EFFECTS OF ANTI-ECDYSTEROID AZOLE ANALOGS OF METYRAPONE ON THE LARVAL DEVELOPMENT OF THE FLESHFLY, NEOBELLIERIA-BULLATA

被引:15
作者
BELAI, I
DARVAS, B
BAUER, K
ELDIN, MHT
机构
[1] Plant Protection Institute, Hungarian Academy of Sciences, Budapest, H-1525
来源
PESTICIDE SCIENCE | 1995年 / 44卷 / 03期
关键词
METYRAPONE; ANTI-ECDYSTEROID; NEOBELLIERIA BULLATA; AZOLE;
D O I
10.1002/ps.2780440304
中图分类号
S3 [农学(农艺学)];
学科分类号
0901 ;
摘要
Based on our previous finding that PIM (phenyl-imidazolyl-metyrapon; 2-(1-imidazolyl)-2-methyl-1-phenylpropan-1-one, 1) is a strong inhibitor of ecdysone 20-monooxygenase (IC50 = 7.89 x 10(-7) M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4-triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p-methoxy (LC(50) = 49 mg kg(-1) in diet) or p-chloro (LC(50) = 97 mg kg(-1)) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC(50) = 561 mg kg(-1)) and PIM (LC(50) = 148 mg kg(-1)). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.
引用
收藏
页码:225 / 232
页数:8
相关论文
共 32 条
  • [1] A TEST FOR BOTTLENECKS IN THE VIBRATIONAL-RELAXATION OF CH3CL AND CH3BR BY AR
    BECK, KM
    GORDON, RJ
    [J]. LASER CHEMISTRY, 1988, 9 (1-3) : 47 - 62
  • [2] DISRUPTIVE DEVELOPMENTAL EFFECTS OF BENZYL-1,3-BENZODIOXOLE DERIVATIVES ON UNPARASITIZED AND PARASITIZED MANDUCA-SEXTA LARVAE
    BECKAGE, NE
    TEMPLETON, TJ
    STIRLING, BA
    NIELSEN, BD
    [J]. JOURNAL OF INSECT PHYSIOLOGY, 1987, 33 (09) : 603 - 611
  • [3] INHIBITION OF INSECT CYTOCHROME-P-450 BY SOME METYRAPONE ANALOGS AND COMPOUNDS CONTAINING A CYCLOPROPYLAMINE MOIETY AND THEIR EVALUATION AS INHIBITORS OF JUVENILE-HORMONE BIOSYNTHESIS
    BELAI, I
    MATOLCSY, G
    FARNSWORTH, DE
    FEYEREISEN, R
    [J]. PESTICIDE SCIENCE, 1988, 24 (03): : 205 - 219
  • [4] EVIDENCE FOR AN ALPHA-ECDYSONE - CYTOCHROME-P-450 MIXED-FUNCTION OXIDASE IN INSECT FAT-BODY MITOCHONDRIA
    BOLLENBACHER, WE
    SMITH, SL
    WIELGUS, JJ
    GILBERT, LI
    [J]. NATURE, 1977, 268 (5621) : 660 - 663
  • [5] NEW AMPHENONE ANALOGS AS ADRENOCORTICAL INHIBITORS
    CHART, JJ
    SHEPPARD, H
    ALLEN, MJ
    BENCZE, WL
    GAUNT, R
    [J]. EXPERIENTIA, 1958, 14 (04): : 151 - 152
  • [6] FUNGICIDAL ACTIVITY OF A SERIES OF 1-SUBSTITUTED-1-ARYL-2-TRIAZOL-1-YL-ETHANOLS
    CHOLLET, JF
    BONNEMAIN, JL
    MIGINIAC, L
    ROHR, O
    [J]. PESTICIDE SCIENCE, 1990, 29 (04): : 427 - 435
  • [7] LETHAL DISTURBANCES IN LARVAL DEVELOPMENT OF NEOBELLIERIA-BULLATA CAUSED BY METYRAPONE DERIVATIVES
    DARVAS, B
    BELAI, I
    FONAGY, A
    KULCSAR, P
    ELDIN, MHT
    [J]. PESTICIDE SCIENCE, 1991, 32 (02): : 133 - 139
  • [8] LETHAL DISTURBANCES IN THE PREECDYSIAL PROCESSES OF SARCOPHAGA-BULLATA CAUSED BY IMIDAZOLE CONTAINING KK-42
    DARVAS, B
    KUWANO, E
    ETO, M
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (03): : 859 - 861
  • [9] CYTOCHROME-P-450 INDUCERS AND INHIBITORS INTERFERING WITH ECDYSONE-20-MONOOXYGENASES AND THEIR ACTIVITIES DURING POSTEMBRYONIC DEVELOPMENT OF NEOBELLIERIA-BULLATA PARKER
    DARVAS, B
    REES, HH
    HOGGARD, N
    ELDIN, MHT
    KUWANO, E
    BELAI, I
    TIMAR, T
    [J]. PESTICIDE SCIENCE, 1992, 36 (02): : 135 - 142
  • [10] DEVELOPMENTAL DISTURBANCES IN DIFFERENT INSECT ORDERS CAUSED BY AN ECDYSTEROID AGONIST, RH 5849
    DARVAS, B
    POLGAR, L
    ELDIN, MHT
    EROSS, K
    WING, KD
    [J]. JOURNAL OF ECONOMIC ENTOMOLOGY, 1992, 85 (06) : 2107 - 2112