Nicotine and Other Insecticidal Alkaloids

246

225

Natural products (NPs) have long been used as pesticides and have broadly served as a source of inspiration for a great many commercial synthetic organic fungicides, herbicides and insecticides that are in the market today. In light of the continuing need for new tools to address an ever-changing array of fungal, weed and insect pests, NPs continue to be a source of models and templates for the development of new pest control agents. Interestingly, an examination of the literature suggests that NP models exist for many of the pest control agents that were discovered by other means, suggesting that, had circumstances been different, these NPs could have served as inspiration for the discovery of a great many more of today's pest control agents. Here, an attempt is made to answer questions regarding the existence of an NP model for existing classes of pesticides and what is needed for the discovery of new NPs and NP models for pest control agents.

Section: Insecticidesmentioning

confidence: 99%

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

Gerwick¹,

Sparks²

2014

246

225

“…), isolated from the leaves and stem of the oriental medicinal plant Stemona japonica (Blume) Miq. (Stemonaceae) and known as a potent agonist of insect nicotinic acetylcholine receptors (nAChRs), was considered as a good starting point . Stemofoline shows fast‐acting insecticidal, antifeedant and repellent activities, but its activity is significantly lower than that of commercial products acting on insect nAChRs .…”

Section: Introductionmentioning

confidence: 99%

Flupyradifurone: a brief profile of a new butenolide insecticide

Nauen

Jeschke

Velten

et al. 2014

254

214

BACKGROUNDThe development and commercialisation of new chemical classes of insecticides for efficient crop protection measures against destructive invertebrate pests is of utmost importance to overcome resistance issues and to secure sustainable crop yields. Flupyradifurone introduced here is the first representative of the novel butenolide class of insecticides active against various sucking pests and showing an excellent safety profile.RESULTSThe discovery of flupyradifurone was inspired by the butenolide scaffold in naturally occurring stemofoline. Flupyradifurone acts reversibly as an agonist on insect nicotinic acetylcholine receptors but is structurally different from known agonists, as shown by chemical similarity analysis. It shows a fast action on a broad range of sucking pests, as demonstrated in laboratory bioassays, and exhibits excellent field efficacy on a number of crops with different application methods, including foliar, soil, seed treatment and drip irrigation. It is readily taken up by plants and translocated in the xylem, as demonstrated by phosphor imaging analysis. Flupyradifurone is active on resistant pests, including cotton whiteflies, and is not metabolised by recombinantly expressed CYP6CM1, a cytochrome P450 conferring metabolic resistance to neonicotinoids and pymetrozine.CONCLUSIONThe novel butenolide insecticide flupyradifurone shows unique properties and will become a new tool for integrated pest management around the globe, as demonstrated by its insecticidal, ecotoxicological and safety profile. © 2014 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

“…Ryanodine is a major component of the botanical insecticide ryania and is also widely used as a pharmacological tool in studies of the calcium release channels in skeletal and cardiac muscle of both insects and mammals 32. A CoMFA study performed using a set of 19 ryanoids identified several molecular features of the ligands responsible for their ability to bind to the high affinity site of the vertebrate ryanodine receptor (RyR) 33.…”

Section: Resultsmentioning

confidence: 99%

Ligand‐based computer‐aided pesticide design. A review of applications of the CoMFA and CoMSIA methodologies

Bordás

Kőmíves

Lopata³

2003

An overview is given of the CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indices analysis) methodologies that are established ligand-based molecular design tools widely used by medicinal and pesticide chemists. In the absence of a three-dimensional structure of the target biopolymer, CoMFA and CoMSIA often provide a practical solution to an otherwise intractable problem of proper characterization of ligand-receptor interactions. These techniques are especially important in agrochemistry, where the number of known molecular structures of pesticide targets is limited. The use of CoMFA and CoMSIA in the agrochemical field for modelling the interactions of insecticides, fungicides, herbicides and herbicide safeners with their target binding sites is illustrated by using some selected published work. The CoMFA and CoMSIA models developed have been used successfully to map the properties of unknown receptors, construct hypotheses for ligand-receptor interactions, optimize lead structures, design novel active compounds, and predict biological activities. The application of CoMFA by the present authors for deriving a binding site hypothesis for dichloroacetamide-type herbicide safeners is described in somewhat more detail.