Structure-Activity Studies of Insecticidal 2-Methoxy-1,3,2-oxazaphospholidine 2-Sulfides against Musca domestica and Tribolium castaneum

Akinori Hirashima, Yutaka Yoshii, Koichi Kumamoto, Kazuhiko Oyama, Morifusa Eto

研究成果: ジャーナルへの寄稿記事

14 引用 (Scopus)

抄録

2-Methoxy-5-substituted 1,3,2-oxazaphospholidine 2-sulfides (5-RMOS) were prepared by reacting methyl phosphorodichloridothionate with appropriate aminoalcohols which had been synthesized from the corresponding aldehydes with a) trimethylsilyl cyanide, b) sodium bisulfite-pottasium (sodium) cyanide and reacted with lithium aluminum hydride, or from c) phenacyl bromides (chlorides) via hexamethylenetetramine complex followed by acid-catalyzed hydrolysis and reduction with sodium borohydride. 2-Methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide (5-PMOS, II-l) was the most potent insecticide against Musca domestica by topical application (LD50 = 0.035 μg/fly), whereas 4-methylphenyl (11–45), 4-ethylphenyl (11–51), 4-isopropylphenyl (11–52) and 2,3-dimethoxyphenyl (II-57) analogs of 5-PMOS were the most potent in reducing the larval weight gain of Tribolium castaneum (I50 = 5.5, 3.7, 5.2 and 6.6 ppm). According to the quantitative structure-activity relationship (QSAR) analysis by Hansch and Fujita, steric nature of a substituent is important, and the smaller the substituent at the 5-phenyl of 5-RMOS, the more potent the insecticidal activity toward M. domestica, whereas toward T. castaneum, electronic nature was important, and the more resistant to hydrolysis the compounds, the more potent the activity on larval weight-gain inhibition of T. castaneum.

元の言語英語
ページ(範囲)539-551
ページ数13
ジャーナルJournal of Pesticide Science
15
発行部数4
DOI
出版物ステータス出版済み - 1 1 1990

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Tribolium
Houseflies
Tribolium castaneum
Musca domestica
Sulfides
sulfides
Weight Gain
Hydrolysis
Sodium Cyanide
cyanides
Methenamine
Quantitative Structure-Activity Relationship
Lethal Dose 50
Insecticides
weight gain
Aldehydes
sodium
Diptera
sodium bisulfite
quantitative structure-activity relationships

All Science Journal Classification (ASJC) codes

  • Insect Science
  • Health, Toxicology and Mutagenesis

これを引用

Structure-Activity Studies of Insecticidal 2-Methoxy-1,3,2-oxazaphospholidine 2-Sulfides against Musca domestica and Tribolium castaneum. / Hirashima, Akinori; Yoshii, Yutaka; Kumamoto, Koichi; Oyama, Kazuhiko; Eto, Morifusa.

:: Journal of Pesticide Science, 巻 15, 番号 4, 01.01.1990, p. 539-551.

研究成果: ジャーナルへの寄稿記事

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abstract = "2-Methoxy-5-substituted 1,3,2-oxazaphospholidine 2-sulfides (5-RMOS) were prepared by reacting methyl phosphorodichloridothionate with appropriate aminoalcohols which had been synthesized from the corresponding aldehydes with a) trimethylsilyl cyanide, b) sodium bisulfite-pottasium (sodium) cyanide and reacted with lithium aluminum hydride, or from c) phenacyl bromides (chlorides) via hexamethylenetetramine complex followed by acid-catalyzed hydrolysis and reduction with sodium borohydride. 2-Methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide (5-PMOS, II-l) was the most potent insecticide against Musca domestica by topical application (LD50 = 0.035 μg/fly), whereas 4-methylphenyl (11–45), 4-ethylphenyl (11–51), 4-isopropylphenyl (11–52) and 2,3-dimethoxyphenyl (II-57) analogs of 5-PMOS were the most potent in reducing the larval weight gain of Tribolium castaneum (I50 = 5.5, 3.7, 5.2 and 6.6 ppm). According to the quantitative structure-activity relationship (QSAR) analysis by Hansch and Fujita, steric nature of a substituent is important, and the smaller the substituent at the 5-phenyl of 5-RMOS, the more potent the insecticidal activity toward M. domestica, whereas toward T. castaneum, electronic nature was important, and the more resistant to hydrolysis the compounds, the more potent the activity on larval weight-gain inhibition of T. castaneum.",
author = "Akinori Hirashima and Yutaka Yoshii and Koichi Kumamoto and Kazuhiko Oyama and Morifusa Eto",
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T1 - Structure-Activity Studies of Insecticidal 2-Methoxy-1,3,2-oxazaphospholidine 2-Sulfides against Musca domestica and Tribolium castaneum

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N2 - 2-Methoxy-5-substituted 1,3,2-oxazaphospholidine 2-sulfides (5-RMOS) were prepared by reacting methyl phosphorodichloridothionate with appropriate aminoalcohols which had been synthesized from the corresponding aldehydes with a) trimethylsilyl cyanide, b) sodium bisulfite-pottasium (sodium) cyanide and reacted with lithium aluminum hydride, or from c) phenacyl bromides (chlorides) via hexamethylenetetramine complex followed by acid-catalyzed hydrolysis and reduction with sodium borohydride. 2-Methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide (5-PMOS, II-l) was the most potent insecticide against Musca domestica by topical application (LD50 = 0.035 μg/fly), whereas 4-methylphenyl (11–45), 4-ethylphenyl (11–51), 4-isopropylphenyl (11–52) and 2,3-dimethoxyphenyl (II-57) analogs of 5-PMOS were the most potent in reducing the larval weight gain of Tribolium castaneum (I50 = 5.5, 3.7, 5.2 and 6.6 ppm). According to the quantitative structure-activity relationship (QSAR) analysis by Hansch and Fujita, steric nature of a substituent is important, and the smaller the substituent at the 5-phenyl of 5-RMOS, the more potent the insecticidal activity toward M. domestica, whereas toward T. castaneum, electronic nature was important, and the more resistant to hydrolysis the compounds, the more potent the activity on larval weight-gain inhibition of T. castaneum.

AB - 2-Methoxy-5-substituted 1,3,2-oxazaphospholidine 2-sulfides (5-RMOS) were prepared by reacting methyl phosphorodichloridothionate with appropriate aminoalcohols which had been synthesized from the corresponding aldehydes with a) trimethylsilyl cyanide, b) sodium bisulfite-pottasium (sodium) cyanide and reacted with lithium aluminum hydride, or from c) phenacyl bromides (chlorides) via hexamethylenetetramine complex followed by acid-catalyzed hydrolysis and reduction with sodium borohydride. 2-Methoxy-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide (5-PMOS, II-l) was the most potent insecticide against Musca domestica by topical application (LD50 = 0.035 μg/fly), whereas 4-methylphenyl (11–45), 4-ethylphenyl (11–51), 4-isopropylphenyl (11–52) and 2,3-dimethoxyphenyl (II-57) analogs of 5-PMOS were the most potent in reducing the larval weight gain of Tribolium castaneum (I50 = 5.5, 3.7, 5.2 and 6.6 ppm). According to the quantitative structure-activity relationship (QSAR) analysis by Hansch and Fujita, steric nature of a substituent is important, and the smaller the substituent at the 5-phenyl of 5-RMOS, the more potent the insecticidal activity toward M. domestica, whereas toward T. castaneum, electronic nature was important, and the more resistant to hydrolysis the compounds, the more potent the activity on larval weight-gain inhibition of T. castaneum.

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