Synthesis and anti-juvenile hormone activity of ethyl 4-(2-(6-methyl-3-pyridyloxy)alkyloxy)benzoates
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 a...
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| Veröffentlicht in: | Journal of pesticide science (2003) 2005-08, Vol.30 (3) |
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| creator | Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture) Furuta, K Shirahashi, H Hong, S Shiotsuki, T Kuwano, E |
| description | 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(+)- and 5S(-)-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. |
| format | Article |
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Faculty of Agriculture) ; Furuta, K ; Shirahashi, H ; Hong, S ; Shiotsuki, T ; Kuwano, E</creator><creatorcontrib>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture) ; Furuta, K ; Shirahashi, H ; Hong, S ; Shiotsuki, T ; Kuwano, E</creatorcontrib><description>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(+)- and 5S(-)-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.</description><identifier>ISSN: 1348-589X</identifier><identifier>EISSN: 1349-0923</identifier><language>eng</language><subject>ANTAGONISTAS DE LAS HORMONAS ; ANTAGONISTE D'HORMONE ; BOMBYX MORI ; CHEMICAL SYNTHESIS ; COMPOSE HETEROCYCLIQUE ; COMPUESTOS HETEROCICLICOS ; HETEROCYCLIC COMPOUNDS ; HORMONAS JUVENILES ; HORMONE ANTAGONISTS ; HORMONE JUVENILE ; JUVENILE HORMONES ; MECANISMOS DE ACCION ; MODE D'ACTION ; MODE OF ACTION ; SINTESIS QUIMICA ; SYNTHESE CHIMIQUE</subject><ispartof>Journal of pesticide science (2003), 2005-08, Vol.30 (3)</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781</link.rule.ids></links><search><creatorcontrib>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture)</creatorcontrib><creatorcontrib>Furuta, K</creatorcontrib><creatorcontrib>Shirahashi, H</creatorcontrib><creatorcontrib>Hong, S</creatorcontrib><creatorcontrib>Shiotsuki, T</creatorcontrib><creatorcontrib>Kuwano, E</creatorcontrib><title>Synthesis and anti-juvenile hormone activity of ethyl 4-(2-(6-methyl-3-pyridyloxy)alkyloxy)benzoates</title><title>Journal of pesticide science (2003)</title><description>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(+)- and 5S(-)-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.</description><subject>ANTAGONISTAS DE LAS HORMONAS</subject><subject>ANTAGONISTE D'HORMONE</subject><subject>BOMBYX MORI</subject><subject>CHEMICAL SYNTHESIS</subject><subject>COMPOSE HETEROCYCLIQUE</subject><subject>COMPUESTOS HETEROCICLICOS</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HORMONAS JUVENILES</subject><subject>HORMONE ANTAGONISTS</subject><subject>HORMONE JUVENILE</subject><subject>JUVENILE HORMONES</subject><subject>MECANISMOS DE ACCION</subject><subject>MODE D'ACTION</subject><subject>MODE OF ACTION</subject><subject>SINTESIS QUIMICA</subject><subject>SYNTHESE CHIMIQUE</subject><issn>1348-589X</issn><issn>1349-0923</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNqFiUEPwTAYhhshseAnSHqcw5d8Vrb1LEScJBzcpKyz0rWylqhfT3B3ePI-b54WicZswgF5wtofz2Ga812XDJw7I-I4YxnnaUSKTTC-kk45Kkzxxis43-7SKC1pZZvaGknF0au78oHakkpfBU0nECcQp1B_LjC4hkYVQdtHGAl9-cpBmqcVXro-6ZRCOzn4bY8MF_PtbAmlsHtxapTbr9YJYorI8imyf_0FQq5CIw</recordid><startdate>200508</startdate><enddate>200508</enddate><creator>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture)</creator><creator>Furuta, K</creator><creator>Shirahashi, H</creator><creator>Hong, S</creator><creator>Shiotsuki, T</creator><creator>Kuwano, E</creator><scope>FBQ</scope></search><sort><creationdate>200508</creationdate><title>Synthesis and anti-juvenile hormone activity of ethyl 4-(2-(6-methyl-3-pyridyloxy)alkyloxy)benzoates</title><author>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture) ; Furuta, K ; Shirahashi, H ; Hong, S ; Shiotsuki, T ; Kuwano, E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-fao_agris_JP20060038503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>ANTAGONISTAS DE LAS HORMONAS</topic><topic>ANTAGONISTE D'HORMONE</topic><topic>BOMBYX MORI</topic><topic>CHEMICAL SYNTHESIS</topic><topic>COMPOSE HETEROCYCLIQUE</topic><topic>COMPUESTOS HETEROCICLICOS</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HORMONAS JUVENILES</topic><topic>HORMONE ANTAGONISTS</topic><topic>HORMONE JUVENILE</topic><topic>JUVENILE HORMONES</topic><topic>MECANISMOS DE ACCION</topic><topic>MODE D'ACTION</topic><topic>MODE OF ACTION</topic><topic>SINTESIS QUIMICA</topic><topic>SYNTHESE CHIMIQUE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture)</creatorcontrib><creatorcontrib>Furuta, K</creatorcontrib><creatorcontrib>Shirahashi, H</creatorcontrib><creatorcontrib>Hong, S</creatorcontrib><creatorcontrib>Shiotsuki, T</creatorcontrib><creatorcontrib>Kuwano, E</creatorcontrib><collection>AGRIS</collection><jtitle>Journal of pesticide science (2003)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fujita, N.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture)</au><au>Furuta, K</au><au>Shirahashi, H</au><au>Hong, S</au><au>Shiotsuki, T</au><au>Kuwano, E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and anti-juvenile hormone activity of ethyl 4-(2-(6-methyl-3-pyridyloxy)alkyloxy)benzoates</atitle><jtitle>Journal of pesticide science (2003)</jtitle><date>2005-08</date><risdate>2005</risdate><volume>30</volume><issue>3</issue><issn>1348-589X</issn><eissn>1349-0923</eissn><abstract>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(+)- and 5S(-)-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.</abstract></addata></record> |
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| ispartof | Journal of pesticide science (2003), 2005-08, Vol.30 (3) |
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| language | eng |
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| source | J-STAGE Free; Freely Accessible Japanese Titles; AgriKnowledge（アグリナレッジ）AGROLib |
| subjects | ANTAGONISTAS DE LAS HORMONAS ANTAGONISTE D'HORMONE BOMBYX MORI CHEMICAL SYNTHESIS COMPOSE HETEROCYCLIQUE COMPUESTOS HETEROCICLICOS HETEROCYCLIC COMPOUNDS HORMONAS JUVENILES HORMONE ANTAGONISTS HORMONE JUVENILE JUVENILE HORMONES MECANISMOS DE ACCION MODE D'ACTION MODE OF ACTION SINTESIS QUIMICA SYNTHESE CHIMIQUE |
| title | Synthesis and anti-juvenile hormone activity of ethyl 4-(2-(6-methyl-3-pyridyloxy)alkyloxy)benzoates |
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