314020-44-5Relevant articles and documents
Method for preparing pinoxaden intermediate through micro-channel
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Paragraph 0047; 0052; 0053; 0054; 0059-0060; 0061; 0066-0071, (2020/08/02)
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
Preparation method of pinoxaden
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, (2019/12/25)
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.
Method for synthesizing pinoxaden through 2,6-diethyl-4-methylphenyl malonate
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Paragraph 0035; 0037; 0039; 0041, (2019/10/15)
The invention relates to the field of organic synthesis, in particular to a method for synthesizing pinoxaden through 2,6-diethyl-4-methylphenyl malonate. The method comprises the following steps that1, the 2,6-diethyl-4-methylphenyl malonate reacts with hydrazine hydrate to form 4-(2,6-diethyl-4-methyl)-1,2,4,5-tetrahydropyrazole-3,5-diketone; 2, the 4-(2,6-diethyl-4-methyl)-1,2,4,5-tetrahydropyrazole-3,5-diketone is subjected to cyclization with diethylene glycol dimethanesulfonate or dibromo-diethylene glycol under the effect of triethylamine to generate 8-(2,6-diethyl-4-methylbenzene)-1,2,4,5-tetrahydropyrazole[1,2-d][1,4,5]oxo-dinitrogen-7,9-diketone; 3, the 8-(2,6-diethyl-4-methylbenzene)-1,2,4,5-tetrahydropyrazole[1,2-d][1,4,5]oxo-dinitrogen-7,9-diketone reacts with pivaloyl chloride under an alkaline condition to generate the pinoxaden. The method has the advantage that the use of expensive noble metal catalysts and hypertoxic cyaniding reagents is avoided, the adopted reagents are environmentally friendly, the cost is lowered, the process is simplified, the yield is high, the defects of the prior art are overcome, and the method is suitable for large-scale industrial production.
Phenyl pyrazoline compound with bioactivity and preparation method and application thereof
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Paragraph 0059; 0060; 0067, (2019/08/26)
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.
CHEMICAL PROCESS FOR THE SYNTHESIS OF HERBICIDAL PYRAZOLIDINEDIONE COMPOUNDS
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Page/Page column 18; 19, (2019/06/23)
The present invention relates to a novel process for the synthesis of herbicidal pyrazolidinedione compounds. In particular, a process for the preparation of a compound of formula (I), wherein R1, R2 and R3 are as defined herein. The present invention further relates to novel intermediate compounds utilized in said process, and methods for preparing said intermediate compounds.
Preparation method and intermediate of pinoxaden
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Paragraph 0044; 0045, (2018/07/30)
The invention provides a preparation method and an intermediate of pinoxaden. The preparation method includes: using 2-methylacrolein as a raw material; subjecting the raw material to cyclization andaromatization to obtain herbicide-pinoxaden. Compared with the prior art, the preparation method has the distinguishing features and the advantages that a completely different preparation strategy isadopted; a completely different nonaromatic compound is used as the raw material which is safe and easy to obtain; the preparation method is few in three wastes, low in cost and conducive to industrial production.
A zuozuo lin grass ester synthesis method (by machine translation)
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, (2018/12/14)
The invention discloses a method for synthesizing zuozuo lin grass ester, which belongs to the field of chemical industry. The specific process is as follows: the 2, 6 - diethyl - 4 - methylaniline by thermal decomposition is diazotized with sodium nitrite to generate 2, 6 - diethyl - 4 - methyl bromo; the malonic acid diethyl ester is added to the [1, 4, 5] - oxa diazepine b hydrobromide and alkali catalyst, synthesis of dihydro - 1 H - pyrazolo [1, 2 - d] [1, 4, 5] oxygen mixed two aza - 7, 9 (2 H, 8 H) - dione, it with 2, 6 - diethyl - 4 - methyl bromophenylacetic after coupling reaction to obtain the 8 - (2, 6 - diethyl - 4 - methyl phenyl) and four hydrogen pyrazole [1, 2 - d] [1, 4, 5] oxygen and nitrogen weed - 7, 9 (2 H, 8 H) - dione; will it with new pivaloyl chloride reaction zuozuo lin grass ester synthesis of the final product. This invention shortens the synthesis step, the operation is simple, and the cost is reduced, high economical efficiency and less pollution to the environment. (by machine translation)
Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden
Muehlebach, Michel,Boeger, Manfred,Cederbaum, Fredrik,Cornes, Derek,Friedmann, Adrian A.,Glock, Jutta,Niderman, Thierry,Stoller, Andre,Wagner, Trixie
experimental part, p. 4241 - 4256 (2009/10/02)
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.
