INSECTICIDAL ACTIVITY OF NEW FLUORINATED PYRETHROIDS AND THEIR STABILITY TOWARD CHEMICAL OXIDATION AND PHOTOREACTION

被引:10
作者
ANDO, T [1 ]
KOSEKI, N [1 ]
YASUHARA, I [1 ]
KASUGA, K [1 ]
MATSUO, N [1 ]
ISHIWATARI, T [1 ]
机构
[1] SUMITOMO CHEM CO LTD,TAKARAZUKA RES CTR,TAKARAZUKA,HYOGO 665,JAPAN
来源
PESTICIDE SCIENCE | 1994年 / 40卷 / 04期
关键词
D O I
10.1002/ps.2780400409
中图分类号
S3 [农学(农艺学)];
学科分类号
0901 ;
摘要
The insecticidal activity of several new fluorinated pyrethroids was measured using houseflies untreated and treated with piperonyl butoxide (PB). 10,10-Difluorophenothrin and 10,10-difluoroallethrin, which include fluorine atoms at a position most easily attacked by mixed function oxidases (mfo) in the acid moiety, showed smaller topical LD50 values on the PB-untreated flies than the parent insecticides but rather large values on the PB-treated flies, suggesting that the introduction of fluorine prevents metabolic oxidation, although it has a negative effect on the interaction with a target site. Monofluorinated analogues of phenothrin, in which the structure of chrysanthemic acid was rearranged, still had moderate insecticidal activity, but flies were scarcely killed by 7'-fluoroallethrin into which fluorine was introduced at a position most easily oxidized by mfo in the alcohol moiety. Competitive oxidation of the fluorinated derivatives and the parent compounds showed that fluorine at both the 10- and 7'-positions stabilizes the alkenyl side-chains of the pyrethroids against selenium dioxide and m-chloroperoxybenzoic acid. Photochemical studies with 10,10-difluorophenothrin indicated that the photo-instability of the cyclopropanecarboxylic part could not be improved by this modification.
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页码:307 / 312
页数:6
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