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500011-86-9Relevant articles and documents
Design, synthesis and insecticidal-activity evaluation of N-pyridylpyrazolo-5-methyl amines and its derivatives
Yang, Shuai,Xu, Kaijie,Lai, Qiuqin,Zhao, Chen,Xu, Hanhong
, p. 4304 - 4311 (2020)
In searching for novel insecticidal leads, a series of N-pyridylpyrazolo-5-methyl amines and their derivatives were designed and synthesized. Among the 22 target compounds obtained, bioassays indicated that some of the target compounds exhibited good insecticidal activities against Plutella xylostella (P. xylostella) and Spodoptera frugiperda (S. frugiperda). In particular, compound 9j revealed the best insecticidal activity against P. xylostella, with a LC50 value of 22.11 mg/L, and compound 9q had the best insecticidal activity against S. frugiperda which with 73.99% of mortality rate at 100 mg/L. Structure-activity relationship (SAR) analysis showed that 4-CF3 at the position of R1 linked with N-pyridylpyrazole via amide bond could enhance the insecticidal activity of the target compounds. This study provides valuable clues for the further design and optimization of N-pyridylpyrazole derivatives.
PROCESS FOR PREPARATION OF SUBSTITUTED PYRAZOLES
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Page/Page column 18-20, (2022/03/09)
: The present invention relates to the processes for the preparation of substituted pyrazole derivatives of formula (I), (II), (III), (IV), (IV-a) (V), (VII), which are useful as intermediates in anthranilamide insecticides production. In addition, the present invention is directed to a method for the preparation of anthranilamides of formula (VIII) using substituted pyrazole derivatives of formula (I), (III), (IV), (V), (VII). Furthermore, the present invention is directed to substituted halo-pyrazole compounds of formula (III), (IV) and (V), wherein X is halogen and R7 is hydrogen, C1-C4 alkyl.
Method for synthesizing chlorantraniliprole
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Paragraph 0024; 0029; 0032; 0037; 0040; 0045, (2021/10/11)
A solvent containing 2 - amino -3 - methylbenzoic acid is stirred, N - methyl -3 - methyl -2 - amino - benzamide is dissolved in alkali liquor in a stirring reaction process, and reacted with NCS to obtain N - methyl -3 - methyl -2 - amino -5 - chloro - benzamide. The reaction of the bromination reaction, the oxidation reaction and the condensation reaction is carried out by cooperation of a catalyst so as to obtain chlorantraniliprole. By optimizing the preparation steps of chlorantraniliprole, the whole process is relatively simple in process steps, the post-treatment is simple, intermediate products can be obtained directly after the single step is finished, high environmental control requirements are not needed in the whole synthesis step, and industrialization can be conveniently realized.
METHODS FOR THE PREPARATION OF 5-BROMO-2-(3-CHLORO-PYRIDIN-2-YL)-2H-PYRAZOLE-3-CARBOXYLIC ACID
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Paragraph 0190-0191, (2021/04/23)
Described herein are novel methods of synthesizing 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid from pyrazole or pyrazole derivatives. Also described herein are novel reaction intermediates.
Preparation method of key intermediate K acid of chlorantraniliprole
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Paragraph 0004; 0011, (2021/02/06)
The invention relates to a preparation method of a key intermediate K acid of chlorantraniliprole. The preparation method has the advantages of fewer reaction sites, less impurity generation and capability of realizing efficient, green and environment-friendly preparation of K acid. According to the method, ethyl acetoacrylate is used as a raw material and subjected to carbonyl protection, cyclization, deprotection, oxidation and bromination so as to finally prepare the K acid. The method has the advantages of high cyclization yield, good selectivity and high product purity.
PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE
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, (2021/02/26)
The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.
METHODS FOR THE PREPARATION OF 5-BROMO-2-(3-CHLORO-PYRIDIN-2-YL)-2H-PYRAZOLE-3-CARBOXYLIC ACID
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, (2021/04/23)
Described herein are novel methods of synthesizing 5-Bromo-2-(3-chloro-pyridin-2-yl)- 2H-pyrazole-3-carboxylic acid from pyrazole or pyrazole derivatives. Also described herein are novel reaction intermediates.
METHODS FOR THE PREPARATION OF 5-BROMO-2-(3-CHLORO-PYRIDIN-2-YL)-2H-PYRAZOLE-3-CARBOXYLIC ACID
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, (2021/04/23)
Described herein are novel methods of synthesizing 5-Bromo-2-(3-chloro-pyridin-2-yl)- 2H-pyrazole-3-carboxylic acid from pyrazole or pyrazole derivatives.
Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
Chen, Rui-Jia,Wang, Jun-Jie,Han, Li,Gu, Yu-Cheng,Xu, Zhi-Ping,Cheng, Jia-Gao,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
, p. 1429 - 1436 (2021/05/06)
A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.
Preparation method of key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid
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, (2021/06/26)
The invention discloses a preparation method of a key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method comprises the following steps: by taking 2,3-dichloropyridine as an initial raw material, carrying out a hydrazine hydrate reflux reaction, and then conducting cooling and centrifuging to obtain a 3-chloro-2-pyridyl wet product; then, enabling the 3-chloro-2-pyridyl wet product to react with diethyl maleate and sodium ethoxide to generate 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine; then carrying out bromination reaction on the 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine and phosphorus oxybromide to produce a 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product; putting the 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product into water, adding sodium persulfate, and carrying out a reaction so as to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid ethyl ester; and conducting hydrolysis in water to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method can greatly improve the production efficiency and reduce the production cost, and can be directly used for the next reaction without drying treatment.