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当前位置: 首页 > 文章 > O-乙基O-苯基S-(β-乙氧基)乙基硫代磷酸酯的旋光异构体生物活性的立体特异性 昆虫学报 1983,26 (1) 10-16
Position: Home > Articles > STEREOSPECIFICITY IN BIOLOGICAL ACTIVITIES OF THE OPTICAL ISOMERS OF O-ETHYL O-PHENYL S-(2-ETHYLOXY) ETHYL PHOSPHOROTHIOATE (4251) Acta Entomologica Sinica 1983,26 (1) 10-16

O-乙基O-苯基S-(β-乙氧基)乙基硫代磷酸酯的旋光异构体生物活性的立体特异性

作  者：
尚稚珍;张壬午;邹永华;王银淑;吴玉霞;李英;于维强;唐除痴
单  位：
南开大学元素有机化学研究所
摘  要：
在有机磷杀虫剂中,当磷原子上所连接的三个基团互不相同时,磷原子具有不对称性,存在着旋光异构体。近年来的研究表明(大川秀郎,1976;Fukuto,1979;Ohkawa等,1976、1978;Nomeir,1979;Yoshikawa,1980),这些旋光异构体在酶系反应、生物活性、对哺乳动物的毒性以及在生物体内的代谢等许多方面都有明显的差别。这种立体特
译  名：
STEREOSPECIFICITY IN BIOLOGICAL ACTIVITIES OF THE OPTICAL ISOMERS OF O-ETHYL O-PHENYL S-(2-ETHYLOXY) ETHYL PHOSPHOROTHIOATE (4251)
作  者：
SHANG CHIH-CHEH ZHANG EEN-WU ZHOU YONG-HAU WANG YIH-SHU UU YU-XIA LI YING Yu FEI-QIANG AND TANG CHU-CHI (The Institute of Elemento-Organic Chemistry Nankai University, Tianjin)
摘  要：
This report concerns the differential toxieity of the optical isomers of 4251 towards different insects. The (+)-isomer of 4251 is more effective as an insecticide to rice stem borer (Chilo supperssalis) larvae, corn borer (Ostrinia furnacalis) larvae, houseflies (Musca domestica) adults, and mosquito (Culex pipiens) larvae than the (-)-isomer. The (+)-isomer is 6-to 9-fold more toxic to rice stem borer larvae and 9-to 14-fold more toxic to corn borer than its enantiomer. Also, the three forms of 4251 showed a marked difference in toxieity to rice plants through systemic activity.The different results of stereospecificty in cholinesterase inhibitions of the optical isomers of 4251 to the cholinesterases of rice stem borer larvae, human serum, horse serum and mouse brains were also obtained. It is interesting to note that the inhibition of the (-)-isomer to rice stem borer CHE in vitro is 7-to 8-fold more than that of the (+) -isomer. In contrast, if the insects were treated with the drug in advance, I50 of the (+)-isomer is 7-to 14-fold more than that of the (-)-isomer. It is apparent that the (-)-isomer has rather high mammlian toxieity.The activity of the racemic compound was close to the mean of the two resolved isomers or close to that of the stronger one. Therefore the (+)-isomer of 4251 appears to be a more appropriate insecticide than the racemic compound, since its property combines high toxieity to insects and low mammalian toxieity.

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