DERIVES SALICYLOYL(THIO)ETHER, LEUR PREPARATION ET INTERMEDIAIRES POUR LEUR PREPARATION

SALICYLOYL(THIO)ETHER DERIVATIVES, THEIR PREPARATION AND INTERMEDIATES FOR THER PREPARATION

Abrégé anglais

Salicyloyl(thio)ether derivatives of the formula I,
<IMG>
where X is oxygen or sulfur and Z is carbon or nitrogen,
and the radicals R1 to R4 and A have the meanings given in
the disclosure, and processes form preparing the same.
These derivatives have improved herbicidal properties or
other properties desirable in crop protection, such as
growth-regulating or fungicidal activity.

Revendications

104
CLAIMS
1. A salicyloyl(thio)ether derivative of the formula
I
<IMG>
where
R1 is a radical
<IMG>
in which m is 0 or 1 and R6 and R7 are each
hydrogen;
C1-C6-alkyl, C3-C6-alkenyl and C3-C6-alkynyl, where these
radicals may each carry from one to five halogen atoms
and/or one or two of the following groups: C1-C6-alkoxy,
C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkylthio, C3-C6-
alkenylthio, C3-C6-alkynylthio, C1-C6-haloalkoxy, cyano,
C1-C6-alkylcarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkynyl-
carbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl,
C3-C6-alkynyloxycarbonyl, C1-C6-dialkylamino or C1-C6-cyclo-
alkyl;
unsubstituted or substituted C1-C6-cycloalkyl;
unsubstituted or substituted phenyl;
R6 together with R7 may be an unsubstituted or substituted
C4-C7-alkylene chain in which a CH2 group may be replaced
with oxygen, sulfur or -NH;
a group
<IMG>

105
where R8 and R9 are each hydrogen, C1-C6-alkyl , C3-C6-
alkenyl or C3-C6-alkynyl and 1 is 1, 2, 3 or 4;
or a group
(CH2)1 - S (=O) k-R10
where R10 is C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, 1
is 1, 2, 3 or 4 and k is 0, 1 or 2;
a radical OR5, where
R5 is an unsubstituted or substituted 5-membered aromatic
heterocyclic structure bonded via a nitrogen atom and
having from one to four nitrogen atoms in the ring
or a radical
<IMG>
where R11 is C1-C6-alkyl, C3-C6-alkenyl, and C3-C6-alkynyl,
where these radicals may each carry from one to five
halogen atoms and/or orae or two of the following groups:
C1-C6-alkoxy, C3-C6-akenyloxy, C3-C6-alkynyloxy, C1-C6-
alkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C1-C6-
haloalkoxy, cyano, C1-C6-alkylcarbonyl, C3-C6-alkenyl-
carbonyl, C3-C6-alkynylcarbonyl, C1-C6-alkoxycarbonyl, C3-
C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-
dialkylamino or C1-C6-cycloalkyl,
-HN-SO2-R12
where R12 is C1-C6-alkyl, C1-C6-haloalkyl or phenyl, which
in turn may carry from one to four of the following
substituents: halogen, nitro, cyano or C1-C6-alkyl;
Rz and R3 are each C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-
alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
X is oxygen or sulfur;
Z is nitrogen or the methine group;
R4 is hydrogen, halogen, nitro, C1-C4-alkyl, cyano or
C1-C4-haloalkyl; and

106
A is a 5-membered heteroaromatic structure having from
one to four nitrogen atoms or from one to three nitrogen
atoms and additionally a sulfur ar oxygen atom in the
ring, which may carry from one to three halogen atoms
and/or from one to three of the following radicals:
vitro, cyano, C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkyl
or phenyl which is unsubstituted or substituted by from
one to three halogen atoms and/or from one to three
methyl groups;
a benzofused 5-membered heteroaromatic structure which
may contain from one to three nitrogen atoms or a nitro-
gen atom and additionally one oxygen or sulfur atom and
may carry one of the following radicals: C1-C4-alkyl,
halogen or cyano;
a thienyl or furyl radical which may carry from one to
three halogen atoms and/or from one to three of the
following radicals: C1-C4-alkyl, C1- or C2-haloalkyl,
unsubstituted or substituted phenyl or nitro;
a benzothienyl or benzofuryl radical which may carry one
halogen atom and/or one of the following radicals: C1-
C4-alkyl, C1- or C2-haloalkyl or nitro;
pyridyl which may carxy from one to three halogen atoms
and/or from one to three of the following radicals: C1-
C4-alkyl, C1- or C2-haloalkyl, unsubstituted or sub-
stituted phenyl or nitro;
a naphthyl or quinolyl radical, each of which may carry
up to three halogen atoms and/or up to three of the
following radicals: C1-C4-alkyl or C1- or C2-haloalkyl,
the expression unsubstituted or substituted in the
abovementioned cases meaning that the corresponding
groups may carry one or more of the following substitu-
ents: halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl,
C1-C6-alkoxy or C1-C6-alkylthio.

107
2. A salicylic acid derivative of the formula I as
claimed in claim 1,
where
R1 is a group
<IMG>
where m is 0 or 1 and R6 and R7 are each hydrogen or
methyl or R6 and R7 together form a C4- or C5-alkylene
chain;
R2 and R3 are each methoxy, methyl, difluoromethoxy or
chlorine;
R4 is hydrogen or methyl;
X is oxygen;
Y is nitrogen;
Z is the methine group and
A has the meanings stated in claim 1.
3. A salicylic acid derivative of the formula I as
claimed in claim 1, where R1 is O-N(CH3)2, X is oxygen, Y
is nitrogen, Z is the methine group and R2 and R3 are each
methoxy and A are defined as in claim 1.
4. A process for the preparation of a compound of the
formula I as claimed in claim 1, wherein the corresponding
salicylic acid or thiosalicylic acid derivative of the
formula II
<IMG>

108
is reacted with a heteroaromatic structure of the formula
III
<IMG>
wherein R13 is a nucleofugic leaving group, in the presence
of an inorganic or organic base.
5. A process for the preparation of a compound of the
formula I as claimed in claim 1, wherein the free salicylic
acid or a sulfur analog thereof of the formula I'
<IMG>
is first converted into the halide or another activated
form of the carboxylic acid and this is then reacted, in
the presence or absence of an inorganic or organic base,
with an unsubstituted or substituted hydroxylamine, N-
hydroxyazole, hydroxyalkyl phosphonate or sulfonamide.
6. A herbicide containing a compound of the formula I as
claimed in claim 1, 2 or 3 and conventional inert
additives.

109
7. A method for controlling undesirable plant growth,
wherein the undesirable plants or their habitat is or are
treated with a herbicidal amount of a derivative I as
claimed in claim 1, 2 or 3.
8. A method for regulating plant growth, wherein an
amount, having a regulatory effect, of a salicylic acid
derivative of the formula I as claimed in claim 1, 2 or 3,
is allowed to act on the seeds, the plants or their
habitat.
9. A fungicide or nitrification inhibitor, containing a
salicylic acid derivative of the formula I as claimed in
claim 1, 2, or 3 and conventional inert additives.

Description

2075~8~
O.Z. 0050/42589
Salicyloyl(,thio)ether derivatives, their preparation
and intermediates for their preparation
The present invention relates to salicyloyl-
(thio)ether derivatives of the formula I
R3
R'~ ~
/ N %\ Z
~I ~ ~ z
A
X N R2
0 / Ri
where
R1 is a radical
R6
~O) m - N
\ 7
R
in which m is 0 or 1 and Rs and R' are each
hydrogen;
C1-Cs-alkyl, C3-C6-alkenyl, C3-Cs-alkynyl, where these
radicals may each carry from one to five halogen atoms
and/or one or two of the following groups: C1-Cs-alkoxy,
C3-Cs-alkenyloxy, C3-Cs-alkynyloxy, C1-Cs-alkylthio, C3-Cs-
alkenylthio, C3-Cs-alkynylthio, Cl-Cs-haloalkoxy, cyano,
C1-Cs-alkylcarbonyl, C3-Cs-al:kenylcarbanyl, C3-Cs-alkynyl-
carbonyl, Cl-Cs-alkoxycarbonyl, C3-Cs-alkenyloxycarbonyl,
C3-Cs-alkynyloxycarbonyl, C1-Cs-dialkylamino or Cl-Cs-cyclo-
alkyl;
unsubstituted or substituted C1-Ca-cycloalkyl;
unsubatituted or substituted phenyl;
Re together with R' may be an unsubstituted or substituted
G4-C,-alkylene chain in which a CHI group may be replaced
with oxygan, sulfur or -NH;
a group o
~~ / Rs
- (CHZ) 1 C - N
\ 9
R

2075~8~
- 2 - O.Z. 0050/42589
where Ra and R9 are each hydrogen, C1-CB-alkyl, C3-CB-
alkenyl or C3-C6-alkynyl and 1 is 1, 2, 3 or 4;
or a group
(CHz) 1 - S (=0) k-Rio
where Rl° is C1-Cs-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, 1
is 1, 2, 3 or 4 and k is 0, 1 or 2;
a radical ORS, where
RS is an unsubstituted or substituted 5-membered aromatic
heterocyclic structure bonded via a nitrogen atom and
having from one to four nitrogen atoms in the ring
or a radical
0
(CHZ)i- P - ORli
ORli
where Rll and 1 have the abovementioned meanings,
or a radical
-~-SOZ-RI2
where R12 is C1-CB-alkyl, Cl-C6-haloalkyl or phenyl, which
in turn may carry from one to four of the following
substituents: halogen, vitro, cyano or C1-CB-alkyl;
R2 and R3 are each C1-C4-alkyl, C1-C~-haloalkyl, Cl-C4-
alkoxy, C1-C,-haloalkoxy and/or Cl-C4-alkylthio;
X is oxygen or sulfur;
Z is nitrogen or the methine group;
R" is hydrogen, halogen, vitro, C1-C,-alkyl, cyano or C1-
C,-haloalkyl; and
A is a 5-membered heteroaromatic structure having from
one to four nitrogen atoms or from one to three nitrogen
atoms and additionally a sulfur or oxygen atom in the
ring, which may carry from one to three halogen atoms
and/or from one to three of the following radicals:
vitro, cyano, C1-C4-alkyl, C1-C~-alkylthio, C1-C~-haloalkyl
or phenyl which is unsubstituted or substituted by from
one to three halogen atoms and/or from one to three

20'~~~8~
- 3 - O.Z. 0050/42589
methyl groups;
a benzofused 5-membered heteroaromatic structure which
may contain from one to three nitrogen atoms or a nitro-
gen atom and additionally one oxygen or sulfur atom and
may carry one of the following radicals: C1-C4-alkyl,
halogen or cyano;
a thienyl or furyl radical which may carry from one to
three halogen atoms and/or from one to three of the
following radicals: C1-C4-alkyl, C1- or CZ-haloalkyl,
unsubstituted or substituted phenyl or vitro;
a benzothienyl or benzofuryl radical which may carry one
halogen atom and/or one of the following radicals: C1-
C4-alkyl, Cl- or CZ-haloalkyl or vitro;
pyridyl which may carry from one to three halogen atoms
and/or from one to three of the following radicals: C1
C4-alkyl, C1- or CZ-haloalkyl, unsubstituted or sub
stituted phenyl or vitro;
a naphthyl or quinolyl radical, each of which may carry
up to three halogen atoms and/or up to three of the
following radicals: C1-C4-alkyl or C1- or CZ-haloalkyl,
the expression unsubstituted or substituted in the
abovementioned cases meaning that the corresponding
groups may carry one or more of the following substitu
ents: halogen, vitro, cyano, C1-CB-alkyl, C1-C~-haloalkyl,
C1-C6-alkoxy or Cl-CB-alkylthio.
The literature (EP-A 223 406, EP-A 249 708,
EP-A 426 476, EP-A 287 072, EP-A 287 079, EP-A 346 789 and
EP-A 402 751> describes herbicidal, substituted salicyclic
acids and sulfur analogs thereof. However, their action is
not always satisfactory.
It is an object of the present invention to
provide novel salicylic acid derivatives or sulfur
analogs thereof having improved herbicidal properties or
other properties desirable in crop protection, such as
growth-regulating or fungicidal activity.
We have found that this object is achieved by the
compounds of the formula I which are defined at the
outset. We have also found processes for the preparation

~o~~~ss
- 4 - O.Z. 0050/42589
of the compounds I and methods for controlling un-
desirable plant growth with the compounds I. We have
furthermore found that salicylic acid derivatives of the
general formula I defined above have excellent plant
growth-regulating properties and in addition possess
fungicidal and nitrification-inhibiting activity. The
novel salicylic acid derivatives II' were found as
intermediates for the preparation of the compounds I.
Compounds of the formula I are obtained, for
example, by reacting a correspondingly substituted
salicylic acid derivative of the formula II, which is
known in specific cases or can be prepared by convention
al methods, starting from known intermediates, with a
corresponding compound of the formula III in the presence
of a base.
R2
XH
Base
Rq ~ R + R13 ~~ / Z _HR12 ~' I
A 0
R3
II III
In the formula III, R13 is a conventional nucleo-
fugic leaving group, for example halogen, such ae chlor-
ine, bromine, iodine, arylsulfonyl or alkylsulfonyl, such
as toluenesulfonyl or methylsulfonyl, or another equiva-
lent leaving group. Compounds of the formula III having
a reactive substituent RlZ are known or can readily be
obtained with the general technical knowledge. Suitable
bases are alkali metal or alkaline earth metal hydrides,
such as NaH or CaH2, alkali metal hydroxides, such as NaOH
or KOH, alkali metal alcoholates, such as potassium tert
butylate, alkali metal carbonates, such as NaZC03 or
KZCO3, alkali metal amides, such as NaNH2 or lithiumdiiso
propylamide, or tertiary amines. When an inorganic base
is used, a phase transfer catalyst may be added if it
promotes the conversion.
Compounds of the formula I can also be prepared

2~'~~~86
- 5 - O.Z. 0050/42589
by starting tram the corresponding carboxylic acids, ie.
compounds of the formula I in which R1 is hydroxyl, and
first converting them in a conventional manner into an
activated form, such as a halide or imidazolide, and then
reacting this with the corresponding hydroxy compound.
These two steps can also be simplified, for example, by
allowing the carboxylic acid to act on the hydroxy
compound in the presence of a water-eliminating agent,
such as a carbodiimide.
Where X is oxygen and A is a heteroaromatic
structure bonded via a carbon atom, the intermediates of
the formula III can be synthesized according to the
following scheme from a l, 3-dicarbonyl compound IV (where
RS is unsubstituted or phenyl-substituted Cl-Clo-alkyl, in
particular C1-C4-alkyl) and an a "B-unsaturated ketone V:
A if Base / OH
2~ acid
3> bromine R4
0 4~ -HBr A 0
IV V
(A is a heteroaromatic or aromatic structure bonded via
a carbon atom)
The compounds IV and V are generally known or can
be readily prepared by the conventional methods. The
abovementioned compounds can be used as the base.
Suitable acids are strong acids, for example hydrochloric
acid, hydrobromic acid, tetrafluoboric acid, toluene-
sulfonic acid or trifluoroacetic acid. The elimination
of hydrogen bromide may be carried out thermally or in
the presenoe of a base, for example of an organic amine.
If, in the formula II, A is a heteroaromatic
structure bonded via a nitrogen atom and X is oxygen,
this intermediate may be synthesized according to the
following scheme:

2~'~~~86
- 6 - O.Z. 0050/42589
RQ R /
\ \
F O / A OH
CN M+A- R1 \ O IIb
VI
1~ HC1/alcohol
2~ HCl/Hy0
Ry 3> pBr3
\ /
A 0
CN
VII
(A is a heteroaromatic structure bonded via N)
M+A is the particular alkali metal azolide. G1-
C4-Alkyl alcohols are particularly suitable alcohols for
the cleavage of the nitrile VII.
The intermediates of the formula II which are
prepared as described above are usually obtained as alkyl
esters. These can be hydrolyzed by the known methods to
give the carboxylic acids. The latter can be converted
by methods known from the literature into various esters
which are required for the prepararion of the active
ingredients of the formula I as claimed in claim 1.
With regard to the herbicidal and plant growth-
regulating activity, preferred compounds I axe those in
which the substituents have the following meanings:
Rl is a radical
Rs
--'-- (0) m~~
R'
where m is 0 or 1 and R~ and R' are each
hydrogen=
alkyl, in particular methyl, ethyl, propyl, 1-methyl
ethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1
dimethylethyl, n.~pentyl, l-methylbutyl, 2-methylbutyl, 3

2075~8~
- 7 - O.Z. 0050/42589
methylbutyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-
ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-
methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-
dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-
dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethylbutyl, 1-ethyl-2-methyl-
propyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methyl-
hexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-
ethylpentyl, 1-propylbutyl or octyl;
alkenyl, such as 2-propenyl, 2-butenyl, 3-butenyl, 1-
methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-
pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-
butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-
methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-
propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-
hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-
pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-
methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-
pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-
methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-
pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,
1,1-dimethyl-3-butenyl, 1,2-dimethyl-3-butenyl, 1,2-
dimethyl-3-butenyl,l,3-dimethyl-2-buteny1,1,3-dimethyl-
3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-
butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 2-
ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-3-butenyl,
1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,
1-ethyl-2-methyl-2-propenyl, in particular 2-propenyl, 2-
butenyl, 3-methyl-2-butenyl or 3-methyl-2-pentenyl;
alkynyl, such ae 2-propynyl, 2-butynyl, 3-butynyl, 1-
methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-
methyl-3-butynyl,2-methyl-3-butynyl,l-methyl-2-butynyl,
1,1-dimethyl-2-propynyl, 1-ethyl-2-gropynyl, 2-hexynyl,
3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 4-
methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-
pentynyl, 1-methyl-4-pentynyl, 2-methyl-9:-pentynyl, 3-
methyl-4-pentynyl, l,l-dimethyl-2-butynyl, 1,1-dimethyl-

20'~~~80
- 8 - O.Z. 0050/42589
3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-
butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-
3-butynyl or 1-ethyl-1-methyl-2-propynyl, preferably 2-
propynyl, 2-butynyl, 1-methyl-2-propynyl or 1-methyl-2-
butynyl, in particular 2-propyl or 1-methyl-2-propynyl.
The abovementioned alkyl, alkenyl or alkynyl
groups may each carry from one to five halogen atoms,
preferably fluorine and chlorine and/or one or two of the
following radicals:
cyano;
alkoxy of one to four carbon atoms, in particular meth-
oxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methyl-
propoxy, 2-methylpropoxy or 1,1-dimethylethoxy, prefer-
ably methoxy, ethoxy or 1-methylethoxy;
alkenyloxy of one to four carbon atoms, in particular
ethenyloxy, propenyloxy, 1-methylethenyloxy, butenyloxy,
1-methylpropenyloxy, 2-methylpropenyloxy or 1,1-dimethyl-
ethenyloxy, preferably ethenyloxy or 1-methylethenyloxy;
alkynyloxy of one to four carbon atoms, in particular
ethynyloxy, propynyloxy, 1-methylethynyloxy, butynyloxy,
1-methylpropynyloxy, 2-methylpropynyloxy or 1,1-dimethyl-
ethynyloxy, preferably ethynyloxy or 1-methylethynyloxy;
alkylthio of one to four carbon atoms, in particular
methylthio, ethylthio, propylthio, 1-methylethylthio,
butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-
dimethylethylthio, preferably methylthio, ethylthio or 1-
methylethylthio;
alkenylthio of one to four carbon atoms, in particular
ethenylthio, propenylthio, 1-methylathenylthio, butenyl
thio, Z-methylpropenylthio, 2-methylpropenylthio or 1,1
dimethylethenylthio, preferably ethenylthio or 1-methyl-
ethenylthio;
alkynylthio of one to four carbon atoms, in particular
ethynylthio, propynylthio, 1-methylethynylthio, butynyl
thio, 1-methylpropynylthio, 2-methylpropynylthio or 1,1
dimethylethynylthio, preferably ethynylthio or 1-methyl-
ethynylthio;

207~~8~
- 9 - O.z. 0050/42589
haloalkoxy, such as difluoromethoxy, trifluoromethoxy,
chloradifluoromethoxy, dichlorofluoromethoxy, 1-fluoro-
ethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-
tetrafluoroethoxy,2,2,2-trifluoroethoxy,2-chloro-1,1,2-
trifluoroethoxy or pentafluoroethoxy, in particular
difluoromethoxy or trifluoromethoxy;
alkylcarbonyl, in particular methylcarbonyl, ethyl-
carbonyl, propylcarbonyl, 1-methylethylcarbonyl, butyl-
carbonyl, 1-methylpropylcarbonyl, 1,1-dimethylethyl-
carbonyl, pentylcarbonyl, 2-methylbutylcarbonyl, 1,1-
dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-
dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexyl-
carbonyl,l-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-tri-
methylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,
1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methyl-
propylcarbonyl; alkoxycarbonyl, such as methoxycarbonyl,
ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl,
butoxycarbonyl,l-methylpropoxycarbonyl,2-methylpropoxy-
carbonyl, l,l-dimethylpropoxycarbonyl, n-pentyloxy-
carbony, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,
3-methylbutoxycarbonyl, 1,2-dimethylpropoxycarbonyl,
1,1-dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl,
1-ethylpropoxycarbonyl, 1-hexyloxycarbonyl, 1-methyl-
pentenyloxycarbonyl, 2-methylpentenyloxycarbonyl,
3-methylpentenyloxycarbonyl, 4-methylpentenyloxycarbonyl,
1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl,
2,3-dimethylbutoxycarbonyl, 1,1-dimethylbutoxycarbonyl,
2,2-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,
1,1,2-trimethylpropoxycarbonyl, 1,2,2-tr~.methylpropoxy-
carbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,
1-ethyl-2-methylpropoxycarbonyl, n-heptyloxycarbonyl,
1-methylhexyloxycarbonpl, 2-methylhexyloxycarbonyl,

20~~~~6
- 10 - O.Z. 0050/42589
3-methylhexyloxycarbonyl, 4-methylhexyloxycarbonyl,
5-methylhexyloxycarbonyl, 1-ethylpentenyloxycarbonyl,
1-propylbutoxycarbonyl or octyloxycarbonyl, in particular
methoxycarbonyl, ethoxycarbonyl, 1-methylethoxycarbonyl
or 1-methylpropoxycarbonyl;
cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl or cycloheptyl;
dialkylamino, such as dimethylamino, diethylamino,
dipropylamino, di-1-methylethyl, dibutylamino, di-1
methylpropylamino,di-2-methylpropylamino,di-1,1-methyl
ethylamino, ethylmethylamino, propylmethylamino, 1-
methylethylmethylamino or butylmethylamino;
phenyl, phenoxy or phenylcarbonyl, where these aromatic
radicals in turn may carry from one to five halogen atoms
as stated above, in particular fluorine, chlorine and
bromine, _and/or from one to three of the following
radicals: alkyl, haloalkyl, alkoxy and/or alkylthio,
each of one to four carbon atoms, as stated above in
general and in particular;
C3-Clz-cycloalkyl, in particular C3-Ce-cycloalkYl, such as
cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which
is unsubstituted or substituted by one to three C1-C4-
alkyl radicals;
phenyl which is unsubstituted or monosubstituted to
trisubstituted by C1-C4-alkyl or C1-C4-alkoxy, such as
methyl, ethyl, propyl, butyl, methoxy or ethoxy or phenyl
which is substituted by one to five halogen atoms, eg.
chlorine or fluorine;
RB and R' together form an alkylene group which is closed
to form a ring, or together form an alkylene group which
has a hetero atom and is clpsed to form a ring, the ring
preferably having from five to seven members and the
hetero atom being oxygen, nitrogen or sulfur, and the
ring thus formed carries one or more of the radicals
stated under unsubstituted or substituted.
The following radicals may be mentioned in
particular for the group -NReR': dimethylamino,

207558
- 11 - O.Z. 0050/42589
tertbutylamino, cyclohexylamino, 1-cyano-1-cyclohexyl
amino, isopropylamino, sec-butylamino, methylamino,
diethylamino, 1-pyrrolidinyl, 1-piperidyl, 4-morpholinyl,
phenylamino, methylphenylamino, methaxymethylamino, bis
(methoxymethyl)-amino or methylthiomethylamino;
a radical O
Ra
- (CHz) 1'- C - N
\ 3
R
where 1 is from 1 to 4, preferably 1 or 2, and Re and R9
are each alkyl, alkenyl or alkynyl as stated above;
a radical
- (CHI) ~-S (~O) k-Rlo
where 1 is from 1 to 4, preferably 1 or 2, and Rl° is
alkyl, alkenyl or alkynyl as stated above;
a radical OR$, where
RS is a 5-membered hetaryl which has from one to four
nitrogen atoms in the ring, is bonded via a nitrogen atom
r5 and may carry from one to four of the radicals stated
under unsubstituted or substituted. Particular examples
are 1-pyrazolyl, 3-methyl-1-pyrazolyl, 4-methyl-1-
pyrazolyl, 3,5-dimethyl-1-pyrazolyl, 3-phenyl-1-
pyrazolyl, 4-phenyl-1-pyrazolyl, 4-chloro-1-pyrazolyl,
4-bromo-1-pyrazolyl, 4-iodo-1-pyrazolyl, 1-imidazolyl,
1-benzoimidazolyl, 7.,2,4-triazol-1-yl, 3-methyl-1,2,4-
triazol-1-yl, 5-methyl-1,2,4-triazol-1-yl or 1-benzo-
triazolyl, .
or a group
0
(CH2) 1-" P ""' ORi1
ORl l

CA 02075586 2002-02-18
- 12 -
where 1 is from 1 to 4, preferably 1 or 2, and Rll is
alkyl, alkenyl or alkynyl as stated for R6 and R'.
a radical
-HN-SOZ-Rlx,
where R12 has the following meanings:
C1-C6-alkyl which may carry from one to four of the
following substituents: halogen, nitro, cyano or C1-C6-
alkyl, particular examples being methyl, cyanomethyl,
ethyl, 2-nitroethyl, propyl, 1-methylethyl, butyl, 1-
methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-
pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-
dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-
hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-
methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-
dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-
dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethyl-
propyl, 1-ethylbutyl or 1-ethyl-2-methylpropyl;
phenyl which may carry from one to four of the following
substituents: halogen, nitro, cyano or C1-C6-alkyl,
particular examples being 2-fluorophenyl, 3-fluorophenyl,
4-fluorophenyl, 2,6-difluorophenyl, 2,4-difluorophenyl,
2,3-difluorophenyl, 2-fluoro-4-trifluoromethylphenyl, 2-
chlorophenyl, 3-chlorophenyl, 2-bromophenyl, 2-iodo-
phenyl, 2-chloro-6-fluorophenyl, 2,4-dichlorophenyl, 2,6-
dichlorophenyl, 3,5-dichlorophenyl, 2-chloro-4-fluoro-
phenyl, 2-chloro-6-methylphenyl, 2,3,5-trichlorophenyl,
2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,6-
dimethylphehyl, 2,4-dimethylphenyl, 3,5-dimethylphenyl,
2,4,6-trimethylphenyl, 2-chloro-4-methylphenyl, 2-tri-
fluoromethylphenyl, 3-trifluoromethylphenyl, 2-cyano-
phenyl, 3-cyanophenyl, 4-cyanophenyl, 2-nitrophenyl, 3-
nitrophenyl or 4-nitrophenyl;
RZ and R3 are each in general and in particular the alkyl,
haloalkyl, alkoxy, haloalkoxy and/or alkylthio groups
stated for RB and R', each of one to four carbon atoms, in
particular methyl, trifluoromethyl, methoxy, difluoro-
methoxy or methylthio;

20'~~5~6
- 13 - O.Z. 0050/42589
R° is hydrogen; halogen, in particular fluorine or chlor-
ine, cyano; alkyl of one to four, in particular one to
three, carbon atoms which is monosubstituted to penta-
substituted by halogen, in particular fluorine or chlor-
ine. Examples are methyl, ethyl, n-propyl, isopropyl,
trichloromethyl and trifluoromethyl.
A is unsubstituted or substituted 5-membered
hetaryl having from one to four nitrogen atoms, such as
pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-
triazolyl or tetrazolyl, or having one or two nitrogen
atoms and in addition one sulfur or oxygen atom, such as
isoxazolyl, oxazoly, thiazolyl or thiadiazolyl;
examples of hetaryl radicals are the followings
pyrrol-1-yl, 2-methylpyrrol-1-yl, 3-methylpyrrol-1-yl, 1-
methylpyrrol-2-yI, 1-methylpyrrol-3-yl, pyrazol-1-yl, 4-
methylpyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 3,4,5-
trimethylpyrazol-1-yl, 4-chloropyrazol-1-yl, 4-phenyl-
pyrazolyl-1-yl, 4-nitropyrazol-1-yl, imidazol-1-yl, 4,5-
dimethylimidazol-1-yl, 2-methyl-4,5-dichloroimidazol-1-
y1, 4-nitroimidazol-1-yl, 5-nitroimidazol-1-yl, 1,2,4-
triazol-1-yl, 3(5)-methyl-1,2,4-triazol-1-yl, 1,2,3-
triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 1,2,3,4-
tetrazol-1-yl, l-methylpyrazol-4-yl, 1-phenylpyrazol-4-
yl, 1,3,5-trimethylpyrazol-4-yl, 1-methylpyrazol-5-yl,
1-phenylpyrazol-5-yl, 1-methylpyrazol-3-yl, 1-phenyl-
pyrazol-3-yl, 1-methylimidazol-2-yl, 1-methylimidazol-5-
yl, 1-phenylimidazol-5-yl, 1-phenyl-1,2,3-triazol-4-yl,
isoxazol-S-yl, isoxazol-4-yl, 4-methylisoxazol-5-yl, 3-
isopropylisoxazol-5-yl, 3-phenylisoxazol-5-yl, oxazol-2-
y1, 2-methylaxazol-4-yl, thiazol-4-yl, 4-methylthiazol-
2-yl, 4-methylthiazol-5-yl, 2-phenylthiazol-5-yl and 4-
phenylthiazol-2-yl;
unsubstituted or substituted benzofused hetaryl having
from one to three nitrogen atoms or one nitrogen atom and
one oxygen or sulfur atom in the ring, for example
indolyl, indazolyl, benzotriazolyl, benzoxazolyl, benzo-
isoxazolyl or benzothiazolyl;

207~5~~
- 14 - O.Z. 0050/42589
unsubstituted or substituted thienyl radicals or benzo-
thienyl radicals are, for example, 2-thienyl, 3-thienyl,
2-chloro-5-thienyl,4-bromo-2-thienyl,2-vitro-5-thienyl,
2-benzothienyl and 3-benzothienyl; and
unsubstituted or substituted naphthyl or quinolyl radi-
cals are, for example, 1-naphthyl, 2-naphthyl, 2-chloro-
1-naphthyl,6-chloro-1-naphthy1,2,6-dichloro-1-naphthyl,
2-methyl-6-chloro-1-naphthyl, 2-quinolyl, 4-quinolyl, 6-
quinolyl, 8-quinolyl and 6-methyl-2-quinolyl.
If a radical is referred to as unsubstituted or
substituted, it may carry one or more, in particular from
one to three, of the following substituents: halogen, in
particular chlorine or bromine, vitro, cyano or alkyl,
haloalkyl, alkoxy or alkylthio as stated for Re and R'.
Particularly preferred compounds of the formula
I are those in which
RZ and R3 are each methoxy, methyl, difluoromethoxy or
chlorine,
R° is hydrogen or methyl and
R6 and R' are each hydrogen, methyl or a Ca- or CS-alkylene
chain
and in which X is oxygen, Y is nitrogen and Z is a
methine group and A has the meanings stated in the claim.
The structures given in the tables below describe
particularly preferred active ingredients of the formula I.

r
1
i
N
w
O
O
1n O
O
O N
a~ O
ro
o
;.
,~
a
,,.,
~ ~,
0 0 0 0 0 0 0 0 0 0 0 0
s~ :a>.~s~s-~~ s~>.~sas~~ la
N ~ ~ ~-IH S~H S-as~~ S~N
p
1 I I 1 I I I I I I I I
,~ e-I'-i~-1.--1-m--I,-~~-I~-i~ ~-i~.-I
x N
~
o x x x x x
z x x x x x x V U U U
p \
~ N z U U U U U U U
z
~
o x o 0 0 0 0 0 0 0 0 0 0 0
\ / \ x
U
tn p c~~ r u~T 11
~ x x ~ x
x ~
m ,n U
'
~ U U x x U U ~ ~ ~ f~~ U ,
U
.,.1
r1
H
;a
~
' U
I
I
x U
N ,,~
ri r W m x U
U U ~
P: U U x U x x x x U
O
Ifl ~
r1 r N
l
u~ o
N M

20'~~~85
N
0
O
t(1 0
0
O N
41 O
~
o
r
m
~ r1r1 ~
I 1 I I I
N N N M M
I I I I I
r-ir-1r-Ir1 r1
O O O O O
f-1N N ~ i-a
S-~1-~N N N
r1 r-1r-1r1r1r1r-1ri r1riri~1ririr-Ir-Ir1~ 1~(l~
5r ?i~r~r~r~,~ ~r ?~~ 5r?r? Wr7v ? W,I I I I I
r-Ir-ir-1r-1r1r1r-Ir1 r1r-1r1r-1r-1r1r-ir-1r1r-ir1r--Iri r-1
O O O O O O O O O O O O O O O O O ~.,?i~,~, ~r
~ f 1'd~I~1S-1~'-1~i f-IS-11-1~i~-1S~-I1~i~-11'a.~'.~,.4'.~.i.C,
1
i - ~IS-1S-I~11'-1~-IS-IS-1S-I~1~1S-1S-1~1~-I~ 1J+J1.11~
~-1F-I
'
'
u I I 1 I
~Q,'I ! I I 1 I I I I I I 1 I I I I I I -1v--ir-1v-I
r1 v-iri~-iv-~Iw-iwiw-Iv-!r1c-Irir-i~-1r1 w-1v-1W
U U U U U U
N U U U U U U U U U U U U .?~U z U
5C O O O O O O O O O O O O O O O O v1O O u1O O
r-F
x M M x (~1
II aCo O O x ~
N '~ N I U U N
N N U x M M M M
N x N x N N N N x U N N s1 x
x x x x ~
x x U x ~ x x x N U U U U U U
'~
G4 U U " U U U U U U U U N N
x
x'x x U
U U U O
N N N N
x x x x
U U U U
N N N
N x x x
x
U U U U
I I I I
M M
x M x
v a
x a o a ~ c
n
ii x'= o z x x .,
N N
x N M x M M M f'1'"1M
N N U N M N N x x U x x x x x x
x x x x x x
G~ U U ~ U U U U x x U U v U U U U U U
o ~1 0 ~
-! ,-1 N N M

20'~~~80
N
0
0
0
A N
~i
41 O
N
.u
~,
0
N
~a
w
>~
I
I c-i
I
I
o ~'
r, r1
o a
o .~~, ~ ~, o
~ x
I ? Wr'ro ~. 7,?,~ ? Wr.uW , I N ~ ~y~r?t ?~
M I I I I I I I ~,.l a ~ ~ l ~ ~ ?il a l I
I N M u-IS-1'W ~-I<-iI rlI .~.,O r1,'~yO I M I N M
r-i I I I ~,I I I ~-1I r-1rii-1I 1~~I~-II r-iI I
O r-Irir-1p,ri r-ir~I r-I'~.,'d~ r-iN O I r-I'>.,.-1r-1
'' ! -~O '1O O
'' '
S-I O O O I O O O r-IO .>~I 'r O . ~ .
s~ b ~ b ~ >'Is~s~O ~I.~~,a s~~ ~ O f-I~ ?-fS~-I
~t Li1_iS=i'r~-1~1S~-IT-1~-I~ ~ r1 ~1a W ~1 ~
1
-rl-rir1~i'r ~r~r~.I",r~1~M ~t ~r~ '~~-I~r~ ~r
-~I a a I s~~ a -~a a
~, ~.,1 I I ~ a a a ~ a s~o o r1r,~ , ~ s~~, ,-
~ ~I~ a~r, .-,o a ~ H ~ s~ ~ ~.N a ~ H
7,I~~, ~ s~o >, o
.~ o ,~.>~.a.~,.,~,~o ~ a I o a ,~,~.
.u ~d~..~.u.uA ~ ~ r,o ~ u,~ o ~ ~ 1~~ W n
N G N N N I N N ,~~ ,.~. .L;U7 .~N I .r1,.~. .>~.~
I-I~ ~ ~ ~,~ ~ v .>~w a~U I-Ia.W n z w M w w
I I I I I I I I
F(,'1 I I I I M I I 1 I I M V'~ M M M W -i~-1r1 c-1
w-ir-1u-W-iM M ~ V~C~~
x x x x x x x x x x x x x x x x x x x x x x
N U U U U U U U U U U U U U U U U U U U U U U
9C u~ O O O O O O O O O O O O O O O O O O O O O
M M M M M M M M M M M M M M M M M M t M ~t ~t
U U U U U U U U U U U U U U
P4 U U U U U U U U
1
M M M M M M M M M M M M M M M M M M M M M t
x ~x~x~xlx~x~x lx~x~x~x~xf lx lx~x~x~xtx~x~x ~x~
x
P4 U U U U U U U U 'U'UU U U U U ,UU U U U U U
o u~ c
,~-~ r~.l N N cn

2075~8fi
N
0
o
111 O
O
d~
o N
v~ O
N
~
o
'
?~
C~
W
I
cr
r1 .-ir-iI r
M ~ N ~-1Lfl
I I t ~1I
ri ~-Ir~ ~,r~i
r1 O r-I.-ir-1O O Cl~O r~ri
~ I
I ~ 1 I I S-I~t r-IS.1I I
M ,'~yM ~ M 5y',~.~,'~,'r1f1In
~ I Cl ' R I I
1 ( I I ~ p,, C,~ ~
~ , ~ ~ 1 I ~ I
I
Gp O r-1O O O ~ ~-i.Lir-IO O
S-Ir1t~.1~iI.d7r~ ~ ~t1~.11..1
~ " f S ~ i -i 1 '"f 1
1 S
i .,i -1-I~ 1 r1~ -
5.,( ~.,?,~,v v , >.,~.,
v v
c~ ,~a a a .~.t~I ,~t~s~
x
1.JI !.~1~1~I I 1~I 1J.G.1r-1rir-ir-Ir-ir-1r-Ir-1r-ir-Ir-I
N ~-1N v v r1.-iN riN N '.,~,7, ?,Jr?,? W,?,~, ?i
~ t~~ ~ ~ ~ ~ ~ ~ >~f~>~ ~ ~ G ~ 1~G f~ f~
v v v v v v v v v v
~.1.u~1A Cas~~ ~.1a ~.1~1w .~.,~.,~.~,..-,...i.
~ ~ M ~ H H H H H ~ ~ o ~ H
v~ W n m u1~ ~ ~ E I I I 1 I C C E C I
I I I -~ -~-~n -~
I I I I I
Q,'e-1I ric1r1M tn M M s-1~-1N N N N N N N N N N N
II1
x x x x x x x x x x x x x x x x x x x x x
N U U U U U U U U U U U Z U U U U U U U U U U
>C O O O O O O O O O O O O O O O O O O O O O O
h h h cn ~
x x x x x
M M M M M M M M M M M M M x x U U U U U
h x x x x x x x x x x x x x N ~~I I I I I
(x U U U U U U U U U U U U U x x U U f~
h
x
M
M M M M M M M M M M M M M M M U1 U
x
x x x x x x x x x x x x x x x N I
lx U U U U U U U U U U U U U x U U U x ~ x x x
o u1 0
v-1 N N ~'~1

r ~~
T
1
N
O
O
If1 O
O
o N
o~ O
b
d
o
'
~
f~
r1r1r1r1rir1 r1r-1rir1r1r1r1 r-Ir-1r-Ir-Ir1r1 '--Irir1
G ~ ~ ~ ~ ~ A ~ ~ f~f~t~~ t~ t~A ~
G G t~~ G N N > f s t N t N N ~ ~ ~ N ~ ~ N
N N N N N N N N N N
.,
EnE~E~H E-~E-~E~EiE1EiN E~Ei E-~EnC-~H E-~E-~E-~E-~E-~
I I I I I I I I I 1 I I I I I 1 I I I I
I I N N N N N N N N N N N N N N N N M M M M
N N
U U U U U U U U U U U U
N U U U U U U U U U z
SC O O O O O O O O O O O O O O O O O ~nO O O O
r-i
'
N r r1 I
1 N
x ~ ~ x x z ~ v
II N O N N N ~ " " CN
' '
U N ~(~ N N
O O ~ U
U U V N ~ U U ~ "~ I U U
x N U N N x ~~
N N N U N N N x , x x x U ~VN N x x x x
x x x x x x ~ x x x v
(.L U U U ~ U U U U ~ U U U v N U U x U U U x x
x ~ x U
x
U U U O
N N N N
x x x x
U U U U
N f'7N CJ
x x x x
U U U U
I I I I
,., r,
N x M x
a x ~'~'x ~ U
x iix'~ o z x
U x N '1 N N N o'~1x v"~~ M W
N x N U x f x x x x U x x x x
x x x
U U U ~ U U U U x x U U v U U U x U
u1 o u1 o u1 0
v-1 r1 N N N1

207~~86
N
dl
O
O
In O
O
O N
o~ O
N
y~
~U
C~
LL
O
N
riri'-Ir1r1 r-1r1r1r1w1riri r-Ir-Ir-1r1rar-Ir-Ir-Ir-1r-I
~ C ~ ~ ~ G f~~ G >~f~G ~ s~~
t~t~~ t~~ t~G 1 N ~ N N ~ N > N ~ QJN N N N
N ~ N N N N N N N
.,
H H H H H H H H H H H H H H H H H H H H H H
I I I t I 1 I I I I I I I I ~ I I I I
d,' t t I M M M M M M M M M M M M M M M M M M M
M M M
x x x x x x x x x x x x x x x x x x x x x x
N U U U U U U U U U U U U U U U U U U U U U U
>C O O O O O O O O O O O O O O O O O O O O O O
N x M M x
U " U O U U U ~ ~
. ~nu~ I
~ ~
h h t'~Oo0111U N N N N N x x ~ u'1
x x x x x ~ o ~ ~ V ~ ~
~ ~ ~ U U In , V
x N N U N (V x
U U U U U N N N N N x y 1
x x i , , I I x x x U x x x x x x .~ U
h U U ~ 1~w t~.i..1U U U ~ U U U U ~,U U U '-'U U
fx ~,~,
x x
U U
i t1
q x
x
U U
f CV
1 x
x
U U
I I
M r,
N x M x
v x ~ ~'v
x x a x = o z x x
' x M N N N M x
M x U N N N U N x x x x x U
x N I x x x x
P: U U x f~x x x U U U v U U U U x x U U ~~
o u1 0
v-1 ~ N N f'1

2~'~~~86
_,
N
0
N
o
II1 O
O
o N
o~ O
ro
o
u~
w
t~
v v
.~.~, r, r,r,
~ ~ ~ G G
. a ~ ?~ 7,
.~ : N v v G
I I ~ l ~I .~I.r.1v r.1,-I~-I~
r,v v
I I rir1d: .>:;~"..r15.,~,5r~ ? W,
0 0 ,1",,~1~ ~ J-~~,''I I I I I I
S-11~-I1~JJI I I .7..1N N N M M M
O O I I N t11t11I I I I I I I
r-ar-Ir1rir-1InN I I I u1~".,'S.,'G L; C:Lar-1r-i.-fr~r-I
.,,t'',.:~''1 I r-iO r1I v N v ~ N N ~ ~.,'r? Wr
.S'.r...S~'.U U O O '~ S1'JyO '~"~'~',.~',..~"'~".~.~.,rG'G'~-,~.
v N v w ~ ~ ~ ~ O .~~ .~.~.~.>~.>~.s~rororororo
riri -r1A A O O 1.1r1.l..)1J1.11.~1J1l 1~1-1f-1S-1~1S-1S-a
,fi'~, ~',I I S-1S~v ~."v r1N N N N N N ~
H E-~H m m .4,t~~ U ~ 2 f~t~t~~ ~ ~ f=.~
I I I - I I I I I I v v v v v v I I I I I
i4',M M M N N N VW''~N N N W ala1L~1alLYlN N N N N
U U U U a a U U U U U U
N U U U U U U U z z 2
>C O O v1O O O O O O O O O O U7O O U~O O u1O O
I
N
x
U
N
x I
N
M M r'~1M M M M M
r N x M M M M M M M M M M x x x x x x x x
x U x x x x x x x x x x
p; U x U U U U U U U U U U U U U U U U U U x x
x U
U O
N N
x x
U U
N N
x x
U U
I 1
x x x x x x x x x x x x x x x x x x x
P4 U U U U U U U U U U U U U U U U U U x U
u~ o u1 o u1 0
r1 r1 N N

2~'~~~8~
_,
N
0
0
m o
0
o N
o~ O
ro
roo
~a
w
~
N
N
r1 r1r-Ir-Ir1rir-1rir1r-Irir1r-Iri r-In-ir1r-yr1~ r-ir-I
t~ >~~ G A ~'>~ G ~ >~~ >~t~>~ ~ >~t;G:~ t~ ~
ro rorob rororo rororororororo ro rorob roro ro
~' ~ w w w ~
t~ w r~~ r~~ ~ ~ ~ ~ ~ ~ '~w w w w u
,
1 1 1 1 1 n 1 1 1 1 1 1 1 1 1
R,'1 1 1 1 1 1 1 N N N.N N N N N N N N N N N N
N N N N N N N
U U U U U
N U U U U U U V U U U U U U U U U U
x o 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
N x M fn x
~ U V ~ l
tUl
IIU N O ~ ~y i
,~
r r ~ o,rn o a x
x x x x x x a x -.U U z~ U ~ U U ui'y
U U U N
U U U U U N N N x N N W1 1 U C'~ts1',.(',x !'yt
x x x y
~ , , , i x x x U x x x ~,x x ~ U
n; U U ~ ~ w G ~ U U U v U U U U U U U ~ U U
c ci
x x
U U
~a
N x
x
U U
i
1
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205586
88 O.Z. 0050/42589
The herbicidal and growth-regulating compounds I according to the
invention, or agents containing them, may be applied for instance in the
form of directly sprayable solutions, powders, suspensions (including
high-percentage aqueous, oily or other suspensions), dispersions,
emulsions, oil dispersions, pastes, dusts, broadcasting agents, or
granules by spraying, atomizing, dusting, broadcasting or watering. The
forms of application depend entirely on the purpose for which the agents
are being used, but they must ensure as fine a distribution of the active
ingredients according to the invention as possible.
The compounds I are generally suitable for the preparation of solutions,
emulsions, pastes and oil dispersions to be sprayed direct. Examples of
inert additives are mineral oil fractions of medium to high boiling point,
such as kerosene or diesel oil, further coal-tar oils, and oils of vege-
table or animal origin, aliphatic, cyclic and aromatic hydrocarbons such
as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphtha-
lenes and their derivatives, methanol, ethanol, propanol, butanol, cyclo-
hexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly
polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide,
N-methylpyrrolidone, water, etc.
Aqueous formulations may be prepared from emulsion concentrates, pastes,
oil dispersions, wettable powders or water-dispersible granules by adding
water. To prepare emulsions, pastes and oil dispersions the ingredients as
such or dissolved in an oil or solvent may be homogenized in water by
means of wetting or dispersing agents, adherents or emulsifiers. concen-
trates which are suitable for dilution with water may be prepared from
active ingredient, wetting agent, adherent, emulsifying or dispersing
agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and
ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,
phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene-
sulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and
alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated
hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol
glycol ethers, condensation products of sulfonated naphthalene and
naphthalene derivatives with formaldehyde, condensation products of
naphthalene or naphthaienesulfonic acids with phenol and formaldehyde,
polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxyt-
ated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol
ethers, tributylphenyl polyglycot ethers, alkylaryl polyether alcohols,
isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene,
lauryl alcohol potyglycot ether acetal, sorbitol esters, lignin-sulfite
waste liquors and methyl cellulose.

20~5~86
89 O.Z. 0050/42589
Powders, dusts and broadcasting agents may be prepared by mixing or
grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be
prepared by bonding the active ingredients to solid carriers. Examples of
solid carriers are mineral earths such as silicic acids, silica gels,
silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,
loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium
sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium
sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable
products such as grain meals, bark meal, wood meal, and nutshell meal,
cellulosic powders, etc.
The formulations contain from 0.1 to 95, and preferably 0.5 to 90, ~o by
weight of active ingredient. The active ingredients are used in a purity
of 90 to 100, and preferably from 95 to 100, ~ (according to the NMR
spectrum).
The compounds I according to the invention may be formulated as follows:
I. 90 parts by weight of compound 1.001 is mixed with 10 parts by weight
of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for
application in the form of very fine drops.
II. 20 parts by weight of compound 1.001 is dissolved in a mixture
consisting of 80 parts by weight of xylene, 10 parts by weight of the
adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-
monoethanolamide, 5 parts by weight of the calcium salt of dodecyibenzene-
sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene
oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts
by weight of water and uniformly distributing it therein, an aqueous dis-
persion is obtained containing 0.02 by weight of the active ingredient.
III. 20 parts by weight of compound 1.002 is dissolved in a mixture
consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of
isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide
' and I mole of isooctylphenal, and 10 parts by weight of the adduct of
moles of ethylene oxide and 1 mole of castor oil. By pouring the
solution into 100,000 parts by weight of water and finely distributing it
40 therein, an aqueous dispersion is obtained containing 0.02~o by weight of
the active ingredient.

~07~~86
90 0.z. 0050/42589
IV. 20 parts by weight of compound 1.002 is dissolved in a mixture
consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a
mineral oil fraction having a boiling point between 210 and 280°C, and
parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole
5 of castor oil. By pouring the solution into 100,000 parts by weight of
water and uniformly distributing it therein, an aqueous dispersion is
obtained containing 0.02% by weight of the active ingredient.
V. 20 parts by weight of compound 1.001 is well mixed with 3 parts by
10 weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid,
17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained
from a sulfite waste liquor, and 60 parts by weight of powdered silica
gel, and triturated in a hammer mill. By uniformly distributing the
mixture in 20,000 parts by weight of water, a spray liquor is obtained
containing 0.1% by weight of the active ingredient.
VI. 3 parts by weight of compound 1.001 is intimately mixed with 97 parts
by weight of particulate kaolin. A dust is obtained containing 3Mo by
weight of the active ingredient.
VII. 30 parts by weight of compound 1.002 is intimately mixed with a
mixture consisting of 92 parts by weight of powdered silica gel and
8 parts by weight of paraffin oil which has been sprayed onto the surface
of this silica gel. A formulation of the active ingredient is obtained
having good adherence.
VIII. 20 parts by weight of compound 1.002 is intimately mixed with
2 parts of the calcium salt of dodecytbenzenesulfonic acid, 8 parts of a
fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenoi-
sulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic
mineral oil. A stable oily dispersion is obtained.
The active ingrediehts or the herbicidal and growth-regulating agents
containing them may be applied pre- or postemergence. If certain crop
plants tolerate the active ingredients less well, application techniques
may be used in which the herbicidal agents are sprayed from suitable
equipment in such a manner that the leaves of sensitive crap plants are if
possible not touched, and the agents reach the soil or the unwanted plants
growing beneath the crop plants (post-directed, lay-by treatment).
The application rates depend on the objective to be achieved, the time of
the year, the plants to be combated and their growth stage, and are from
0.001 to 3, preferably 0.005 to 0.5, kg of active ingredient per hectare.

zo~~~~~
91 O.Z. 0050/42589
The growth-regulating salicylic acid derivatives of the formula I may
exercise a variety of influences on practically all plant development
stages, and are therefore used as growth regulators. The diversity of
action of growth regulators depends especially on
a) the type and variety of plant;
b) the time applied, with reference to the development stage of the
plants and the time of the year;
c) the place and method of application (seed treatment, soil treatment,
application to foliage, or injection into tree trunks);
d) climatic factors, e.g., average temperature, amount of precipitation,
day length and light intensity);
e) soil conditions (including fertilization);
f) the formulation of the active ingredient; and
g) the concentration at which the active ingredient is applied.
The active ingredients I according to the invention may be applied not
only to the seed (as a dressing), but also to the soil, i.e., via the
roots, and to the foliage by spraying.
As a result of the good tolerance by crop plants, the application rate
when the active ingredients are used as growth regulators may vary within
wide limits.
When the active ingredients are used for treating seed, amounts of from
0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are general-
ly required. For foliage and soil treatment, amounts of from 0.001 to 10,
preferably from 0.01 to 3, and especially from 0.01 to 0.5, kg/ha are
generally considered to be sufficient.
The active ingredients or the herbicidal agents containing them may be
applied pre- or postemergence. If certain crop plants tolerate the active
ingredients less well, application techniques may be used in which the
that the leaves of sensitive crop plants are if possible not touched, and
the agents reach the soil or the unwanted plants growing beneath the crop
plants (post-directed, lay-by treatment).
The application rates depend on the objective to be achieved, the time of
the year, the plants to be combated and their growth stage, and are from
0.001 to 3, preferably 0.15 to 1.0, kg of active ingredient per hectare.
In view of the many application methods possible, the compounds according
to the invention, or agents containing them, may be used in a further
number of crop plants for removing unwanted plant growth. The following
crops are given by way of example:

20~~~86
92 O.z. 0050/42589
Botanical name Common name
Ailium cepa onions
Ananas comosus pineapples
Arachis hypogaea peanuts (groundnuts)
Asparagus officinalis asparagus
Avena sativa oats
Beta vulgaris spp. altissima sugarbeets
Beta vulgaris spp. rapa fodder beets
Beta vulgaris spp. escutenta table beets, red beets
10Brassica napus var. napus rapeseed
Brassica napus var. napobrassicaswedes
Brassica napus var. rapa turnips
Brassica rapa var. silvestris
Camellia sinensis tea plants
15Carthamus tinctorius safflower
Carya illinoinensis pecan trees
Citrus limon lemons
Citrus maxima grapefruits
Citrus reticulata mandarins
20Citrus sinensis orange trees
Coffea arabica (Coffea canephora,
Coffea liberica) coffee plants
Cucumis melo melons
Cucumis sativus cucumbers
25 Cynodon dactylon Bermudagrass
Daucus carota carrots
Etais guineensis oil palms
Fragaria vesca strawberries
Giycine max soybeans
30 Gossypium hirsutum (Gossypium
arboreum,
Gossypium herbaceum, Gossypium vitifolium)cotton
Helianthus annuus sunflowers
Helianthus tuberoses Jerusalem artichoke
Hevea brasiliensis rubber plants
35 Hordeum vulgare barley
Humulus lupulus hops
Ipomoea batatas sweet potatoes
Juglans regia walnut trees
Lactuca sativa lettuce
40 Lens culinaris lentils
Linum usitatissimum flax
Lycopersicon lycopersicum tomatoes
Males spp. apple trees
Manihot escutenta cassava
Medicago sativa alfalfa (lucerne)

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93 0.1. 0050/42589
Botanical name Common name
Menthe piperita peppermint
Muss spp. banana plants
Nicotiana tabacum (N. rustics) tobacco
Olea europaea olive trees
Oryza sativa rice
Panicum miliaceum millet
Phaseolus lunatus limabeans
Phaseolus mungo mungbeans
10Phaseolus vulgaris snapbeans, green beans,
dry beans
Pennisetum glaucum pearl millet
Petroselinum crispum spp. tuberosumparsley
Picea abies Norway spruce
15Abies albs fir trees
Pinus spp. pine trees
Pisum sativum English peas
Prunus avium cherry trees
Prunus domestics plum trees
20Prunus dulcis almond trees
Prunus persica peach trees
Pyrus communis pear trees
Ribes sylvestre redcurrants
Ribes uva-crisps gooseberries
25Ricinus communis castor-oii plants
Saccharum officinarum sugar cane
Secale cereale rye
Sesamum indicum sesame
Solanum tuberosum Irish potatoes
30Sorghum bicolor (s. vulgare) sorghum
Sorghum dochna sorgo
Spinacia oleracea spinach
Theobroma cacao cacao plants
Trifolium pretense red clover
35Triticum aestivum wheat
Triticum durum durum wheat
vaccinium corymbosum blueberries
vaccinium vitas-idaea cranberries
Vicia faba tick beans
40vigna sinensis (v. unguiculata}cow peas
vitas vinifera grapes
Zea mays Indian corn, sweet corn,
maize

~0~5~8~
94 O.Z. 0050/42589
The compounds of the formula I are of particular interest for controlling
a large number of fungi in various crops, especially wheat, rye, barley,
oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane,
fruit and ornamentals in horticulture and viticulture, and in vegetables
such as cucumbers, beans and cucurbits, and in the seeds of these plants.
The novel compounds are particularly useful for controlling the following
plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia solani in cotton,
Ustilago species in cereals and sugar cane,
Venturia inaequalis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The compounds are applied by treating the fungi or the plants, seeds or
materials to be protected against fungus attack, or the soil with a fungi
cidatly effective amount of the active ingredients. They may be applied
before or after infection of the materials, plants or seeds by the fungi.
The fungicidal agents generally contain from 0.1 to 95, and preferably
from 0.5 to 90, wt% of active ingredient.
' Depending on the type of effect desired, application rates vary from 0.02
to 3 kg of active ingredient per hectare. The novel compounds may also be
used for protecting materials (timber), e.g., against Paecilomyces
variotii.
For treating seed, active ingredient amounts of from 0.001 to 50, and
preferably fromØ01 to 10, g per kg of seed are generally sufficient.

2~~5~8~
95 O.Z. 0050/42589
The agents, or the ready-to-use formulations prepared therefrom, such as
solutions, emulsions, suspensions, powders, dusts, pastes or granules, are
applied in known manner, for example by spraying, atomizing, dusting,
scattering, treating seed, or by watering.
To increase the spectrum of action and to achieve synergistic effects, the
compounds I may be mixed with each other, or mixed and applied together
with numerous representatives of other herbicidal or growth-regulating
active ingredient groups. Examples of suitable components are diazines,
4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines,
N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines,
amides, ureas, Biphenyl ethers, triazinones, uracils, benzofuran deriva-
tives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, (het-
ero)-aryloxyphenoxypropionic acids and salts, esters, amides 'thereof, etc.
It may also be useful to apply the compounds I, either alone or in
combination with other herbicides, in admixture with other crop protection
agents, e.g., agents for combating pests or phytopathogenic fungi or
bacteria. The compounds may also be mixed with solutions of mineral salts
used to remedy nutritional or trace element deficiencies. Non-phytotoxic
oils and oil concentrates may also be added.
Synthesis instructions
Example 1
General instructions for the preparation of aromatic carboxylic acid
hydroxylamine esters or similar compounds of the formula I:
3.2 mmol of sodium hydride is added to a mixture of 3.2 mmol of the
aromatic 2-(4,6-dimethoxypyrimidin-2-yl)-oxycarboxylic acid concerned in
20 ml of dimethoxyethane; gas immediately evolves. The mixture is stirred
for 1 hour at room temperature and then cooled to 0°C, and 3.5 mmot of
oxalyl chloride is added. The mixture is stirred for 1 hour at 0°G, and
about 30~ of the solvent is evaporated under reduced pressure to remove
excess oxalyl chloride. A solution of 4.2 mmol of the hydroxylamine in
question or a comparable hydroxy compound in 10 ml of dimethoxyethane is
added, followed by 3.2 mmol of pyridine, at 0°C, and the mixture is
heated
over a period of about 1 hour to room temperature. It is poured into
120 ml of cold water and extracted with methylene chloride. The organic
phase is dried over sodium sulfate and evaporated down under reduced
pressure. The substance which remains can be further purified by chromato-
graphy on silica gel.

20~5~86
96 O.Z. 0050/42589
Example 2
General instructions for the preparation of aromatic carboxylic acid
hydroxylamine esters or similar compounds of the formula I:
1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of
mmol of the corresponding 6-hetaryl-2-(4,6-dimethoxypyrimidin-2-yloxy)-
benzoic acid in 30 ml of tetrahydrofuran. After the mixture has been
stirred for 30 minutes at room temperature, 9.9 mmol of the corresponding
10 hydroxy compound is added and the whole is stirred for a further 14 hours.
The reaction mixture is then hydrolyzed with 300 ml of 1N phosphoric acid
and the resulting mixture is extracted several times with methyl
tert-butyl ether. The organic phases are dried over sodium sulfate and
evaporated down under reduced pressure. The residue can be further
purified by column chromatography or recrystallization.
Example 3
General instructions for the preparation of aromatic carboxylic acid
hydroxylamine esters or similar compounds of the formula I:
1.75 g (10.8 mmoi) of N,N'-carbonylbisimidazole is added to a solution of
10 mmol of the corresponding 6-hetarylsalicylic acid in 30 ml of dioxane.
After the mixture has been stirred for 30 minutes at room temperature, 9.9
mmol of the corresponding hydroxy compound is added and the whole is
stirred for a further 14 hours. The batch is then hydrolyzed with 300 ml
of 1N phosphoric acid, and the resulting mixture is extracted several
times with methyl tert-butyl ether. The organic phases are combined, dried
over sodium sulfate and evaporated down under reduced pressure. The
residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium
hydride (85% in paraffin, 10 mmol) is added. After the mixture has been
stirred for 30 minutes at room temperature, 1.97 g (9 mmol) of 4,6-di-
methoxy-2-methylsulfonylpyrimidine is added and the mixture is stirred for
14 hours. the reaction mixture is poured into 300 m1 of O.1N phosphoric
acid and extracted with diethyl ether. The ether phase is dried over
Sodium sulfate and evaporated down, and the residue is purified by column
chromatography or recrystallization.
Example 4
General instructions for the preparation of aromatic carboxylic acid
hydroxylamine esters or similar compounds of the formula I:
At 10°C, 0.46 g (0.015 mol) of sodium hydride (80% strength) is
added to a
solution of 15 mmol of azolyl 6-hetarylsalicylate in 25 ml of anhydrous

20~~~~~
97 O.Z. 0050/42589
dimethylformamide, and the mixture is stirred for 3 hours at 30°C. 3.27
g
(0.015 mot) of 2-methylsulfonyl-4,6-dimethoxypyrimidine is added and the
mixture is stirred for 12 hours at room temperature. It is then introduced
into 500 ml of water to which 2.5 ml of orthophosphoric acid has previous-
1y been added. The oil which separates out is taken up in ethyl acetate
and dried over sodium sulfate. The greasy residue remaining after
evaporation is purified by column chromatography or recrystallization.
Example 5
6-Pyrazolyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-I-(N,N-dimethylaminooxy-
carbonyl)-benzene
At 10°C, 0.30 g (0.01 mol) of sodium hydride (80% strength) is
added to a
solution of 2.47 g (10 mmol) of 3-pyraaolyl-2-(N,N-dimethylaminooxycarbon-
y1)-phenol in 25 ml of anhydrous dimethylformamide, and the reaction
mixture is stirred for 3 hours at 30°C. 2.18 g (0.01 mot) of 2-methyl-
sulfonyl-4,6-dimethoxypyrimidine is added and the mixture is stirred for
12 hours at room temperature. The reaction mixture is introduced into
500 m1 of water to which 2.5 ml of orthophosphoric acid has previously
been added. The oil which separates out is taken up in ethyl acetate and
dried over sodium sulfate. The greasy residue remaining after evaporation
is purified to give a colorless solid.
Example 6
6-(2-Thienyl)-2-(4,6-dimethoxypyrimidin-2-yloxy)-1-(N,N-dimethylaminooxy-
carbonyt)-benzene
3.2 mmol of sodium hydride is added to a mixture of 1.14 g (3.2 mmol) of
6-(2-thienyl)-2-(4,6-dimethoxypyrimidin-2-yl)-benzoic acid in 20 ml of
dimethoxyethane, whereupon a gas immediately evolves. The mixture is
stirred for 1 hour at room temperature and cooled to 0°C, and 3.5 mmol
of
oxalyl chloride is added. The mixture is stirred for 1 hour at 0°C,
after
which about 30% of the solvent is evaporated under reduced pressure to
remove excess oxalyl chloride. A solution of 4.2 mmol of N,N-dimethyl-
hydroxylamine in 10 ml of dimethoxyethane (from 230 mg of N,N-dimethyl-
hydroxylamine hydrochloride and 332 g of pyridine) is then added, followed
by 3.2 mmol of pyridine at 0°C, and the mixture is heated over a period
of
1 hour to room temperature. The mixture is poured into 120 ml of cold
water and extracted with methylene chloride. The organic phase is dried
over sodium sulfate and evaporated down under reduced pressure. The oil
which remains is further purified by chromatography on silica gel.

207~~~6
98 O.Z. 0050/42589
Example 7
6-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxy-
carbonylJ-benzene
1.75 g (10.8 mmol) of N,N'-carbonylbisimidazole is added to a solution of
1.88 g (10 mmoi), of 6-imidazolylsalicylic acid in 30 ml of tetrahydro-
furan. After the mixture has been stirred for 30 minutes at room tempera-
ture, 9.9 mmol ~of N-hydroxypyrazole is added and the mixture is stirred
for a further 14 hours. The reaction mixture is then hydrolyzed with
300 ml of 1N phosphoric acid and the resulting mixture is extracted
several times with methyl tert-butyl ether. The organic phases are dried
over sodium sulfate and evaporated down under reduced presssure. The
residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium
hydride (85% strength in paraffin, 10 mmoi) is added. After the mixture
has been stirred for 30 minutes at room temperature, 1.58 g (9 mmol) of
1-chloro-3,5-dimethoxy-s-triazine is added and the whole is stirred for 14
hours. The batch is introduced into 300 ml of O.1N phosphoric acid, and
extracted with diethyl ether. The ether phase is dried over sodium
sulfate and evaporated down, and the residue is purified by column
chromatography.
Example 8
6-(2-Thienyl)-2-(4,6-dimethoxytriazin-2-yloxy)-1-(N,N-dimethylaminooxy-
carbonyl)-benaene
4.4 g (20 mmol) of 6-(2-thienyl)-salicyclic acid is dissolved in 30 ml of
thionyl chloride, and refluxed for 90 minutes. After the reaction mixture
has cooled it is evaporated down. Toluene is added twice (100 ml each
time) to remove the thionyi chloride, followed by evaporation. The residue
is dissolved in 50 ml of toluene, and a solution of N,N-dimethylhydroxyl-
amine (from 6.85 g of N,N-dimethylhydroxytamine hydrochloride, 15 g of
potassium carbonate and 30 m1 of toluene) is added; the mixture is stirred
for 14 hours at room temperature. The solution is introduced into a
mixture of 150 m1 of water and 4.5 g of orthophosphoric acid, the mixture
is extracted with ethyl acetate, and the combined organic phases are
washed with water and saturated sodium chloride solution, dried over
sodium sulfate and evaporated down. After drying using an oil pump there
remains 5 g of a colorless oil, which is dissolved in 50 ml of DMF and to
which 0.64 g of sodium hydride (85 % strength) is added. After the mixture
has been stirred for 30 minutes, 3.67 g (21 mmol) of chiorodimethoxy-
triazine is added and the whole is heated for 2 hours at 50oC. The
solution is poured into 400 ml of water/5 ml of orthophosphoric acid,
extracted with ethyl acetate, dried over sodium sulfate, evaporated down

~0~558~
99 O.Z. 0050/42589
and chromatographed on silica gel. There is obtained 2.2 g of the product
as a colorless viscous oil. 1N-NMR in CDC1~, 270 MHz, d in ppm: 2.58
(s, 6H), 3.99 (s, 6H), 7.0-7.6 (m, 6H) (active ingredient no. 1.002).
The structures given in the Tables 1 and 2 below describe particularly
preferred active ingredients of the formula I, and may be prepared - with
appropriate modifications of the starting materials - in accordance with
the foregoing synthesis examples.
15
25
35

207~~8~
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20~5~~6
a
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O.z. 00501~~~
102
Use examples
The herbicidal action of salicylic (thio)ether derivatives
of the formula I is demonstrated in greenhouse experiments:
The vessels employed were plastic flowerpots having a volume
of 300 cm3 and filled with a sandy loam containing about
3.0~ humus. The seeds of the test plants were sown sepa-
rately, according to species.
For the preemergence treatment, the formulated active
ingredients were applied to the surface of the soil immedi-
ately after the seeds had been sown. The compounds were
emulsified or suspended in water as vehicle, and sprayed
through finely distributing nozzles.
After the agents had been applied, the vessels were lightly
sprinkler-irrigated to induce germination and growth.
Transparent plastic covers were then placed on the vessels
until the plants had taken root. The cover ensured uniform
germination of the plants, insofar as this was not impaired
by the active ingredients.
For the postemergence treatment, plants were used which had
been sown in the pots and grown there, or they were grown
separately as seedlings and transplanted to the pots a few
days before treatment. The plants were grown, depending on
growth form, to a height of 3 to 1S cm before being treated
with the compounds, suspended or emulsified in water. The
application rate for postemergence treatment was 0.5 kg/ha.
The pots were set up in the greenhouse, heat-loving species
at from 20 to 3SaC, and species from moderate climates at
from 10 to 25°C. The experiments were run for from 2 to
A weeks. During this period the plants were tended and their
reactions to the various treatments assessed. The assessment
scale was 0 to 100, 100 denoting nonemergence or complete
destruction of at least the visible plant parts, and 0 de-
noting no damage or normal growth.

O.Z. 0050/42589
2o~~~s~
103
xhe plants used in the greenhouse experiments were Echinoch-
'.loa crus-galli, Galium aparine and Centaurea cyanus.
Active ingredients 1.001 and 1.002, applied postemergence at
a rate of 0.05 kg/ha, give excellent control of unwanted
plants.
15
25
35

Dessin représentatif