Insect growth regulating activity of 1,5‐disubstituted imidazoles against <i>Bombyx mori</i> and <i>Oncopeltus fasciatus</i>

Kuwano, Eiichi; Hisano, Tomomi; Etō, Morifusa; Suzuki, Koichi; Unnithan, Gopalan C.; Bowers, William S.

doi:10.1002/ps.2780340312

Cited by 14 publications

(6 citation statements)

References 13 publications

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“…Tentagel resin is unstable to basic conditions and hence polystyrene-SH was prepared from Merrifield resin according to the method of Kobayashi by Ganesan et al [7]. This resin 3 known as PS-TosMIC was found to be stable and worked efficiently for the synthesis of 5-aryloxazoles (43). The yields of 43 obtained are reported in Table V.…”

Section: Oxazolesmentioning

confidence: 98%

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

Tandon¹,

Rajagopalan²

2003

Sulfur Reports

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TosMIC, a versatile synthon in organic chemistry, has been extensively used for the synthesis of a wide variety of small, medium and large ring heterocycles. It has immense implications in the synthesis of nitriles, aldehydes, ketones, alkanes, cyclophanes and large number of natural products. Several drug intermediates and pharmacologically active compounds have been synthesized from TosMIC. In addition, chiral TosMIC analogs have been synthesized and employed for synthesis of optically active compounds.

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Section: Oxazolesmentioning

confidence: 98%

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

Tandon¹,

Rajagopalan²

2003

Sulfur Reports

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“…) and TH‐14 have a very similar IC50 for JH synthesis (36 and 47 nM), but TH‐27 is more specific for the epoxidase than TH‐14, which inhibits the transferase as well . Although some imidazole compounds from Prof. E Kuwano's programme have shown in vivo activity (mainly in the silkworm), this has not led to a strong follow‐up. Now, with the ability to test inhibitors in vivo in conjunction with testing recombinant CYP15 enzymes in vitro , the time may have come to revisit this target, because inhibitors of JH biosynthesis would have an anti‐JH effect, and thus overcome the drawbacks of juvenoids in insect control …”

Section: P450 Enzymes Drugs and Agrochemicalsmentioning

confidence: 99%

Insect P450 inhibitors and insecticides: challenges and opportunities

Feyereisen

2014

Pest Management Science

113

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P450 enzymes are encoded by a large number of genes in insects, often over a hundred. They play important roles in insecticide metabolism and resistance, and growing numbers of P450 enzymes are now known to catalyse important physiological reactions, such as hormone metabolism or cuticular hydrocarbon synthesis. Ways to inhibit P450 enzymes specifically or less specifically are well understood, as P450 inhibitors are found as drugs, as fungicides, as plant growth regulators and as insecticide synergists. Yet there are no P450 inhibitors as insecticides on the market. As new modes of action are constantly needed to support insecticide resistance management, P450 inhibitors should be considered because of their high potential for insect selectivity, their well-known mechanisms of action and the increasing ease of rational design and testing.

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“…insect diapause, molting, and metamorphosis. Disruption of these events by KK-42 or more potent analogues might be useful in controlling pest species (Pratt et al, 1990;Kuwano et al, 1992). In this paper, we report the effects of KK-42 on growth, development, molting, and metamorphosis of diapauseand nondiapause-bound 0. nubilcllis larvae.…”

Section: Introductionmentioning

confidence: 96%

“…Because of KK-42's reported ability to act as an anti-JH, an antiecdysteroid, and/or a stimulatory factor in breaking diapause, it is a valuable tool that can be used in investigating the role of these factors in controlling insect diapause, molting, and metamorphosis. Disruption of these events by KK-42 or more potent analogues might be useful in controlling pest species (Pratt et al, 1990;Kuwano et al, 1992). In this paper, we report the effects of KK-42 on growth, development, molting, and metamorphosis of diapauseand nondiapause-bound 0. nubilcllis larvae.…”

Section: Introductionmentioning

confidence: 98%

Effect of KK‐42 on growth, development, molting, and metamorphosis of the european corn borer, Ostrinia nubilalis (Hübner)

Gelman

Bell

DeMilo

et al. 1995

Arch Insect Biochem Physiol

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(1 -benzyl-5-I(E)-2,6-dimethyl-l ,S-heptadienyll imidazole), administered by feeding, delayed the growth and development ot nondiapause-bound and diapause-bound Ostrinia nubilaiis larvae and increased the length of the instar. At doses of 80-240 ppm, 62-1 00% ot nondiapause-bound fourth instars precociously pupated or remained as fourth instars, while 52-100% of diapausebound fourth instars did not molt to the fifth instar. Injection of these nondiapause-and diapause-bound KK-42-fed fourth instars with ecdysone elicited a molt and resulted in the production of larval-pupal intermediates. When mature fourth instar controls were similarly injected, they molted into normal fifth instars. These results support the view that KK-42 delaydinhibits ecdysteroid production. Both eupyrene and apyrene spermiogenesis were prematurely initiated in nondiapause-bound fourth instars that were fed on mediuni containing 160 ppm KK-42. Fenoxycarb, a potent juvenile hormone mimic, rescued nondiapause-bound fourth instars from precocious pupation. All fenoxycarbtreated larvae either molted to the fifth instar or remained as fourth instars and eventually died. These results support the view that treatment with KK-42 inhibits jH production. When KK-42 treatment was begun in the third instar, a considerable number of nondiapause-bound and some diapause-bound third instars precociously molted to the fifth instar. There was a correlation between weight and the incidence of precocious molting in that third instars destined to skip the fourth instar attained a weight, as pharate fifth instars, of two to three times more than pharate fourth instar ccntrols. Similarly, fourth instars that were destined to undergo precocious pupation attained a weight, as pharate pupae, that was approximately two times more than pharate fifth instar controls. More potent analogues of

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Insect growth regulating activity of 1,5‐disubstituted imidazoles against Bombyx mori and Oncopeltus fasciatus

Cited by 14 publications

References 13 publications

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

Insect P450 inhibitors and insecticides: challenges and opportunities

Effect of KK‐42 on growth, development, molting, and metamorphosis of the european corn borer, Ostrinia nubilalis (Hübner)

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