AU8210398A - O-benzyl oxime ether derivatives and their use as pesticides - Google Patents

Description

WO 98/54126 PCT/EP98/03074 -1 O-BENZYL OXIME ETHER DERIVATIVES AND THEIR USE AS PESTICIDES The invention relates to a compound of formula Z RO Y NO, AR7 K (R)n 'N IE / ' (), R3 G R4 (Rs)q wherein either X is CH or N, Y is OR, and Z is O, or X is N, Y is NHRB and Z is O, S or S(=O);

R

1 is C 1

-C

4 alkyl;

R

2 is C 2

-C

4 alkyl or C3-C 6 cycloalkyl;

R

3 and R 4 are each independently of the other H, C 1

-C

4 alkyl, C 1

-C

4 alkoxy, OH, CN, NO 2 , a (C1-C 4 alkyl) 3 -Si group, the alkyl groups being the same or different, halogen, (C-C4 alkyl)S(=O)m, (halo-C1-C 4 alkyl)S(=O)m, halo-Cl-C 4 alkyl or halo-Cl-C 4 alkoxy;

R

8 is H or C 1

-C

4 alkyl;

R

9 is methyl, fluoromethyl or difluoromethyl; m is 0, 1 or 2; A is a direct bond, C-Cloalkylene, -C(=O)-, -C(=S)- or halo-Cl-C 10 alkylene and

R

7 is a radical Rio; or A is C 1 -Co 10 alkylene, -C(=O)-, -C(=S)- or halo-C 1 -Co 10 alkylene and

R

7 is -CN, ORo 10 , N(Ro 10

)

2 , the radicals Rio being the same or different, or -S(=O)pRio; p is 0, 1 or 2; G is O, S or -O-CH 2 -, wherein the -CH 2 group is bonded to the ring denoted by K; Rs and R 6 are C 1

-C

6 alkyl, halo-C 1

-C

6 alkyl, C3-C 6 cycloalkyl, halo-C 3

-C

6 cycloalkyl, C1-C6. alkoxy, halo-C 1

-C

6 alkoxy, C-C 6 alkylthio, halo-Cl-Cealkylthio, C 1

-C

6 alkylsulfynyl, halo C1-C 6 alkylsulfynyl, C-C 6 alkylsulfonyl, halo-C-C 6 alkylsulfonyl, C1-C 6 alkylsulfonyloxy, halo-C 1

-C

6 alkylsulfonyloxy, C1-C 6 alkoxy-C 1

-C

6 alkyl, halo-C 1

-C

6 alkoxy-Cs-Cealkyl, Cl-C 6 alkylthio-C 1

-C

6 alkyl, halo-C 1 -Cealkylthio-C 1

-C

6 alkyl, Cj-C 6 alkylsulfynyl-C 1

-C

6 alkyl, halo-C-Cealkylsulfynyl-C l

-C

6 alkyI, C1-C 6 alkylsulfonyl-C 1 -C6alkyl, halo-C 1

-C

6 alkyl- WO 98/54126 PCT/EP98/03074 -2 sulfonyl-C 1

-C

6 alkyl, C 1-C 6 alkylcarbonyl, halo-C 1

-C

6 alkylcarbonyl, Cl-C 6 alkoxycarbonyl, halo-C 1

-C

6 alkoxycarbonyl, C 1

-C

6 alkylaminocarbonyl, C 1

-C

4 alkoxyiminomethyl, di(Cl-C 6 alkyl)aminocarbonyl, the alkyl groups being the same or different; Cl-C 6 alkyl aminothiocarbonyl, di(Cl-C 6 alkyl)aminothiocarbonyl, the alkyl groups being the same or different; C 1

-C

6 alkylamino, di(C 1

-C

6 alkyl)amino, the alkyl groups being the same or different; halogen, NO 2 , CN, thioamido, trimethylsilyl, CH 2 Si(C 1

-C

4 alkyl) 3 , the alkyl groups being the same or different; an unsubstituted or mono- to tetra-substituted Cl-C 4 alkylenedioxy group, the substituents being selected from the group consisting of C 1

-C

4 alkyl and halogen; wherein, when q is greater than 1, the radicals Rs are the same or different, and when n is greater than 1, the radicals R 6 are the same or different; and the radicals R 5 and

R

6 are independent of one another; n is 0,1,2,3, 4 or5; q is 0, 1,2, 3 or 4; and

R

1 0 is H, Cl-C 6 alkyl, C 2

-C

8 alkenyl, C 2

-C

8 alkynyl, C 3

-C

6 cycloalkyl, or C 1

-C

6 -alkyl,

C

2 -Cs 8 alkenyl, C 2

-C

8 alkynyl or C 3

-C

6 cycloalkyl each mono- or poly-substituted by substituents from the group consisting of halogen; or is -Si(C 1

-C

4 alkyl) 3 , the alkyl groups being the same or different; C 1

-C

6 alkoxycarbonyl or an aryl or heterocyclyl group that is unsubstituted or mono- or poly-substituted by substituents from the group consisting of halogen, C 1

-C

4 alkyl and halo-Cl-C 4 alkyl; with the proviso that the group -G-phenyl is not 3-trifluoromethylbenzyloxy, 4-fluoro benzyloxy or 4-fluorophenoxy each in the 4-position, when simultaneously R 2 is ethyl, R 1 , R 8 and R 9 are methyl, R 3 and R 4 are hydrogen, q is 0, Z is oxygen and AR 7 is methyl; and, where applicable, its possible E/Z isomers, mixtures of E/Z isomers and/or tautomers, in each case in free form or in salt form, to a process for the preparation thereof and to the use of those compounds, E/Z isomers and tautomers; to pesticides, the active ingredient of which is selected from those compounds, E/Z isomers and tautomers; to a process for the preparation of those compositions and to the use thereof; to intermediates and, where applicable, their possible E/Z isomers, mixtures of E/Z isomers and/or tautomers, in free form or in salt form, for the preparation of those compounds, where applicable to tautomers, in free form or in salt form, of those intermediates; and to a process for the preparation of those intermediates and their tautomers and to the use thereof.

WO 98/54126 PCT/EP98/03074 -3 In the literature a number of methoxyacrylic acid derivatives are proposed as active ingredients in pesticides. The biological properties of those known compounds are not, however, fully satisfactory in the field of pest control and there is therefore a need to provide further compounds having pesticidal properties, especially for controlling insects and representatives of the order Acarina and especially for controlling phytopathogenic microorganisms. That problem is solved according to the invention by the provision of the present compounds of formula (I). A number of compounds of formula (I), and of the formulae (Ill), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, contain asymmetrical carbon atoms, as a result of which the compounds may occur in optically active form. By virtue of the presence of the C=X and oximino double bonds, the compounds may occur in the E and Z isomeric forms. Atropisomers of the compounds may also occur. The formulae (I), (111), (IV), (VI), (VIII) and (X) to (XIII) are to include all those possible isomeric forms and also mixtures thereof, for example racemates or mixtures of E/Z isomers, and also, optionally, salts thereof, even if these are not specifically mentioned every time. In the compounds (I), (111), (IV), (VI), (XII) and (XIII), the E-isomer as indicated with E in the respective formulae is preferred. Unless indicated to the contrary, the general terms used hereinbefore and hereinafter have the following meanings: Carbon-containing groups and compounds each contain from 1 up to and including 8, especially from 1 up to and including 6, more especially from 1 up to and including 4, very especially 1 or 2, carbon atoms. Alkyl, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkyl, alkoxy, alkylthio, alkylsulfynyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, alkoxyiminomethyl, alkylaminocarbonyl and alkylaminothiocarbonyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, that is to say methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.

WO 98/54126 PCT/EP98/03074 -4 Alkenyl, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkenyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example, vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, for example isopropenyl. Alkynyl, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkynyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example 2-ethynylpropyl or 2-propargylisopropyl.

C

3

-C

6 Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Alkylene, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkylene, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example -CH 2

CH

2 -, -CH 2

CH

2

CH

2 - or -CH 2

CH

2

CH

2

CH

2 -, or branched, for example -CH(CH 3 )-,

-CH(C

2 Hs)-, -C(CH 3

)

2 -, - CH(CH 3

)CH

2 - or -CH(CH 3

)CH(CH

3 )-. Aryl is phenyl or naphthyl, especially phenyl. Heterocyclyl is a 5- to 7-membered aromatic or nonaromatic ring having from one to three hetero atoms selected from the group consisting of N, O and S. Preference is given to aromatic 5- and 6-membered rings having one nitrogen atom as hetero atom and optionally a further hetero atom, preferably nitrogen or sulfur, especially nitrogen. Preferred heteroaryl radicals are pyrazinyl, 3'-pyridyl, 2'-pyridyl, 4'-pyridyl, 2'-pyrimidinyl, 4'-pyrimidinyl, 5' pyrimidinyl, 2'-thiazolyl, 2'-oxazolyl, 2'-furanyl, 3'-furanyl, 3'-tetrahydrofuranyl, 2'-thienyl, 3' thienyl and 2'-thiazolyl. Halogen, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkyl, haloalkenyl and haloalkynyl, is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine, very especially fluorine.

WO 98/54126 PCT/EP98/03074 -5 Halo-substituted carbon-containing groups and compounds, such as haloalkyl, haloalkenyl or haloalkynyl, may be partially halogenated or per-halogenated, it being possible in the case of poly-halogenation for the halogen substituents to be the same or different. Examples of haloalkyl, as a group per se and also as a structural unit of other groups and compounds, such as of haloalkenyl, are methyl that is mono- to tri-substituted by fluorine, chlorine and/or by bromine, such as CHF 2 or CF 3 ; ethyl that is mono- to penta-substituted by fluorine, chlorine and/or by bromine, such as CH 2

CF

3 , CF 2

CF

3 , CF 2

CC

3 , CF 2

CHC

2 ,

CF

2

CHF

2 , CF 2

CFCI

2 , CF 2 CHBr 2 , CF 2 CHCIF, CF 2 CHBrF or CCIFCHCIF; propyl or isopropyl each mono- to hepta-substituted by fluorine, chlorine and/or by bromine, such as

CH

2 CHBrCH 2 Br, CF 2

CHFCF

3 , CH 2

CF

2 CF3 or CH(CF 3 ) 2; and butyl, or an isomer thereof, each mono- to nona-substituted by fluorine, chlorine and/or by bromine, such as

CF(CF

3

)CHFCF

3 or CH 2

(CF

2

)

2

CF

3 . Haloalkenyl is, for example, CH 2 CH=CHCI, CH 2

CH=CC

2 ,

CH

2

CF=CF

2 or CH 2

CH=CHCH

2 Br. Haloalkynyl is, for example, CH 2 C=CF, CH 2

C-CCH

2 CI or

CF

2

CF

2

C-CCH

2 F. A number of compounds of formula (I), and of the formulae (11I), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, may, as is known to the person skilled in the art, be present in the form of tautomers, for example when A-R 7 is H. Hereinbefore and hereinafter any reference to compounds of formulae (I), (111), (IV), (VI), (VIII) and (X) to (XIII) should be understood as including also corresponding tautomers, even when the latter are not specifically mentioned in each case. Compounds of formula (I), and of the formulae (Ill), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, that have at least one basic centre may, for example, form acid addition salts. Such salts are formed, for example, with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo substituted, C 1

-C

4 alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturated dicarboxylic acids, e.g. oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, hydroxycarboxylic acids, e.g. ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halo-substituted, C 1

-C

4 alkane- or aryl-sulfonic acids, e.g. methane- WO 98/54126 PCT/EP98/03074 -6 or p-toluene-sulfonic acid. Furthermore, compounds of formula (I) having at least one acid group may form salts with bases. Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri ethanolamine. It is also possible for corresponding internal salts to be formed. Within the context of the invention, preference is given to agrochemically advantageous salts; also included, however, are salts which mith not be advantageous for agrochemical uses, which are used however, for example, for isolating and/or purifying free compounds of formula (I) or agrochemically acceptable salts thereof. Hereinbefore and hereinafter any reference to the free compounds of formula (I) is to be understood as including also the corresponding salts of formula (I), and any reference to the salts of the compounds of formula (I) is to be understood as including also the corresponding free compounds of the formula (I). The same applies also to tautomers of compounds of formulae (I), (Ill), (IV), (VI), (VIII) and (X) to (XIII) and salts thereof. In each case the free form is generally preferred. Preferred embodiments within the context of the invention, in each case taking into consideration the provisos mentioned hereinbefore, are: (1) a compound of formula (I) wherein X is CH and Z is O; (2) a compound of formula (I) wherein X is N and Z is O; (3) a compound of formula (I) wherein Y is C 1

-C

2 alkoxy, especially methoxy; (4) a compound of formula (I) wherein R 1 is Cl-C 2 alkyl, especially methyl; (5) a compound of formula (I) wherein

R

2 is ethyl, propyl, butyl, isopropyl, isobutyl, sec.butyl or tert-butyl, especially ethyl or propyl, more especially ethyl; (6) a compound of formula (I) wherein WO 98/54126 PCT/EP98/03074 -7

R

3 is H, C 1 -C4alkyl, C 1

-C

4 alkoxy, OH, CN, NO 2 , halogen, halo-C 1

-C

4 alkyl or halo-C 1

-C

4 alkoxy, preferably H, C 1

-C

4 alkyl, C0 1

-C

4 alkoxy or halogen, especially H, methyl, methoxy, chlorine or fluorine, more especially H; (7) a compound of formula (I) wherein

R

4 is H, C0 1

-C

4 alkyl, C 1

-C

4 alkoxy, OH, CN, NO 2 , halogen, halo-Cs-C 4 alkyl or halo-C 1

-C

4 alkoxy, preferably H, C 1

-C

4 alkyl, C 1

-C

4 alkoxy or halogen; especially H, methyl, methoxy, chlorine or fluorine; more especially H; (8) a compound of formula (I) wherein

R

8 is H or C 1

-C

2 alkyl, preferably C-C 2 alkyl, especially methyl; (9) a compound of formula (I) wherein R 9 is methyl or fluoromethyl; preferably methyl; (10) a compound of formula (I) wherein

R

6 is halogen, C-C 4 alkyl, halo-C-C 4 alkyl, halo-C 1

-C

4 alkoxy, C 3

-C

6 cycloalkyl, halo-C 3 C6cycloalkyl or CH 2 Si(CH 3

)

3 ; preferably halogen, C 1

-C

4 alkyl, halo-C 1

-C

4 alkoxy and halo-C-C 4 alkyl, especially halogen, C 1

-C

4 alkyl, halomethyl or halomethoxy, more especially chlorine, trifluoromethyl, trifluoromethoxy or tert-butyl; (11) a compound of formula (I) wherein n is 1 or 2, preferably 1; (12) a compound of formula (I) wherein G is O or -O-CH 2 -, especially O; (13) a compound of formula (I) wherein Rs is halogen, C 1

-C

4 alkyl, halo-Cl-C 4 alkyl, halo

C-C

4 alkoxy, C 3

-C

6 cycloalkyl, halo-C 3

-C

6 cycloalkyl or CH 2 Si(CH 3

)

3 , and q is 0, 1, 2 or 3, preferably 0, 1 or 2, especially 0 or 1, more especially 0; (14) a compound of formula (I) wherein A is a direct bond, Cl-Co 10 alkylene, or halo-C 1 -Cloalkylene; preferably a direct bond or Cl-C 4 alkylene; especially a direct bond or methylene; WO 98/54126 PCT/EP98/03074 -8 (15) a compound of formula (I) wherein A is a direct bond and

R

7 is C 1

-C

4 -alkyl, CH 2

-CH=CH

2 or CH 2 -C-CH, especially methyl or ethyl, more especially ethyl; (16) a compound of formula (I) wherein X is N; Y is OCH 3 ; Z is O; R 2 is ethyl; R 3 and R 4 are H; AR 7 is ethyl; G is O; q is 0; n is 1 and

R

6 is CF 3 . Special preference is given within the context of the invention to compounds of formula (I) given in Tables 1 to 4, and, where applicable, their E/Z isomers and mixtures of E/Z isomers. The invention relates also to a process for the preparation of the compounds of formula (I) and, where applicable, their E/Z isomers, mixtures of E/Z isomers and/or tautomers, wherein n, q, A, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are as defined above for formula (I) and wherein the provisos mentioned above for the compounds of formula (I) apply, in each case in free form or in salt form, which process comprises al) reacting a compound of formula Z

R

9 0 ' X Y XX - 0 (11),

R

3 1 R4 which is known or can be prepared in accordance with methods known per se and wherein X, Y, Z, R, R 4 and R 9 are as defined for formula (I) and X, is a leaving group, preferably in the presence of a base, with a compound of formula WO 98/54126 PCT/EP98/03074 -9

N.O-AR

7 N A H , 0 ' .N IEG

R

2 G (Ill), / - (R6)n

(R

5 )q wherein n, q, A, G, R 2 , R 5 , R 6 and R 7 are as defined for formula (I); or a2) reacting a compound of formula N ,O R 7 N "A v) | E R, G (IV), R2 (R 6

)

n

(R

5 )q / wherein n, q, A, G, R 2 , Rs, R 6 and R 7 are as defined for formula (I), optionally in the presence of a base, with a compound of formula Z R ONH 3 CI (V), R N

R

4 which is known or can be prepared in accordance with methods known per se, and wherein X, Y, Z, R 3 , R 4 and R 9 are as defined for formula (I); or a3) reacting a compound of formula z X , OH (R6

R

9 Or Y N K n /E (VI),

R

3 \ R2 R4 (Rs)q wherein n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are as defined above for formula (I) and wherein the provisos mentioned above for the compounds of formula (I) apply, with a compound of formula WO 98/54126 PCT/EP98/03074 -10

X

1

-A-R

7 (VII), wherein A and R 7 are as defined above for formula (I) and X 1 is a leaving group as for formula (11); b) to prepare a compound of formula (I) wherein Y is NHR 8 and Z is O, reacting a compound of formula (I) wherein Y is OR 1 with a compound of formula R 8

NH

2 , which is known or can be prepared in accordance with methods known per se and wherein R, is as defined for formula (I); or c) to prepare a compound of formula (I) wherein Y is NHR 8 and Z is S, reacting a compound of formula (I) wherein Y is R 8

NH

2 and Z is O with P 4

S

1 0 or Lawesson's reagent [2,4-bis (methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide], or d) to prepare a compound of formula (I) wherein Z is SO, reacting a compound of formula (I) wherein Z is S with an oxidising agent; and, in each case, if desired, converting a compound of formula (I) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, into a different compound of formula (I) or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, separating a mixture of E/Z isomers obtainable according to the process and isolating the desired isomer and/or converting a free compound of formula (I) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, into a salt, or converting a salt of a compound of formula (I) or of an E/Z isomer or tautomer thereof, obtainable according to the process or by a different method, into a free compound of formula (I), or an E/Z isomer or tautomer thereof, or into a different salt. The invention relates also to a process for the preparation of compounds of formula (11l), in each case in free form or in salt form, which process comprises e) reacting a compound of formula (IV) wherein n, q, A, G, R 2 , Rs, R 6 and R 7 are as defined for formula (I), optionally in the presence of a base, with H 2 NOH or with a salt thereof; or f) reacting a compound of formula WO 98/54126 PCT/EP98/03074 -11 OH O I Ns

R

2 G R (VIII), / - (R 6

)

°

(R

5 )q / wherein n, q, G, R 2 , Rs and R 6 are as defined for formula (I), optionally in the presence of a base, with a compound of formula

R

7

AONH

2 (IX), which is known or can be prepared in accordance with methods known per se and wherein A and R 7 are as defined for formula (I) and, in each case, if desired, converting a compound of formula (Ill) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, into a different compound of formula (III) or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, separating a mixture of E/Z isomers obtainable according to the process and isolating the desired isomer and/or converting a free compound of formula (111) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, into a salt, or converting a salt of a compound of formula (111), or of an E/Z isomer or tautomer thereof, obtainable according to the process or by a different method, into a free compound of formula (111), or an E/Z isomer or tautomer thereof, or into a different salt. The invention relates also to a process for the preparation of compounds of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula Z Ro V X 0 0 (R 6)n / O . N(X), R G

R

4 (Rs)q wherein n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 8 and R 9 are as defined above for formula (I), with hydroxylamine.

WO 98/54126 PCT/EP98/03074 -12 The invention relates also to a process for the preparation of compounds of formula (X), in each case in free form or in salt form, which process comprises h) reacting a compound of formula (VIII) with a compound of formula (11). The invention relates also to a process for the preparation of compounds of formula (VIII), in each case in free form or in salt form, which process comprises i) reacting a compound of formula O 0 G (XI),

R

2

(R

n

(R

5 )q ( wherein n, q, G, R 2 , Rs and R 6 are as defined for formula (I), and which is known or can be prepared in accordance with methods known per se, with a nitrite. The invention also relates to the following novel intermediates (XII) and (XIII) and the methods for the preparation of the compounds of the formulae (111), (II) and (XIII) known per se: 0 G k) R 2

(R

6

)

n (Xll) + Alkylnitrite (Rs)q N,0H IE G (XIll); R2 (R)n

(R(R

6 ) (Rs)q / WO 98/54126 PCT/EP98/03074 -13 N OAR 1) (XIII) + (VII) R G (IV); and I) (III)R 2 __ (R 6

)

0

(R

5 )q m) (IV) + Hydroxylamin > (111); wherein in the compounds of the formulae (XII) and (XIII) R 2 , Rs, R 6 , R 7 , A, G, q und n are as defined for formula (I). The observations made above in respect of E/Z isomers and tautomers of compounds of formulae (I) and (111) apply analogously also in respect of the E/Z isomers and tautomers of starting materials mentioned hereinbefore and hereinafter. The reactions described hereinbefore and hereinafter are carried out in a manner known per se, for example in the absence or usually in the presence of a suitable solvent or diluent or of a mixture thereof, the reactions being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range of from approximately 000C to the boiling temperature of the reaction medium, preferably from approximately 20C00 to approximately +12000, especially from 600C to 800C. Especially advantageous reaction conditions may be found in the Examples. The reactants may be reacted with one another as they are, that is to say without the addition of a solvent or diluent, for example in molten form. Generally, however, the addition of an inert solvent or diluent or a mixture thereof is advantageous. The reactions are, if required, carried out in a closed vessel, under pressure, and under a protective gas atmosphere, for example nitrogen or argon, especially nitrogen; and/or under anhydrous conditions; preferably in an inert gas atmosphere and under normal pressure. The products are usually isolated in accordance with customary methods, for example by filtration, crystallisation, distillation or chromatography, or any suitable combination of those methods.

WO 98/54126 PCT/EP98/03074 -14 The starting materials given hereinbefore and hereinafter that are used to prepare the compounds of formula (I) and, where applicable, their E/Z isomers and tautomers are known or can be prepared in accordance with methods known per se, for example according to the details given hereinafter. Variants al/a2/a3 and h): Suitable leaving groups X, in the compounds (II) and (VII) are, for example, hydroxy, Cl-C 8 alkoxy, halo-C 1

-C

8 alkoxy, C 1

-C

8 alkanoyloxy, mercapto, C0 1

-C

8 alkylthio, halo-C-C 8 alkyl thio, C 1

-C

8 alkanesulfonyloxy, halo-C 1

-C

8 alkanesulfonyloxy, benzenesulfonyloxy, toluene sulfonyloxy and halogen, preferably toluenesulfonyloxy, trifluoromethanesulfonyloxy and halogen, especially halogen. Suitable bases for facilitating the reaction are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines, alkylenediamines, unsubstituted or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. There may be mentioned by way of example sodium hydroxide, hydride, amide, methanolate, acetate and carbonate, potassium tert-butanolate, hydroxide, carbonate and hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclo hexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,5-diaza bicyclo[5.4.0]undec-5-ene (DBU). Examples of usefule solvent for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloro-ethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran and dioxane; ketones, such as acetone, methyl ethyl ketone and methyl isobutyl ketone; alcohols, such as methanol, WO 98/54126 PCT/EP98/03074 -15 ethanol, propanol, isopropanol, butanol, ethylene glycol and glycerol; amides, such as N,N-dimethylformamide, N,N-diethyl-formamide, N,N-dimethylacetamide, N-methylpyrrolidone and hexamethylphosphoric acid triamide; nitriles, such as acetonitrile and propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of a base, bases used in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, may also serve as solvents or diluents. The reaction is carried out advantageously in a temperature range from approximately 0oC to approximately 1800C, especially from approximately 10OC to approximately 800C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. In a preferred embodiment of variant al, a compound (11) is reacted with a compound (Ill) at from 0°C to 800C, preferably from 1000C to 300C, in an inert solvent, preferably an amide, especially N,N-dimethylformamide, in the presence of a metal hydride, preferably sodium hydride. Especially preferred conditions for the reaction are described in Examples P1 e) and P1 f). Variant b) Examples of useful solvents for carrying out the reaction or diluents include those mentioned in variants al/a2/a3 and h). The reaction is carried out advantageously in a temperature range from approximately 000C to approximately 1800C, especially from approximately 1000C to approximately 800C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. Especially preferred conditions for the reaction are described in Example P1 g). Variant c) WO 98/54126 PCTIEP98/03074 -16 Examples of useful solvents or diluents for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachlorome thane, dichloroethane, trichloroethene and tetrachloro-ethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert -butyl methyl ether, ethylene glycol mono methyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran and dioxane; and sulfoxides, such as dimethyl sulfoxide. The reaction is carried out advantageously in a temperature range from approximately 00C to approximately +120C0, especially from approximately 80C to approximately +1200C. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. Variant d) Suitable oxidising agents are, for example, inorganic peroxides, such as sodium perborate, or hydrogen peroxide, or organic per-acids, such as perbenzoic acid or peracetic acid, or mixtures of organic acids and hydrogen peroxide, for example acetic acid/hydrogen peroxide. Examples of useful solvents or diluents for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachlorome thane, dichloroethane, trichloroethene and tetrachloro-ethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert -butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetra hydrofuran and dioxane; ketones, such as acetone, methyl ethyl ketone and methyl isobutyl ketone; alcohols, such as methanol, ethanol and propanol; amides, such as N,N-dimethylformamide, N,N-diethylformamide, N,N dimethylacetamide, N-methylpyrrolidone and hexamethylphosphoric acid triamide; nitriles, such as acetonitrile and propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of an organic acid or a per-acid, acids used in WO 98/54126 PCT/EP98/03074 -17 excess, for example strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C,-C 4 alkane-carboxylic acids, e.g. formic acid, acetic acid or propionic acid, may also serve as solvent or diluent. The reaction is carried out advantageously in a temperature range from approximately 00C to approximately +1200C, especially from approximately OoC to approximately +400C. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. Variants e)/g) Suitable bases for facilitating the reaction are, for example, those mentioned in variants al/a2/a3/h. Examples of useful solvents or diluents for carrying out the reaction include those mentioned in variants al/a2/a3/h). The reaction is carried out advantageously in a temperature range from approximately OC to approximately 1800C, especially from approximately 10OC to approximately 800C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. Variant f) Suitable bases for facilitating the reaction are, for example, those mentioned in variants al/a2/a3/h. Examples of useful solvents or diluents for carrying out the reaction include those mentioned in variant al/a2. The reaction is carried out advantageously in a temperature range from approximately 000C to approximately 1800C, especially from approximately 10OC to approximately 800C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. In a preferred embodiment of variant f), a compound of formula (VIII) is reacted with a compound of formula (IX) at from 000C to 1200C, preferably from 600C to 12000, in an inert WO 98/54126 PCT/EP98/03074 -18 solvent, preferably an amine, especially pyridine. Especially preferred conditions for the reaction are described in Example P 1d). Variant i) Suitable reactants are especially alkyl nitrites, preferably isopentyl nitrite. Suitable acids for facilitating the reaction are, for example, hydrohalic acids and nitric acid, especially gaseous hydrogen chloride. Suitable solvents are especially those mentioned under variant d), especially ethers, such as diethyl ether, di-n-butyl ether and methyl isobutyl ether; or alcohols, for example ethanol and methanol. The reaction is carried out advantageously in a temperature range from approximately OC to approximately 1800C, preferably from approximately OC to 800C, especially at room temperature. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours. Especially preferred conditions for the reaction are described in Example Plc). The compounds of formulae (I) to (XIII) may be in the form of one of the possible isomers or in the form of a mixture thereof, for example according to the number of asymmetric carbon atoms and the absolute and relative configuration thereof in the form of pure isomers, such as antipodes and/or diastereoisomers, or in the form of mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates; the invention relates both to the pure isomers and to all possible mixtures of isomers and this is to be understood accordingly hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case. Mixtures of diastereoisomers and mixtures of racemates of compounds of formulae (I), (111), (IV), (VI), (VIII), and (X) to (XIII) that are obtainable in accordance with the process depending upon the starting materials and procedures chosen, or by other means, can be separated into the pure diastereoisomers or racemates in known manner on the basis of the WO 98/54126 PCT/EP98/03074 -19 physico-chemical differences between the constituents, for example by fractional crystallisation, distillation and/or chromatography. Mixtures of enantiomers, such as racemates, so obtainable can be separated into the optical antipodes by known methods, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, for example high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific immobilised enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, in which case only one enantiomer is complexed. Apart from by the separation of corresponding mixtures of isomers, it is possible according to the invention to obtain pure diastereoisomers or enantiomers also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials having appropriate stereo chemistry. It is advantageous to isolate or synthesise the biologically more active isomer, for example enantiomer, or mixture of isomers, for example mixture of enantiomers, insofar as the individual components have different biological activity. The compounds of formulae (I), (111), (IV), (VI), (VIII) and (X) to (XIII) can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents that may have been used for the crystallisation of compounds in solid form. The invention relates to all those embodiments of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or a starting material is used in the form of a derivative or a salt and/or its racemates or antipodes, or, especially, is formed under the reaction conditions. In the process of the present invention there are preferably used those starting materials and intermediates which result in the compounds of formula (I) described at the beginning as being especially valuable.

WO 98/54126 PCT/EP98/03074 -20 The invention relates especially to the preparation processes described in Examples P1 a) to g). The invention relates also to starting materials and intermediates used according to the invention in the preparation of compounds of formula (I), especially the compounds of formulae (111), (IV), (VI), (VIII) and (X) to (XIII), which are novel, to their use and to processes for the preparation thereof. The preferred meanings of R 2 , Rs, R 6 , R 7 , A, G, q und n in these compounds of the of formulae (111), (IV), (VI), (VIII) and (X) to (XIII) are the same as given for the compounds of the formula (I). In particular, the compounds of formulae (111) and (VIII) can be prepared analogously to Examples P1 d) and Plc), respectively. In the area of pest control, the compounds of formula (I) according to the invention are valuable preventive and/or curative active ingredients having a very advantageous biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants. The compounds of the invention are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina, and phytopathogenic fungi. The insecticidal, ovicidal and/or acaricidal action of the compounds of the invention may manifest itself directly, i.e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or of their eggs, or indirectly, for example in reduced oviposition and/or hatching rate, good activity correspond ing to a mortality of at least 50 to 60 %. The mentioned animal pests include, for example, those mentioned in European Patent Application EP-A-736 252. The said pests mentioned in EP-A-736 252 are included by reference in the subject matter of the present invention. The mentioned phytopathogenic fungi include, for example: of the class of Fungi imperfecti, for example, Botrytis spp., Pyricularia spp., Helmintho sporium spp., Fusarium spp., Septoria spp., Cercospora spp. and Alternaria spp.; of the class of Basidiomycetes, for example, Rhizoctonia spp., Hemileia spp. and Puccinia spp.; WO 98/54126 PCT/EP98/03074 -21 of the class of Ascomycetes, for example, Venturia spp., Erysiphe spp., Podosphaera spp., Monilinia spp. and Uncinula spp.; and of the class of Oomycetes, for example, Phytophthora spp., Pythium spp. and Plasmopara spp.. With the compounds according to the invention it is possible to control, i.e. to inhibit or destroy, pests of the mentioned type occurring especially on plants, more especially on useful plants and ornamentals in agriculture, in horticulture and in forestry, or on parts of such plants, such as the fruit, blossom, leaves, stems, tubers or roots, while some of the parts of the plants that grow later are also protected against those pests. Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries and blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumber and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals. The compounds according to the invention are especially suitable for controlling insects and representatives of the order Acarina, especially plant-destructive feeding insects, such as Anthonomus grandis, Diabrotica balteata, Heliothis virescens larvae, Plutella xylostella and Spodoptera littoralis larvae, and spider mites, such as Tetranychus spp., in cotton, fruit, maize, soybean, rape and vegetable crops. Further areas of use of the compounds according to the invention are the protection of stored goods and stocks and materials, and also in the hygiene sector, especially the protection of domestic animals and productive livestock against pests of the mentioned type.

WO 98/54126 PCT/EP98/03074 -22 The invention therefore relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances. The active ingredient is used in those compositions in pure form: a solid active ingredient, for example, in a specific particle size, or preferably together with - at least - one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants). There serve as formulation adjuvants, for example, solid carriers, solvents, stabilisors, "slow release" adjuvants, colorants and optionally surface-active substances (surfactants). There come into consideration as carriers and adjuvants all substances customarily used in plant protection compositions, especially in compositions for controlling slugs and snails. Suitable adjuvants, such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants and other adjuvants in the compositions used according to the invention are, for example, the same substances as described in EP-A-736 252. The said adjuvants mentioned in EP-A-736 252 are included by reference in the subject matter of the present invention. Those compositions for controlling pests can be formulated, for example, in the form of wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates or aerosols. The compositions are of the same type as those described, for example, in EP-A-736 252. The compositions usually comprise 0.1 to 99%, preferably 0.1 to 95%, of active ingredient, and 1 to 99.9%, preferably 5 to 99.9%, of - at least - one solid or liquid adjuvant, it generally being possible for 0 to 25%, preferably 0.1 to 20%, of the composition to be surfactants (in each case percentages are by weight). Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations which WO 98/54126 PCT/EP98/03074 - 23 have substantially lower active ingredient concentrations. Preferred formulations have especially the composition described in EP-A-736 252, Examples F1 to F8. The activity of the compositions according to the invention can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticidal, acaricidal and/or fungicidal active ingredients. Examples of suitable additional active ingredients include representatives of the following classes of compounds: organophosphorus compounds, nitrophenol derivatives, formamidines, ureas, benzoylureas, carbamates, pyrethroids, chlorinated hydrocarbons, neonicotinoids, macrolides and Bacillus thuringiensis preparations. The compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example bactericides, nematicides, molluscicides or selective herbicides. The compositions according to the invention are prepared in known manner, in the absence of adjuvants, for example by grinding and/or sieving a solid active ingredient or mixture of active ingredients, for example to a specific particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant(s). The invention relates also to those methods for the preparation of the compositions according to the invention and to the use of the compounds of formula (I) in the preparation of those compositions. The invention relates also to the methods of application of the compositions, i.e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering or pouring, which are selected in accordance with the intended objectives and prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type. Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient. The rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.

WO 98/54126 PCT/EP98/03074 -24 A preferred method of application in the area of plant protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depending on the risk of infestation by the pest in question. However, the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredient is incorporated in solid form into the locus of the plants, for example into the soil, e.g. in granular form (soil application). In paddy rice crops, such granules may be applied in metered amounts to the flooded rice field. The compositions according to the invention are also suitable for protecting plant propagation material, e.g. seed, such as fruit, tubers or grains, or plant cuttings, from fungal infections and animal pests. The propagation material can be treated with the formulation before planting: seed, for example, can be dressed before being sown. The compounds of the invention can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation. The formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing. The invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated. The following Examples serve to illustrate the invention. They do not limit the invention. Temperatures are given in degrees Celsius. Preparation Examples Example Pl: (2-{2-[4-(3-Trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-l1-ethyl-ethylidene aminooxymethyl}-phenyl)-3-methoxy-acrylic acid methyl ester (compound 1.1) a) 1-(4-Fluorophenyl)-butan-1-one 106.5 g of butyric acid chloride are added dropwise at 70C00 in the course of one hour to a mixture of 180 g of 4-fluorobenzene and 147 g of aluminium chloride. The mixture is stirred at 800C for 45 minutes, cooled to room temperature and poured into a mixture of 1 litre of ice and 150 ml of conc. HCI. Extraction is carried out twice with 300 ml of diethyl ether, the combined organic extracts are washed with water and sodium chloride solution and dried over sodium sulfate, and the solvent is removed by evaporation in vacuo. The resulting WO 98/54126 PCT/EP98/03074 -25 crude product is purified by distillation to yield the title product having a boiling point of 103 1050C (15 mbar). b) 1-[4-(3-Trifluoromethylphenoxy)-phenyl]-butan-1-one 158.8 g of 1-(4-fluorophenyl)-butan-1 -one are added slowly at room temperature to a mixture of 154.2 g of 3-hydroxytrifluoromethylbenzene, 197 g of potassium carbonate and 1200 ml of N,N-dimethylacetamide, and the mixture is heated and stirred at 180 0 C for 10 hours. The mixture is then cooled to room temperature and filtered and the filtrate is concentrated by evaporation in vacuo. The residue is dissolved in diethyl ether and the organic phase is washed once with water, once with 10% potassium hydroxide solution and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation. The solid product is removed by filtration and dried in vacuo to yield the title compound having a melting point of 35-36°C. c) 1-[4-(3-Trifluoromethylphenoxy)-phenyl]-butane-1,2-dione-2-oxime HCI gas is introduced for one minute into 1 litre of diethyl ether and then 277 g of 1-[4-(3 trifluoromethylphenoxy)-phenyl]-butan-1 -one are added. 126.2 g of isopentyl nitrite are added dropwise to that mixture, the reaction mixture is then stirred at room temperature for 5 hours, HCI gas is again introduced for one minute and the reaction mixture is left to stand at room temperature for 14 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation in vacuo. The residue is made into a slurry with hexane and filtered, and the filter residue is dried in vacuo to yield the title compound having a melting point of 74-760C. d) 1-[4-(3-Trifluoromethylphenoxy)-phenyl]-butane-1,2-dione-1-[ethyloxime]-2-oxime A mixture of 70 g of 1-[4-(3-trifluoromethylphenoxy)-phenyl]-butane-1,2-dione-2-oxime and 21.3 g of O-ethylhydroxylamine hydrochloride in 250 ml of pyridine is boiled at reflux for one hour. Once it has cooled, the reaction mixture is dissolved in 500 ml of ethyl acetate and the organic phase is washed once with water, once with 10% HCI solution and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated by evaporation. The crude product is recrystallised from n-hexane. The title compound having a melting point of 122-124oC is obtained.

WO 98/54126 PCT/EP98/03074 -26 e) (2-{2-[4-(3-Trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-1l-ethyl-ethylidene aminooxymethyl}-phenyl)-3-methoxy-acrylic acid methyl ester (compound 1.1) 7.0 g of 1-[4-(3-trifluoromethylphenoxy)-phenyl]-butane-1,2-dione-1l-[ethyloxime]-2-oxime dissolved in 30 ml of N,N-dimethylformamide are added dropwise to a suspension of 0.83 g of sodium hydride (55% in oil) in 50 ml of N,N-dimethylformamide, and the reaction mixture is then stirred at room temperature for 15 minutes. 5.25 g of 2-(bromomethyl)-a-(methoxy methylene)-phenylacetic acid methyl ester in 20 ml of N,N-dimethylformamide are then added dropwise and the reaction mixture is stirred further at room temperature for 1 hour. The mixture is then acidified with acetic acid and concentrated by evaporation in vacuo. The residue is dissolved in ethyl acetate and the solution is washed three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in vacuo. Purification by flash chromatography (silica gel, ethyl acetate/hexane 1:3) yields the title compound having a melting point of 71-73 0 C. f) (2-{2-[4-(3-Trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-1l-ethyl-ethylidene aminooxymethyl}-phenyl)-3-methylimino-acrylic acid methyl ester (compound 2.1) 10.0 g of 1-[4-(3-trifluoromethylphenoxy)-phenyl]-butane-1,2-dione-1 -[ethyloxime]-2-oxime dissolved in 25 ml of N,N-dimethylformamide are added dropwise to a suspension of 1.2 g of sodium hydride (55% in oil) in 50 ml of N,N-dimethylformamide, and the reaction mixture is then stirred at room temperature for 15 minutes. 7.5 g of 2-(bromomethyl)-a-(methoxy imino)-phenylacetic acid methyl ester in 20 ml of N,N-dimethylformamide are then added dropwise and the reaction mixture is stirred further at room temperature for 1 hour. The mixture is then acidified with acetic acid and concentrated by evaporation in vacuo. The residue is dissolved in ethyl acetate and the solution is washed three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in vacuo. Purification by flash chromatography (silica gel, ethyl acetate/hexane 1:3) yields the title compound having a melting point of 73-75°C. g) (2-{2-[4-(3-Trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-l1-ethyl-ethylidene aminooxymethyl}-phenyl)-3-methylimino-acrylic acid methyl amide (compound 3.1) A mixture of 4 g of (2-(2-[4-(3-trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-1l-ethyl ethylidene-aminooxymethyl}-phenyl)-3-methylimino-acrylic acid methyl ester and 5.2 ml of an 8M solution of methylamine in ethanol is left to stand at room temperature for 16 hours.

WO 98/54126 PCT/EP98/03074 - 27 The solvent is then evaporated to dryness in vacuo. The residue is stirred with hexane and filtered and the filter residue is dried in vacuo to yield the title compound having a melting point of 113-1150C. Example P2: The other compounds listed in Tables 1 to 4 can also be prepared in a manner analogous to that described in Example P1. In the column "Phys. data" of the Tables, in each case the temperatures given denote the melting point in 0C of the compound in question. Table 1.1: Compounds of general formula

CH

3 0 COOCH 3 N A-R (.1) N I I I(R 6 )n R2 ~OO Compd. (R 6 )n R2 A-R 7 Phys. data 1-1 3-CF 3

C

2

H

5

C

2

H

5 71-73 (isomer A) 1-2 3-CF 3

C

2 Hs CH 3 134-136 (isomer A) 1-3 4-CI C 2

H

5

C

2 Hs 94-96 (isomer A) 1-4 4-CI C 2 Hs CH 3 126-128 (isomer A) 1-5 4-tert-butyl C 2 Hs C 2 Hs 94-96 (isomer A) 1-6 4-tert-butyl C 2

H

5

CH

3 114-116 (isomer A) 1-7 3,4-CI2 C 2 Hs CH 3 137-139 (isomer A) 1-8 3,4-CI2 C 2

H

5

C

2 Hs 95-97 (isomer A) 1-9 3-CF 3 n-propyl C 2

H

5 84-86 (isomer A) 1-10 3-CF 3 n-propyl CH 3 102-103 (isomer A) 1-11 4-OCF 3

C

2

H

5

C

2

H

5 90-92 (isomer A) 1-12 4-OCF 3

C

2 Hs CH 3 94-96 (isomer A) 1-13 4-CI n-propyl C 2

H

5 76-78 (isomer A) 1-14 4-CI n-propyl CH 3 91-92 (isomer A) 1-15 4-tert-butyl n-propyl C 2 Hs 81-83 (isomer A) 1-16 4-tert-butyl n-propyl CH 3 resin (isomer A) 1-17 4-CF 3

C

2 Hs n-propyl 84-86 (isomer A) 1-18 4-CF 3

C

2 Hs CH 3 109-111 (isomer A) WO 98/54126 PCT/EP98/03074 -28 Compd. (R 6 )n R2 A-R 7 Phys. data 1-19 4-CF 3

C

2 Hs C 2 Hs 119-121 (isomer A) 1-20 2-CI, 4-CF 3 cyclopropyl C 2

H

5 resin (isomer A) 1-21 2-CI, 4-CF 3 cyclopropyl CH 3 resin (isomer A) 1-22 4-CF 3

C

2

H

5

CH

2 -C=-CH 80-82 (isomer A) 1-23 4-CF 3

C

2 Hs CH 2

-C=CH

2 86-88 (isomer A) 1-24 4-CF 3

C

2

H

5 i-propyl 78-80 (isomer A) 1-25 4-CF 3

C

2 Hs n-butyl Harz (isomer A) 1-26 3-CF 3

C

2 Hs n-propyl 1-27 3-CF 3

C

2 Hs n-butyl 1-28 3-CF 3

C

2

H

5 i-propyl 1-29 3-CF 3

C

2

H

5

CH

2 -C=-CH 1-30 3-CF 3

C

2 Hs CH 2

-C=CH

2 1-31 4-OCF 3

C

2

H

5 n-propyl 1-32 4-OCF 3

C

2 Hs n-butyl 1-33 4-OCF 3

C

2 Hs i-propyl 1-34 4-OCF 3

C

2 Hs CH 2 -C=-CH 1-35 4-OCF 3

C

2 Hs CH 2

-C=CH

2 1-36 3-Cl, 4-CF 3

C

2

H

5

CH

3 1-37 3-CI, 4-CF 3

C

2

H

5

C

2

H

5 1-38 4-CI, 3-CF 3

C

2 Hs CH 3 1-39 4-CI, 3-CF 3

C

2

H

5

C

2

H

5 Table 1.2: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 1.3: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.4: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 2-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.5: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.6: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 3-Cl and the substituent A-R 7 corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 29 Table 1.7: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.8: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.9: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.10: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 2-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.11: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.12: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ), is 3-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.13: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 2-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.14: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.15: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.16: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.17: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-O-C 2

H

5 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.18: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 4-O-n-butyl and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 1.19: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ), is 4-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.20: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 4-C 2 Hs and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.21: Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 )n is 4-C 3

H

7 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.22: Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.23: Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 30 Table 1.24: Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.25: Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.26: Compounds of general formula (I.1) wherein R 2 is n-propyl, (R 6 )n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.27: Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.28: Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 )n is 3-CF 3 and the substituent A-R7 corresponds in each case to a line of Table A. Table 1.29: Compounds of general formula (I.1) wherein R 2 is cyclopropyl, (R 6 )n is 4-CI and the substituent A-R7 corresponds in each case to a line of Table A. Table 1.30: Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 )n is 4-tert-butyl and the substituent A-R7 corresponds in each case to a line of Table A. Table 1.31: Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 )n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 1.32: Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 )n is 3-CI, 4-CF 3 and the substituent A-R7 corresponds in each case to a line of Table A. Table 1.33: Compounds of general formula (I.1) wherein R 2 is ethyl, (R 6 )n is 4-CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.1: Compounds of general formula

CH

3 0 / N COOR 1 N 0

A-P

7 (1.2) . .I(R 6 n R2 'No. a Compd. (R 6 )n R 1

R

2

A-R

7 Phys. data 2-1 3-CF 3

CH

3

C

2

H

5

C

2 Hs 73-75 (isomer A) 2-2 3-CF 3

CH

3

C

2

H

5

CH

3 114-116 (isomer A) 2-3 4-Cl CH 3

C

2

H

5

C

2 Hs 73-75 (isomer A) 2-4 4-Cl CH 3

C

2 Hs CH 3 96-98 (isomer A) 2-5 4-tert-butyl CH 3

C

2

H

5

C

2

H

5 95-97 (isomer A) 2-6 4-tert-butyl CH 3

C

2 Hs CH 3 106-107 (isomer A) WO 98/54126 PCT/EP98/03074 -31 Compd. (R)n R 1

R

2

A-R

7 Phys. data 2-7 4-CF 3

CH

3

C

2

H

5

C

2

H

5 96-98 (isomer A) 2-8 3,4-CI 2

CH

3

C

2

H

5

C

2

H

5 74-76 (isomer A) 2-9 3,4-CI012 CH 3

C

2

H

5

CH

3 114-116 (isomer A) 2-10 3-CF 3

CH

3 n-propyl C 2 Hs 94-96 (isomer A) 2-11 3-CF 3

CH

3 n-propyl CH 3 80-82 (isomer A) 2-12 4-OCF 3

CH

3

C

2

H

5

C

2

H

5 71-73 (isomer A) 2-13 4-OCF 3

CH

3

C

2

H

5

CH

3 89-81 (isomer A) 2-14 4-CF 3

CH

3 n-propyl C 2 Hs 80-82 (isomer A) 2-15 4-CI CH 3 n-propyl C 2

H

5 78-81 (isomer A) 2-16 4-CI CH 3 n-propyl CH 3 95-97 (isomer A) 2-17 4-tert-butyl CH 3 n-propyl C 2

H

5 78-80 (isomer A) 2-18 4-tert-butyl CH 3 n-propyl CH 3 57-59 (isomer A) 2-19 4-CF 3

CH

3

C

2

H

5 n-propyl 74-76 (isomer A) 2-20 4-CF 3

CH

3

C

2

H

5

CH

3 85-87 (isomer A) 2-21 4-CI CH 3 cyclopropyl C 2 Hs resin (isomer A) 2-22 4-CF 3

CH

3 cyclopropyl C 2

H

5 resin (isomer A) 2-23 2-CI, 4-CF 3

CH

3 cyclopropyl C2H 5 resin (isomer A) 2-24 2-CI, 4-CF 3

CH

3 cyclopropyl CH 3 resin (isomer A) 2-25 4-CF 3

C

2 Hs C 2

H

5

C

2 Hs resin (isomer A) 2-26 3-CF 3

C

2

H

5 n-propyl C 2 Hs resin (isomer A) 2-27 3-CF 3

C

2

H

5

C

2

H

5

C

2

H

5 resin (isomer A) 2-28 4-CF 3

CH

3

C

2 H CH 2 -C-CH 80-83 (isomer A) 2-29 4-CF 3

CH

3

C

2 Hs CH 2

-C=CH

2 102-104 (isomer A) 2-30 4-CF 3

CH

3

C

2

H

5 i-propyl 101-102 (isomer A) 2-31 4-CF 3

CH

3

C

2

H

5 n-butyl Harz (isomer A) 2-32 3-CF 3

CH

3

C

2 Hs n-propyl 2-33 3-CF 3

CH

3

C

2 Hs n-butyl 2-34 3-CF 3

CH

3

C

2

H

5 i-propyl 2-35 3-CF 3

CH

3

C

2

H

5

CH

2 -C-CH 2-36 3-CF 3

CH

3

C

2 H CH 2

-C=CH

2 2-37 4-OCF 3

CH

3

C

2 Hs n-propyl 2-38 4-OCF 3

CH

3

C

2 Hs n-butyl WO 98/54126 PCT/EP98/03074 - 32 Compd. (R 6 )n R, R2 A-R 7 Phys. data 2-39 4-OCF 3

CH

3

C

2

H

5 i-propyl 2-40 4-OCF 3

CH

3

C

2

H

5

CH

2 -C=-CH 2-41 4-OCF 3

CH

3

C

2

H

5

CH

2

-C=CH

2 2-42 3-CI, 4-CF 3

CH

3

C

2 Hs CH 3 2-43 3-CI, 4-CF 3

CH

3

C

2

H

5

C

2

H

5 2-44 4-Cl, 3-CF 3

CH

3

C

2 Hs CH 3 2-45 4-CI, 3-CF 3

CH

3

C

2 Hs C 2 Hs Table 2.2: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4

CF

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.3: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 3

CF

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.4: Compounds of general formula (1.2) wherein R , is methyl, R 2 is ethyl, (R 6 )n is 2

CF

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.5: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.6: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 3-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.7: Compounds of general formula (I.2) wherein R, is methyl, R 2 is ethyl, (R 6 )n is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.8: Compounds of general formula (1.2) wherein R , is methyl, R 2 is ethyl, (R 6 ), is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.9: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.10: Compounds of general formula (1.2) wherein R , is methyl, R 2 is ethyl, (R 6 )n is 2 Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.11: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4 F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.12: Compounds of general formula (I.2) wherein R, is methyl, R 2 is ethyl, (R 6 ), is 3 F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.13: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 2 F and the substituent A-R 7 corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 33 Table 2.14: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4 tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.15: Compounds of general formula (I.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4

O-CF

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.16: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4

O-CH

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.17: Compounds of general formula (I.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4

O-C

2

H

5 and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 2.18: Compounds of general formula (1.2) wherein R , is methyl, R 2 is ethyl, (R 6 )n is 4 O-n-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.19: Compounds of general formula (1.2) wherein R, is methyl, R 2 is ethyl, (R 6 )n is 4

CH

3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.20: Compounds of general formula (1.2) wherein R , is methyl, R 2 is ethyl, (R 6 ), is 4

C

2 Hs and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.21: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is n-propyl, (R 6 ), is 4-C 3

H

7 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.22: Compounds of general formula (I.2) wherein R, is methyl, R 2 is n-propyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.23: Compounds of general formula (1.2) wherein R , is methyl, R 2 is n-propyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 2.24: Compounds of general formula (1.2) wherein R 2 is n-propyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.25: Compounds of general formula (1.2) wherein R , is methyl, R 2 is n-propyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.26: Compounds of general formula (I.2) wherein R, is methyl, R 2 is n-propyl, (R 6 )n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.27: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is cyclopropyl,

(R

6 )n is 4-CF 3 and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 2.28: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is cyclopropyl,

(R

6 )n is 3-CF 3 and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 2.29: Compounds of general formula (1.2) wherein R , is methyl, R 2 is cyclopropyl,

(R

6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.30: Compounds of general formula (1.2) wherein R , is methyl, R 2 is cyclopropyl,

(R

6 )n is 4-tert-butyl and the substituent A-R 7 , corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 34 Table 2.31: Compounds of general formula (1.2) wherein R 1 is methyl, R 2 is cyclopropyl,

(R

6 )n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.32: Compounds of general formula (I.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 3 CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 2.33: Compounds of general formula (I.2) wherein R 1 is methyl, R 2 is ethyl, (R 6 )n is 4-CI, 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.1: Compounds of formula N CONHCHz ,

CH

3 0 N CONHCH NI A-RF (I.3) ,N I I IR 2 O -(R 6 )n Compd. (R 6 )n R2 A-R 7 Phys. data 3-1 3-CF 3

C

2 Hs C 2

H

5 113-115 (isomer A) 3-2 3-CF 3

C

2 Hs CH 3 136-138 (isomer A) 3-3 4-CI C 2 Hs C 2 Hs 130-132 (isomer A) 3-4 4-CI C 2 Hs CH 3 125-127 (isomer A) 3-5 4-tert-butyl C 2 Hs C 2

H

5 95-97 (isomer A) 3-6 4-tert-butyl C 2 Hs CH 3 106-107 (isomer A) 3-7 3,4-CI012 C 2

H

5

C

2 Hs 102-104 (isomer A) 3-8 3,4-CI2 C 2 Hs CH 3 141-144 (isomer A) 3-9 3-CF 3 n-propyl C 2 Hs 99-191 (isomer A) 3-10 3-CF 3 n-propyl CH 3 122-124 (isomer A) 3-11 4-OCF 3

C

2 Hs C 2

H

5 95-98 (isomer A) 3-12 4-OCF 3

C

2 Hs CH 3 105-106 (isomer A) 3-13 4-CF 3 n-propyl C 2

H

5 118-120 (isomer A) 3-14 4-CI n-propyl C 2

H

5 105-107 (isomer A) 3-15 4-Cl n-propyl CH 3 122-124 (isomer A) 3-16 4-tert-butyl n-propyl C 2

H

5 100-102 (isomer A) 3-17 4-tert-butyl n-propyl CH 3 108-110 (isomer A) 3-18 4-CF 3

C

2

H

5 n-propyl 95-97 (isomer A) 3-19 4-CF 3

C

2

H

5

C

2 Hs 113-115 (isomer A) 3-20 4-CF 3

C

2

H

5

CH

3 120-122 (isomer A) WO 98/54126 PCT/EP98/03074 - 35 Compd. (R 6 )n R2 A-R 7 Phys. data 3-21 2-CI, 4-CF 3 cyclopropyl C 2

H

5 128-130 (isomer A) 3-22 2-CI, 4-CF 3 cyclopropyl CH 3 131-133 (isomer A) 3-23 4-CF 3

C

2

H

5

CH

2 -C=-CH 73-75 (isomer A) 3-24 4-CF 3

C

2 Hs CH 2

-C=CH

2 89-91 (isomer A) 3-25 4-CF 3

C

2 Hs i-propyl 114-116 (isomer A) 3-26 4-CF 3

C

2

H

5 n-butyl 96-97 (isomer A) 3-27 3-CF 3

C

2

H

5 n-propyl 3-28 3-CF 3

C

2

H

5 n-butyl 3-29 3-CF 3

C

2

H

5 i-propyl 3-30 3-CF 3

C

2

H

5

CH

2 -C=-CH 3-31 3-CF 3

C

2 Hs CH 2

-C=CH

2 3-32 4-OCF 3

C

2

H

5 n-propyl 3-33 4-OCF 3

C

2

H

5 n-butyl 3-34 4-OCF 3

C

2

H

5 i-propyl 3-35 4-OCF 3

C

2 Hs CH 2 -C=CH 3-36 4-OCF 3

C

2 Hs CH 2

-C=CH

2 3-37 3-CI, 4-CF 3

C

2

H

5

CH

3 3-38 3-CI, 4-CF 3

C

2

H

5

C

2 Hs 3-39 4-CI, 3-CF 3

C

2 Hs CH 3 3-40 4-CI, 3-CF 3

C

2

H

5

C

2

H

5 Table 3.2: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.3: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.4: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 2-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.5: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.6: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 3-CI and the substituent A-R 7 , corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 36 Table 3.7: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 2-Cl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.8: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.9: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.10: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 2-Br and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.11: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.12: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 3-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.13: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 2-F and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.14: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 , corresponds in each case to a line of Table A. Table 3.15: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.16: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.17: Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 )n is 4-O-C 2

H

5 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.18: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-O-n-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.19: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 4-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.20: Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 )n is 4-C 2 Hs and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.21: Compounds of general formula (I.3) wherein R 2 is n-propyl, (R 6 )n is 4-C 3

H

7 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.22: Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.23: Compounds of general formula (I.3) wherein R 2 is n-propyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.

WO 98/54126 PCT/EP98/03074 - 37 Table 3.24: Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.25: Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.26: Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 )n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.27: Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 )n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.28: Compounds of general formula (I.3) wherein R 2 is cyclopropyl, (R 6 )n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.29: Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 )n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.30: Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 )n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.31: Compounds of general formula (I.3) wherein R 2 is cyclopropyl, (R 6 )n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.32: Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 )n is 3-CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 3.33: Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 )n is 4-CI, 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A. Table 4.1: Compounds of formula O

CH

3 O Xj Y N OA-R7 . O oN (I.4)

R

2 R2O'- (R 6

)

n Compd. (R 6 )n R2 X Y A-R 7 Phys. data 4-1 3-CF 3

C

2 Hs CH O-CH 3

C

2

H

5 4-2 3-CF 3

C

2

H

5 CH O-CH 3

CH

3 4-3 3-CF 3

C

2

H

5 N O-CH 3

C

2 H 4-4 3-CF 3

C

2 Hs N O-CH 3

CH

3 WO 98/54126 PCT/EP98/03074 - 38 Compd. (R 6 )n R2 X Y A-R 7 Phys. data 4-5 3-CF 3

C

2

H

5 N NH-CH 3

C

2

H

5 4-6 3-CF 3

C

2

H

5 N NH-CH 3

OH

3 4-7 2-CF 3

C

2 Hs CH O-CH 3

C

2 Hs 4-8 2-CF 3

C

2 Hs CH O-CH 3

CH

3 4-9 2-CF 3

C

2 Hs N O-CH 3

C

2 Hs 4-10 2-CF 3

C

2 Hs N O-CH 3

CH

3 4-11 2-CF 3

C

2 Hs N NH-CH 3

C

2

H

5 4-12 2-CF 3

C

2 Hs N NH-CH 3

CH

3 4-13 4-CF 3

C

2 Hs CH O-CH 3

C

2

H

5 4-14 4-CF 3

C

2

H

5 CH O-CH 3

CH

3 4-15 4-CF 3

C

2 Hs N O-CH 3

C

2

H

5 4-16 4-CF 3

C

2

H

5 N O-OH 3

CH

3 4-17 4-CF 3

C

2

H

5 N NH-CH 3

C

2 Hs 4-18 4-CF 3

C

2 Hs N NH-CH 3

CH

3 4-19 4-OCF 3

C

2 Hs CH O-CH 3

C

2

H

5 4-20 4-OCF 3

C

2

H

5 CH O-CH 3

CH

3 4-21 4-OCF 3

C

2

H

5 N O-CH 3

C

2 Hs 4-22 4-OCF 3

C

2

H

5 N O-CH 3

CH

3 4-23 4-OCF 3

C

2 Hs N NH-CH 3

C

2 Hs 4-24 3-OCF 3

C

2 Hs N NH-CH 3

CH

3 4-25 3-OCF 3

C

2 Hs CH O-CH 3

C

2 Hs 4-26 3-OCF 3

C

2 Hs CH O-CH 3

CH

3 4-27 3-OCF 3

C

2 Hs N O-CH 3

C

2 Hs 4-28 3-OCF 3

C

2 Hs N O-CH 3

CH

3 4-29 3-OCF 3

C

2

H

5 N NH-CH 3

C

2

H

5 4-30 3-OCF 3

C

2

H

5 N NH-CH 3

CH

3 4-31 4-CI C 2 Hs CH O-CH 3

C

2

H

5 4-32 4-Cl C 2

H

5 CH O-OH 3

OH

3 4-33 4-Cl C 2 Hs N O-CH 3

C

2

H

5 4-34 4-Cl C 2 Hs N O-CH 3

CH

3 4-35 4-CI C 2

H

5 N NH-CH 3

C

2

H

5 4-36 4-Cl C 2 Hs N NH-CH 3

CH

3 WO 98/54126 PCT/EP98/03074 - 39 Compd. (R 6 )n R2 X Y A-R 7 Phys. data 4-37 3-CI C 2

H

5 CH O-CH 3

C

2 Hs 4-38 3-CI C 2

H

5 CH O-CH 3

CH

3 4-39 3-CI C 2

H

5 N O-CH 3

C

2

H

5 4-40 3-CI C 2 Hs N O-CH 3

CH

3 4-41 3-CI C 2

H

5 N NH-CH 3

C

2 Hs 4-42 3-CI C 2 Hs N NH-CH 3

CH

3 4-43 4-tert-butyl C 2 Hs CH O-CH 3

C

2 Hs 4-44 4-tert-butyl C 2 Hs CH O-CH 3

CH

3 4-45 4-tert-butyl C 2

H

5 N O-CH 3

C

2

H

5 4-46 4-tert-butyl C 2

H

5 N O-CH 3

CH

3 4-47 4-tert-butyl C2H 5 N NH-CH 3

C

2

H

5 4-48 4-tert-butyl C 2 Hs N NH-CH 3

CH

3 4-49 4-F C2H 5 CH O-CH 3

C

2 Hs 4-50 4-F C 2 Hs CH O-CH 3

CH

3 4-51 4-F C 2 Hs N O-CH 3

C

2

H

5 4-52 4-F C 2 Hs N O-CH 3

CH

3 4-53 4-F C 2 Hs N NH-CH 3 C2H5 4-54 3-F C 2 Hs N NH-CH 3

CH

3 4-55 3-F C 2 Hs CH O-OH 3 C2H 5 4-56 3-F C2H 5 CH O-OH 3

CH

3 4-57 3-F C2H 5 N O-CH 3

C

2 Hs 4-58 3-F C 2 Hs N O-CH 3

CH

3 4-59 3-F C 2 Hs N NH-CH 3

C

2 Hs 4-60 3-F C 2 Hs N NH-CH 3

CH

3 4-61 4-CF 3 cyclopropyl N O-CH 3 C2H 5 resin 4-62 4-CF 3 cyclopropyl N NH-CH 3

C

2

H

5 foam Table A Compound No. A-R 7 A.1 CH 3 A2 C 2 Hs A.3 n-C3H 7 WO 98/54126 PCT/EP98/03074 - 40 A.4 iSO-C 3

H

7 M. n-C 4

H

9 A.6 n-C 6

H

13 A.7 CH 2 F A.8 CHF 2 A.9 CH 2

CF

3 A.10 CH 2

CH=CH

2 A.1 1 CH 2

CH=CHCH

3 A.12 CH 2

CH=C(CH

3

)

2 A.13 CH 2 CH=CHCI A.14 CH 2 CH=CC1 2 A.15 CH 2

C(CH

3

)=CH

2 A.16 CH 2 C=-CH A.17 CH 2 Si(CH 3

)

3 A.1 8 CH 2 -CYClopropyl-2,2-CI 2 A.1 9 0H 2 -CYClopropyl A.20 CH 2 CN A.21 CH 2 000CH 3 A.22 CH 2 000C 2

H

5 A.23 CH 2 COO-iSO-C 3

H

7 A.24 CH(CH 3

)COOC

2

H

5 A.25 C(=O)0C 2

H

5 A.26 C(=O)NHCH 3 A27 C(=O)C(=O)0C 2

H

5 A.28 CH 2

C

6

H

5 A.29 CH 2

C

6

H

4 -2-F A.30 CH 2 0 6

H

4 -3-F A.31 CH 2

C

6

H

4 -4-F A.32 0H 2

C

6

H

4 -2-CI A.33 CH 2

C

6

H

4 -3-CI A.34 CH 2

C

6

H

4 -4-CI A.35 CH 2

C

6

H

4 -2-Br A.36 CH 2

C

6

H

4 -3-Br WO 98/54126 PCT/EP98/03074 -41 A.37 CH 2

C

6

H

4 -4-Br A.38 CH 2

C

6

H

4 -2-CF 3 A.39 CH 2

C

6

H

4 -3-CF 3 A.40 CH 2

C

6

H

4 -4-CF 3 Biological Examples A) Microbicidal action Example B1: Action against Phytophthora infestans on tomatoes a) Curative action After a cultivation period of three weeks, tomato plants of the "Red Gnome" variety are sprayed with a zoospore suspension of the fungus and incubated in a humidity chamber at 18 to 200C and saturated humidity. Humidifying is discontinued after 24 hours. When the plants have dried off, they are sprayed with a mixture prepared from a wettable powder formulation of the test compound at a concentration of 200 ppm. After the spray-coating has dried, the plants are again placed in the humidity chamber for 4 days. The number and size of the typical leaf specks that have appeared after that time serve as a measure for evaluating the effectiveness of the test compounds. b) Preventive-systemic action A wettable powder formulation of the test compound is poured at a concentration of 60 ppm (based on the volume of soil) onto the surface of the soil in which three-week-old tomato plants of the "Red Gnome" variety have been potted. After a waiting period of three days, the undersides of the leaves of the plants are sprayed with a zoospore suspension of Phytophthora infestans. The treated plants are then placed in a spraying cabinet for 5 days at 18 to 200C and saturated humidity. After that period, typical leaf specks appear, the number and size of which are used to evaluate the effectiveness of the test compounds. Whereas infestation in untreated and infected control plants is 100%, with the compounds from Tables 1 to 4 infestation is reduced to 20% or less in both tests. In particular, with compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 infestation is still fully suppressed even at a concentration of 20 ppm of the test compound.

WO 98/54126 PCT/EP98/03074 -42 Example B2: Action against Plasmopara viticola (Bert. et Curt.) (Berl. et DeToni) on vines a) Residual-preventive action Vine cuttings of the "Chasselas" variety are cultivated in a greenhouse. At the 10-leaf stage, 3 plants are sprayed with a mixture comprising the active ingredient in a concentration of 200 ppm. After the spray-coating has dried, the plants are uniformly infected on the undersides of the leaves with a spore suspension of the fungus. The plants are then kept in a humidity chamber for 8 days. After that time, distinct disease symptoms appear in the control plants. The number and size of the infection sites on the treated plants serve as a measure for evaluating the effectiveness of the test compounds. b) Curative action Vine cuttings of the "Chasselas" variety are cultivated in a greenhouse and are infected at the 10-leaf stage, on the undersides of the leaves, with a spore suspension of Plasmopara viticola. After being kept in a humidity chamber for 24 hours, the plants are sprayed with a mixture comprising the active ingredient in concentrations of 200 ppm, 60 ppm and 20 ppm. The plants are then kept in the humidity chamber for a further 7 days. After that time, the disease symptoms appear in the control plants. The number and size of the infection sites on the treated plants serve as a measure for evaluating the effectiveness of the test compounds. In comparison with the control plants, the plants treated with compounds from Tables 1 to 4 exhibit an infestation of 20% or less. In particular, with the compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 complete curative action is still obtained even at a concentration of the test compound of 20 ppm. Example B3: Action against Puccinia graminis on wheat a) Residual-protective action 6 days after sowing, wheat plants are sprayed to drip point with an aqueous spray mixture (0.02% active ingredient), and infected 24 hours later with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 % relative humidity at 20 0 C), the plants are placed in a greenhouse at 220C. Evaluation of rust pustule development is made 12 days after infection.

WO 98/54126 PCT/EP98/03074 - 43 b) Systemic action Wheat plants are watered 5 days after sowing with an aqueous spray mixture (0.006% active ingredient, based on the volume of soil). Care is taken that the spray mixture does not come into contact with the parts of the plants above the soil. The treated plants are infected 48 hours later with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 % relative humidity at 200C), the plants are placed in a greenhouse at 22°C. Evaluation of rust pustule development is made 12 days after infection. Compounds from Tables 1 to 4 bring about a distinct reduction in the fungus infestation, in some cases to from 10 to 0 %. In particular, with the compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 the disease is suppressed completely (0-5% infestation). Example B4: Action against Erysiphe graminis on barley a) Residual-protective action Barley plants about 8 cm in height are sprayed to drip point with an aqueous spray mixture (0.02% active ingredient) and dusted 3 to 4 hours later with conidia of the fungus. The infected plants are placed in a greenhouse at 22 0 C. The fungus infestation is evaluated 10 days after infection. b) Systemic action Barley plants about 8 cm in height are watered with an aqueous spray mixture (0.002% active ingredient, based on the volume of soil). Care is taken that the spray mixture does not come into contact with the parts of the plants above the soil. The treated plants are dusted 48 hours later with conidia of the fungus. The infected plants are placed in a greenhouse at 22 0 C. The fungus infestation is evaluated 10 days after infection. Compounds from Tables 1 to 4 in general are able to suppress infestation with the disease to less than 20 % and, in some cases, to suppress it completely. Example B5: Action against Septoria nodorum on wheat Wheat plants are sprayed at the 3-leaf stage with a spray mixture (60 ppm a.i.) prepared from a wettable powder formulation of the test compounds.

WO 98/54126 PCT/EP98/03074 -44 24 hours later, the treated plants are infected with a conidia suspension of the fungus. The plants are then incubated for 2 days at 90-100 % relative humidity and placed in a greenhouse at 20-24 0 C for a further 10 days. Fungal infestation is evaluated 13 days after infection. Less than 1 % of the wheat plants exhibit infestation. B. Insecticidal action Example B6: Action against Aphis craccivora Pea seedlings are infested with Aphis craccivora, subsequently sprayed with a spray mixture comprising 100 ppm of the test compound and then incubated at 20 0 C. 3 and 6 days later the percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants. Compounds from Tables 1 to 4 generally exhibit good activity in this test. In particular, compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test. Example B7: Action against Diabrotica balteata Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of the test compound. After the spray-coating has dried, the maize seedlings are populated with 10 Diabrotica balteata larvae in the second stage and then placed in a plastics container. 6 days later, the percentage reduction in population (% activity) is determined by comparing the number of dead larvae on the treated plants with that on untreated plants. Compounds from Tables 1 to 4 exhibit good activity in this test. In particular, compounds 1 1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test. Example B8: Action against Heliothis virescens Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of test compound. After the spray-coating has dried, the plants are populated with 10 caterpillars of Heliothis virescens in the first stage and then placed in a plastics container. 6 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.

WO 98/54126 PCT/EP98/03074 -45 Most compounds from Tables 1 to 4 exhibit good activity in this test. In particular, compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test. Example B9: Action against Spodoptera littoralis Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of test compound. After the spray-coating has dried, the plants are populated with 10 caterpillars of Spodoptera littoralis in the third stage and then placed in a plastics container. 3 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants. Compounds from Tables 1 to 4 exhibit good activity in this test. In particular, compounds 1 1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test. C. Acaricidal action Example B10: Action against Tetranychus urticae Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed one day later with an aqueous emulsion spray mixture comprising 100 ppm of test compound. The plants are then incubated for 6 days at 25 0 C and subsequently evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on untreated plants. Compounds from Tables 1 to 4 generally exhibit good activity in this test. In particular, compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test.

Claims (29)

1. A compound of formula Z oX ,.O. A"R 7 (an R9 Y N AR K (R , R3 G R4 (Rs)q wherein either X is CHorN, Y isOR 1 and Z isO, or X is N, Y is NHR 8 and Z is 0, S or S(=O); R 1 is C1-C 4 alkyl; R 2 is C 2 -C4alkyl or C3-C 6 cycloalkyl; R 3 and R 4 are each independently of the other H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, CN, NO 2 , a (Cl-C 4 alkyl) 3 -Si group, the alkyl groups being the same or different, halogen, (C1-C4 alkyl)S(=O)m, (halo-Cj-C 4 alkyl)S(=O)m, halo-C 1 -C 4 alkyl or halo-Cl-C 4 alkoxy; R 8 is H or C 1 -C 4 alkyl; R 9 is methyl, fluoromethyl or difluoromethyl; m is 0, 1 or 2; A is a direct bond, Cs-Cloalkylene, -C(=O)-, -C(=S)- or halo-C-Co 10 alkylene and R 7 is a radical R 1 0 io; or A is C0 1 -Co 10 alkylene, -C(=O)-, -C(=S)- or halo-C 1 -Cloalkylene and R 7 is -CN, ORjo, N(Ro 10 ) 2 , the radicals Ro 1 0 being the same or different, or -S(=O)pRio; p is 0, 1 or 2; G is O, S or -O-CH 2 -, wherein the -CH 2 group is bonded to the ring denoted by K; R s and R 6 are C 1 -C 6 alkyl, halo-C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, halo-C3-C 6 cycloalkyl, CI-C6 alkoxy, halo-Cl-C 6 alkoxy, Cl-C 6 alkylthio, halo-C-C 6 alkylthio, Cl-C 6 alkylsulfynyl, halo C1-C 6 alkylsulfynyl, Cl-C 6 alkylsulfonyl, halo-C-C 6 alkylsulfonyl, Cs-C 6 alkylsulfonyloxy, halo-C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkoxy-Cl-C 6 alkyl, halo-C-C 6 alkoxy-Cl-C 6 alkyl, Cl-C 6 alkylthio-C 1 -C 6 alkyl, halo-C-Cealkylthio-C 1 -C 6 alkyl, C -C 6 alkylsulfynyl-C 1 -C 6 alkyl, halo-C 1 -C 6 alkylsulfynyl-Cl-C 6 alkyl, Cl -C 6 alkylsulfonyl-Cl-C 6 alkyl, halo-C-C 6 alkyl sulfonyl-C l -C 6 alkyl, C -C 6 alkylcarbonyl, halo-C-C 6 alkylcarbonyl, Cl-C 6 -alkoxy- WO 98/54126 PCT/EP98/03074 -47 carbonyl, halo-C 1 -C 6 alkoxycarbonyl, C1-C 6 alkylaminocarbonyl, C-C 4 alkoxyimino methyl, di(Cl-C 6 alkyl)aminocarbonyl, the alkyl groups being the same or different; C 1 -C 6 alkylaminothiocarbonyl, di(Cl-C 6 alkyl)aminothiocarbonyl, the alkyl groups being the same or different; C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, the alkyl groups being the same or different; halogen, NO 2 , CN, thioamido, trimethylsilyl, CH 2 Si(C 1 -C 4 alkyl) 3 , the alkyl groups being the same or different; an unsubstituted or mono- to tetra substituted C 1 -C 4 alkylenedioxy group, the substituents being selected from the group consisting of C 1 -C 4 alkyl and halogen; wherein, when q is greater than 1, the radicals Rs are the same or different, and when n is 2, the radicals R 6 are the same or different; and the radicals Rs and R 6 are independent of one another; n is 0, 1, 2, 3, 4 or 5; q is 0, 1,2, 3 or 4; and RIo is H, C 1 -C 6 alkyl, C2-C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cycloalkyl, or Cl-C 6 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl or C 3 -C6cycloalkyl each mono- or poly-substituted by substituents from the group consisting of halogen; or is -Si(C 1 -C 4 alkyl) 3 , the alkyl groups being the same or different; Cl-C 6 alkoxycarbonyl or an aryl or heterocyclyl group that is unsubstituted or mono- or poly-substituted by substituents from the group consisting of halogen, C 1 -C 4 alkyl and halo-C-C 4 alkyl; with the proviso that the group -G-phenyl is not 3-trifluoromethylbenzyloxy, 4-fluoro benzyloxy or 4-fluorophenoxy each in the 4-position, when simultaneously R 2 is ethyl, RI, R 8 and R 9 are methyl, R 3 and R 4 are hydrogen, q is 0, Z is oxygen and AR 7 is methyl; or, where applicable, a possible E/Z isomer, mixture of E/Z isomers and/or tautomer thereof, in each case in free form or in salt form.

2. A compound according to claim 1 of formula (I) in free form.

3. A compound according to either claim 1 or claim 2 of formula (I) wherein X is CH and Z is O.

4. A compound according to either claim 1 or claim 2 of formula (I) wherein X is N and Z is O.

5. A compound according to any one of claims 1 to 4 of formula (I) wherein Y is C 1 -C 2 alkoxy. WO 98/54126 PCT/EP98/03074 -48

6. A compound according to any one of claims 1 to 5 of formula (I) wherein R 2 is ethyl, propyl or cyclopropyl.

7. A compound according to either claim 1 or claim 2 of formula (I) wherein R 3 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, CN, NO 2 , halogen, halo-C 1 -C 4 alkyl or halo-C 1 -C 4 alkoxy.

8. A compound according to either claim 1 or claim 2 of formula (I) wherein R 4 is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, CN, NO 2 , halogen, halo-Cl-C 4 alkyl or halo-C 1 -C 4 alkoxy.

9. A compound according to either claim 1 or claim 2 of formula (I) wherein R 8 is H or Cl-C 2 alkyl.

10. A compound according to any one of claims 1 to 9 of formula (I) wherein R 9 is methyl or fluoromethyl.

11. A compound according to any one of claims 1 to 10 of formula (I) wherein R 6 is halogen, C 1 -C 4 alkyl, halo-C-C 4 alkyl, halo-C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, halo-C 3 -C 6 cycloalkyl or CH 2 Si(CH 3 ) 3 .

12. A compound according to claim 11 of formula (I) wherein n is 1 or 2.

13. A compound according to either claim 1 or claim 2 of formula (I) wherein G is oxygen.

14. A compound according to any one of claims 1 to 13 of formula (I) wherein Rs is halogen, C1-C 4 alkyl, halo-C-C 4 alkyl, halo-C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, halo-C 3 -C 6 cycloalkyl or CH 2 Si(CH 3 ) 3 .

15. A compound according to claim 14 of formula (I) wherein q is 0, 1, 2 or 3.

16. A compound according to any one of claims 1 to 15 of formula (I) wherein AR 7 is methyl or ethyl.

17. A process for the preparation of a compound of formula (I) or, where applicable, an E/Z isomer, mixture of E/Z isomers and/or tautomer thereof, wherein n, q, A, G, X, Y, Z, R 2, R 3 , R 4 , R 5 , R, R 7 and R 9 are as defined above in claim 1 for formula (I), and wherein the WO 98/54126 PCT/EP98/03074 - 49 provisos mentioned above for the compound of formula (I) apply, in each case in free form or in salt form, which process comprises al) reacting a compound of formula Z X R9O Y 0 (II), \ RI R4 wherein X, Y, Z, R 3 , R 4 and R 9 are as defined for formula (I) and X is a leaving group, with a compound of formula N 1,A 'R NsO-AR, H.O ,N R2 (111), / - (R6 n (Rs)q (R wherein n, q, A, G, R 2 , R 5 , R 6 and R 7 are as defined for formula (I); or a2) reacting a compound of formula NO' A, R7 0' I R G (IV), R2 (Rd~n (R 5 )q wherein n, q, A, G, R 2 , Rs, R 6 and R 7 are as defined for formula (I), with a compound of formula Z RcO, z \ - ONH 3 CI (V, R4 wherein X, Y, Z, R, R 4 and R 9 are as defined for formula (I); or a3) reacting a compound of formula WO 98/54126 PCT/EP98/03074 - 50 Z cX , OH (R 6 ) n RY N S/ (VI), 3R 0 G R4 (R 5 )q wherein n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 8 and Re are as defined above for formula (I) and wherein the provisos mentioned above for the compound of formula (I) apply, with a compound of formula X,-A-R 7 (VII), wherein A und R 7 are as defined above for formula (I) and X, is a leaving group as for formula (II); b) to prepare a compound of formula (I) wherein Y is NHR 8 and Z is O, reacting a compound of formula (I) wherein Y is OR, with a compound of formula R 8 NH 2 wherein R 8 is as defined for formula (I); or c) to prepare a compound of formula (I) wherein Y is NHRe and Z is S, reacting a compound of formula (I) wherein Y is R 8 NH 2 and Z is O with P 4 S 1 0 or Lawesson's reagent; or d) to prepare a compound of formula (I) wherein Z is SO, reacting a compound of formula (I) wherein Z is S with an oxidising agent.

18. A process for the preparation of a compound of formula (III), as defined in claim 17, in each case in free form or in salt form, which process comprises e) reacting a compound of formula (IV), as defined in claim 17, wherein n, q, A, G, R 2 , Rs, R 6 and R 7 are as defined in claim 1 for formula (I), with H 2 NOH or with a salt thereof; or f) reacting a compound of formula OH O N R2G(Rs)q G (R6) n (VIII), -2 (Rd.~ (R 5 )q 7 WO 98/54126 PCT/EP98/03074 -51 wherein n, q, G, R 2 , Rs, and R 6 are as defined above in claim 1 for formula (I), with a compound of formula RAONH 2 (IX), wherein A and R 7 are as defined for formula (I).

19. A process for the preparation of a compound of formula (VI), as defined in claim 17, in each case in free form or in salt form, which process comprises g) reacting a compound of formula Z Ro X1 x y o (R6n R3 Z 11 R2x) R4 (R 5 )q wherein n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are as defined above for formula (I), with hydroxylamine.

20. A process for the preparation of a compound of formula (X), in each case in free form or in salt form, which process comprises h) reacting a compound of formula (VIII), as defined in claim 18, with a compound of formula (II), as defined in claim 17.

21. A process for the preparation of a compound of formula (VIII), as defined in claim 18, in each case in free form or in salt form, which process comprises i) reacting a compound of formula O (xx G (Xl), R2 (Rd . (Rs)q wherein n, q, G, R 2 , R 5 and R 6 are as defined in claim 1 for formula (I), with a nitrite.

22. A pesticide which comprises at least one compound according to claim 1 of formula (I) or, where applicable, an E/Z isomer or tau tomer thereof, in free form or in agrochemically acceptable salt form, as active ingredient in an effective active concentration, and at least one adjuvant. WO 98/54126 PCT/EP98/03074 - 52

23. A method of preparing a composition as described in claim 22, wherein the active ingredient is intimately mixed and/or ground with the adjuvant(s).

24. The use of a compound as described in claim 1, of formula (I), or, where applicable, of an E/Z isomer or tautomer thereof, in free form or in agrochemically acceptable salt form, in the preparation of a composition as described in claim 22.

25. The use of a compound as described in claim 1, of formula (I), or of a composition as described in claim 22, in controlling pests.

26. A method of controlling pests, wherein a compound as described in claim 1, of formula (I), or a composition as described in claim 22 is applied to the pests or to their habitat.

27. A method according to claim 26 of protecting plant propagation material, wherein the propagation material or the planting site of the propagation material is treated.

28. Plant propagation material treated according to the method described in claim 27.

29. A compound of formula N, O.' A-R7 H N R 2 G (1j), / - (R6)n (Rs)q wherein n, q, A, G, R 2 , R 5 , R 6 and R 7 are as defined in claim 1 for formula (I), or, where applicable, a possible E/Z isomer, mixture of E/Z isomers and/or tautomer thereof, in each case in free form or in salt form.