A New Class of Pyrethroidal Insecticides; α-Substituted Phenylacetic Acid Esters

Natural products for pest control: an analysis of their role, value and future

“…In some cases, these NPs have been, at least in part, the inspiration for the development of totally synthetic insecticides; for example, the now classic example of the development of a highly successful class of insecticides, the synthetic pyrethroids, modeled on the NP pyrethrum . The synthetic pyrethroids permethrin and fenvalerate, acting on voltage‐sensitive sodium channels, along with a host of other pyrethroid insecticides that followed, were the culmination of very long‐term efforts to devise highly potent, photostable insecticides using pyrethrum as a model . Likewise, the N ‐methyl phenylcarbamates, inhibitors of acetylcholinesterase (AChE), were developed, in part, on the basis of the NP physostigmine (eserine) .…”

“…63,64 The synthetic pyrethroids permethrin and fenvalerate, acting on voltage-sensitive sodium channels, 65,66 along with a host of other pyrethroid insecticides that followed, were the culmination of very long-term efforts to devise highly potent, photostable insecticides using pyrethrum as a model. 63,64,67,68 Likewise, the N-methyl phenylcarbamates, inhibitors of acetylcholinesterase (AChE), were developed, in part, on the basis of the NP physostigmine (eserine). 69 -71 Numerous other examples exist (Table 3), including the development of cartap and other nereistoxin analogs inspired by the NP nereistoxin, 50 methroprene, fenoxycarb and ultimately pyriproxyfen from insect juvenile hormone III, 72 chlorfenapyr (AC 303,630), an inhibitor of oxidative phosphorylation, from dioxypyrrolomycin, 73,74 and fluacrypyrim, an MET complex III inhibitor inspired by the -methoxyacrylates.…”

Development of and future prospects for pyrethroid chemistry

“…As shown in Fig 6 many pyrethroids having a chemically stable phenoxybenzyl group as the alcohol moiety but a modi®ed acid moiety were invented. Pyrethroids such as permethrin (17) 20 and fenvalerate (18) 21 have been used for agricultural purposes because of their chemical stability. Studies on this modi®cation in the 1970s were conducted by agrochemical companies around the world.…”

Structure, bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo-propanecarboxamide

“…Although, pretty many cyclopropane compounds had been synthesized, few are biologically active and structurally stable. A series of alkyl substituted cyclopropane compounds were prepared by Ohno and his parterners [1]. Subsequently, a kind of cyclopropane derivatives with good activity of inhibiting Ketol-acid reductoisomerase (KARI) were also synthesized and tested after introducing a carboxyl moiety onto the cyclopropane by Duggleby [2] and Gerwick et al [3].…”