Synthesis and Precocious Metamorphosis-Inducing Activity of 3-(1-Alkenyl) pyridines

Yoshida, Tetsuya; Shiotsuki, Takahiro; Kuwano, Eiichi

doi:10.1584/jpestics.25.253

Cited by 16 publications

(18 citation statements)

References 3 publications

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“…mori (ShunreiϫShougetsu) larvae were reared on an artificial diet as previously reported. 10) Test compounds in acetone solution were applied topically to the dorsal abdomen of 72-hr-old 2nd instar, 24-hr-old 3rd instar and newly molted 4th instar larvae. Compounds 6 and 6-acid were mixed with the artificial diet at concentrations of 50 and 200 ppm according to the procedure reported.…”

Section: Biological Evaluationmentioning

confidence: 99%

Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy)benzoates and their enantiomers

et al. 2007

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A number of ethyl 4-(2-benzylalkyloxy)benzoates were prepared and their activity to induce precocious metamorphosis was evaluated in larvae of the silkworm, Bombyx mori, which was clearly recognized as a juvenile hormone (JH)-deficiency symptom. Ethyl 4-(2-benzylhexyloxy)benzoate (6) and its 2-benzylheptyloxy analog (7) were found to induce precocious metamorphosis at relatively low doses. Both enantiomers of 6 and 7 were prepared using a chiral auxiliary oxazolidinone. (S)-Enatiomers were more active than (R)-isomers at low doses of 0.1 and 1 mg, but at higher doses their activity was reversed. The activity of compound 6 could be fully counteracted by methoprene, a JH agonist, but not by the dietary administration of 20-hydroxyecdysone. The ester group was important in the ability to induce precocious metamorphosis. The (S)-enatiomer of 6 prolonged the duration of the instar and delayed the onset of cocoon spinning when applied to 5th instar larvae, suggesting that this compound might have JH-like activity as well as anti-JH activity.

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Section: Biological Evaluationmentioning

confidence: 99%

Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy)benzoates and their enantiomers

et al. 2007

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“…mori (ShunreiϫShougetsu) larvae were reared on an artificial diet as previously reported. 9) Test compounds in acetone solution were applied topically to 24 hr-old 3rd instar and newly molted 4th instar larvae. Compounds 4 and 4-acid were mixed with the artificial diet at concentrations of 50 and 200 ppm according to the procedure reported.…”

Section: Biological Evaluationmentioning

confidence: 99%

Synthesis and Anti-Juvenile Hormone Activity of Ethyl 4-[2-(6-Methyl-3-pyridyloxy)alkyloxy]benzoates

et al. 2005

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A series of ethyl 4-[2-(6-methyl-3-pyridyloxy)alkyloxy]benzoates was prepared and tested for activity to induce precocious metamorphosis in larvae of the silkworm, Bombyx mori. Of the compounds tested, ethyl 4-[4-methyl-2-(6-methyl-3-pyridyloxy)pentyloxy]benzoate (5) was the most effective when applied to 24 hr-old 3rd instar larvae. There was no significant difference in precocious metamorphosis-inducing activity between 5R(ϩ)-and 5S(Ϫ)-enatiomers. The activity of compound 5 could be fully counteracted by methoprene, a juvenile hormone (JH) agonist, but not by the dietary administration of 20-hydroxyecdysone. When 3rd instar larvae were treated with compound 5, hemolymph JH esterase activity, which is indispensable for the initiation of pupation in normal last instar larvae, was induced during the 4th instar.

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“…mori (Shunrei x Shougetsu strain) larvae were reared on an artificial diet as previously described. 8) Twenty-four hours after the 3rd molt, the corpora allata were extirpated with fine forceps under a binocular microscope as described by Ohtaki et al 9) Test compounds in an acetone solution (14 ml/larva) were each applied topically to the dorsal abdomen of the larvae within 1 hour after the allatectomy. JH activity was evaluated by the molting into normal 5th instar larvae.…”

Section: Juvenile Hormone Activity Of Ethyl 4-(2-aryloxyhexyloxy)benzmentioning

confidence: 99%

Juvenile Hormone Activity of Ethyl 4-(2-Aryloxyhexyloxy)benzoates with Precocious Metamorphosis-Inducing Activity

Fujita

Ashibe

Yamada

et al. 2007

Bioscience, Biotechnology, and Biochemistry

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Ethyl 4-[2-(6-methyl-3-pyridyloxy)hexyloxy]benzoate (1) and ethyl 4-(2-phenoxyhexyloxy)benzoate (2), which induce precocious metamorphosis in larvae of Bombyx mori, a clear sign of juvenile hormone (JH) deficiency, showed JH activity when topically applied to allatectomized 4th instar larvae of B. mori. Compounds 1 and 2 induced precocious metamorphosis with doses at which they were effective as JH agonists.Key words: juvenile hormone; precocious metamorphosis; anti-juvenile hormone; silkwormSince the juvenile hormone (JH) is involved in a wide range of physiological processes in both developing and mature insects, 1) an anti-JH agent, which chemically blocks the functioning of the JH control system, could be an effective probe for studies on insect endocrinology as well as a potential insect growth regulator.2) We have recently reported ethyl 4-[2-(6-methyl-3-pyridyloxy)-hexyloxy]benzoate (1) 3) and ethyl 4-(2-phenoxyhexyloxy)benzoate (2) 4) as novel anti-JH agents (Fig. 1). These compounds induced precocious metamorphosis in larvae of the silkworm, Bombyx mori, a clear sign of JH deficiency, and their activity could be completely counteracted by the simultaneous application of methoprene, a JH agonist. Compounds 1 and 2 were found by modifying the structure of ethyl 4-[2-(tert-butylcarbonyloxy)butyloxy]benzoate (ETB). ETB is known to show anti-JH activity as well as JH activity toward the tobacco hornworm, Manduca sexta, 5) and B. mori,depending on the dose applied; low doses of ETB induced precocious metamorphosis, but at higher doses, this precocious metamorphosis-inducing activity disappeared and instead, JH activity was observed. Riddiford et al. have reported that ETB acted as a partial antagonist in the Manduca epidermis at the target-tissue level. 7) As previously reported, 3,4) in our bioassay using 24-hr-old 3rd instar larvae of B. mori, ETB at 1 mg induced precocious pupation in only 10% and no activity was observed at higher doses of 10 mg and 40 mg, while compounds 1 and 2 induced precocious metamorphosis even at high doses. ETB clearly acts as a JH agonist to counteract the effect of allatectomy, the induction of precocious metamorphosis, in a dose-dependent manner.6) To determine whether compounds 1 and 2 as well as ETB had JH activity, we tested these compounds on allatectomized 4th instar larvae of B. mori.B. mori (Shunrei x Shougetsu strain) larvae were reared on an artificial diet as previously described. 8)Twenty-four hours after the 3rd molt, the corpora allata were extirpated with fine forceps under a binocular microscope as described by Ohtaki et al.9) Test compounds in an acetone solution (14 ml/larva) were each applied topically to the dorsal abdomen of the larvae within 1 hour after the allatectomy. JH activity was evaluated by the molting into normal 5th instar larvae. Table 1 shows the effects of methoprene, ETB, 1 and 2 against the allatectomized 4th instar larvae. All of the allatectomized and acetone-treated control larvae underwent precocious metamorphosis. ETB as well as methopr...

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Synthesis and Precocious Metamorphosis-Inducing Activity of 3-(1-Alkenyl) pyridines

Cited by 16 publications

References 3 publications

Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy)benzoates and their enantiomers

Synthesis and anti-juvenile hormone activity of ethyl 4-(2-benzylalkyloxy)benzoates and their enantiomers

Synthesis and Anti-Juvenile Hormone Activity of Ethyl 4-[2-(6-Methyl-3-pyridyloxy)alkyloxy]benzoates

Juvenile Hormone Activity of Ethyl 4-(2-Aryloxyhexyloxy)benzoates with Precocious Metamorphosis-Inducing Activity

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