SCIE
KCI등재
SCOPUS
모조(模造) 환경조건하에서의 치환 Diphenly Ether 제초제(除草劑)의 광분해에 관한 연구 = Solution Phase Photolyses of Substituted Diphenyl Ether Herbicides under Simulated Environmental Conditions
저자
이재구 (충북대학 농화학과)
발행기관
학술지명
Applied Biological Chemistry (Appl Biol Chem)(Applied Biological Chemistry)
권호사항
발행연도
1974
작성언어
English
KDC
470
등재정보
SCIE,KCI등재,SCOPUS
자료형태
학술저널
발행기관 URL
수록면
149-176(28쪽)
제공처
소장기관
Eight substituted diphenyl ether herbicides and some of their photoproducts were studied in terms of solution phase photolysis under simulated environmental conditions by using a Rayonet photochemical reactor. The test compounds absorbed sufficient light energy at the wavelength of 300 ㎚ to undergo various photoreactions. All the photoproducts were confirmed by means of tlc, glc, ir, ms, and/or nmr spectrometry. The results obtained are summarized as follows:
Solution phase photolysis of C-6989:
An exceedingly large amount of p-nitrophenol formed strongly indicates the readiness of the ether linkage cleavage of this compound as the main reaction in all solvents used. Photoreduction of nitro to amino groups) and photooxidation of trifluoromethyl to carboxyl group wets: recognized as minor reactions.
Aqueous photolysis of p-nitrophenol:
Quinone(0.28%), hydroquinone (0.66%), and p-aminophenol (0.42%) were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. The mechanisms of formation of these products were proposed to be the nitro-nitrite rearrangement via n→π^* excitation and the photoreduction through hydrogen abstractions by radicals, respectively.
Solution phase photolysis of Nitrofen:
Photochemical reduction leading to the p-amino derivative was the main reaction in n-hexane. In aqueous solution, the photoreduction of nitro to amino group and hydroxylation predominated over the ether linkage cleavage. Nucleophilic displacement of the nitro group by hydroxide ion and replacement of chlorine substituents by hydroxyl group or, to a lesser extent, hydrogen were also observed as minor reactoins.
Solution phase photolysis of MO-338:
Photoreduction of the vitro to amino group was marked in the n-hexane solution photolysis. In the aqueous solution, photoreduction of the vitro substituent and hydroxylation were the main reactions with replacement of chlorine substituents by the hydroxyl group and hydrogen, and cleavage of the ether linkage as minor reactions.
Photolyses of MC-4379, MC-3761, MC-5127, MC-6063, and MC-7181 in n-hexane and cyclohexane:
Photoreduction of the vitro group leading to the corresponding amino derivative and replacement of one of the halogen substituents by hydrogen from the solvent used were the key reactions in each compound.
Aqueous photolysis of MC-4379:
Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, hydroxylation, and replacement of the nitro by hydroxy group were prominent with photoreduction and dechlorination as minor reactions.
Aqueous photolysis of MC-3761:
Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, and photoreduction followed by hydroxylation were the main reactions.
Aqueous photolysis of MC-5127:
Replacement of carboxyethyl by hydrogen was predominant with ether linkage cleavage, photoreduction, and dechlorination as minor reactions. It was obvious that the decarboxyethylation proceeded more readily than decarboxymethylation occurring in the other compounds.
Aqueous photolysis of MC-6063:
Cleavage of the ether linkage and photodechlorination were the main reactions.
Aqueous photolysis of MC-7181:
Replacement of the carboxymethyl group by hydrogen and monodechlorination were the remarkable reactions. Cleavage of the ether linkage and hydroxylation were thought to be the minor reactions.
Aqueous photolysis of 3-carboxymethyl-4-nitrophenol:
The photo-induced Fries rearrangement common to aromatic esters did not appear to occur in the carboxymethyl group of this type of compound. Conversion of nitro to nitroso group was the main reaction.
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