Title of Invention

SPIROCYCLIC 3-PHENYL-3-SUBSTITUTED -4- KETOLACTAMS AND-LACTONES

Abstract 1. Compounds of the formula (I) in which W represents cyano, halogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl or haloalkoxy, X represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Y represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, -A-B- represents the groups G represents halogen or nitro, R1 represents C1-C6-alkyl, R3 represents hydrogen or C1-C4-alkyl, and Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
Full Text FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"SPIROCYCLIC 3-PHENYL-3-SUBSTITUTED-4-KETOLACTAMS AND-LACTONES"
BAYER AKTIENGESELLSCHAFT, a German company, of D-51368 Leverkusen, Germany
The following specification particularly describes the nature of the invention and the manner in which it is to be performed :-


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The invention relates to novel phenyl-substituted 4-ketolactams and -lactones, to
5 processes and intermediates for their preparation and to their use as pesticides,
microbicides and herbicides.
It is already known that certain 3-phenyl-3-substituted-4-ketolactams and -lactones act as insecticides, acaricides and/or herbicides (JP-A-10-258 555). 10
However, the herbicidal, acaricidal and insecticidal efficacy and/or activity spectrum, and the compatibility of these compounds with plants, and in particular with crop plants, are not always satisfactory.
15 This invention now provides novel compounds of the formula (I)

O W
in which
20 W represents cyano, halogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl or
haloalkoxy,
X represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
25 Y represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,

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-A-B- represents the groups

5
G represents halogen or nitro,
represents Cj-Cg-alkyl,
10 R3 represents hydrogen or Cj-C^alkyl,
and
Q together with NH represents the cycle (1), together with oxygen represents the
15 cycle (2) and together with sulphur represents the cycle (3),
moreover, the invention provides novel compounds of the formula (I) in which
-A-B- represents the group 20
c)
and
W represents halogen or alkyl,
25 X represents hydrogen, halogen or alkyl,
Y represents hydrogen, halogen or alkyl,
Z represents hydrogen, halogen or alkyl,

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where at least one of the radicals W, X and Y represents alkyl and at least one of the radicals W, X and Y represents halogen,
G represents halogen or nitro, 5
R2 and R3 independently of one another represent hydrogen or CpC^alkyl and
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
10
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 in varying composition which, if appropriate, can be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their
15 preparation and use and the compositions comprising them. However, for the sake of
simplicity, only compounds of the formula (I) are referred to hereinbelow, although this is meant to refer both to the pure compounds and, if appropriate, to mixtures having different proportions of isomeric compounds.
20 The compounds of the formula (I) can be present both as mixtures and in the form of
their pure isomers. Mixtures of the compounds of the formula (I) can, if required, be separated in a manner known per se by physical methods, for example by chromatographic methods.

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Taking into account the meanings of Q and of the associated cycles (1) to (3), the following principal structures (1-1) to (1-3) result:

5 in which
A, B, G, W, X, Y, Z and R3 are as defined above.
Taking into account the different meanings of -A-B-, the following principal structures
10 (1-1 -a) to (1-1 -c) result if Q represents the cycle (1):


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in which
G, W, X, Y, Z, R1, R2 and R3 are as defined above.
5 Taking into account the different meanings of -A-B-, the following principal structures
(I-2-a) to (I-2-c) result if Q represents the cycle (2):

in which 10
G, W, X, Y, Z, R\ R2 and R3 are as defined above.
Taking into account the different meanings of -A-B-, the following principal structures (I-3-a) to (I-3-c) result if Q represents the cycle (3):

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in which
G, W, X, Y, Z, R1, R2 and R3 are as defined above.
5
Furthermore, it has been found
A) that compounds of the formula (1-1) to (1-3)

10 in which A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents halogen, preferably chlorine or bromine, are obtained 15
when compounds of the formulae (II-1) to (II-3)

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in which
5 A, B, Q, W, X, Y, Z and R3 are as defined above
are reacted with halogenating agents in the presence of a solvent and, if appropriate, in the presence of a radical initiator.
10 B) Compounds of the formulae (1-1) to (1-3)

in which
15 A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents nitro 20
are furthermore obtained when compounds of the formulae (II-l) to (II-3)

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in which
A, B, Q, W, X, Y, Z and R3 are as defined above 5
are reacted with nitrating agents, such as, for example, fuming nitric acid, in the presence of a solvent.
Some of the compounds of the formulae (II-1) to (H-3) required for the processes A
10 and B

in which
15 A, B, Q, W, X, Y, Z and R3 are as defined above
are known compounds (EP-A-596 298, WO 95/01358, WO 95/20572, EP-A-668
267, WO 95/26954, WO 96/25395, WO 96/35664, WO 97/02243, WO 97/01535,
WO 97/36868, WO 98/05638, WO 98/25928, WO 99/24437, WO 01/74 770, EP-A-
20 528 156, EP-A-647 637, WO 96/20196, WO 95/26345), or they can be synthesized
by the processes described therein.

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Suitable halogenating agents for the process A are, for example, sulphuryl chloride, sulphuryl bromide, thionyl chloride, thionyl bromide, imides, such as, for example, N-bromosuccinimide or N-chlorosuccinimide, chlorosulphonic acid, but also hypochlorites, such as, for example, tert-butyl hypochlorite. 5
Suitable nitrating agents for the process B are fuming nitric acid and also nitrating acid.
Furthermore, it has been found that the novel compounds of the formula (I) are highly
10 effective when used as pesticides, preferably as insecticides, acaricides and/or
fungicides and/or herbicides, and some of them are additionally highly compatible with plants, in particular with crop plants.
The formula (I) provides a general definition of the compounds according to the
15 invention. Preferred substituents or ranges of the radicals listed in the formulae
mentioned above and below are illustrated below:
Preference is given to compounds of group (I-a) in which A-B represents the group
a) 20
W preferably represents halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy or cyano,
25 X preferably represents hydrogen, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4-
haloalkyl, Ci-C4-haloalkoxy or cyano,
Y preferably represents hydrogen, halogen, Ci-Ce-alkyl, C]-C6-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy or cyano, 30

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Z preferably represents hydrogen, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, C1-C4 haloalkyl, C1-C4-haloalkoxy or cyano,
G preferably represents halogen or nitro, 5
R1 preferably represents Ci-C6-alkyl,
R3 preferably represents hydrogen,
10 Q preferably together with NH represents the cycle (1), together with oxygen
represents the cycle (2) and together with sulphur represents the cycle (3).
In the radical definitions mentioned as being preferred, halogen, also as substituent,
such as, for example, in haloalkyl, represents fluorine, chlorine, bromine and iodine, in
15 particular fluorine and chlorine.
Particular preference is given to compounds of group (I-a) in which A-B represents the group
a) 20
W particularly preferably represents fluorine, chlorine, bromine, Ci-Czt-alkyl Ci-C4-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or cyano,
25 X particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-
alkyl or C1-C4-alkoxy,
Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano, 30

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Z particularly preferably represents hydrogen, fluorine, chlorine, bromine, Q-C4-
alkyl, Ci-C4-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or cyano,
G particularly preferably represents chlorine, bromine or nitro, 5
R1 particularly preferably represents Cj-C^alkyl,
R3 particularly preferably represents hydrogen,
10 Q particularly preferably together with NH represents the cycle (1), together with
oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
In the radical definitions mentioned as being particularly preferred, halogen, also as
15 substituent, such as, for example, in haloalkyl, represents fluorine and chlorine, in
particular fluorine.
Very particular preference is given to compounds of group (I-a) in which A-B represents the group 20
a) , where
W very particularly preferably represents chlorine, bromine, methyl, ethyl,
propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy
25 or cyano,
X very particularly preferably represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,

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Y very particularly preferably represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
Z very particularly preferably represents hydrogen, fluorine, chlorine, bromine,
5 methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,
difluoromethoxy or cyano,
G very particularly preferably represents chlorine, bromine or nitro,
10 R1 very particularly preferably represents methyl, ethyl, propyl, isopropyl, butyl
or isobutyl,
R3 very particularly preferably represents hydrogen,
15 Q very particularly preferably together with NH represents the cycle (1) and
together with oxygen represents the cycle (2).
Especially preferred are compounds of the formula (I-a) in which A-B represents the group
20
a) —CH—CH— , where OR1

25

W especially preferably represents methyl, ethyl, chlorine, bromine, methoxy, trifluoromethyl or trifluoromethoxy,
X especially preferably represents hydrogen, chlorine, methyl or ethyl,
Y especially preferably represents hydrogen, chlorine, bromine, methyl, t-butyl, trifluoromethoxy, trifluoromethyl or cyano,

30

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Z especially preferably represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or trifluoromethyl,
5
G especially preferably represents chlorine or nitro (most preferably chlorine),
Rl especially preferably represents methyl or ethyl,
R3 especially preferably represents hydrogen,
10 Q especially preferably together with NH represents the cycle (1).
Preference is given to compounds of the formula (I-b) in which A-B represents the group
15 b) -0-CH2-, where
W preferably represents halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-aIkynyl, CrC6-alkoxy, d-C4-haloalkyl, Ci-C4-haloalkoxy or cyano,
20 X preferably represents hydrogen, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4-
haloalkyl, Ci-C4-haloalkoxy or cyano,
Y preferably represents hydrogen, halogen, CrC6-alkyl, Ci-C6-alkoxy, CrC4-haloalkyl, Ci-C4-haloalkoxy or cyano,

25
30

Z preferably represents hydrogen, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy or cyano,
G preferably represents halogen or nitro,
R3 preferably represents hydrogen,

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Q preferably together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
5 In the radical definitions mentioned as being preferred, halogen, also as substituent,
such as, for example, in haloalkyl, represents fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine.
Particular preference is given to the compounds of the formula (I-b) in which A-B
10 represents the group
b) -0-CH2-, where
W particularly preferably represents fluorine, chlorine, bromine, Ci-C4-alkyl,
15 Ci-C4-alkoxy, Cj-C2-haloalkyl, Ci-C2-haloalkoxy or cyano,
X particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl orCi-d-alkoxy,
20 Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-
alkyl, C]-C2-haloalkyl, Ci-C2-haloalkoxy or cyano,
Z particularly preferably represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C)-C4-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or cyano,
25
G particularly preferably represents chlorine, bromine or nitro,

R3

particularly preferably represents hydrogen,

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Q particularly preferably together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
5 In the radical definitions mentioned as being particularly preferred, halogen, also as
substituent, such as, for example, in haloalkyl, represents fluorine and chlorine, in particular fluorine.
Very particular preference is given to compounds of the formula (I-b) in which A-B
10 represents the group
b) -0-CH2-, where
W very particularly preferably represents chlorine, bromine, methyl, ethyl,
15 propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy
or cyano,
X very particularly preferably represents hydrogen, chlorine, bromine, methyl,
ethyl, propyl, methoxy or ethoxy, 20
Y very particularly preferably represents hydrogen, chlorine, bromine, methyl,
ethyl, propyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
Z very particularly preferably represents hydrogen, fluorine, chlorine, bromine,
25 methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,
difluoromethoxy or cyano,
G very particularly preferably represents chlorine, bromine or nitro,

30 R

very particularly preferably represents hydrogen,

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Q very particularly preferably together with NH represents the cycle (1) and together with oxygen represents the cycle (2).
Especially preferred are compounds of the formula (I-b) in which A-B represents the
5 group
b) -0-CH2-, where
10
W especially preferably represents chlorine, bromine, methyl or ethyl,
X especially preferably represents hydrogen, chlorine, methyl or ethyl,
Y especially preferably represents hydrogen, chlorine, bromine, methyl or ethyl,
15 Z especially preferably represents hydrogen, chlorine or methyl,
G especially preferably represents chlorine,
20
R3 especially preferably represents hydrogen,
Q especially preferably together with NH represents the cycle (1).
Preference is given to compounds of the formula (I-c) in which A-B represents the group
25
c) —CH—O— . where
FT
W preferably represents chlorine, bromine, methyl or ethyl,
30 X preferably represents chlorine, methyl or ethyl,

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Y preferably represents chlorine or bromine,
5
Z preferably represents hydrogen or chlorine,
G preferably represents halogen or nitro,
R2 preferably represents hydrogen or Ci-C^alkyl,
10 R3 preferably represents hydrogen or Cj^-alkyl,
Q preferably together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
15 Particular preference is given to compounds of the formula (I-c) in which A-B
represents the group
) —CH—O— . where
R2
20 W particularly preferably represents chlorine or methyl,
X particularly preferably represents chlorine, methyl or ethyl,
Y particularly preferably represents chlorine or bromine,
25
Z particularly preferably represents hydrogen or chlorine,
G particularly preferably represents chlorine, bromine or nitro,
30 R2 particularly preferably represents hydrogen, methyl or ethyl,

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R3 particularly preferably represents hydrogen,
Q particularly preferably together with NH represents the cycle (1), together with
5 oxygen represents the cycle (2) and together with sulphur represents the cycle
(3).
Very particular preference is given to compounds of the formula (I-c) in which A-B represents the group
10
c) —CH—O— » where R2

15
W very particularly preferably represents chlorine or methyl,
X very particularly preferably represents chlorine, methyl or ethyl,
Y very particularly preferably represents chlorine or bromine,
20 Z very particularly preferably represents hydrogen or chlorine,
G very particularly preferably represents chlorine, bromine or nitro,
R2 very particularly preferably represents hydrogen or methyl,
25

>3
R very particularly preferably represents hydrogen,

Q very particularly preferably together with NH represents the cycle (1) and together with oxygen represents the cycle (2). 30

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Especially preferred are compounds of the formula (I-c) in which A-B represents the group
c) —CH—O
R2

5
W especially preferably represents chlorine or methyl,
X especially preferably represents chlorine, methyl or ethyl,
10 Y especially preferably represents chlorine or bromine,
Z especially preferably represents hydrogen or chlorine,
G especially preferably represents chlorine, 15
R2 especially preferably represents hydrogen,
R3 especially preferably represents hydrogen or methyl,
20 Q especially preferably together with NH represents the cycle (1).
Most preference is given to compounds of the formula (I-2-a) in which A-B represents the group

25

a) —CH—O— , where
R1

W most preferably represents methyl,

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20
X most preferably represents hydrogen, methyl of chlorine (with extraordinary preference hydrogen),
Y most preferably represents hydrogen, methyl, chlorine or bromine (with
5 extraordinary preference methyl),
Z most preferably represents hydrogen, methyl of chlorine (with extraordinary preference methyl),
10 G most preferably represents chlorine or nitro,
Rl most preferably represents methyl or ethyl,
R3 most preferably represents hydrogen.

15
20
25

Most preference is furthermore given to compounds of the formula (I-2-b) in which A-B represents the group
b) -0-CH2-, where
W most preferably represents methyl,
X most preferably represents hydrogen, methyl or chlorine (with extraordinary preference hydrogen),
Y most preferably represents hydrogen, methyl, chlorine or bromine (with extraordinary preference methyl),

Z most preferably represents hydrogen, methyl or chlorine (with extraordinary
30 preference methyl),

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G most preferably represents chlorine or nitro (with extraordinary preference chlorine),
R3 most preferably represents hydrogen.
5
Especially preferred are compounds of the formula (I-2-c) in which A-B represents the
group
c)
—CH—O— . wnere
10
R2
W
most preferably represents methyl,
X
most preferably represents hydrogen,
15 Y
most preferably represents methyl,
most preferably represents methyl,
20
most preferably represents chlorine,
R'
most preferably represents hydrogen,
RJ
most preferably represents hydrogen.
25 The abovementioned general or preferred radical definitions and illustrations can be
combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates.

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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).
5 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 particularly preferred.
Very particular preference is given to the compounds of the formula (I) which contain a
10 combination of the meanings listed above as being very particularly preferred.
Special 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. 15
Most 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 most preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case
20 be straight-chain or branched as far as this is possible, including in combination with
heteroatoms, such as, for example, in alkoxy.
Using, for example, according to process (A) 3-(3,4-dichloro-2,6-dimethyl)phenyl-
5,5-(3-methoxy)pentamethylenepyrrolidine-2,4-dione or its enole as starting material,
25 the course of the process according to the invention can be represented by the
following reaction scheme:

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Using, for example, according to process (B) 3-(2,5-dichloro-6-methyl)phenyl-5,5-
(3-methoxy)pentamethylenefuran-2,4-dione or its enole, the course of the process
5 according to the invention can be represented by the following reaction scheme:

The process (A) is characterized in that compounds of the formula (II) in which A, B,
Q, W, X, Y, Z and R3 are as defined above are reacted in the presence of a diluent
10 and a halogenating agent and, if appropriate, a radical initiator. Suitable for use as
radical initiators are, for example, benzoyl peroxide or azobisisobutyronitrile.
Suitable diluents used in the process (A) according to the invention are all organic solvents which are inert to the halogenating agents. Preference is given to using
15 hydrocarbons, such as benzene, toluene and xylene, furthermore ethers, such as
methyl tert-butyl ether, dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreover halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, 6.icmoTobeTi2eTie, but also esters, such as etlny\ acetate.
20

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Suitable halogenating agents for process A are, for example, sulphuryl chloride, sulphuryl bromide, thionyl chloride, thionyl bromide, imides, such as, for example, N-bromosuccinimide, N-chlorosuccinimide, furthermore chlorosulphonic acid, but also hypochlorites, such as, for example, tert-butyl hypochlorite.
5
When carrying out the process (A) according to the invention, the reaction temperatures can be varied within a relatively large range. In general, the process is carried out at temperatures between -40°C and 150°C, preferably between 0°C and 100°C.
10
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
15 components of the formula (II) and the halogenating agents are generally employed in
approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 3 mol) of one or the other component.
Purification is generally carried out after aqueous work-up, by crystallization or by
20 chromatographic purification on silica gel.
The process (B) is characterized in that compounds of the formula (II) in which A, B, Q, W, X, Y, Z and R3 are as defined above are reacted in the presence of a diluent and in the presence of a nitrating agent. 25
Diluents suitable for use in the process (B) according to the invention are all inert organic solvents. Preference is given to using halogenated hydrocarbons, such as methylene chloride, chloroform, dichlorobenzene, dichloroethane.
30 Suitable nitrating agents are nitrating acids, preferably fuming nitric acid.

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When carrying out the process (B) according to the invention, the reaction temperatures can be varied in a relatively wide range. In general, the process is carried out at temperatures between -50°C and 150°C, preferably between 0°C and 80°C. 5
The process (B) according to the invention is generally carried out under atmospheric pressure.
When carrying out the process (B) according to the invention, the reaction
10 components of the formula (II) and the nitrating agent are generally employed in
approximately equimolar amounts. However, it is also possible to use a relatively large excess (up to 5 mol) of one or the other components.
Purification is carried out by customary work-up by crystallization or
15 chromatographic purification on silica gel.
The active compounds are suitable for controlling animal pests, in particular insects,
arachnids and nematodes, which are encountered in agriculture, in forestry, in the
protection of stored products and of materials, and in the hygiene sector, and have good
20 plant tolerance and favourable toxicity to warm-blooded animals. They may be
preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include:
25 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.
30 From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera
spp.

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From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanura, for example, Lepisma saccharina. 5
From the order of the Collembola, for example, Onychiurus armatus.
From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. and Schistocerca gregaria. 10
From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
From the order of the Dermaptera, for example, Forficula auricularia. 15
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. and Damalinia spp. 20
From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus
25 intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci,
Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis,
Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera
30 vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,
Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps,

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Lecanium comi, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus
5 piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella,
Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,
Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp.,
Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp.,
Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis,
10 Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella,
Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
15 From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha
dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites
20 sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma
spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrus oryzophilus.
25
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.,
30 Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia
spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys

Le A 35 451-Foreign Countries
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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.
5 From the order of the Siphonaptera, for example, Xenopsylla cheopis and
Ceratophyllus spp.
From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans,
Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis,
10 Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp.,
Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
15 The phytoparasitic nematodes include, for example, Pratylenchus spp., Radopholus
similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
20 If appropriate, the compounds according to the invention can, at certain
concentrations or application rates, also be used as herbicides or microbicides, for example as fungicides, antimycotics and bactericides. If appropriate, they can also be employed as intermediates or precursors for the synthesis of other active compounds.
25 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
30 recombinant methods or by combinations of these methods, including the transgenic
plants and inclusive of the plant cultivars protectable or not protectable by plant

Le A 35 451-Foreign Countries
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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, seeds, roots, tubers and rhizomes. The plant parts also include harvested
5 material, and vegetative and generative propagation material, for example cuttings,
tubers, rhizomes, offsets and seeds.
Treatment according to the invention of the plants and plant parts with the active
compounds is carried out directly or by allowing the compounds to act on the
10 surroundings, environment or storage space by the customary treatment methods, for
example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
15 The active compounds can be converted to the customary formulations, such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound and microencapsulations in polymeric substances.
20 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 to employ for example organic solvents
25 as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene,
toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic
hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic
hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions,
mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and
30 esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or

Le A 35 451-Foreign Countries
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cyclohexanone, strongly polar solvents such as dirnethylformamide and dimethyl sulphoxide, and also water.
As solid carriers there are suitable: 5
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; as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as
10 calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic
and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifiers and/or foam-formers there are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers,
15 alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; as
dispersants there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the
20 form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and
polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other possible additives are mineral and vegetable oils.
25 It is possible to use colorants such as inorganic pigments, for example iron oxide,
titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
30 The formulations generally comprise between 0.1 and 95% by weight of active
compound, preferably between 0.5 and 90%.

Le A 35 451-Foreien Countries
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The active compounds according to the invention can be employed as such or in their
formulations as a mixture with known fungicides, bactericides, acaricides, nematicides
or insecticides in order to increase the activity spectrum or avoid the development of
5 resistance. In many cases synergistic effects are achieved, ie. the efficacy of the mixture
is greater than the efficacy of the individual components.
Favourable examples of co-components in mixtures are the following compounds:
10 Fungicides:
aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine, azaconazole, azoxystrobin,
15 benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl, bialaphos,
binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon,
quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin,
20 chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole,
cyprodinil, cyprofuram,
debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran,
diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,
25 diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon,
dodemorph, dodine, drazoxolon,
ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
30 famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,
fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,

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fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, 5
guazatine,
hexachlorobenzene, hexaconazole, hymexazole,
10 imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine
triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, isovaledione,
kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper
15 naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and
Bordeaux mixture,
mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl,
metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,
20 mildiomycin, myclobutanil, myclozolin,
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin, 25
paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
30
quinconazole, quintozene (PCNB),

Le A 35 451-Foreign Countries
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sulphur and sulphur preparations,
tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole,
5 thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl,
tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemoipri, trifloxystTobm, trtfVurnizote, iTtforaie, trilkonazcAe,
uniconazole, 10
validamycin A, vinclozolin, viniconazole,
zarilamide, zineb, ziram and also
15 Dagger G,
OK-8705,
OK-8801,
20
a-( 1,1 -dimethylethyl)-P-(2-phenoxyethyl)-1H-1,2,4-triazole-1 -ethanol, a-(2,4-dichlorophenyl)-p-fluoro-P-propyl-lH-l,2,4-triazole-l-ethanol, cc-(2,4-dichlorophenyl)-|3-methoxy-a-methyl-1H-1,2,4-triazole-1 -ethanol, oc-(5-methyl-l,3-dioxan-5-yl)-p-[[4-(trifluoromethyl)-phenyl]-methylene]-
25 lH-l,2,4-triazole-l-ethanol,
(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5"(lH-l,2,4-triazol-l-yl)-3-octanone, (E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,
30 1-isopropyl {2-methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-
carbamate,

Le A 35 451-Foreign Countries
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l-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanone-0-(phenylmethyl)-oxime,
l-(2-methyl-l-naphthalenyl)-lH-pyrrol-2,5-dione,
l-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,
5 l-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,
l-[[2-(2,4-dichlorophenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazole,
l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazole,
l-[l-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-lH-imidazole,
l-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,
10 2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-l,3-thiazole-
5-carboxanilide,
2,2-dichloro-N-[l-(4-chlorophenyl)-ethyl]-l-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,
2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,
15 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,
2-(2,3,3-tniodo-2-propenyl)-2H-tetrazole,
2-[(l-methylethyl)-sulphonyl]-5-(trichloromethyl)-l,3,4-thiadiazole,
2-[[6-deoxy-4-0-(4-0-methyl-P-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-
4-methoxy-lH-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,
20 2-aminobutane,
2-bromo-2-(bromomethyl)-pentanedinitrile,
2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridinecarboxamide,
2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,
2-phenylphenol (OPP),
25 3,4-dichloro-l-[4-(difluoromethoxy)-phenyl]-lH-pyrrol-2,5-dione,
3,5-dichloro-N-[cyano[(l-methyl-2-propynyl)-oxy]-methyl]-benzamide,
3-( 1,1 -dimethylpropyl)-1 -oxo-1 H-indene-2-carbonitrile,
3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazole-l-sulphonamide,
30 4-methyl-tetrazolo[ 1,5-a]quinazolin-5(4H)-one,
8-(l,l-dimethylethy])-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decane-2-methanamine,

Le A 35 451-Foreign Countries
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8-hydroxyquinoline sulphate,
9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylichydrazide,
bis-(l-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
cis-l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-cycloheptanol,
5 cis-4-t3-[4-(l,l-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine
hydrochloride,
ethyl [(4-chlorophenyl)-azo]-cyanoacetate, potassium bicarbonate, methanetetrathiol-sodium salt,
10 methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazoIe-5-carboxylate,
methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate, methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate, N-(2,3-dichloro-4-hydroxyphenyl)-1 -methyl-cyclohexanecarboxamide, N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,
15 N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide, N-(4-cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidinamine, N-(4-hexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidinamine, N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,
20 N-(6-methoxy)-3-pyridinyl-cyclopropanecarboxarnide,
N-[2,2,2-trichloro-1 -[(chloroacetyl)-amino]-ethyl]-benzamide,
N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamide,
N-formyl-N-hydroxy-DL-alanine-sodiumsalt,
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
25 O-methyl S-phenyl phenylpropylphosphoramidothioate,
S-methyl 1,2,3-benzothiadiazole-7-carbothioate, spiro[2H]-l-benzopyrane-2,l'(3'H)-isobenzofuran]-3'-one, 4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine

Le A 35 451-Foreign Countries
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Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin,
5 tecloftalam, copper sulphate and other copper preparations.
Insecticides / acaricides / nematicides:
abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-
10 cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,
azamethiphos, azinphos A, azinphos M, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis,
baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb,
15 bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin,
biopermethrin, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb,
20 chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos,
chlorpyrifos, chlorpyrifos M, chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin, clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos, cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, 25
deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,
30 eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate,
ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,

Le A 35 451-Foreign Countries
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fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim,
fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate,
fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,
5 flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,
fubfenprox, furathiocarb,
granulosis viruses,
10 halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,
imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nuclear polyhedrosis viruses, 15
lambda-cyhalothrin, lufenuron,
malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae,
metharhizium flavoviride, methidathion, methiocarb, methoprene, methomyl,
20 methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin,
monocrotophos,
naled, nitenpyram, nithiazine, novaluron,
25 omethoate, oxamyl, oxydemethon M,
Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoate,
phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A,
pirimiphos M, profenofos, promecarb, propargite, propoxur, prothiofos, prothoate,
30 pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion,
pyrimidifen, pyriproxyfen,

Le A 35 451-Foreign Countries
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quinalphos,
ribavirin, 5
salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep, sulprofos,
tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,
tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon, theta-
10 cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam
hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,
15 vamidothion, vaniliprole, Verticillium lecanii,
YI5302,
zeta-cypermethrin, zolaprofos, 20
(lR-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,
(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate, 25
l-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazine-2(lH)-imine,
2-(2-chloro-6-fluorophenyl)-4-[4-(l,l-dimethylethyl)phenyl]-4,5-dihydro-oxazole,
30 2-(acetyloxy)-3-dodecyl-l,4-naphthalenedione,
2-chloro-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

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2-chloro-N-[[[4-(2,2-dichloro-l,l-difluoroethoxy)-phenyl]-amino]-carbonyl]-
benzamide,
3-methylphenyl propylcarbamate,
4-[4-(4-ethoxyphenyl)-4-methylpentyl]-l-fluoro-2-phenoxy-benzene,
5 4-chloro-2-(l,l-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-
3(2H)-pyridazinone,
4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-
3(2H)-pyridazinone,
4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-
10 3(2H)-pyridazinone,
Bacillus thuringiensis strain EG-2348,
[2-benzoyl-1 -(1,1 -dimethylethyl)-hydrazinobenzoic acid,
2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-l-oxaspiro[4.5]dec-3-en-4-ylbutanoate,
[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,
15 dihydro-2-(nitromethylene)-2H-l,3-thiazine-3(4H)-carboxaldehyde,
ethyl [2-[[l,6-dihydro-6-oxo-l-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,
N-(3,4,4-trifluoro-1 -oxo-3-butenyl)-glycine,
N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-
1 H-pyrazole-1 -carboxamide,
20 N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N"-nitro-guanidine,
N-methyl-N'-(l-methyl-2-propenyl)-l,2-hydrazinedicarbothioamide,
N-methyl-N'-2-propenyl-l,2-hydrazinedicarbothioamide,
0,0-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
N-cyanomethyl-4-trifluoromethyl-nicotinamide,
25 3,5-dichloro-l-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-
yloxy)-propoxy]-benzene.
It is also possible to admix other known active compounds, such as herbicides, fertilizers and growth regulators.

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When used as insecticides, the active compounds according to the invention can
furthermore be present in their commercially available formulations and in the use
forms, prepared from these formulations, as a mixture with synergistic agents.
Synergistic agents are compounds which increase the action of the active compounds,
5 without it being necessary for the synergistic agent added to be active itself.
The active compound content of the use forms prepared from the commercially
available formulations can vary within wide limits. The active compound
concentration of the use forms can be from 0.0000001 to 95% by weight of active
10 compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene pests and pests of stored products, the active compound
15 is distinguished by an excellent residual action on wood and clay as well as by a good
stability to alkali on limed substrates.
As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or
20 those obtained by conventional biological breeding, such as crossing or protoplast
fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been
25 explained above.
Particularly preferably, plants of the plant cultivars which are in each case
commercially available or in use are treated according to the invention. Plant
cultivars are understood as meaning plants with novel properties ("traits") which are
30 grown by conventional cultivation, by mutagenesis or by recombinant DNA
techniques. These may be cultivars, biotypes or genotypes.

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Depending on the plant species or plant cultivars, their location and growth
conditions (soils, climate, vegetation period, diet), the treatment according to the
invention may also result in superadditive ("synergistic") effects. Thus, for example,
5 reduced application rates and/or a widening of the activity spectrum and/or an
increase in the activity of the substances and compositions to be used according to
the invention, better plant growth, increased tolerance to high or low temperatures,
increased tolerance to drought or to water or soil salt content, increased flowering
performance, easier harvesting, accelerated maturation, higher harvest yields, better
10 quality and/or a higher nutritional value of the harvested products, better storage
stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.
The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering)
15 which are preferably to be treated according to the invention include all plants which,
in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("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 water or soil salt content, increased flowering performance,
20 easier harvesting, accelerated maturation, higher harvest yields, better quality and/or
a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or
25 viruses, and also increased tolerance of the plants to certain herbicidally active
compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton
30 and oilseed rape. Traits that are emphasized are in particular increased defence of the
plants against insects by toxins formed in the plants, in particular those formed in the

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plants by the genetic material from Bacillus thuringiensis (for example by the genes
CrylA(a), CrylA(b), CrylA(c), CryllA, CrylUA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb
and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants").
Traits which are also particularly emphasized are the increased resistance of plants to
5 fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin,
phytoalexins, elicitors and resistance genes and the correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example
10 the "PAT" gene). The genes which impart the desired traits in question can also be
present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize),
15 StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and
NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape),
20 IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for
example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which
25 cultivars will be developed and/or marketed in the future.
The plants listed can be treated according to the invention in a particularly
advantageous manner with the compounds of the formula I or the active compound
mixtures according to the invention. The preferred ranges stated above for the active
30 compounds or mixtures also apply to the treatment of these plants. Particular

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emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
The active compounds according to the invention act not only against plant, hygiene
5 and stored product pests, but also in the veterinary medicine sector against animal
parasites (ectoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include:
10 From the order of the Anoplurida, for example, Haematopinus spp., Linognathus
spp., Pediculus spp., Phtirus spp. and Solenopotes spp.
From the order of the Mallophagida and the suborders Amblycerina and
Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola
15 spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and
Felicola spp.
From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp.,
20 Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.,
Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca
25 spp., Lipoptena spp. and Melophagus spp.
From the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp.,
30 Rhodnius spp. and Panstrongylus spp.

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From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp.
From the subclass of the Acaria (Acarida) and the orders of the Meta- and
5 Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,
Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.
10 From the order of the Actinedida (Prostigmata) und Acaridida (Astigmata), for
example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., PteroHchus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,
15 Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.
The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits,
20 chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats,
caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc.) should be diminished, so that more economic and easier animal husbandry is possible by use
25 of the active compounds according to the invention.
The active compounds according to the invention are used in the veterinary sector in
a known manner by enteral administration in the form of, for example, tablets,
capsules, potions, drenches, granules, pastes, boluses, the feed-through process and
30 suppositories, by parenteral administration, such as, for example, by injection
(intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by

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nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like. 5
When used for cattle, poultry, pets and the like, the active compounds of the formula
(I) can be used as formulations (for example powders, emulsions, free-flowing
compositions), which comprise the active compounds in an amount of 1 to 80% by
weight, directly or after 100 to 10 000-fold dilution, or they can be used as a
10 chemical bath.
It has furthermore been found that the compounds according to the invention have a strong insecticidal action against insects which destroy industrial materials.
15 The following insects may be mentioned as examples and as preferred - but without
limitation:
Beetles, such as
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium
20 rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Emobius mollis, Priobium
carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus
pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron
spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon
spec. Dinoderus minutus.
25 Hymenopterons, such as
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites, such as
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes
flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes
30 darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristletails, such as Lepisma saccharina.

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Industrial materials in the present connection are to be understood as meaning non¬living materials, such as, preferably, plastics, adhesives, sizes, papers and cards, leather, wood and processed wood products and coating compositions. 5
Wood and processed wood products are materials to be protected, especially preferably, from insect infestation.
Wood and processed wood products which can be protected by the agents according
10 to the invention or mixtures comprising these are to be understood as meaning, for
example:
building timber, wooden beams, railway sleepers, bridge components, boat jetties,
wooden vehicles, boxes, pallets, containers, telegraph poles, wood panelling, wooden
15 windows and doors, plywood, chipboard, joinery or wooden products which are used
quite generally in house-building or in building joinery.
The active compounds can be used as such, in the form of concentrates or generally
customary formulations, such as powders, granules, solutions, suspensions,
20 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,
dispersing agent and/or binder or fixing agent, a water repellent, if appropriate
25 siccatives and UV stabilizers and if appropriate dyestuffs and pigments, and also
other processing auxiliaries.
The insecticidal compositions or concentrates used for the preservation of wood and
wood-derived timber products comprise the active compound according to the
30 invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60%
by weight.

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The amount of the compositions or concentrates employed depends on the nature and
occurrence of the insects and on the medium. The optimum amount employed can be
determined for the use in each case by a series of tests. In general, however, it is
5 sufficient 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 preserved.
Solvents and/or diluents which are used are an organic chemical solvent or solvent
mixture and/or an oily or oil-like organic chemical solvent or solvent mixture of low
10 volatility and/or a polar organic chemical solvent or solvent mixture and/or water,
and if appropriate an emulsifier and/or wetting agent.
Organic chemical solvents which are preferably used are oily or oil-like solvents
having an evaporation number above 35 and a flashpoint above 30°C, preferably
15 above 45°C. Substances which are used as such oily or oil-like water-insoluble
solvents of low volatility are appropriate mineral oils or aromatic fractions thereof, or solvent mixtures containing mineral oils, preferably white spirit, petroleum and/or alkylbenzene.
20 Mineral oils having a boiling range from 170 to 220°C, white spirit having a boiling
range from 170 to 220°C, spindle oil having a boiling range from 250 to 350°C, petroleum and aromatics having a boiling range from 160 to 280°C, terpentine oil and the like, are advantageously employed.
25 In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range from
180 to 210°C or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range from 180 to 220°C and/or spindle oil and/or monochloronaphthalene, preferably a-monochloronaphthalene, are used.
30 The organic oily or oil-like solvents of low volatility which have an evaporation
number above 35 and a flashpoint above 30°C, preferably above 45°C, can be

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replaced in part by organic chemical solvents of high or medium volatility, providing that the solvent mixture likewise has an evaporation number above 35 and a flashpoint above 30°C, preferably above 45°C, and that the insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture. 5
According to a preferred embodiment, some of the organic chemical solvent or
solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is
replaced. Aliphatic organic chemical solvents containing hydroxyl and/or ester and/or
ether groups, such as, for example, glycol ethers, esters or the like, are preferably
10 used.
Organic chemical binders which are used in the context of the present invention are the synthetic resins and/or binding drying oils which are known per se, are water-dilutable and/or are soluble or dispersible or emulsifiable in the organic chemical
15 solvents employed, in particular binders consisting 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, phenolic resin, hydrocarbon resin, such as indene-cumarone resin, silicone resin, drying vegetable oils and/or drying oils and/or physically drying binders based on a natural
20 and/or synthetic resin.
The synthetic resin used as the binder can be employed in the form of an emulsion,
dispersion or solution. Bitumen or bituminous substances can also be used as binders
in an amount of up to 10% by weight. Dyestuffs, pigments, water-repelling agents,
25 odour correctants and inhibitors or anticorrosive agents and the like which are known
per se can additionally be employed.
It is preferred according to the invention for the composition or concentrate to
comprise, as the organic chemical binder, at least one alkyd resin or modified alkyd
30 resin and/or one drying vegetable oil. Alkyd resins having an oil content of more than

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45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
All or some of the binder mentioned can be replaced by a fixing agent (mixture) or a
5 plasticizer (mixture). These additives are intended to prevent evaporation 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 originate from the chemical classes of phthalic acid esters, such as
10 dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters, such as tributyl
phosphate, adipic acid esters, such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amyl stearate, oleates, such as butyl oleate, glycerol ethers or higher molecular weight glycol ethers, glycerol esters and p-toluenesulphonic acid esters.
15 Fixing agents are based chemically on polyvinyl alkyl ethers, such as, for example,
polyvinyl methyl ether or ketones, such as benzophenone or ethylenebenzophenone.
Possible solvents or diluents are, in particular, also water, if appropriate as a mixture
with one or more of the abovementioned organic chemical solvents or diluents,
20 emulsifiers and dispersing agents.
Particularly effective preservation of wood is achieved by impregnation processes on a large industrial scale, for example vacuum, double vacuum or pressure processes.
25 The ready-to-use compositions can also comprise other insecticides, if appropriate,
and also one or more fungicides, if appropriate.
Possible additional mixing partners are, preferably, the insecticides and fungicides
mentioned in WO 94/29 268. The compounds mentioned in this document are an
30 explicit constituent of the present application.

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Especially preferred mixing partners which may be mentioned are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxide and triflumuron, 5
and also fungicides, such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one. 10
The compounds according to the invention can at the same time be employed for protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
15 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 (acorn 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
20 consumption and additionally frequent residence in the dry dock.
Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., in particular fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance. 25
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.
30 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

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bis(trialkyltin) sulphides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I)
oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin
oxide, molybdenum disulphide, antimony oxide, polymeric butyl titanate, phenyl-
(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganese ethylenebis-
5 thiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc
salts and copper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zinc oxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed with, or the concentration of these compounds to be substantially reduced. 10
If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
15 Preferably suitable components in combinations with the antifouling compositions
according to the invention are:
algicides such as
20 2-fert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophen,
diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
fungicides such as 25
benzo[£]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole;
30
molluscicides such as

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fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb; or conventional antifouling active compounds such as
5 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulphone, 2-(N,N-
dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts
of 2-pyridinethiol 1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-
tetrachloro-4-(methylsulphonyl)-pyridine, 2,4,5,6-tetrachloroisophthalonitrile,
tetramethylthiuram disulphide and 2,4,6-trichlorophenylmaleiimide. 10
The antifouling compositions used comprise the active compound 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.
15 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.
20 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,
25 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
30 compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl
resins.

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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 colophonium to allow controlled release of the active
5 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.
10 The active compounds 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 alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against
15 sensitive and resistant species and against all developmental stages. These pests
include:
From the order of the Scorpionidea, for example, Buthus occitanus.
20 From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia
ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
25 From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
30 From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.

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From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda, for example, Geophilus spp.
5 From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma
saccharina, Lepismodes inquilinus.
From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica,
Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta
10 australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,
Supella longipalpa.
From the order of the Saltatoria, for example, Acheta domesticus.
15 From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.
From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp. 20
From the order of the Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
25 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., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
30

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From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera, for example, Ctenocephalides canis,
5 Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymefloptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum. 10
From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
From the order of the Heteroptera, for example, Cimex hemipterus, Cimex
15 lectularius, Rhodinus prolixus, Triatoma infestans.
In the field of household insecticides, they are used alone or in combination with
other suitable active compounds, such as phosphoric acid esters, carbamates,
pyrethroids, growth regulators or active compounds from other known classes of
20 insecticides.
They are used as 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
25 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 according to the invention can also be used as defoliants,
30 desiccants, haulm killers and, especially, as weedkillers. Weeds in the broadest sense
are understood to mean all plants which grow in locations where they are undesired.

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Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in
5 connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
10 Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium,
Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
15
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
20 Monocotvledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,
Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,
25 Scirpus, Setaria, Sorghum.
Monocotvledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
30 However, the use of the active compounds according to the invention is in no way
restricted to these genera, but also extends in the same manner to other plants.

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The active compounds according to the invention are suitable, depending on the
concentration, for the total control of weeds, for example on industrial terrain and rail
tracks, and on paths and areas with and without tree plantings. Similarly, the active
5 compounds according to the invention can be employed for controlling weeds in
perennial crops, for example forests, decorative 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 pastureland, and for the selective control of weeds in
10 annual crops.
The compounds of the formula (I) according to the invention have strong herbicidal
activity and a broad active spectrum when used on the soil and on above-ground parts
of plants. To a certain extent they are also suitable for the selective control of
15 monocotyledonous and dicotyledonous weeds in monocotyledonous and
dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
At certain concentrations or application rates, the active compounds according to the
invention can also be employed for controlling animal pests and fungal or bacterial
20 plant diseases. If appropriate, they can also be used as intermediates or precursors for
the synthesis of other active compounds.
The active compounds can be converted into the customary formulations such as
solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble
25 powders, granules, suspension-emulsion 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,
30 optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or
foam formers.

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If the extender used is water, it is also possible to employ, for example, organic
solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such
as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated
5 aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene
chloride, aliphatic hydrocarbons such as cyclohexane 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 ketone or cyclohexanone, strongly polar solvents such as
10 dimethylformamide and dimethyl sulphoxide, 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 finely divided silica,
15 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, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers
20 such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for
example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
25 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 possible additives are mineral and vegetable oils.
30

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esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,
ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop
(-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),
fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac (-pentyl),
5 flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,
fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop
10 (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-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, mesotrione, metamitron, metazachlor, methabenzthiazuron,
15 metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,
metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen, piperophos,
20 pretilachlor, primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil,
propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac,
25 quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, simazine,
simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,
30 tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.

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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. 5
The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in
10 their formulations, can also be used as mixtures with known herbicides and/or
substances which improve the compatibility with crop plants ("safeners"), finished formulations or tank mixes being possible. Also possible are mixtures with weed¬killers comprising one or more known herbicides and a safener.
15 Possible components 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
20 (-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop
(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinidon
25 (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl),
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, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr,
30 dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam,
dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC,

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Furthermore suitable for the mixtures are known safeners, for example:
AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-
24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole, fluxofenim,
furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191,
5 oxabetrinil, PPG-1292, R-29148.
A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
10
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.
15
The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
20 The amount of active compound used can vary within a relatively wide range. It
depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
25 The substances according to the invention have potent microbicidal activity and can
be employed for controlling undesirable microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
Fungicides can be employed in crop protection for controlling
30 Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes,
Basidiomycetes and Deuteromycetes.

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Bactericides can be employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
5 Some pathogens causing fungal and bacterial diseases which come under the generic
names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae;
10 Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum; 15
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or
20 Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae; 25
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
30 Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

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Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
5 Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(conidia form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus 10
(conidia form: Drechslera, syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
15 Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries; 20
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
25 Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea; 30
Septoria species, such as, for example, Septoria nodorum;

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Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens; 5
Alternaria species, such as, for example, Alternaria brassicae; and
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides. 10
The active compounds according to the invention also have very good fortifying action in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
15 In the present context, plant-fortifying (resistance-inducing) substances are to be
understood as meaning those substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with undesirable microorganisms, they show substantial resistance against these mircroorganisms.
20
In the present case, undesirable microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Accordingly, the substances according to the invention can be used to protect plants for a certain period after the treatment against attack by the pathogens mentioned. The period for which protection is
25 provided generally extends over 1 to 10 days, preferably 1 to 7 days, after the
treatment of the plants with the active compounds.
The fact that the active compounds are well tolerated by plants at the concentrations
required for controlling plant diseases permits the treatment of above-ground parts of
30 plants, of propagation stock and seeds, and of the soil.

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The active compounds according to the invention are also suitable for increasing the yield of crops. In addition, they show reduced toxicity and are well tolerated by plants.
5 At certain concentrations and application rates, the active compounds according to
the invention can also be used as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
10 In the protection of materials, the compounds according to the invention can be
employed for protecting industrial materials against infection with, and destruction by, undesired microorganisms.
Industrial materials in the present context are understood as meaning non-living
15 materials which have been prepared for use in industry. For example, industrial
materials which are intended to be protected by active compounds according to the
invention from microbial change or destruction can be adhesives, sizes, paper and
board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other
materials which can be infected with, or destroyed by, microorganisms. Parts of
20 production plants, for example cooling-water circuits, which may be impaired by the
proliferation of microorganisms may also be mentioned within the scope of the
materials to be protected. Industrial materials which may be mentioned within the
scope of the present invention are preferably adhesives, sizes, paper and board,
leather, wood, paints, cooling lubricants and heat-transfer liquids, particularly
25 preferably wood.
Microorganisms capable of degrading or changing the industrial materials which may
be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms.
The active compounds according to the invention preferably act against fungi, in
30 particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes),
and against slime organisms and algae.

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Microorganisms of the following genera may be mentioned as examples:
Altemaria, such as Alternaria tenuis, 5
Aspergillus, such as Aspergillus niger,
Chaetomium, such as Chaetomium globosum,
10 Coniophora, such as Coniophora puetana,
Lentinus, such as Lentinus tigrinus,
Penicillium, such as Penicillium glaucum, 15
Polyporus, such as Polyporus versicolor,
Aureobasidium, such as Aureobasidium pullulans,
20 Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, such as Trichoderma viride,
Escherichia, such as Escherichia coli, 25
Pseudomonas, such as Pseudomonas aeruginosa, and
Staphylococcus, such as Staphylococcus aureus.
30 Depending on their particular physical and/or chemical properties, the active
compounds can be converted into the customary formulations, such as solutions,

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emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
5 These formulations are produced in a known manner, for example by mixing the
active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, 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 to employ, for example, organic solvents as auxiliary solvents.
10 Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or
alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl
15 ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as
dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and
20 carbon dioxide. Suitable solid carriers are: for example ground natural minerals such
as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided 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
25 else synthetic granules of inorganic and organic meals, and granules of organic
material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
30 arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example
lignosulphite waste liquors and methylcellulose.

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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
5 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 dyestuffs such as alizarin dyestuffs,
10 azo dyestuffs and metal phthalocyanine dyestuffs, 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%.
15
The active compounds according to the invention can be used as such or in their formulations, also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden, for example, the activity spectrum or to prevent development of resistance. In many cases, synergistic effects are obtained,
20 i.e. the activity of the mixture is greater than the activity of the individual
components.
Examples of suitable mixing components are the following:
25 Fungicides:
aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine, azaconazole, azoxystrobin,

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benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
5 calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon,
quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorolhalonU- chlozDiinate^ cJozytecon, cufraneb, cymoxani), cyproconazoie, cyprodinil, cyprofuram,
10 debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran,
diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon.,
15 edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,
famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,
fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,
fluazinam, flumetover, fluor0mide, fluquinconazole, flurprimidol, flusilazole,
20 flusulfamide, flutolanil, flutriaf0l, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,
fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
guazatine, 25
hexachlorobenzene, hexaconazole, hymexazole,
imazalil, imibenconazole, irnjn0ctadine, iminoctadine albesilate, iminoctadine
triacetate, iodocarb, ipcona*0le, iprobenfos (IBP), iprodione, irumamycin,
30 isoprothiolane, isovaledione,

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kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture,
5 mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl,
metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, 10
ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,
paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin,
pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,
15 propamocarb, propanosine-sodium, propiconazole, propineb, pyraclostrobin,
pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
quinconazole, quintozene (PCNB),
20 sulphur and sulphur preparations,
tebuconazole, tecloftalam, tecnazene, tetcycJacis, tetraconazole, thiabendazole,
thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl,
tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole,
25 tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
uniconazole,
validamycin A, vinclozolin, viniconazole, 30
zarilamide, zineb, ziram and also
~3-/_

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Dagger G, OK-8705, OK-8801, 5
a-( 1,1 -dimethylethyl)-|3-(2-phenoxyethyl)-1H-1,2,4-triazole-1 -ethanol, '
a-(2,4-dichlorophenyl)-P-fluoro-3-propyl-lH-l,2,4-triazole-l-ethanol,
a-(2,4-dichlorophenyl)-a-methoxy-a-methyl-lH-l,2,4-triazole-l-ethanol,
a-(5-methyl-l,3-dioxan-5-yl)-p-[[4-(trifluoromethyl)-phenyl]-methylene]-lH-l,2,4-
10 triazole-1-ethanol,
(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanone, (E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,
isopropyl {2-methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-
15 carbamate,
l-(2,4-dichlorophenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanoneO-(phenylmethyl)-oxime,
1 -(2-methyl-1 -naphthalenyl)- lH-pyrrole-2,5-dione,
l-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrro]idinedione,
20 l-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,
l-[[2-(2,4-dichlorophenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazole,
l-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazole,
l-[l-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-lH-imidazole,
l-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole, 25
2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-l,3-thiazole-
5-carboxanilide,
2,2-dichloro-N-[l-(4-chlorophenyl)-ethyl]-l-ethyl-3-methyl-
cyclopropanecarboxamide,
30 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

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2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide, 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,
2-[(l-methylethyl)-sulphonyl]-5-(trichloromethyl)-l,3,4-thiadiazole,
5 2-[[6-deoxy-4-0-(4-0-methyl-p-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-
4-methoxy-lH-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, 2-aminobutane,
2-bromo-2-(bromomethyl)-pentanedinitrile,
2-chloro-N-(2,3-dihydro-l, 1,3-trimethyl- lH-inden-4-yl)-3-pyridinecarboxamide,
10 2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,
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,
15 3-( 1,1 -dimethylpropyl-1 -oxo-1 H-indene-2-carbonitrile,
3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,
4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazole-l-sulphonamide,
4-methyl-tetrazolo[l,5-a]quinazolin-5(4H)-one,
20 8-(l,l-dimethylethyl)-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decane-2-methaneamine,
8-hydroxyquinoline sulphate,
9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,
25 bis-(l-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,
ci s-1 -(4-chlorophenyl)-2-( 1H-1,2,4-triazol-1 -yl)-cycloheptanol, cis-4-[3-[4-(l,l-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride,
30 ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

Le A 35 451-Foreign Countries
-73-
potassium hydrogen carbonate,
methanetetrathiol sodium salt,
methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate,
5 methyl N-(2,6-dimethyIphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,
methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate, N-(2,3-dichloro-4-hydroxyphenyl)-l-methyl-cyclohexanecarboxamide, N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide, N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,
10 N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,
N-(4-cyclohexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, N-(4-hexylphenyl)-l,4,5,6-tetrahydro-2-pyrimidineamine, N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide, N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,
15 N-[2,2,2-trichloro-l-[(chloroacetyl)-amino]-ethyl]-benzamide,
N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N'-methoxy-methaneimidamide, N-formyl-N-hydroxy-DL-alanine-sodium salt,
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
20 O-methyl S-phenyl phenylpropylphosphoramidothioate,
S-methyl l,2,3-benzothiadiazole-7-carbothioate, spiro[2H]-l-benzopyrane-2,r(3'H)-isobenzofuran]-3'-one, 4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine. 25
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin,
octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin,
30 tecloftalam, copper sulphate and other copper preparations.

Le A 35 451-Foreign Countries
-74-
Insecticides / acaricides / nematicides:
abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-
cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,
5 azamethiphos, azinphos A, azinphos M, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis,
baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb,
bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin,
10 biopermethnn, bistrifluron, BPMC, bromophos A, bufencarb, buprofezin,
butathiofos, butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb,
chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos,
15 chlorpyrifos, chlorpyrifos M, chlovaporthrin, chromafenozide, cis-resmethrin,
cispermethrin, clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos, cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
20 deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon,
dichlorvos, dicofol, diflubenzuron, dimethoat, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,
eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate,
25 ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim,
fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate,
fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,
30 flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,
fubfenprox, furathiocarb,

Le A 35 451-Foreign Countries,
-75-granulosis viruses,
halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,
5 imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
nuclear polyhidrosis viruses,
lambda-cyhalothrin, lufenuron,
10
malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, monocrotophos,
15
naled, nitenpyram, nithiazine, novaluron,
omethoate, oxamyl, oxydemethon M,
20 Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoate,
phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A, pinmiphos M, profenofos, pronvecarb, propargite, propoxur, prothiofos, prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen, pyriproxyfen,
25
quinalphos,
ribavirin,
30 salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep, sulprofos,

Le A 35 451-Foreign Countries
-76-
tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron,
tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon theta-
cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam
hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,
5 triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon,
triflumuron, trimethacarb,
vamidothion, vaniliprole, Verticillium lecanii,
10 YI5302
zeta-cypermethrin, zolaprofos
(lR-cis)-[5-(phenylmethyl)-3-furanyl]-methyI-3-[(dihydro-2-oxo-3(2H)-
15 furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,
(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,
l-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-l,3,5-triazine-
20 2(lH)-imine,
2-(2-chloro-6-fluorophenyl)-4-[4'(l,l-dimethylethyl)phenyl]-4,5-dihydro-oxazole,
2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,
2-chloro-N-[[[4-(l-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,
25 2-chloro-N-[[[4-(2,2-dichloro-l,l-difluoroethoxy)-phenyl]-amino]-carbonyl]-
benzamide,
3-methylphenyl propylcarbamate,
4-[4-(4-ethoxyphenyl)-4-methylpentyl]-l-fluoro-2-phenoxy-benzene,
4-chloro-2-(l,l-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-
30 3(2H)-pyridazinone,

Le A 35 451-Foreign Countries
-77-
4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-
pyridazinone,
4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-
pyridazinone,
5 Bacillus thuringiensis strain EG-2348,
[2-benzoyl-l-(l,l-dimethylethyl)-hydrazinobenzoic acid,
2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-l-oxaspiro[4.5]dec-3-en-4-yl butanoate,
[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,
dihydro-2-(nitromethylene)-2H-l,3-thiazine-3(4H)-carboxaldehyde,
10 ethyl [2-[[l,6-dihydro-6-oxo-l-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,
N-(3,4,4-trifluoro-l-oxo-3-butenyl)-glycine,
N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-lH-
pyrazole-1 -carboxamide,
N-[(2-chloro-5-thiazolyl)methyl]-N'-methyl-N"-nitro-guanidine,
15 N-methyl-N'-(l-methyl-2-propenyl)-l,2-hydrazinedicarbothioamide,
N-methyl-N'-2-propenyl-l,2-hydrazinedicarbothioamide,
0,0-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,
N-cyanomethyl-4-trifluoromethyl-nicotinamide,
3,5-dichloro-l-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-
20 2-yloxy)-propoxy]-benzene.
A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, is also possible.
25 In addition, the compounds of the formula (I) according to the invention also have
very good antimycotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and
30 Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes,

Microsporon species such as Microsporon canis and audouinii. The list of these fungi by no means limits the mycotic spectrum covered, but is only for illustration.
The active compounds can be used as such, in the form of their formulations or the use
5 forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable
powders, pastes, soluble powders, dusts and granules. Application is carried out in a
customary manner, for example by watering, spraying, atomizing, broadcasting,
dusting, foaming, spreading, etc. It is furthermore possible to apply the active
compounds by the ultra-low-volume method, or to inject the active compound
10 preparation or the active compound itself into the soil. It is also possible to treat the
seeds of the plants.
When using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the kind
15 of application. For the treatment of parts of plants, the active compound application
rates are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seed dressing, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. For the treatment of the soil, the active compound application rates
20 are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.

Accordingly, the present invention relates to compounds of the formula (I)

in which
W represents cyano, halogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl or haloalkoxy,
X represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Y represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
-A-B- represents the groups

G represents halogen or nitro,
R1 represents Ci-C6-alkyl,
R3 represents hydrogen or Ci-C4-alkyl,
and
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).

Accordingly the present invention also relates to a process for preparing compounds of the formula (I) as claimed in claim 1, characterized in that, to obtain
A) compounds of the formulae (1-1) to (1-3)

in which
A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents halogen,
compounds of the formulae (II-1) to (II-3)

in which
A, B, Q, W, X, Y, Z and R3 are as defined above,
are reacted with halogenating agents in the presence of a solvent and, if appropriate, in the presence of a radical initiator;
B) compounds of the formulae (1-1) to (1-3)


in which
A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents nitro,
compounds of the formulae (II-1) to (II-3),

in which
A, B, Q, W, X, Y, Z and R3 are as defined above
are reacted with nitrating agents, such as, for example, faming nitric acid, in the presence of a solvent.
The preparation and the use of the active compounds according to the invention is illustrated by the examples below.

Le A 35 451-Foreign Countries
-79-Preparation Examples Example I-l-a-1
5
0.96 g of the tetramic acid of Example I-l-a-16 (WO 98/05638) is initially charged in 10 ml of anhydrous chloroform and cooled to 0°C. 0.265 ml (1.1 eq., 3.3 mmol) of sulphuryl chloride is added, and the mixture is stirred at 0°C for another 30 min. 10
5 ml of saturated NaHC03 solution are added and the organic phase is separated off, dried and concentrated under reduced pressure using a rotary evaporator.
Yield: 0.513 g (48% of theory), m.p. 225°C. 15

Le A 35 451-Foreign Countries
-80-Example No. I-l-a-66

5 At room temperature, 0.44 g (7 mmol) of fuming nitric acid is added to 1.2 g of the
compound of Preparation Example I-l-a-4 from EP-A-915 846 in 60 ml of anhydrous chloroform, and the mixture is stirred at room temperature for another 30 minutes.
The reaction solution is poured into 50 ml of ice-water and the organic phase is
10 separated off, extracted with dichloromethane and dried, and the solvent is distilled
off.
The product is purified by column chromatography (silica gel, dichloromethane/ethyl acetate 3:1). 15
Yield: 0.9 g (64% of theory), m.p. 150°C.
Analogously to Examples (I-l-a-1) and (I-l-a-66) and in accordance with the general
preparation procedures, the following examples of formulae (I-l-a) to (I-l-c) are
20 obtained:


Le A 35 451-Foreign Countries
-81-Table 1


Le A 35 451-Foreign Countries
-82-
Table 1 (continued)


Le A 35 451-Foreijgn Countries
-83-Table 1 (continued)


Le A 35 451-Foreign Countries
-84-Table 2

5

Le A 35 451-Foreign Countnes
-85-Table 3


Le A 35 451-Foreign Countries
-86-Example I-2-a-l

5 With ice-cooling, a solution of sulphuryl chloride (0.81 g) in 10 ml of anhydrous
chloroform is added dropwise to a solution of the compound of Example I-2-a-3 (WO 97/01535) (0.95 g) in 20 ml of anhydrous chloroform, and the mixture is stirred at room temperature for 10 hours.
10 The reaction mixture is then washed with water, saturated sodium bicarbonate
solution and saturated sodium chloride solution and dried.
Yield: 1.16 g (99.2% of theory), log P (pH 2.3) 4.07

Le A 35 451-Foreign Countries
-87-Example I-2-a-2

5 At room temperature, 0.252 g (4 mmol) of fuming nitric acid is added dropwise to
0.633 g (2 mmol) of the compound of Preparation Example I-2-a-3 from WO 97/01535 in 10 ml of anhydrous chloroform, and the mixture is stirred at room temperature for another 30 minutes.
10 The reaction solution is washed with water, the organic phase is separated off and
dried and the solvent is distilled off. Cartridge chromatography on silica gel using methylene chloride/acetone 19:1 gives 0.4 g (51% of theory) of an isomer mixture, log P 4.17; 4.42.
15 Analogously to Examples (I-2-a-l) and (I-2-a-2) and in accordance with the general
preparation procedures, the following examples of the formulae (I-2-a) to (I-2-c) are obtained:
Table 4
20


Le A 35 451-Foreign Countries
-92-
Table B
Plant-damaging nematodes
Meloidogyne test
Active compounds Concentration of Kill rate in %
active compound in after 14d
ppm
5

Le A 35 451-Foreign Countries
-95-
Example P
Phaedon larvae test
5 Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 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
10 concentrate is diluted with emulsifier-containing water to the desired concentration.
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 (Phaedon cochleariae) while leaves are still moist. 15
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.
20 In this test, for example, the following compounds of the Preparation Examples show
good activity:

Le A 35 451-Foreign Countries
-97-
Example E
Plutella test
5 Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 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
10 concentrate is diluted with emulsifier-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the diamondback moth (Plutella xylostella) while leaves are still moist. 15
After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
In this test, for example, the following compounds of the Preparation Examples show
20 good activity:

Le A 35 451-Foreign Countries
-98-
Table E
Plant-damaging insects
Plutella test
Active compounds Concentration of Kill rate in %
active compound in after 7d
ppm
Ex. I-l-a-28 500 100
Ex. I-l-c-2 500 100
Ex. I-l-c-3 500 100
5

Le A 35 451-Foreign Countries
-99-
Example F
Spodoptera frugiperda test
5 Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 2 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
10 concentrate is diluted with emulsifier-containing water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the army worm (Spodoptera frugiperda) while leaves are still moist. 15
After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
In this test, for example, the following compounds of the Preparation Examples show
20 good activity:

Le A 35 451-Foreign Countries
-100-
Table F
Plant-damaging insects
Spodoptera frugiperda test
Active compounds Concentration of Kill rate in %
active compound in after 7d
ppm

Ex. I-l-a-3 500 100
Ex. I-l-a-7 500 100
Ex.I-l-a-8 500 100
Ex. I-l-a-23 500 100
Ex. I-l-a-47 500 100
Ex. I-l-a-48 500 100

Le A 35 451-Foreign Countries
-101-
Example G
Tetranychus test (OP-resistant/dip treatment)
5 Solvent: 7 parts by weight of dimethylformamide
Emulsifier. 2 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
10 concentrate is diluted with emulsifier-containing water to the desired concentration.
Bean plants (Phaseolus vulgaris) which are heavily infested by all stages of the greenhouse rat spider mite (Tetranychus urticae) are dipped into a preparation of active compound of the desired concentration. 15
After the desired period of time, the activity in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
20 In this test, for example, the following compounds of the Preparation Examples show
good activity:

Le A 35 451-Foreign Countries
-102-
Table G
Plant-damaging mites
Tetranychus test (OP-resistant/dip treatment)
Active compounds Concentration of Kill rate in %
active compound in after 7d
ppm

Ex. I-l-a-2 100 98
Ex. I-l-a-5 100 95
Ex. I-l-a-8 100 100
Ex. I-l-a-16 100 100
Ex.I-l-a-22 100 100
Ex. I-l-a-24 100 100
Ex. I-l-b-1 100 95
Ex. I-l-b-5 100 90
Ex. I-l-a-41 100 95

Le A 35 451-Foreign Countries
-103 -
Example H
Test for persistency: Aphis gossypii (root-systemic action)
5 Solvent: 4 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 amounts of solvent and emulsifier, and the
10 concentrate is diluted with water to the desired concentration.
The preparation of active compound is mixed intimately with the soil. The stated
concentration refers to the amount of active compound per volume unit of soil (mg/1).
The treated soil is filled into pots, and into these pots is planted cotton at the
15 cotyledon stage. In this way, the active compound can be taken up from the soil into
the roots of the plants and be transported into the leaves. After the stated number of days, cotton aphids (Aphis gossypii) are, in infection chambers, placed on the leaves.
After the desired period of time, the kill in % is determined. 100% means that all
20 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 good activity:

Le A 35 451-Foreign Countries
-104-
Table H
Plant-damaging insects
Test for persistency: Aphis gossypii (root-systemic action)
Active compounds Concentration of Kill rate in % after 7d
active compound inppm
5

Le A 35 451-Foreign Countries
-105-
Example I
Test for persistency: Myzus persicae (root-systemic action)
5 Solvent: 4 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 amounts of solvent and emulsifier, and the
10 concentrate is diluted with water to the desired concentration.
The preparation of active compound is mixed intimately with the soil. The stated
concentration refers to the amount of active compound per volume unit of soil (mg/1).
The treated soil is filled into pots, and into these pots is planted pre-germinated broad
15 beans. In this way, the active compound can be taken up from the soil into the roots
of the plants and be transported into the leaves. After the stated number of days, peach aphids (Myzus persicae) are, in infection chambers, placed on the leaves.
After the desired period of time, the kill in % is determined. 100% means that all
20 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 good activity:

Le A 35 451-Foreign Countries
-106-
Table I
Plant-damaging insects
Test for persistency: Myzus persicae (root-systemic action)
Active compounds Concentration of Kill rate in % after 7d
active compound in
ppm

Ex. I-2-a-l Infection after: 7d 2id 35d
4 ppm 100 95 0
Ex. I-l-c-1 Infection after: 7d 21d 35d
4 ppm 100 100 100
Ex. I-l-c-2 Infection after: 7d 21d 35d
4 ppm 100 100 99
Ex. M-c-3 Infection after: 7d 21d 35d
4 ppm 99 100 99

Le A 35 451-Foreign Countries
-107-
Example J
Post-emergence test
Solvent: 5 parts by weight of acetone
5 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
10 concentration.
Test plants of a height of 5-15 cm are 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
15 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.
20 The figures denote:
0% = no effect (=like untreated control)
100% = total destruction

Le A 35 451-Foreign Countries
-108-Example K
Pre-emergence test
5 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
10 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
15 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 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in
20 comparison to the development of the untreated control.
The figures denote:
0% = no effect (like untreated control)
100% = total destruction
25

Le A 35 451-Foreign Countries
-109-
pre-emergence/ g of Alopecurus Avena fatua Echinochloa Setaria Amaranthus Sinapis
greenhouse ai/ha

pre-emergence/ g of Sugar beet Alopecurus Avena fatua Echinochloa Setaria Sinapis
greenhouse ai/ha

post-emergence/ g of Alopecurus Avena fatua Echinochloa Setaria Amaranthus Sinapis
greenhouse ai/ha


Le A 35 451-Foreign Countries
-110-
post-emergence/ g of ai/ha Sugar beet Alopecurus Avena fatua Echinochloa Setaria Sinapis greenhouse


Le A 35 451-Foreign Countries
-111-
Example L
Critical concentration test/soil insects - treatment of transgenic plants
5 Test insect: Diabrotica balteata - larvae in soil
Solvent: 7 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
10 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.
15 The preparation of active compound is poured onto the soil. The concentration of the
active compound in the preparation is virtually immaterial, only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/1), matters. The soil is filled into 0.25 1 pots, and these are allowed to stand at 20°C.
20 Immediately after the preparation, 5 pre-germinated maize corns of the soltivar
YIELD GUARD (trademark of Monsanto Comp., USA) are placed into each pot. After 2 days, the corresponding test insects are placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined by counting the number of maize plants that emerged (1 plant = 20% activity).

Le A 35 451-Foreign Countries
-112-
Example M
Heliothis virescens test - treatment of transgenic plants
5 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 and the stated amount of
10 emulsifier, and the concentrate is diluted with water to the desired concentration.
Soybean shoots (Glycine max) of the soltivar Roundup Ready (trade name 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
15 caterpillar Heliothis virescens while the leaves are still moist.
After the desired period of time, the kill of the insects is determined.

WE CLAIM:
1. Compounds of the formula (I)

in which
W represents cyano, halogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl or haloalkoxy,
X represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Y represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
-A-B- represents the groups

G represents halogen or nitro, R1 represents C1-C6-alkyl,

R3 represents hydrogen or C1-C4-alkyl,
and
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
2. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group
c)

W represents halogen or alkyl,
X represents hydrogen, halogen or alkyl,
Y represents hydrogen, halogen or alkyl,
Z represents hydrogen, halogen or alkyl,
where at least one of the radicals W, X and Y represents alkyl and at least one of the radicals W, X and Y represents halogen,
G represents halogen or nitro,
R2 and R3 independently of one another represent hydrogen or C1-C4-alkyl and

Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
3. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group
a)
a) —CH—CH— , where OR1
W represents halogen, Ci-C6-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy or cyano
X represents hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy or cyano,
Y represents hydrogen, halogen, Ci-C6-alkyl, Ci-C6-alkoxy, C1-C4-haloalkyl, Ci-C4-haloalkoxy or cyano,
Z represents hydrogen, halogen, C1-C6-alkyl, Ci-Ce-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy or cyano,
G represents halogen or nitro,
R1 represents C1-C6-alkyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).

4. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group

W represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl, Ci-C2-haloalkoxy or cyano
X represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkoxy,
Y represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C2-haloalkyl, Ci-C2-haloalkoxy or cyano
Z represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4 alkoxy, C1-C2-haloalkyl, C1-C4-haloalkoxy or cyano
G represents chlorine, bromine or nitro,
R1 represents C1-C4-alkyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
5. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group

a) ■
W represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
X represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
Z represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
G represents chlorine, bromine or nitro,
R1 represents methyl, ethyl, propyl, isopropyl, butyl or isobutyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1) and together with oxygen represents the cycle (2).
6. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group

a)
W represents methyl, ethyl, chlorine, bromine, methoxy, trifluoromethyl or trifluoromethoxy,
X represents hydrogen, chlorine, methyl or ethyl,
Y represents hydrogen, chlorine, bromine, methyl, t-butyl, trifluoro methoxy, trifluoromethyl or cyano,
Z represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy or trifluoromethyl,
G represents chlorine or nitro,
R1 represents methyl or ethyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1).
7. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group
b) -O-CH where
W represents halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C4-haloalkyl, C1-C4—haloalkoxy or cyano

X represents hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-alkoxy, C1-C4-halo-alkyl, C1-C4-haloalkoxy or cyano
Y represents hydrogen, halogen, C1-C6-alkyl, Ci-Ce-alkoxy, C1-C4-halo-
alkyl, C1-C4-haloalkoxy or cyano
Z represents hydrogen, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-halo-alkyl, C1-C4-haloalkoxy or cyano
G represents halogen or nitro,
R3 represents hydrogen,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
8. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group
b) -O-CH2- where
W represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy Ci-C2-haloalkyl, C1-C2-haloalkoxy or cyano,
X represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl or C1-C4-alkoxy,
Y represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4
alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano,
Z represents hydrogen, fluorine, chlorine, bromine,C1-C4-alkyl, C1-C4 alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy or cyano,

G represents chlorine, bromine or nitro,
R3 represents hydrogen,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
9. Compounds of the formula (I) as claimed in claim 1 in which A-B represents the group
b) -0-CH2-, where
W represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
X represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
Z represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or cyano,
G represents chlorine, bromine or nitro,
R3 represents hydrogen,
Q together with NH represents the cycle (1) and together with oxygen represents the cycle (2).

10. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
b) -0-CH2-, where
W represents chlorine, bromine, methyl or ethyl,
X represents hydrogen, chlorine, methyl or ethyl,
Y represents hydrogen, chlorine, bromine, methyl or ethyl,
Z represents hydrogen, chlorine or methyl,
G represents chlorine,
R3 represents hydrogen,
Q together with NH represents the cycle (1).
11. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
c) , where
W represents chlorine, bromine, methyl or ethyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine or bromine,
Z represents hydrogen or chlorine,

G represents halogen or nitro,
R2 represents hydrogen or C1-C4-alkyl,
R3 represents hydrogen or C1-C4-alkyl,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).
12. Compounds of the formula (1) as claimed in claim 1 in which A-B represents the group
c) —CH—O— , where R2
W represents chlorine or methyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine or bromine, Z represents hydrogen or chlorine,
G represents chlorine, bromine or nitro,
R2 represents hydrogen, methyl or ethyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1), together with oxygen represents the cycle (2) and together with sulphur represents the cycle (3).

13. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
c) —CH—O— . where R2
W represents chlorine or methyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine or bromine,
Z represents hydrogen or chlorine,
G represents chlorine, bromine or nitro,
R2 represents hydrogen or methyl,
R3 represents hydrogen,
Q together with NH represents the cycle (1) and together with oxygen represents the cycle (2).
14. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
c) —CH—O— , where R2
W represents chlorine or methyl,
X represents chlorine, methyl or ethyl,

Y represents chlorine or bromine,
Z represents hydrogen or chlorine,
G represents chlorine,
R2 represents hydrogen,
R3 represents hydrogen or methyl,
Q together with NH represents the cycle (1).
15. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
a) —CH—O— , where
R1
W represents methyl,
X represents hydrogen, methyl or chlorine,
Y represents hydrogen, methyl, chlorine or bromine,
Z represents hydrogen, methyl or chlorine,
G represents chlorine or nitro,
R1 represents methyl or ethyl,
R3 represents hydrogen,

Q together with oxygen represents the cycle (2).
16. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
b) -0-CH2-, where
W represents methyl,
X represents hydrogen, methyl or chlorine,
Y represents hydrogen, methyl, chlorine or bromine,
Z represents hydrogen, methyl or chlorine,
G represents chlorine or nitro,
R3 represents hydrogen,
Q together with oxygen represents the cycle (2).
17. Compounds of the formula (I) as claimed in claim 1 in which A-B
represents the group
c) —CH—O— where
W represents methyl,
X represents hydrogen,
Y represents methyl,
Z represents methyl,

G represents chlorine,
R2 represents hydrogen,
R3 represents hydrogen,
Q together with oxygen represents the cycle (2).
18. Process for preparing compounds of the formula (I) as claimed in claim 1, characterized in that, to obtain
A) compounds of the formulae (1-1) to (1-3)

in which
A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents halogen,
compounds of the formulae (II-1) to (II-3)


in which
A, B, Q, W, X, Y, Z and R3 are as defined above,
are reacted with halogenating agents in the presence of a solvent and, if appropriate, in the presence of a radical initiator;
B) compounds of the formulae (1-1) to (1-3)

in which
A, B, Q, W, X, Y, Z and R3 are as defined above
and
G represents nitro,
compounds of the formulae (II-1) to (II-3),


in which
A, B, Q, W, X, Y, Z and R3 are as defined above
are reacted with nitrating agents, such as, for example, fuming nitric acid, in the presence of a solvent.
19. Pesticides, herbicides and fungicides, characterized in that they comprise 0.1 to 95 % of at least one compound of the formula (I) as claimed in claim 1.
20. Process for preparing pesticides, herbicides and fungicides, characterized in that 0.1 to 95 % of compounds of the formula (I) as claimed in claim 1 are mixed with extenders and/or surfactants of the kind as herein described.
Dated this September 09, 2002.
(SHUKADEV KHURAIJAM)
OF REMFRY AND SAGAR
ATTORNEY FOR THE APPLICANTS

Documents:

815-mum-2002-cancelled page(2-11-2007).pdf

815-mum-2002-claim(granted)-(2-11-2007).doc

815-mum-2002-claim(granted)-(2-11-2007).pdf

815-mum-2002-correspondence(19-11-2007).pdf

815-mum-2002-correspondence(ipo)-(12-10-2007).pdf

815-mum-2002-form 1(9-9-2002).pdf

815-mum-2002-form 13(19-11-2007).pdf

815-mum-2002-form 18(15-12-2005).pdf

815-mum-2002-form 2(granted)-(2-11-2007).doc

815-mum-2002-form 2(granted)-(2-11-2007).pdf

815-mum-2002-form 3(19-2-2002).pdf

815-mum-2002-form 3(9-9-2002).pdf

815-mum-2002-form 5(9-9-2002).pdf

815-mum-2002-form-pct-ipea-409(9-9-2002).pdf

815-mum-2002-form-pct-isa-210(9-9-2002).pdf

815-mum-2002-petition under rule 137(20-2-2007).pdf

815-mum-2002-petition under rule 138(20-2-2007).pdf

815-mum-2002-power of authority(19-2-2007).pdf

815-mum-2002-power of authority(9-9-2002).pdf


Patent Number 214127
Indian Patent Application Number 815/MUM/2002
PG Journal Number 13/2008
Publication Date 28-Mar-2008
Grant Date 04-Feb-2008
Date of Filing 09-Sep-2002
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368, LEVERKUSEN,
Inventors:
# Inventor's Name Inventor's Address
1 REINER FISCHER NELLY-SACHS-STR. 23, 40789 MONHEIM.
2 DIETER FEUCHT ACKERWEG 9, 40789 MONHEIM,
3 THOMAS BRETSCHMEIDER TALSTR 31, 53677 LOHMAR
4 UDO RECKMANN RONTGENSTRASSE 18, 50823 KOLN.
5 MARK WILHELM DREWES 38, 40764 LANGENFELD,
6 ASTRID ULLMANN MEROWINGERSTR. 31, 50677 KOLN.
7 CHRISTOPH DRDELEN UNTERBUSCHERHOF 15, 42799 LEICHLINGEN.
PCT International Classification Number C07D 209/54
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 101 46 910.1 2001-09-24 Germany