Indian Patents
Title of Invention

"2,4-DIHALOGEN-6-(C2-C3-ALKYL) PHENYL SUBSTITUTED TETRAMIC ACID DERIVATIVES"
Abstract The invention relates to novel 2,4-dihalo-6-(C2-C3-alky!)phenyl-substituted tetramic acid derivatives of the formula (I), in which A, B, D, G, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly the 2,4-dihak>6-(C2-C3-alkyl)phenyl-substituted tetramic acid derivatives and secondly a crop plant compatibility-improving compound.
Full Text 2,4-Dihalogen-6-(C7-Cyalkyl)phenyl substituted tetramic acid derivatives
The invention relates to novel 2,4-dihalo-6-(C2-C3-alkyl)phenyl-substituted tetramic acid derivatives, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides. The invention also relates to selective herbicidal compositions comprising firstly the 2,4-dihalo-6-(C2-C3-alkyl)phenyl-substituted tetramic acid derivatives and secondly at least one crop plant compatibility-improving compound.
3-Acylpyrrolidine-2,4-diones are described as having pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenylpyrrolidine-2,4-diones were synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985,1095). A biological activity of these compounds has not been described.
EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of a similar structure (3-aryl-pyrrolidine-2,4-diones); however, a herbicidal, insecticidal or acaricidal action of these compounds has hitherto not been described. Unsubstituted bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) having herbicidal, insecticidal or acaricidal action are known.
Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and IH-arylpyrrolidinedione derivatives (EP-A-456 063, EP-A-521334, EP-A-596298, EP-A-613884, EP-A-613 885, WO 94/01 997, WO 93/26954, WO 95/20 572, EP-A 0 668 267, WO 96/25 395, WO 96/31023, WO 96/35 664, WO 97/01535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/09092, WO 01/17972, WO 01/23354 and WO 01/74770).
However, in particular at low application rates and concentrations, the activity and the activity spectrum of these compounds are not always entirely satisfactory. Moreover, the compatibility of these compounds with plants is not always sufficient.
This invention now provides novel compounds of the formula (I)


in which
X represents halogen,
Y represents halogen and
Z represents ethyl or n-propyl,
and, if
G represents hydrogen (a), then
A represents hydrogen, represents in each case optionally substituted alkyl, cycloalkyl or alkoxyalkyl,
B represents hydrogen, alkyl or alkoxyalkyl or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated Cs-Cg-ring which is optionally substituted by alkyl or haloalkyl,
D represents hydrogen or represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and optionally substituted cycloalkyl, or
A and D together with the atoms to which they are attached represent an unsubstituted or substituted cycle which is saturated or unsaturated and optionally contains at least one heteroatom in the A,D-moiety,
and,if
G represents one of the groups
(Formula Remove)
in which
E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, then
R1 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxy-alkyl, alkylthioalkyl or polyalkoxyalkyl or represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl or represents in each case optionally substituted phenyl or hetaryl,
R2 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxy-alkyl or polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R3, R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R6 and R7 independently of one another represent hydrogen, represent in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are attached represent an optionally substituted cycle which optionally contains oxygen or sulfur,
A represents hydrogen, represents in each case optionally halogen-substituted

alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl or represents optionally substituted cycloalkyl,
B represents hydrogen, alkyl or alkoxyalkyl or
A and B together with the carbon atom to which they are attached represent an unsubstituted or substituted cycle which is saturated or unsaturated and optionally contains at least one heteroatom,
D represents hydrogen or represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, or optionally substituted cycloalkyl, or
A and D together with the atoms to which they are attached represent an unsubstituted or substituted cycle which is saturated or unsaturated and optionally contains at least one heteroatom in the A,D-moiety.
Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition, which, if desired, can be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and compositions comprising them. However, for the sake of simplicity, hereinbelow only compounds of the formula (I) are referred to, although what is meant are both the pure compounds and, if appropriate, mixtures having varying proportions of isomeric compounds.
Including the different meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following principal structures (I-a) to (I-g) result:
(FigureRemove)

in which
R4, R5, R6 and R7 are as defined above.

Furthermore, it has been found that the novel compounds of the formula (I) are obtained by one of the processes described below:
(A) Compounds of the formula (I-a),
(FigureRemove)
in which
A, B, D, X, Y and Z are as defined above
are obtained when
compounds of the formula (D)
(FigureRemove)
in which
A, B, D, X, Y and Z are as defined above
and
R8 represents alkyl (preferably Ci-Ce-alkyl)
are condensed intramolecularly in the presence of a diluent and in the presence of a base.
(B) Compounds of the formula (I-b) shown above in which A, B, D, R1, X, Y and Z are as defined above are obtained when compounds of the formula (I-a) shown above in
which A, B, D, X, Y and Z are as defined above, where A may also represent in each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together with the carbon atom to which they are attached may also represent Ca-g-cycloalkyl which is substituted by Q-Ce-alkoxy or interrupted by at least one heteroatom (WO 967 35 664) are reacted
a) with acid halides of the formula (IE),
^. T
0 on)
in which
R1 is as defined above and
Hal represents halogen (in particular chlorine or bromine) or B) with carboxylic anhydrides of the formula (TV),
R'-CO-O-CO-R1 (IV)
in which R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
(C) Compounds of the formula (I-c) shown above in which A, B, D, R2, M, X, Y and Z are as defined above and L represents oxygen are obtained when compounds of the formula (I-a) shown above in which A, B, D, X, Y and Z are as defined above, where A may also represent in each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together with the carbon atom to which they are attached may also represent Cs-g-cycloalkyl which is substituted by Ci-Ce-alkoxy or interrupted by at least one heteroatom, are in each case reacted
with chloroformic esters or chloro formic thioesters of the formula (V),
R2-M-CO-C1 (V)
in which
R2 and M are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
(D) Compounds of the formula (I-c) shown above in which A, B, D, R^, M, X, Y and Z are as defined above and L represents sulfur are obtained when compounds of the formula (I-a) shown above in which A, B, D, X, Y and Z are as defined above, where A may also represent in each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together with the carbon atom to which they are attached may also represent Ca-g-cycloalkyl which is substituted by Ci-Ce-alkoxy or interrupted by at least one heteroatom, are in each case
a) reacted with chloromonothioformic esters or chlorodithioformic esters of the formula (VI)
in which
M and R2 are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid
binder,
or
6) are reacted with carbon disulfide and then with compounds of the formula (VII)
R2-Hal (VII)
in which
R2 is as defined above and
Hal represents chlorine, bromine or iodine,
if appropriate in the presence of a diluent and if appropriate in the presence of a base.
(E) Compounds of the formula (I-d) shown above in which A, B, D, R.3, X, Y and Z are
as defined above are obtained when compounds of the formula (I-a) shown above in
which A, B, D, X, Y and Z are as defined above, where A may also represent in each
case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together
with the carbon atom to which they are attached may also represent Cs-g-cycloalkyl
which is substituted by Ci-Ce-alkoxy or interrupted by at least one heteroatom, are in
each case reacted
with sulfonyl chlorides of the formula (VIII)
R3-SO2-C1 (Vffl)
in which R3 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
(F) Compounds of the formula (I-e) shown above in which A, B, D, L, R4, R5, X, Y and Z
are as defined above are obtained when compounds of the formula (I-a) shown above
in which A, B, D, X, Y and Z are as defined above, where A may also represent in
each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B
together with the carbon atom to which they are attached may also represent Cs-g-
cycloalkyl which is substituted by Q-Ce-alkoxy or interrupted by at least one
heteroatom, are in each case reacted
with phosphorus compounds of the formula (IX)
R4 /
Hal-P
N^_5
L R (IX)
in which

L, R and R are as defined above and
Hal represents halogen (in particular chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
(G) Compounds of the formula (I-f) shown above in which A, B, D, E, X, Y and Z are as defined above are obtained when compounds of the formulae (I-a) in which A, B, D, X, Y and Z are as defined above, where A may also represent in each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together with the carbon atom to which they are attached may also represent Ca-g-cycloalkyl which is substituted by Q-Ce-alkoxy or interrupted by at least one heteroatom, are in each case reacted
with metal compounds or amines of the formulae (X) and (XI), respectively
RV"
Me(OR10)t (X) R12 (XI)
in which
Me represents a mono- or divalent metal (preferably an alkali metal or alkaline earth metal, such as lithium, sodium, potassium, magnesium or calcium),
t represents the number 1 or 2 and
R10, R11, R12 independently of one another represent hydrogen or alkyl (preferably C]-C8-alkyl)>
if appropriate in the presence of a diluent.
(H) Compounds of the formula (I-g) shown above in which A, B, D, L, R6, R7, X, Y and Z are as defined above are obtained when compounds of the formula (I-a) shown above in which A, B, D, X, Y and Z are as defined above, where A may also represent in each case optionally halogen-substituted alkenyl or alkylthioalkyl and A and B together with the carbon atom to which they are attached may also represent Cs-g-cycloalkyl which is substituted by Ci-Ce-alkoxy or interrupted by at least one

heteroatom, are in each case 1 a) reacted with isocyanates or isothiocyanates of the formula (XII)
R6-N=C=L (XII)
in which R6 and L are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or
B) reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XIII)
(FormulaRemove)
in which
L, R6 and R7 are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Furthermore, it has been found that the novel compounds of the formula (I) and also some compounds of the formula (I-a) additionally listed below as component b' are highly active pesticides, preferably insecticides and/or acaricides, and/or herbicides.
Surprisingly, it has now been found that certain substituted cyclic ketoenols, when used together with the crop plant compatibility-improving compounds (safeners/antidotes) described below, are highly suitable for preventing damage to the crop plants and can be used particularly advantageously as broad-spectrum effective combination preparations for the selective control of unwanted plants in crops of useful plants, such as, for example, in cereals, but also in corn, soybeans and rice.
The invention also provides selective herbicidal compositions comprising an effective amount of a combination of active compounds comprising, as components,

a1) at least one substituted cyclic ketoenol of the formula (I) in which A, B, D, X, Y, Z and G are as defined above
or
b') at least one substituted cyclic ketoenol of the formula (I-a) in which A and B together with the carbon atom to which they are attached represent saturated Ce-cycloalkyl which is substituted by methoxy, ethoxy, propoxy, butoxy or isobutoxy or represent saturated C6-cycloalkyl in which one methylene group is replaced by oxygen (DE-A-10 146 910) and
(c1) at least one crop plant compatibility-improving compound from the following group of compounds:
4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660), 1-dichloroacetyl-
hexahydro-3,3,8a-trimethylpyrrolo[l,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138),
4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1 -methylhexyl
5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl - cf. also related compounds in
EP-A-86750, EP-A-94349, EP-A-191736, EP-A-492366), 3-(2-chlorobenzyl)-l-(l-methyl-
l-phenylethyl)urea (cumyluron), a-(cyanomethoximino)phenylacetonitrile (cyometrinil),
2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
1-(1-methyl-l-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-
2-methoxybenzoic acid (dicamba), S-1-methyl 1-phenyl ethyl piperidine-1-thiocarboxylate
(dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)-
acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), 4,6-dichloro-2-phenyIpyrimidine (fenclorim), ethyl l-(2,4-dichlorophenyl)-5-trichloro-methyl-lH-l,2,4-triazole-3-carboxylate (fenchlorazole-ethyl - cf. also related compounds in EP-A-174562 and EP-A-346620), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(l ,3-dioxolan-2-ylmethoxy)-a-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl — cf. also related compounds in WO-A-95/07897), l-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl l-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-lH-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl - cf. also related compounds in WO-A-
91/07874), 2-dichloromethyl-2-methyl-l,3-dioxolane (MG-191), 2-propenyl l-oxa-4-
azaspiro[4.5]decane~4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a-(l,3-
dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(l ,3-dioxolan-
2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxa-
zolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-
tolyl)butyric acid, 4-(4-chJorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl
diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl l-(2-chlorophenyl)-5-
phenyl-1 H-pyrazole-3-carboxylate, ethyl 1 -(2,4-dichlorophenyl)-5-methyl-1 H-pyrazole-3-
carboxylate, ethyl l-(2,4-dichlorophenyl)-5-isopropyl-lH-pyrazole-3-carboxylate, ethyl 1-
(2,4-dichlorophenyl)-5-( 1,1 -dimethylethyl)-1 H-pyrazole-3-carboxylate, ethyl 1 -(2,4-
dichlorophenyl)-5-phenyl-lH-pyrazole-3-carboxylate (cf. also related compounds in EP-A-
269806 and EP-A-333131), ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl
5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-
3-carboxylate (cf. also related compounds in WO-A-91/08202), 1,3-dimethylbut-l-yl
5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,
l-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-
oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate,
2-oxoprop-l-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,
diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate (cf.
also related compounds in EP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415,
cf. EP-A-613618), 4-chlorophenoxyacetic acid, 3,3'-dimethyl-4-methoxybenzophenone,
1 -bromo-4-chloromethylsulfonylbenzene, 1 - [4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-
methylurea (also known as N-(2-rnethoxybenzoyl)-4-[(methylaminocarbonyl)-
amino]benzenesulfonamide), l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-di-
methylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
l-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,
and/or one of the following compounds, defined by general formulae, of the general formula (Ha)


(Ha)

or of the general formula (lib)
(FormulaRemove)



or of the formula (He)
(FigureRemove)

¥ (He)
R18
where
n represents a number between 0 and 5,
A1 represents one of the divalent heterocyclic groupings shown below,
(FigureRemove)

R19
n represents a number between 0 and 5,
A represents optionally Ci-C4-alkyl- and/or Ci-C4-alkoxycarbonyl-substituted alkane-diyl having 1 or 2 carbon atoms,
R14 represents hydroxyl, mercapto, amino, Q-Ce-alkoxy, Ci-Ce-alkylthio, Ci-( amino or di-(Ci-C4-alkyl)amino,
R15 represents hydroxyl, mercapto, amino, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-( amino or di-(Ci-C4-alkyl)amino,
R16 represents in each case optionally fluorine-, chlorine- and/or bromine-substituted d-C4-alkyl,
R17 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, dioxolanyl-Ci-C4-alkyl, furyl, furyl-Ci-C4-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or Ci-C4-alkyl-substituted phenyl,
R18 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, Ci-C4-alkoxy-d-C4-alkyl, dioxolanyl-C]-C4-alkyl, furyl, furyl-Ci-C4-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or Ci-C4-alkyl-substituted phenyl, or together with R17 represents Cs-Ce-alkanediyl or C2-Cs-oxaalkanediyl, each of which is optionally substituted by Ci-C4-alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,
R19 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted Ci-C4-alkyl, Cs-Ce-cycloalkyl or phenyl,
R20 represents hydrogen or in each case optionally hydroxyl-, cyano-, halogen- or Q-C4-alkoxy-substituted Ci-Cs-alkyl, Ca-Ce-cycloalkyl or tri(Ci-C4-alkyl)silyl,
R21 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted Ci-C4-alkyl, Cs-Ce-cycloalkyl or phenyl,
X1 represents nitro, cyano, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or C i -C4-haloalkoxy,
X2 represents hydrogen, cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Q-C4-alkoxy or Ci-C4-haloalkoxy,
X3 represents hydrogen, cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Q-C4-alkoxy or Ci-C4-haloalkoxy,
and/or the following compounds, defined by general formulae, of the general formula (lid)

(FigureRemove)

or of the general formula (He)

(Figure Remove)
R
(He)

where
n represents a number between 0 and 5,

>22
R represents hydrogen or Ci-C4-alkyl,

>23
R represents hydrogen or Ci-C4-alkyl,

24
25
26
R
R
R

represents hydrogen, in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted Ci-Ce-alkyl, Q-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Cs-alkylamino or di-(Ci-C4-alkyl)amino, or in each case optionally cyano-, halogen- or Ci-C4-alkyl-substituted Cs-Ce-cycloalkyl, Ca-Ce-cycloalkyloxy, Cs-Ce-cycloalkylthio or Ca-Ce-cycloalkylamino,
represents hydrogen, optionally cyano-, hydroxyl-, halogen- or Ci-C4-alkoxy-substituted Ci-Ce-alkyl, in each case optionally cyano- or halogen-substituted Ca-Cg-alkenyl or Cs-Ce-alkynyl, or optionally cyano-, halogen- or Ci-C4-alkyl-substituted Ca-Cg-cycloalkyl,
represents hydrogen, optionally cyano-, hydroxyl-, halogen- or Ci-C4-alkoxy-substituted Ci-Cg-alk)'!, in each case optionally cyano- or halogen-substituted Ca-Ce-alkenyl or Cs-Ce-alkynyl, optionally cyano-, halogen- or Ci-C4-alkyl-substituted Cs-Ce-cycloalkyl, or optionally nitro-, cyano-, halogen-, Ci-C4-alkyl-, Ci-C4-halo-

alkyl-, Ci-C4-alkoxy- or Ci-C4-haloalkoxy-substituted phenyl, or together with R25 represents in each case optionally Ci-C4-alkyl-substituted Ca-Ce-alkanediyl or Ca-Cs-oxaalkanediyl,
X4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and
X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C]-C4-alkyl, C]-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4~haloalkoxy.
The formula (I) provides a general definition of the compounds according to the invention. Preferred substituents or ranges of the radicals listed in the formulae given above and below are illustrated below:
X preferably represents chlorine or bromine,
Y preferably represents chlorine or bromine,
Z preferably represents ethyl or n-propyl,
and, if
G preferably represents hydrogen (a),
then
A preferably represents hydrogen, or represents Ci-Cg-alkyl which is optionally mono-to trisubstituted by halogen, or represents Ca-Cg-cycloalkyl or Ci-Cg-alkoxy-Ci-C^ alkyl, each of which is optionally mono- to trisubstituted by halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy,
B preferably represents hydrogen, Ci-Cg-alkyl or Ci-C6-alkoxy-Ci-C4-alkyl or
A and B together with the carbon atom to which they are attached preferably represent saturated CVCg-cycloalkyl which is optionally substituted by Ci-Ce-alkyl or Q-C4-haloalkyl,
D preferably represents hydrogen, represents Ci-Cg-alkyl, Ci-Cg-alkenyl, Cj-Ce-alkoxy-C2-C4~alkyl or Ci-C6-alkylthio-C2-C4-alkyl, each of which is optionally
mono- to trisubstituted by halogen, represents Ca-Cg-cycloalkyl which is optionally mono- to trisubstituted by halogen, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C2-haloalkyl, or
A and D together preferably represent a C3-C6-alkanediyl or Ca-Ce-alkenediyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which are in each case optionally mono- to disubstituted by halogen, hydroxyl, Ci-C4-alkyl or C]-C4-alkoxy, or by a further C3-C6-alkanediyl, Cs-Ce-alkenediyl or C4-C6-alkanedienediyl group which forms a fused-on ring,
and, if
G preferably represents one of the groups

in which
E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur and M represents oxygen or sulfur, then R1 preferably represents Cj-Cio-alkyl, C2-C2o-alkenyl, Ci-Cs-alkoxy-Ci-Cs-alkyl or
l, each of which is optionally mono- to pentasubstituted by halogen, or represents Ca-Cg-cycloalkyl which is optionally mono- to trisubstituted by halogen, Ci-C4-alkyl or Ci-C4-alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulfur,
represents phenyl which is optionally mono- to trisubstituted by halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-alkoxy, d-C6-haloalkyl, Ci-C6-haloalkoxy, Ci-C6-

alkylthio or Ci-Ce-alkylsulfonyl,
represents 5- or 6-membered hetaryl which is optionally mono- to di substituted by halogen or Ci-Ce-alkyl and which contains one or two heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
R2 preferably represents Ci-C20-alkyl, C2-C2o-alkenyl, Ci-Ce-alkoxy^-Ce-alkyl or poly-Ci-C6-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by halogen,
represents Cs-Cg-cycloalkyl which is optionally mono- to disubstituted by halogen, or Ci-Ce-alkoxy, or
represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-Ce-haloalkyl or Cj-Ce-haloalkoxy,
R3 preferably represents Cj-Cg-alkyl which is optionally mono- to polysubstituted by halogen or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by halogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4-haloalkyl, Ci-C/j-haloalkoxy, cyano or nitro,
R4 and R5 independently of one another preferably represent Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-alkylamino, di-(Ci-Cg-alkyl)amino, Ci-Cg-alkylthio or Ca-Cg-alkenylthio, each of which is optionally mono- to trisubstituted by halogen or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to trisubstituted by halogen, nitro, cyano, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkyl or Ci-C4-ha.loalkyl,
R6 and R7 independently of one another preferably represent hydrogen, represent Cj-Cg-alkyl, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-C8-alkenyl or Ci-C8-alkoxy-C2-C8-alkyl, each of which is optionally mono- to trisubstituted by halogen, represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by halogen, Ci-Cg-alkyl, Cj-Cg-haloalkyl or Cj-Cg-alkoxy, or together represent a Ca-Ce-alkylene radical which is optionally mono- to disubstituted by Ci-C4-alkyl and in which optionally one methylene group is replaced by oxygen or sulfur,

A preferably represents hydrogen, represents Q-Cg-alkyl, Ca-Cg-alkenyl, Ci.Ce-alkoxy-Ci-C4-alkyl or C]-C6-alkylthio-Ci-C4-alkyl, each of which is optionally mono- to trisubstituted by halogen, represents Ca-Cg-cycloalkyl which is optionally mono- to trisubstituted by halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy,
B preferably represents hydrogen, Cj-Ce-alkyl or Ci-C4-alkoxy-Ci-C2-alkyl, or
A, B and the carbon atom to which they are attached preferably represent saturated Cs-Cg-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally substituted by Ci-Ce-alkyl, Ci-C4-haloalkyl or Ci-C$-alkoxy,
D preferably represents hydrogen, represents Ci-Cg-alkyl, Ci-Cg-alkenyl, Ci-Cg-alkoxy-C2-C4-alkyl or Ci-C6-alkylthio-C2-C4-alkyl, each of which is optionally mono- to trisubstituted by halogen, represents Ca-Cg-cycloalkyl which is optionally mono- to trisubstituted by halogen, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-Ci-haloalkyl, or
A and D together preferably represent a Cs-Ce-alkanediyl or C3-C6-alkenediyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which are in each case optionally mono- to disubstituted by halogen, hydroxyl, Ci-C4-alkyl or Ci-C4-alkoxy, or by a further Ca-Ce-alkanediyl, Ca-Ce-alkenediyl or C4-CValkanedienediyl group which forms a fused-on ring.
In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
X particularly preferably represents chlorine or bromine, Y particularly preferably represents chlorine or bromine, Z particularly preferably represents ethyl or n-propyl, and, if G particularly preferably represents hydrogen (a), then

A particularly preferably represents hydrogen, represents Cj-C/j-alkyl which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C3-C5-cycloalkyl or €^-€4-alkoxy-Ci-C3-alkyl each of which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl or Ci-C2-alkoxy,
B particularly preferably represents hydrogen, Cj-C^alkyl or Ci-C4-alkoxy-Ci-C2-alkyl or
A and B together with the carbon atom to which they are attached particularly preferably represent saturated C3-C7-cycloalkyl which is optionally substituted by Ci-C^-alkyl orCi-C2-haloalkyl,
D particularly preferably represents hydrogen,
D also particularly preferably represents Cj-Ce-alkyl, C3-C6-alkenyl, Ci-C4-alkoxy-Ca-Cs-alkyl or Ci-C4-alkylthio-C2-C3-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents Cs-Ce-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine Ci-Ci-alkyl, Ci-C2-alkoxy or trifluoromethyl, with the proviso, that in this case
A only represents hydrogen or Cj-C3-alkyl,
A and D together particularly preferably represent a Ca-Cs-alkanediyl group in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by C]-C2-alkyl or Ci-Cj-alkoxy
or A and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10
(FigureRemove)
and if
G particularly preferably represents one of the groups

(b),

(c),

.SOr—R

(d),



R4
— p
// R5 (e), E (f)

or

R°
?7 (g),



then

in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,

R1 particular preferably represents Cj-Cio-alkyl, C2-Ci0-alkenyl, Ci-C4-alkoxy-Ci-C2-alkyl or Ci-C4-alkylthio-Ci-C2-alkyl, each of which is optionally mono- to trisubstitutcd by fluorine or chlorine, or represents Ca-Ce-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl or Ci-C2-alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen,
represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, Ci-C4-alkoxy, Ci-C2-haloalkyl or Ci-C2-haloalkoxy,
represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or Ci-C2-alkyl,
R2 particularly preferably represents Ci-Cio-alkyl, C2-C]0-alkenyl, Ci-C4-alkoxy-C2-C4-alkyl or poly-Ci-C4-alkoxy-C2-C4-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine,
represents C3-C7-cycloalkyl which is optionally monosubstituted by Ci-C2-alkyl or C]-C2-alkoxy, or
represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C4-alkyl, methoxy, trifluoromethyl or trifluoromethoxy,
R3 particularly preferably represents Ci-C4-alkyl which is optionally mono- to trisubstituted by fluorine or chlorine or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, Ci-C4-alkyl, Cj-C4-alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
R4 and R5 independently of one another particularly preferably represent Ci-Ce
Ci-C6-alkoxy, Ci-C6-alkylamino, di-(Ci-C6-alkyl)amino, Ci-C6-alkylthio or C3-C4-alkenylthio, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, Ci-Ca-alkoxy, trifluoromethoxy, Ci-Cs-alkylthio, Ci-Cs-alkyl or trifluoromethyl,

R6 and R7 independently of one another particularly preferably represent hydrogen, represent CrC6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy, C3-C6-alkenyl or Ci-Ce-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, Ci-C4-alkyl or Ci-C4-alkoxy, or together represent a Cs-Ce-alkylene radical W7hich is optionally mono- to disubstituted by methyl and in which optionally one methylene group is replaced by oxygen,
A particularly preferably represents hydrogen, represents Ci-Ce-alkyl, C2-C6-alkenyl, Ci-C4-alkoxy-C-i-C3-alkyl or Ci-C^alkylthio-Ci-Cs-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents Cs-Cg-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl or Ci-C2-alkoxy,
B particularly preferably represents hydrogen, Ci-C4-alkyl or Ci-C4-alkoxy-Ci-C2-alkyl, or
A, B and the carbon atom to which they are attached particularly preferably represent saturated C3-C7-cycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally monosubstituted by Ci-C4-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy,
D particularly preferably represents hydrogen or
D also particularly preferably represents Ci-Ce-alkyl, Cs-Ce-alkenyl, Ci-C4-alkoxy-Ca-Ca-alkyl or Ci-C4-alkylthio-C2-C3-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents Ca-Ce-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl, Ci-C2-alkoxy or trifluormethyl, with the proviso, that in this case
A only represents hydrogen or C j -C3-alkyl,
A and D together particularly preferably represent a Cs-Cj-alkanediyl group in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by Ci-C2-alkyl or Ci-C2-alkoxy,

or A and D together with the atoms to which they are attached represent one of the groups AD-1 bis AD-10
(Figure Remove)
AD-10
In the radical definitions mentioned as being particularly preferred, halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
X very particularly preferably represents chlorine or bromine,
Y very particularly preferably represents chlorine or bromine,
Z very particularly preferably represents ethyl,
Z also very particularly preferably represents n-propyl,
and, if
G very particularly preferably represents hydrogen (a), then
A very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
B very particularly preferably represents hydrogen, methyl or ethyl, or
A and B together with the carbon atom to which they are attached very particularly preferably represent saturated Cg-cycloalkyl which is optionally substituted by methyl, ethyl or trifluoromethyl,
D very particularly preferably represents hydrogen,
D also very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso, that in this case
A only represents hydrogen, methyl or ethyl,
A and D together very particularly preferably represent a Cs-C^alkanediyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl, or
AD-1
and if
A and D together with the atoms to which they are attached represent the group below:
(FigureRemove)
G very particularly preferably represents one of the groups
O
in which
E represents a metal ion equivalent or an ammonium ion, L represents oxygen and M represents oxygen or sulfur, then
R1 yery_ ...particularly preferably represents Ci-Ce-alkyl, C2-Ce-alkenyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-Ca-alkylthio-Ci-Ca-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, #chlorine, methyl, ethyl or methoxy,
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,
R2 very particularly preferably represents Cj-Cg-alkyl, Ca-Ce-alkenyl or Ci-Cs-alkoxy-C2-C3-alkyl, cyclopentyl or cyclohexyl,
or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
R6 very particxilarly preferably represents hydrogen, represents Ci-C4-alkyl, Ca-Ce-cycloalkyl or allyl, represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl,

R7 veryjarticularly preferably represents methyl, ethyl, n-propyl, isopropyl or allyl,
R6 and R7 together very particularly preferably represent a Cs-Ce-alkylene radical in which optionally one methylene group is replaced by oxygen,
A very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
B very particularly preferably represents hydrogen, methyl or ethyl, or
A,B and the carbon atom to which they are attached very particularly preferably represent saturated CVcycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, trifluoromcthyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, or
D very particularly preferably represents hydrogen or
D very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso, that in this case
A only represents hydrogen, methyl or ethyl,
A and D together very particularly preferably represent a Ca-C-ralkanediyI group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl, or
A and D together with the atoms to which they are attached represent the group below:
(FigureRemove)

AD-1 X especially preferably represents chlorine or bromine,
Y especially preferably represents chlorine or bromine, Z especially preferably represents ethyl,
Z also especially preferably represents n-propyl,
and, if
G especially preferably represents hydrogen (a),
then
A especially preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl or cyclopropyl,
B especially preferably represents hydrogen, methyl or ethyl, or
A and B together with the carbon atom to which they are attached especially preferably represent saturated C^-cycloalkyl which is optionally monosubstituted by methyl,
D especially preferably represents hydrogen,
D also especially preferably represents methyl, ethyl, i-propyl, cyclopropyl or cyclohexyl,
with the proviso, that in this case
A only represents hydrogen, methyl or ethyl, or
A and D together especially preferably represent a C3-C4-alkanediyl group in which optionally one methylene group is replaced by sulfur, or
A and D together with the atoms to which they are attached represent the group below:
(FigureRemove) and if
G especially preferably represents one of the groups
(FigureRemove)
then
R1 represents Ci-C6-alkyl or Ci-C2-alkoxy-CrC2-alkyl,
R2 represents Ci-Ce-alkyl, Ca-Ce-alkenyl or benzyl,
A represents hydrogen, methyl, ethyl, n-propyl, i-propyl or cyclopropyl,
B represents hydrogen, methyl or ethyl, or
A, B and the carbon atom to which they are attached especially preferably represent saturated Ce-cycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally mono substituted by methyl or methoxy,
D especially preferably represents hydrogen,
D also especially preferably represents methyl, ethyl, i-propyl, cyclopropyl or cyclohexyl, with the proviso, that in this case A only represents hydrogen, methyl or ethyl,
A and D together especially preferably represent a Cs-C^alkanediyl group, or A and D together with the atoms to which they are attached represent the group below


AD-1.
The general or preferred radical definitions or illustrations listed above can be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply to the end products and, correspondingly, to the precursors and intermediates.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable).

Pnriicular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Especial preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being especially preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkanediyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitutions the substiruents can be identical or different.
In addition to the compounds mentioned in the preparation examples, the following compounds of the formulae (I-a) may be specifically mentioned:
(TableRemove)
Table 2: A, B and D as stated in table 1
Table 3: A, B and D as stated in table 1
Table 4: A, B and D as stated in table 1

Table 5: A, B and D as stated in table 1
X = Br; Y - Br; Z = n-C3H7
Preferred meanings of the groups listed above in connection with the crop plant compatibility-improving compounds ("herbicide safeners") of the formulae (Ha), (lib), (He), (lid) and (lie) are defined below.
n preferably represents the numbers 0,1,2, 3 or 4.
A1 preferably represents one of the divalent heterocyclic groupings shown below
(FigureRemove)


R

A2 preferably represents in each case optionally methyl-, ethyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methylene or ethylene.
R14 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propyl amino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
R15 preferably represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propyl ami no, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
R16 preferably represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.
R17 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymcthyl, ethoxymcthyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally
fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.
R1 preferably represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, ethox}Tnethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together with R represents one of the radicals -CH2-0-CH2-CH2- and -CH2-CH2-O-CH2-CH2- which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,
R19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n-or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl,
R20 preferably represents hydrogen, in each case optionally hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
R21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted methyl, ethyl, n-or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl,
X1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy,
X2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy,
X3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, elhoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy,
R preferably represents hydrogen, methyl, ethyl, n- or i-propyl, R23 preferably represents hydrogen, methyl, ethyl, n- or i-propyl,
R2 preferably represents hydrogen, in each, case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclo-pentylamino or cyclohexylamino,
R25 preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R26 preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituled phenyl, or together with R represents in each case optionally methyl- or
ethyl-substituted butane- 1,4-diyl (trimethylene), pentane-l,5-diyl, l-oxabutane-1,4-diyl or 3-oxnpentane-l,5-diyl,
X4 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy,
X5 preferably represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
Examples of the compounds of the formula (Ha) which are very particularly preferred as herbicide safeners according to the invention are listed in table 2 below.
Table 2: Examples of the compounds of the formula (Ha)
(TableRemove)
Examples of the compounds of the formula (lib) which are very particularly preferred as herbicide safeners according to the invention are listed in table 3 below.
(TableRemove)
Examples of the compounds of the formula (lid) which are very particularly preferred as herbicide safeners according to the invention are listed in table 5 below.
(TableRemove)
Examples of the compounds of the formula (He) which are very particularly preferred as herbicide safeners according to the invention are listed in table 6 below.
(TableRemove)
Most preferred as crop plant compatibility-improving compounds [component (c3)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperate and the compounds IIe-5 and IIe-11, and particular emphasis is given to cloquintocet-mexyl and mefenpyr-diethyl.
The compounds of the general formula (Ha) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-91/07 8 74, WO-A-95/07897).
The compounds of the general formula (lib) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. EP-A-191 736).
The compounds of the general fonnula (Ik) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-2 218 097, DE-A-2 350 547).
The compounds of the general formula (lid) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. DE-A-19 621 522/US-A-6 235 680).

The compounds of the general formula (He) to be used as safeners according to the invention are known and/or can be prepared by processes known per se (cf. WO-A-99/66 795/US-A-6 251 827).
Examples of the selective herbicidal combinations according to the invention comprising in each case one active compound of the formula (I) and in each case one of the safeners defined above are listed in table 7 below.
Table 7: Examples of the combinations according to the invention (TableRemove) Surprisingly, it has now been found that the active compound combinations defined above of substituted ketoenols of the general formula (I) (component (a')) and also (I-a) (component (b') and safcncrs (antidotes) from the component (c') listed above, while having very good compatibility with useful plants, have a particularly high herbicidal activity and can be used in various crops, in particular in cereals (especially wheat), but also in soybeans, potatoes, corn and rice, for the selective control of weeds.
Here, it has to be considered surprising that, from a large number of known safeners or
antidotes capable of antagonizing the damaging effect of a herbicide on the crop plants, it is in particular the compounds of component (c') listed above which are suitable for compensating the damaging effect of substituted cyclic ketoenols on the crop plants almost completely, without negatively affecting the herbicidal activity against the weeds to any considerable extent.
Emphasis may be given here to the particularly advantageous effect of the particularly preferred and most preferred combination partners made from component (c'), in particular with respect to sparing cereal plants, such as, for example, wheat, barley and rye, but also com and rice, as crop plants.
Using, for example, according to process (A) ethyl N-[(2,4-dicMoro-6-ethyl)phenylacetyl]-l-amino-4-ethylcyclohexanecarboxylate as starting material, the course of the process according to the invention can be represented by the reaction scheme below:

(Figure Remove)



Using, for example, according to process (Ba) 3-[(2,4-dichloro-6-ethyl)phenyl]-5,5-dimethyl-pyrrolidine-2,4-dione and pivaloyl chloride as starting materials, the course of the process according to the invention can be represented by the reaction scheme below:
(Figure Remove)


3 .CH,
H.C OH
H,C
H,C

CH,
I
H3C——COCI
CH,
base

Ui.ing, for example, according to process (B) (variant B) 3-[(2,4-dicrJoro-6-ethyl)pheny]]-5,5-pcntamcthylencpynolidine-2,4-dione and acetic anhydride as starting materials, the course of the process according to the invention can be represented by the reaction scheme below:
(Figure Remove)
Using, for example, according to process (C) 3-[(2,4-dichloro-6-ethyl)phenyl]-l,5-tetra-methylenepyrrolidone-2,4-dione and ethoxyethyl chloroformate as starting materials, the course of the process according to the invention can be represented by the reaction scheme below:
(Figure Remove)
Using, for example, according to process (D), variant a 3-[(2,4-dichloro-6-ethyl)phenyl]-5,5-dimethylpyrrolidone-2,4-dione and methyl chloromonothJoformate as starting materials, the course of the reaction can be represented as follows:
(Figure Remove)



Using, for example, according to process (D), variant B 3-[(2-cMoro-4-bromo-6-ethyl)-phenyl]-5-mcth\lp}T)olidine-2,4-dione, carbon disulfide and methyl iodide as starting materials, the course of the reaction can be represented as follows:
(Figure Remove)
Using, for example, according to process (E) 3-[(2,4-dichloro-6-ethyl)phenyl]-l,5-tri-methylenepyrrolidine-2,4-dione and methanesulfonyl chloride as starting material, the course of the reaction can be represented by the reaction scheme below:
(Figure Remove)



O Cl

+ CI-SO2-CH3
base

O —SO2CH3
O Cl

Using, for example, according to process (F) 2-[(2,4-dichloro-6-ethyl)phenyl]-5-isopropyl-5-methylpyrrolidine-2,4-dione and 2,2,2-trifluoroethyl methanethiophosphonyl chloride as starting materials, the course of the reaction can be represented by the reaction scheme below:
(Figure Remove)


|
Using, for example, according to process (G) 3-[(2,4-dichloro-6-elhyl)phenyl]-5-cyclopropyl-5-mcthylpyrrolidine-2,4-dione and NaOH as components, the course of the process according to the invention can be represented by the reaction scheme below: (Figure Remove)

sing, for example, according to process (IT) variant a 3-[(2,4-dichloro-6-ethyl)phenyl]-4-hydroxy-5,5-tetramcthylenepyrrolidone-2,4-dione and ethyl isocyanate as starting materials, the course of the reaction can be represented by the reaction scheme below:
(Figure Remove)



Using, for example, according to process (IT) variant B 3-[(2,4-dichloro-6-ethyl)phenyi]-5-methylpyrrolidine-2,4-dione and dimethylcarbamoyl chloride as starting materials, the course of the reaction can be represented by the scheme below: (Figure Remove)

CH,


Some of the compounds, required as starting materials in the process (A) according to the invention, of the formula (U)

(Figure Remove)

in which
A, B, D, X, Y, Z and R8 are as defined above
are novel.
The acylamino acid esters of the formula (II) are obtained, for example, when amino acid derivatives of the formula (XIV)
A^C02R8
D
in which
A, B, R8 and D are as defined above
are acylated with substituted phenylacetyl halides of the formula (XV)

in which
X, Y and Z are as defined above and
Hal represents chlorine or bromine,
(Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968, patent literature cited at the outset, for example WO 96/35 664)
or when acylamino acids of the formula (XVI)
(Figure Remove)

in which
A, B, D, X, Y and Z are as defined above
are cstcrified (Chem. Ind. (London) 1568 (1968)).
Some of the compounds of the formula (XVI)
(Figure Remove)


(XVI)

in which
A, B, D, X, Y and Z are as defined above are likewise novel.
The compounds of the formula (XVI) are obtained when amino acids of the formula (XVII)
A CO2H
*r,NH (XVII)
in which
A, B and D are as defined above
are acylated with substituted phenylaceryl halides of the formula (XV)

(Figure Remove) in which
X, Y and Z are as defined above and
Mai represents chlorine or bromine,
according to Schotten-Baumann (Organikum, VEB Dcutscher Verlag der Wissenschaften, Berlin 1977, p. 505).
Some of the compounds of the formula (XV) are novel and can be prepared by processes known in principle (WO 96/35 664).
The compounds of the formula (XV) are obtained, for example, when substituted phcnylacetic acids of the formula (XVIII)
(Figure Remove)


(xvin)

in which
X, Y and Z are as defined above
are reacted with halogenating agents (for example thionyl chloride, thionyl bromide, oxalyl cllloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride), if appropriate in the presence of a diluent (for example optionally chlorinated aliphatic or aromatic hydrocarbons, such as toluene or methylene cllloride), at temperatures of from -20°C to 150°C, preferably from -10°C to 100°C.
Some of the compounds of the formula (XVIII) are novel.
The compounds of the formula (XVIII) are obtained, for example, when substituted phcnylacetic esters of the formula (XIX)
(Figure Remove)
in which
o
X, Y, Z and R are as defined above,
are hydrolyzed in the presence of an acid (for example an inorganic acid, such as hydrochloric acid) or a base (for example an alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide) and, if appropriate, a diluent (for example an aqueous alcohol, such as mtthanol or ethanol), at temperatures between 0°C and 150°C, preferably between 20°C and 100°C.
Some of the compounds of the formula (XIX) are likewise novel and can be prepared by processes known in principle (WO 96/35 664).
The compounds of the formula (XIX) are obtained, for example, when substituted 1,1,1-tri-chloro-2-phenylethanes of the formula (XX)
(Figure Remove)


in which
X, Y and Z are as defined above
are initially reacted with alkoxides (for example alkali metal alkoxides, such as sodium methoxide or sodium ethoxide) in the presence of a diluent (for example the alcohol derived from the alkoxide) at temperatures between 0°C and 150°C, preferably between 20°C and 120°C, and then with an acid (preferably an inorganic acid, such as, for example, sulfuric acid) at temperatures between -20°C and 150°C, preferably between 0°C and 100°C.
Some of the compounds of the formula (XX) are novel and can be prepared by processes known in principle (WO 96/35 664).
The compounds of the formula (XX) are obtained, for example, when anilines of the formula (XXI)
(Figure Remove)
in which
X, Y and Z are as defined above
are reacted in the presence of an alkyl nitrite of the formula (XXII)
R13-ONO (XXII)
in which R13 represents alkyl, preferably Ci-Ce-alkyl,
in the presence of eopper(II) chloride and, if appropriate, in the presence of a diluent (for example an aliphatic nitrile, such as acetonitrile) at a temperature of from -20°C to SO°C, preferably from 0°C to 60°C, with vinylidene chloride (CH2=CC12).
Some of the compounds of the formula (XXI) are novel and can be prepared by processes which are generally known in principle. The compounds of the formula (XXTI) are known compounds of organic chemistry. Copper(II) chloride and vinylidene chloride have been known for a long time and are commercially available.
Some of the compounds of the formulae (XIV) and (XVII) are known, and/or they can be prepared by known processes (see, for example, Compagnon, Miocque Ann. Chim. (Paris) [14] 5, pp. 11-22,23-27(1970)).
The substituted cyclic aininocarboxylic acids of the formula (XVII) in which A and B form a ring are generally obtainable by the Bucherer-Bergs synthesis or by the Strecker synthesis, where they are in each case obtained in different isomeric forms. Thus, the conditions of the Bucherer-Bergs synthesis give mainly the isomers (for the sake of simplicity hereinbelow referred to as p) in which the radicals R and the carboxyl group are in equatorial positions, whereas the conditions of the Strecker synthesis give mainly the isomers (for the sake of simplicity hereinbelow referred to as a) in which the amino group and the radicals R are in equatorial positions.

(Figure Remove)
Bucherer-Bergs synthesis Strecker synthesis
(p-isomcr) (a-isomer)

(L. Munday, J. Chem. Soc. 4372 (1961); J.T. Eward, C. Jitrangeri, Can. J. Chem. 53, 3339
(1975).
Furthermore, the starting materials, used in the above process (A), of the formula (II)
(Figure Remove)

(II)

in which
A, B, D, X, Y, Z and R8 are as defined above

can be prepared by reacting aminonitriles of the formula (XXHJ)
(Figure Remove)
in which
A, B and D are as defined above
with substituted phcnylacetyl halides of the formula (XV)
(Figure Remove)

(XV)

in which
X, Y, Z and Hal are as defined above
which gives compounds of the formula (XXIV)
(Figure Remove)
in which
A, B, D, X, Y and Z are as defined above,
which are subsequently subjected to an acidic alcoholysis.
The compounds of the formulae (XXIII) are known from the applications cited at the outset. The compounds of the formula (XXIV) are novel.
The acid halides of the formula (III), carboxylic anhydrides of the formula (IV), chloroformic esters or chloroformic thioestcrs of the formula (V), chloromonothioforniic esters or chlorodithioformic esters of the formula (VI), alkyl halides of the formula (VII), sulfonyl chlorides of the formula (VIII), phosphorus compounds of the formula (IX) and metal hydroxides, metal alkoxides or amines of the formulae (X) and (XT), and isocyanates of the formula (XII) and carbamoyl chlorides of the formula (XIII) furthermore required as starting materials for carrying out the processes (B), (C), (D), (E), (F), (G) and (H) according to the invention are generally known compounds of organic or inorganic chemistry.
The compounds of the formulae (XIV) and (XVII) are furthermore known from the patent applications cited at the outset, and/or they can be prepared by the methods described therein.
The process (A) is characterized in that compounds of the formula (II) in which A, B, D, X, Y, Z and R are as defined above are subjected to an intramolecular condensation in the presence of a diluent and in the presence of a base.
Suitable diluents for the process (A) according to the invention are all organic solvents which are inert towards the rcactants. Preference is given to using hydrocarbons, such as toluene and xylcne, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreover polar solvents, such as dimethyl sulfoxide, sulfolane. dimethylformnmide and N-methylpyrrolidone, and also alcohols, such as methanol, ethanol. propanol, isopropanol, butanol, isobutanol and tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A) according to the invention are all customary proton acceptors. Preference is given to using alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of phase-transfer catalysts, such as, for example, triethylbenzylammonium chloride, tetrabutylamrnonium bromide, Adogen 464 (= methyltrialk}'l(Cg-Cio)amrnonium chloride) or IDA 1 (=tris(methoxyethoxyethyl)amine). It is furthermore possible to use alkali metals, such as sodium or potassium. Also suitable are alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and additionally also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.
When carrying out the process (A) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the process is carried out at temperatures between OrC and 250°C, preferably between 50°C and 150°C.
The process (A) according to the invention is generally carried out under atmospheric pressure.
When carrying out the process (A) according to the invention, the reaction component of the formula (II) and the deprotonating base are generally employed in equimolar to about doubly cquimolar amounts. However, it is also possible to use a relatively large excess (up to 3 mol) of one component or the other.
The process (Ba) is characterized in that compounds of the formula (I-a) are in each case reacted with carbonyl halides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Suitable diluents for the process (Ba) according to the invention are all solvents which are inert towards the acid halides. Preference is given to using hydrocarbons, such as benzine, benzene, toluene, xvlcne and tetralin, furthermore halogcnatcd hydrocarbons, such as mclhylcne chloride, chloroform, carbon tetrachloride, chlorobcnzene and o-dichlorobenzene, moreover ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, additionally carboxylic esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. The

hydrolytic stability of the acid halide permitting, the reaction can also be carried out in the presence of water.
Suitable acid binders for the reaction according to the process (Ba) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hiinig base and N,N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, moreover alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
In the process (Ba) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the process is carried out at temperatures between -20°C and +150°C, preferably between 0°C and 100°C.
When carrying out the process (Ba) according to the invention, the starting materials of the formula (I-a) and the carbonyl halide of the formula (III) are generally each employed in approximately equivalent amounts. However, it is also possible to use a relatively large excess (up to 5 mol) of the carbonyl halide. Work-up is carried out by customary methods.
The process (BP) is characterized in that compounds of the formula (I-a) are in each case reacted with carboxylic anhydrides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Suitable diluents for the process (B(3) according to the invention are preferably those diluents which are also preferred when using acid halides. Furthermore, excess carboxylic anhydride may simultaneously act as diluent.
The acid binders which are added, if appropriate, in the process (BP) are preferably those acid binders which are also preferred when using acid halides.
The reaction temperature in the process (BP) according to the invention may be varied within a relatively wide range. In general, the process is carried out at temperatures between -20°C and +150CC preferably between 0°C and 100°C.

When carrying out the process (B[3) according to the invention, the starting materials of the formula (I-a) and the carboxylic anhydride of the formula (IV) are generally each employed in approximately equivalent amounts. However, it is also possible to use a relatively large excess (up to 5 mol) of the carboxylic anhydride. Work-up is carried out by customary methods.
In general, diluent and excess carboxylic anhydride and the carboxylic acid formed are removed by distillation or by washing with an organic solvent or with water.
The process (C) is characterized in that compounds of the formula (I-a) are in each case reacted with chloroformic esters or chloroformic thioesters of the formula (V) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
Suitable acid binders for the process (C) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Htinig base and N,N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium oxide and calcium oxide, moreover alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
Suitable diluents for the process (C) according to the invention are all solvents which are inert towards the chloroformic esters or chloroformic thioesters. Preference is given to using hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzcne and o-dichlorcbenzene, moreover ketones, such as acetone and methyl isopropyl kctone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, additionally caiboxylic esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane.
When carrying out the process (C) accoiding to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction temperature is between -20°C and 41 OOrC preferably between 0CC and 50°C.
The proccrs (C) according to the invention is generally carried out under atmospheric pressure.

When carrying out the process (C) according to the invention, the starting materials of the -.formula (I-a) and the appropriate chloroformic ester or chloroformic thioester of the formula (V) are generally each employed in approximately equivalent amounts. However, it is also possible to use a relatively large excess (up to 2 mol) of one component or the other. Work-up is carried out by customary methods. In general, precipitated salts are removed and the reaction mixture which remains is concentrated by removing the diluent under reduced pressure.
The process (D) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with (Da) compounds of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid binder or (DP) carbon disulfide and then with alkyl halides of the formula (VII), if appropriate in the presence of a diluent and if appropriate in the presence of a base.
In the preparation process (Da), about 1 mol of chlorornonothioformic ester or chlorodithioformic ester of the formula (VI) is reacted per mole of starting material of the formula (I-a), at from 0 to 120°C, preferably from 20 to 60°C.
Suitable diluents, which are added, if appropriate, are all inert polar organic solvents, such as

e

thcrs, esters, amides, sulfones, sulfoxides, but also halogenated alkanes.

Preference is given to using dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimcthylformamide or methylene chloride.
If, in a preferred embodiment, the enolate salt: of the compound (I-a) is prepared by adding strong deprotonating agents, such as, for example, sodium hydride or potassium tert-butoxide, the further addition of acid binders may be dispensed with.
If acid binders are used, these are customary inorganic or organic bases, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
In the preparation process (Dp), in each case the equimolar amount or an excess of carbon disulfide is added per mole of starting material of the formula (I-a). The process is preferably carried out at temperatures of from 0 to 50rC and in particular at from 20 to 30°C.

Frequently, it is expedient to prepare initially the corresponding salt from the compounds of the formula (I-a) by adding a base (such as, for example, potassium teit-butoxide or sodium hydride). In each case, the compound (I-a) is reacted with carbon disulfide until the formation of the intermediate has ended, for example after several hours of stirring at room temperature.
Suitable bases for the process (D[3) are all customary proton acceptors. Preference is given to using alkali metal hydrides, alkali metal alkoxides, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogen bases. Examples which may be mentioned are sodium hydride, sodium mcthoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylethylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU).
Suitable diluents are all solvents which are customary for this process.
Preference is given to using aromatic hydrocarbons, such as benzene or toluene, alcohols, such as methanol, ethanol, isopropanol or ethylene glycol, nitriles, such as acetonitrile, ethers, such as tetrahydrofuran or dioxane, amides, such as dimethylformamide, or other polar solvents, such as dimethyl sulfoxide or sulfolane.
The further reaction with the alkyl halide of the formula (VII) is preferably carried out at from 0 to 70CC and in particular at from 20 to 50°C. Here, at least the equimolar amount of alkyl halide is used.
The process is carried out at atmospheric pressure or under elevated pressure, preferably at
atmospheric pressure.
Work-up is again carried out by customary methods.
The process (E) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with sulfonyl chlorides of the formula (VIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
In the preparation process (E), about 1 mol of sulfonyl chloride of the formula (VIII) is reacted per mole of starting material of the formula (I-a), at from -20 to 150°C, preferably from 20 to 70CC.

The process (H) is preferably carried out in the presence of a diluent.
Suitable diluents are all inert polar organic solvents, such as ethers, esters, amides, nitriles, sulfones, sulfoxides or halogenatcd hydrocarbons, such as methylene chloride.
Preference is given to using dimethyl sulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide, methylene chloride.
If, in a preferred embodiment, the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as, for example, sodium hydride or potassium tert-butoxide), the further addition of acid binders may be dispensed with.
If acid binders are used, these are customary inorganic or organic bases, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
The process (F) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with phosphorus compounds of the formula (IX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
In the preparation process (F), to obtain compounds of the formula (I-e), 1 to 2, preferably 1 to 1.3, mol of the phosphorus compound of the formula (IX) are reacted per mole of the compound (I-a), at temperatures between -40CC and 150°C, preferably between -10 and
The process (F) is preferably earned out in the presence of a diluent.
Suitable diluents are all inert polar organic solvents, such as ethers, esters, amides, nitriles, sulfides, sulfones, sulfoxides, etc.
Preference is given to using acctonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride.
Suitable acid binders, which are added if appropriate, are customary inorganic or organic bases, such as hydroxides, carbonates or amines. Examples which may be mentioned are sodium hydroxide., sodium carbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods of organic chemistry. The end products are preferably purified by crystallization, chromatographic purification or by "incipient distillation", i.e. removal of the volatile components under reduced pressure.
The process (G) is characterized in that compounds of the formula (I-a) are in each case reacted with metal hydroxides or metal alkoxides of the formula (X) or amines of the formula (XI), if appropriate in the presence of a diluent.
Suitable diluents for the process (G) according to the invention are preferably ethers, such as tetrahydrofuran, dioxane, diethyl ether or else alcohols, such as methanol, ethanol, isopropanol, but also water. The process (G) according to the invention is generally carried out under atmospheric pressure. The reaction temperature is generally between -20°C and 100°Q preferably between 0°C and 50°C.
The process (II) according to the invention is characterized in that compounds of the formula (I-a) are in each case reacted with (Ha) compounds of the formula (XII), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or (Hp) with compounds of the formula (XI11), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
In preparation process (Ha), about 1 mol of isocyanate of the formula (XII) is reacted per mole of starting material of the formula (I-a), at from 0 to 100°C, preferably at from 20 to 50°C.
The process (Ha) is preferably carried out in the presence of a diluent.
Suitable diluents are all inert organic solvents, such as ethers, esters, amides, nitriles, sulfones or sulfoxides.
If appropriate, catalysts may be added to accelerate the reaction. Suitable for use as catalysts are, very advantageously, organotin compounds, such as, dibutyltin dilaurate.
The process is preferably carried out at atmospheric pressure.
In the preparation process (HP), about 1 mol of carbamoyl chloride of the formula (XIII) is

reacted per mole of starting material of the formula (I-a), at from 0 to 150CC, preferably at from 20 to 70°C.
Suitable diluents \vhich are added, if appropriate, are all inert polar organic solvents, such as ethers, esters, amides, sulfones, sulfoxides or halogenated hydrocarbons.
Preference is given to using dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride.
If, in a preferred embodiment, the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as, for example, sodium hydride or potassium tert-butoxide), the further addition of acid binders may be dispensed with.
If acid binders are used, these are customary inorganic or organic bases, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
The reaction can be carried out at atmospheric pressure or under elevated pressure and is preferably carried out at atmospheric pressure. Work-up is carried out by customary methods.
The active compounds are well tolerated by plants and have advantageous toxicity to warm-blooded species; they can be employed for controlling animal pests, in particular insects, arachnids and nematodes encountered in agriculture, forests, in the protection of stored products and materials and in the hygiene sector. They may preferably be used as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of ihe Thysanura, for example, Lepisma saccharina.
From the order of the Collembola, for example, Onychiurus armatus.

From the order of ihe Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. and Schistocerca gregaria.
From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae and Blattella germanica.
From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
From the order of the Ilcteroptera, for example, Eun'gaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Flomoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotcttix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilapan'ata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosorna neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamcstra brassicae, Panolis flammca, ?podoptcra spp., Trichoplusia ni, Carpocapsa pomonclla, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kueliniella, Gallcria mellonella, Tincola bissclliJla, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua icticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Torlrix viridana, Cnaphalocerus spp. and Oulema oryzae.

From the order of the Colcoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Lcptinotarsa decemlineata, Phacdon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Ifypera postica, Dcnnestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tcnebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorphoptrus oryzophilus.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythiocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp. and Liriomyza spp.
From the order of the Siphonaptera, for example, Xenopsylla cheopis and Ceratophyllm spp.
From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dennanyssus gallinae, Eriophyes ribis, Phyllocoptruta olcivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetran)-chus spp., Hemitarsonemus spp. and Brevipalpus spp.
The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylcnchulus semipenetrans, Hcterodera spp., Globodera spp., Meloidogyne spp.., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp. and Bursaphelenchus spp.
If appropriate, the compounds or active compound combinations according to the invention may also be used in certain concentrations or application rates to act as herbicides. If appropriate, they can also be employed as intermediates or precursors for the synthesis of

further active compounds.
All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, including the transgenic plants and inclusive of the plant cultivars protectable or not protectable by plant breeders' rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offsets and. seeds.
The treatment according to the invention of the plants and plant parts with the active compounds or active compound combinations is carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, atomizing, evaporation, fogging, scattering or painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
The active compounds or active compound combinations can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emubifiers and/or dispersants and/or foam formers.
If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylcne, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobcnzenes, chlorocthylcnes or methylene chloride, aliphatic

hydrocarbons such as cyclohcxane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones Mich as acetone, methyl ethyl ketone, methyl isobutyl kctone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic cmulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolyzates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
The active compounds accouling to the invention, as such or in their formulations, can also be used as a mixture with known fungicides, bactcricidcs, acaricidcs, nematicidcs or insecticides, for example in order to widen the spectrum of action or to prevent the

de~\clopment of resistances in this way. In many cases, synergistic effects result, i.e. the activity of the mixture exceeds the activity of the individual components.
Compounds which are suitable as components in the mixtures are, for example, the following:
Fungicides:
aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine, azaconazole, azoxystrobin,
benalaxyl, bcnodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, binapacryl, hiphcnyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomcthionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufrancb, cymoxan.il, cyproconazole, cyprodinil, cyprofuram,
dcbacaib, dichlorophcn, diclobutrazole, diclofluanid, diclomczine, dicloran, diethofencarb, difenoconazole, dimeihirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,
cdifenphos, epoxiconazole, etaconazole, elhirimol, etridiazole,
famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumelovcr, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpct, fosctyl-aluminum, fosetyl-sodium, flhalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
guazatme,
hexachlorobenzcne, hcxaconazole, hymexazole,
irnazalil, imibenconazule, iminoctadine, iminoctadine albcsilate, iminoctadine triacetate, iodocaib, ipcona/ule, ipiobenfos (IBP), iprodione, irumamycin, isoprothiolane, isovaledione,
l.anicarnycin, krcjoxirn-mcili}!, copper preparations, such as: copper hydroxide, copper

naphthmate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
nickel dimcthyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
paclobutrazole, pcfurazoate, pcnconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propincb, pyraclostrobin, pyrazophos, pyrifenox. pyrimelhanil, pyroquilon, pyroxyfur,
quinconazole, quintozene (PCNB), sulfur and sulfur preparations,
tcbuconazole, tccloftalam, tecnazene, tetcyclacis, tctraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimcfon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
uniconazole,
validamycin A, vinclozolin, viniconazole,
zarilamide, zineb, ziram and also
Dagger G,
OK-8705,
OK-8 SOI,
(t-(l.l-dimcthylet]n])-p-(2-phcnoxycihyl)-lH-]52,4-triazole-l-cthanol,
u-(2,4-dkhlorophenyl)- p-fluoro-b-propyl-lH-1.2,4-triazole-l-ethanol,

a-(2,4-dichlorophenyl)-p-methoxy-a-melhyl-lH-l,2,4-triazole-l-ethanol,
a-(5-mcthyl-l,3-dioxan-5-yl)-p-[[4-(trifluoromethyl)phenyl]methylene]-lH-ls2,4-triazole-1-ethanol,
(5RS,6RS)-6-hydroxy-2J2,7,7-tetramcthyl-5-(lH-l,2,4-triazol-l-yl)-3-octanone,
(E)-a-(methoxyimino)-N-methyl-2-phenoxyphenylacetamide,
1-isopropyl {2-meth)'l-l-[[[l-(4-meihy]phenyl)ethy]]amino]carbonyl]propyl}carbamate,
l-(2,4-dichlorophcnyl)-2-(lH-l,2,4-triazol-l-y])ethanone 0-(phenylmethyl)oxime,
1 -(2-mcthyl-1 -naphthalenyl)-1 H-pyrrole-2,5-dione,
l-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,
l-[(diiodomethyl)sulfonyl]-4-methylbenzene,
l-[[2-(2,4-dicEorophenyl)-l,3-dioxolan-2-y]]melhyl]-lH-imidazole,
l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]melhyl]-lH-l,2,4-triazole,
l-[l-[2-[(2,4-dichlorophenyl)methoxy]phenyl]ethenyl]-lH-imidazole,
l-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,
2'J6'-dibromo-2-methyl-4'-trinuoromethoxy-4'-trifluoromelhyl-l,3-thiazole-5-carboxanilide,
2,2-dicliloro-N-[l-(4-cliloropheny])eih)il]-l-ethyl-3-methylcyclopropanecarboxamide,
2,6-dichloro-5-(methylthio)-4-pyrimidinyl thiocyanate,
2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide,
2;6-dic]jloro-N-[[4-(tniluoromeih}])phenyl]methyl]bcnzamide,
2-(2,3.3-triiodo-2-propenyl)-2H-tetrazole,
2-[(l-mcthylethyl)sulfony]]-5-(trichloromethyl)-ls3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-0-methyl-p-D-flycopyranosy])-a-D-glucopyranosy]]amino]-4-methoxy-1 H-pym)lo[2,3-d]pyrimidine-5-carbonitrile,
2-aminobutane,
2-bromo-2-(bromomethyl)pentanedinitrile,
2-chloro-N-(2,3-dihydro-1,1,3 -trimcthyl-1 H-iriden-4-y])-3-pyridinecarboxamide,
2-chloro-N-(2J6-dimethylphenyl)-N-(isothiocyanatomethyl)acctamide,
2-phenylphenol (OPP),
3,4-dichloro-l-[4-(difluoromethoxy)phenyl]-lH-pyrrole-2,5-dione,
3,5-dichloro-N-[cyano-[(l-methyl-2-propynyl)oxy]methyl]benzamide,
3-(l,l~dimeth)'lpropyl-l-oxo-lH-indene-2-carbonitrile,
3-[2-(4-chlorophenyl)-5-cthoxy-3-isoxazolidinyl]pyridine,
4-chloro-2-c}-ano-N,N-dimethyl-5-(4-mcihylphenyl)-lH-imidazole-l-sulfonamide,
4-methyltetrazolo[l,5-a]quinazolin-5(4H)-one,
8-(l,l-dimethylethyl)-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decane-2-melhanamine,
8-hydroxyquinoline sulfate,
9H-xanihene-2-[(phenylamino)carbonyl]-9-carboxylic hydrazide,
bis-(l-meth)lclhyl)-3-methyl-4-[(3-melhy]benzoyl)oxy]-2,5-thiophene dicarboxylate,
cis-l-(4-chlorophcnyl)-2-(lM-l,2,4-triazol-l-)'l)cycloheptanol,
cis-4-[3-[4-(] ,1-dimethylpropyl)phcnyl-2-mcihylpropyl]-2,6-dimethylmorpholine hydrocliloride,
cih\1 [(4-chlorophenyl)azo]cyanoacctate, potassium bicarbonate,

methanetdralhiol sodium salt,
methyl l-(2.3-dihydro-2,2-dimcthyl-l]l-inden-l-yl)-lH-imidazole-5-carboxylate,
methyl N-(236-dimelh)'lphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,
methyl N-(ch]oroacetyl)-N-(2,6 N-(233-dic]iloro-4-hydroxyphcny])-l-methylcyclohexanecarboxamide,
N-(2I6-dimcth}lphenyl)-2-methoxy-N-(tctrahydro-2-oxo-3-furany])acetamide,
N-(236-dimcthy]phcnyl)-2-mclhoxy-N-(tetrahydro-2-oxo-3-thienyl)acetamide,
N-(2-chloro-4-]]itrophenyl)-4-mcthyl-3-nitrobenzenesulfonamide,
N-(4-cyclohcx)ilphcny])-l,4,5,6-tetrahydro-2-pyrimidinamine,
N-(4-hex}-lphenyl)-l,4)5,6-tetrahydro-2-pyrimidinamine,
N-(5-chloro-2-mcthylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide,
N-(6-methoxy)-3-pyridinyl)cyclopropanecarboxamide,
N-[252,2-tiichloro-l-[(chloroacetyl)amino]ethyl]benzamide,
N-[3-chloro-4,5-bis(2-propinyloxy)phcnyl]-N'-methoxymethanimidamide,
N-formyl-N-h) droxy-DL-alanine sodium salt,
O,0-diethyl [2-(dipropylamino)-2-oxoethyl]ethylphosphoramidothioate,
O-methyl S-phcnyl phcnylpropylphosphoramidothioate,
S-mcihyl 1.2,3-bcnx.othiadiazole-7-caibothioate,
spiro[2H]-l-bcnzop)Tan-2,r(3"II)-isobcn2ofuran-3'-one,
4-[(3,4-dinuthoxyphcnyl)-3-(4-nuorophcn)'l)acr)'loyl]morpholine.
Battcricidcs:
bionopol, Jichlorophen, nitnipyrin, nickel dimcthyklithiocaibamate, kasugamycin,

octhilinone, furancarboxylic acid, oxytctracyclin, probcnazole, streptomycin, tecloftalam, copper sulfalc and other copper preparations.
Insecticidcs/ncni icides/ncmaticides:
abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avcrmectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,
Bacillus popilliae, Bacillus ^phaericus, Bacillus subtilis, Bacillus thuringiensis, baculoviruses, Bcauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb, bensultap, benzoximate, bctacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorclhoxyibs, chlorfenapyr, chlorfenvinphos, chloriluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, chlovaporthlin, chromafenozide, cis-resmethrin, cispermethrin, clocythrin, clocthocarb, clofcntezine, clothianidine, cyariophos, cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhcxatin, cypermcthrin, cj'romazine,
deltametliiin, dcmeton M, demeton S, demeton-S-mcthyl, diafenthiuron, diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapjTi,
eflusilanate, emamectin, cmpenthrin, endosulfan, Entomopflhora spp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,
fcnamiphos, fcnazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim, fenoxycaib, fcnpropatlirin, fenp)Trad, fenp)'rithj'in, fenpyroximate, fcnvalerate, fipronil, fluazinam, fluazuron, flubroc)lhrinate, flucycloxuron, flucythrinate, flufenoxuron, flumcihrin, llutcnzine, fluvalinate, fonophos, fosmetliilan, fosthiazate, fubfenprox, furathiocarb,
granulosis \ iruses,
halofcnozide. liCIl, heptenophcs, hexaflumuron, hexyihiazox, hydroprene,

imidadoprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin, nuclear polyhcdrosis viruses, lambda-cyhalothrin, lufenuron,
malathion, mecnibam, metaldehyde, meihamidophos, Melharhizium anisopliae,
Metharhizium flavoviride, methidatliion, methiocarb, melhoprene, methomyl,
nicthoxyfenozide, metolcarb, rnetoxadiazone, mevinphos, milbemectin, milbemycin,
monocrotophos,
nalcd, nitenpyram, nithiazine, novaluron, omcihoate, oxamyl, oxydemethon M,
Paecilomyces fumosoroseus, parathion A, parathion M, permelhrin, phenthoate, phorate, phosalone, phosmct, phosphamidon, phoxim, pirimicarb, pirimiphos A, pirimiphos M, profenofos, promccarb, propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos. pyrcsmclhrin, pyrelhrum, pyridaben, pyridalhion. pyrimidifen, pyriproxyfen,
quinalphos,
ribavirin,
saliihion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep, sulprofos,
tau-fluvalinate, tebufenozide, lebufenpyrad, tebupirimiphos, leflubenzuron, leflulhrin, temcphos, tcmivinphos, terbufos, Ictrachlon'inphos, lelradifon, iheta-cypermelhrin, thiacloprid, ihiamcihoxam, ihiapronil, ihialriphos, thiocyclam hydrogen oxalate, thiodicarb, ihiofancx, lhurhu;iensin, tralocythrin, tralomcthrin, triarathcne, triazamale, triazophos, tri-azurone, Irichlophcnidine, trichlorfon, triflumuron, trimethacarb,
vamidothion, vajjiliprole, Verticillium lecanii,
YI5302,
zeta-cypcrmcihrin, zolaprofos
(]R-cis)-[5-(phcn}lmelhyl)-3-furanyl]mcthyl 3-[(dihydro-2-oxo-3(2H)-furanylidene>

methyl]-2.2-dimcthy!cyclopropanecarboxylate, (3-phenoxyphcr,Y])jneihyl 2,2.3,3-tctramcthylc)'clopropanecarboxylate,
l-[(2-chloro-5-thiazc !yl)melh\l]tetrahydro-335-di;nethyl-N-nitro-l,3;5-triazine-2(]H)-imine,
2-(2-chloro-6-fluo]ophcnyl)-4-[4-(l,]-dimcthylcthy])phenyI]-4,5-dIhydrooxazole,
2-(occly]oxy)-3-dodec)1-l,4-naphthalenedione,
2-chloro-N-[[[4-(l-phenylethoxy)phcnyl]amino]carbonyl]benzamide,
2-chloro-N-[[[4-(2.2-dichloro-l,l-dif!uorocthoxy)phenyl]amino]carbonyl]benzamide,
3-mdhy]phenyl propylcarbamate,
4-[4-(4-cthoxyphcny!)-4-meth)r]pcnt):l]-l-fluoro-2-phenoxybenzene,
4-chIoro-2-(l,I-dimclhylelhyl)-5-[[2-(2,6-dimclhyl-4-phenoxyphenoxy)ethy]]thio]-3(2I-I)-pyridazinone,
4-ch!oro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)mcthoxy]-3(2H)-pyridazinone,
4-chloro-5-[(6-chloro-3-pyridin}'])mcthox}']-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone, Bacillus thuringiensis strain EG-2348, [2-benzoyl-l-(],l-dimethyletl'iy])]hydrazinobenzoic acid, 2,2-dimcthyl-3-(2,4-dichJorophenyl)-2-oxo-l-oxaEpiro[4.5]dec-3-en-4-yl butanoate,
[3-[(6-chloro-3-])yj'id!ny])metby]]-2-th]'azolidinylidene]cyanamide,
dih)xlR>2-(nitromcili}Icne)-2M-lJ3-ihiazinc-3(-4H)-carboxa]dehyde5
ethyl [2-[[l ,6-i!iliydro-6-oxo-l-(phcnylmcTh\'l)-4-pyridazinyl]oxy]eth}']]carbamate,
N-(3,-:!,4-trinu(iro-l-oxo-3-butenyl)eIycine,
N-(4-chIorophi'r.yl)-3-[4-(dif!uoromcihox>)phcny]]-4,5-dih)-dro-4-phcn)'l-lH-pyrazole-l-

carboxamide,
fN-[(2-chloro-5-thiazolyl)mcthy]]-N'-methyl-N"-nitroguanidine,
N-mcth};l-N'-(l-mc!h}'l-2-propeny])-1.2-hydmzinedicarbothioamide,
N-methyl-N'-2-propcnyl-l,2-hydrazinedicarbothioamide,
0,0-diethyl [2-(diprnpylamino)-2-oxoeihyl]etbylphosphoramidothioate,
N-cyanomcthyl-4-tnfluorometh)rlnJcotinamide,
3,5-dichloro-l-(333-dich!oro-2-propenyloxy)-4-j3-(5-trifluoromethylpyridin-2-yloxy)propoxy]benzene.
A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, is also possible.
When used as insecticides in their commercially available formulations and in the use forms prepared with these formulations, the active compounds according to the invention can furthermore exist in the form of a mixture with synergists. Synergists are compounds by which the activity of the active compounds is increased without it being necessary for the synergist added to be active itself.
The active compound content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active compound concentration of the use forms can be from 0.0000001 up to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
They are applied in a customary manner adapted to suit the use forms.
When used again;:t hygiene pests and stored-product pests, the active compound or active compound combinations is/are distinguished by excellent residual action on wood and clay as well as good stal iliry to alkali on limed substrates.
As already mcnlioncd above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species or plant varieties and plant cultivars which have been obtained by traditional biological breeding methods, such as hybridization or protoplast fusion, and the parts of these varieties and cultivars are treated. In

a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by recombinant methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Plants which are treated particularly preferably in accordance with the invention are those of the plant cultivars which are in each case commercially available or in use. Plant cultivars are understood as meaning plants with new traits which have been bred either by conventional breeding, by mutagencsis or by recombinant DNA techniques. They may take the form of cultivars, biorypes and genotypes.
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widened activity spectrum and/or an increase in the activity of the substances and compositions which can be used in accordance with the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to salinity in the water or soil, increased flowering performance, facilitated harvesting, accelerated maturation, higher yields, higher quality and/or better nutritional value of the harvested products, better storage characteristics and/or processibility of the harvested products are possible which exceed the effects which were actually to be expected.
The preferred transgenic plants or plant cultivars (those obtained by recombinant methods) to be treated in accordance with the invention include all those plants which, owing to the process of recombinant modification, were given genetic material which confers particular, advantageous, valuable traits to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to salinity in the water or soil, increased flowering performance, facilitated harvesting, accelerated maturation, higher yields, higher quality and/or higher nutritional value of the harvested products, better storage characteristics and/or processibility of the harvested products. Further examples of such traits, examples which must be mentioned especially, are better defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogcnic fungi, bacteria and/or viruses and an increased tolerance of the plants to certain hcibicidal active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potato, cotton,

oilseed rape, beets, sugar cane and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, potatoes, cotton and oilseed rape. Traits which are especially emphasized are the increased defense of the plants against insects, owing to toxins being formed in the plants, in particular toxins which are generated in the plants by the genetic material of Bacillus thuringiensis (for example by the genes CrylA(a), CryIA(b), CrylA(c), CryHA, CrylllA, CryIIlB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations; hcreinbelow "Bt plants"). Other traits which are particularly emphasized are the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Other traits which are especially emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example "PAT" gene). The genes which confer the desired traits in each case may also be present in the transgenic plants in combination with one another. Examples of "Bt plants" which may be mentioned are corn cultivars, cotton cultivars, soybean cultivars and potato cultivars wliich are commercially available under the trade names YIELD CARD® (for example corn, cotton, soya beans), KnockOut® (for example corn), StaiLink® (for example com), Bollgard® (cotton), Nucotn® (cotton) and NewLcaf® (potato). Examples of herbicide-tolerant plants wliich may be mentioned are corn cultivars, cotton cultivars and soybean cultivars which are commercially available under the trade names Roundup Ready® (tolerance to glyphosate, for example corn, cotton, soybean), Liberty Link® (tolerance to phosphinothricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example corn). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) wliich may be mentioned include also the varieties commercially available under the name Clearfield® (for example corn). Naturally, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.
The plants listed can be treated particularly advantageously with the compounds according to the invention or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds and mixtures also apply to the treatment of these plants. Particular emphasis may be given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The active compounds or active compound combinations according to the invention are not only active against plant, hygiene and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites), such as ixodid ticks, argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas. These parasites include:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the sub-orders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., I epikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
From the order of the Diptera and the sub-orders Nematocerina and Brachycerina, for example, Acdcs spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Ilydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp,, Fannia spp., Glossina rpp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Flippobosca spp., Lipoptena spp. and Melophagus spp.
From the order of the Siphonaptcrida, for example, Pulex spp., Ctenocephalides spp., Xcnopyslla spp. and Ceratophyllus spp.
From the order of the Hetcropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp.
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella gcrmanica and Supella spp.
From the sub-class of the Acaria (Acarida) and the orders of the Mcta- and Mesostigmata, for example, Areas spp., Ornithodorus spp.., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dcrmnnyssus spp., Raillietia spp., Pncumonyssus spp., Sternostoma spp. and Varroa -pp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Dcmodex spp., Trombicula spp.., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., llypodectcs spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptcs rpp., Notoedres spp., Kncmidocoptes spp., C)1odites spp. and I aminosioptes spp.
The active compounds or active compound combinations according to the invention are also suitable for controlling arthropods which attack agricultural livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honeybees, other domestic animals, such as, for example, dogs, cats, cage birds, aquarium fish, and so-called experimental animals, such as, for example, hamsters, guinea pigs, rats and mice. By combating these arthropods, it is intended to reduce deaths and decreased performances (in meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible by using the active compounds according to the invention.
In the veterinary sector, the active compounds or active compound combinations according lo the invention are used in a known manner by enteral administration, for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parcnteral administration, such as, for example, by means of injections (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal administration, for example in the form of dipping or bathing, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of shaped articles which comprise active compound, such as collars, ear tags, tail maiks, limb bands, halters, maiking devices and the like.
When administered to livestock, poultry, domestic animals and the like, the active compounds or active compound combinations can be used as formulations (for example powders, emulsions, flowables) which comprise the active compounds in an amount of 1 to 80% by weight, either directly or after dilution by a factor of 100 to 10 000, or they may be used in the form of a chemical bath.
Furthermore, it has been found that the compounds or active compound combinations according to the invention have a potent insecticidal action against insects which destroy

industrial materials.
The following insects rnay be mentioned by way of example and as being preferred, but without any limitation:
Beetles, such as
Hylotmpes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Piilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes nigicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.
Dermapterans, such as
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites, such as
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipcs, Reticulitermes santoncnsis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevaclcnsis, Coptotermes formosanus.
Bristletails, such as Lcpisma saccharina.
Industrial materials are to be understood as meaning, in the present context, non-live materials, such as, preferably, synthetic materials, glues, sizes, paper and board, leather, wood and timber products, and paint.
The materials to be very particularly preferably protected against attack by insects are wood and timber products.
Wood and timber products which can be protected by the composition according to the invention or mixtures comprising such a composition are to be understood as meaning, for example:
construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood cladding, windows and doors

made of wood, plywood, particle board, joiner's articles, or wood products which, quite generally, are used in the construction of houses or in joinery.
The active compounds or active compound combinations can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if appropriate desiccants and UV stabilizers and, if appropriate, colorants and pigments and other processing auxiliaries.
The insecticidal compositions or concentrates used for the protection of wood and wooden materials comprise the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight
The amount of the compositions or concentrates employed depends on the species and the occurrence of the insects and on the medium. The optimum rate of application can be determined upon use in each case by series of tests. However, in general, it suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
The solvent and/or diluent used is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetting agent.
Organochemical solvents which are preferably employed are oily or oil-type solvents having an evaporation number of above 35 and a flashpoint of above 30CC, preferably above 45°C. Substances which are used as such oily and oil-type solvents which have low volatility and are insoluble in water are suitable mineral oils or their aromatic fractions, or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.
Substances which are advantageously used are mineral oils with a boiling range of 170 to 220rC, white spirit with a boiling range of 170 to 220CC. spindle oil with a boiling range of

250 lo 350°C, petroleum or aromatics of boiling range 160 to 2SO°C, essence of turpentine and the like.
In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210CC or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220°C and/or spindle oil and/or monochloronaphthalene, preferably a-rnonochloronaphthalene, are used.
The organic oily or oil-type solvents of low volatility having an evaporation number of above 35 and a flashpoint of above 30°C, preferably above 45CC, can be partially replaced by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flashpoint of above 30°C, preferably above 45CC, and that the insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, part of the organochemical solvent or solvent mixture or an aliphatic polar organochemical solvent or solvent mixture is replaced. Substances which are preferably used are aliphatic organochemical solvents having hydroxyl and/or ester and/or ether groups, such as, for example, glycol ethers, esters and the like.
The organochemical binders used within the scope of the present invention are the synthetic resins and/or binding drying oils which are known per se and can be diluted with water and/or are soluble or clispcrsible or emulsifiable in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin, such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
The synthetic resin used as the tinder can be employed in the form of an emulsion, dispersion or solution. Up to 10% by weight of bitumen or bituminous substances can also be used as binders. In addition, colorants, pigments, water repellents, odor-masking substances and inhibitors or anticorrosives known per se and the like can also be employed.
The composition or the concentrate preferably comprises, in accordance with the invention, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as the

organochcinical binder. Preferably used according to the invention are alkyd resins with an , oil content of over 45% by weight, preferably 50 to 68% by weight.
All or some of the abovcmentioncd binder can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, the phosphoric esters, such as tributyl phosphate, the adipic esters, such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearate or amyl stearate, the oleatcs, such as butyl oleate, the glycerol ethers or relatively high-molccular-weight glycol ethers, glycerol esters and p-toluenesulfonic esters.
Fixatives are chemically based on polyvinyl alkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethylenebenzophenone.
Particularly suitable as a solvent or diluent is also water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispcrsants.
Particularly effective protection of wood is achieved by large-scale industrial impregnation processes, for example vacuum, double-vacuum or pressure processes.
If appropriate, the ready-to-use compositions can additionally comprise other insecticides and, if appropriate, additionally one or more fungicides.
Suitable additional components which may be admixed are. preferably, the insecticides and fungicides mentioned in WO 9-4/29 268. The compounds mentioned in that document are expressly part of the present application.
Very particularly preferred components which may be admixed are insecticides, such as chlorpyriphos, phoxim, silafluofin, alpharncthrin, cyfluthrin, cypermethrin, dcltamcthrin, perrncihrin, irnidacloprid, "NT-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, mcthoxyphcnoxid and triflumuron,

and fungicides, such as epoxyconazole, hexaconazole, azaconazole, propiconazole, lebuconazole, cyproconazole, mctconazole, imazalil, dichlofluanid, tolylfluanid, 3-iodo-2-propynylbutyl carbamale, N-octylisothiazolin-3-one and 4,5-dichloro-N-ocrylisothiazolin-3-one.
The compounds or active compound combinations according to the invention can at the same time be employed for protecting objects which come into contact with salt water or brackish water, in particular hulls, screens, nets, buildings, moorings and signaling systems, against fouling.
Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the Balanomorpha group (acom barnacles), such as Balanus or Pollicipes species, increases the frictional drag of ships and, as a consequence, leads to a marked increase in operation costs owing to higher energy consumption and additionally frequent residence in the dry dock.
Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.
Surprisingly, it has now been found that the compounds according to the invention, alone or in combination with other active compounds, have an outstanding antifouling action.
Using the compounds according to the invention, alone or in combination with other active compounds, allows the use of heavy metals such as, for example, in bis(trialkyltin) sulfides, tri-Ji-butyltin laurate, tri-/7-buryltin chloride, copper(I) oxide, triethyltin chloride, tri-»-buty]-(2-phenyl-4-chlorophenoxy)tin, triburyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl(bispyridine)bismuth chloride, tri-«-butyltin fluoride, manganese etbylenebismiocarbamate, zinc dimethyldithiocarbamate, zinc eihylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol 1-oxide, bisdi-mcthyldithiocarbamoylzinc cthylene-bisthiocarbamate, zinc oxide, copper(I) ethylene-bis-dithiocarbamate, copper thiocyanate, copper naphthenate and triburyltin halides to be dispensed with, or the concentration of these compounds to be substantially reduced.
If appropriate, the ready-to-use antifouling paints can additionally comprise other active

compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
Preferably suitable components in combination with the antifouling compositions according to the invention are:
'to
algicides such as
2-/(?r/-butylamino-4-cyclopropylamino-6-methylthio-l,3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
fungicides such as
benzo[6]thiophenccarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl butylcarbamate, tolylfluanid and azoles such as
azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;
molluscicides such as
fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb;
or conventional antifouling active compounds such as
4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2-(N,N-di-methylthiocarbarnoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridine-triphcnylborane, tetrabutyldistannoxane, 2,3,5,6-tetra-chloro-4-(methylsulfonyl)pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.
The antifouling compositions used comprise the active compounds according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
Moreover, the antifouling compositions according to the invention comprise the customary components such as, for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds according to the invention, antifouling paints comprise, in particular, binders.
Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are preferably insoluble in salt water. Paints may furthermore comprise materials such as rosin to allow controlled release of the active compounds. Furthermore, the paints may comprise plasticizers, modifiers which affect the rheological properties and other conventional constituents. The compounds according to the invention or the abovementioned mixtures may also be incorporated into self-polishing antifouling systems.
The active compounds or active compound combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed in domestic insecticide products for controlling these pests alone or in combination with other active compounds and auxiliaries. They are active against sensitive and resistant species and against all development stages. These pests include:
From the order of the Scorpionidea, for example, Buthus occitanus.
From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula aurumnalis, Dermatophagoides ptcronissimus, Dermatophagoides forinae.
From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the oider of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp. From the order of the Chilopoda, for example, Geophilus spp.
From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria, for example, Blatta orientalis, Blattella germanica, Blattella asahinai, Leucophaca maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria, for example, Acheta domesticus.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of ihe Isoptera, for example, Kalotermes spp., Reticulitermes spp.
From the order of the Psocoplera, for example, Lepinatus spp., Liposcelis spp.
From the order of the Coleptcra, for example, Anthrenus ?pp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptiinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zcamais, Stegobium paniceum.
From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Farmia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
From the order of the Lcpidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpuncklla, Tinea cloacella, Tinea pellionella, Tineolabisselliella.
From the order of the Siphonaptera, for example, Ctenocephalides cam's, Ctenocephalides fclis, Pulcx irritans, Tunga pcnetrans, Xcnopsylla cheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tctramorium caespitum.
From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthims pubis.
From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
They are used in the household insecticides sector alone or in combination with other suitable active compounds such as phosphoric esters, carbamates, pyrethroids, growth regulators or active compounds from other known classes of insecticides.
They are used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.
The active compounds or active compound combinations according to the invention can also be used as defoliants, desiccants, haulm killers and, in particular, as weed killers. Weeds in the broadest sense are understood as meaning all plants which grow at locations where they are undesired. Whether the substances according to the invention act as nonsclective or selective herbicides depends essentially on the application rate.
The active compounds or active compound combinations according to the invention can be used for example in the following plants:
Pjcotvledonoiv?..weeds of the genera; Abulilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphancs, Atripiex, Bellis, Bidcns, Capsclla, Carduus, Cassia, Centaurea, Chenopodium, Cirshim, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Tpomoea, Kochia, Lamium, Lcpidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania,

Sida, Sinapis, Solarium, Sonchus, Sphenoclca, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xantm'um.
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phased us, Pisum, Solanum, Vicia.
Monocotrlcdonous weeds of the penera; Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Arena, Bradiiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyl-octenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
M_onocoty]rdonpiis crops of the genera: Allium, Ananas, Asparagus, Arena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
However, the use of the active compounds or active compound combinations according to the invention is in no way restricted to these genera, but extends in the same manner to other plants.
Depending on the concentration, the active compounds or active compound combinations according to the invention are suitable for the nonselectire weed control on, for example, industrial terrains and railway tracks and on paths and locations with and without trees. Likewise the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop .fields, on lawns, turf and pasture-land, and for the selective control of weeds in annual crops.
The compounds or active compound combinations according to the invention have strong heibicidal activity and a broad activity spectrum when used on the soil and on aerial plant parts. To a certain extent, they are also suitable for the selective control of monocotylcdonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre- and post-emergence.

At certain concentrations or application rates, the active compounds or active compound combinations accouling to the invention can also be employed for controlling animal pests and fungal or bacteria] plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
The active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants and/or foam formers.
If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalcnes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzencs, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohcxane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl kctone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatly acid esters, polyoxyethylene fatty alcohol ethers, for example all-ylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates or else protein hydrolyzates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose.

Tackifiers such as caiboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic. polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants, such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
The active compounds according to the invention, as such or in their formulations, can also be used for weed control purposes as a mixture with known herbicides and/or with substances which improve crop plant compatibility ("safeners"), ready mixes or tank mixes being possible. Mixtures with herbicide products which contain one or more known herbicides and a safener are hence also possible.
Herbicides which are suitable for the mixtures are known herbicides, for example
acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-ally]), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon, cbJorimuron (-ethyl), chlornitrofcn, chlorsulfuron, chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, cleihodim, clodinafop (-propareyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop (-methyl), diclosulam, dicthatyl (-ethyl), difenzoquat, diflufcnicnn, diflufenzopyr, dimefuron, dimepiperate, dimethachJor, dimethamctr)Tn, dimcthenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocaib, cthalfluralin, ethametsulfuron (-methyl),

ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fcntrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, fJucarbazone (-sodium), flufenacet, flumetsulam, flumi-clorac (-pentyl), flumioxazin, flumiprcpyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, fJurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-buto\'}'propyl, -mepryl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isoprop)lammonium), halosafen, haloxyfop (-ethoxyethyl, -P-melhyl), hexazinone, imazamelhabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesosulfurone, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, mctsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxa-diargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen, pinoxaden, piperophos, prctilachlor, primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop, propisochlor, prcpoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfcn, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalide, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, lepraloxydim, tcrbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, ncmaticides, bird repellents, plant nutrients and soil conditioners, is also possible.
The active compounds or active compound combinations can be applied as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as

rcndy-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are applied in the customary manner, for example by watering, spraying, atomizing, scattering.
The active compounds or active compound combinations according to the invention can be applied both before and after plant emergence. They can also be incorporated into the soil prior to sowing.
The application rate of active compound can vary within a substantial range. Essentially, it depends on the nature of the desired effect. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil area, preferably between 5 g and 5 kg per ha.
The advantageous effect of the compatibility with crop plants of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within relatively wide ranges. In general, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100 parts by weight, particularly preferably 0.05 to 20 parts by weight, of one of the compounds which improves crop plant compatibility (antidotes/safeners) mentioned above under (c1) are present per part by weight of active compound of the formula (I) salts.
The active compound combinations according to the invention are generally applied in the form of finished formulations. However, the active compounds contained in the active compound combinations can, as individual formulations, also be mixed during use, i.e. be applied in the form of tank mixes.
For certain applications, in particular by the post-emergence method, it may furthermore be advantageous to include, as further additives in the formulations, mineral or vegetable oils which are compatible with plants (for example the commercial preparation "Rako Binol"), or ammonium salts, such as, for example, ammonium sulfate or ammonium thiocyanate.
The novel active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. Application is in the customary manner, for example by watering, spraying, atomizing, dusting or scattering.

The application rates of the active compound combinations according to the invention can be varied within a certain range; they depend, inter alia, on the weather and on soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha. particularly preferably between 0.01 and 0.5 kg per ha.
The active compound combinations according to the invention can be applied before and after emergence of the plants, that is to say by the pre-emergence and post-emergence method.
Depending on their properties, the safeners to be used according to the invention can be used for pretreating the seed of the crop plant (seed dressing) or can be introduced into the seed furrows prior to sowing or be used separately prior to the herbicide or together with the herbicide, before or after emergence of the plants.
Preparation and use of the active compounds and active compound combinations according to the invention are illustrated in the examples below.

Propnrntion examples (Figure Remove)
T-a-1

At from 0 to 20°C, 5.03 g of the compound of example II-l in 10ml of anhydrous dimethylformamide are added to 2.92 g (0.023 mol) of potassium tert-butoxide in 8 ml of anhydrous dimethylformamide, and the mixture is stirred at 20°C.
The reaction solution is poured into 80 ml of ice-water, the solution is, at 0 - 20°C, adjusted to pH 1 using concentrated hydrochloric acid, and the precipitate is filtered off with suction and dried. The product is then triturated with MTB ether/n-hexane.
Yield: 3.79 g (80% of theory), m.p. 245°C.
The following compounds of the formula (1-a) are obtained analogously to example (1-a-l) and in accordance with the statements on the preparation
(Table Remove)
0.5 ml (3.6 mmol) of triethylamine is added to 1.3 g of the compound of example I-a-1 in 30ml of anhydrous ethyl acetate. Under reflux, 0.38ml (0.0036 mmol) of isobutyryl chloride in 5 ml of anhydrous ethyl acetate is added dropwise.
The mixture is stirred under reflux. The end of the reaction is determined by thin-layer chromatography. The solvent is removed using a rotary evaporator, the residue is taken up in dichlorornethane and washed twice with 50 ml of 0.5 N NaOH solution and dried, and the solvent is distilled off. The product is then recrystallized using MTB ether/n-hexane.
Yield: 0.81 g (55% of theory), m.p. 155°C.
At 0 - 10°C, 0.6 ml (0.006 mol) of ethyl chlorofo (Table Remove)
rmate in 50 ml of anhydrous dichloromcthane is added dropwise to 2.34 g of the compound of preparation example I-a-14 in 50 ml of anhydrous dichloromethane and 0.84 ml (6 mmol) of triethylamine. The mixture is stirred at room temperature until the reaction has ended (monitored by thin-layer chromatography).
The solvent is then distilled off, the residue is taken up in dichloromethane, washed twice with 50 ml of 0.5 N NaOH solution and dried, the solvent is distilled off and the residue is recrystallizcd from MTB ether/n-hexane.
Yield: 2.2 g (79% of theory), m.p. 114°C.
The following compounds of the forrril . (I-c) are obtained analogously to example \i-c-l) and in accordance with the statements on the preparation

(Table Remove)
At an internal temperature of 30 - 40°C, 14.Og of the compound of preparation example XXIV-1 in 90 ml of mcthylene chloride are added dropwise to 16.4 g (0.162 mol) of cone. sulfuric acid. The mixture is stirred at 30 - 40°C for 2 hours, and 22 ml of abs. methanol are added dropwise so that an internal temperature of 40CC results. The mixture is stirred at a bath temperature of 40 - 70°C for 6 hours. The reaction solution is poured onto 0.17 kg of ice, the precipitate is filtered off with suction and the product is extracted with dichloromethane. The organic phase is washed with NaHC03 solution and dried, the solvent is removed using a rotary evaporator and the residue is recrystallized from MTB ether/n-hexane.
Yield: 5.04 g (33% of theory), m.p. 101°C. Example No. TI-2
(Figure Remove)
At room temperature. 22.S ml (0.3 mol) of thionyl chloride are added dropwise to 23.4 g of 2,4-dkhloro-6-ethylphcnylacetic acid. After the dropwise addition, the mixture is heated at 80CC until the evolution of gas has ceased, excess thionyl chloride is then removed using a rotary evaporator at 50°C, 100 nil of abs. toluene are added and the solvent is again removed using a rotary evaporator. The residue is taken up in 100 ml of abs. T1IF (solution 1).
42.5 g (0.2 mol) of methyl l-amino-4-melhylcyclohexanecaiboxylate hydrochloride are .initially charged in -400 ml of abs. IMF, and 61.5 ml (0.44 mol) of triethylamine are added. At 0 - 10CC, solution 1 is added dropwise. The mixture is stirred at room temperature for Ih.
The solvent is distilled off, the residue is taken up in IN HCl/dichloromethane solution and extracted. The organic phase is dried, the solvent is distilled off and the residue is recrystallized from MTB ether/n-hcxane.
Yield: 15.2 g (39% of theory), m.p. 122°C.

The following compounds of the formula (II) are obtained analogously to examples (II-1) and (II-2) and in accordance with the general statements on the preparation:
(Table Remove)
At room temperature, 15.2 ml (0.20 mol) of thionyl chloride are added dropwise to 12.9 g of 2,4-dibromo-6-cthylphenylacetic acid. After the dropwise addition, the mixture is heated at 80CC until the evolution of gas has ended, and excess thionyl chloride is then removed using a rotary evaporator at 50°C, 40 ml of abs. toluene are added, the solvent is again removed using a rotary evaporator and the residue is taken up in 30 ml of abs. THF (solution 1).
5.1 g of 3-amino-3-cyanotetrahydropyran are initially charged in 80 ml of abs. THF, 5.6 ml (0.04 mol) of triethylamine are added and solution 1 is added dropwise at 0 - 10°C. The mixture is stirred at room temperature for 1 hour.
The reaction solution is added to a mixture of 200 ml of ice-water/I00 ml of IN hydrochloric acid solution. The precipitate is filtered off with suction and taken up in dichloromethane. The organic phase is dried and concentrated using a rotary evaporator, and the residue is recrystallized from MTB ether/n-hexane.
Yield: 14.4 g (83% of theory), m.p. 98°C.

The following compounds of the formula (XXIV1) are obtained analogously to example (XXIV-1) and in accordance with the general statements on the preparation:

(Table Remove)
At room temperature, 67.6 ml (0.93 mol) of thionyl chloride are added dropwise to 100 g (0.310mol) of 2,4-dibromo-6-ethy]phenylacetic acid, and the mixture is then heated at 70°C until the evolution of gas has ended. Excess thionyl chloride is distilled off under reduced pressure, and the residue is distilled under high vacuum.
This gives 89 g (84% of theory) of the phenylacetyl chloride (XV-1) of b.p. 0.33 mbar
The compounds of the formula (XV) listed in the table below were prepared analogously and/or in accordance with the statements on the preparation: (Table Remove)
At room temperature, 105 g (0.42 mol) of the compound of example (XV-2) are added dropwise 1o a mixture of 56 g (1 mol) of KOH in 65 ml of water and 130 ml of methanol, and the mixture is heated under reflux for 5 hours. After cooling, the mixture is diluted with 200 ml of water and extracted with 250 ml of ethyl acetate. The aqueous phase is acidified with semi-concentrated hydrochloric acid and the precipitate is filtered off with suction and dried.
Yield: 82.5 g (100% of theory), m.p.: 101°C.
The compounds of the formula (XVIII) listed in the table below were prepared analogously and/or in accordance with the general statements on the preparation (WO 96/35664):
(Table Remove)


At 30-40°C, 410 ml of a 30% strength methanolic solution of sodium methoxide are added dropwise to a solution of 210 g (0.44 mol) of the compound of example (XX-1) in 220 g of methanol, the mixture is heated under reflux for 5 hours and then cooled to room temperature, and cone, sulfuric acid is added dropwise until the solution is acidic. The mixture is boiled under reflux for one hour, the methanol is distilled off and the solid residue is taken up in water. The organic phase is separated off and the aqueous phase is extracted twice with mcthylene chloride, and the combined organic phases are dried over MgSC>4 and concentrated.
Yield: 107.6 (67.5% of theory) of b.p. 0.05 mbar 60°C.
The compounds of the formula (XIX) listed in the table below were obtained analogously and/or in accordance with the general statements on the preparation (WO 96/35664):
Table
(Table Remove)
At at most 30CC, 31 ml (0.38 mol) of 1,1-dichloroethene are added dropwise to 4.3 g (0.04 mol) of tcrt-butyl nitrite and 4 g (0.03 mol) of copper(II) chloride (anhydrous) in 15 ml of anhydrous acctonitrile. Again at at most 30°C, 5.1 g (0.021 mol) of 2,4-dichloro-6-cthylaniline, dissolved in 7 ml of anhydrous acctonitrile, are then added dropwise. The mixture is stirred at room temperature until the evolution of gas has ceased. 80 ml of 20% strength hydrochloric acid solution are added carefully to the reaction solution, and the mixture is extracted with 85 ml of MTB ether. The organic phase is washed with 40 ml of 20% strength hydrochloric acid solution and then dried and filtered. The solvent is distilled off.
Yield: 9.44 g (74.9% of theory).
The compounds of the formula (XX) listed in the table below were obtained analogously and/or in accordance with the general statements on the preparation (WO 96/35664):
Table
(Table Remove)
' The compounds were introduced as crude products into the conversion reactions into the esters of the formula (XIX).
Preparation of 2,4-dichloro-6-ethylaniline
At room temperature, 18.82 g (0.14 mol) of copper(II) chloride are added to 200 ml of 37% strength hydrochloric acid solution, and 12.12 g (0.1 mol) of 2-ethylaniline are added dropwise at 50 - 60°C. The mixture is stirred at 90CC for 16 h, another 13.45 g (0.1 mol) of CuC12 are then added, and stirring at 90°C is continued for a further 16 h.
At room temperature, 0.2 mol of NaaSaOs solution are added, and the mixture is stirred for 15 min. With cooling, methylcne chloride is added, and the reaction mixture is adjusted to pi I 11 using concentrated NaOH solution. The organic phase is dried and concentrated. The residue is filtered through a little silica gel using mcthylene chloride as mobile phase.
Yield: 6.8 g (42% of theory)
Compound C
(Figure Remove)
22.20 ml (0.217 mo!) of acetic anhydride are added dropwise (exothermic reaction) to 40.52 g (0.217 mol) of the compound of example B in 227 ml of glacial acetic acid. The mixture is stirred for 1 h, 29.64 g (0.217 mol) of N-chlorosuccinimide are then added and the mixture is stirred at 100CC for about 3 h.
At 50CC, the reaction mixture is concentrated under reduced pressure; the crude product is dissolved in CI^Cli/I^O, and the organic phase is separated off and dried. The organic phase is then filtered through 500 g of silica gel using the mobile phase methylene chloride/methanol 98:2.
Yield: 17.6 g (32% of theory) Com pound XXI-1
(Figure Remove)

250 ml (3 mol) of concentrated hydrochloric acid, 360 ml (6 mol) of glacial acetic acid and 32 ml of water are added dropwise to 36.1 g (0.112 mol) of the compound of example C. The mixture is stirred under reflux for 7 h.
At room temperature, the reaction mixture is made alkaline using cone. NaOH; the salt is filtered off with suction, and the crude product is then extracted with CH2C12 and dried. The organic phase is filtered through silica gel using the mobile phase methylene chloride.
Yield: 19 g (63% of theory).
Example A Aphis gossypii test
Solvent: 7 parts by weight of dimethylformamide
Emulsificr: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with cmulsificr-containing water to the desired concentration.
Cotton leaves (Go^ypium hirsutum) which are heavily infested by cotton aphids (Aphis gossypii) are treated by being dipped into the preparation of active compound of the desired concentration.
After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.
In this test, for example, the following compound of the preparation examples shows superior activity compared to the prior art:

Table A
Plant-dama«in° insects
Aphis gossypii test

(Table Remove)
E> ample B Benmia test
Solvent: 7.5 parts by weight of dimethylformamide
EmuLsifier: 2.5 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Cotton plants (Gossypium hirsutum) which are infested by white fly (Bemisia tabaci) eggs, larvae and puparia are sprayed with the preparation of active compound of the desired concentration.
After the desired period of time, the kill in % is determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.
In this test, for example, the following compound of the preparation examples shows superior activity compared to the prior art:

Table B
Plant-damaging insects
Bemisia test

Active compound

Active compound concentration in ppm

Kill rate
in % after 10d



Ex. I-l-b-46
blown from EP-A-825 982

40

50



40

100

according to the invention
Fxnmpk C Myzus fcst
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with cmulsificr-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) which are heavily infested by the green peach aphid (Myzus pcrsicae) are treated by being dipped into the preparation of active compound of the desired concentration.
After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.
In this test, for example, the following compounds of the preparation examples show superior activity compared to the prior art:

Table C
Plant-damaaing insects
Myzus test

(Table Remove)
Example D Ncphotcttix test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with cmulsifier-containing water to the desired concentration.
Rice seedlings (Oryza saliva) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with the green rice leaf hopper (Nephotettix cincticc-ps) while the leafs are still moist.
After the desired period of time, the kill in % is determined. 100% means that all leaf hoppers have been killed; 0% means that none of the leaf hoppers have been killed.
In this test, for example, the following compounds of the preparation examples show superior activity compared to the prior art:

Table D
Plant-damaains insects
Nephotcttix test
(Table Remove)


Example E Phacdon larvae lest
Solvent: 7 parts by weight of dimeihylforrnamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
'to
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the mustard beetle (Phacdon cochlcariae) while the leaves are still moist.
After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
In this test, for example, the following compound of the preparation examples shows superior activity compared to the prior art:

Table E
Plant-damaainq, insects
Phaedon larvae test

Active compound

Active compound concentration in ppm

Kill rate in % after 7d



Ex. l-l-b-47
known from EP-A-825 982

100

65



Ex. I-b-3
according to the invention

100

100

Example F
Tetranychus test (OP resistant/dip treatment)
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and cmulsifier, and the concentrate is diluted with emulsificr-containing water to the desired concentration.
Bean plants (Phaseolus vulgaris) which are heavily infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are dipped into a preparation of active compound of the desired concentration.
After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
In this test, for example, the following compound of the preparation examples shows good activity:

Table F
Plant-damacin" mites
Tetranychus test (OP-resistant/dip treatment)
(Table Remove)


Fynmple G
'Post-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylary] polvglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants of a height of 5-15 cm are sprayed with the preparation of active compounds such that the particular amounts of active compound desired are applied per unit area. The concentration of the cpray liquor is chosen such that the particular amounts of active compound desired are npplicd in 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison lo the development of the untreated control.
The figures denote:
0% - no effect (like untreated control)
100% = total destruction

Ex simple Tl Prc-cmcrgcnce test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no effect (like untreated control)
100% = total destruction

0
I. Hcibicidal post-emergence action
Seeds of inonocotyledonous and dicotyledonous weed and crop plants are placed into sandy loam in wood fiber pots or in plastic pots, covered with soil and cultivated in a greenhouse, during the vegetation period also outdoors outside of the greenhouse, under good growth conditions. The test plants are treated 2-3 weeks after sowing at the one- to three-leaf stage. The test compounds, formulated as wettable powders (WP) or emulsifiable concentrates (EC) are, in various dosages with a water application rate of 300 1/ha (converted), with wetting agent (0.2 to 0.3%) added, sprayed onto the plants and the surface of the soil. The effect of the preparations is rated visually 3-4 weeks after the treatment of the test plants in comparison to untreated controls (herbicidal effect in percent (%): 100% effect - the plants have died, 0% effect = like control plants).
Use of safeners
If it is additionally to be tested as to whether safeners can improve the plant compatibility of test substances in the case of crop plants, the following options are used for applying the safener:
seeds of the crop plants are, before sowing, dressed with the safener substance (the amount of safener is stated in percent, based on the weight of the seed)
before the application of the test substances, the crop plants are sprayed with the safener at a certain application rate per hectare (usually 1 day before the application of the test substances)
the safener is applied together with the test substance as a tank mix (the amount of safener is stated in g/ha or as a ratio, based on the herbicide).
By comparing the effect of the test substances on crop plants without or with safener treatment, il is possible to assess the effect of the safener substance.

Example for h.rky (greenhouse)
(Table Remove)
Example for wheat (greenhouse)

*) one day before the application of the test substance, MORVS and TRZAS are treated with 100 g/ha of mefenpyr.
Example J
Critical concentration test/soil insects - treatment oftransgcnic plants
Test insect: Diabrotica balteata - larvae in soil
Solvent: 7 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
The test preparation is poured onto the soil. Here, the concentration of active compound in the preparation is virtually immaterial, only the amount by weight of active compound per unit volume of soil, which is stated in ppm (rng/1), matters. The soil is filled into 0.25 1 pots, and they are allowed to stand at 20°C.
Immediately after the preparation, 5 prcgcrminated com grains of the cultivar YIELD GUARD (trademark of Monsanto Comp., USA) are placed into each pot. After 2 days, the appropriate test insects are placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined by counting the corn plants that have emerged (1 plant = 20% activity).

Example' K
Heliolhis virescens test - treatment of tninsgenic plants
Solvent: 7 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a ;:uitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Soybean shoots (Glycine max) of the cultivar Roundup Ready (trademark of Monsanto Comp. USA) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with the tobacco budworm Heliolhis virescens while the leaves are still moist.
After the desired period of time, the kill of the insects is determined.

Clnims
1. A compound of the formula (I),
(Figure Remove)
in which
X represents halogen,
Y represents halogen and
Z represents ethyl or n-propyl,
and,if
G represents hydrogen (a), then
A represents hydrogen, represents in each case optionally substituted alky], cycloalkyl or alkoxyalkyl,
B represents hydrogen, alkyl or alkoxyalkyl or
A and D together with the carbon atom to which they are attached represent a saturated or unsaturatcd Ca-Cg-ring which is optionally substituted by alkyl or haloalkyl,
D represents hydrogen or represents an optionally substituted radical from the group consisting of alky], alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and optionally substituted cycloalkyl, or
A and D together with the atoms to which they are attached represent an unsubstitutcd or substituted cycle which is saturated or unsaturatcd and optionally contains at least one hctcroatom in the A.D-moiety,
and.if

G represents one of the groups
0 L
(b). /NjT*2 (c),
R4
(e)- E (f) or
in which
E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, M represents oxygen or sulfur, then
R1 represents in each case optionally halogen-substituted alky], alkcnyl, alkoxy-alky], alkylthioalkyl or polyalkoxyalkyl or represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl or represents in each case optionally substituted phenyl or hetaryl,
R2 represents in each case optionally halogen-substituted alkyl, alkcnyl, alkoxy-alkyl or polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R3, R4 and R5 independently of one another represent in each case optionally halogen- substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkcnylthio or cycloalkylthio or represent in each case optionally substituted phenyl. benzyl, phcnoxy or phcnylthio,
R6 and R independently of one another represent hydrogen, represent in each case optionally halogen-substituted alkyl, cycloalkyl, alkcr.yl, alkoxy, alkoxsall y], represent in each case optionally substituted phenyl or benzyl, or together \vith the N atom to which they are attached represent an optionally substituted cycle \vhich optionally contains oxygen or sulfur,

A represents hydrogen, represents in each case optionally halogen-substituted alky], alkcnyl, alkoxyalkyl or alkylthioalkyl or represents optionally substituted eycloalkyl,
B represents hydrogen, alkyl or alkoxyalkyl or
A and B together with the carbon atom to which they are attached represent an unsubstitutcd or substituted cycle which is saturated or unsaturated and optionally contains at least one heteroatom,
D represents hydrogen or represents an optionally substituted radical from the group consisting of alky], alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, or optionally substituted cycloalkyl, or
A and D together with the atoms to which they are attached represent an unsubstitutcd or substituted cycle which is saturated or unsaturated and optionally contains at least one heteroatom in the A,D-moiety.
2. The compound of the formula (I) as claimed in claim 1, in which
X represents chlorine or bromine,
Y represents chlorine or bromine,
Z represents ethyl or n-propyl,
and, then
G represents hydrogen (a), then
A represents hydrogen, or represents CVCs-alkyl which is optionally mono- to trisubirtitulcd by halogen, or represents Cs-Cs-cycloalkyl or Cj-Cg-alkoxy-C]-C.i-a!k\l, each of which is optionally mono- to trisubstituted by halogen, (YCV;i]k\IorCi-C6-aIkoxy,
B represents hydrogen, CpCYalkyl or Ci-Ce-alkoxy-crCValkyl or

A and B together \\ith the caibon atom to which they are attached represents saturated Cs-Cs-cycloalkyl which is optionally substituted by Ci-Co-alkyl or CrCVhaloalkyl,
D represents hydrogen, represents Cj-Cs-alkyl, Cj-Cg-alkenyl, C]-C6-alkoxy-C'-CYalkyl or C1-C6-alkylthio-C2-C4-a]kyl, each of which is optionally mono- lo trisubstituted by halogen, represents Cs-Cg-cycloalkyl which is optionally mono- to trisubstituted by halogen, Ci-C4-alkyl, CVC^alkoxy or CrC2-haloalkyl, or
A and D together represent a Cj-Q-alkanediyl or Ca-Cg-alkenediyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which are in each ease optionally mono- to disubstituted by halogen, hydroxyl, Cj-C^alkyl or Ci-C4-alkoxy, or by a further Cj-Cg-alkanediyl, Cj-CValkenediyl or C4-C6-alkanedienediyl group which forms a fused-on ring,
and, if
G represents one of the groups
R6

(e), E (f)

or

in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
then
R1 represents Cj-C2o-alkyl, C2-C:0-alkenyl; Ci-C6-a]koxy-Ci-C6-.
;:H;ylthio-(VC(,-c»lky], eacn of which is optionally mono- to pentasubstituted by halogen, or represents CVCVcycloalkyl which is optionally mono- to trisubstitv.'ed by halogen, Ci-C^lkyl or Ci-C4-alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulfur,
represents phcnyl which is optionally mono- to trisubstituted by halogen, cyano, nitro, Cj-Ce-alkyl, Q-Ce-alkoxy, Ci-Ce-haloalky], Cj-CVhaloalkoxy, Ci-C6-alk)lthio or d-Ce-alkylsulfonyl,
represents 5- or 6-membercd hctaryl which is optionally mono- to disubstituted by halogen or Cj-Ce-alkyl and which contains one or two heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
R represents Ci-C;o-alkyl, C2-C2o-alkenyl, Ci-Ce-alkoxy-Ci-Ce-alkyl or poly-C|-C represents Ca-Cg-cycloalkyl which is optionally mono- to disubstituted by halogen, CYC6-alkyl or Ci-C6-alkoxy, or
represents phenyl or benzyl, each of which is optionally mono- to irisubslitutcd by halogen, cyano, nitro, Cj-Cg-alkyl, CpCe-alkoxy, Ci-Ce-haloalkyl or Q-Ce-haloalkoxy,
R3 represents Cj-Cg-alkyl which is optionally mono- to polysubstituted by halogen or represents phcnyl or benzyl, each of which is optionally mono- to disubstituted by halogen, Ci-C6-alkyl, CrC6-a]koxy, Ci-C4-haloalkyl, CVCrhaloalkoxy, cyano or nitro,
R4 and R5 independently of one another represent Cj-Cg-alkyl, Cj-Cs-alkoxy, Ci-Cb-:ilk}lnmino, di-(Ci-Cs-i;lkyl)amino, CrC8-alkylthio or C2-C8-alkenyl-thio, each of v/hich is optionally mono- to trisubstituted by halogen or represent rhcnyl, phenoxy or phen)hhio, each of which is optionally mono-to trisubhtituted by halogen, nitro, cyano, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-;ilk\lihio, Ci-C4-haloalkylthio, CrC4-alkyl or CrC4-halcalkyl,

R and R independently of one another represent hydrogen, represent Cj-CValkyl, Cs-CYcycloalkyl, Ci-Cg-alkoxy, C5-CVc;lkenyl or Ci-CS-alkoxy-C2-C8-alkyl, each of which is optionally mono- to trisubstitutcd by halogen, represent phcnyl or benzyl, each of which is optionally mono- to trisub-stituted by halogen, Cl-CS-alkyl, Cl-C8-haloalkyl or Ci-Cg-alkoxy, or together represent a Cs-Ce-alkylene radical which is optionally mono- to disubs tituted by Cj-C4-alkyl and in which optionally one methylene group is replaced by oxygen or sulfur,
A represents hydrogen, represents Ci-Cg-alkyl, C2-Cg-alkenyl, Ci.Ce-alkoxy-Ci-C,-alkyl or Ci-Ce-alkylthio-Ci-C-t-alkyl, each of which is optionally mono- to trisubstitutcd by halogen, represents Cs-Cg-cycloalkyl which is optionally mono- to trisubstitutcd by halogen, Cj-Ce-alkyl or Q-Cc-alkoxy,
B represents hydrogen, Cj-CValkyl or Ci-C4-alkoxy-Ci-C2-alkyl, or
A, B and the carbon atom to which they are attached represent saturated Cs-Cg-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally substituted by Ci-Ce-alkyl, Ci-C4-haloalkyl or Ci-C
D represents hydrogen, represents Cl-Cg-alkyl, Cj-Cg-alkenyl, C\-C(,
CVCralkyl or Ci-C6-alkylthio-C2-C4-alkyl, each of which is optionally mono- to trisubstituted by halogen, represents Cs-Cg-cycloalkyl w:hich is optionally mono- to trisubstituted by halogen, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C2-haloalkyl, or
A and D together preferably represent a Cj-Cfc-alkanediyl or Cs-Co-alkenediyl group in which in each case optionally one metbvlcne group is replaced by oxygen or sulfur and which are in each case optionally mono- to disubstitutcd by halogen, hydroxyl, Ci-C4-alkyl or Ci-C4-:.lkoxy, or by a further Cs-Cg-alkaiKui)], Cs-CYalkcncdiyl or C-l-Ce-alkancdienediyl group which forms a fused-on ring.
The compound of the formula (I) as claimed in claim 1, in which

X represents chlorine or bromine, Y represents chlorine or bromine, Z represents ethyl or n-propyl, and, if G represents hydrogen (a), then
A represents hydrogen, represents CrC4-alkyl which is optionally mono- to trisubstituted by fluorine or chlorine, or represents Cs-Ce-cycloalkyl or Ci-C4-alkoxy-Ci-C3-alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl or Ci-C2-alkoxy,
B represents hydrogen, Ci-C4-alkyl or Ci-C^-alkoxy-Ci-Ci-alkyl or
A and B together with the carbon atom to which they are attached represent saturated C3-C7-cycloa]kyl which is optionally substituted by Ci-C4-alkvl or d-Crhaloalkyl,
D represents hydrogen,
D also represents CVCe-alkyl, Cj-Ce-alkenyl, Ci-C4-alkoxy-C2-C3-alkyl or CVG4--alkylthiO"CVC3-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents Cs-Ce-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl, Ci-Ca-alkoxy or trifluoromethyl, with the proviso, that in this case
A only represents hydrogen or Cj-Cs-alkyl,
A and D togLiher represent a Cs-Cj-alkanediyl group in which optionally one mcthjlcne group is replaced by oxygen or sulfur and which is optionally mono- to disubstitutcd by Ci-C2-a!kyl or Ci-C
or A and D together with the atoms to which they are attached represent one of the groups AD-1 to AD- 10
(Figure Remove)
in \\hkh

E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur and
M represents oxygen or sulfur,
then
R1 represents CrC]0-a]kyl, C2-C10-alkeny], CrC4-alkoxy-Ci-C2-alkyl or CrC4-alkyhhio-Ci-C2-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents Cs-Ce-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyl or Cj-Ci-alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen,
represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C4-alkyl, Ci-C4-a]koxy, Ci-C2-haloalkyl or C)-C2-haloalkoxy,
represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C,-C2-a]kyl,
R2 represents Ci-do-alkyl, Ca-Cio-alkenyl, Ci-C4-alkoxy-C2-C4-alkyl or poly-Ci-C4-alko>:y-C2-C4-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine,
represents C3-C7-cycloalkyl which is optionally monosubstituted by Cj-Ca-alkyl or Ci-C2-alkoxy, or
represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, Cj-C4-alkyl, mcthcxy, trifluoromethyl or trifluoromcthoxy,
R3 represents Ci-C4-a]kyl which is optionally mono- to trisubstituted by fluorine or chlorine or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, Ci-C4-alkyl, C]-C4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,

R4 and R5 independently of one another represent Cj-C6-alkyl, Ci-Ca-alkoxy, Cj-Ce-alkylamino, di-(Ci-CVa]kyl)amino, C]-C6-a]l:ylthio or C3-C4-alkenylthio, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, Ci-C3-alkoxy, trifluoromethoxy, Ci-C3-alkylthio, Cj-C3-alkyl or trifluoromethyl,
R6 arid R independently of one another represent hydrogen, represent Cj-C
C3'C6-cycloalky], CrC4-alkoxy, C3-C6-alkenyl or CrC6-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethy], Ci-C4-alkyl or d-C4-alkoxy, or together represent a Cs-Ce-alkylene radical which is optionally mono- to disubstituted by methyl and in which optionally one methylene group is replaced by oxygen,
A represents hydrogen, represents Cj-Ce-alkyl, C2-C6-alkenyl, Ci-C4-alkoxy-C-i-C3-alkyl or crC4-alkylthio-Ci-C3-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C3-C6-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-C2-alkyI or Ci-C2-alkoxy,
B represents hydrogen, Ci-C4-alkyl or Cj-C4-alkoxy-Ci-C2-alkyl, or
A, B and the carbon atom to which they are attached represent saturated C^-Cr cycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally monosubstituted by Ci-C4-alkyl, Ci-C2-haloalkyl or Ci-C4-alkoxy,
D represents hydrogen or
D also represents C1-C6-alkyl, C3-C6-alkenyl, d-C4-alkoxy-C2-C3-alkyl or C]-C4-:ilk\lthio-Ci-C3-alkyl, each of which is optionally mono- to trisubstitutcd by fluorine or chlorine, represents Ci-Cg-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, Ci-Ca-alkyl, Ci-C2-alkoxy or trifluormcthxl, with the proviso, that in this case

A

only represents hydrogen or

A and D together represent a Cs-Cs-alkanediyl group in which optionally one meth)lene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by Cj-Ca-alkyl or Q-Ca
or A and D together with the atoms to which they are attached represent one of the groups AD-1 to AD- 10
(Figure Remove)
AD-10
4. The compound of the formula (I) as claimed in claim 1, in which
X represents chlorine or bromine,
Y represents chlorine or bromine,
Z represents ethyl,
Z ;«lso represents n-propyl,
and, if
G represents hydrogen (a), then
A represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
B represents hydrogen, methyl or ethyl, or
A and B together with the carbon atom to which they are attached represent saturated Cg-cycloalkyl which is optionally substituted by methyl, ethyl or trifluoromethyl,
D represents hydrogen,
D :ilso represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso, that in this case
A only represents hydrogen, methyl or ethyl,
A and D together represent a Cj-C/t-alkanediyl group in which in each case optionally one mcthylcne group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl, or
A and D together with the atoms to which they are attached represent the group below:
NT I
AD-1 and, if G represents one of the groups
O L \ X*6
-^R1 (b). ^M'RZ 0. L^~NV (9)-
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen and
M represents oxygen or sulfur,
then
R1 represents Ci-C6-alky], C2-C6-alkenyl, Ci-C2-alkoxy-Ci-C2-alkyl, CrC2-alkylthio-Ci-C2-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally monosubstituled by fluorine, chlorine, methyl, ethyl or methoxy,
represents phcnvl \\hich is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, elhoxy, tiifluoromethyl or trifluoromethoxy,
represents furanyl, thicnyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,
R2 represents Cj-CValky], C2-C6-alkenyl or CrC5-alkoxy-C2-C3-alkyl, cyclopentyl or cyclohexyl,
or IL presents phcnyl or bcn/y], each of which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, mclhoxy, trifluoro-mcthyl or trifluoromelhoxy,
R6 represents hydrogen, represents CpQ-alkyl, Cs-Ce-cycloalkyl or ally], represents pheny] which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl,
R7 represents methyl, ethyl, n-propy], isopropyl or allyl,
R6 and R7 together represent a CyCs-alkylene radical in which optionally one mctbylene group is replaced by oxygen,
A represents hydrogen, methyl, ethyl, n-propy], isopropyl, n-butyl, isobutyl, sec-butyl, lert-butyl, cyclopropy], cyclopentyl or cyclohexyl,
B represents hydrogen, methyl or ethyl, or
A, B and the carbon atom to which they are attached represent saturated Ce-cyclo-alkyl in which optionally one methylene group is replaced by oxygen and \\hich is optionally monosubstituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, or
D represents hydrogen or D also represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopcntyl or cyclohexyl, with the proviso, that in this case
A only represents hydrogen, methyl or ethyl,
A and D together represent a C3-Cralkancdiyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl, or
A and D together with the atoms to which they are attached represent the group below:
N ^ I
AD-1
5. The compound of the formula (I) as claimed in claim 1, in which X represents chlorine or bromine, Y represents chlorine or bromine, Z represents ethyl, Z also represents n-propyl, and, if
G represents hydrogen (a), then
A represents hydrogen, methyl, ethyl, n-propyl, i-propyl or cyclopropyl, B represents hydrogen, methyl or ethyl, or
A and B together with the carbon atom to which they are attached represent saturated C6-cycloalkyl which is optionally monosubstituted by methyl,
D represents hydrogen,
D also represents methyl, ethyl, i-propyl, cyclopropyl or cyclohcxyl,
with the proviso, that in this case
A only represents hydrogen, methyl or ethyl, or
A :md D together represent a Cj-CVulkancdiyl group in which optionally one ITU ihylcne group is replaced by sulfur, or

A and D together with the atoms to which they are attached represent the group below:
NT I

AD-1 and,if

G especially preferably represents one of the groups (Figure Remove)
O


then
R1 represents Ci-C6-alkyl or Ci-C2-alkoxy-Ci-C2-alkyl,
R2 represents Cj-Ce-alkyl, C2-C6-alkenyl or benzyl,
A represents hydrogen, methyl, ethyl, n-propyl, i-propyl or cyclopropyl,
B represents hydrogen, methyl or ethyl, or
A, B and the carbon atom to which they are attached represent saturated Cft-cycloiilkyl in which optionally one methylene group is replaced by oxygen and which is optionally monosubstituted by methyl or mcthoxy,
D represents hydrogen,
D also represents methyl, ethyl, i-propy], cyclopropyl or cyclohcxy], with the pro\ iso, ;hat in this case A only represents hydrogen, methyl or ethyl,
A and D together represent a Cs-C-i-alkancdiyl group, or A and D together with the atoms to which the}' are attached represent the group below

(Figure Remove)


'N'
AD-1.

6.

The compound of the formula (I) as claimed in claim 1 in which the substituents are as defined in the table.
(Table Remove)


7. A process for preparing compounds of the formula (I) as claimed in claim 1 to 6, characterized in that, to obtain
(A) compounds of the formula (I-a),
(Figure Remove)
in which
A, B, 13, X, Y and Z are as defined above,
compounds of the formula (II),
(Figure Remove)

(II)

in which
A, B, D, X, Y and Z are as defined above,
and
a
R represents alkyl,
are condensed intramolccularly in the presence of a diluent and in the presence of a base,
(B) compounds of the formula (I-b) shown above in which A, B, D, R , X, Y and Z are as defined above, compounds of the formula (I-a) shown above in \\liich A, B, D, X, Y and Z are as defined above are reacted
a) with acid halides of the formula (III),

0 (no
in which
R is as defined above and Hal represents halogen or B) with c;.i box} lie anhydrides of the formula (IV)

R'-CO-O-CO-R1 (IV)
in which
R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(C) compounds of the formula (I-c) shown above in which A, B, D, R2, M, X, Y
and Z are as defined above and L represents oxygen, compounds of the
formula (I-a) shown above in which A, B, D, X, Y and Z are as defined
above are in each case reacted
with chioroformic esters or chloroformic thioesters of the formula (V)
R2-M-CO-C1 (V)
in which
R2 and M are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(D) compounds of the formula (I-c) shown above in which A, B, D, R , M, X, Y
and Z are as defined above and L represents sulfur, compounds of the
formula (I-a) ihown above in which A, B, D, X, Y and Z are as defined
above are in each case reacted
a) uiih chloromonoihioformic esters or chlorodithioformic esters of the formula (VI)
Ck M-R2
Y
S (VI)
in which
M and R2 are as defined above,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
or
ft) with carbon disulfide and then with compounds of the formula (VII)
R2-Hal (VII)
in which
R2 is as defined above and
Hal represents chlorine, bromine or iodine,
if appropriate in the presence of a diluent and if appropriate in the presence of a base,
(E) compounds of the formula (I-d) shown above in which A, B, D, R , X, Y
and Z are as defined above, compounds of the formula (I-a) shown above in
which A, B, D, X, Y and Z are as defined above are in each case reacted
with sulfony] chlorides of the formula (VIII),
R3-S02-C1 (VIII)
in which R is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(F) compounds of the formula (I-c) ihown above in which A, B, D, L, R4, R , X,
Y and Z are as defined above, compounds of the formula (I-a) shown above
in \\hich A. B, D, X, Y and Z arc as defined above are in each case reacted
with phosphorus compounds of the formula (IX)

R4 /
HsI-P
5
L R (IX)
in which
L, R4 and R5 are as defined above and
Mai represents halogen,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder,
(G) compounds of the formula (I-f) shown above in which A, B, D, E, X, Y and Z arc as defined above, compounds of the formulae (I-a) in which A, B, D, X, Y and Z are as defined above are in each case reacted
with metal compounds or amines of the formulae (X) and (XI), respectively,
R'VR"
R12
Me(OR10)t (X) K (XI)
in which
Me represents a mono- or divalent metal,
t represents the number 1 or 2 and
R10, R11, R1 independently of one another represent hydrogen or alkyl,
if appropriate in the presence of a diluent,
(II) compounds of the formula (I-g) shown above in which A, B, D, L, R6, R , X, Y and Z are as defined above, compounds of the formula (I-a) shown above in which A, B, D, X, Y and Z are as defined above are in each case
a) reacted with isocyanatcs or isothiccyanates of the formula (XII),
R6-N---- OL (XII)
in which

R and L arc as defined above,
if appropriate in ;hc presence of a diluent and if appropriate in the presence of a catalyst, or
B) reacted with caibamoyl chlorides or thiocarbamoyl chlorides of the formula (XJII),
R \ A
^N^CI
R (XIII)
in which
L, R and R are as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
8. The use of compounds of the formula (I) as claimed in claim 1 to 6 for preparing
pesticides and/or herbicides.
9. A pesticide and/or herbicide, characterized in that it comprises at least one
compound of the formula (I) as claimed in claim 1 to 6.
10. A method for controlling animal pests and/or unwanted vegetation, characterized in
that compounds of the formula (I) as claimed in claim 1 to 6 are allowed to act on
pests and/or their habitat.
11. The use of compounds of the formula (I) as claimed in claim 1 to 6 for controlling
animal pc 12. A process for preparing pesticides and/or herbicides, characterized in that
compounds of the formula (I) as claimed in claim 1 to 6 are mixed \\llh extenders
arid/or surfactants.
13. A composition, comprising an effective amount of an active compound combination
comprising

a') at least one substitute J cyclic kctocnol of the formula (I) in which A, B, D. X, Y, Z and G arc as defined above
or
IV) at least one substituted cyclic kctoenol of the formula (I-a) in which A and B together with the carbon atom to which they are attached represent saturated (Vcycloalkyl which is substituted by methoxy, ethoxy, propoxy, butoxy or isobutoxy or represent saturated Ce-cycloalkyl in wliich one methylene group is replaced by oxygen (DE-A-10 146 910) and
(c1) at least one crop plant compatibility-improving compound from the following group of compounds:
4-dichloroacelyl-l-oxa-4-azacpiro[4.5]decane (AD-67, MON-4660), 1-dichloro-
acctylhexahydro-3.3,8a-tnmcthylpyrrolo[l32-a]pyrimidine-6(2H)-one (dicyclonon,
BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-bcnzoxazine
(benoxacor), 1-mcthylhcxyl 5-chloroquinolinc-S-oxyacetate (cloquintocct-mexyl -
cf. also related compounds in EP-A-86750, EP-A-94349, EP-A-191736, EP-A-
492366), 3-(2-chlorobcnzyl)-l-(l-methyl-l-phenylethyl)urea (cumyluron),
a-(eyanomethoximino)phcnylacetonitri]e (cyometrinil), 2,4-dichlorophcnoxyacetic
acid (2,4-D), 4-(2,4 phcnylethyl)-3-(4-methylphcnyl)urea (daimuron, dymron), 3,6-dichloro-
2-rncthoxybenzoic acid (dicamba), S-l-methyl 1-phenylethyl piperidine-
1 -thiocarboxj'late (dimepiperate), 2,2-diehloro-N-(2-oxo-2-(2-propenyl-
amino)ethyl)-N-(2-propcny])acetamide (DKA-24), 2,2-dichloro-N,N-di-2-
pn^pcnylacctamide (dichlornjid), 456-dichloro-2-phenylpyrimidine (fenclorim),
ethyl l-(2,4-clieh]orophenyl)-5-trichloromcthyl-lH-1.2,4-triazole-3-carboxylate
(fenehlorazole-cthyl - cf. also related compounds in EP-A-174562 and EP-A-
346620), phenylmcihyl 2-chloro-4-tnfluoromcthylthiazole-5-carboxylate
(flurazole), 4-ehloro-N-(1.3-dioxo]an-2-ylmethoxy)-a-t]ifluoroacetophcnone oxime (fluxofenim), 3-diehlorcacet}'l-5-(2-furam'l)-2,2-di methyl oxazolidine (furilazole, MON-13900), cth)l 4,5-dihydro-5.5-diphenyl-3-iscxazolecarboxylate (isoxadifen-ethyl - cf. also ielated compounds in WO-A-95/07S97), l-(cthoxycarbonyl)cthyl 3,6-dichloro-2-methoxybcnzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid

(MCPA), 2-(4-chloro-o-tclyloxy)propionic acid (mecoprop), diethyl l-(2,4-dichoro-
pht r.}'l)-4,5-dihydro-5-mcthyl-l H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl -
cf. also related compounds in WO-A-91/07S74), 2-dichloromethyl-2-methyl-l,3-
dioxolane (MG-191), 2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate
(MG-S38), 1,8-naphthalic anhydride, a-(L3-dioxolan-2-ylmethoximino)-
phcnylacetonitrile (oxabetrinil), 2,2-dichloro-N-(],3-dioxolan-2-ylrnethyl)-N-(2-
propcny])acelamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine
(R-28725), 3-dichloroacetyl-2;2J5-trimethyloxazoIidine (R-29148), 4-(4-chloro-o-
toly])butyric acid, 4-(4-chlorophenoxy)butyric acid, diphcnylmethoxyacetic acid,
meth)'l diphenylmethoxyacetate, ethyl diphenylmcthoxyacetate, methyl l-(2-
chlorophenyl)-5-phenyl-lH-pyrazole-3~carboxylate, ethyl l-(2,4-dichlorophenyl)-5-
methyl-lH-pyrazole-3-carboxylate, ethyl l-(2,4-dichlorcphenyl)-5-isopropyl-lH-
pyrazole-3-carboxylate, ethyl l-(2,4-dichlorophenyl)-5-(l,l-dimethylethyl)-lH-
p)Tazole-3-carbox)'late, ethyl l-(2,4-dichlorophcnyl)-5-phenyl-lH-pyrazole-3-
carboxylate (cf. also related compounds in EP-A-269806 and EP-A-333131), ethyl
5-(2,4-dichlorobenzy])-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-
3-caiboxylate, eth)l 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf.
also related compounds in WO-A-91/OS202), 1,3-dimethylbut-l-yl
5-chloroquinolinc-S-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,
1 -allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, meth)'l 5-chloroquinoxaline-8-
oxyacctate, ethyl 5-chloroquinoline-8-oxyacelate, allyl 5-chloroquinoxaline-8-
oxyacctate, 2-oxoprop-l-yl 5-chloroquinoline-S-oxyacetate, diethyl
5-chloroquirioline-S-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate,
diethyl 5-chloroquinoline-8-ox}rmalonate (cf. also related compounds in EP-A-
582198), 4-caiboxychroman-4-yIacetic acid (AC-304415, cf. EP-A-613618),
4-chlorophenoxyacctic acid, 3,3'-dimcthyl-4-mcthoxybenzophenone, l-bromo-4-
chloromclhylsulfonylbenzene, l-[4-(N-2-mcthoxybenzoylsulfamoyl)phenyl]-3-
mcih}lurca (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)-
aminojbenzcncsulfor.amide), l-[4-(N-2-methoxybcnzoylsulfamoyl)phenyl]-
3,3-dimethyl urea, l-[4-(N-4.5-dimeth)lbcnzo\'lsiilfamo}l)pheny]]-3-methy]urea,
l-[4-iv"NT-nnphthylsulfamoy])pheny]]-3,3-dimcthylurea, N-(2-mcthoxy-5-
meilr. Ibcnzo) l)--l-(c) clopn^p) h!minocarbon}'])bcnzcncsulfonamide,
and/or one of the following compounds, defined by general formulae,

:>f the general formula (Ha)

o
A

(Ha)

or of the general formula (lib)
(Figure Remove)

(lib)

or of the formula (lie)


18

(Ik)

where
n represents a number between 0 and 5,
A1 represents one of the divalent heterocyclic groupings shown below,


(Figure Remove)
n represents a number between 0 and 5,
A2 represents optionally Cj-CValkyl- and/or Cj-C4-alkoxycarbonyl-substituted alkanedi) 1 ha\'ing 1 or 2 carbon atoms,

R

14

represents hydroNvl, mcreapto, amino, alkylamino or di-(Ci-C|-alky])amino,

oxy, Ci-Ce-alkyhhio,

R15 represents hvdroxyl, mcrcapto, amino, Ci-C6-alkcxy, Ci-Ce-alkylthio, Cj-Ce-alhylamino or di-(Ci-C|-alkyl)amino,
R1 represents in each case optionally fluorine-, chlorine- and/or bromine-substituted Ci-C4-alkyl,
R17 represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted CrC6-::ikyl, C2-C6-alkenyl or C2-C6-alkynyl, Cj-C4-alkoxy-Ci-C4-alkyl, dioxolanyl-Ci-C4-alkyl, furyl, fur);l-Ci-C4-alky], thienyl, ihiazolyl, pipcridiny], cr optionally fluorine-, chlorine- and/or bromine- or C]-C4-alkyl-substituted phenyl,
i a
R represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted Cj-C6-alkyl, C2-C6-alkenyl or Ci-Ce-alkynyl, Q-C4-a!koxy-Ci-C4-alkyl, dioxolanyl-Ci-C4-alkyl, furyl, furyl-C]-C4-alkyl, thienyl, thiazolyl, pipcridinyl, or optionally fluorine-, chlorine- and/or bromine- or Ci-C4 alkyl-substituted phenyl, or together with R17 represents Cs-Cg-alkanediyl or C2-C5-oxaalkaijediyl, each of which is optionally substituted by CVCYalky], phenyl, furyl, a fused benzene ring or by two substiruents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,
R19 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, clilorine- and/or bromine-substituted Ci-C4-alkyl, Cs-Ce-cycloalkyl or phenyl,
R20 represents hydrogen or in each case optionally hydroxyl-, cyano-, halogen- or Ci-C4-alkoxy-substitutcd Ci-C6-alk)'l, C3-C6-cycloa]kyl or tri(Ci-C4-alkyl)silyl,
R21 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C]-C4-alkyl, C3-C6-cycloalkyl or phenyl,
X1 represents nitro, cyano, halogen, Ci-C|-alkyl, C]-C4-haloalk)'l, Ci-C4-alkoxy 01 C)-C4-haloa]koxy,

X represents hydrogen, eyano, nitro, halogen, Q-C4-alkyl, d-Q-haloalkyl, Ci-C.,-alkoxy or CrC4-halo;;lkoxy,
X3 represents hydrogen, cyano, nitro, halogen, Cj-Q-alkyl, Ci-C4-haloalkyl, C]-C4-alkoxy or d-C4-haloalkoxy,
and/or the following compounds, defined by general formulae,
of the general formula (lid)
(Figure Remove)

or of the general formula (lie) (Figure Remove)

n represents a number between 0 and 5,

,22
R represents hydrogen or Ci-C4-alkyl,

>23
R represents hydrogen or Ci-C4-alkyl,

24
R
represents hydrogen, in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substitutcd Ci-CG-alkyl, C1-C6-aIkoxy, d-C6-alkyhhio, CrC6-alk)lamino or di-(Ci-C4-alk\i])amJno, or in each case optionally cyano-, halogen- or d-C4-alkyl-subi.-iituted d-Q-cycloalky], Cj-C6-cycloa]kyloxy, rj-C6-c)'eloalk)'lthio or C5-C6-cycloalk)1amino,
R" represents hydrogen, optionally cyano-, hyclroxyl-, halogen- or Ci-C4-alkoxy-subtitutcd C]-C6-alkyl, in each case optionally cyano- or halogen-substituted CYQr-ilkenyl or Cj^-alkyny], or optionally cyano-, halogen- or SLibstituted Cs-Ce-cycloal
R26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or Ci-C4-alkoxy-subiti luted Ci-Co-alkyl, in each case optionally cyano- or halogen- substituted Cs-CValkenyl or Cs-Cs-alkynyl, optionally cyano-, halogen- or Ci-C4-alkyl-substitutcd Cs-Ce-cycloalkyl, or optionally nitro-, cyano-, halogen-, Ci-C4-alkyl-, C]-C4-haloalkyl-, Ci-C4-alkoxy- or Ci-C4-haloalkoxy-substituted phenyl, or together with R25 represents in each case optionally Ci-C4-alkyl-substituted C2-C6-alkanediyl or CVCs-oxaalkanediyl,
X4 represents nitro, cyano, carboxy], carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, Ci-C4-allc\'l, C)-C4-haloalkyl, Ci-C4-alkoxy or Cj-C4-haloalkoxy, and
X5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, CrC4-;ilkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Cj-C4-haloalkoxy.
14. A composition as claimed in claim 13 where the crop plant compatibility-improving
compound is selected from the following group of compounds:
cloquintocct-mexyl, fcnchlorazole-ethyl, isoxadi fen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron or the compounds IIe-5 or IIe-1 1.
15. A method for controlling unwanted vegetation, characterized in that a composition
as claimed in claim 13 is allowed to act on the plants or their habitat.
16. The use of ihe composition as claimed in claim 13 for controlling unwanted
vegetation.
1 7. A compound of the formula (XXIV)
(Figure Remove)


in which
A, B, D, X, Y and Z are as defined above.

Documents:

2886-delnp-2005-abstract.pdf

2886-delnp-2005-claims-(19-02-2008).pdf

2886-DELNP-2005-Claims-(25-07-2007).pdf

2886-delnp-2005-claims.pdf

2886-DELNP-2005-Correspondence-Others-(25-07-2007).pdf

2886-delnp-2005-correspondence-others.pdf

2886-delnp-2005-description (complete).pdf

2886-DELNP-2005-Description-(Complete)-(25-07-2007).pdf

2886-delnp-2005-form-1.pdf

2886-delnp-2005-form-18.pdf

2886-delnp-2005-form-2.pdf

2886-DELNP-2005-Form-3-(25-07-2007).pdf

2886-delnp-2005-form-3.pdf

2886-delnp-2005-form-5.pdf

2886-DELNP-2005-GPA-(25-07-2007).pdf

2886-delnp-2005-gpa.pdf

2886-delnp-2005-pct-304.pdf

2886-delnp-2005-pct-search report.pdf

2886-DELNP-2005-Petition-137-(25-07-2007).pdf


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Patent Number 221954
Indian Patent Application Number 2886/DELNP/2005
PG Journal Number 32/2008
Publication Date 08-Aug-2008
Grant Date 12-Jul-2008
Date of Filing 29-Jun-2005
Name of Patentee BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Applicant Address ALFRED-NOBEL-STR. 50, 40789 MONHEIM, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 MARKUS DOLLINGER 16 RUE JEANMARIE LECLAIR, 69009 LYON,FRANCE
2 MARK WILHELM DREWS 38, D-40764 LANGENFELD, GERMANY
3 DIETER FEUCHT 7A, 65760 ESCHBORN, GERMANY
4 PETER LOSEL 90A,D-513171 LEVERKUSEN, GERMANY
5 MARTIN HILLS ITZELGRUND 5B, D-65510 IDSTEIN, GERMANY
6 REINER FISCHER NELLY-SACHS-STR. 23, D-40789 MONHEIM, GERMANY
7 STEFAN LEHR FRANKFURTER ALLEE 8A, D-65835 LIEDERBACH, GERMANY
8 UDO SCHNEIDER 40, D-51373 LEVERKUSEN, GERMANY
9 OLGA MALSAM VOR DEM LOSTEROF 19, D-51503 ROSRATH,GERMANY
10 ULRIKE WACHENDORFFNEUMANN MARKENWEG 85, D-56566 NEUWIED,GERMANY
11 INGO WETCHOLOWSKY 7B, D-40764 LANGENFELD, GERMANY
12 GUIDO BOJACK HOFACKERSTR., 23, D-65207 WEISBADEN, GERMANY
13 ALLEN RANDY MYERS P.O.BOX 12014, 2T.W.ALEXANDER DRIVE,RESEARCH TRIANGLE PARK,NC 27709,USA
14 TOMAS AULER 44, 42799 LEICHLINGEN, GERMANY
15 HERMANN HAGEMANN SIEBEN QUELLEN 27, D-45665 RECKLINGHAUSEN, GERMANY
16 HEINZ KEHHE, LLTISWEG 7A, D-65719 HOFHEIM, GERMANY
17 CHRISTOPHER HUGH ROSINGER AM HOCHFELD33, D-65719 HOFHEIM,GERMANY
PCT International Classification Number C07D 207/38
PCT International Application Number PCT/EP2004/000036
PCT International Filing date 2004-01-07
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 103 01804.2 2003-01-20 Germany