6-Halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests
The present invention relates to a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one 6-halogeno[1,2,4]triazolo[1,5-a]-pyrimidine of the general formula (I), wherein X, R 1 , R 2 , R 3 and R 4 are as defined in claim 1 and/or the agriculturally useful salts thereof.
1. A method of combating insects which comprises contacting the insects, their habitat, breeding ground, food supply, plant, seed, soil, area, material or environment in which the insects are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from insect attack or infestation with a insecticidally effective amount of at least one 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I
wherein
X is halogen;
R 1 is hydrogen;
R 2 is C 1 -C 10 -alkyl or C 1 -C 2 -fluoralkyl;
R 3 is hydrogen; and
R 4 is C 3 -C 8 -cycloalkyl, phenyl, or phenyl-C1-C4-alkyl wherein each phenyl and C 3 -C 8 -cycloalkyl may be unsubstituted or may carry one or two radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkyl, C 1 -C 10 -haloalkoxy, amino, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and halogen,
it being also possible for C 3 -C 10 -cycloalkyl and phenyl groups to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C 1 -C 4 -alkyl;
and/or at least one agriculturally acceptable salt thereof, thereby combating insects.
2. The method as claimed in claim 1 , wherein the radical R 2 in formula I is C 1 -C 4 -alkyl or C 1 -C 2 -fluoralkyl.
3. The method as claimed in claim 2 , wherein the radical R 2 in formula I is C 1 -C 2 -alkyl or C 1 -C 2 -fluoroalkyl.
4. The method as claimed in claim 1 , wherein the radical R 4 in formula I is cyclohexyl which carries a substituent in the 4-position.
5. The method as claimed in claim 4 , wherein the substituent is C 1 -C 4 -alkyl.
6. The method as claimed in claim 1 , wherein the radical R 4 in formula I is 1-phenylethyl which carries a substituent in the 4-position.
7. The method as claimed in claim 6 , wherein the substituent is selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy.
8. A method for protecting crops-from attack or infestation by insects which comprises contacting the crops with a insecticidally effective amount of a 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I
wherein
X is halogen;
R 1 is hydrogen;
R 2 is C 1 -C 10 -alkyl or C 1 -C 2 -fluoroalkyl;
R 3 is hydrogen; and
R 4 is C 3 -C 8 -cycloalkyl, phenyl, or phenyl-C1-C4-alkyl, wherein each phenyl and C 3 -C 8 -cycloalkyl may be unsubstituted or carry one or two radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkyl, C 1 -C 10 -haloalkoxy, amino, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and halogen,
it being also possible for C 3 -C 10 -cycloalkyl and phenyl groups to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C 1 -C 4 -alkyl;
and/or at least one salt thereof, thereby protecting crops.
9. The method as claimed in claim 1 , wherein the radical R 4 in formula I is phenyl, phenyl-C 1 -C 4 -alkyl or C 3 -C 8 -cycloalkyl, wherein each phenyl and C 3 -C 8 -cycloalkyl group may be unsubstituted or may carry one or two substituents which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkyl, C 1 -C 10 -haloalkoxy, amino, C 1 -C 10 -alkylamino, di(C 1 -C 10 -alkyl)amino, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkoxy and phenyloxy.
10. The method as claimed in claim 9 , wherein the radical R 4 in formula I is cyclohexyl which carries a substituent in the 4-position, the substituent being C 1 -C 4 -alkyl.
11. The method as claimed in claim 9 , wherein the radical R 4 in formula I is 1-phenylethyl which carries a substituent in the 4-position, wherein the substituent is selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy.