The pyrethrins and related compounds. Part XXXIII. Effective combinations in the gemdimethyl‐central group region of non‐ester pyrethroids

Baydar, Ahmet E.; Elliott, M.; Farnham, Andrew W.; Janes, Norman F.; Khambay, B. P. S.

doi:10.1002/ps.2780230305

Cited by 9 publications

(1 citation statement)

References 13 publications

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“…75) Meanwhile, Nissan Chemical found β-gem-dimethyl-β-phenylpropionic acid to be applicable as a pyrethroid acid, 76) even though similar structures such as α-gem-dimethylphenylacetates and α-gem-dimethylβ-phenylpropionates were nearly inactive. 77) Mitsui Toatsu found that gem-dimethyl derivatives lacking the carbonyl group of the ester linkage (namely, converting the ester linkage to the ether linkage) exhibited excellent insecticidal activity. 78) This finding led to the development of etofenprox, which had not only broad-spectrum insecticidal activity but also low fish toxicity.…”

Section: Beyond Cyclopropane and Ester Frameworkmentioning

confidence: 99%

The history of extensive structural modifications of pyrethroids

Ujihara¹

2019

J. Pestic. Sci.

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The structural modification of natural pyrethrins has led to a number of synthetic pyrethroid insecticides, and each compound has its own characteristics. At present, pyrethroid insecticides are applied not only for household use, the original use for pyrethrins, but also for a wide range of uses such as crop protection, pharmaceuticals, and veterinary applications. Quoting primary sources, this review describes the historical view of structural modifications of pyrethroids, with a focus on structural similarities, and their use.

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Section: Beyond Cyclopropane and Ester Frameworkmentioning

confidence: 99%

The history of extensive structural modifications of pyrethroids

Ujihara¹

2019

J. Pestic. Sci.

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The pyrethrins and related compounds. Part XLII:Structure-activity relationships in fluoro-olefin non-ester pyrethroids

1999

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A series of compounds containing¯uorine atoms in place of hydrogen in ole®nic non-ester pyrethroids has been synthesised using a route based on novel intermediates, ie 2-¯uoroallyl acetates, which are coupled with aryl Grignard reagents, and tested against several insect species. In most cases, after introduction of¯uorine at the ole®nic position, the activity remains high in both the 1-aryl-1-(3arylprop-2-enyl)cyclopropane and the (1-aryl-4-arylbut-2-enyl)cyclopropane series. In particular, the former series have potential as soil insecticides, because in tests against Diabrotica balteata, activities were high, and dose-transferability factors were increased by the introduction of¯uorine.

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Pyrethroids

Pap¹

2002

Encyclopedia of Agrochemicals

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The insecticidal synthetic pyrethroids are chemical analogs of the natural pyrethrins occurring in the flower of the Chrysanthemum cinerariaefolium plant. They represent an extensively developed insecticide group with 40 established compounds. Of the 40 commercialized active ingredients, 37 are esters. The application rate of the most potent agricultural pyrethroids is very low, ranging between 5 and 20 g/ha, representing an acceptable environmental load. Pyrethroids are also regarded as safe compounds to warm‐blooded animals and generally to the environment; however, they have some adverse effects on mites, beneficial insects, and aquatic organisms. Pyrethroids are contact nerve poisons acting on gating kinetics of sodium channel in nerve membrane. This action is highly stereoselective. Due to this specific action and their extensive use, the risk of resistance development is relatively high in the targeted insect pest populations. Consequently, resistance management strategies are urgently needed to sustain their appropriate field performance. The registered tendencies of pyrethroid usage and the recent trends in R&D both suggest that this particular group of compounds has been playing an integrated part in present pest management as it is described in our comprehensive survey. Natural Pyrethrin PyrethrinI as the Lead Structure of the Synthetic Pyrethroids Stereochemistry How to Define Pyrethroids Nomenclature Physicochemical Properties Agricultural Use Chemistry Biological Activity, Mode of Action, Metabolism

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The pyrethrins and related compounds. Part XXXIII. Effective combinations in the gemdimethyl‐central group region of non‐ester pyrethroids

Cited by 9 publications

References 13 publications

The history of extensive structural modifications of pyrethroids

The history of extensive structural modifications of pyrethroids

The pyrethrins and related compounds. Part XLII:Structure-activity relationships in fluoro-olefin non-ester pyrethroids

Pyrethroids

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