WO1999015511A1 - Substituted triazines, method for producing said substituted triazines, and use of the same as pesticides and fungicides - Google Patents

Abstract

The invention relates to substituted cycloalkylamino- and cycloalkoxy-1,3,5-triazines of general formula (I), wherein Q represents optionally substituted cycloalkyl, X means O and NH, and R?1 and R2¿ represent various organic radicals. The invention also relates to a method for producing the inventive compounds, to agents containing them and to their use in combating animal pests, especially insects, spider mites, ectoparasites and helminths.

Description

description

Substituted triazines, processes for their preparation and their use as pesticides and fungicides

The invention relates to new substituted 1,3,5-triazines, processes for their preparation and their use as pesticides and fungicides.

It is already known that certain cycloalkylamino and cycloalkoxy heterocycles show insecticides, acaricidal and fungicidal activity (DE-A 42 08 254, DE-A 43 31 178, DE-A 44 17 163, DE-A 44 36 509, DE -A 44 37 137, DE-A 44 38 807, DE-A 195 239 06, DE-A 196 133 29 and DE-A 196 147 18). However, the biological activity of these compounds and their toxicity to mammals and aquatic organisms is not entirely satisfactory in all application examples.

New cycloalkylamino- and cycloalkoxy-1,3,5-triazines of the formula (I) have been found

in which the residues and groups are defined as below, which, with good plant tolerance and favorable warm-blood toxicity, are very good for combating animal pests, such as insects, arachnids, nematodes, helminths and molluscs and for combating endo- and ectoparasites in the veterinary field and for Combat harmful fungi. The invention therefore relates to compounds of formula (I) and their N-oxides and / or salts, preferably acid addition salts, wherein

R ¹ and R ^{2 are} identical or different and each is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C _r C ₆ ) haloalkyl, (C ₃ -C ₆ ) - Halocycloalkyl, halogen,

Are (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl or (C ₁ -C ₄ ) cyanoalkyl;

X represents oxygen or NH;

Q is a radical of the general formula

Q ² , Q ³ , Q ⁴ , Q ⁵ or Q ⁶ ;

wherein the carbocycle is saturated or monounsaturated; n represents an integer from 2 to 7;

R ³ and R ^{4 are} identical or different and denote hydrogen or methyl and R ^{5 is} hydrogen, (C ₁ -C ₂₀ -alkyl, (C ₁ -C ₂₀ ) haloalkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) - Alkynyl, (C _r C ₂₀ ) hydroxyalkyl, (C _r C ₂₀ ) cyanoalkyl, (C _r C ₂₀ ) nitroalkyl, (C _r C ₂₀ ) thiocyanalkyl, (C ₃ -C ₈ ) cycloalkyl , (C ₃ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl- (CC ₄ ) alkyl, (C _r C ₄ ) alkyl- (C ₃ -C ₈ ) cycloalkyl, (C _r C ₂₀ ) alkoxy, (C _r C ₂₀ ) alkoxyalky, (C ₃ -C ₈ ) cycloalkoxy, (C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkoxy, (C ₃ - C ₈ ) -cycloalkoxy- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (CrCaoJ-alkylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₁ -C ₂₀ ) alkylsulfinyl ₎ (C _r C ₂₀ ) alkylsulfonyl, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) haloalkoxy, ( C ^ C _β J-haloalkoxy- (C _r C ₄ ) -alkyl, (C ₁ -C ₈ ) -haloalkoxy- (C ₁ -C ₄ ) -haloalkyl, (C _r C ₈ ) -alkylthio- (C _r C ₄ ) -alkyl, (Ca-C ^ -cycloalkylthio-CrC ^ -alkyl, (Ca-C ^ -cycloalkyl ^ C ^ C ^ -alkylthio- (C _r C ₄ ) -al kyl, Tri ^ C ^ C ^ alkylsilyl, preferably dimethyl (C _r C ₈ ) alkylsilyl, di (C ₁ -C ₈ ) alkyl (C ₃ -C ₈ ) cycloalkylsilyl, preferably Dimethylcyclohexylsilyl, di- (C ₁ -C ₈ ) alkyl- [phenyl- (C ₁ -C ₄ ) alkyl] silyl, preferably dimethyl- [phenyl- (C ₁ -C ₄ ) alkyl] silyl, dimethyl- [mono-, di-, or ths-oxa- (C _r C ₁₂ ) -alkyl] -silyl, [(C _r C ₈ ) -alkyldimethylsilyl] - (C _r C ₈ ) -alkyl, dimethylphenylsilyl, a group of the formula (II)

(ll)

Halogen, cyano, thiocyano, nitro, aryl, aryl- (C _r C ₄ ) -alkyl, aryl- (C ₂ -C ₄ ) -alkenyl, aryl- (C ₂ -C ₄ ) -alkynyl, heteroaryl, heteroaryl ^ C ^ C ^ -alkyl, aryloxy, heteroaryloxy, aryl- (C ₁ -C ₄ ) -alkoxy, heteroaryl- (C ₁ -C ₄ ) -alkoxy, arylthio, heteroarylthio, ary CpC -alkylthio, heteroaryl- (C., - C ₄ ) alkylthio, aryloxy- (C ₁ -C ₄ ) alkyl, aryl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, heteroaryloxy- (C _r C ₄ ) alkyl , Heteroaryl ^ CC -alkoxy ^ C ^ C -alkyl, arylthio- (C _r C ₄ ) -alkyl, aryl- (C _r C ₄ ) -alkylthio - ^ - C ^ -alkyl, heteroarylthio- (C _r C ₄ ) -alkyl, heteroaryC ^ CJ-alkylthio- (C _r C ₄ ) -alkyl, -CO-R ⁶ , -COOR ⁶ , -CONR ^ R ⁷ ,

R ⁶ , R ^{6 '} , R ^{7 are} identical or different and are hydrogen, (C ₁ -C ₂₀ ) -alkyl, (C ^ C ^) - haloalkyl, (C ₃ -C ₈ ) -cycloalkenyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₈ ) -cycloalkyl- (C _r C ₄ ) -alkyl, (C ₂ -C ₂₀ ) -alkenyl, (C ₂ -C ₂₀ ) -alkynyl, aryl, aryl- (C _{r is} C ₄ ) -alkyl, aryl- (C ₂ -C ₄ ) -alkenyl, aryl- (C ₂ -C ₄ ) -alkynyl, heteroaryl, heteroaryl- (C _r C ₄ ) -alkyl or R ⁶ and R ⁷ together form a ring system of the formula (III) or (IV),

wherein

D is saturated or aromatic; m is an integer from 2 to 7; q and r are identical or different and are integers between 0 and 4, the sum of which gives a number from 2 to 4, and in (III) a —CH ₂ unit is optionally replaced by oxygen, sulfur or a grouping NR ⁹ , R ⁸ and R ^{9 are the} same or different and are hydrogen, (C ^ Czoi-alkyl, (CC ₂₀ ) -

Haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₂₀ ) alkoxy, (C ^ C ^ alkylthio, phenyl-

(C 1 -C 4 -alkyl or phenyl, where all radicals Q ¹ R ³ , R ⁴ and R ^{5 must} not simultaneously be hydrogen;

Q ²

preferably a cyclohexane system, R ^{4 has} the meanings given above; Z is a group = CHR ¹⁰ , = NOR ¹⁰ , or

wherein

R) ¹ 1 ⁰ 0 diiae n okbeonn z -TUu D R6 ⁶ has the meanings given and

U is a direct bond or the group -CH ₂ O-; Q ³

(Q) means

wherein

R ^{4 has} the meanings given above,

V is a direct bond, oxygen, S (O) _{01 2} , OSO ₂ or SO ₂ O or VR ^{11 is} one

Group OC (= O) NR ⁶ R ⁶ and R ^{6 "} , R ⁶ and R ^{11 have} the meanings given above for R ⁶ ; and in the aromatic part of the condensed ring system of Q ³ optionally up to three, in the case of fluorine all hydrogen atoms are replaced by identical or different substituents;

(0 *) means

wherein

R ^{4 has} the meanings given above,

A is a direct bond, oxygen or sulfur,

B represents CH ₂ , oxygen or sulfur, where in Q ⁴ at least one of the units A or B is oxygen or

Must be sulfur, R ^{12 has} the meanings given above for R ⁶ , and if Q ⁴ is a

6-membered ring system, the radical R ^{12 is} preferably in the cis position with respect to the pyrimidinyl-amino or -oxy radical, Q ⁵

(CH ₂ ) _{1, 2} or 3

CH N R13 (Q ⁵ )

~ {CH ₂ ), 2 or 3

preferably the piperidine system;

R ^{13 represents} aryl, heteroaryl, -CO-OR ¹⁴ , -CS-OR ¹⁴ or -CS-SR ¹⁴ ; R ¹⁴ (C _r C ₂₀ ) alkyl, (C ^ C ^ haloalkyl, aryl- (C ₁ -C ₄ ) alkyl, aryl or

Heteroaryl means; where in all compounds of the formula (I) phenyl, aryl and heteroaryl radicals can be unsubstituted or substituted with up to three, in the case of fluorine as a substituent also up to the maximum number, further radicals, and in all to Q ¹ - Q ⁶ , preferably Q ¹ - Q ⁴ called alkyl, cycloalkyl, alkenyl or alkynyl groups and all groups derived therefrom which hydrogen atoms can partly, in the case of fluorine also completely, be replaced by halogen atoms, and in all to Q ¹ - Q ⁶ , preferably Q. ¹ - Q ⁴ , alkyl, alkenyl and alkynyl groups up to three non-adjacent saturated carbon units can be replaced by oxygen or the grouping S (O) _{0 Λ 2} or Si (CH ₃ ) ₂ .

Symbols and indices in formula (I) preferably have the following meanings:

R ¹ is preferably hydrogen or methyl, particularly preferably hydrogen.

R ² is preferably (C _r C ₄ ) alkyl, (C _r C ₄ ) haloalkyl or (C ₁ -C ₄ ) alkoxyalkyl, particularly preferably methyl, ethyl, n-propyl or isopropyl. R ³ , R ⁴ are preferably hydrogen.

X is preferably NH.

Q is preferably Q ¹ .

Residues Q ¹ in which the carbocycle is saturated are preferred.

Also preferred are radicals Q ¹ in which n is 5; the radical R ⁵ then preferably occupies position 4 on the cyclohexyl ring.

R ⁵ is preferably (C _r C ₁₂ ) alkyl. (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₆ ) cycloalkyl, methyl (C ₃ -C ₈ ) cycloalkyl, (CC ₈ ) alkoxy, (C ₁ -C ₈ ) alkoxy- ( C ₁ -C ₄ ) alkyl, (C _r C ₈ ) alkoxy, tri- (C ₁ -C ₅ ) alkylsilyl, preferably dimethyl- (C ₁ -C ₅ ) alkylsilyl, di- (C _r C ₅ ) alkyl- (C ₃ -C ₆ ) cycloalkylsilyl, preferably dimethylcyclohexylhexylsilyl, dimethyl- [mono-, di- or tris-oxa- (C ₁ -C ₁₂ ) alkyl] -silyl,

- (C _r C ₅ ) -alkyl, a group of the formula (II)

4 xtet 5 (ll)

Aryl, aryl (C ₁ -C ₄ ) alkyl, aryloxy (C _r C ₄ ) alkyl, aryl (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl, the above listed aryl or heteroaryl radicals and the radicals derived therefrom may be unsubstituted or substituted with up to three, in the case of fluorine, up to the maximum number of identical or different radicals, -CO-R ⁶ , -COOR ⁶ , -CO-NR ^ R ⁷ .

R ⁵ is particularly preferred (C ^ C ^ alkyl, (C ^ C ^ haloalkyl, (C ₃ -C ₆ ) cycloalkyl, methyl (C ₃ -C ₈ ) cycloalkyl, (C _r C ₈ ) - Alkoxy, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl, tri- (C ₁ -C ₅ ) alkylsilyl, preferably dimethyl- (C ₁ -C ₅ ) alkylsilyl, dimethyl- [ mono-, di-, or tris-oxa - ^ - C ^ -alkylj-silyl, a group of the formula (II)

Aryl, aryl- (C ₁ -C ₄ ) -alkyl, aryloxy- (C ₁ -C ₄ ) -alkyl, the aryl or heteroaryl radicals listed above and the radicals derived therefrom unsubstituted or with up to three, in the case of fluorine can also be provided with the same or different residues up to the maximum number.

R ⁶ , R ^{6 '} , R ⁷ are preferably identical or different hydrogen, (C ₁ -C ₅ ) alkyl, aryl or R ^e and R ⁷ together form a ring system of the formula (III) or (IV), in the case of Formula (IV) preferably a tetrahydroisoquinoline system; m is preferably 4 or 5.

R ⁸ is preferably hydrogen, (C ₁ -C ₅ ) alkyl, benzyl or phenyl.

Phenyl, aryl or heteroaryl radicals and radicals derived therefrom are preferably unsubstituted or provided with one or more, preferably up to three, substituents.

In all of the alkyl, cycloalkyl, alkenyl or alkynyl groups mentioned in Q ¹ and all groups derived therefrom, hydrogen atoms can be replaced in part, in the case of fluorine completely, by halogen atoms, and - in all alkyl mentioned in Q ¹ , Alkenyl and alkynyl groups up to three non-adjacent carbon units can be replaced by oxygen or the grouping S (O) _{0> 1ι2} or Si (CH ₃ ) ₂ .

In all cases in which Q ^{1 is} a cyclohexyl group and in which a radical R ³ , R ⁴ , R ⁵ other than hydrogen occupies the 4-position with respect to the triazinylamino or alkoxy radical, the cis configuration of these substituents is preferred .

Q ¹ is particularly preferably a cyclohexyl group, R ³ and R ⁴ are hydrogen, the radical R ⁵ is in the 4-position with respect to the triazinylamino or alkoxy radicals and the two radicals on the cyclohexyl ring are in the cis position. The following groups of compounds of the formula (Ia) - (If) are also preferred.

where the symbols and indices have the meanings given above.

In the above formula, "halogen" means a fluorine, chlorine, bromine or iodine atom; under the expression "(C ₁ -C ₄ ) alkyl" an unbranched or branched

Hydrocarbon residue with 1 to 4 carbon atoms, e.g. the methyl, ethyl,

To understand propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical; under the expression (C ₁ -C ₆ ) alkyl, the abovementioned alkyl radicals and, for example, the n-pentyl, 1-methylbutyl, 2-methylbutyl or the 1, 1-dimethylpropyl radical; under the expression "(C ^ C ^ alkyl" the aforementioned alkyl radicals and, for example, the

Hexyl, heptyl, octyl or 1, 1, 3,3-tetramethylbutyl radical, under the expression "(C ₁ -C ₁₂ )" - alkyl ", the aforementioned radical and, for example, the

Nonyl, decyl, undecyl or dodecyl radical; under the expression "(C ₁ -C ₂₀ ) alkyl" the aforementioned alkyl radicals and, for example, the

Pentadecyl or eicosyl residue; under the expression "(C ₁ -C ₄ ) haloalkyl" one under the expression "(C ₁ -C ₄ ) alkyl" Said alkyl group in which one or more hydrogen atoms are replaced by the above halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl group, the 1-fluoroethyl group, the

2-fluoroethyl group, the 1-fluoroisopropyl group, the 2,2,2-trifluoroisopropyl group, the 3,3,3-trifluoro-n-propyl group, the 2,2,2-trifluoroethyl group, the chloromethyl,

Fluoromethyl group, the difluoromethyl group or the 1,2,2-tetrafluoroethyl group; for example, under the expression "(C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl"

1-methoxyethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a

Methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or one

4-butoxybutyl group; under the expression "(C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) fluoroalkyl group a (C ₁ -C ₄ ) alkoxy-

(C ^ C ^ alkyl group in which one or more, at most all, preferably up to three, hydrogen atoms in the (C ^ C alkyl part are replaced by fluorine, e.g. the 2,2,2-

Trifluoro-1-methoxymethyl or the 1,1,1-trifluoro-2-methoxy-2-propyl group; under the expression "(C _r C ₄ ) alkoxy" an alkoxy group whose

Hydrocarbon radical that specified under the expression "(C ₁ -C ₄ ) alkyl"

Has meaning; under the expression "(C ₂ -C ₄ ) alkenyl ^M, for example the vinyl, allyl, 2-methyl-2-propene or

2-butenyl group; under the expression "(C ₂ -C ₂₀ ) alkenyl" the abovementioned radicals and, for example, the 2-pentenyl, 2-decenyl or the 2-eicosenyl group; under the expression "(C ₂ -C ₄ ) alkynyl", for example the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group;

under the expression "(C ₂ -C ₂₀ ) alkynyl" the abovementioned radicals and, for example, the 2-pentynyl or the 2-decynyl group; under the terms "(C ₁ -C ₂₀ ) hydroxyalkyl", "(C ₁ -C ₂₀ ) cyanoalkyl," (C _r C ₂₀ ) -

Nitroalkyl "," (CC ₂₀ ) -thiocyanalkyl "eg one of the aforementioned (C _r C ₂ o) -

Alkyl groups in which one hydrogen is replaced by the nitro, cyano, thiocyano or hydroxyl group; under the expression "(C ₃ -C ₈ ) cycloalkyl" the cyclopropyl, cyclobutyl or Cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical; under the expression "(C ₃ -C ₈ ) cycloalkenyl", for example a cyclobutenyl, cyclopentenyl,

Cyclohexenyl, cycloheptenyl or cyclooctenyl group; under the expression "(C ₅ -C ₆₎ cycloalkenyl" the cyclopentenyl or cyclohexenyl

Group; under the expression "(C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkyl", for example cyclopropylmethyl,

Cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl or cyclohexylbutyl radical; under the expression "(CC ^ alkyl - ^ - C ^ cycloalkyl, for example the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-methylcyclobutyl or the 4- tert-butyl-cyclohexyl group; under the expression "(C ₁ -C ₂₀ ) alkoxy" an alkoxy group, the

Hydrocarbon radical that specified under the expression "(C ₁ -C ₂₀ ) alkyl"

Has meaning; under the expression "(C ₂ -C ₂₀ ) alkoxyalkyl" an alkyl group containing up to 21 carbon atoms in which a non-terminal carbon atom

Oxygen is replaced, e.g. the methoxy-methyl, -ethyl, -propyl-, -butyl-, -hexyl-,

-decyl or -nonadecyl group, or the ethoxymethyl, propoxymethyl,

Isopropoxymethyl, butoxymethyl, tert-butoxymethyl, octyloxymethyl, ethylethoxy or the butoxybutyl group; under the expression "(C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl for example the methoxymethyl,

Ethoxymethyl, 1-methoxy, ethyl, 2-methoxy-ethyl, 1-methoxy-propyl, 3-methoxy-propyl, 1-methoxy-isopropyl, 2-methoxy-isopropyl, hexyloxy-methyl - or

2-octyloxy-ethyl group;

under the expression "(C ₃ -C ₈ ) -cycloalkoxy" or "(C ₃ -C ₈ ) -cycloalkylthio" one of the above-mentioned (C ₃ -C ₈ ) -cycloalkyl radicals which are linked via an oxygen or sulfur atom are; under the expression "(C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkoxy, for example the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group; under the expression" ( Ca-C ^ -Cycloalkoxy - ^ - C -alkyl e.g. the cyclopropoxy- methyl, cyclohexyloxymethyl, cyclooctyloxymethyl or the cyclohexyloxyethyl

Group; under the expression "(C ₃ -C ₈ ) cycloalkyl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl" for example the

Cyclopropylmethoxymethyl-, Cyclobutylmethoxymethyl- or

Cyclohexylmethoxymethyl group; under the expression "(C ₃ -C ₈ ) cycloalkylthio (C _r C ₄ ) alkyr for example the

Cyclopentylthiomethyl, cyclohexylthiomethyl or the cyclohexylthioethyl group; under the expression "(C ^ C ^ -alkylthio") an alkylthio group, the

Hydrocarbon residue that specified under the expression "(C, -C ₄ ) alkyr

Has meaning; under the expression "(C ₁ -C ₄ ) alkylsulfinyl", for example the methyl, ethyl, propyl,

Isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfinyl group; under the expression "(C ₁ -C ₄ ) alkylsulfonyl ^M, for example the methyl, ethyl, propyl,

Isopropyl, butyl, isobutyl, sec-butyl or tert-butylsulfonyl group; under the expression "(C ^ C ^ alkylthio - ^ - C alkyl" for example

Methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl,

2-ethylthioethyl or 3-methylthiopropyl; under the expression "(Ca-C ^ -cycloalkyl ^ C C -alkylthio ^ C C ^ -alkyl" e.g. the

Cyclohexylmethylthiomethyl or ethyl group; under the term "DimethyHC ^ C ^ alkylsilyl" e.g. the trimethylsilyl,

Dimethylethylsilyl-, Dimethylpropylsilyl-, Dimethylbutylsilyl- or die

Dimethyloctylsilyl group; under the expression "dimethyl-tphenyl ^ C ^ C ^ -alkylj-silyl", for example the dimethylbenzylsilyl or the dimethylphenylethylsilyl group; under the expression "dimethyl- [mono-, di- or tris-oxa- (C ₁ -C ₁₂ ) alkyl] silyl, for example the

Dimethyl-methoxymethylsilyl-, dimethyl-ethoxyethylsilyl-, dimethyl-ethoxypropylsilyl-, dimethyl-butoxypropylsilyl-, dimethyl - [(methoxyethoxy) propyl] -silyl-, dimethyl - [(ethoxyethoxy) -propyl] -silyl- or the dimethyl - [[ (ethoxyethoxy) ethoxy] propyl] silyl group; under the expression "aryl (C ₁ -C ₄ ) alkyl", for example the benzyl, the 2-phenylethyl, the 1-

Phenylethyl, the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 4- Phenylbutyl group, the 2-methyl-2-phenyl-ethyl group or the 1-methyl or 2-

Methylnaphthyl group; under the expression "aryl- (C ₂ -C ₄ ) -alkenyl" preferably the cinnamyl or styryl

Rest; under the expression "aryl- (C ₂ -C ₄ ) alkynyl", for example phenyl-ethynyl or

Phenylpropargyl residue; under the expression "heteroaryl" a heteroaromatic ring system, under

"heteroaromatic ring system" means an aryl radical in which at least one CH group is replaced by N and / or at least two adjacent CH groups are replaced by S,

NH or O are replaced, e.g. a residue of thiophene, furan, pyrrole,

Thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1, 3,4-oxadiazole,

1, 3,4-thiadiazole, 1, 3,4-triazole, 1, 2,4-oxadiazole, 1, 2,4-thiadiazole, 1, 2,4-triazole,

1, 2,3-triazole, 1, 2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole,

Benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole,

Benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole,

Dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine,

1, 3,5-triazine, 1, 2,4-triazine, 1, 2,4,5-triazine, quinoline, isoquinoline, quinoxaline,

Quinazoline, cinnoline, 1, 8-naphthyridine, 1, 5-naphthyridine, 1, 6-naphthyridine,

1, 7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine; under the term "aryl" preferably a carbocyclic aromatic radical

6 to 14, in particular 6 to 12 carbon atoms, for example phenyl, naphthyl or

Biphenylyl, preferably phenyl; under the term "heteroaryloxy" e.g. one of the heteroaryl

Residues linked via an oxygen atom; under the expression "aryl (C ₁ -C ₄ ) alkoxy", for example the benzyloxy, phenyl ethoxy

Phenylbutoxy or naphthylmethoxy group; under the expression "heteroaryl (C ₁ -C ₄ ) alkyl", for example a thienyimethyl, furylmethyl, pyridinylmethyl, pyrimidinylmethyl or thiazolylmethyl group; under the expression "heteroaryl- (C ₁ -C ₄ ) alkoxy", for example a thienylmethoxy,

Thienylethoxy or pyridinylmethoxy group; under the expression "arylthio", for example the phenylthio or the 1- or 2-naphthylthio Group; under the expression "aryloxy", for example the phenoxy or 1- or 2-naphthyloxy

Group; under the expression "heteroarylthio" one of the heteroaromatic mentioned above

Residues linked by a sulfur atom; under the expression "aryl (C ₁ -C ₄ ) alkylthio", for example the benzylthio, naphthylmethylthio or the phenylethylthio group; under the expression "HeteroaryKC ^ C ^ alkylthio" for example the thienylmethyl or

Furylmethylthio group; under the expression "aryloxy (C ₁ -C ₄ ) alkyl", for example the phenoxymethyl,

Naphthoxymethyl or phenoxyethyl group; under the expression "aryl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄₎ alkyl", for example the benzyloxymethyl,

Benzyloxyethyl, phenylethoxymethyl or phenylethoxyethyl group; under the term "heteroaryloxy - ^ - C -alkyl" e.g. a pyridinyloxymethyl,

Pyrimidinyloxymethyl or pyrimidinyloxyethyl group; under the expression Ηeteroaryl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl "for example a

Thienylmethoxymethyl, thienylmethoxyethyl, furylmethoxymethyl or

Pyridinylmethoxymethyl group; under the expression "arylthio- (C ₁ -C ₄ ) alkyl", for example the phenylthiomethyl,

Phenylthioethyl, phenylthiobutyl or naphthylthiomethyl group; under the expression "AryI- (C ₁ -C ₄ ) alkylthio- (C ₁ -C ₄ ) alkyl", for example the benzylthiomethyl,

Benzylthioethyl or naphthylmethylthiomethyl group; under the expression "heteroarylthio- (C ₁ -C ₄ ) alkyl", for example a pyridylthiomethyl,

Pyridylthioethyl, pyrimidinylthiomethyl or imidazolthiomethyl group; under the expression Ηeteroaryl- (C ₁ -C ₄ ) alkylthio- (C ₁ -C ₄ ) alkyl ", for example a

Thienylmethylthiomethyl-, furylmethylthiomethyl- or pyridinylmethylthiomethyl-

Group.

The substituents (residues) with which the various aliphatic, aromatic and heterocyclic ring systems can be provided preferably include halogen, nitro, cyano, di- (C _r C ₄ ) -alkylaminio, (C _r C ₄ ) -alkyl, (C ₃ -C ₈ ) - Cycloalkyl, (CC ₄ ) alkanoyl, (CrC ^ alkoxycarbonyl, (C ₁ -C ₄ ) trialkylsilyl, (C _r C ₄ ) alkoxy, (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₂ ) alkoxy- [CH ₂ CH ₂ O] _{1 2} ethoxy, (C _r C ₄ ) alkylthio, (C ₁ -C ₄ ) alkylsulfinyl, (C _r C ₄ ) -Alkylsulfonyl, phenyl, benzyl, phenoxy, halophenoxy, (C _r C ₄ ) -alkylphenoxy, (CC ₄ ) -alkoxyphenoxy, phenylthio, heterocyclyl, heterocylylthio, heterocyclyloxy, haloheterocyclyloxy, alkylheterocyclyloxy and alkoxyhetene, or alkoxyhetenoxy or alkoxyhetenoxy or alkoxyhetenoxy or alkoxyhetenoxy or alkoxyhetenoxy or alkoxy-heteroxy-allyl ester, or alkoxy-heteroxy-allyl ester or alkoxy-heteroxy-allyl ester, wherein Residues of one or more hydrogen atoms, in the case of fluorine also up to the maximum number by halogen, preferably chlorine or fluorine, can be replaced, where in the event that these substituents are (C ₁ -C ₄ ) alkyl, these are also cyclically linked can and in these condensed ring systems such as indane, di, tetra or decahydronaphthyl or benzocycloheptane system one or two aliphatic carbon units by heteroatom unit such as oxygen or sulfur can be replaced and one or more hydrogen atoms on the aliphatic carbon atom units, in the case of fluorine also up to the maximum number, can be replaced by halogen or (C ^ C ^ alkyl).

Furthermore, under the definition "that, in all of the alkyl, cycloalkyl, alkenyl or alkynyl groups mentioned in Q ¹ -Q ⁶ and groups derived therefrom, the hydrogen atoms are partly, in the case of fluorine, completely replaced by halogen atoms can be, and in all alkyl, alkenyl and alkynyl groups mentioned for Q ¹ - Q ⁶ up to three non-adjacent saturated carbon units replaced by oxygen or the groups S (O) _{01 2} or Si (CH ₃ ) ₂ could be"

for example to understand:

Haloalkyl groups, such as the fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 1, 1-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 3,3, 3-trifluoropropyl or the 1, 1, 1-trifluoroisopropyl group; Haloalkoxy groups, such as the difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy or the 2,2,2-trifluoroethoxy group; Haloalkenyl residues, such as the 1-fluoroethenyl, 2-fluoroethenyl, 1-fluoropropenyl, 2-

Fluoropropenyl or the 3,3,3-fluoropropenyl radical;

Halocycloalkyl radicals, such as the 2,2-dichlorocyclopropyl or the 2,2-

Difluorocyclopropyl residue;

Haloalkylthio residues, such as the trifluoromethylthio residue

Haloalkylsulfinyl residues, such as the trifluoromethylsulfinyl residue;

Haloalkylsulfonyl radicals, such as the trifluoromethylsulfonyl radical;

Alkoxyalkyl radicals, such as the methoxymethyl, ethoxymethyl, propoxymethyl,

Isopropoxymethyl, butoxymethyl, tert-butoxymethyl, methoxyethyl, ethoxyethyl,

Propoxyethyl, butoxyethyl or the butoxybutyl radical;

Alkoxyalkoxy radicals, such as the methoxyethoxy or the ethoxyethoxy radical;

Alkoxy-alkoxyalkyl radicals, such as the ethoxy-ethoxymethyl radical;

Alkoxyalkenyl radicals, such as the 3-methoxy-propenyl or the 3-ethoxypropenyl radical;

Alkoxy-alkynyl radicals, such as the 3-methoxypropynyl or the 3-ethoxypropynyl radical;

Alkoxy-haloalkyl groups such as the 1-methoxy-2,2,2-trifluoroethyl; 1-ethoxy-2,2,2-trifluoroethyl-, 1-propoxy-2,2,2-thfluoroethyl-, 2-methoxy-1,1,1-trifluoro-2-propyl-, 2-

Ethoxy-1, 1, 1-trif luor-2-propyl, 2-methoxy-1, 1-difluorethyl or the 2-methoxy-1 - fluoroethyl group,

Haloalkoxy-alkyl groups, such as the 2,2,2-trifluoroethoxymethyl or the

1, 1, 1, 3,3,3-hexafluoro-2-propoxy-methyl group,

Haloalkox-haloalkyl groups, such as the 2- (2,2,2-trifluoroethoxy) -1, 1,1-trifluoro-2-propyl group,

Aryloxy-haloalkyl groups, such as the 2-phenoxy-1,1,1-trifluoro-2-propyl group or the 2- (p-tolyloxy) -1,1,1 -trifluoro-2-propyl group Arylalkoxy haloalkyl

Groups such as the 2-benzyloxy-1, 1, 1-trifluoro-2-propyl or the

2- (4-methylbenzyloxy) -1,1,1-trifluoro-2-propyl group,

Trialkylsilylalkyl residues, such as the trimethylsilylmethyl, trimethylsilylethyl or the

Tri methy Isi ly I propy I rest.

The above explanations apply accordingly to homologs or their derived residues. The present invention relates to the compounds of formula (I) in the form of the free base or a salt, preferably an acid addition salt. Acids which can be used for salt formation are inorganic acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, trifluoroacetic acid, methanesulfonic acid , Benzenesulfonic acid, camphorsulfonic acid or toluenesulfonic acid.

In addition to the cis / trans isomerism mentioned on the cycloalkyl radicals and on the heteroaliphatic systems including the groups A and B, the compounds of the formula I in some cases have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur. The invention encompasses both the pure isomers and their mixtures. The mixtures of diasteromers can be prepared using conventional methods, e.g. by selective crystallization from suitable solvents or by chromatography, into which the components are separated. Racemates can be separated into the enantiomers by conventional methods, e.g. by salt formation with an enantiomer of a chiral acid, separation of the diastereomeric salts and release of the pure enantiomers by means of a base.

The invention further relates to a process for the preparation of compounds of the formula (I), which is characterized in that a compound of the formula

wherein R ¹ and R ^{2 have} the meanings given under formula I and L represents a leaving group, with a nucleophile of the formula (VI), HX-Q (VI) in which X and Q have the meanings given above under formula I, and further derivatize the compounds of the formula I obtained in this way or otherwise, optionally on the heterocycle or in the side chain Q, and the compounds of the formula thus obtained (I) optionally converted into their salts.

The substitution reaction described above is known in principle. The leaving group L can be varied within further limits and can mean, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine, or alkylthio, such as methyl or ethylthio, or alkanesulfonyloxy, such as methane, trifluoromethane or ethanesulfonyloxy, or arylsulfonyloxy, such as benzenesulfonyloxy or toluenesulfonyloxy , or alkylsulfonyl, such as methyl or ethylsulfonyl, or arylsulfonyl, such as phenyl or toluenesulfonyl, or alkoxy, such as methoxy, ethoxy, propoxy or isopropoxy or aryloxy, such as phenoxy or the trichloromethyl group.

The aforementioned reaction is carried out in a temperature range from 20 to 150 ° C. and, if the cleavage product HL has strongly acidic properties during the substitution, expediently in the presence of a base and optionally in an inert organic solvent, such as N, N-dimethylformamide, N, N -Dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. Mixtures of the solvents mentioned can also be used.

Suitable bases for the case where X is oxygen are, for example, alkali or alkaline earth metal carbonates, bicarbonates, amides or hydrides such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium amide or sodium hydride; if X is NH, these are, for example, Akali - or alkaline earth metal carbonates, bicarbonates, hydroxides, amides or hydrides such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, sodium amide or sodium hydride or organic bases such as triethylamine or pyridine. A second equivalent of an amine of the formula (VI) can also be used as an auxiliary base.

If X is oxygen, the nucleophiles of the formula (VI) required as starting products can be prepared by known processes, for example by reducing a keto group with a suitable reducing agent, for example a complex metal hydride or else with hydrogen and a hydrogenation catalyst. To produce the cis-cyclohexanols particularly the catalytic hydrogenation of appropriately substituted phenols or the reduction suitable cyclohexanone derivatives is substituted with complex hydrides bearing substituents with a large space-filling, such as L-Selectride ^®.

If X is NH, the nucleophiles of the formula (VI) required as starting products can be prepared by known processes, for example by reducing an oxime or azide with a suitable reducing agent, for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst Amination or Leuckart-Wallach reaction of a ketone or Gabriel reaction of an alkyl halide or tosylate. The reductive amination of appropriately substituted cyclohexanones with ammonium salts and sodium cyanoborohydride or with ammonia and hydrogen in the presence of metal catalysts such as nickel, ruthenium, rhodium or palladium is suitable for preparing the cyclohexylamines, the starting materials for the particularly preferred cis-cyclohexylamino derivatives this method the proportion of desired cis amine is particularly high. Another method is the hydrogenation of anilines or aromatic nitrate compounds in the presence of hydrogenation catalysts.

Further methods for the preparation of the nucleophiles of the formula (VI) for which Q is one of the particularly preferred 6-ring derivatives are described, for example, in DE-A-42 08 254, DE-A-43 31 178, DE-A-44 17 163, DE-A-44 36 509, DE-A-44 37 137, DE-A-195 23 906, DE-A-196 13 329 and DE- A-196 14 718.

The starting materials of the formula (V) are known or can be prepared analogously to known processes (see e.g. Helv. Chim. Acta SS, 1365 (1950); J. Amer. Chem. 78, 2447 (1956)).

The active ingredients are suitable for good plant tolerance and cheaper

Warmblood toxicity to control animal pests, in particular

Insects, arachnids, helminths and molluscs, very particularly preferred for

Control of insects and arachnids in agriculture, in the

Animal breeding, in forests, in the protection of stocks and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as all or individual stages of development. The pests mentioned above include:

From the order of the Acarina e.g. Acarus siro, Argas spp., Omithodoros spp.,

Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,

Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,

Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp ..

From the order of the Isopoda e.g. Oniscus asselus, Armadium vulgar, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spp ..

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana,

Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp.,

Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Isoptera, for example Reticulitermes spp .. From the order of the anoplura, for example Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp .. From the order of the Mallophaga, for example Trichodectes pp., Damalinea spp .. From the order of the Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci , Frankliniella spp ..

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp .. From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralosoniphususumi , Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp ..

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppia, Fpp., Phyllocnist spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonodanaulaanaanaanaanaanaanaapanaanaana, Cacoecia , Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysoumisumamusilumilisilamilisilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailusilnailysilnailysilnailysilnailysilnailysilnailysilceilysilnailysilnailysilysilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailysilnailisilamidosphalosusphysis. , Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Nipt hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptus spp ..

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp ..

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp. Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera e.g. Xenopsylla cheopsis, Ceratophyllus spp .. From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans. From the class of the helminths e.g. Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.

From the class of the Gastropoda e.g. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp ..

A Δuι isc d rieetrr KK "llaascsceo

z 7.B R. D πrreoiisβsceonnaα s cpnpn ..

The plant-parasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes, such as those of the genera Meloidogyne (root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera, or globodera or pallid nodules, cystic nodules, Heterodera trifolii) and the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus),

Tylenchulus (like Tylenchulus semipenetrans), Tylenchorhynchus (like Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (like Rotylenchus robustus), Heliocotylenchus (like Haliocotylenchus multicinctus), Belonoaimus (like Belonoaimus longicaudatus), Longidorus (like Longidorus elongatus), Trichodorus (like Trichodorus primitivus) and Xiphinema (like Xiphinema index).

The compounds of the invention can also be used to combat the nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes such as Anguina tritici).

The invention also relates to compositions, in particular insecticides and acaricidal compositions, which contain the compounds of the formula (I) in addition to suitable formulation auxiliaries.

The agents according to the invention generally contain from 1 to 95% by weight of the active compounds of the formulas (I).

They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. The following formulation options are therefore preferred:

Wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), mordants, granules in the form of , Spray, elevator and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual formulation types are known in principle and are described, for example, in:

Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker NY, 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:

Watkins, "Handbook of Insecticide Dust Diluents and Garriers," 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y .; Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1967; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced, e.g. in the form of a finished formulation or as a tank mix. Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. Examples of emulsifiers that can be used are: alkylarylsulfonic acid calcium salts such as cadodecylbenzene sulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.

The active ingredient concentration in wettable powders is generally about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active compound concentration can generally be about 5 to 80% by weight. Dust-like formulations generally contain 5 to 20% by weight of active ingredient, sprayable solutions about 2 to 20% by weight. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.

In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.

For use, the concentrates present in the commercial form are optionally diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and in some cases also in the case of microgranules, using water. Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use. The application rate required varies with the external conditions such as temperature, humidity and others. It can vary within wide limits, for example between 0.0005 and 10.0 kg / ha or more of active substance, but is preferably between 0.001 and 5 kg / ha.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.

The pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms, etc. Preferred mixing partners are

1. from the group of the phosphorus compounds acephate, azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophos-ethyl, Cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl , Demeton-S-methyl sulphone, Dialifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenithriothion, Fensulfothion, Fenthion, Fonophos, Formothion, Hepophos24) , Isozophos, Isothioate, Isoxathion, Malathion, Methacrifos, Methamidophos, Methidathion, Salithion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosfolan 301, Phosphoc Phosmet, Phosphamidon, Phoxim, Pirimiphos, Primiphos-ethyl, Pirimiphos-methyl, Profenofos, Propaphos, Proetamphos, Prothiofos, Pyraclofos, Pyridapenthion, Quinalphos, Sulprofos, Temephos, Terbufos, Tebupirimfos, Tetrachlorvinphos , Thiometone, triazophos, trichlorphone, vamidothione; 2. from the group of carbamates

Alanylcarb (OK-135), Aldicarb, 2-sec-Butylphenylmethylcarbamate (BPMC), Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Benfuracarb, Ethiofencarb, Furathiocarb, HCN-801, Isoprocarb, Methomyl, 5-Methyl-m-cumenylbutyryl carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717), triazamate;

3. from the group of carboxylic acid esters

Acrinathrin, allethrin, alphametrin, beta-cypermethrin, 5-benzyl-3-furylmethyl- (E) -, (1 R) -cis-2,2-di-methyl-3- (2-oxothiolan-3-ylidenemethyl) cyclopropanecarboxylate , Beta-Cyfluthrin, Beta-Cypermethrin, Bioallethrin, Bioallethrin (S) -cyclopentylisomer), Bioresmethrin, Biphenate, (RS) -1 -Cyano-1 - (6-phenoxy-2-pyridyl) methyl- (1 RS) - trans -3- (4-tert-butylphenyl) -2,2-dimethylcyclopropane decarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, Esfenvalerate, fenfluthrin, fenprohrate, fenproatehrin, fenpropatin . Fluvalinate (D-isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, pheothrin ((R-isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD , Tralomethrin, transfluthrin, zeta-cypermethrin (F-56701);

4. from the group of the amidines amitraz, chlorodime form;

5. from the group of tin compounds cyhexatin, fenbutatin oxide;

6. Other

Abamectin, ABG-9008; Acetamipirid, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, Bacillus thuringiensis, Beauveria bassianea, Bensultap, Bifenazate (D-2341), Binapacryl, BJL-932, Bromopropylate, BTG-504, BTG-505, Buprofezin Camphechlor, Cartap, Chlorobenzilate, Chlorfenapyr, Chlorfluazuron, 2- (4-Chlorophenyl) -4,5-diphenylthiophene (UBI-T 930), Chlorfentezine, Chromafenozide (ANS-118), CG-216, CG-217, CG-234 , A-184699, cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro12-0470), cyromazine, diacloden (thiamethoxam), diafenthiuron,

N- (3,5-dichloro-4- (1, 1, 2,3,3,3-hexafluoro-1-propyloxy) phenyl) carbamoyl) -2-chlorobenzcarboximidic acid ethyl ester, DDT, dicofol, difluobenzuron, N- (2, 3-dihydro-3-methyl-1, 3-thiazol-2-ylidene) -2,4-ylidene) -2,4-xylidene, dinobutone, dinocap, diofenolan, DPX-062, emamectin benzoate (MK-244) , Endosulfan, Ethiprole (Sulfethiprole), Ethofenprox, Etoxazole (YI-5301), Fenazaquin, Fenoxycarb, Fipronil, Flumite (Flufenzine, SZI-121), 2-Fluoro-5- (4- (4-ethoxyphenyl) -4-methyl -1- pentyl) diphenyl ether (MTI 800), granular and nuclear polyhedron viruses, fenpyroximate, fenthiocarb, flubenzimine, flucycloxuron, flufenoxuron, flufenprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenozide (RH-0345), halofen 732), Hexaflumuron (DE_473), Hexythiazox, HOI-9004, Hydramethylnon (AC 217300), Lufenuron, Imidacloprid, Indoxacarb (DPX-MP062), Kanemite (AKD-2023), M-020, MTI-446, Ivermectin, M- 020, methoxyfenozide (Intrepid, RH-2485), milbemectin, NC-196, Neemgard, Nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H- thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651),

2-Nitromethylene-1, 2-thiazinan-3-ylcarbamaldehyde (WL 108477), Pyriproxyfen (S-71639), NC-196, NC-111, NNI-9768, Novaluron (MCW-275), OK-9701, OK- 9601, OK-9602, Propargite, Pymethrozine, Pyridaben, Pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, Silafluofen, Silamadine (CG - 177), Spinosad, SU-9118, Tebufenozide, Tebufenpyrad (MK-239), Teflubenzuron, Tefuranitozine MTI-446), Tetradifon, Tetrasul, Thiacloprid, Thiocyclam, TI-435, Tolfenpyrad (OMI-88), Triazam 7988), Trifumuron, Verbutin, Vertalec, (Mycotal), YI-5301.

The active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight. The application takes place in a customary manner adapted to the application forms.

The active compounds of the formula (I) according to the invention are also suitable for combating endo- and ectoparasites in the veterinary field or in the field of animal husbandry.

The active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, dipping (dipping), spraying (spraying), pouring on (pour-on and spot) -on) and the pump and by parenteral use in the form of, for example, the injection.

The novel compounds of the formula (I) according to the invention can accordingly also be used particularly advantageously in livestock farming (e.g. cattle, sheep, pigs and poultry such as chickens, geese, etc.). In a preferred embodiment of the invention, the animals are given the new compounds, if appropriate in suitable formulations (see above) and if appropriate with the drinking water or feed orally. Since excretion in the faeces is effective, the development of insects in the faeces of the animals can be prevented very easily in this way. The appropriate dosages and formulations depend in particular on the type and stage of development of the livestock and also on the infestation pressure and can be easily determined and determined using the usual methods. The new compounds can e.g. in doses of 0.01 to 1 mg / kg body weight.

The compounds of formula (I) according to the invention are also distinguished by an excellent fungicidal action. Fungal pathogens that have already penetrated into the plant tissue can be successfully combated curatively. This is particularly important and beneficial in such fungal diseases, which can no longer be effectively combated after the infection has occurred with the usual fungicides. The spectrum of activity of the claimed compounds covers various economically important phytopathogenic fungi, such as Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaerea nodorum and Pellikularia sasakii and Puccinia recondita.

The compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking or as preservatives in drilling and cutting oils.

The active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.

Examples of fungicides known from the literature which can be combined according to the invention with the compounds of the formula I include the following products: aldimorph, andoprim, anilazines, azoxystrobin, azaconazole, BAS 450F, benalaxyl, benodanil, benomyl, bethoxazine, binapacryl, bion (CGA- 245704), bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, carpropamide, CGA 173506, cymoxanil, cyproconazole, cyprodinil, cyprofuram, diflumetorim, dichlorfluanid, dichlormezin, diclobutazolone, diclobutrazol, diclobutrazole, (CGA 169374), Difluconazole, Dimethirimol, Dimethomorph, Diniconazole, Dinocap, Dithianon, Dodemorph, Dodine, Edifenfos, Epoxidconazole, Ethirimol, Etridiazol, Famoxadone, (DPX-JE874), Fenarimol, Fenbuampidolipid, Fenbu , Fentin acetates, fentihydroxide, Ferimzone (TF 164), fluazinam, fluobenzimine, fludioxonil, flumetover (RPA-403397), fluquinconazole, fluorimide, flusilazole e, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetylaluminium, Fuberidazole, Furalaxyl, Furconazol, Furametpyr (S-82658), Furmecyclox, Guazatine, Hexaconazole, Imazalil, Imibenconazole, Ipconazole, Iprobefos, Iprodione, Isoprothiolane, KNF 317, Kresoxim-methyl (BAS-490F), copper compounds like Cu-oxychloride, Oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepapan KIFD 3535), Mepronil, Metalaxyl, Metalaxyl-M (CGA-329351), Metconazole, Methasulfocarb, Methfuroxam, Metominofen (SSF-126), Metominostrobin (Fenominostrobin, SSF-126), MON 24000, MON-6550, MON- 41100, Myclobutanil, Nabam, Nitrothalidopropyl, Nuarimol, Ofurace, OK-9601, OK- 9603, Oxadixyl, Oxycarboxin, Penconazol, Pencycuron, PP 969, Polyoxins, Probenazole, Propineb, Prochloraz, Procymidon, Propamocarb, Pyrocifen, Pyriconazol, Propiconazolox , Pyrimethanil, pyroquilone, quinoxyfen (DE-795), rabenzazole, RH-7592, RH-7281, sulfur, spiroxamines, SSF-109, tebuconazole, tetraconazole, TTF 167, thiabendazole, thicyofen, thifluzamide (RH-130753), thiofanate Thiram, TM-402, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadime nol, triazoxide, Trichoderma harzianum (DHF- 471), tricyclazole, tridemorph, triflumizole, triforine, triflumizole (UCC-A815), triticonazole, validamycin, vinchlozolin, XRD 563, zineb, sodium dodecyl sulfonate, dodecylsulfonate, C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropyl napthalene sulfonate, sodium methylenebisnaphthalenesulfonate, cetyl trimethyl ammonium chloride, salts of long-chain primary, secondary or tertiary amines, amines Lauryl-pyrimidinium bromide, ethoxylated quaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline.

The above-mentioned combination partners are known active ingredients, which are largely described in The Pesticide Manual (Editor: Clive Tomlin), 11th edition (1997), Crop Protection Publications / ISBN 1-901396-11-8 795. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges, the active substance concentration of the use forms can be from 0.0001 to 95% by weight of active substance, preferably between 1 and 50% by weight. The application takes place in a Application forms customary usual way.

The compounds of formula (I) can also be used to control harmful plants in crops of known or still to be developed genetically modified plants. The transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality, storability, composition and special ingredients. Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.

Preferred is the use in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.

When using in transgenic cultures, especially with insect resistance, in addition to the effects on harmful organisms that can be observed in other cultures, there are often effects that are specific to the application in the respective transgenic culture, for example an altered or specially expanded pest spectrum that can be controlled or changed application rates that can be used for the application.

The invention therefore also relates to the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.

On the content of German patent application 197 41 654.3, the priority of which This application claims, as well as the content of the enclosed summary, reference is hereby expressly made; by quotation they are part of this description.

The following examples serve to explain the invention, without this being restricted thereto.

A. Examples of formulation

a) A dusting agent is obtained by mixing 10 parts by weight of active ingredient and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.

b) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as the inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.

c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor ground to a fineness of less than 5 microns.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.

e) Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand. A suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately. The proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate. B. Production examples

Example A

4- (cis-4-tert-butyl-cyclohexylamino) -2-chloro-6-methyl-1, 3,5-triazine

3.3 g (20 mmol) of 2,4-dichloro-6-methyl-1,3,5-triazine (Helv. Chim. Acta SS, 1365 (1950) were placed in 75 ml of tetrahydrofuran and a solution of 3 , 1 g (20 mmol) of cis-4-tert-butyl-cyclohexylamine and 3.0 g (30 mmol) of triethylamine in a little tetrahydrofuran were added dropwise. The mixture was stirred for 6 hours at room temperature, concentrated and taken up in water / toluene. The toluene phase was stirred twice more with water, the organic phase was dried and concentrated and, for purification, chromatographed on silica gel with heptane / petroleum ether 3: 2, giving 3.8 g (52.8% of theory) of one yellow oil.

Example B

4- (cis-4-tert-butylcyclohexylamino) -2-methyl-1, 3,5-triazine 3.5 g (12.4 mmol) of 4- (cis-4-tert-butyl-cyclohexylamino) -2-chloro-6-methyl-1, 3,5-triazine (Example 1) was in 100 ml at room temperature hydrogenated in the presence of 1.2 g (15 mmol) of sodium acetate and 1 g of palladium / carbon (5%) at atmospheric pressure. After filtering off the catalyst, the mixture was concentrated, taken up in water / toluene, the toluene phase was stirred with aqueous sodium bicarbonate solution and the organic phase was dried and concentrated. For purification, it was chromatographed on silica gel. 1.5 g (48.3% of theory) of a colorless solid were obtained. Mp .: 72 to 73 ° C.

Example C

4- (cis-4-tert-butylcyclohexylamino) -2,6-dimethyl-1, 3,5-triazine

1.25 (5.5 mol) 2,6-dimethyl-4-trichloromethyl-1, 3,5-triazine (Bull. Chem. Soc. Jap. (1969), 2924) and 0.85 g (5.5 mol) cis-4-tert-butylcyclohexylamine were heated under reflux in 10 ml of tetrahydrofuran for 12 hours. The mixture was concentrated and the residue was chromatographed on silica gel (ethyl acetate / petroleum ether 4: 1). Yield: 1.1 g of yellow resin (76.2% of theory)

Further examples can be found in the tables. Table 1

Unless otherwise noted, the substituents on the cyclohexane assume the ice configuration.

Table 2

Table 3

Table 4

Table 5

Table 6

C. Biological examples

Use as an insecticide / acaricide / nematicide

Example A

Cut stems with a leaf of bean plants (Phaseolus vulgaris) are transferred to amber glass bottles filled with tap water and then covered with about 100 spider mites (Tetranychus urticae). The plant leaf and spider mites are then immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, plants and animals are stored in a climatic chamber (16 hours light / day, 25 ° C, 40 to 60 ° C RH). After 6 days of storage, the effect of the preparation on all stages of the spider mite is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example Nos. 9, 18, 23, 45, 46, 49, 50, 52, 53, 82 and 83 cause 90 to 100% mortality.

Example B

A petri dish, the bottom of which is covered with filter paper and contains about 5 ml of nutrient medium, is prepared. Five L2 larvae of the Egyptian cottonworm (Spodoptera litoralis) are counted in a small cup. 200 μl of an aqueous solution of the preparation to be tested and formulated is pipetted into the beaker. The traded larvae are then poured into the petri dish and a further 200 μl of the aqueous solution are distributed over the nutrient medium. After closing the Petri dish, it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the effect of the preparation on the larvae is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparation according to Example Nos. 37, 45 and 52 cause 90 to 100% mortality of the larvae. Example C

A petri dish, the bottom of which is lined with filter paper and contains about 5 ml of nutrient medium, is prepared. Pieces of filter paper with approximately 30, 24-hour-old eggs of the American tobacco bud owl (Heliothis virescens) are immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds and then placed in the petri dish. A further 200 μl of the aqueous solution are distributed over the nutrient medium. After closing the Petri dish, it is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the effect of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example Nos. 9, 13, 24, 37, 38, 45, 49, 50, 53, 82, 306 and 307 bring about a 90 to 100% strength Mortality.

Example D

Germinated field bean seeds (Vicia faba) with germ roots are transferred to amber glass bottles filled with tap water and then coated with approx. 100 black bean aphids (Aphis fabae). Plants and aphids are then immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, plants and animals are stored in a climatic chamber (16 hours light / day, 25 ° C, 40 to 60% RH). After 3 and 6 days of storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example Nos. 9, 13, 24, 37, 45, 52, 53 and 82 cause 90 to 100% mortality of the aphids. Example E

The leaves of 12 rice plants with a stem length of 8 cm are immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, the rice plants treated in this way are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the leafhopper species Nilaparvata lugens. After closing the petri dish, it is stored in a climatic chamber (16 hours light / day, 25 ° C, 40 to 60% RH). After 6 days of storage, the mortality of the leafhopper larvae is determined. At a concentration of 300 ppm (based on the active ingredient content), the preparation according to Example Nos. 9, 23, 37, 50, 52, 53, 82 and 83 causes 90 to 100% mortality.

Example F

A Petri dish is prepared, half of which is covered with filter paper and contains a germinated grain of corn on a damp cotton swab. About 50, 4-5 day old eggs of the corn rootworm (Diabrotica undecimpunctata) are transferred to the filter paper. Three drops of 200 μl of an aqueous solution of the preparation to be tested and formulated are pipetted onto the eggs and the rest onto the corn kernel. After closing the Petri dish, this is stored in a climate chamber at approx. 25 ° C. After 6 days of storage, the mortality of the preparation on the eggs and any larvae hatched from them is determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Example Nos. 9, 13, 24, 37, 38, 49, 50, 52 and 53 cause 90 to 100% mortality. Use as an anti-parasitic

Example G

In vitro test on tropical cattle ticks (Boophilus microplus)

The effectiveness of the compounds according to the invention against ticks was demonstrated in the following experimental setup:

To prepare a suitable active substance preparation, the active substances were dissolved in 10% (w / v) in a mixture consisting of dimethylformamide (85 g), nonylphenol polyglycol ether (3 g) and oxyethylated castor oil (7 g), and the emulsion concentrates thus obtained were dissolved in water diluted a test concentration of 1000 ppm. Ten fully sucked females of the tropical tick, Boophilus microplus, were immersed in this active ingredient dilution for five minutes. The ticks were then dried on filter paper and then for the purpose of laying eggs with the back on an adhesive film. The ticks were stored in a warming cabinet at 28 ° C and a humidity of 90%.

As a control, female ticks were only immersed in water. The inhibition of oviposition was used two weeks after treatment to evaluate the effectiveness.

In this test, the compounds according to Examples Nos. 9, 11, 13, 14, 45, 52 and 82 each cause 100% inhibition of egg laying.

Use as a fungicide

The compounds were tested for activity against one or more of the following organisms: Plasmopora graminis f. sp. tritici Pyricularia oryzae Leptosphaeria nodorum Phytophthora infestans

Aqueous solutions or dispersions of the compounds in the desired concentration with the addition of a wetting agent were applied to leaves or stems of the test plant. The plants or parts of plants were inoculated with the respective test pathogen and kept under controlled environmental conditions which are suitable for plant growth and the development of the disease. After a suitable time, the degree of infection of the infested plant was assessed visually. The compounds are rated on a scale from 1 to 3, in which 1 means no to little control, 2 medium control and 3 good to complete. At a concentration of 500 ppm or less, the following compounds were rated 2 or higher against the listed fungi.

Example H

Effect against Erysiphe graminis f. sp. tritici (wheat mildew)

The following compounds were rated 2 or higher: Example Nos .: 50 and 53

Example I

Action against Plasmopora viticola (downy mildew)

The following compounds were rated 2 or higher: Example No .: 8, 9,

18, 45, 46 and 52

Example J

Action against Pyricularia oryzae

The following compounds were rated 2 or higher: Example No.

45, 46, 49, 50, 52 and 84 Example K

Effect against Leptosphaeria nodorum

The following compounds were rated 2 or higher: Example No .:

50, 51 and 52

Example L

Effect against Phytophthora infestans

The following compounds were rated 2 or higher.

Examples Nos. 9, 45, 50, 52 and 53.

Claims

claims

1. Substituted 1, 3,5-triazines of the general formula (I), their N-oxides and / or salts

in which

R ¹ and R ^{2 are} identical or different and are each hydrogen, {CC ₆ ) -A \ y \, (C ₃ -C ₆ ) -cycloalkyl, (C ^ C _ß J-haloalkyl, (C ₃ -C ₆ ) - Halogencycloalkyl, halogen, (C ₁ -C ₄ alkoxy - C ₁ -C ₄ alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl or (C ₁ -C ₄ ) cyanoalkyl;

X represents oxygen or NH;

Q represents a radical of the general formula Q ¹ , Q ² , Q ³ , Q ⁴ , Q ⁵ or Q ⁶ ;

wherein the carbocycle is saturated or monounsaturated; n represents an integer from 2 to 7; R ³ and R ^{4 are the} same or different and are hydrogen or methyl and R ^{5 is} hydrogen, (C _r C ₂₀ ) alkyl, (C ₁ -C ₂₀ ) haloalkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ - C ₂₀ ) alkynyl, (C ^ C ^ hydroxyalkyl , (C _r C ₂₀ ) cyanoalkyl, (C _r C _M ) nitroalkyl, (C ^ CaoJ thiocyanalkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₈ ) cycloalkenyl, (C ₃ - C ₈ ) - Cycloalkyl- (C _r C ₄ ) -alkyl, (C _r C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₂₀ ) -alkoxy, (C _r C ₂₀ ) -Alkoxyalky, (C ₃ -C ₈ ) -cycloalkoxy, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy, (C ₃ - C ₈ ) -cycloalkoxy- (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₈ ) -cycloalkyl- (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₂₀ ) -alkylthio, (C ₃ -C ₈ ) cycloalkylthio, (C ₁ -C ₂₀₎ alkylsulfinyl, _(C1-C20) - alkylsulfonyl, (C ₁ -C ₈₎ alkoxy haloalkoxy (C ₁ -C _4), (C ^ C _β J- Haloalkoxy- (C _r C ₄ ) -alkyl, (CC ^ -haloalkoxy ^ CC ^ -haloalkyl, (C _r C ₈ ) -alkylthio- (CC ^ -alkyl, (C ₃ -C ₈ ) -cycloalkylthio- (C ₁ -C ₄ ) alkyl, (C ₃ -C ₈ ) cycloalkyl- (C _r C ₄ ) alkylthio- (C _r C ₄ ) alkyl, tri- (C _r C ₈ ) alkylsilyl, di- (C _r C ₈ ) alkyl- (C ₃ -C ₈ ) cycloalkylsily , Di ^ C ^ C ^ -alkylphenyl ^ C ^ C -alkylsilyl, dimethyl- [mono-, di- or tris-oxa- (C ₁ -C ₁₂ ) -alkyl] -silyl, [(CC ^ - Alkyldimethylsilyl] - (C _r C ₈ ) -alkyl, dimethylphenylsilyl, a group of the formula (II)

(II)

Halogen, cyano, thiocyano, nitro, aryl, AryKC ^ C ^ alkyl, aryl- (C ₂ -C ₄ ) alkenyl, aryl- (C ₂ -C ₄ ) alkynyl, heteroaryl, heteroaryl- (C _r C ₄ ) -alkyl, aryloxy, heteroaryloxy, aryl- (C ₁ -C ₄ ) -alkoxy, heteroaryl- (C ₁ -C ₄ ) -alkoxy, arylthio, heteroarylthio, aryl- (C _r C ₄ ) -alkylthio, heteroaryl- ( CC ₄ ) -alkylthio, aryloxy- (C _r C ₄ ) -alkyl, aryl- (C _r C ₄ ) -alkoxy- (C _r C ₄ ) -alkyl, heteroaryloxy- (C _r C ₄ ) -alkyl, heteroaryl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) alkyl, arylthio- (C _r C ₄ ) alkyl, aryl ^ C _! ^) - alkylthio- (C _r C ₄ ) -alkyl, heteroarylthio- (C _r C ₄ ) -alkyl, heteroaryKC _! - ^) - alkylthio- (C _r C ₄ ) alkyl, -CO-R ⁶ , COOR ⁶ or CONR ^ R ⁷ ; R ⁶ , R ^{6 '} , R ^{7 are the} same or different and are hydrogen, (C _r C ₂ o) -alkyl,

(C _r C ₂ o) haloalkyl, (C ₃ -C ₈ ) cycloalkenyl, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₈ ) - CycloalkyHCrC ^ alkyl, (C ₂ -C ₂₀ ) alkenyl, (C ₂ -C ₂₀ ) alkynyl, aryl, aryl- (C _r C ₄ ) alkyl, aryl- (C ₂ -C ₄ ) alkenyl, Aryl- (C ₂ -C ₄ ) -alkynyl, heteroaryl, heteroaryl- (C _r C ₄ ) -alkyl; or R ^{6 '} and R ⁷ together form a ring system of the formula (III) or (IV),

wherein

D is saturated or aromatic; m is an integer from 2 to 7; q and r are the same or different and are integers between 0 and 4, the sum of which gives a number from 2 to 4 and in (III) optionally a -

CH ₂ unit is replaced by oxygen, sulfur or a grouping NR ⁹ , R ⁸ and R ^{9 are} identical or different and are hydrogen, (C ₁ -C ₂₀ ) -alkyl,

(C _r C ₂₀ ) haloalkyl, (C ₃ -C ₈ ) cycloalkyl, (C _r C ₂ o) alkoxy, (C _r C ₂₀ ) alkylthio,

Pheny C ^ C ^ alkyl or phenyl, being for all radicals

R ³ , R ⁴ and R ^{5 must} not simultaneously be hydrogen;

Q ²

means;

R ^{4 has} the meanings given above; a group = CHR ¹⁰ , = NOR ¹⁰ , or

wherein

R ^{10 has} the meanings given above for R ⁶ and

U is a direct bond or the group -CH ₂ O-;

Q ³

(Q) means

wherein

R ^{4 has} the meanings given above,

V is a direct bond, oxygen, S (O) _{0ι1) 2} , OSO ₂ or SO ₂ O or VR ^{11 is} a group OC (= O) NR ⁸ R ^{8 "} and R ^6" , R ^{8 "} and R ^{11 are} the R ⁸ have the meanings indicated, and where in the aromatic part of the condensed ring system from Q ³ up to three, in the case of fluorine, all hydrogen atoms can be replaced by identical or different substituents;

Q ⁴

(Q ⁴ ) means

wherein

R) 4 ^{4 has} the meanings given above,

A is a direct bond, oxygen or sulfur, B represents CH ₂ , oxygen or sulfur, where in Q ⁴ at least one of the units A or B is oxygen or

Must be sulfur, R ^{12 has} the meanings given above for R ⁸ ;

Q ⁵

HN - R> 3 (operated,

R ^{13 represents} aryl, heteroaryl, -CO-OR ¹⁴ , -CS-OR ¹⁴ or -CS-SR ¹⁴ ; R ¹⁴ (CrC ^ alkyl, (CrC ^ haloalkyl, aryl- (C _r C ₄ ) alkyl, aryl or

Heteroaryl means; where in all compounds of the formula (II) phenyl, aryl and heteroaryl radicals can be unsubstituted or substituted with up to three, in the case of fluorine as a substituent also up to the maximum number, further radicals, and in all alkyls mentioned as Q ¹ - Q ⁸ -, Cycloalkyl, alkenyl or alkynyl groups and all groups derived therefrom which hydrogen atoms can partly, in the case of fluorine also completely, be replaced by halogen atoms, and in all of the alkyl, alkenyl and alkynyl groups mentioned for Q ¹ - Q ⁶ -Groups of up to three non-adjacent saturated carbon units can be replaced by oxygen or the grouping S (O) _{01 2} or Si (CH ₃ ) ₂ .

2. Substituted 1, 3,5-triazines of the general formula (I) according to claim 1, in which

R ^{1 represents} hydrogen or methyl; R ^{2 is} (C _r C ₄ ) alkyl, (C ^ C ^ haloalkyl or (C ^ C ^ alkoxyalkyl, and X is NH.

3. Substituted 1, 3,5-triazines of the general formula (I) according to Claim 1 or 2, in which

R ^{1 represents} hydrogen or methyl;

R ^{2 is} methyl, ethyl, propyl or isopropyl, and

X means NH.

4. Substituted 1, 3,5-triazines of the general formula (I) according to any one of claims 1 to 3, in which

R ^{1 represents} hydrogen or methyl;

R ^{2 represents} methyl, ethyl, propyl or isopropyl;

R ³ and R ^{4 are} hydrogen;

X represents NH;

Q represents a radical of the general formula Q ¹ in which the carbocycle is saturated; n represents the integer 5;

R ⁵ occupies position 4 on the cyclohexyl;

R ⁵ ((VC ^ alkyl, (C CJJ haloalkyl, (C ₃ -C ₆ ) cycloalkyl, methyl (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl, (CC _j -alkoxy, tri- (C ₁ -C ₅ ) alkylsilyl, di- (C ₁ -C ₅ ) alkyl- (C ₃ -C ₆ ) -cycloalkylsilyl, dimethyl- [mono-, di-, or tris-oxa- (C ₁ -C ₁₂ ) -alkyl] -silyl, [(C ₁ -C ₅ ) -alkyldimethylsilyl] - (C _r C ₅ ) alkyl, a group of the formula (II),

Aryl, aryl- (C ₁ -C ₄ ) -alkyl, aryloxy - ^ - C ^ -alkyl, aryl- (C ₁ -C ₄ ) alkoxy- (C ₁ -C ₄ ) -alkyl, the aryl listed above - or heteroaryl radicals and the radicals derived therefrom can be unsubstituted or can be provided with up to three, in the case of fluorine also up to the maximum number of identical or different radicals, -CO-R ⁸ , -CO-OR ⁸ , -CO-NR ^{6 '} R ⁷ ;

R ⁶ , R ^{6 '} , R ^{7 are the} same or different and are hydrogen, (C ^ C ^ alkyl or

Are aryl or R ⁸ and R ^{7 form} a ring system of the formula III or a tetrahydroisoquinoline system, m is an integer of 4 or 5;

R ^{8 is} hydrogen, (C 1 -C 6 -alkyl, benzyl or phenyl and the phenyl groups may be unsubstituted or may be provided with up to three, in the case of fluorine also up to the maximum number of identical or different radicals; and the above for R ⁸ , R ⁶ , R ⁶ , R ⁷ and R ⁸ listed phenyl, aryl or heteroaryl radicals and the radicals derived therefrom may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of identical or different radicals and in all compounds of the formula I in which Q is a cyclohexyl radical and in which the radical R ⁵ occupies the 4-position with respect to the pyrimidinyl-amino radical, the cis configuration of these substituents is preferred and, unless more precisely already described above defined, in all alkyl, cycloalkyl, alkenyl or alkynyl groups mentioned for Q and all groups derived therefrom, the hydrogen atoms can be partially, in the case of fluorine, completely replaced by halogen atoms, and - unless already defined in more detail above - in all alkyl, alkenyl and alkynyl groups mentioned for Q up to three non-adjacent saturated carbon atoms -Units can be replaced by oxygen or the grouping S (O) _01ι2 or Si (CH ₃ ) ₂ and their salts.

5. Substituted 1, 3,5-triazines of the general formula (I) according to one of the

Claims 1 to 4, in which

Q represents a radical of the general formula Q ¹ , in which

R ^{4 represents} hydrogen;

R ⁵ (CVCβJ-alkyl, (C ^ C ^ -haloalkyl, (C ₃ -C ₆ ) cycloalkyl, methyl (C ₃ -C ₈ ) cycloalkyl,

(C ₁ -C ₈ alkoxy, (C ₁ -C ₈ ) alkoxy- (C ₁ -C ₄ ) alkyl, tri- (C _r C ₅ ) alkylsilyl, preferably

Dimethy C ^ CsJ-alkylsilyl, dimethyl- [mono-, di- or tris-oxa- (C ₁ -C ₁₂ ) alkyl] -silyl, a group of the formula (II)

Aryl, aryl- (C ₁ -C ₄ ) -alkyl, aryloxy- (C ₁ -C ₄ ) -alkyl, the aryl or heteroaryl radicals listed above and the radicals derived therefrom unsubstituted or with up to three, in the case of fluorine can also be provided up to the maximum number of identical or different radicals, or their salts.

6. Substituted 1, 3,5-triazines of the general formula (I) according to one of claims 1 to 5, in which the hydrogen atoms of the alkyl and cycloalkyl groups mentioned for Q and all of the groups derived therefrom are partially, in the case of fluorine also completely, are replaced by halogen atoms and in all the alkyl groups mentioned for Q up to three non-adjacent saturated carbon units are replaced by oxygen or the group Si (CH ₃ ) ₂ .

7. A process for the preparation of substituted 1, 3,5-triazines of the general formula I according to one of claims 1 to 6, characterized in that a compound of the formula (V),

wherein R ¹ and R ^{2 have} the meanings given under formula I and L represents a leaving group with a nucleophile of the formula VI

HX-Q (VI) in which X and Q have the meanings given above under formula I, and further derivatize the compounds of the formula I obtained in this way or in some other way, if appropriate on the heterocycle or in the side chain Q and the compounds thus obtained Formula (I) optionally converted into its salts.

8. Agent containing an effective amount of at least one substituted

1, 3,5-triazine of the general formula (I) according to one of claims 1 to 6 and at least one conventional formulation agent.

9. Fungicidal composition according to claim 8, containing customary auxiliaries and additives for this application.

10. Insecticidal, acaricidal or nematicidal composition according to claim 8, containing auxiliaries and additives customary for these applications.

11. Plant protection agents containing at least one compound of the general formula (I) and at least one further active ingredient from the group fungicides, insecticides, acaracides, nematicides, herbicides, Plant growth regulators, sterilants and attractants together with the auxiliaries and additives customary for these applications.

12. Agents for use in wood preservation or as preservatives in sealants, in paints, in cooling lubricants for metalworking or in drilling and cutting oils, containing an effective amount of at least one substituted 1,3,5-triazine of the general formula (I) according to one of claims 1 to 6 together with the auxiliaries and additives customary for this application.

13. Substituted 1, 3,5-triazines according to any one of claims 1 to 6 for use as veterinary medicinal products, preferably for combating endo- and ectoparasites.

14. A process for the preparation of an agent according to any one of claims 8 to 12, characterized in that one or more active ingredients and the further auxiliaries and additives are mixed and converted into a suitable form of use.

15. Use of a substituted 1, 3,5-triazine of the general formula (I) according to one of claims 1 to 6 or agent according to one of claims 8, 9, 11 and 12 for combating phytopathogenic fungi.

16. Use of a substituted 1,3,5-triazine of the general formula (I) according to one of claims 1 to 6 or agent according to one of claims 8, 10, 11 and 12 for controlling insects, acarina and nematodes.

17. Use of a substituted 1,3,5-triazine of the general formula (I) according to one of Claims 1 to 6 or agent according to one of Claims 8, 9 and 12 as a wood preservative or as a preservative in sealants, in paints, in cooling lubricants for metalworking or in drilling and cutting oils.

18. A method of combating phytopathogenic fungi, characterized in that a fungicidally effective amount of a substituted 1,3,5-triazine of the general formula (I) according to one of these or the plants, areas or substrates attacked by them or on seeds of claims 1 to 6 or an agent according to one of claims 8, 9, 11 and 12 applied.

19. A method for controlling insect pests, acarina and nematodes, characterized in that an effective amount of a substituted 1,3,5-triazine of the general formula (I) according to one of the Claims 1 to 6 or an agent according to one of claims 8, 10, 11 and 12 applied.

20. Seed, treated or coated with an effective amount of a substituted 1,3,5-triazine of the general formula (I) according to one of claims 1 to 6 or an agent according to one of claims 8, 9, 11 and 12.