Imperial Chemical Industries Limited

Nazim Punja

Philip D Bentley

Ian T Kay

William G Rathmell

Peter J Cleare

Bernard W Terry

Winston Costain

Compounds of formula I wherein R.sup.1 and R.sup.2 are haloalkyl or halo, X is O, S, S(O), SO.sub.2 or NR.sub.4 where R.sub.4 is H or alkyl, R.sup.3 is alkyl and n is 1 to 4, and compositions comprising them, useful as insecticides. ##STR1##

Halogenated esters

This invention relates to novel cyclopropane derivatives useful as insecticides, to processes for their preparation, to compositions comprising them and to methods of combatting insect and similar invertebrate pests using them.

Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel. ##STR1##

Halogenated benzyl alcohols and halides

Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.

Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides

This invention relates to alkenyl and alkynyl acylanilide derivatives useful as pesticides, especially as fungicides, to a process for preparing them, to pesticidal compositions containing them, and to a method of combating pests using them.

Fungicidal compounds, compositions and processes

4-.beta., .beta.-dichlorovinyl (or dibromovinyl)-3,3-dimethylbutyrolactones are prepared from 1,1-dichloro (or dibromo)-4-methylpenta-1,3-diene by reacting with an acid of formula CH.sub.2 R.CO.sub.2 H in presence of a salt of a metal in one of its higher valency states, especially manganese (III), cerium (IV), or vanadium (V). Higher yields are obtained in the presence of the anhydride of the acid and of the sodium or potassium salt of the acid. Treatment of the lactones with an inorganic acid halide opens the lactone ring with formation of the corresponding 4-haloacid halide, which with alcohols affords the corresponding 4-haloacid ester, cyclised by bases to a 3-.beta.,.beta.-dichloro (or dibromo)vinyl-2,2-dimethylcyclopropanecarboxylic ester, intermediate for insecticides such as the m-phenoxybenzyl ester.

Lactones

This invention relates to alkynyl acylanilide derivatives useful as pesticides, to a process for preparing them, to pesticidal compositions containing them, and to a method of combating pests using them.

Fungicidal acylanilide compounds

A compound of the formula: ##STR1## wherein X and Y are independently selected from cyano and alkoxycarbonyl containing from 1 to 4 carbon atoms in the alkoxy group, and Q, R and Z are independently selected from chlorine and bromine provided that Q is always bromine when either Z or R is bromine. The compounds are useful as chemical intermediates.

4-Halo-3,3-dimethyl-6,6,6-trihalohexanoate intermediates

Preparation of ethyl 2(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropane carboxylate and ethyl 1-cyano-2(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylate as intermediates.

2(2,2-Dichlorovinyl)-3,3-dimethyl-cyclopropane carboxylates

1-acetyl or 1-cyano-2(2,2-dichlorovinyl)-3,3-dimethylcyclopropane. These compounds are useful intermediates.

1-Acetyl or 1-cyano-2(2,2-dichlorovinyl)-3,3-dimethyl cyclopropane

Compounds of the formula ##STR1## wherein R.sup.1 represents a branched lower alkyl radical; R.sup.2 represents a phenyl group optionally substituted with halogeno or lower alkyl radicals; R.sup.3 and R.sup.4 represent halogeno radicals; and R.sup.5 represents a hydrogen atom or the cyano radical. These compounds are useful as insecticides.

Insecticidal esters

Compounds of the formula ##SPC1## Wherein X is halogen or hydroxy; R.sup.3 and R.sup.4 represent halogen radicals; and R.sup.5 represents a hydrogen atom or the cyano radical. These compounds are used in the preparation of pesticidal cyclopropane carboxylates.

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Crowthorne, United Kingdom

Nazim Punja