110964-80-2Relevant academic research and scientific papers
A method for preparing nitroxalone herbicide
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Paragraph 0039-0042; 0049-0052; 0059-0062; 0069-0072, (2022/01/20)
The present invention belongs to the field of organic synthesis, specifically relates to a method for preparing nitrosulfonone herbicides. 4-Methylsulfonyl-2-nitrobenzoic acid as raw material by acyl chloride reaction, esterification reaction to obtain a
Preparation method of mesotrione
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Paragraph 0041; 0053-0059, (2021/08/11)
The invention provides a preparation method of mesotrione. The preparation method comprises: S1) carrying out a reaction on 2-nitro-4-methylsulfonylbenzoyl chloride and 1, 3-cyclohexanedione in the presence of an acid-binding agent to obtain an enol ester reaction liquid; and S2) adding a rearrangement agent as shown in a formula (I) into the enol ester reaction liquid, and performing a rearrangement reaction to obtain mesotrione. Compared with the prior art, the method has the advantages that the rearrangement agent containing unsaturated double bonds is adopted, under the synergistic effect of the double bonds, the rearrangement agent has better reactivity and reaction rate in the rearrangement reaction process, and the green and environment-friendly aftertreatment method is simple.
Synthesis, herbicidal activity, enzyme activity, and molecular docking of novel aniline thiourea
Li, Jia hui,Li, Ran hong,Wang, Yan,Li, Sui xin,Wu, Yun peng,Zhang, Jing,Zhu, Yong gang,Xie, Bei jie
, p. 664 - 671 (2021/03/31)
A series of new acyl thiourea derivatives containing aniline moiety were designed and synthesized. The preliminary herbicidal activity tests showed that some compounds had good herbicidal activity against Digitaria adscendens, Amaranthus retroflexus, especially for compound 4j (N-((4-chloro-3-(trifluoromethyl)phenyl)carbamothioyl)-4-(methylsulfonyl)-2-nitrobenzamide) and 4 l (N-((2-bromo-5-fluorophenyl)carbamothioyl)-4-(methylsulfonyl)-2-nitrobenzamide). The results showed that compound 4j and 4l had an inhibition rate of 98% and 96% on the root growth of Brassica napus L. at the concentration of 100 mg L?1. Compounds 4j and 4 l had higher comparative activity on Echinochloa crusgalli than the commercial herbicide bensulfuron-methyl. The preliminary structure–activity relationship (SAR) was also summarized. We also tested the in?vivo AHAS enzyme activity inhibition experiment of 17 compounds at 100 mg L?1, and the results showed that they all have inhibitory activity on the enzyme, with the highest inhibition rate reaching 43.66% (compound 4l). Based on the results of molecular docking to yeast acetohydroxyacid synthase (AHAS), the possible herbicidal activity mechanism of these compounds was evaluated.
7-, 8-, and 10-SUBSTITUTED AMINO TRIAZOLO QUINAZOLINE DERIVATIVES AS ADENOSINE RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITIONS AND THEIR USE
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Page/Page column 79; 106; 107, (2020/06/19)
In its many embodiments, the present invention provides certain 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives of Formula (I): or a pharmaceutically acceptable salt thereof, wherein ring A, R1, R2, and R4 are as defined herein, pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other therapeutic agents), and methods for their preparation and use, alone and in combination with other therapeutic agents, as antagonists of A2a and/or A2b receptors, and their use in the treatment of a variety of diseases, conditions, or disorders that are mediated, at least in part, by the adenosine A2a receptor and/or the adenosine A2b receptor.
Phenylpyrazolone compound or salt thereof, and preparation method and application thereof
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Paragraph 0046-0073, (2020/11/01)
The invention belongs to the field of pesticides, and particularly relates to a phenylpyrazolone compound or a salt thereof, and a preparation method and application thereof. The phenyl pyrazolone compound is shown as a general formula I which is describe
Synthesis process of mesotrione
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, (2019/10/04)
Belonging to the field of herbicide original drug preparation, the invention discloses a synthesis process of mesotrione. The process includes the steps of: (1) catalytic oxidation: taking 2-nitro-4-methylsulfonyl toluene as the raw material, and adopting oxygen as the oxidant to generate 2-nitro-4-methylsulphonylbenzoic acid under the catalysis of a manganese oxide octahedral molecular sieve loaded heteropolyacid-transition metal salt; (2) acyl chlorination: subjecting 2-nitro-4-methylsulphonylbenzoic acid to acyl chlorination to generate 2-nitro-4-methylsulfonylbenzoyl chloride; (3) condensation: carrying out condensation reaction on 2-nitro-4-methylsulfonylbenzoyl chloride and 1, 3-cyclohexanedione to obtain an enol ester intermediate reaction solution; (4) rearrangement: subjecting the enol ester intermediate to enol ester rearrangement under the catalysis of a rearrangement catalyst to obtain a crude product reaction solution; and (5) refining: refining the crude product reaction solution to obtain a mesotrione finished product. The process provided by the invention optimizes the reaction conditions, the conversion rate of each step is high, the yield and purity of the product are high, the whole production process does not involve hypertoxic materials, and the safety is high.
SYNTHESIS OF MESOTRIONE
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, (2018/10/25)
The present disclosure relates to a method for the synthesis of mesotrione. The method comprises reacting p-toluene sulfonyl chloride with alkali metal sulphite and alkali metal bicarbonate to obtain p-toluene alkali metal sulfinate. The p-toluene alkali metal sulfinate is reacted with alkali metal salt of monochloroacetic acid to obtain p- methylsulfonyl toluene. Further, p-methylsulfonyl toluene is nitrated to obtain 2-nitro-p- methylsulfonyl toluene. 2-nitro-p-methylsulfonyl toluene is oxidized and then halogenated to obtain 2-nitro-p-methylsulfonylbenzoyl halide. 2-nitro-p-methylsulfonylbenzoyl halide is reacted with alkali metal salt of 1,3-cyclohexanedione to obtain 3-(2-Nitro-p-methyl sulfonyl benzoyloxy) cyclohexane-l-one. 3-(2-Nitro-p-methyl sulfonyl benzoyloxy) cyclohexane-1- one is reacted with base, a third fluid medium and cyanide ion source to obtain an amorphous mesotrione. The present disclosure also discloses the steps of converting the amorphous mesotrione to crystalline mesotrione having purity greater than 99 %. The process of the present disclosure for preparing mesotrione is rapid, economic, and environment friendly.
Preparation method of mesotrione
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Paragraph 0017; 0044-0045; 0048-0049; 0052-0053; 0055-0056, (2018/09/13)
The invention provides a preparation method of mesotrione. The preparation method comprises the following steps: taking p-methylsulfonyl o-nitrobenzoic acid as a raw material; after carrying out acylchlorination, carrying out condensation reaction with 1,3-cyclohexanedione to obtain an intermediate 2-nitryl-4-methylsulfonylbenzoic acid-[3'-carbonyl-1'-cyclohexenol]-ester; then carrying out rearrangement of enol ester under a common catalysis effect of inorganic alkali and tertiary amine type organic alkali with relatively strong basicity, so as to obtain an acrylated cyclic 1,3-dicarbonyl compound mesotrione. According to the method provided by the invention, a virulent cyanide catalyst is not used, the reaction temperature is relatively low and the reaction time is short; a solvent can be cyclically used, the total mol yield of a prepared mesotrione product can reach 95 percent and the content is 98.5 percent; the technology is safe and environmentally friendly, has a small amount ofthree wastes and is suitable for industrial production.
Synthesis process of mesotrione
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, (2017/05/18)
The invention discloses a synthesis process of mesotrione. The synthesis process is high in yield and high in product purity and comprises the following steps: adding concentrated sulfuric acid, an oxidation water-containing mother solution and methyl p-tolyl sulfone into a nitration reaction kettle, evenly dropwise adding nitric acid in 2-3 hours to carry out nitratlon reaction, and keeping the temperature for 60-70 minutes after finishing dropwise adding nitric acid to obtain a nitrification solution; introducing the nitrification solution into an oxidation reaction kettle, then adding V2O5 as a catalyst, dropwise adding nitric acid and controlling the reaction temperature to be 142-146 DEG C; keeping the temperature for 1-2 hours after finishing dropwise adding nitric acid; reducing the temperature of a reaction solution to 100 DEG C, then adding water, and then reducing the temperature to 48-50 DEG C, then carrying out pressure filtration to obtain an oxidation product and the oxidation water-containing mother solution, circularly rinsing the oxidation product with water; refining the oxidation product and then drying the oxidation product at 55-70 DEG C to obtain 2-nitryl-4-methylsulfonylbenzoic acid; adding sulfoxide chloride into an acyl chlorination reaction kettle, then adding 2-nitryl-4-methylsulfonylbenzoic acid and DMF for increasing the temperature and carrying out reflux reaction, distilling after reacting for 11-12 hours for separating sulfoxide chloride out, and then carrying out esterification, condensation and rearrangement.
Synthetic process of mesotrione
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, (2017/05/18)
The invention relates to a synthetic process of mesotrione. The yield is high and the product purity is high. The synthetic process comprises the following steps: after adding concentrated sulfuric acid and methyl p-methylphenyl sulfone into a nitration reaction kettle, uniformly dropwise adding nitric acid within 4-5 hours for a nitration reaction, and after dropwise addition, preserving the temperature for 60-70 minutes to obtain a nitration liquid; leading the nitration liquid into an oxidation reaction kettle and then adding a catalyst V2O5 and water, then dropwise adding nitric acid and controlling the reaction temperature at 142-146 DEG C; after dropwise addition, preserving the temperature for 1-2 hours; cooling the reaction liquid to 100 DEG C, then adding water and cooling the reaction liquid to 48-50 DEG C, then performing filter pressing to obtain an oxidized product, and cyclically rinsing the oxidized product with water; drying the refined oxidized product to obtain 2-nitryl-4-methylsulfonyl benzoic acid; adding thionyl chloride into an acylating chlorination reaction kettle, then inputting 2-nitryl-4-methylsulfonyl benzoic acid and DMF to perform a temperature-raising reflux reaction, distilling thionyl chloride 11-12 hours after the reaction, then adding dichloromethane and 1,3-cyclohexanedione, and dropwise adding triethylamine for esterified condensation and rearrangement.
