- Preparation method and application of 2-6 -diethyl -4 methylphenylpropionic acid diester
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The invention belongs to the technical field of synthesis of an oxazoline intermediate, and particularly provides a preparation method of 2-6 -diethyl -4 methylphenylpropionic acid diester, in particular to an inorganic acid with 2, 6 -diethyl -4 methylph
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Paragraph 0055-0059
(2021/09/01)
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- NOVEL PROCESS FOR PREPARATION OF KEY INTERMEDIATE OF PINOXADEN
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The present invention relates to a novel process for preparation of compounds of formula (I) used in the synthesis of Pinoxaden. The intermediate is a substituted phenyl malonic esters of formula (I), where R is C1-C4 alkyl, straight or branched chain.
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- Method for preparing pinoxaden intermediate through micro-channel
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The invention relates to a method for preparing a pinoxaden intermediate through a micro-channel. Intermediates 2, 6-diethyl-4-methyl phenyl diethyl malonate and [1, 4, 5] oxadiazepane dihydrobromideare prepared from 2, 6-diethyl-4-methylbenzenemalononitr
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Paragraph 0011; 0047-0049; 0054-0056; 0061-0063; 0069; 0070
(2020/08/02)
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- Preparation method of pinoxaden
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The invention relates to the field of organic synthesis, in particular to a synthesis method of pinoxaden. The synthesis method comprises the following steps that under catalysis of copper chloride orcuprous chloride, 4-methyl-2,6-diethyl aniline reacts with 1,1-dichloroethylene and nitrous acid ester to generate a compound 1; the compound 1 reacts with sodium alcoholate, and a reaction product is subjected to acidic hydrolysis to obtain a compound 2; the compound 2 reacts with diester carbonate and strong base to obtain an intermediate 3; after diethylene glycol dimethanesulfonate reacts with hydrazine hydrate, salifying with hydrochloric acid is conducted to obtain an intermediate 4; the intermediate 3 and the intermediate 4 are subjected to ring forming under the effect of base to obtain a compound 5; and the compound 5 and pivaloyl chloride react under the effect of the base or base/DMAP to obtain the pinoxaden. The synthesis method of the pinoxaden does not use expensive or toxiccatalysts, does not need to adopt a protection/deprotection strategy, and has the characteristics of low cost and high atomic economy.
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Paragraph 0041; 0044; 0055; 0058
(2019/12/25)
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- Preparation method of intermediate compound 2, 6 - diethyl -4 - methylbenzene malonate (by machine translation)
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The method has the advantages of mild reaction conditions, wide raw material source and short synthetic route, and CuI and L - proline are used as a catalyst system, and 2, 6 -diethyl -4 -4 - methyliodobenzene and malonic acid diester are subjected to cou
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Paragraph 0052; 0055; 0056; 0059
(2019/10/01)
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- Phenyl pyrazoline compound with bioactivity and preparation method and application thereof
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The invention discloses a phenyl pyrazoline compound shown as a formula (I) and a preparation method and application thereof. R, R1, R2, R3 and R4 in the formula are defined in the specification. Thecompound shown as the formula (I) has herbicidal, insecticidal/acaricidal or bactericidal bioactivity and has high activity especially on weeds.
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Paragraph 0059; 0060; 0063
(2019/08/26)
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- Synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate
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The invention discloses a synthesis method of 2-(2, 6-diethyl-4-methyl benzene) diethyl malonate. The synthesis method comprises the following steps: in the presence of a catalyst, performing a reaction on 2, 6-diethyl-4-methylaniline and isoamyl nitrite,
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Paragraph 0029-0072
(2019/02/26)
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- Preparation method of pinoxaden
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The invention relates to a preparation method of pinoxaden. The preparation method comprises the following steps: carrying out sandmeyer reaction on 2,6-diethyl-4-methylaniline to obtain 2,6-diethyl-4-methylbromobenzene; then coupling the 2,6-diethyl-4-methylbromobenzene with malononitrile under the catalysis of copper iodide and the like to obtain 2,6-di-ethyl-4-methylphenyl malononitrile; finally, hydrolyzing in a hydrogen peroxide solution to obtain 2,6-diethyl-4-methylphenyl malonamide; afterwards, reacting the 2,6-diethyl-4-methylphenyl malonamide with [1,4,5]-oxa-diazepine dihydrobromide under the action of triethylamine to obtain 8-(2,6-diethyl-4-methyl benzene)tetrahydropyrazole [1,2d][1,4,5]-oxa-diazepine-7,9-dione, and finally reacting the 8-(2,6-diethyl-4-methyl benzene) tetrahydropyrazole[1,2d][1,4,5]-oxdiazepine-7,9-dione with pivalyl chloride to obtain the pinoxaden. According to the preparation method disclosed by the invention, by adopting a catalyst with low price, the production cost is reduced; besides, hydrogen peroxide-alkali is adopted in a preparation process to serve as a hydrolyzed system, so that environmental pollution is greatly reduced.
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- Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden
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Derivatives of the new class of 3-hydroxy-4-phenyl-5-oxo-pyrazolines were optimized towards both herbicidal activity on key annual grass weed species and selectivity in small grain cereal crops. The generic structure can be separated into three parts for the analysis of the structure-activity relationships, namely the aryl, the dione with its prodrug forms and the hydrazine moiety. Each area appears to play distinct and different roles in overall expression of biological performance which is further beneficially influenced by adjuvant response and safener action. Pinoxaden 6, a novel graminicide for use in wheat and barley incorporating a [1,4,5]oxadiazepane ring, eventually emerged as a development candidate from the discovery and optimization process.
- Muehlebach, Michel,Boeger, Manfred,Cederbaum, Fredrik,Cornes, Derek,Friedmann, Adrian A.,Glock, Jutta,Niderman, Thierry,Stoller, Andre,Wagner, Trixie
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experimental part
p. 4241 - 4256
(2009/10/02)
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