INSECTICIDAL ACTION AND MITOCHONDRIAL UNCOUPLING ACTIVITY OF AC-303,630 AND RELATED HALOGENATED PYRROLES
INSECTICIDAL ACTION AND MITOCHONDRIAL UNCOUPLING ACTIVITY OF AC-303,630 AND RELATED HALOGENATED PYRROLES
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DOI：
10.1006/pest.1994.1064
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发表时间：
1994-10-01
影响因子：
4.7
通讯作者：
DONOVAN, S
中科院分区：
文献类型：
--
作者：
BLACK, BC;HOLLINGWORTH, RM;DONOVAN, S
研究了实验性杀虫剂/杀螨剂 AC-303,630（(4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)吡咯-3-甲腈）；Pirate, Stalker，CAS 号[122453-73-0]）及其卤代吡咯类似物的作用方式。 AC-303,630 导致德国小蠊的呼吸活动大大增加，但作为针对分离线粒体的解偶联剂实际上没有活性。然而，其 N-脱烷基类似物 AC-303,268 是一种有效的解偶联剂，在 10-100 nM 范围内对大鼠、鱼类和昆虫线粒体具有显着活性。通过用单加氧酶抑制剂胡椒基丁醚进行预处理，可以拮抗昆虫的呼吸刺激和毒性。对一系列卤代吡咯的结构-活性研究也支持解偶联和毒性之间的关系。基于这些结果得出结论，AC-303,630是一种通过氧化去除N-乙氧基甲基而被激活的杀虫剂。这会释放出一种亲脂性弱酸性吡咯代谢物，通过线粒体解偶联发挥毒性。 (C) 1994 年学术出版社
The mode of action of the experimental insecticide/acaricide, AC-303,630 ((4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile); Pirate, Stalker, CAS No. [122453-73-0]), and its halogenated pyrrole analogs was studied. AC-303,630 caused greatly increased respiratory activity in German cockroaches but was virtually inactive as an uncoupler against isolated mitochondria. However, its N-dealkylated analog, AC-303,268, was a potent uncoupler with notable activity in the range of 10-100 nM against rat, fish, and insect mitochondria. Both respiratory stimulation and toxicity were antagonized in insects by pretreatment with the monooxygenase inhibitor piperonyl butoxide. Structure-activity studies with a range of halogenated pyrroles also supported a relationship between uncoupling and toxicity. Based on these results it is concluded that AC-303,630 is a propesticide that is activated by the oxidative removal of the N-ethoxymethyl group. This releases a lipophilic, weakly acidic pyrrole metabolite which exerts its toxicity through mitochondrial uncoupling. (C) 1994 Academic Press, Inc.