Pesticidal fluoroolefins

Details Pesticidal fluoroolefins Pesticidal fluoroolefins

1995-03-16

1998-06-09

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Halogen containing

570143, 570133, 568631, 568633, 568634, 585 20, 585 25, C07C 2204

Patent

active

057637008

DESCRIPTION:

BRIEF SUMMARY
This invention relates to pesticidal compounds and is particularly concerned with soil insecticides.
There is continuing interest in the discovery of compounds which, while not necessarily having wide spectrum pesticidal activity, have high activity in a particular mode of application and/or in respect of particular pests, especially insect and similar invertebrate pests which inhabit the soil. Thus, for example, GB Patent Specification No. 2066810 describes certain fluorinated-benzyl esters of cyclopropane carboxylic acids which have, inter alia, soil insecticidal activity. However, there is little understanding in the pesticide art of the various factors which contribute and interact in order to provide compounds having good activity against soil borne pests. For good soil activity, many more factors come into play, affecting migration, persistence and transference of the active compound to the soil borne insect, than is the case when considering topical application. A review of such factors is to be found in a recent paper by Simmons et al (1992) J. Agric. Food Chem., 40, 1432-1436.
It has now been surprisingly found that good soil insecticide activity is demonstrated by a group of non-ester aryl cyclopropyl substituted olefins having a fluorine substituent at the site of olefinic unsaturation.
The present invention comprises pesticidal compounds of formula I: ##STR2## in which formula: Ar.sub.A represents a phenyl or naphthyl group optionally substituted by one or more groups selected from halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 haloalkyl; and group which is optionally further substituted; Ar.sub.B about the double bond being mutally trans.
Preferably Ar.sub.A is a substituted phenyl group. Substitution is preferably at the 3-(meta) and/or 4-(para) position by fluorine, bromine, chlorine, a C.sub.1 -C.sub.6 alkyl group (such as methyl or t-butyl), a C.sub.1 -C.sub.6 alkoxy group (such as methoxy or ethoxy), a C.sub.1 -C.sub.6 haloalkoxy group comprising one or more halogens (such as --OCF.sub.3 and --OCF.sub.2 H) or a C.sub.1 -C.sub.6 haloalkyl group (e.g. CF.sub.3). Ar.sub.A generally carries no more than two substituents.
Ar.sub.B may be considered as representing the residue of a benzyl alcohol Ar.sub.B CH.sub.2 OH as described and claimed in UK Patent Specification No. 1413491 and which gives rise to significant insecticidal activity when acid. Such significant insecticidal activity is demonstrated by a potency towards houseflies of usually at least 5 relative to bioresmethrin =100.
The group 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, more especially at the 4-(para) position. 3-phenoxyphenyl and 4-fluoro-3-phenoxyphenyl groups Ar.sub.B are of particular interest.
It has been found that, although the presence of fluorine in the group Ar.sub.B may lead to enhanced activity of the compound of formula I as a soil insecticide, this is by no means a constant improvement and in many cases the activity as a soil insecticide is diminished by fluorine incorporation. In contrast, there has been found a marked and consistent improvement in soil insecticide activity of compounds of formula I, with a fluorine on an olefinic carbon, when compared with compounds of formula I lacking such a fluorine.
The compounds of this invention constitute a selection from the broad class of compounds claimed in our prior patent GB 2,167,749. The prior compounds were described as having insecticidal activity against a wide range of plant pests and as being of especial value for use against rice pests. The compounds of the present invention are therefore a group of novel compounds found to have a specific and unexpected utility as soil insecticides.
The invention further includes a process for the preparation of a pesticidal compound of formula I in which a compound comprising a moiety ##STR3## and a compound comprising a moiety Ar.su

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