Development of and future prospects for pyrethroid chemistry

Katsuda, Yoshio

doi:10.1002/(sici)1096-9063(199908)55:8<775::aid-ps27>3.3.co;2-e

Cited by 28 publications

(42 citation statements)

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“…Two major objectives have driven the development of pyrethroid chemical structures and selection of isomer compositions: namely, increases in both insecticidal potency and photostability [48,91,125,126,156]. Fig.…”

Section: Structure-lethality Relationships In Ratsmentioning

confidence: 99%

Neurobehavioral toxicology of pyrethroid insecticides in adult animals: A critical review

Wolansky

Harrill

2008

Neurotoxicology and Teratology

270

143

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Pyrethroids are pesticides with high selectivity for insects. In order to identify strengths and gaps in the database for pyrethroid neurobehavioral toxicology, we have critically analyzed the data from peer-reviewed literature. This review includes dose-response data that have been recently generated demonstrating consistent findings for low-dose, acute, oral exposure to pyrethroids in small rodents. All pyrethroids tested (i.e., about twenty compounds), regardless of structure, produce a decrease in motor activity in a variety of test protocols. The range of relative potencies varies more than two orders of magnitude, and thresholds for motor activity were found well below doses that produce overt signs of poisoning. Six compounds (allethrin, permethrin, cis-permethrin, deltamethrin, cypermethrin, and fenvalerate) impair schedule-controlled operant responding, seven compounds (pyrethrum, bifenthrin, S-bioallethrin, permethrin, beta-cyfluthrin, cypermethrin, and deltamethrin) decrease grip strength, and two compounds (deltamethrin and alpha-cypermethrin) produce incoordination using the rotarod. In addition, while compounds lacking an alpha-cyano group (e.g., cismethrin, permethrin, bifenthrin) induce an increase in acoustic-evoked startle response amplitude, cyano compounds (e.g., deltamethrin, cypermethrin, cyfluthrin) produce the opposite outcome. Other endpoints (e.g., tremor intensity, sensory response) have been only occasionally explored. A synthesis of the neurobehavioral evidence relating to the action of pyrethroids indicates that some differences in the experimental findings across compounds are also present in the low-effective dose range. For risk assessment purposes, a strategy that takes into account data from an array of neurobehavioral endpoints is needed to capture the heterogeneity of pyrethroid-induced adverse effects and accurately inform policy decisions.

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Section: Structure-lethality Relationships In Ratsmentioning

confidence: 99%

Neurobehavioral toxicology of pyrethroid insecticides in adult animals: A critical review

Wolansky

Harrill

2008

Neurotoxicology and Teratology

270

143

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“…Pyrethrins (Figure 1(a)) are natural insecticides that are synthesized by the chrysanthemum species, Tanacetum cinerariifolium (earlier species name: Chrysanthemum cinerariaefolium ) of the Asteraceae family and have been used for pest control since medieval times (Crombie, 1995; Katsuda, 1999). Although the market for pyrethrins has been taken over by synthetic pyrethroids, there is still worldwide demand for natural pyrethrins as organic pesticides.…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of a GDSL lipase‐like protein that catalyzes the ester‐forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium– a new target for plant protection

Kikuta¹,

Ueda

Takahashi

et al. 2012

The Plant Journal

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SUMMARYAlthough natural insecticides pyrethrins produced by Tanacetum cinerariifolium are used worldwide to control insect pest species, little information is known of their biosynthesis. From the buds of T. cinerariifolium, we have purified a protein that is able to transfer the chrysanthemoyl group from the coenzyme A (CoA) thioester to pyrethrolone to produce pyrethrin I and have isolated cDNAs that encode the enzyme. To our surprise, the active principle was not a member of a known acyltransferase family but a member of the GDSL lipase family. The recombinant enzyme (TcGLIP) was expressed in Escherichia coli and displayed the acyltransferase reaction with high substrate specificity, recognized the absolute configurations of three asymmetric carbons and also showed esterase activity. A S40A mutation in the Block I domain reduced both acyltransferase and esterase activities, which suggested an important role of this serine residue in these two activities. The signal peptide directed the localization of TcGLIP::enhanced green fluorescent protein (EGFP) fusion, as well as EGFP, to the extracellular space. High TcGLIP gene expression was observed in the leaves of mature plants and seedlings as well as in buds and flowers, a finding that was consistent with the pyrethrin I content in these parts. Expression was enhanced in response to wounding, which suggested that the enzyme plays a key role in the defense mechanism of T. cinerariifolium.

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“…Pyrethrins interfere with the gating kinetics of sodium channels in nerve axons, the same qualitative mechanism of action as DDT and synthetic pyrethroids 24. Pyrethroid insecticides are synthetic analogues of pyrethrins, with higher potency against insects and photostability, and their development shifted from the synthesis of new compounds to the development of enriched active isomers in the late 1980s 24–26. This trend in pyrethroid development led to the eventual replacement of isomeric mixtures with the enriched isomers, as illustrated in the field of stored‐product protection by the replacement of cyfluthrin with β‐cyfluthrin.…”

Section: Introductionmentioning

confidence: 99%

Acute lethal and behavioral sublethal responses of two stored‐product psocids to surface insecticides

Guedes

Campbell

Arthur

et al. 2008

Pest Management Science

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Development of and future prospects for pyrethroid chemistry

Cited by 28 publications

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Neurobehavioral toxicology of pyrethroid insecticides in adult animals: A critical review

Neurobehavioral toxicology of pyrethroid insecticides in adult animals: A critical review

Identification and characterization of a GDSL lipase‐like protein that catalyzes the ester‐forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium– a new target for plant protection

Acute lethal and behavioral sublethal responses of two stored‐product psocids to surface insecticides

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