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Claims for Patent: 4,024,163

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Claims for Patent: 4,024,163

Title: Insecticides
Abstract:New insecticides are of formula: ##STR1## wherein R.sup.1 represents hydrogen or a methyl group; R.sup.2 represents hydrogen or a halogeno or lower alkyl group; R.sup.3 represents hydrogen or a halogeno, lower alkyl (which is different to R.sup.2 when R.sup.2 represents a lower alkyl group) or carbo(loweralkoxy) group which contains at least 2 carbon atoms in the lower alkoxy residue when R.sup.2 represents methyl or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent a cycloalkylene ring having at least one endocyclic carbon to carbon double bond; with the proviso that (a) R.sup.2 and R.sup.3 each represent hydrogen only when R.sup.1 represents methyl and (b) R.sup.3 contains at least 2 carbon atoms when R.sup.1 and R.sup.2 each represent hydrogen; and R represents a group which form insecticidal esters with chrysanthemic acid e.g. 5-benzyl-3-furylmethyl, 3-phenoxybenzyl, .alpha.-cyano-3-phenoxybenzyl. The esters are prepared by forming the ester linkage conventionally or by a Wittig reaction using a 3-formyl- or 3-acetyl-2,2-dimethyl cyclopropane carboxylic acid esterified with the desired residue or by an alkyl group which is subsequently converted to the desired residue.
Inventor(s): Elliott; Michael (Harpenden, EN), Janes; Norman Frank (Luton, EN), Pulman; David Allen (Harpenden, EN)
Assignee: National Research Development Corporation (London, EN)
Application Number:05/497,056
Patent Claims: 1. A compound of the formula: ##STR18## wherein: R.sup.2 and R.sup.3 independently represent halogen, and R is 5-benzyl-3-furylmethyl.

2. A compound according to claim 1 which is a 5-benzyl-3-furylmethyl ester of [1R-cis]- or [1R-trans]-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropane carboxylic acid or a mixture of the cis and trans isomers.

3. A compound according to claim 1 which is a 5-benzyl-3-furylmethyl ester of [1R,cis] or [1R, trans] 2,2-dimethyl-3-(2,2-difluorovinyl) cyclopropane carboxylate.

4. A compound according to claim 1 wherein R.sup.2 and R.sup.3 each independently represent bromine or chlorine or fluorine.

5. A compound according to claim 1 in the form of a (+)-trans, (+)-cis, (.+-.)-trans, (.+-.)-cis, (+)-cis-trans, or (.+-.)-cis-trans isomer, the stereochemistry being in relation to the cyclopropane ring.

6. An insecticidal composition comprising a compound according to claim 1 together with a diluent or carrier.

7. A method of insect control which comprises applying to an insect or an environment susceptible to insect attack a compound in accordance with claim 1.

8. A compound of the formula: ##STR19## wherein: R.sup.2 and R.sup.3 independently represent halogen, and R is 3-phenoxybenzyl.

9. A compound according to claim 8 which is 3-phenoxybenzyl(.+-.)-cis-trans or (.+-.)-cis or (.+-.)-trans-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropane carboxylate.

10. A compound according to claim 8 which is a 3-phenoxybenzyl ester of [1R-cis]- or [1R-trans]-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane carboxylic acid or a mixture of the cis and trans isomers.

11. A compound according to claim 8 which is a 3-phenoxybenzyl, ester of [1R,cis] or [1R,trans] 2,2-dimethyl-3-(2,2-difluorovinyl cyclopropane carboxylate.

12. A compound according to claim 8 wherein R.sup.2 and R.sup.3 each represent bromine or each represent chlorine and R represents 3-phenoxybenzyl.

13. A compound according to claim 8 wherein R.sup.2 and R.sup.3 each independently represent bromine or chlorine or fluorine.

14. A compound according to claim 8 in the form of a (+)-trans, (+)-cis, (.+-.)-trans, (.+-.)-cis, (+)-cis-trans, or (.+-.)-cis-trans isomer, the stereochemistry being in relation to the cyclopropane ring.

15. A compound according to claim 8, which is 3-phenoxybenzyl (.+-.)-cis-trans-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropane carboxylate.

16. An insecticidal composition comprising a compound according to claim 8 together with a diluent or carrier.

17. A method of insect control which comprises applying to an insect or an environment susceptible to insect attack a compound in accordance with claim 8.

18. A compound of the formula: ##STR20## wherein: R.sup.2 and R.sup.3 independently represent halogen, and R is .alpha.-cyano-3-phenoxybenzyl.

19. A compound according to claim 18 which is (.+-.)-.alpha.-cyano-3-phenoxybenzyl [1R-trans] or [1R,cis] 2,2-dimethyl-3-(2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylate.

20. A compound according to claim 18 which is the isomer of .alpha.-cyano-3-phenoxybenzyl [1R,cis] 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane carboxylate having a positive [.alpha.].sub.D.sup.20 value when dissolved in ethanol.

21. A compound according to claim 18 which is a .alpha.-cyano-3-phenoxybenzyl ester of [1R,cis] or [1R,trans] 2,2-dimethyl-3-(2,2-difluorovinyl) cyclopropane carboxylate.

22. A compound according to claim 18 wherein R.sup.2 and R.sup.3 each represent bromine or each represent chlorine and R represents .alpha.-cyano-3-phenoxybenzyl.

23. A compound according to claim 18 wherein R.sup.2 and R.sup.3 each independently represent bromine or chlorine or fluorine.

24. A compound according to claim 18 in the form of a (+)-trans, (+)-cis, (.+-.)-trans, (.+-.)-cis, (+)-cis-trans, or (.+-.)-cis-trans isomer, the stereochemistry being in relation to the cyclopropane ring.

25. A compound according to claim 18, which is (.+-.)-.alpha.-cyano-3-phenoxybenzyl-(.+-.)-cis-trans-2,2-dimethyl-3-(2,2- dichlorovinyl) cyclopropane carboxylate.

26. A compound according to claim 18, which is (.+-.)-.alpha.-cyano-3-phenoxybenzyl-(.+-.)-cis-2,2-dimethyl-3-(2,2-dichlo rovinyl) cyclopropane carboxylate.

27. A compound according to claim 18, which is (.+-.)-.alpha.-cyano-3-phenoxybenzyl[1R,cis]2,2-dimethyl-3-(2,2-dichlorovi nyl) cyclopropane carboxylate.

28. An insecticidal composition comprising a compound according to claim 18 together with a diluent or carrier.

29. A method of insect control which comprises applying to an insect or an environment susceptible to insect attack a compound in accordance with claim 18.

30. A compound of the formula: ##STR21## wherein: R.sup.2 and R.sup.3 independently represent halogen, and R is .alpha.-cyano-5-benzyl-3-furylmethyl.

31. A compound according to claim 30 wherein R.sup.2 and R.sup.3 each independently represent bromine or chlorine or fluorine.

32. A compound according to claim 30 in the form of a (+)-trans, (+)-cis, (.+-.)-trans, (.+-.)-cis, (+)-cis-trans, or (.+-.)-cis-trans isomer, the stereochemistry being in relation to the cyclopropane ring.

33. An insecticidal composition comprising a compound according to claim 30 together with a diluent or carrier.

34. A method of insect control which comprises applying to an insect or an environment susceptible to insect attack a compound in accordance with claim 30.
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