Insecticidally active nitro guanidine compounds

Insecticidal novel nitro compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are hydrogen or C.sub.1-4 alkyl, R.sup.3 is --S--R.sup.4 or ##STR2## in which R.sup.4 is C.sub.1-4 alkyl, R.sup.5 and R.sup.6 are hydrogen or C.sub.1-4 alkyl,Y is CH or N, andZ is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halogen or C.sub.1-4 alkyl, provided that where Y is CH,then R.sup.1 is C.sub.1-4 alkyl.

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Claims

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.

15. A nitro compound of the formula ##STR50##.Iaddend.wherein

R.sup.1 and R.sup.2 are hydrogen or C.sub.1-4 -alkyl,
R.sup.3 is --S--R.sup.4 or ##STR51## R.sup.4 represents C.sub.1-4 -alkyl,
R.sup.5 and R.sup.6 represent hydrogen or C.sub.1-4 -alkyl, and
Z is pyridyl substituted by chlorine or methyl..Iadd.

16. A compound according to claim 15, wherein

R.sup.1 and R.sup.2 are hydrogen or methyl,
R.sup.3 is ##STR52##.Iaddend.R.sup.4 is methyl,
R.sup.5 and R.sup.6 are hydrogen or methyl, and
Z is pyridyl substituted by chlorine or methyl..Iadd.

17. A compound according to claim 15, wherein

R.sup.1 and R.sup.2 are hydrogen or methyl,
R.sup.3 is ##STR53##.Iaddend. in which R.sup.5 and R.sup.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.sup.1 and R.sup.2 are hydrogen or C.sub.1-4 -alkyl,
R.sup.3 is --S--R.sup.4 or ##STR55## R.sup.4 represents C.sub.1-4 -alkyl,
R.sup.5 and R.sup.6 represent hydrogen or C.sub.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.
Referenced Cited
U.S. Patent Documents
3457188 July 1969 Niemers et al.
4499097 February 12, 1985 Tomcufcik et al.
Foreign Patent Documents
0302389 February 1989 EPX
302833 February 1989 EPX
303570 February 1989 EPX
234064 October 1987 JPX
233903 September 1988 JPX
2201596 February 1988 GBX
Other references
  • Nihon Kagaku Zasshi, vol. 83, No. 2, pp. 218-222, 1962. Bulletin of National Institute of Hygienic Sciences, No. 88, 1970, "Screening Test on Anticancer and . . . ", Kamiya and Koshinuma, et al. Bulletin of National Institute of Hygienic Sciences, No. 102, 1984, "Sunthesis of 3-Nitro-1-nitroso . . . ", Kamiya and Koshinuma, et al.
Patent History
Patent number: RE35811
Type: Grant
Filed: Oct 3, 1995
Date of Patent: May 26, 1998
Assignee: Nihon Bayer Agrochem K.K. (Tokyo)
Inventors: Kozo Shiokawa (Kanagawa-ken), Shinichi Tsuboi (Tokyo), Koichi Moriya (Tochigi), Yumi Hattori (Ibaraki), Ikuro Honda (Tokyo), Katsuhiko Shibuya (Tochigi)
Primary Examiner: Zinna Northington Davis
Law Firm: Sprung Kramer Schaefer & Briscoe
Application Number: 8/538,756