Pesticidal fluoroolefins

Details Pesticidal fluoroolefins Pesticidal fluoroolefins

1996-10-21

1999-03-09

Siegel, Alan

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ketone doai

514686, 514687, 514718, 514719, 514720, 570128, 568332, 568333, 568610, A01N 3500, C07C 1908, C07C 4976

Patent

active

058801626

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/GB95/00954 filed Apr. 26, 1995.
This invention relates to pesticidal non-ester pyrethroid olefins having a fluorine substituent at the site of olefinic unsaturation.
As there is evidence of the increased incidence of insect strains resistant to conventionally employed insecticides, so there is continuing interest in the development of new compounds with a new spectrum of activity against susceptible and also resistant species of insect.
Corresponding GB Patent Application No. 9219612.0 describes and claims certain arylcycloalkyl olefins having a fluoride substituent at the site of olefinic unsaturation, which arylcycloalkyl olefins exhibit useful activity as soil insecticides. It has now been found that certain novel 1-substituted, 1,4-diaryl-2-butenes having a 3-fluorine substituent, exhibit valuable activity against a range of insect pests.
Certain 1,4-diaryl-2-butenes have been reported as having insecticidal activity. Thus, U.S. Pat. No. 4,975,451 discloses certain cyclopropyl diaryl 2-butenes which exhibit insecticidal and acaricidal activity while Japanese Patent Publications Nos. 60115545, 60193902 and 60193940 report the existence of insecticidal activity in 1,1-dialkyl-1,4-diaryl 2-butenes. None of these documents discloses or suggests the introduction of a fluorine substituent at the site of olefinic unsaturation.
Therefore, according to the present invention there is provided a pesticidal compound of formula I: ##STR4## in which formula: either R.sup.1 is hydrogen and R.sup.2 represents a cyclopropyl group or R.sup.1 and R.sup.2 each represent an alkyl group, which alkyl groups may be the same or different; group which is optionally further substituted; Ar.sub.B about the double bond being mutually trans.
Preferably Ar.sub.A is a substituted phenyl group. Substitution is preferably at the 4-(para) position, for example by halogen, alkoxy or haloalkoxy.
Ar.sub.B may be a phenyl group substituted by phenoxy, phenyl, benzyl or benzoyl, especially at the 3-(meta) position. Additionally the phenyl group may be substituted, especially by fluorine, especially at the 4-(para) position. 3-phenoxyphenyl and 4-fluoro-3-phenoxyphenyl groups are of particular interest.
One group of compounds in accordance with the invention are those represented by formula I where R.sup.1 is hydrogen and R.sup.2 represents a cyclopropyl group. A second group of compounds are represented by formula I where R.sup.1 and R.sup.2 each independently represent an alkyl group. Preferably R.sup.1 and R.sup.2 are both methyl.
The invention further includes a process for the preparation of a pesticidal compound of formula I in which a compound comprising a moiety ##STR5## and a compound comprising a moiety Ar.sub.B -- are reacted together forming a link --CH.dbd.C(F)CH.sub.2 -- between ##STR6## and Ar.sub.B in the compound of formula I.
A preferred process comprises the catalytic reaction of a nucleophilic species formally of formula Ar.sub.B -- with a compound of formula ##STR7## where Q represents a good leaving group.
Typically, the reaction is carried out in the presence of a transition metal catalyst, which is preferably a copper salt or a complex thereof with a lithium salt.
The nucleophilic species Ar.sub.B -- is generally present in the form of a Grignard reagent of formula Ar.sub.B MgBr or an alkali-metal compound, e.g. Ar.sub.B Li, and the leaving group Q is typically halogen, e.g. bromine, or acyloxy, e.g. acetoxy. The copper salt is suitably a cuprous salt, especially a halide (e.g. bromide or iodide) or cyanide. Complexes of copper of formula Li.sub.2 Cu Y.sub.2 Z.sub.2 where Y and Z represent chlorine, bromine, iodine or cyano, may also be used as catalysts. Such transformations are described by Erdick, Tetrahedron, 1984, 40, 641-657.
The following route illustrates a typical procedure for preparation of compounds I where Q in the final step is acetoxy. ##STR8##
The Grignard reagents Ar.sub.B MgBr may be prepared by the methods and via the intermediates described in UK Patent Nos. 2226315

REFERENCES:
patent: 4975451 (1990-12-01), Cullen et al.

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