INSECTICIDAL ACTION AND MITOCHONDRIAL UNCOUPLING ACTIVITY OF AC-303,630 AND RELATED HALOGENATED PYRROLES

被引:182
作者
BLACK, BC
HOLLINGWORTH, RM
AHAMMADSAHIB, KI
KUKEL, CD
DONOVAN, S
机构
[1] MICHIGAN STATE UNIV,PESTICIDE RES CTR,E LANSING,MI 48824
[2] AMER CYANAMID CO,PRINCETON,NJ 08543
关键词
D O I
10.1006/pest.1994.1064
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:115 / 128
页数:14
相关论文
共 19 条
[1]  
ADDOR RW, 1992, ACS SYM SER, V504, P283
[2]   MODE OF ACTION OF BULLATACIN - A POTENT ANTITUMOR AND PESTICIDAL ANNONACEOUS ACETOGENIN [J].
AHAMMADSAHIB, KI ;
HOLLINGWORTH, RM ;
MCGOVREN, JP ;
HUI, YH ;
MCLAUGHLIN, JL .
LIFE SCIENCES, 1993, 53 (14) :1113-1120
[3]   POLYSUBSTRATE MONOOXYGENASES AND OTHER XENOBIOTIC-METABOLIZING ENZYMES IN SUSCEPTIBLE AND RESISTANT COLORADO POTATO BEETLE [J].
AHAMMADSAHIB, KI ;
HOLLINGWORTH, RM ;
WHALON, ME ;
IOANNIDIS, PM ;
GRAFIUS, EJ .
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 1994, 49 (01) :1-12
[4]   INHIBITION OF RESPIRATION IN SUBMITOCHONDRIAL PARTICLES BY UNCOUPLERS OF OXIDATIVE PHOSPHORYLATION [J].
BEYER, RE ;
MACDONALD, JE .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1970, 137 (01) :38-+
[5]   LL-F42248-ALPHA, A NOVEL CHLORINATED PYRROLE ANTIBIOTIC [J].
CARTER, GT ;
NIETSCHE, JA ;
GOODMAN, JJ ;
TORREY, MJ ;
DUNNE, TS ;
BORDERS, DB ;
TESTA, RT .
JOURNAL OF ANTIBIOTICS, 1987, 40 (02) :233-236
[6]   EXCLUSION OF SUPERINFECTING HOMOLOGOUS VIRUS BY SINDBIS VIRUS-INFECTED AEDES-ALBOPICTUS (MOSQUITO) CELLS [J].
CONDREAY, LD ;
BROWN, DT .
JOURNAL OF VIROLOGY, 1986, 58 (01) :81-86
[7]   PYRROLOMYCIN-F1, PYRROLOMYCIN-F2A, PYRROLOMYCIN-F2B AND PYRROLOMYCIN-F3, NEW METABOLITES PRODUCED BY THE ADDITION OF BROMIDE TO THE FERMENTATION [J].
EZAKI, N ;
KOYAMA, M ;
KODAMA, Y ;
SHOMURA, T ;
TASHIRO, K ;
TSURUOKA, T ;
INOUYE, S ;
SAKAI, S .
JOURNAL OF ANTIBIOTICS, 1983, 36 (11) :1431-1438
[8]  
IMANKA H, 1965, J ANTIBIOT, V18, P207
[9]   CHEMISTRY AND TOXICOLOGY OF QUINOXALINE, ORGANOTIN, ORGANOFLUORINE, AND FORMAMIDINE ACARICIDES [J].
KNOWLES, CO .
ENVIRONMENTAL HEALTH PERSPECTIVES, 1976, 14 (APR) :93-102
[10]   STRUCTURE AND SYNTHESIS OF PYRROLOMYCIN-A, A CHLORINATED NITRO-PYRROLE ANTIBIOTIC [J].
KOYAMA, M ;
KODAMA, Y ;
TSURUOKA, T ;
EZAKI, N ;
NIWA, T ;
INOUYE, S .
JOURNAL OF ANTIBIOTICS, 1981, 34 (12) :1569-1576