Synthesis and Miticidal and Insecticidal Activities of Biphenylhydrazinecarboxylates

Abstract

Ten biphenylhydrazinecarboxylates were obtained by the condensation of o-biphenylhydrazine with alkyl chloroformates. The miticidal and insecticidal activities of the new compounds were evaluated against Tetranychus urticae and Sogatodes orizicola. Structure-activity relationships for the screened compounds are discussed. Some of the compounds displayed greater activity than did the commercial standards, propargite and carbofuran.

The Discovery of Bifenazate, a Novel Carbazate Acaricide

“…Therefore we synthesized and tested a variety of alkyl ortho-biphenylcarbazates. Alkyl ortho-biphenylcarbazates of the type 4 were synthesized by reaction of orthobiphenylhydrazine 3, readily prepared from commercially available ortho-biphenylamine by diazotization followed by SnCl 2 reduction, with alkyl chloroformates (Scheme 1) [6]. Optimal activity (80-100% control of mites at 100 ppm) in this series was obtained when the ester function consisted of a straight-or branched-chain alkyl group of three or four carbon atoms.…”

“…3) were synthesized from meta-biphenylhydrazine in a similar way to that for the ortho-biphenylcarbazates [7]. The acaricidal activities of alkyl metabiphenylcarbazates paralleled their orthobiphenyl-substituted counterparts with optimal acaricidal control of 80-100% at 100 ppm when the ester function consisted of three or four carbon length alkyl groups.…”

“…6). Trifluoroacetylcarbazates 11 were prepared from the corresponding carbazates by reaction with trifluoroacetic anhydride [7]. The acaricidal activities of the trifluoroacetylcarbazates were generally parallel to those of the carbazates from which they were made.…”

Organophosphate insecticides and acaricides antagonise bifenazate toxicity through esterase inhibition in Tetranychus urticae

“…Bifenazate [D2341; isopropyl 3‐(4‐methoxybi‐ phenyl‐3‐yl)carbazate], an acaricidal hydrazine derivative, was discovered in 1990 by Uniroyal Chemical and commercialised in 1999 2–4. It is a selective miticide that provides outstanding control of a variety of mite pests on many crops including greenhouse ornamentals and fruits such as apples, pears and citrus.…”

Susceptibility of an organophosphate resistant strain of the two-spotted spider mite (Tetranychus urticae) to mixtures of bifenazate with organophosphate and carbamate insecticides

“…Bifenazate, a hydrazine derivative with acaricidal activity, was discovered in 1990 by Uniroyal Chemical and commercialised in 1999 (Dekeyser et al 1994(Dekeyser et al , 2003Grosscurt and Avella 2005). It shows excellent activity against many phytophagous mite species including T. urticae, providing quick knockdown through contact activity and long residual control (4 weeks) (Ochiai et al 2007).…”