Detail of "2012-74-0"

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Recent progress in syntheses of the new and most potent pyrethroids

Recent progress in syntheses of the new and most potent pyrethroids. Itaya, Nobushige; Matsuo, Takashi; Ohno, Nobuo; Mizutani, Toshio; Fujita, Fumio; Yoshioka, Hirosuke (Pestic. Div., Sumitomo Chem. Co. Ltd. 63710-58-7 is just another one chemical used in this study., Hyogo, Japan). ACS Symp. Ser., 42(Synth. Pyrethroids, Symp.), 45-54 (English) 1977. CODEN: ACSMC8. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemicals) Section cross-reference(s): 24, 25 The prepn. of the acid moieties of NRDC-143 and NRDC-149, cis- [59042-49-8] and trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid [59042-50-1], and the acid moiety of S-5602,.alpha.-(4-chlorophenyl)isovalaric acid [2012-74-0], is described. Cis-NRDC-143 (I) [61949-76-6] and cis-NRDC-149 were twice as toxic to houseflies and German cockroaches as the respective trans isomers. Other aspects of the prepn. of pyrethroid insecticides are discussed. .

The metabolism of fenvalerate in plants: the conjugation of the acid moiety

The metabolism of fenvalerate in plants: the conjugation of the acid moiety. Mikami, Nobuyoshi; Wakabayashi, Noriko; Yamada, Hirohiko; Miyamoto, Junshi (Takarazuka Res. Cent., Sumitomo Chem. Co. Ltd., Takarazuka 665, Japan). Pestic. Sci., 16(1), 46-58 (English) 1985. CODEN: PSSCBG. ISSN: 0031-613X. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) The metab. of fenvalerate [51630-58-1] and of its most insecticidal isomer (S)-a-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate [66230-04-4], was examd. in cabbage plants grown and treated under lab. conditions with [14C]chlorophenyl- and [ring-14C]benzyl-labeled prepns. of the 2 compds. Both insecticides disappeared from the treated leaves with similar half-lives of approx. 12-14 days; they underwent ester cleavage to a significant extent, together with some hydroxylation at the 2- or 4-position of the phenoxy ring, and hydrolysis of the nitrile group to amide and carboxyl groups. Most of the carboxylic acids and phenols thus produced occurred as glycoside conjugates. In sep. expts., the uptake and metab. of 2-(4-chlorophenyl)-3-methylbutyric acid (I) [2012-74-0], the acidic half of the fenvalerate mol., were examd. in the lab., using abscised leaves of kidney bean, cabbage, cotton, cucumber and tomato plants. I was readily converted, mainly into glucose and 6-O-malonylglucose esters in kidney bean, cabbage and cucumber plants, into glucosylxylose, sophorose, and gentiobiose esters in cotton, and into 2 types of triglucose esters with differing isomerism in tomato. One of the acetyl derivs. of the trisaccharide conjugates was identical with the synthetic deca-acetyl deriv. of the [1?6]-triglucose ester.