixtures and in the form of
the pure isomers, as herbicides. The herbicidal compositions
comprising Ia or Ib control vegetation on non-crop areas very
efficiently, especially at high rates of application. They act
against broad-leaved weeds and harmful grasses in crops such as
wheat, rice, maize, soya and cotton without causing any
significant damage to the crop plants. This effect is mainly
observed at low rates of application.
Depending on the application method used, the compounds Ia and
Ib, or the compositions comprising them, can additionally be
employed in a further number of crop plants for eliminating
undesirable plants. Examples of suitable craps are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus
officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec.
rapa, Brassica napus oar. napus, Brassica napus oar.
napobrassica, Brassica rapa oar. silvestris, Camellia sinensis,
Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus
sinensis, Coffea arabica (Coffea canephora, Coffea liberica),
Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis
guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium viti.folium),
Heliar~~chus annuus, Hevea brasiliensis, Ho~deum vulgare, Humulus

~~50~5~~$~ CA 02377143 2001-12-19
156
lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum
usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot
esculenta, Medicago sativa, Musa spec., Nicotiana tabacum
(N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,
Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum,
Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre,
Ricinus communis, Saccharum officinarum, Secale cereale, Solanum
tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao,
Trifolium pratense, Triticum aestivum, Triticum durum, Vicia
faba, Vitis vinifera and zea mays.
In addition, the compounds Ia and Ib may also be used in crops
which tolerate the action of herbicides owing to breeding,
including genetic engineering methods.
The herbicidal compositions or the active compounds can be
applied pre- or post-emergence. If the active compaunds are less
well tolerated by certain crop plants, application techniques may
be used in which the herbicidal compositions are sprayed, with
the aid of the spraying equipment, in such a way that they come
into contact as little as possible, if at all, with the leaves of
the sensitive crop plants, while the active compounds reach the
leaves of undesirable plants growing underneath, or. the bare soil
surface (post-directed, lay-by).
The compounds Ia and Ib, or the herbicidal compositions
comprising them, can be used, for example, in the form of
ready-to-spray aqueous solutions, powders, suspensions, also
highly concentrated aqueous, oily or other suspensions or
dispersions, emulsions, oil dispersions, pastes, dusts, materials
for broadcasting or granules, by means of spraying, atomizing,
dusting, broadcasting or watering. The use forms depend on the
intended aims; in any case, they should ensure a very fine
distribution of the active compounds according to the invention.
Essentially, suitable inert auxiliaries include:
mineral oil fractions of medium to high boiling point, such as
kerosene and diesel oil, furthermore coal tar oils and oils of
vegetable or animal origin, aliphatic, cyclic and aromatic
hydrocarbons, e.g. paraffin, tetrahydronaphthalene, alkylated
naphthalenes and their derivatives, alkylated benzenes and their
derivatives, alcohols such as methanol, ethanol, propanol,
butanol and cyclohexanol, ketones such as cyclohexanone, or
strongly polar solvents, e.g. amines such as N-methylpyrrolidone,
and water.

~~5~~5~08~ CA 02377143 2001-12-19
157
Aqueous use forms can be prepared from emulsion concentrates,
suspensions, pastes, wettable powders or water-dispersible
granules by adding water. To prepare emulsions, pastes or oil
dispersions, the substituted ureas, either as such or dissolved
in an oil or solvent, can be homogenized in water by means of a
wetting agent, tackifier, dispersant or emulsifier.
Alternatively, it is possible to prepare concentrates comprising
active substance, wetting agent, tackifier, dispersant or
emulsifier and, if desired, solvent or oil, which are suitable
for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth
metal salts and ammonium salts of aromatic sulfonic acids, e.g.
ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic
acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl
sulfates, lauryl ether sulfates and fatty alcohol sulfates, and
salts of sulfated hexa-, hepta- and octadecanols, and also of
fatty alcohol glycol ethers, condensates of sulfonated
naphthalene and its derivatives with formaldehyde, condensates of
naphthalene, or of the naphthalenesulfonic acids with phenol and
formaldehyde, polyoxyethylene octylphenol ether, ethoxylated
isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl
polyglycol ether, alkylaryl polyether alcohols, isotridecyl
alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl ethers or polyoxypropylene
alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol
esters, lignosulfite waste liquors or methylcellulose. Powders,
materials for broadcasting and dusts can be prepared by mixing or
grinding the active substances together with a solid carrier.
Granules, e.g. coated granules, impregnated granules and
homogeneous granules, can be prepared by binding the active
compounds to solid carriers. Solid carriers are mineral earths,
such as silicas, silica gels, silicates, talc, kaolin, limestone,
lime, chalk, bole, loess, clay, dolomite, diatomaceous earth,
calcium sulfate, magnesium sulfate, magnesium oxide, ground
synthetic materials, fertilizers such as ammonium sulfate,
ammonium phosphate and ammonium nitrate, ureas, and products of
vegetable origin, such as cereal meal, tree bark meal, wood meal
and nutshell meal, cellulose powders, or other solid carriers.
The concentrations o.f the active compounds Ia or Ib in the
ready-to-use preparations can be varied within wide ranges. In
general, the formulations comprise from 0.001 to 98o by weight,
preferably 0.01 to 95o by weight, of at least one active
compound. The active compounds are employed in a purity of from

CA 02377143 2001-12-19
158
90% to 100%, preferably 95% to 100% (according to the NMR
spectrum).
The compounds Ia and Ib according to the invention can be
formulated, for example, as follows:
I 20 parts by weight of the compound Ib.6 are dissolved in
a mixture composed of 80 parts by weight of alkylated
benzene, 10 parts by weight of the adduct of 8 to 10 mol
of ethylene oxide to 1 mol of oleic acid
N-monoethanolamide, 5 parts by weight of the calcium salt
of dodecylbenzenesulfonic acid and 5 parts by weight of
the adduct of 40 mol of ethylene oxide to 1 mol of castor
oil. Pouring the solution into 100,000 parts by weight of
water and finely distributing it therein gives an aqueous
dispersion which comprises 0.02% by weight of the active
compound.
II 20 parts by weight of the compound Ib.7 are dissolved in
a mixture composed of 40 parts by weight of
cyclohexanone, 30 parts by weight of isobutanol, 20 parts
by weight of the adduct of 7 mol of ethylene oxide to
1 mol of isooctylphenol and 10 parts by weight of the
adduct of 40 mol of ethylene oxide to 1 mol of castor
oil. Pouring the solution into 100,000 parts by weight of
water and finely distributing it therein gives an aqueous
dispersion which comprises 0.02% by weight of the active
compound.
III 20 parts by weight of the compound Ib.6 are dissolved in
a mixture composed of 25 parts by weight of
cyclohexanone, 65 parts by weight of a mineral oil
fraction of boiling point 210 to 280°C and 10 parts by
weight of the adduct of 40 mol of ethylene oxide to 1 mol
of castor oil. Pouring the solution into 100,000 parts by
weight of water and finely distributing it therein gives
an aqueous dispersion which comprises 0.02% by weight of
the active compound.
IV 20 parts by weight of the compound Ib.6 are mixed
thoroughly with 3 parts by weight of the sodium salt of
diisobutylnaphthalenesulfonic acid, 17 parts by weight o.f
the sodium salt of a lignosulfonic acid from a sulfite
waste liquor and 60 parts by weight of pul.verulent silica
gel, and 'the mixture is ground in a hammer mill. Finely
distributing the mixture in 20,000 parts by weight of

005050080 CA 02377143 2001-12-19
159
water gives a spray mixture which comprises 0.1~ by
weight of the active compound.
V 3 parts by weight of the compound Ib.6 are mixed with 97
parts by weight of finely divided kaolin. This gives a
dust which comprises 3~ by weight of the active compound.
VI 20 parts by weight of the compound Ib.7 axe mixed
intimately with 2 parts by weight of the calcium salt of
dodecylbenzenesulfonic acid, 8 parts by weight of fatty
alcohol polyglycol ether, 2 parts by weight of the sodium
salt of a phenol/urea/formaldehyde condensate and 68
parts by weight of a paraffinic mineral oil. This gives a
stable oily dispersion.
VII 1 part by weight of the compound Ib.6 is dissolved in a
mixture composed of 70 parts by weight of cyclohexanone,
parts by weight of ethoxylated isooctylphenol and 10
parts by weight of ethoxylated castor oil. This gives a
20 stable emulsion concentrate.
VIII 1 part by weight of the compound Ib.7 is dissolved in a
mixture composed of 80 parts by weight of cyclohexanone
and 20 parts by weight of Wettol~ EM 31 (nonionic
emulsifier based on ethoxylated castor oil). This gives a
stable emulsion concentrate.
To widen the activity spectrum and to achieve synergistic
effects, the substituted ureas Ia or Ib may be mixed with a large
number of representatives of other herbicidal or
growth-regulating active-compound groups and then applied
concomitantly. Suitable components for mixtures are, for example,
1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric
acid and its derivatives, aminotriazoles, anilides,
(het)aryloxyalkanoic acid and its derivatives, benzoic acid and
its derivatives, benzothiadiazinones,
2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,
benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates,
quinolinecarboxylic acid and its derivatives, chloroacetanilides,
cyclohexane-1,3-dione derivatives, diazines, dichloropropionic
acid and its derivatives, dihydrobenzofurans,
dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl
ethers, dipyridyls, halocarboxylic acids and their derivatives,
ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-
3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,
aryloxy- or heteroaryloxyphenoxypropionic esters, phenylacetic
acid and its derivatives, phenylpropionic acid and its

CA 02377143 2001-12-19
160
derivatives, pyrazoles, phenylgyrazoles, pyridazines,
pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,
sulfonamides, sulfonylureas, triazines, triazinones,
triazolinones, triazolecarboxamides and uracils.
It may furthermore be advantageous to apply the compounds Ia or
Ib, alone or else concomitantly in combination with other
herbicides, in the form of a mixture with other crop protection
agents, for example together with agents for controlling pests or
phytopathogenic fungi or bacteria. Also of interest is the
miscibility with mineral salt solutions, which are employed for
treating nutritional and trace element deficiencies.
Non-phytotoxic oils and oil concentrates may also be added.
The application rates of active compound are from 0.01 to 3,
preferably 0.1 to 1.0, kg/ha of active substance (a.s.),
depending on the control target, the season, the target plants
and the growth stage.
Part B
Use Examples
The herbicidal action of the substituted ureas of the formulae Ia
and Ib was demonstrated by greenhouse experiments:
The culture containers used were plastic pots containing loamy
sand with approximately 3.0~ of humus as the substrate. The seeds
of the test plants were sawn separately for each species.
For the pre-emergence treatment, the active compounds, which had
been suspended or emulsified in water, were applied directly
after sowing by means of finely distributing nozzles. The
containers were irrigated gently to promote germination and
growth and subsequently covered with transparent plastic hoods
until the plants had rooted. This cover caused uniform
germination of the test plants, unless this was adversely
affected by the active compound.
For the post-emergence treatment, the test plants were first
grown to a height of 3 to 15 cm, depending on the plant habit,
and then treated with the active compounds which had been
suspended or emulsified in water. To this end, the test plants
were either sown directly and grown in the same containers, or
they were first grown separately as seedlings and transplanted
into the test containers a few days prior to treatment. The

I4
~~50/50080 CA 02377143 2001-12-19
161
application rate for the post-emergence treatment was 62.5, 31.3
or 16.6 and 7.81 g of a.s./ha.
Depending on the species, the plants were kept at 10 to 25~C or 20
to 35~C. The test period extended over 2 to 4 weeks. During this
time, the plants were tended, and their response to the
individual treatments was evaluated.
The evaluation was carried out using a scale from 0 to 100. 100
means no emergence of the plants, or complete destruction of at
least the above-ground parts, and 0 means no damage, or normal
course of growth.
The plants used in the greenhouse experiments were of the
following species:
Bayer code Common name
ABUTH velvet leaf
common amaranth
CHEAL lambsquarters (goosefoot)
COMBS commelinal bengal
GALAP harrit cleavers
IPOSS morning glory
POLPE redshank
PHBPU common morning glory
SOLNI black nightshade
vERSS speedwell
TRZAW winter wheat
At an application rate of 62.5, 31.3 or 16.6 and 7.81 g of
a.s./ha, the compounds are highly effective in controlling
undesired broad-leaved plants by the post-emergence method.
The numbers given below for the compounds Ia and Ib relate to the
numbers of Tables 7 and 8.
The herbicidal activities given below were determined on
postemergence application of the compounds in the greenhouse.
45

005~~5~0$0 CA 02377143 2001-12-19
162
Example compound Ib No.6
10 O/
Application rate 62.5 31.3 (g of a.s./ha)
Test plants
ABUTH 100 100
CHEAL 100 100
IPOSS 100 100
SOLNI 100 100
VERSS 100 100
Example compound Ib No.7
i
~N O
.~N N
CI
3 0 p-
Application rate 15.6 7.8 (g of a.s./ha)
Test plants
ABUTH 100 100
CHEAL 100 I00
IPOSS 100 100
SOLNI 100 100
45

005050080 CA 02377143 2001-12-19
163
Example compound Ib No. 17
~h2C=CH
Application rate 62.5 31.3 (g of a.s./ha)
Test plants
ABUTH 100 100
CHEAL 100 100
IPOSS 98 98
SOLNI 100 100
VERSS 100 80
Example compound Ib No. 37
N~O~
~N N
CI
~O/
CH3
Application rate 62.5 31.3(g of a.s./ha)
Test plants
TRZAW 20 10
ABUTH 100 100
CHEAL 100 100
IPOSS 100 100
SOLNI 100 100
VERSS 100 100
45

~05~~5~0$~ CA 02377143 2001-12-19
164
Example compound Ib No. 81
O
N"O ~
~N N
S
Application rate 62.5 31.3 (g of a.s./ha)
Test plants
ABUTH 100 100
CHEAL 100 100
IPOSS 100 100
SOLNI 100 100
VERSS 100 100
Example compound Ib No. 78
I
CI
U
~H2CH=CH2
Application rate 62.5 31.3 (g of a.s./ha)
Test plants
ABUTH 100 100
CHEAI, 100 100
IPOSS 100 100
SOLNI 100 100
VERSS 100 100
Example compound Ia No. 76
Application 15.6 7.8 (g of a.s./haj
rate

0~50~5~080 CA 02377143 2001-12-19
165
Test plants
ABUTH loo loo
loo loo
CHEAL 100 100
COMBE I00 100
POLPE 100 100
Example compoundIa No. 4
10Application rate 15.6 7.8 (g of a.s./ha)
Test plants
ABUTH 100 100
~gE 100 100
15GALAP 98 98
POLPE 100 100
Example compoundIa,No. 92
20Application rate 7.8 3.9 (g of a.s./ha)
Test plants
ABUTH 100 98
~p,RE 10 0 10 0
25COMBE 100 90
POLPE 100 100
Example compoundIb No. 94
30Application rate 15.6 7.8 (g of a.s./ha)
Test plants
ABUTH 100 85
p~p,~ ' 100 100
35POLPE 100 100
Example compoundIb No. 32
Application rate 31.3 15.6 (g of a.s./ha)
40
Test plants
ABUTH 100 100
100 100
PHBPU 100 100
45POLPE 100 98

CA 02377143 2001-12-19
166
Compound from Example 6
1
I
S
CH2C~CH
Application rate 15.6 7.8 (g of a.s./ha
Test plants
ABUTH 100 100
AMARE __. 100 100
CHEAL 100 100
POLPE 100 100
25
35
45

Representative Drawing