Insecticidally active nitro compounds

Claim 2

1) Nitro compounds of the formula (I) wherein R¹ and R² are hydrogen or C₁₋₄ alkyl, R³ is -S-R⁴ or in which R⁴ is C₁₋₄ alkyl, R⁵ and R⁶ are hydrogen or C₁₋₄ alkyl, Y is CH or N, and Z is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halogen or C₁₋₄ alkyl, provided that when Y is CH, then R¹ is C₁₋₄ alkyl.

Claim 3

2)Nitro compounds of the formula (I) according to claim 1 wherein R¹ and R² are hydrogen or methyl, R³ is -S-R⁴ or in which R⁴ is methyl, R⁵ and R⁶ are hydrogen or methyl, Y is CH or N, and Z is 3-pyridyl, 4-pyridyl or 5-thiazolyl which may be substituted by chlorine or methyl, provided that where Y is CH, then R¹ is methyl.

Claim 4

3) Compounds of the formula (I) according to claim 1 wherein R¹ and R² are hydrogen or methyl, R³ is in which R⁵ and R⁶ are hydrogen or methyl, Y is CH or N, and Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl, provided that when Y is CH, then R¹ is methyl.

Claim 5

4) Compounds of the formula (I) according to claim 1 wherein R¹ and R² are hydrogen or methyl,, R³ is in which R⁵ and R⁶ are hydrogen or methyl, Y is CH or N, and Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl, provided that where Y is CH, then R¹ is methyl, or where R² is hydrogen and R³ is in which either R⁵ or R⁶ is hydrogen, the other is methyl, then Y is N.

Claim 6

5) Compounds of the formula (I) according to claim 1 wherein R¹ and R² are hydrogen or methyl, R³ is in which R⁵ and R⁶ are hydrogen or methyl,, Y is N, and Z is 2-chloro-5-pyridyl.

Claim 7

6) Compounds of the formula (I) according to claim 1 having the following individual structures: 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine represented by the following formula 3-(2-chloro-5-pyridylmethyl)-1,1-dimethyl-2-nitroguanidine represented by the following formula 3-(2-chloro-5-pyridylmethyl)-1,3-dimethyl-2-nitroguanidine represented by the following formula 3-(2-chloro-5-pyridylmethyl)-1,1,3-trimethyl-2-nitroguanidine represented by the following formula 3-(2-chloro-5-pyridylmethyl)-3-methyl-2-nitroguanidine represented by the following formula 1-[1-(2-chloro-5-pyridyl)ethylamino]-1-dimethylamino-2-nitroethylene represented by the following formula 1-amino-1-[1-(2-chloro-5-pyridyl)ethylamino]-2-nitroethylene represented by the following formula 1-[1-(2-chloro-5-pyridyl)ethylamino]-1-methylamino-2-nitroethylene represented by the following formula 1-{N-[1-(2-chloro-5-pyridyl)ethyl]-N-methylamino}-1-dimethylamino-2-­nitroethylene represented by the following formula 3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine represented by the following formula

Claim 8

7) Process for the preparation of nitro compounds of the formula (I) wherein R¹ and R² are hydrogen or C₁₋₄ alkyl, R³ is -S-R⁴ or in which R⁴ is C₁₋₄ alkyl, R⁵ and R⁶ are hydrogen or C₁₋₄ alkyl,, Y is CH or N, and Z is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halogen or C₁₋₄ alkyl, provided that when Y is CH, then R¹ is C₁₋₄ alkyl. characterized in that a): (in the case where R³ is -S-R⁴ and Y is CH, then R¹ is replaced by R⁷, in which R⁷ is C₁₋₄ alkyl) compounds of the formula (II) wherein R⁴ has the same meaning as mentioned above, are reacted with compounds of the formula (III) wherein R⁷, R² and Z have the same meanings as mentioned above, in the presence of inert solvents, b): (in the case where R³ is and Y is CH, then R¹ is replaced by R⁷ compounds of the formula (Ia) wherein R⁷, R², R⁴ and Z have the same meanings as mentioned above, are reacted with compounds of the formula (IV) wherein R⁵ and R⁶ have the same meanings as mentioned above, in the presence of inert solvents, or c): (in the case where R³ is -S-R⁴ and Y is N) compounds of the formula (V) wherein R² and R⁴ have the same meanings as mentioned above, are reacted with compounds of the formula (VI) wherein R¹ and Z have the same meanings as mentioned above, and Hal represents halogen atom, in the presence of inert solvents, and if appropriate in the presence of acid binders, d): (in the case where R³ is and Y is N) compounds of the formula (Ic) wherein R¹, R², R⁴ and Z have the same meanings as mentioned above, are reacted with the above compounds of the formula (IV), in the presence of inert solvents.

Claim 9

7) Process for the preparation of nitro compounds of the formula (I) wherein R¹ and R² are hydrogen or C₁₋₄ alkyl, R³ is -S-R⁴ or in which R⁴ is C₁₋₄ alkyl, R⁵ and R⁶ are hydrogen or C₁₋₄ alkyl,, Y is CH or N, and Z is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halogen or C₁₋₄ alkyl, provided that when Y is CH, then R¹ is C₁₋₄ alkyl. characterized in that a): (in the case where R³ is -S-R⁴ and Y is CH, then R¹ is replaced by R⁷, in which R⁷ is C₁₋₄ alkyl) compounds of the formula (II) wherein R⁴ has the same meaning as mentioned above, are reacted with compounds of the formula (III) wherein R⁷, R² and Z have the same meanings as mentioned above, in the presence of inert solvents, b): (in the case where R³ is and Y is CH, then R¹ is replaced by R⁷ compounds of the formula (Ia) wherein R⁷, R², R⁴ and Z have the same meanings as mentioned above, are reacted with compounds of the formula (IV) wherein R⁵ and R⁶ have the same meanings as mentioned above, in the presence of inert solvents, or c): (in the case where R³ is -S-R⁴ and Y is N) compounds of the formula (V) wherein R² and R⁴ have the same meanings as mentioned above, are reacted with compounds of the formula (VI) wherein R¹ and Z have the same meanings as mentioned above, and Hal represents halogen atom, in the presence of inert solvents, and if appropriate in the presence of acid binders, d): (in the case where R³ is and Y is N) compounds of the formula (Ic) wherein R¹, R², R⁴ and Z have the same meanings as mentioned above, are reacted with the above compounds of the formula (IV), in the presence of inert solvents.

Claim 10

8) Insecticidal compositions, characterised in that they contain at least one nitro compound of the formula (I).

Claim 11

8) Insecticidal compositions, characterised in that they contain at least one nitro compound of the formula (I).

Claim 12

9) Process for combating harmful insects, characterised in that nitro compounds of the formula (I) are allowed to act on harmful insects and/or their habitat.

Claim 13

9) Process for combating harmful insects, characterised in that nitro compounds of the formula (I) are allowed to act on harmful insects and/or their habitat.

Claim 14

10) Use of nitro compounds of the formula (I) for combating harmful insects.

Claim 15

10) Use of nitro compounds of the formula (I) for combating harmful insects.

Claim 16

11) Process for the preparation of insecticidal compositions, characterised in that nitro compounds of the formula (I) are mixed with extenders and/or surface-active agents.

Claim 17

11) Process for the preparation of insecticidal compositions, characterised in that nitro compounds of the formula (I) are mixed with extenders and/or surface-active agents.