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Details for Patent: 5,004,822

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Details for Patent: 5,004,822

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 halogen, lower alkyl (which is difference to R.sup.2 when R.sup.2 represents a lower alkyl group) or carboloweralkoxy 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, GB2), Janes; Norman F. (Luton, GB2), Pulman; David A. (Harpenden, GB2)
Assignee: National Research Development Corporation (London, GB2)
Filing Date:Feb 19, 1987
Application Number:07/016,289
Claims:1. A single isomer of the formula ##STR18## having 1R,cis configuration, wherein R.sup.1 represents hydrogen, R.sup.2 and R.sup.3 each represent fluorine or each represent chlorine or each represent bromine and R represents OH, Cl, lower alkoxy or O.sup.- M.sup.+ where M.sup.+ is an alkali metal, silver or triethylammonium ion.

2. The isomer of claim 1 wherein both R.sup.2 and R.sup.3 represent bromine.

3. The isomer of claim 1 wherein both R.sup.2 and R.sup.3 represent chlorine.

4. A mixture of isomers of a compound of the formula: ##STR19## said mixture comprises the 1R,cis isomer of said compound and at least one other different isomer of said compound, wherein R.sup.1 is hydrogen or a methyl group, R.sup.2 and R.sup.3 independently represent a halogeno group with the proviso that R.sup.2 and R.sup.3 do not both represent chlorine in a racemic mixture, and R represents OH, Cl, lower alkoxy or O.sup.- M.sup.+ where M.sup.+ is an alkali metal, silver or triethylammonium ion.

5. The mixture of claim 4 in the form of a (1R)cis-trans mixture.

6. The mixture of claim 4 wherein said compound has the formula: ##STR20## wherein R represents OH, Cl, lower alkoxy or O.sup.- M.sup.30 where M.sup.+ is an alkali metal, silver or triethylammonium ion.

7. The mixture of claim 6 in the form of a (1R)cis-trans mixture.

8. The mixture of claim 4 wherein said compound has the formula ##STR21## wherein R represents OH, Cl, lower alkoxy or O.sup.- M.sup.+ where M.sup.+ is an alkali metal, silver or triethylammonium ion.

9. The mixture of claim 8 in the form of a (1R)cis-trans mixture.

10. The mixture of claim 4 consisting essentially of compounds in which the configuration at C.sub.1 and C.sub.3 of the cyclopropane ring is cis.

11. The mixture of claim 6 consisting essentially of compounds in which the configuration at C.sub.1 and C.sub.3 of the cyclopropane ring is cis.

12. The mixture of claim 8 consisting essentially of compounds in which the configuration at C.sub.1 and C.sub.3 if the cyclopropane ring is cis.
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