Note: Descriptions are shown in the official language in which they were submitted.
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Novel 1-aryl-4-thiouracils
The present invention relates to novel 1-aryl-4-thiouracils of
the formula I
R1 X R6
.N ~ Y
S N ~ ~ RS
Ry R3 R4
where:
X is oxygen or sulfur;
R1 is hydrogen, amino or C1-C6-alkyl;
R2 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl;
R3 is hydrogen, halogen, C1-C6-alkyl or halomethyl;
R4 is hydrogen or halogen;
R5 is cyano, halogen, -CO-NH2, -CS-NH2 or
-OC(R8,R9)-CO-0(C1-C6-alkyl);
Y is nitrogen, the methine group or together with R6 is a
bridge >C-O-C(R1~)=N-;
R6 together with R5 is a radical -N(R~)-CZ1-C(R8',R9')-O-,
which is attached to R5 via the oxygen, or
1) is hydrogen, hydroxyl, mercapto, cyano, nitro,
halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-haloalkoxy, C1-C6-haloalkylthio,
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,
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2) 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 to three
substituents, in each case 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-ORii,
- the phenyl, phenoxy or phenylsulfonyl group,
which may be unsubstituted or may carry one to
three substituents, in each case selected from
the group consisting of halogen, vitro, cyano,
Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and
(Ci-C6-alkoxy)carbonyl,
- a group -CO-R12, -CO-OR12, -CO-SRi2,
-CO-N(R12)-R13, _pC0-R12, -OCO-OR12, -OCO-SR12,
-OCO-N(R12)-R13, _N(R12)-R13 and -C(R14)=N-ORii;
3) is -CZ2-RiS~ _C(NR16)_R15~ _C(R15) (Z3R17) (Z4R18)
i
_G(R15)=C(R19)_CN~ _G(Ri5)=G(R19)_GO_R2o~
_GH(R15)_CH(R19)_Cp_R20~ _C(R15)=C(R19)_CH2_Cp_R20~
_G(R15)=G(R19)_G(R21)=G(R22)_Gp_R2o~
_C(R15)=C(R19)_CH2_CH(R23)_Cp_R20~ _Cp_OR24, -CO-SR24,
-CO-N(R24)-ORii, -C=C-CO-NH-ORii,
-G=C-CO-N(R24)-ORii, -C=C-CS-NH-ORii,
_C - C _CS _N ( R24 ) _OR11 ~ _C ( R15 ) =C ( R19 ) _Cp_NH-ORi
i ,
_G ( R15 ) =G ( R19 ) _GO_N ( R24 ) _ORll ~
-C(Ri5)=C(R19)_CS_NH-ORii,
_C(R15)=C(R19)_CS_N(R24)_ORii,
_G(R15)=G(R19)_G(R14)=N_pRll~ _G(R14)=N_~R11~
_G=G_G(R14)=N_pRll~ _C(Z3R17) (Z4R18)_pR24~
-G(Z3R17)(Z4R18)_SR24~ _G(Z3Ri7)(Z4R18)_N(R25)R26~
_N(R25)_R26 or _CO-N(R25)-R26;
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Z1, Zz, Z3, Z4 independently of one another are each oxygen
or sulfur;
R~ is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl,
C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy,
C3-C6-cycloalkyl or C3-C6-cycloalkoxy, where each of the 8
last mentioned radicals may, if desired, carry one to
three substituents, in each case selected from the group
consisting of vitro, cyano, halogen, =O, =N-OR11',
C1-C6-alkoxy, -CO-Rlz', -CO-ORlz', -CO-SRlz' and
-C(R14~)=N-OR11'i
Rg, R9, R8', R9' independently of one another are each
hydrogen, cyano or C1-C6-alkyl;
R1~ is hydrogen, halogen, C1-C6-alkyl, C3-C6-alkenyl,
C3-C6-alkynyl, C1-C6-alkoxy, C3-C6-alkenyloxy,
C3-C6-alkynyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkoxy,
where each of the 8 last mentioned radicals may, if
desired, carry one to three substituents, in each case
selected from the group consisting of vitro, cyano,
halogen, =O, =N-OR11 " , C1-C6-alkoxy, -CO-Rlz " ,
-CO-ORl z " , -CO-SRl z " and -C ( R14 " ) =N-ORl1 ~ ' ;
Rll, R11', R11~' independently of one another are each 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-Cz-C6-alkenyl,
(C1-C6-alkyl)carbonyloxy-C1-C6-alkyl or
phenyl-C1-C6-alkyl, where the phenyl ring may, if
desired, 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;
Rlz, Rlz' , R12' ' independently of one another are each
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 group and the phenyl
ring of the phenyl alkyl group may be unsubstituted or
may carry one to three radicals, in each case selected
from the group consisting of halogen, vitro, cyano,
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C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and
(C1-C6-alkyl)carbonyl;
R13 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;
R14, R14~, R14~~ independently of one another are each
- hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy,
C1-C6-alkylthio, C1-C6-haloalkylthio,
(C1-C6-alkyl)carbonyloxy,
(C1-C6-haloalkyl)carbonyloxy, C1-C6-alkylsulfonyloxy
or C1-C6-haloalkylsulfonyloxy,
where the 11 last mentioned radicals may carry one of
the following substituents: hydroxy, 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-(G1-C6-alkyl)aminocarbonyl;
- a 3- to 7-membered azaheterocycle which is attached
to the nitrogen atom via a carbonyl bridge and which,
in addition to carbon ring members, may also contain
an oxygen or sulfur atom as ring member;
- (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, 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;
- 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, vitro, halogen,
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C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl;
R15 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
5 CZ-C6-alkenyl, C2-C6-alkynyl, Cg-C6-cycloalkyl,
C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R16 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-C~-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(R2~)R28,
is phenyl, which for its part may additionally carry one
to three substituents, in each case selected from the
group consisting of cyano, nitro, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, CZ-C6-alkenyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl,
is phenyl-C1-C6-alkoxy, phenyl-C3-C6-alkenyloxy or phenyl-
C3-C6-alkynyloxy, where in each case one or two methylene
groups of the carbon chains may be replaced by -O-, -S-
or -N(C1-C6-alkyl)- and where each phenyl ring may be
unsubstituted or may for its part carry one to three
substituents, in each case selected from the group
consisting of cyano, nitro, halogen, Ci-C6-alkyl,
C1-C6-haloalkyl, Cz-C6-alkenyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl,
is heterocyclyl, heterocyclyl-C1-C6-alkoxy,
heterocyclyl-C3-C6-alkenyloxy or
heterocyclyl-C3-C6-alkynyloxy, where in each case one
or
two methylene groups of the carbon chains may be replaced
by -O-, -S- or -N(C1-C6-alkyl)- and where each
heterocycle may be 3- to 7-membered, saturated,
unsaturated or aromatic and contains one to four
heteroatoms, selected from the group consisting of two
oxygen atoms, two sulfur atoms and four nitrogen atoms,
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and is either unsubstituted or for its part carries one
to three substituents, in each case 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;
R1~, R18 independently of one another are each 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
one member of this chain may be replaced by a bridge -O-,
-S-, -N=, -NH- or -N(C1-C6-alkyl) which is not adjacent
to the variables Z3 and Z4, and where the carbon chain
may additionally carry one to three radicals, in each
case selected from the group consisting of cyano, vitro,
amino, halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy,
Cz-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 which for
its part may be unsubstituted or may carry one to three
substituents, in each case selected from the group
consisting of cyano, vitro, amino, halogen, C1-C6-alkyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl,
and where the carbon chain may also be substituted by a
fused-on or spiro-linked 3- to 7-membered ring which may
contain one or two heteroatoms as ring members, selected
from the group consisting of oxygen, sulfur, nitrogen and
nitrogen substituted by C1-C6-alkyl, 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;
R19 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;
R2~ is hydrogen, O-RZ9, S-Rz9, C1-C6-alkyl, which may
additionally carry one or two C1-C6-alkoxy substituents,
is C2-C6-alkenyl, CZ-C6-alkynyl, C1-C6-haloalkyl,
C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl,
C1-C6-alkyliminooxy, -N(Rz5)R26 or phenyl, which may be
unsubstituted or may carry one to three substituents, in
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each case selected from the group consisting of cyano,
nitro, halogen, C1-C6-alkyl, CZ-C6-alkenyl,
C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R21 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(R25)R2s
or phenyl, which for its part may additionally 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;
R22 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy,
C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or
(C1-C6-alkoxy)carbonyl;
R23 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
Rz4, Rz9 independently of one another are each 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 or a 3- to 7-membered
azaheterocycle which is attached to the nitrogen atom
via a carbonyl bridge and which, in addition to
carbon ring members, may also contain an oxygen or
sulfur atom as ring member;
or are (C1-C6-alkyl)carbonyl,
(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,
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;
R25, Rz6, R2~, R2a independently of one another are each
hydrogen, C1-C6-alkyl, C3-C6-alkenyl, Cz-C6-alkynyl,
C3-C6-cycloalkyl, C1-C6-haloalkyl,
C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl,
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(C1-C6-alkoxy)carbonyl,
(C1-C6-alkoxy)carbonyl-C1-C6-alkyl,
(C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the
alkenyl chain may additionally carry one to three
halogen and/or cyano radicals,
or are C1-C6-alkylsulfonyl, (C1-C6-alkoxy)carbonyl-
C1-C6-alkylsulfonyl, phenyl or phenylsulfonyl, where
the two 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,
C3-C6-alkenyl, C1-C6-alkoxy and
(C1-C6-alkoxy)carbonyl,
or R25 and R26 and/or Rz7 and Rze together with the respective
linking 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 and enol ethers of the
compound I.
Furthermore, the invention relates to
- the use of the compounds I as herbicides,
- herbicidal compositions which comprise the compounds I as
active ingredients,
- processes for preparing the compounds I and herbicidal
compositions using the compounds I, and also
- methods for controlling undesirable vegetation using the
compounds I.
Substituted 1-phenyluracil derivatives are already provided by WO
97/05117, and they have been attributed herbicidal activity in
that publication.
However, the herbicidal properties of the known herbicidally
active 1-phenyluracils with regard to the harmful plants are not
always entirely satisfactory.
It is an object of the present invention to provide novel
herbicidally active 1-aryl uracils which allow better selective
control of undesirable plants.
we have found that this object is achieved by the
1-aryl-4-thiouracils of the formula I defined at the outset.
Furthermore, we have found herbicidal compositions which comprise
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the compounds I and have very good herbicidal activity.
Furthermore, we have found processes for preparing these
compositions and methods for controlling undesirable vegetation
using the compounds I.
Depending on the substitution pattern, the compounds of the
formula I can contain one or more chiral centers, in which case
they exist in the form of enantiomer or diastereomer mixtures.
For compounds I having at least one olefinic radical, E/2 isomers
may also be possible. The invention relates both to the pure
enantiomers or diastereomers and to mixtures thereof.
Agriculturally useful salts are especially the salts of those
cations or the acid addition salts of those acids whose cations
or anions have no negative effect on the herbicidal activity of
the compounds I. Thus, particularly suitable cations are the ions
of the alkali metals, preferably sodium and potassium, the
alkaline earth metals, preferably calcium, magnesium and barium,
and the transition metals, preferably manganese, copper, zinc and
iron, and also the ammonium ion which may, if desired, carry from
one to four C1-C4-alkyl substituents and/or a phenyl or benzyl
substituent, preferably diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, furthermore
phosphonium ions, sulfonium ions, preferably
tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably
tri(C1-CQ-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 also the anions of C1-C4-alkanoic acids, preferably
formate, acetate, propionate and butyrate.
The organic moieties mentioned in the definition of R1 to R3, R5
to RZ9 and on phenyl, cycloalkyl and heterocyclyl rings are
collective terms for individual listings 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 represents in each case fluorine, bromine,
chlorine or iodine, in particular fluorine or chlorine.
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Examples of other meanings are:
- C1-CQ-alkyl: CH3, C2H5, n-propyl, CH(CH3)2, n-butyl,
CH(CH3)-CZHS, 2-methylpropyl or C(CH3)3, in particular CH3,
5 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, CHZF,
10 CHF2, CF3, CHzCl, 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-chloroethyl, 1-(bromomethyl)-2-bromoethyl,
4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or
nonafluorobutyl, in particular CHzF, CHFZ, CF3, CHzCl,
2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
- C1-C6-alkyl: C1-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, C2H,, r_-propyl,
CH(CH3)Z, n-butyl, C(CH3)3, n-pentyl or n-hexyl;
- C1-C6-haloalkyl: C1-C6-alkyl 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-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,
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,
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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-yl, 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-phenylbut-1-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy,
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,
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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-CzHS, CO-CHZ-CyHS,
CO-CH(CH3)2, n-butylcarbonyl, CO-CH(CH3)-CzH5, CO-CH2-CH(CH3)2,
CO-C(CH3)3, n-pentylcarbonyl, 1-methylbutylcarbonyl,
2-methylbutylcarbonyl, 3-methylbutylcarbonyl,
1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,
2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl,
n-hexylcarbonyl, 1-methylpentylcarbonyl,
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-CZHS 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,
chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl,
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-difluoroethylcarbonyl,
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,
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3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl,
3,3,3-trichloropropylcarbonyl,
2,2,3,3,3-pentafluoropropylcarbonyl,
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-ethylbutyl-
carbonyloxy, 2-ethylbutylcarbonyloxy,
1,1,2-trimethylpropylcarbonyloxy,
1,2,2-trimethylpropylcarbonyloxy,
1-ethyl-1-methylpropylcarbonyloxy or
1-ethyl-2-methylpropylcarbonyloxy, in particular acetyloxy;
- (C1-C6-haloalkyl)carbonyloxy: a (C1-C6-alkyl)carbonyloxy
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,
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2,2,2-trifluoroethylcarbonyloxy,
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-trichloropropylcarbonyloxy,
2,2,3,3,3-pentafluoropropylcarbonyloxy,
heptafluoropropylcarbonyloxy,
1-(fluoromethyl)-2-fluoroethylcarbonyloxy,
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-dimethylpropylcarbonylthio,
2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio,
n-hexylcarbonylthio, 1-methylpentylcarbonylthio,
2-methylpentylcarbonylthio, 3-methylpentylcarbonylthio,
4-methylpentylcarbonylthio, 1,1-dimethylbutylcarbonylthio,
1,2-dimethylbutylcarbonylthio, 1,3-dimethylbutylcarbonylthio,
2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio,
3,3-dimethylbutylcarbonylthio, 1-ethylbutylcarbonylthio,
2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio,
1,2,2-trimethylpropylcarbonylthio,
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1-ethyl-1-methylpropylcarbonylthio or
1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;
- (C1-C6-haloalkyl)carbonylthio: a (C1-C6-alkyl)carbonylthio
5 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,
10 dichlorofluoroacetylthio, chlorodifluoroacetylthio,
2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio,
2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio,
2,2-difluoroethylcarbonylthio,
2,2,2-trifluoroethylcarbonylthio,
15 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-difluoropropylcarbonylthio, 2-chloropropylcarbonylthio,
3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio,
2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio,
3,3,3-trifluoropropylcarbonylthio,
3,3,3-trichloropropylcarbonylthio,
2,2,3,3,3-pentafluoropropylcarbonylthio,
heptafluoropropylcarbonylthio,
1-(fluoromethyl)-2-fluoroethylcarbonylthio,
1-(chloromethyl)-2-chloroethylcarbonylthio,
1-(bromomethyl)-2-bromoethylcarbonylthio,
4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio,
4-bromobutylthio or nonafluorobutylthio, in particular
trifluoroacetylthio;
- (C1-C6-alkyl)carbamoyloxy: methylcarbamoyloxy,
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-dimethylpropylcarbamoyloxy, 1-ethylpropylcarbamoyloxy,
n-hexylcarbamoyloxy, 1-methylpentylcarbamoyloxy,
2-methylpentylcarbamoyloxy, 3-methylpentylcarbamoyloxy,
4-methylpentylcarbamoyloxy, 1,1-dimethylbutylcarbamoyloxy,
1,2-dimethylbutylcarbamoyloxy, 1,3-dimethylbutylcarbamoyloxy,
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2,2-dimethylbutylcarbamoyloxy, 2,3-dimethylbutylcarbamoyloxy,
3,3-dimethylbutylcarbamoyloxy, 1-ethylbutylcarbamoyloxy,
2-ethylbutylcarbamoyloxy, 1,1,2-trimethylpropylcarbamoyloxy,
1,2,2-trimethylpropylcarbamoyloxy,
1-ethyl-1-methylpropylcarbamoyloxy or
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
substituted by fluorine, chlorine, bromine and/or iodine,
i.e., for example, chloromethylcarbamoyloxy,
dichloromethylcarbamoyloxy, trichloromethylcarbamoyloxy,
fluoromethylcarbamoyloxy, difluoromethylcarbamoyloxy,
trifluoromethylcarbamoyloxy, chlorofluoromethylcarbamoyloxy,
dichlorofluoromethylcarbamoyloxy,
chlorodifluoromethylcarbamoyloxy, 2-fluoroethylcarbamoyloxy,
2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy,
2-iodoethylcarbamoyloxy, 2,2-difluoroethylcarbamoyloxy,
2,2,2-trifluoroethylcarbamoyloxy,
2-chloro-2-fluoroethylcarbamoyloxy,
2-chloro-2,2-difluoroethylcarbamoyloxy,
2,2-dichloro-2-fluoroethylcarbamoyloxy,
2,2,2-trichloroethylcarbamoyloxy,
pentafluoroethylcarbamoyloxy, 2-fluoropropylcarbamoyloxy,
3-fluoropropylcarbamoyloxy, 2,2-difluoropropylcarbamoyloxy,
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-pentafluoropropylcarbamoyloxy,
heptafluoropropylcarbamoyloxy,
1-(fluoromethyl)-2-fluoroethylcarbamoyloxy,
1-(chloromethyl)-2-chloroethylcarbamoyloxy,
1-(bromomethyl)-2-bromoethylcarbamoyloxy,
4-fluorobutylcarbamoyloxy, 4-chlorobutylcarbamoyloxy,
4-bromobutylcarbamoyloxy or nonafluorobutylcarbamoyloxy, in
particular trifluoromethylcarbamoyloxy;
- C1-C6-alkoxy: for example OCH3, OC2H5, OCH2-C2H5, OCH(CH3)2.
n-butoxy, OCH(CH3)-C2H5, OCHz-CH(CH3)z, OC(CH3)3, n-pentoxy,
1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,
1,1-dimethylpropoxy, 1,2-dimethylpropoxy,
2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy,
1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,
4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,
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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 1-ethyl-2-methylpropoxy, in
particular OCH3, OCzHS or OCH(CH3)zJ
- 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,
OCH2-CHZ-OH, OCH(CyHS)-OH, OCH2-CH(CH3)-OH,
3-hydroxyprop-1-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-(CHZ-OH)eth-1-yloxy,
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1-(CHZ-OH)-1-(CH3)eth-1-yloxy or 1-(CH2-OH)prop-1-yloxy, in
particular OCHz-OH or OCH2-CH2-OH;
cyano-C1-C6-alkoxy: for example OCH2-CN, OCH(CH3)-CN,
OCHz-CH2-CN, OCH(CZHS)-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-(CHZ-CN)eth-1-yloxy, 1-(CH2-CN)-1-(CH3)eth-1-yloxy or
1-(CH2-CN)prop-1-yloxy, in particular OCH2-CN or OCHZ-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;
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- (C1-C6-alkoxy)carbonyl: for example CO-OCH3, CO-OCzH5,
CO-CHy-CZHS, CO-OCH(CH3)y, n-butoxycarbonyl, CO-OCH(CH3)-CZHS,
CO-OCH2-CH(CH3)2, CO-OC(CH3)3, n-pentoxycarbonyl,
1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,
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)2 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,
I,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,
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3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio,
1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio,
1,1-dimethylpropoxycarbonylthio,
1,2-dimethylpropoxycarbonylthio, 1-methylpentoxycarbonylthio,
5 2-methylpentoxycarbonylthio, 3-methylpentoxycarbonylthio,
4-methylpentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio,
1,2-dimethylbutoxycarbonylthio,
1,3-dimethylbutoxycarbonylthio,
2,2-dimethylbutoxycarbonylthio,
10 2,3-dimethylbutoxycarbonylthio,
3,3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio,
2-ethylbutoxycarbonylthio,
1,1,2-trimethylpropoxycarbonylthio,
1,2,2-trimethylpropoxycarbonylthio,
15 1-ethyl-1-methylpropoxycarbonylthio or
1-ethyl-2-methylpropoxycarbonylthio, in particular
methoxycarbonylthio, ethoxycarbonylthio or
1-methylethoxycarbonylthio;
20 - C1-C6-alkylthio: SCH3, SC2H5, SCHZ-CzHS, 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, 1,1-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 SCZHS;
- 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, SCzFS, 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,
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21
1-(fluoromethyl)-2-fluoroethylthio,
1-(chloromethyl)-2-chloroethylthio,
1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,
4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio,
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
2,2,2-trifluoroethylthio;
C1-C6-alkylsulfinyl: SO-CH3, SO-CZHS, n-propylsulfinyl,
1-methylethylsulfinyl, n-butylsulfinyl,
1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1,1-dimethylethylsulfinyl, n-pentylsulfinyl,
1-methylbutylsulfinyl, 2-methylbutylsulfinyl,
3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl,
1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl,
1-ethylpropylsulfinyl, n-hexylsulfinyl,
1-methylpentylsulfinyl, 2-methylpentylsulfinyl,
3-methylpentylsulfinyl, 4-methylpentylsulfinyl,
1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,
1,3-dimethylbutylsuifinyl, 2,2-dimethylbutylsulfinyl,
2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,
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;
- C1-C6-alkylsulfonyl: S02-CH3, SOz-C2H5, n-propylsulfonyl,
S02-CH(CH3)2, n-butylsulfonyl, 1-methylpropylsulfonyl,
2-methylpropylsulfonyl, SOZ-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;
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- C1-C6-alkylsulfonyloxy: 0-SOy-CH3, O-S02-CzHS,
n-propylsulfonyloxy, O-SO2-CH(CH3)Z, n-butylsulfonyloxy,
1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy,
O-SOZ-C(CH3)3, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy,
2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy,
1,1-dimethylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyloxy,
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-SOy-0-, CH(C1)2-SOy-O-, C(C1)3-S02-O-, FCHy-SOy-O-,
CHF2-SOZ-O-, CF3-SOZ-O-, chlorofluoromethyl-SOz-O-,
dichlorofluoromethyl-SOZ-O-, chlorodifluoromethyl-SOz-O-,
1-fluoroethyl-SOZ-0-, 2-fluoroethyl-SOZ-O-,
2-chloroethyl-SOZ-O-, 2-bromoethyl-S02-O-, 2-iodoethyl-S02-O-,
2,2-difluoroethyl-S02-O-, 2,2,2-trifluoroethyl-S02-O-,
2-chloro-2-fluoroethyl-SOZ-O-,
2-chloro-2,2-difluoroethyl-S02-O-,
2,2-dichloro-2-fluoroethyl-S02-O-,
2,2,2-trichloroethyl-S02-O-, C2F5-S02-O-,
2-fluoropropyl-SOZ-O-, 3-fluoropropyl-S02-O-,
2,2-difluoropropyl-SOz-O-, 2,3-difluoropropyl-S02-0-,
2-chloropropyl-S02-O-, 3-chloropropyl-S02-O-,
2,3-dichloropropyl-SOZ-O-, 2-bromopropyl-S02-0-,
3-bromopropyl-S02-O-, 3,3,3-trifluoropropyl-S02-O-,
3,3,3-trichloropropyl-S02-O-,
2,2,3,3,3-pentafluoropropyl-SOz-O-, CZFS-CFz-SOZ-O-,
1-(fluoromethyl)-2-fluoroethyl-S02-O-,
1-(chloromethyl)-2-chloroethyl-SOZ-O-,
1-(bromomethyl)-2-bromoethyl-S02-O-, 4-fluorobutyl-SOZ-O-,
4-chlorobutyl-S02-O-, 4-bromobutyl-S02-O-, C2F5-CF2-CFZ-SOZ-O-,
5-fluoropentyl-SOZ-O-, 5-chloropentyl-S02-O-,
5-bromopentyl-S02-O-, 5-iodopentyl-S02-O-,
5,5,5-trichloropentyl-SOZ-O-, CZFS-CFZ-CFZ-CF2-SOy-O-,
6-fluorohexyl-SOZ-O-, 6-chlorohexyl-S02-O-,
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23
6-bromohexyl-S02-O-, 6-iodohexyl-S02-O-,
6,6,6-trichlorohexyl-S02-O- or dodecafluorohexyl-S02-O-, in
particular CF3-SOZ-0-;
- (C1-C6-alkyl)aminocarbonyl: (C1-CQ-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, 1-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-methylpropyl)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,
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N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-
N-propylaminocarbonyl,
N-(1,1-dimethylethyl)-N-propylaminocarbonyl,
N-butyl-N-(1-methylethyl)aminocarbonyl,
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;
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- C1-C6-alkylideneaminoxy: acetylideneaminoxy,
1-propylideneaminoxy, 2-propylideneaminoxy,
1-butylideneaminoxy, 2-butylideneaminoxy or
2-hexylideneaminoxy, in particular acetylideneaminoxy or
5 2-propylideneaminoxy;
C1-C6-alkyliminooxy: methyliminooxy, ethyliminooxy,
n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy,
1-methylpropyliminooxy, 2-methylpropyliminooxy,
10 n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy,
2-methylpentyliminooxy, 3-methylpentyliminooxy or
4-methylpentyliminooxy, in particular methyliminooxy,
ethyliminooxy or 1-methylethyliminooxy;
15 - 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)Z, CO-NH-(CH2)3-CH3,
CO-NH-CH(CH3)-CZHS, CO-NH-CHZ-CH(CH3)y, CO-NH-C(CH3)3.
CO-NH-(CHZ)4-CH3, 1-methylbutylaminocarbonyl,
20 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,
2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl,
n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,
1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,
2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,
25 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 and
1-ethyl-2-methylpropylaminocarbonyl, and, preferably
(C1-C4-alkyl)aminocarbonyl which is substituted by
C1-C6-alkoxy as mentioned above, i.e., for example,
CO-NH-CH2-OCH3 or CO-NH-CHZ-OCZHS;
- C1-C6-alkoxyamino-Ci-C6-alkyl: for example, CHZ-NH-OCH3,
CHy-NH-OC2H5, CHZ-NH-OCHZ-C2H5, CH2-NH-OCH(CH3)Z,
CHz-NH-OCH2-CHZ-C2H5, CHy-NH-OCH(CH3)-C2H5,
CH2-NH-OCH2-CH(CH3)2, CHZ-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,
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(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,
(1,3-dimethylbutoxyamino)methyl,
(2,2-dimethylbutoxyamino)methyl,
(2,3-dimethylbutoxyamino)methyl,
(3,3-dimethylbutoxyamino)methyl, (1-ethylbutoxyamino)methyl,
(2-ethylbutoxyamino)methyl,
(1,1,2-trimethylpropoxyamino)methyl,
(1,2,2-trimethylpropoxyamino)methyl,
(1-ethyl-1-methylpropoxyamino)methyl,
(1-ethyl-2-methylpropoxyamino)methyl, methoxyaminoethyl,
ethoxyaminoethyl, n-propoxyaminoethyl,
(1-methylethoxyamino)ethyl, n-butoxyaminoethyl,
(1-methylpropoxyamino)ethyl, (2-methylpropoxyamino)ethyl,
(1,1-dimethylethoxyamino)ethyl, n-pentoxyaminoethyl,
(1-methylbutoxyamino)ethyl, (2-methylbutoxyamino)ethyl,
(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,
(4-methylpentoxyamino)ethyl, (1,1-dimethylbutoxyamino)ethyl,
(1,2-dimethylbutoxyamino)ethyl,
(1,3-dimethylbutoxyamino)ethyl,
(2,2-dimethylbutoxyamino)ethyl,
(2,3-dimethylbutoxyamino)ethyl,
(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,
(1-ethyl-2-methylpropoxyamino)ethyl, 2-(methoxyamino)propyl,
3-(methoxyamino)propyl or 2-(ethoxyamino)propyl, preferably
C1-C6-alkoxyamino-C1-CZ-alkyl;
- C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl:
C1-C6-alkylamino-C1-C6-alkyl such as CHZ-NH-CH3, CH2-NH-CZHS,
CHy-NH-CHZ-CzHS, CHZ-NH-CH(CH3)z, CHZ-NH-(CHy)3-CH3,
CH2-NH-CH(CH3)-CZHS,
CH2-NH-CH2-CH(CH3)2, CH2-NH-C(CH3)3, CH2-NH-(CHZ)4-CH3,
(1-methylbutylamino)methyl, (2-methylbutylamino)methyl,
(3-methylbutylamino)methyl, (2,2-dimethylpropylamino)methyl,
(1-ethylpropylamino)methyl, n-hexylaminomethyl,
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(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-dimethylbutylamino)methyl,
(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,
(1,1-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-trimethylpropylamino)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-C2-alkyl, which is substituted by
C1-C6-alkoxy as mentioned above, i.e., for example,
CHZ-NH-CH2-OCH3 or CH2-NH-CHZ-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,
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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,
3-methyl-1-pentoxyimino, 4-methyl-1-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, substituted C1-C6-alkyl,
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, CHZ-OCH3,
CH2-OC2H5, n-propoxymethyl, CHZ-OCH(CH3)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,
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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-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl,
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;
- C1-C6-alkoxy-C1-C6-alkoxy: C1-C6-alkoxy which is substituted
by C1-C6-alkoxy as mentioned above, i.e., for example,
OCH2-OCH3, OCHy-OCZHS, n-propoxymethoxy, OCHZ-OCH(CH3)2,
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-(1,1-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-(1,1-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy,
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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
5 OCHy-OCZH5;
- (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, OCH2-CO-CH3, OCH2-CO-C2H5, OCHZ-CO-CH2-CZHS,
10 OCH2-CO-CH(CH3)2, n-butylcarbonylmethoxy, 1-(CO-CH3)ethoxy,
2-(CO-CH3)ethoxy, 2-(CO-CyH5)ethoxy, 2-(CO-CH2-CZHS)ethoxy,
2-(n-butylcarbonyl)ethoxy, 3-(CO-CH3)propoxy, 3-(CO-C2H5)-
propoxy, 3-(CO-CHZ-C2H5)propoxy, 3-(n-butylcarbonyl)propoxy,
4-(CO-CH3)butoxy, 4-(CO-C2H5)butoxy, 4-(CO-CH2-CZHS)butoxy,
15 4-(n-butylcarbonyl)butoxy, 5-(CO-CH3)pentoxy, 5-(CO-C2H5)-
pentoxy, 5-(CO-CHZ-CZHS)pentoxy, 5-(n-butylcarbonyl)butoxy,
6-(CO-CH3)hexoxy, 6-(CO-CzHS)hexoxy, 6-(CO-CHZ-CZHS)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, OCHy-CO-OCH3, OCH2-CO-OC2H5,
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)butoxy,
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 OCH2-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;
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- (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl:
C1-C6-alkylsulfonyl which is substituted by
(C1-C6-alkoxy)carbonyl as mentioned above, i.e., for exmaple,
methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl,
1-(methoxycarbonyl)ethylsulfonyl,
2-(methoxycarbonyl)ethylsulfonyl,
2-(ethoxycarbonyl)ethylsulfonyl,
3-(methoxycarbonyl)propylsulfonyl,
4-(methoxycarbonyl)butylsulfonyl,
5-(methoxycarbonyl)pentylsulfonyl or
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-SCzHS, CH2-SCHZ-CZHS, CHz-SCH(CH3)2,
n-butylthiomethyl, CH2-SCH(CH3)-C2H5, CHZ-SCHZ-CH(CH3)2,
CH2-SC(CH3)3, 2-(SCHg)ethyl, 2-(SC2H5)ethyl,
2-(SCHZ-C2H5)ethyl, 2-[SCH(CH3)Z]ethyl, 2-(n-butylthio)ethyl,
2-[SCH(CH3)-CZHS]ethyl, 2-(2-methylpropylthio)ethyl,
2-[SC(CH3)3]ethyl, 2-(SCH3)propyl, 3-(SCH3)propyl,
2-(SC2H5)propyl, 3-(SCZH5)-propyl, 3-(SCH2-C2H5)propyl,
3-(butylthio)propyl, 4-(SCH3)butyl, 4-(SCZHS)butyl,
4-(SCH2-CZHS)butyl or 4-(n-butylthio)butyl, in particular
2-(SCH3)ethyl;
- C1-C6-alkylthio-C1-C6-alkoxy: C1-C6-alkoxy which is
substituted by C1-C6-alkylthio as mentioned above, i.e., for
example, OCH2-SCH3, OCHz-SC2H5, OCHZ-SCH2-C2H5, OCHZ-SCH(CH3)2.
n-butylthiomethoxy, OCH2-SCH(CH3)-CyH5, OCH2-SCH2-CH(CH3)Z,
OCHy-SC(CH3)3, 2-(SCH3)ethoxy, 2-(SC2H5)ethoxy, 2-(SCHZ-CZH5)-
ethoxy, 2-[SCH(CH3)2]ethoxy, 2-(n-butylthio)ethoxy,
2-[SCH(CH3)-C2H5]ethoxy, 2-(2-methylpropylthio)ethoxy,
2-[SC(CH3)3]ethoxy, 2-(SCH3)propoxy, 3-(SCH3)propoxy,
2-(SC2H5)propoxy, 3-(SCzHs)propoxy, 3-(SCH2-CZHS)propoxy,
3-(butylthio)propoxy, 4-(SCH3)butoxy, 4-(SCZHS)butoxy,
4-(CHZ-C2H5)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,
preferably by SCH3 or SCZHS, 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-CH2-SCH3 or CO-CH(CH3)-SCH3;
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- 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)s12.
N-ethyl-N-methylamino, N-methyl-N-propylamino,
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-(1,1-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
N,N-dimethylamino or N,N-diethylamino, i.e., for example,
OCH2-N(CH3)y, OCH2-N(C2H5)2, OCH(CH3)-N(CH3)2,
2-(dimethylamino)ethoxy, OCH(CH3)-N(C2H5)2,
3-(dimethylamino)propoxy, 4-(dimethylamino)butoxy,
5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in
particular OCH2-N(CH3)2 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,
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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,
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;
- CZ-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-I-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-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,
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,
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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 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;
25
- 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-dimethylprop-2-en-1-ylthio,
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,
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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,
5 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,
10 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,
15 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,
20 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
25 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-1-yn-3-yl,
30 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,
35 n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl,
3-methylpent-1-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;
- C2-C6-alkynyl: ethynyl or one of the radicals mentioned under
C3-C6-alkynyl, in particular ethynyl or prop-2-yn-1-yl;
- C3-C6-alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy,
n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-Q-yloxy,
n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy,
n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy,
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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,
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
particular prop-2-yn-1-yloxy;
- CZ-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-1-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,
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,
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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;
- CZ-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,
1,1-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-methylpent-4-en-1-yloxycarbonyl,
2-methylpent-4-en-1-yloxycarbonyl,
3-methylpent-4-en-1-yloxycarbonyl,
4-methylpent-4-en-1-yloxycarbonyl,
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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-yloxycarbonyl, i.e., for example,
prop-2-en-1-yloxycarbonylmethyl;
- (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-methylbut-2-en-1-ylcarbonyloxy,
2-methylbut-2-en-1-ylcarbonyloxy,
3-methylbut-2-en-1-ylcarbonyloxy,
1-methylbut-3-en-1-ylcarbonyloxy,
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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-1-ylcarbonyloxy,
n-hex-4-en-1-ylcarbonyloxy, n-hex-5-en-1-ylcarbonyloxy,
1-methylpent-1-en-1-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-ylcarbonyloxy,
2-ethylbut-3-en-1-ylcarbonyloxy,
1,1,2-trimethylprop-2-en-1-ylcarbonyloxy,
1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy,
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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;
5 - (C2-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,
10 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,
15 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-methylbut-2-en-1-ylcarbonylthio,
20 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,
25 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,
30 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,
35 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,
40 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-methylpent-4-en-1-ylcarbonylthio,
2-methylpent-4-en-1-ylcarbonylthio,
3-methylpent-4-en-1-ylcarbonylthio,
4-methylpent-4-en-1-ylcarbonylthio,
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1,1-dimethylbut-2-en-1-ylcarbonylthio,
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,
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,
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,
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,
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,
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,
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,
n-hex-1-yn-5-ylcarbonyloxy, n-hex-1-yn-6-ylcarbonyloxy,
n-hex-2-yn-I-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,
3-methylpent-1-yn-3-ylcarbonyloxy,
3-methylpent-1-yn-4-ylcarbonyloxy,
3-methylpent-1-yn-5-ylcarbonyloxy,
4-methylpent-1-yn-1-ylcarbonyloxy,
4-methylpent-2-yn-4-ylcarbonyloxy or
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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-ylsulfonyloxy,
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-1-yn-4-ylcarbonylthio,
3-methylpent-1-yn-5-ylcarbonylthio,
4-methylpent-1-yn-1-ylcarbonylthio,
0050/49498
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43
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-yl;
- 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 by
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-C1-C6-alkyl: C1-C6-alkyl which is substituted
by C3-C6-alkynyloxy as mentioned above, preferably by
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)hexoxy, 6-(cyclobutyl)hexoxy,
6-(cyclopentyl)hexoxy or 6-(cyclohexyl)hexoxy, in particular
cyclopentylmethoxy or cyclohexylmethoxy;
- C3-C6-cycloalkyloxy: cyclopropyloxy, cyclobutyloxy,
cyclopentyloxy or cyclohexyloxy;
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- C3-C6-cycloalkylthio: cyclopropylthio, cyclobutylthio,
cyclopentylthio or cyclohexylthio;
- C3-C6-CyC10a1kylCarbOnylOXy: cyclopropylcarbonyloxy,
cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or
cyclohexylcarbonyloxy;
- C3-C6-cycloalkylsulfonyloxy: cyclopropylsulfonyloxy,
cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or
cyclohexylsulfonyloxy;
- CS-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 contain an oxygen or sulfur atom as ring
member 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 hetercyclyl - which may be attached directly or
via an oxygen, alkoxy, alkenyloxy or alkynyloxy bridge - is to be
understood as including both saturated, partially or fully
unsaturated and aromatic heterocycles having one to three
heteroatoms selected from a group consisting of
- one to three nitrogen atoms,
- one or two oxygen and
- one or two sulfur atoms.
Examples of saturated heterocycles which may 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,
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,
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tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl,
tetrahydropyrazol-4-yl, tetrahydropyran-2-yl,
tetrahydropyran-3-yl, tetrahydropyran-4-yl,
tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,
5 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-yl, 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,
10 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,
15 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,
20 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.
30
Examples of unsaturated heterocycles which may 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;
Among the heteroaromatics, preference is given to 5- and
6-membered heteroaromatics, i.e., for example,
furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and
3-thienyl, pyrrolyl 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, oxadiazolyl such as
1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl 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 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,
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furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and
1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and
thienyl.
In view of the use of the 1-aryl-4-thiouracils of the formula I
according to the invention as herbicides, the variables
preferably have the following meanings, in each case on their own
or in combination:
X is oxygen
R1 is hydrogen, amino or methyl, in particular methyl;
R2 is hydrogen, halogen or methyl;
20
R3 is hydrogen, halogen or methyl, in particular
a) hydrogen or halogen, particularly preferably hydrogen;
b) hydrogen or methyl, particularly preferably methyl;
c) halogen or methyl, particularly preferably halogen;
R4 is fluorine;
R5 is cyano or halogen, in particular
a) cyano;
b) chlorine;
Y is the methine group or together with R6 is a bridge
>C-0-C(R1~)=N-, in particular
a) the methine group;
b) together with R6 a bridge >C-O-C(R1~)=N-;
R6 on the one hand together with RS is a radical
-N(R~)-CO-C(R8~,R9~)-0- linked to RS via the oxygen;
R6 on the other hand
1) is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen,
C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy,
C1-C6-haloalkylthio, C1-C6-alkylthio(C1-C6-alkyl)carbony-1,
(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,
2) is C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy,
C3-C6-cycloalkylthio, CZ-C6-alkenyloxy, C2-C6-alkenylthio,
CZ-C6-alkynyloxy, C2-C6-alkynylthio,
(C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio,
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(Ci-C6-alkoxy)carboxyloxy, (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 to three substituents, in each case
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-alkylsulfynyl,
Ci-C6-alkylsulfonyl, Ci-C6-alkylideneaminoxy, oxo,
=N-ORi 1.
- the phenyl, phenoxy or phenylsulfonyl group which may
be unsubstituted or may carry one to 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_R12. _CO_OR12, -CO-SR12, -CO-N(R12)-R13. _OCO-R12,
-OCO-OR12, -OCO-SR12, -OCO-N(R12)-R13. _N(Riz)_R13 and
_C ( Ri4 ) =N_OR11;
3} is -CZ2-R15. _C(NR16)_R15. _C(R15)(Z3Ri7)(Z4R18).
_C ( R15 ) =C ( R19 ) _CjQ. -C ( R15 ) =C ( R19 ) _CO_R2 0 .
-CH(Ri5)-CH(Ri9)-CO-R2o, -C(R15)=C(Ri9)_CH2_CO_R2o.
_C(R15)=C(R19)_C(R21)=C(R22)_CO_R20.
_C(R15)-C(R19)_CH2_CH(R23)_CO_R2o. _Cp_OR24, -CO-SRz4,
-CO-N ( R24 ) -ORi i , -C = C-CO-NH-ORi i , -C = C-CO-N ( R2 4 ) -ORi i ,
-C=C-CS-NH-ORii, -C=C-CS-N(R24)-ORii.
_C ( R15 ) =C ( R19 ) _CO_NH-ORi i , -C ( Ri5 ) -C ( Ri9 ) _CO_N ( R2a ) _ORll
.
_C(R15)=C(R19)_CS_NH-ORii, -C(Ri5)=C(R19)_CS-N(R24)_OR11.
_C(R15)=C(R19)_C(R14)=N_pRll. _C(R14)=N_pRll.
_C=C_C (R14 )=N_OR11. _C ( Z3R17 ) ( Z4R18 ) _OR24.
_C ( 23817 ) ( Z4R18 ) _gR24. _C ( Z3R17 ) ( Z4R18 ) _r7 ( 825 ) 826.
_N ( 825 ) _826 or _CO-N ( 825 ) -826 ;
R6, in particular,
2) is Ci-C6-alkoxy, Cz-C6-alkenyloxy or Cz-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-Riz, -CO-OR12, -CO-N(R12)R13.
-N(R12)_R13 and C(R14)=N-ORii;
3) is -CO-RiS, -C(NRi6)-Ris. _C(R15)(OR17)(pRlB).
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_C(R15)-C(R19)_Cp_R2o~ _CH(R15)_Cg(R19)_Cp_R20~ _CO_OR24,
_CO_N(R24)_pRll~ _C(Ri5)=C(R19)_CO_N(R24)-ORii,
_C ( R14 ) =N_pRl l ~ _C ( pRi7 ) ( QR18 ) _pR24 ~ _N ( R25 ) R26 pr
-CON ( R25 ) R2 6 ;
Re, R9, R8', R9' are each hydrogen.
15
25
35
45
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Very particular preference is given to the 1-aryl-4-thiouracils
of the formula Ia (-~- I where X = oxygen, R2 = hydrogen, R3 =
hydrogen and Y = the methine group)
R \ O R6
N--~
S~N ~ ~ R5 Ia,
R4
in particular to the compounds Ia.l to Ia.160 listed in Table 1
below:
Table 1
No. R R R ~ R
Ia.l CH3 F CN OCH(CH3)-CO-OCH3
Ia.2 CH3 F CN OCHZ-C=CH
Ia.3 CH3 F CN OCH(CH3)-C = CH
Ia.4 CH3 F CN OCH(CH3)-CO-OCHZ-CHZ-OCH3
Ia.5 CH3 F CN CO-OCH3
Ia.6 CH3 F CN CO-OCH(CH3)-CO-OCH3
Ia.7 CH3 F CN CO-OC(CH3)2-CO-OCH3
Ia.8 CH3 F CN CO-OCH(CHg)-CO-OCHy-CH=CHz
Ia.9 CH3 F CN CO-OC(CH3)2-CO-OCHZ-CH=CHz
Ia.lO CH3 F CN C(N-OCH3)-OCHZ-CO-OCH3
Ia.ll CH3 F CN C(N-OCH3)-OCH(CHg)-CO-OCH3
Ia.l2 CH3 F CN C(N-OCHg)-OCHy-CO-O(phenyl)
Ia.l3 CH3 F CN CH=C(C1)-CO-OCH3
Ia.l4 CH3 F CN CH=C(CH3)-CO-OCH3
Ia.l5 CH3 F CN CH=C(C1)-C(N-OCH3)-OCH2-CO-OCHg
Ia.l6 CH3 F CN CH=N-OCH3
Ia.l7 CH3 F CN CH=N-OCZHS
Ia.l8 CH3 F CN CHz-N(CHg)-OCH3
Ia.l9 CH3 F CN NH-SOZ-CH3
Ia.20 CH3 F CN NH-SOZ-CZHS
Ia.21 CH3 F C1 OCH(CH3)-CO-OCH3
Ia.22 CH3 F C1 OCHZ-C = CH
Ia.23 CH3 F C1 OCH(CH3)-C = CH
Ia.24 CH3 F C1 OCH(CH3)-CO-OCHZ-CHZ-OCH3
Ia.25 CH3 F C1 CO-OCH3
Ia.26 CH3 F C1 CO-OCH(CH3)-CO-OCH3
Ia.27 CH3 F C1 CO-OC(CH3)Z-CO-OCH3
Ia.28 CH3 F C1 CO-OCH(CH3)-CO-OCH2-CH=CHZ
Ia.29 CH3 F C1 CO-OC(CH3)2-CO-OCH2-CH=CHz
Ia.30 CH3 F C1 C(N-OCH3)-OCHZ-CO-OCH3
Ia.31 CH3 F C1 C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.32 CH3 F C1 C(N-OCH3)-OCHZ-CO-O(phenyl)
Ia.33 CH3 F Cl CH=C(C1)-CO-OCH3
Ia.34 CH3 F C1 CH=C(CH3)-CO-OCH3
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No. R R R R
Ia.35 CH3 F C1 CH=C(C1)-C(N-OCH3)-OCH2-CO-OCH3
Ia.36 CH3 F C1 CH=N-OCH3
Ia.37 CH3 F C1 CH=N-OCZH5
5 Ia.38 CH3 F C1 CHz-N(CH3)-OCH3
Ia.39 CH3 F Cl NH-SOZ-CH3
Ia.40 CH3 F C1 NH-SOZ-C2H5
Ia.41 CH3 H CN OCH(CHg)-CO-OCH3
Ia.42 CH3 H CN OCH2-C = CH
Ia.43 CH3 H CN OCH(CH3)-C = CH
10 Ia.44 CH3 H CN OCH(CH3)-CO-OCH2-CHZ-OCH3
Ia.45 CH3 H CN CO-OCH3
Ia.46 CH3 H CN CO-OCH(CH3)-CO-OCH3
Ia.47 CH3 H CN CO-OC(CH3)Z-CO-OCH3
Ia.48 CH3 H CN CO-OCH(CH3)-CO-OCHZ-CH=CH2
15 Ia.49 CH3 H CN CO-OC(CH3)2-CO-OCHZ-CH=CH2
Ia.50 CH3 H CN C(N-OCH3)-OCH2-CO-OCH3
Ia.51 CH3 H CN C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.52 CH3 H CN C(N-OCH3)-OCH2-CO-O(phenyl)
Ia.53 CH3 H CN CH=C(Cl)-CO-OCH3
Ia.54 CH3 H CN CH=C(CH3)-CO-OCH3
20 Ia.55 CH3 H CN CH=C(C1)-C(N-OCH3)-OCHz-CO-OCH3
Ia.56 CH3 H CN CH=N-OCH3
Ia.57 CH3 H CN CH=N-OCZHS
Ia.58 CHg H CN CHZ-N(CH3)-OCH3
Ia.59 CH3 H CN NH-SOZ-CH3
25 Ia60 CH3 H CN NH-S02-C2H5
Ia.61 CH3 H C1 OCH(CH3)-CO-OCH3
Ia.62 CH3 H C1 OCHZ-C = CH
Ia.63 CH3 H C1 OCH(CH3)-C = CH
Ia.64 CH3 H C1 OCH(CH3)-CO-OCH2-CH2-OCH3
Ia.65 CH3 H C1 CO-OCH3
30 Ia.66 CH3 H C1 CO-OCH(CH3)-CO-OCH3
Ia.67 CH3 H Cl CO-OC(CH3)2-CO-OCH3
Ia.68 CH3 H C1 CO-OCH(CH3)-CO-OCHZ-CH=CHZ
Ia.69 CH3 H C1 CO-OC(CH3)2-CO-OCHZ-CH=CHZ
Ia.70 CH3 H C1 C(N-OCH3)-OCHy-CO-OCH3
35 Ia.71 CH3 H C1 C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.72 CH3 H C1 C(N-OCH3)-OCH2-CO-O(phenyl)
Ia.73 CH3 H C1 CH=C(C1)-CO-OCH3
Ia.74 CH3 H C1 CH=C(CH3)-CO-OCH3
Ia.75 CH3 H C1 CH=C(Cl)-C(N-OCH3)-OCHy-CO-OCH3
Ia.76 CH3 H C1 CH=N-OCH3
40 Ia.77 CH3 H C1 CH=N-OCzHS
Ia.78 CH3 H C1 CHz-N(CH3)-OCH3
Ia.79 CH3 H C1 NH-SOZ-CH3
Ia.80 CH3 H C1 NH-S02-CyH5
Ia.81 NH2 F CN OCH(CH3)-CO-OCH3
45 Ia.82 NH2 F CN OCHZ-C = CH
Ia.83 NHZ F CN OCH(CH3)-C = CH
Ia.84 NHZ F CN OCH(CH3)-CO-OCH2-CHZ-OCH3
-...
Ia.85 NHZ F CN CO-OCH3
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No. R R R R
Ia.86 NH2 F CN CO-OCH(CH3)-CO-OCH3
Ia.87 NHZ F CN CO-OC(CH3)y-CO-OCH3
Ia.88 NH2 F CN CO-OCH(CH3)-CO-OCHy-CH=CHy
Ia.89 NH2 F CN CO-OC(CH3)2-CO-OCHZ-CH=CHZ
Ia.90 NH2 F CN C(N-OCH3)-OCH2-CO-OCH3
Ia.91 NH2 F CN C(N-OCH3}-OCH(CH3)-CO-OCH3
Ia.92 NHZ F CN C(N-OCH3}-OCHZ-CO-0(phenyl)
Ia.93 NH2 F CN CH=C(C1)-CO-OCH3
Ia.94 NH2 F CN CH=C(CH3)-CO-OCH3
Ia.95 NH2 F CN CH=C(C1)-C(N-OCH3)-OCHZ-CO-OCH3
Ia.96 NHZ F CN CH=N-OCH3
Ia.97 NHZ F CN CH=N-OCZHS
Ia.98 NHZ F CN CHZ-N(CH3)-OCH3
Ia.99 NHZ F CN NH-S02-CH3
Ia.100 NHy F CN NH-S02-CZHS
Ia.101 NHy F C1 OCH(CH3}-CO-OCH3
Ia.102 NHZ F C1 OCHZ-C = CH
Ia.103 NHZ F C1 OCH(CH3)-C = CH
Ia.104 NH2 F C1 OCH(CH3)-CO-OCH2-CHZ-OCH3
Ia.105 NHy F C1 CO-OCH3
Ia.106 NH2 F C1 CO-OCH(CH3)-CO-OCH3
Ia.107 NHZ F C1 CO-OC(CH3)y-CO-OCH3
Ia.108 NHy F C1 CO-OCH(CH3)-CO-OCHZ-CH=CH2
Ia.109 NH2 F C1 CO-OC(CH3)2-CO-OCH2-CH=CH2
Ia.110 NH2 F Cl C(N-OCH3)-OCHZ-CO-OCH3
Ia.lll NHZ F C1 C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.112 NHZ F C1 C(N-OCH3)-OCHZ-CO-O(phenyl)
Ia.113 NHZ F C1 CH=C(C1)-CO-OCH3
Ia.114 NHz F C1 CH=C(CH3)-CO-OCH3
Ia.115 NHz F C1 CH=C(C1)-C(N-OCH3)-OCHZ-CO-OCH3
Ia.116 NHz F C1 CH=N-OCH3
Ia,117 NHZ F C1 CH=N-OCzHS
- _.
Ia . NHZ F Cl CH2-N ( CH3 ) -OCH3
118
Ia.119 NHZ F C1 NH-S02-CH3
Ia.120 NHZ F C1 NH-S02-CzHg
Ia.121 NHy H CN OCH(CH3)-CO-OCH3
Ia.122 NHZ H CN OCHZ-C = CH
Ia.123 NHZ H CN OCH(CH3)-C = CH
Ia.124 NHz H CN OCH(CH3)-CO-OCH2-CH2-OCH3
Ia.125 NH2 H CN CO-OCH3
Ia.126 NHZ H CN CO-OCH(CH3)-CO-OCH3
Ia.127 NH2 H CN CO-OC(CH3)2-CO-OCH3
Ia.128 NHz H CN CO-OCH(CH3)-CO-OCH2-CH=CHZ
Ia.129 NH2 H CN CO-OC(CH3)Z-CO-OCH2-CH=CHZ
Ia.130 NHy H CN C(N-OCH3)-OCH2-CO-OCH3
Ia.131 NHZ H CN C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.132 NH2 H CN C(N-OCH3)-OCHZ-CO-O(phenyl)
Ia.133 NHZ H CN CH=C(C1)-CO-OCH3
Ia.134 NH2 H CN CH=C(CH3)-CO-OCH3
Ia.135 NHZ H CN CH=C(C1)-C(N-OCH3)-OCHZ-CO-OCH3
Ia.136 NH2 H CN CH=N-OCH3
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52
No. R Ry R R
Ia.137 NHZ H CN CH=N-OCZHS
Ia.138 NHZ H CN CHZ-N(CHg)-OCH3
Ia.139 NH2 H CN NH-S02-CHg
Ia.140 NHy H CN NH-SOZ-CzHS
Ia.141 NH2 H C1 OCH(CH3)-CO-OCH3
Ia.142 NHZ H C1 OCHZ-C = CH
Ia.143 NHZ H C1 OCH(CH3)-C = CH
Ia.144 NHz H C1 OCH(CH3)-CO-OCH2-CH2-OCH3
Ia.145 NHZ H C1 CO-OCH3
10Ia.146 NH2 H C1 CO-OCH(CH3)-CO-OCH3
Ia.147 NHZ H C1 CO-OC(CH3)2-CO-OCH3
Ia.148 NHZ H C1 CO-OCH(CH3)-CO-OCHZ-CH=CH2
Ia.149 NHZ H C1 CO-OC(CH3)Z-CO-OCH2-CH=CH2
Ia.150 NHZ H C1 C(N-OCH3)-OCH2-CO-OCH3
15Ia151 NH2 H C1 C(N-OCH3)-OCH(CH3)-CO-OCH3
Ia.152 NHZ H C1 C(N-OCH3)-OCHZ-CO-0(phenyl)
Ia.153 NHy H C1 CH=C(C1)-CO-OCH3
Ia.154 NHz H C1 CH=C(CH3)-CO-OCH3
Ia.155 NH2 H C1 CH=C(C1)-C(N-OCH3)-OCH2-CO-OCH3
Ia.156 NH2 H C1 CH=N-OCH3
20Ia.157 NHy H C1 CH=N-OCZHS
Ia.158 NHz H C1 CHy-N(CH3)-OCH3
Ia.159 NHZ H C1 NH-S02-CH3
Ia.160 NHZ H C1 NH-SOz-C2H5
25 Furthermore, particular preference is given to the
1-aryl-4-thiouracils of the formulae Ib to Iq, in particular to
- the compounds Ib.l to Ib.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R2 is
30 fluorine:
R1 O R6
S N N ~ ~ RS
Ib
35 F R4
- the compounds Ic.l to Ic.160 which differ from the
40 corresponding compounds Ia.l to Ia.160 only in that RZ is
chlorine:
0050/49498
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53
R1 ~O Rs
N
S N ~ ~ R5 Ic
Cl R4
- the compounds Id.l to Id.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R3 is
methyl:
R1\ , 0 R6
'~'/~/N
S N ~ ~ R5 Id
H3C R4
- the compounds Ie.l to Ie.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that RZ is
fluorine and R3 is methyl:
R1 O Rs
S N ~ ~ R5 Ie
F H3C R4 i
- the compounds If.l to If.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that Rz is
chlorine and R3 is methyl:
Ri\ O Rs
N
S N / \ R5 If
C1 H3C R4
the compounds Ig.l to Ig.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R3 is
trifluoromethyl:
R1 O Rs
S N N / \ R5 Ig
F3C R4
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54
- the compounds Ih.l to Ih.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that Rz is
fluorine and R3 is trifluoromethyl:
R1 0 R6
\N~
S N / \ R5 Ih
F F3C R4
- the compounds Ii.l to Ii.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that RZ is
chlorine and R3 is trifluoromethyl:
R1 O R6
S N ~ ~ R5 Ii
C1 F3C R4
- the compounds Ik.l to Ik.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R3 is
fluorine:
R1\ O R6
N
S N ~ \ R5 Ik
F R4
- the compounds Im.l to Im.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that Rz and R3
are each fluorine:
R1\ ~ R6
N
S N ~ \ R5 Im
F F R4
- the compounds In.l to In.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that RZ is
chlorine and R3 is fluorine:
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R \ O R6
N-
S N ~ ~ RS In
5 C1 F R4
- the compounds Io.l to Io.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R3 is
10 chlorine:
R1\ ~O Rs
N
S N ~ \ R5 Io
C1 R4
- the compounds Ip.l to Ip.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that R2 is
fluorine and R3 is chlorine:
R \ ~ R6
N
S N / \ R5 Ip
C 1 R4
- the compounds Iq.l to Iq.160 which differ from the
corresponding compounds Ia.l to Ia.160 only in that Rz and R3
are each chlorine:
R1\ ~ Rs
N
S N ~ \ R5 Iq
C1 C1R4
Moreover, particular preference is given to the
1-aryl-4-thiouracils of the formula Ir ~~-- I where X = oxygen; Y =
methylene; R5+R6 = -N(R~)-CO-CH2-O-}
' 0050/49498
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56
R~ O
R~ O \N
N~ Ir,
S N ~ ~ O
R2 R3 R4
in particular to the compounds Ir.l to Ir.96 listed in Table 2
below:
Table 2
No. R R R R R
Ir . CH3 H H H CHZ-C = CH
1
Ir.2 CH3 H H H CH(CH3)-C = CH
Ir.3 CH3 H H H OCyHs
Ir.4 CH3 H H H OCH(CH3)z
Ir . CHg H H F CHZ-C = CH
5
Ir.6 CH3 H H F CH(CH3)-C = CH
Ir.7 CH3 H H F OCyHs
Ir.B CH3 H H F OCH(CHg)z
Ir . NHZ H H H CHz-C = CH
9
Ir.lO NHZ H H H CH(CH3)-C = CH
Ir.ll NHZ H H H OCzHs
Ir.l2 NHZ H H H OCH(CH3)z
Ir .13 NHZ H H F CHz-C = CH
Ir.l4 NHZ H H F CH(CH3)-C=CH
Ir.lS NHz H H F OCZHs
Ir.l6 NHZ H H F OCH(CH3)z
Ir.l7 CH3 CH3 H H CHz-C = CH
Ir.l8 CH3 CH3 H H CH(CH3)-C = CH
Ir.l9 CH3 CH3 H H OCZHS
Ir.20 CH3 CH3 H H OCH(CH3)2
Ir.21 CH3 CH3 H F CHz-C = CH
Ir.22 CH3 CH3 H F CH(CH3)-C = CH
Ir.23 CH3 CH3 H F OCZHs
Ir.24 CH3 CH3 H F OCH(CH3)z
Ir.25 NHz CH3 H H CHZ-C = CH
Ir.26 NHZ CH3 H H CH(CH3)-C = CH
Ir.27 NHZ CH3 H H OCyHs
Ir.28 NHz CH3 H H OCH(CH3)z
Ir.29 NHZ CH3 H F CHZ-C=CH
Ir.30 NHz CH3 H F CH(CH3)-C = CH
Ir.31 NHz -~H3. . H F OCzHS
Ir . NHz CH3 H F -NCH ( CHg ) Z -..
32
Ir.33 CH3 H CH3 H CHz-C=CH
Ir.34 CH3 H CH3 H CH(CH3)-C = CH
Ir.35 CH3 H CH3 H OCZHs
Ir.36 CH3 H CH3 H OCH(CH3)z
Ir . CH3 H CH3 F CHZ-C = CH
37
Ir.38 CH3 H CH3 F CH(CH3)-C = CH
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57
No. R R R R R
Ir.39 CH3 H CH3 F OCZHS
Ir.40 CH3 H CH3 F OCH(CH3)z
Ir.41 NHZ H CH3 H CHZ-C = CH
Ir.42 NHZ H CH3 H CH(CH3)-C=CH
Ir.43 NHZ H CH3 H OC2H5
Ir.44 NHz H CH3 H OCH(CH3)2
Ir.45 NHy H CH3 F CHZ-C = CH
Ir.46 NHZ H CH3 F CH(CH3)-C=CH
Ir.47 NH2 H CH3 F OCZH5
Ir.48 NHy H CH3 F OCH(CH3)2
Ir.49 CH3 CH3 CH3 H CH2-C = CH
Ir.50 CH3 CH3 CH3 H CH(CH3)-C = CH
Ir.51 CH3 CH3 CH3 H OCZHS
Ir.52 CH3 CH3 CH3 H OCH(CH3)2
Ir.53 CH3 CH3 CH3 F CHy-C = CH
Ir . CH3 CH3 CH3 F CH ( CH3 ) -C =CH
54
Ir.55 CH3 CH3 CH3 F OCyHS
Ir.56 CH3 CHg CH3 F OCH(CH3)2
Ir.57 NH2 CH3 CH3 H CH2-C=CH
Ir.58 NHZ CH3 CH3 H CH(CHg)-C = CH
Ir.59 NHy CH3 CH3 H OCZHS
Ir.60 NHz CH3 CH3 H OCH(CH3)2
Ir.61 NHp CH3 CH3 F CH2-C = CH
Ir.62 NHZ CH3 CH3 F CH(CH3)-C = CH
Ir.63 NHy CH3 CH3 F OCZH5
Ir.64 NHZ CH3 CH3 F OCH(CH3)2
Ir.65 CH3 H C1 H CH2-C=CH
Ir.66 CH3 H C1 H CH(CH3)-C = CH
Ir.67 CH3 H C1 H OCZHS
Ir.68 CH3 H C1 H OCH(CH3)2
Ir.69 CH3 H C1 F CHy-C=CH
Ir.70 CH3 H C1 F CH(CH3)-C = CH
Ir.71 CH3 H C1 F OC2H5
Ir.72 CH3 H C1 F OCH(CH3)2
Ir.73 NHy H C1 H CHz-C=CH
Ir.74 NHZ H C1 H CH(CHg)-C = CH
Ir.75 NHz H C1 H OC2H5
Ir.76 NH2 H C1 H OCH(CH3)2
Ir.77 NHZ H C1 F CH2-C=CH
Ir.78 NHZ H C1 F CH(CH3)-C = CH
Ir.79 NHy H C1 F OC2H5
Ir.80 NHZ H C1 F OCH(CH3)2
Ir.81 CH3 CH3 C1 H CH2-C=CH
Ir.82 CH3 CH3 C1 H CH(CH3)-C = CH
Ir.83 CH3 CHg C1 H OCzHS
Ir.84 CH3 CH3 C1 H OCH(CH3)2
Ir.85 CH3 CH3 C1 F CH2-C = CH
Ir.86 CH3 CH3 C1 F CH(CH3)-C = CH
Ir.87 CH3 CH3 C1 F OCZHS
Ir.88 CH3 CH3 C1 F OCH(CH3)2
Ir.89 NHz CH3 C1 H CHZ-C = CH
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58
No. R R R R R
Ir.90 NHy CHg C1 H CH(CH3)-C = CH
Ir.91 NHz CH3 C1 H OC2H5
Ir.92 NH2 CHg C1 H OCH(CH3)2
Ir.93 NHz CH3 C1 F CHZ-C=CH
Ir.94 NHZ CH3 C1 F CH(CH3)-C = CH
Ir.95 NHy CH3 C1 F OC2H5
Ir.96 NH2 CH3 C1 F OCH(CH3)z
The 1-aryl-4-thiouracils of the formula I can be obtained in
various ways, in particular by one of the following processes:
A~ Sulfurization of a 1-aryluracil of the formula II:
R1 X R6 R1 X R6
N~~ Y sulfurization N~~ Y 5
p- N ~ ~ R5 S- N ~ ~ R
R2 R3 R4 R2 R3 R4
II I
The sulfurization is generally carried out in an inert
solvent or diluent, for example in an aromatic hydrocarbon,
such as toluene and the xylenes, in an ether, such as diethyl
ether, 1,2-dimethoxyethane and tetrahydrofuran, or in an
organic amine, such as pyridine.
Particularly suitable sulfurizing agents are phosphorus(V)
sulfide and
2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-
2,4-dithione ("Lawesson's Reagent").
1- to 5-times the molar amount, based on the starting
material to be sulfurized, is usually sufficient for
substantially complete conversion.
The reaction temperature is normally from 20 to 200~C,
preferably from 40~C to the boiling point of the reaction
mixture.
The precursors II are known from WO 97/05117 or they can be
prepared in a manner similar to one of the processes
described therein.
CA 02349386 2001-04-30
0050/49498
59
B~ Reaction of a 4-thiouracil of the formula III with a
fluoroaromatic of the formula IV:
R1 X R6
N ~~ Y
S- N-H ~' g \ / R5 ~ I
R2 R3 R4
III IV
The reaction succeeds particularly well if IV carries an
electron-withdrawing group in the ortho- or para-position to
the fluorine atom.
Instead of IV, it is also possible to employ a fluoroaromatic
which can be converted into IV.
Reaction of a compound Va, Vb or Vc with an aryl amine of the
formula VI:
R1 O R6
N " OL1 Y
S + H2N ~ ~ R5 --~. I
OL2
R2 R3 R4
Va VI
O
R\
N~ OL1
S OL 2 + V I -fir. I
OL3
R2 R3
Vb
1 O
R
N" "OL1
S + VI -~ I
p
R2 R3
Vc
0050/49498
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L1, L2, L3 are each customary protective groups for hydroxyl,
such as methyl, ethyl, methylsulfonyl, benzyl and
trimethylsilyl.
5 The processes (B~) and (C~) according to the invention for
preparing compounds of the formula (I) are preferably carried out
in the presence of a suitable reaction auxiliary.
Suitable reaction auxiliaries are, in general, the customary
10 inorganic or organic bases or acid acceptors. These preferably
include alkali metal or alkaline earth metal acetates, amides,
carbonates, bicarbonates, hydrides, hydroxides or alkoxides, for
example sodium acetate, potassium acetate or calcium acetate,
lithium amide, sodium amide, potassium amide or calcium amide,
15 sodium carbonate, potassium carbonate or calcium carbonate,
sodium bicarbonate, potassium bicarbonate or calcium bicarbonate,
lithium hydride, sodium hydride, potassium hydride or calcium
hydride, lithium hydroxide sodium hydroxide, potassium hydroxide
or calcium hydroxide, sodium methoxide, ethoxide, n- or
20 iso-propoxide, n-, iso-, sec- or tert-butoxide or potassium
methoxide, ethoxide, n- or iso-propoxide, n-, iso-, sec- or
tert-butoxide;
furthermore also basic organic nitrogen compounds, for example
trimethylamine, triethylamine, tripropylamine, tributylamine,
25 ethyldiisopropylamine, N,N-dimethylcyclohexylamine,
dicyclohexylamine, ethyldicyclohexylamine, N,N-dimethylaniline,
N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-,
4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl and
3,5-dimethylpyridine, 5-ethyl-2-methylpyridine,
30 4-dimethylaminopyridine, N-methylpiperidine,
1,4-diazabicyclo[2.2.2]octane (DABCO),
1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
35 The processes (B~) and (C~) for preparing the compounds of the
formula (I) are preferably carried out in the presence of a
diluent. Suitable diluents are, in general, the customary organic
solvents. These preferably include aliphatic, alicyclic and
aromatic, unhalogenated or halogenated hydrocarbons, for example
40 pentane, hexane, heptane, petroleum ether, ligroin, benzine,
benzene, toluene, xylene, chlorobenzene, dichlorobenzene,
cyclohexane, methylcyclohexane, dichloromethane (methylene
chloride), trichloromethane (chloroform) or carbon tetrachloride,
dialkyl ethers, such as diethyl ether, diisopropyl ether, methyl
45 tert-butyl ether (MTBE), ethyl tert-butyl ether, methyl
tert-pentyl ether (TAME), ethyl tert-pentyl ether,
tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl
0050/49498
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61
ether, ethylene glycol diethyl ether, diethylene glycol dimethyl
ether and diethylene glycol diethyl ether; dialkyl ketones, such
as acetone, butanone (methyl ethyl ketone), methyl isopropyl
ketone and methyl isobutyl ketone; nitriles, such as
acetonitrile, propionitrile, butyronitrile and benzonitrile;
amides, such as N,N-dimethylformamide (DMF), N,N-dimethyl
acetamide, N-methylformanilide, N-methylpyrrolidone and
hexamethylphosphoric triamide; esters, such as methyl acetate,
ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl
acetate, isobutyl acetate and sec-butyl acetate; sulfoxides, such
as dimethyl sulfoxide; alkanols such as methanol, ethanol,
n-propanol, isopropanol, n-, iso-, sec- and tert-butanol; glycol
ethers, such as ethylene glycol monomethyl ether, ethylene glycol
monoethyl ether, diethylene glycol monomethyl ethyl and
diethylene glycol monoethyl ether; mixtures thereof with water or
pure water.
When carrying out the processes (B~) and (C~), the reaction
temperatures can be varied within a relatively wide range. In
general, the reaction is carried out at from 0 to 200~C,
preferably from 10 to 150~C, in particular from 20~C to the
boiling point of the reaction mixture in question.
For carrying out the processes (A~), (B~) and (C~), the starting
materials are generally employed in approximately equimolar
amounts. However, it is also possible to employ a relatively
large excess of in each case one of the components, up to about
two times the molar amount of the other component. In the process
(A~, for example, it is expedient to employ an excess of
sulfurizing agent.
The processes (A~), (B~) and (C~) are advantageously carried out
at atmospheric pressure or under the autogeneous pressure of the
reaction mixture in question. However, it is also possible to
carry out the processes under elevated or reduced pressure - in
general at from 0.1 to 10 bar.
Work-up of the reaction mixtures in question is generally carried
out by methods known per se, for example by diluting the reaction
solution with water and subsequently isolating 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.
0050/49498
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62
In general, the 1-aryl-4-thiouracils I can be prepared by one of
the synthesis processes mentioned above. For economical or
technical reasons, however, it may be more advantageous to
prepare some of the compounds I from similar 1-aryl-4-thiouracils
- which, however, differ in particular in the meaning of the
radicals R5 and/or R6 -, in a manner known per se, for example by
ester hydrolysis, esterification, amidation, acetalization,
acetal hydrolysis, condensation reaction, Wittig reaction,
Peterson olefiniation, etherification, alkylation, oxidation or
reduction.
In the preparation, the 1-aryl-4-thiouracils I may be obtained as
isomer mixtures. However, these mixtures can, if desired, be
separated into pure isomers using the customary methods for this
purpose, such as crystallization or chromatography, including
chromatography over an optically active adsorbate. Pure optically
active isomers can be prepared advantageously from appropriate
optically active starting materials.
Agriculturally useful salts of the compounds I can be formed by
reaction with a base of the appropriate cation, preferably an
alkali metal hydroxide or hydride, or by reaction with an acid of
the appropriate anion, preferably hydrochloric acid, hydrobromic
acid, sulfuric acid, phosphoric acid or nitric acid.
Salts of I where the metal ion is not an alkali metal ion can be
prepared by cation exchange of the corresponding alkali metal
salt in a conventional manner, similarly ammonium, phosphonium,
sulfonium and sulfoxonium salts by means of ammonia, phosphonium,
sulfonium or sulfoxonium hydroxides.
The compounds I 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 I control vegetation on non-crop areas very
efficiently, especially at high rates of application. They act
against broad-leaved weeds and grass weeds 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 in question, the compounds I,
or herbicidal compositions comprising them, can additionally be
employed in a further number of crop plants for eliminating
undesirable plants. Examples of suitable crops are the following:
0050/49498
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63
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus
officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec.
rapa, Brassica napus var. napus, Brassica napus var.
napobrassica, Brassica rapa var. 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 vitifolium),
Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus
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,
I5 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 I may also be used in crops which
tolerate the action of herbicides owing to breeding, including
genetic engineering methods.
The compounds I, or the 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, spreading or watering. The use
forms depend on the intended purpose; in any case, they should
guarantee the finest possible distribution of the active
compounds according to the invention.
Suitable for use as inert auxiliaries are essentially the
following: 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, for example paraffins,
tetrahydronaphthalene, alkylated naphthalenes and their
derivatives, alkylated benzenes and their derivatives, alcohols
such as methanol, ethanol, propanol, butanol and cyclohexanol,
ketones such as cyclohexanone, strongly polar solvents, for
example amines such as N-methylpyrrolidone, and water.
0050/49498
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64
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 1-aryl-4-thiouracils I, 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 compound, 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, lignin-sulfite waste liquors or methylcellulose.
Powders, materials for broadcasting and dusts can be prepared by
mixing or grinding the active compounds 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 and magnesium oxide, ground
synthetic materials, fertilizers such as ammonium sulfate,
ammonium phosphate, ammonium nitrate and 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 of the active compounds I in the ready-to-use
preparations can be varied within wide ranges. In general, the
formulations comprise approximately from 0.001 to 98~ by weight,
preferably 0.01 to 95~ by weight of at least one active compound.
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The active compounds are employed in a purity of from 90% to
100%, preferably 95% to 100% (according to NMR spectrum).
The following formulation examples illustrate the preparation of
5 such formulations:
I. 20 parts by weight of the compound No. Ib.3 are dissolved
in a mixture composed of 80 parts by weight of alkylated
benzene, 10 parts by weight of the adduct of from 8 to 10
10 mol of ethylene oxide to 1 mol of oleic acid
N-monoethanolamide, 5 parts by weight of 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
15 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 No. Ib.3 are dissolved
20 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
25 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 active compound No. Ib.3 are
30 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
35 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 active compound No. Ib.3 are
40 mixed thoroughly with 3 parts by weight of the sodium salt
of diisobutylnaphthalene-a-sulfonic acid, 17 parts by
weight of the sodium salt of a lignosulfonic acid from a
sulfite waste liquor and 60 parts by weight of pulverulent
silica gel, and the mixture is ground in a hammer mill.
45 Finely distributing the mixture in 20,000 parts by weight
of water gives a spray mixture which comprises 0.1% by
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66
weight of the active compound.
V. 3 parts by weight of the active compound No. Ib.3 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 active compound No. Ib.3 are
mixed intimately with 2 parts by weight of 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 active compound No. Ib.3 is
dissolved in a mixture composed of 70 parts by weight of
cyclohexanone, 20 parts by weight of ethoxylated
isooctylphenol and 10 parts by weight of ethoxylated castor
oil. This gives a stable emulsion concentrate.
VIII. 1 part by weight of the active compound No. Ib.3 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;
BASF AG). This gives a stable emulsion concentrate.
The active compounds I or the herbicidal compositions can be
applied pre- or post-emergence. If the active compounds 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 as far as
possible they do not come into contact 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 rates of application of active compound I are from 0.001 to
3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.),
depending on the control target, the season, the target plants
and the growth stage.
To widen the spectrum of action and to achieve synergistic
effects, the 1-aryl-4-thiouracils I may be mixed with a large
number of representatives of other herbicidal or
growth-regulating active compound groups and applied
concomitantly. Suitable components for mixtures are, for example,
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1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric
acid and its derivatives, aminotriazoles, anilides,
(het)aryloxyalkanoic acids and their derivatives, benzoic acid
and its derivatives, benzothiadiazinones,
2-(het)aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,
benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates,
quinolinic 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- and hetaryloxyphenoxypropionic esters, phenylacetic acid
and its derivatives, 2-phenylpropionic acid and its derivatives,
pyrazoles, phenylpyrazoles, 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 I,
alone or 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.
Preparation Examples
Example 1 (Compound Ib.3)
5-Fluoro-4-(5-fluoro-3-methyl-2-oxo-4-thioxo-3,4-dihydro-2H-
pyrimidin-1-yl)-2-(1-methylprop-2-ynyloxy)benzonitrile
At approximately 20~C, 1 g of "Lawesson's reagent"
{2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-di-
thione} was added to a solution of 1.7 g of
5-fluoro-4-(5-fluoro-3-methyl-2,4-dioxo-
3,4-dihydro-2H-pyrimidin-1-yl)-2-(1-methylprop-2-ynyloxy)-
benzonitrile in 50 ml of toluene. The mixture was subsequently
stirred at reflux temperature for 10 hours. The mixture was then
admixed with another 1 g of "Lawesson's reagent", and then heated
at reflux temperature for a further 10 hours.
For work-up, the cooled reaction mixture was initially
chromatographed over silica gel (mobile phase: toluene). The
resulting oil was stirred with isopropyl ether.
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The resulting solid was washed with petroleum ether and
subsequently dried. Yield: 0.45 g; m.p.: 181-188~C.
The following 1-aryl-4-thiouracils were prepared in a similar
manner:
Compound No. Ia.3 m.p.: 184-185~C;
5-fluoro-4-(3,5-dimethyl-2-oxo-4Tthioxo-
3,4-dihydro-2H-pyrimidin-1-yl)-2-(1-methyl-
prop-2-ynyloxy)benzonitrile m.p.: 147-148~C;
5-fluoro-4-(5-bromo-3-methyl-2-oxo-4-thioxo-
3,4-dihydro-2H-pyrimidin-1-yl)-2-(1-methyl-
prop-2-ynyloxy)benzonitrile m.p.: 175-180~C.
Use Examples
The herbicidal activity of the 1-aryl-4-thiouracils I was
demonstrated by the following greenhouse experiments:
The culture containers used were plastic flowerpots containing
loamy sand with approximately 3.0% of humus as the substrate. The
seeds of the test plants were sown 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 causes uniform
germination of the test plants, unless this was adversely
affected by the active compounds.
For post-emergence treatment, the test plants were first grown to
a plant height of from 3 to 15 cm, depending on the plant habit,
and only then treated with the active compounds which had been
suspended or emulsified in water. For this purpose, 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 the
treatment. The application rate for the post-emergence
application was only 31.3 or 15.6 g of a.s./ha.
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Depending on the species, the plants were kept at 10-25~C or
20-35~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.
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.
Table 2 below shows the superior herbicidal action of the
compound No. Ib.3, compared with the comparative compound A known
from w0 97/05117 (there Example 3)
H3C
p O-CH(CH3)-C- CH
~~(/N
O / N ~ ~ CN A
F F
Active Application Test plants
and damage
compound rate
[g of a.s/ha] Brachiaria
Amaranthus
Commelina
plantaginea
retroflexus
benghalensis
Ib.3 31.3 70 100 100
A 31.3 25 90 30
Ib.3 15.6 50 90 50
30A 15.6 15 70 30
40
