EPOXY AND HYDROXY DERIVATIVES OF (S)-BIOALLETHRIN AND PYRETHRINS-I AND PYRETHRINS-II - SYNTHESIS AND METABOLISM

被引：10

作者：

ANDO, T ^{[1
]}

TOIA, RF ^{[1
]}

CASIDA, JE ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT ENTOMOL SCI,PESTICIDE CHEM & TOXICOL LAB,BERKELEY,CA 94720

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 1991年 / 39卷 / 03期

关键词：

D O I：

10.1021/jf00003a034

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

The 2-methylpropenyl group of (S)-bioallethrin (A) and the pentadienyl group of pyrethrin II (PII) are selectively oxidized by m-chloroperoxybenzoic acid in dichloromethane to yield the 7,8-epoxide (1) from A and a mixture of the 8',9'- and 10',11'-epoxides (7 and 8) from PII. These epoxides are hydrated in aqueous acid to the corresponding diols and other hydroxy derivatives produced by opening of the cyclopropyl ring or migration of the adjacent double bond. The epoxy and hydroxy derivatives are identified by two-dimensional NMR techniques. Mouse liver enzymes do not detectably hydrate epoxide 1 but quickly hydrate epoxides 7 and 8 without migration of the double bond. HPLC analyses of the microsomal metabolites of pyrethrins I and II identify the 10',11'-diols as major metabolites and the 8',9'-diols as minor products.

引用

页码：606 / 611

页数：6

共 10 条

[1] COMPARATIVE METABOLISM OF CECROPIA JUVENILE-HORMONE [J].

AJAMI, AM ;

RIDDIFOR.LM .

JOURNAL OF INSECT PHYSIOLOGY, 1973, 19 (03) :635-645

[2] EPOXYCHRYSANTHEMATES - 2-DIMENSIONAL NMR ANALYSES AND STEREOCHEMICAL ASSIGNMENTS [J].

ANDO, T ;

JACOBSEN, NE ;

TOIA, RF ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (03) :600-605

[3] PYRETHROID METABOLISM - MICROSOMAL OXIDASE METABOLITES OF (S)-BIOALLETHRIN AND THE 6 NATURAL PYRETHRINS [J].

CLASS, TJ ;

ANDO, T ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1990, 38 (02) :529-537

[4] METABOLIC FATE OF PYRETHRIN I, PYRETHRIN II, AND ALLETHRIN ADMINISTERED ORALLY TO RATS [J].

ELLIOTT, M ;

CASIDA, JE ;

KIMMEL, EC ;

JANES, NF .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1972, 20 (02) :300-&

[5]

ELLIOTT M, 1971, INSECTICIDES, P141

[6] MAMMALIAN METABOLISM AND ENVIRONMENTAL DEGRADATION OF JUVENOID 1-(4'-ETHYLPHENOXY)-3,7-DIMETHYL-6,7-EPOXY-TRANS-2-OCTENE AND RELATED COMPOUNDS [J].

GILL, SS ;

HAMMOCK, BD ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1974, 22 (03) :386-395

[7] METABOLITES OF THE PROTOTYPE INSECTICIDE (2E,4E)-N-ISOBUTYL-6-PHENYLHEXA-2,4-DIENAMIDE .2. FORMATION IN MOUSE AND RAT-LIVER MICROSOMAL SYSTEMS, RAT HEPATOCYTES, AND HOUSEFLIES [J].

JOHNSTON, JJ ;

HORSHAM, MA ;

CLASS, TJ ;

CASIDA, JE .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (03) :781-786

[8]

MATSUI M, 1963, AGR BIOL CHEM TOKYO, V27, P554

[9] EPOXYCHRYSANTHEMIC ACID AS AN INTERMEDIATE IN METABOLIC DECARBOXYLATION OF CHRYSANTHEMATE INSECTICIDES [J].

SMITH, IH ;

CASIDA, JE .

TETRAHEDRON LETTERS, 1981, 22 (03) :203-206

[10] METABOLISM OF JUVENILE-HORMONE ANALOG METHYL FARNESOATE 10,11-EPOXIDE IN TWO INSECT SPECIES [J].

WHITE, AF .

LIFE SCIENCES PT-2 BIOCHEMISTRY GENERAL AND MOLECULAR BIOLOGY, 1972, 11 (04) :201-&

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