Insecticidally active nitro guanidine compounds

Abstract

Insecticidal novel nitro compounds of the formula 4 alkyl, R3 is -S-R4 or <IMAGE> 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 where Y is CH, then R1 is C1-4 alkyl.

We claim: 
     
       1. A . .novel.!. nitro compound of the formula ##STR38## wherein R 1  and R 2  are hydrogen or C 1-4  alkyl, R 3  is --S--R 4  or ##STR39## R 4  is C 1-4  alkyl, R 5  and R 6  are hydrogen or C 1-4  alkyl, and   Z is . .pyridyl,.!. thiazolyl, thiadiazolyl, pyrimidinyl, or isoxazolyl which may be substituted by halogen or C 1-4  -alkyl.   
     
     
       2. A compound according to claim 1, wherein   R 1  and R 2  are hydrogen or methyl,   R 3  is --S--R 4  or ##STR40## R 4  is methyl, R 5  and R 6  are hydrogen or methyl, and   Z is . .pyridyl,.!. thiazolyl, thiadiazolyl, pyrimidinyl, or isoxazolyl which may be substituted by chlorine or methyl.   
     
     
       3. A compound according to claim 1, wherein   R 1  and R 2  are hydrogen or methyl,   R 3  is ##STR41##  in which R 5  and R 6  are hydrogen or methyl, and Z is . .2-chloro-5-pyridyl or.!. 2-chloro-5-thiazolyl.   
     
     
       4. A compound according to claim 1, wherein R 1  and R 2  are hydrogen or methyl,   R 3  is ##STR42##  in which R 5  and R 6  are hydrogen or methyl, and Z is . .2-chloro-5-pyridyl or.!. 2-chloro-5-thiazolyl.   
     
     
       5. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein   R 1  and R 2  are hydrogen or methyl,   R 3  is ##STR43##  in which R 5  and R 6  are hydrogen or methyl, . .Y is N,.!. and   Z is 2-chloro-5-pyridyl.   
     
     
       6. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein such compound is 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine of the formula ##STR44## 
     
     
       7. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein such compound is 3-(2-chloro-5-pyridylmethyl)-1,1-dimethyl-2-nitroguanidine of the formula ##STR45## 
     
     
       8. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein such compound is 3-(2-chloro-5-pyridylmethyl)-1,3-dimethyl-2-nitroguanidine of the formula ##STR46## 
     
     
       9. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein such compound is 3-(2-chloro-5-pyridymethyl)-1,1,3-trimethyl-2-nitroguanidine of the formula ##STR47## 
     
     
       10. A compound according to claim . .1.!. .Iadd.15.Iaddend., wherein such compound is 3-(2-chloro-5-pyridylmethyl)-3-methyl-2-nitroguanidine of the formula ##STR48## . . 
     
     
       11.  A compound according to claim 1, wherein such compound is 3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine of the formula ##STR49## 
     
     
       12. An insecticidal composition comprising an insecticidally effective amount of a compound according to claim 1 and a diluent. 
     
     
       13. A method of combating insects which comprises applying to such insects or to a locus from which it is desired to exclude such insects an insecticidally effective amount of a compound according to claim 1 and a diluent. 
     
     
       14. The method according to claim 13, wherein such compound is . .3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,1-dimethyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,3-dimethyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,1,3-trimethyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-3-methyl-2-nitroguanidine; or.!.   3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine. .Iadd.   
     
     
       15.  A nitro compound of the formula ##STR50##.Iaddend.wherein R 1  and R 2  are hydrogen or C 1-4  -alkyl,   R 3  is --S--R 4  or ##STR51## R 4  represents C 1-4  -alkyl,   R 5  and R 6  represent hydrogen or C 1-4  -alkyl, and   Z is pyridyl substituted by chlorine or methyl..Iadd.   
     
     
       16.  A compound according to claim 15, wherein R 1  and R 2  are hydrogen or methyl,   R 3  is ##STR52##.Iaddend.R 4  is methyl,   R 5  and R 6  are hydrogen or methyl, and   Z is pyridyl substituted by chlorine or methyl..Iadd.   
     
     
       17.  A compound according to claim 15, wherein R 1  and R 2  are hydrogen or methyl,   R 3  is ##STR53##.Iaddend. in which R 5  and R 6  are hydrogen or methyl, and   Z is 2-chloro-5-pyridyl..Iadd.   
     
     
       18.  An insecticidal composition comprising an insecticidally effective amount of a compound according to claim 15 and a diluent..Iaddend..Iadd.19. A method of combating insects which comprises applying to such insects or to a locus from which it is desired to exclude such insects an insecticidally effective amount of a compound of the formula ##STR54##.Iaddend.wherein R 1  and R 2  are hydrogen or C 1-4  -alkyl,   R 3  is --S--R 4  or ##STR55## R 4  represents C 1-4  -alkyl,   R 5  and R 6  represent hydrogen or C 1-4  -alkyl, and   Z is pyridyl substituted by chlorine or methyl,   
     
     
       in admixture with a diluent..Iadd.20.  The method according to claim 19, wherein such compound is 3-(2-chloro-5-pyridylmethyl)-1-methyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,1-dimethyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,3-dimethyl-2-nitroguanidine;   3-(2-chloro-5-pyridylmethyl)-1,1,3-trimethyl-2-nitroguanidine; or   3-(2-chloro-5-pyridylmethyl)-3-methyl-2-nitroguanidine..Iaddend.