- Design, synthesis, insecticidal activities, and molecular docking of novel pyridylpyrazolo carboxylate derivatives
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Based on our previous work, using the strategies of “scaffold hopping” and “intermediate derivatization method” (IDM), a total of 44 novel pyridylpyrazolo carboxylate derivatives were designed and synthesized. The structures of these compounds were identified by 1H NMR and 13C NMR, and the insecticidal activities of the target compounds against Plutella xylostella and Spodoptera frugiperda were tested. Compound G35 showed the best insecticidal activities against P. xylostella (LC50?=?33.65 mg/L) and S. frugiperda (mortality rate?=?61.21% at 100 mg/L). Preliminary structure–activity relationship analysis showed that the introduction of amino group and acetamide on the benzene ring helped to improve the insecticidal activity of the scaffold. Molecular docking model between compounds G34 or G35 and Ryanodine receptors (RyRs) of P. xylostella showed that RyRs may be a potential target of this series compounds and explained the difference in insecticidal activities. These findings provided guidance for further optimization of the pyridylpyrazolo carboxylate scaffold as potential insecticide.
- Peng, Hongxiang,Xu, Hanhong,Yang, Shuai,Zhao, Chen,Zhu, Jinyi
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- Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities
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Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1-aminocyclopropane-1-carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study, 1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L?1 against M. separate and 61.992 mg·L?1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of 1–23 with the target protein, ryanodine receptors.
- Chen, Rui-Jia,Cheng, Jia-Gao,Dong, Le-Feng,Feng, Ting-Ting,Gu, Yu-Cheng,Li, Zhong,Shao, Xu-Sheng,Wang, Gang-Ao,Wang, Jun-Jie,Xu, Xiao-Yong,Xu, Zhi-Ping,Zhou, Cong
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- PROCESS FOR THE PREPARATION OF CARBOXYLIC ACID DERIVATIVES OF 3-BROMO-4,5-DIHYDRO-1H-PYRAZOLES
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Disclosed a method for preparing compound of Formula (I) and (II) wherein R1, R2, R3, X and n are as defined in the disclosure.
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Page/Page column 10-13
(2021/02/26)
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- PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE
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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.
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- Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
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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.
- 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
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p. 1429 - 1436
(2021/05/06)
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- Preparation method of key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid
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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.
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- Synthesis method of chlorantraniliprole intermediate
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The invention relates to the technical field of chemical synthesis, and particularly discloses a synthesis method of a chlorantraniliprole intermediate. The synthesis method comprises the following steps: under the condition of an organic solvent, taking a compound I and phosphorus oxybromide as raw materials, and carrying out bromination and oxidation one-step reaction to prepare a compound II. Under the condition of a specific solvent, the compound I and phosphorus oxybromide in a specific proportion are used as raw materials, the compound II is prepared through one-step reaction, the product with the purity larger than 98.5% can be obtained only through simple aftertreatment of the reaction product, the yield can reach 92% or above, the raw materials are few in variety, the production cost is low, the amount of three wastes generated in the reaction process is small, and the method is green and environment-friendly and suitable for large-scale industrial production.
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Paragraph 0038-0061
(2021/10/27)
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- Preparation method of chlorantraniliprole intermediate
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The invention relates to a preparation method of a chlorantraniliprole intermediate. According to the preparation method, a raw material A is oxidized into an intermediate B in the presence of an oxidizing agent and a catalyst. The method is relatively simple in process, low in cost, small in three-waste amount, clean in system, high in target product content and yield, stable in process and suitable for industrial production.
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Paragraph 0016; 0020-0035
(2021/12/07)
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- METHODS FOR THE PREPARATION OF ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE
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Described herein are novel methods of synthesizing Ethyl 3-bromo- l-(3-chloropyridin-2- yl)-lH-pyrazole-5-carboxylate.
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Paragraph 0080-0081
(2021/05/21)
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- METHODS FOR THE PREPARATION OF ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE
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Described herein are novel methods of synthesizing Ethyl 3-bromo-1-(3 -chloropyridin-2-yl)-1H-pyrazole-5-carboxylate.
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Paragraph 0080-0091
(2021/07/17)
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- Synthesis of novel N-pyridylpyrazole derivatives containing 1,2,4-oxadiazole moiety via 1,3-dipolar cycloaddition and their structures and biological activities
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A series of novel 1,2,4-oxadiazole-containing N-pyridylpyrazole derivatives 12a?h were efficiently synthesized with pivaldehyde, pyridylpyrazole carboxylic acid and arylamine as raw materials via 1,3-dipolar cycloaddition. Their structures were identified
- Zhang, Yan,Shang, Junfeng,Li, Huan,Liu, Hang,Song, Haibin,Wang, Baolei,Li, Zhengming
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p. 1276 - 1280
(2019/11/26)
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- Preparation method of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formate
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The invention relates to a preparation method of 1-(3-chloropyridine-2-yl)-3-bromine-1H-pyrazole-5-formate. The preparation method comprises the following steps: reacting 3-chloro-2-hydrazinopyridineas an initial raw material with dimethyl butynedioate or diethyl butynedioate under an alkaline condition to obtain 1-(3-chloropyridine-2-yl)-3- hydroxyl-1H-pyrazole-5-formate, and then reacting the 1-(3-chloropyridine-2-yl)-3-hydroxyl-1H-pyrazole-5-formate with phosphorus oxybromide to obtain 1-(3-chloropyridine-2- yl)-3-bromine-1H-pyrazole-5-formate. According to the preparation method, the reaction steps are shortened, the use of an oxidation reagent is avoided, the operation is simple, the cost is lower, less three wastes are generated, the content of a target product is high, and the preparation method is suitable for industrial production.
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Paragraph 0043-0044
(2020/09/16)
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- Design, synthesis and insecticidal-activity evaluation of N-pyridylpyrazolo-5-methyl amines and its derivatives
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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.
- Yang, Shuai,Xu, Kaijie,Lai, Qiuqin,Zhao, Chen,Xu, Hanhong
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p. 4304 - 4311
(2020/09/21)
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- Preparation method of trifluoromethyl tetralone compound
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The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a trifluoromethyl tetralone compound. The problem that a large number of widely applied antibiotics have resistance so that serious side effects and heavy economic pressure are caused on patients due to excessive and excessive use of antibiotics in the prior art is solved. The structuralgeneral formula of the compound is shown in the specification, wherein R1, R2, R3, R4, X and Y are defined in the claim 1, and R1, R2, R3 and R4 are the same or different. The compound provided by theinvention has significant bactericidal and bacteriostatic effects, is suitable for the fields of medicines and farm chemicals, solves the problems of excessive use and excessive use of antibiotics caused by resistance of a large amount of antibiotics in the prior art, and is worthy of further development.
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- Insecticide containing chlorantraniliprole (by machine translation)
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Of the insecticide, is prepared, by compounding chlorantraniliprole, methoxyfenozide and indoxacarb as an active ingredient, wherein the insecticide synergistic effect is remarkably: by mass ratio of chlorantraniliprole: methoxyfenozide=2:1:1; indoxacarb, and the cost is low. (by machine translation)
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- Synthesis and Insecticidal Evaluation of Novel N-pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4-Oxadiazole Moieties
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Two series of novel N-pyridylpyrazole derivatives containing diacylhydrazine/1,3,4-oxadiazole moieties were designed and synthesized based on the structure of chlorantraniliprole and characterized via 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. The preliminary bioassay indicated that some of the title compounds I and II exhibited larvicidal activities against Mythimna separata with 90–100% death rates at 500?mg/L. The further test showed that these compounds had weak insecticidal activity against Mythimna separata and Plutella xylostella at 200?mg/L and might be not suitable as insecticide lead compound for further optimization.
- Wang, Wei,Zheng, Xiao-Rui,Huang, Xiao-Ying,Mao, Ming-Zhen,Liu, Kang-Yun,Xue, Chao,Wang, Lie-Ping,Ning, Bin-Ke
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p. 1330 - 1336
(2019/01/30)
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- Preparation method of alkyl 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazolyl-5-formate
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The invention discloses a preparation method of alkyl 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazolyl-5-formate, and belongs to the technical field of chemical synthesis. The invention provides a novel method for preparing the alkyl 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazolyl-5-formate, which is simple to operate, low in cost, green and environment-friendly. The preparation method comprises the following steps of enabling a compound of a formula I to react with an oxidizing agent in a solvent, so that the alkyl 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazolyl-5-formate is obtained, wherein the oxidizing agent is ammonium ceric nitrate or a hydrogen peroxide adduct. According to the method provided by the invention, the ammonium ceric nitrate or the hydrogen peroxide adduct is used as the oxidizingagent; a reaction can be carried out in a milder condition; afterwards, through condition optimization of adding a water remover and controlling a reaction temperature, and the like, the yield of a product can reach 80% or above; the method provided by the invention is environment-friendly; raw materials are low-cost and easily obtained, and the realization of industrialized production is facilitated.
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Paragraph 0041-0073
(2019/02/25)
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- System suitable for pyrazoline photocatalytic oxidation (by machine translation)
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The invention discloses a system suitable for the catalytic oxidation of pyrazoline, which is composed of a photo-sensitive catalyst, an oxidizing agent and various organic acids. To the present invention, TiO is supported by silica gel. 2 Powd
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Paragraph 0028-0031; 0036-0039
(2019/07/29)
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- A kind of including sulphone (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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The invention provides o-formylamino benzamide derivatives containing sulfone(sulfur)imine and a preparation method and used thereof. The invention relates to bisamide derivatives containing pyrazole formamide, wherein the general chemical structural formula of the bisamide derivatives is shown as I. The invention discloses the general structural formula and synthesis methods of the compounds, used of the compounds serving as insecticides, bactericides, plant virus resisting agents and plant activators and processing processes for the compounds in the preparation of the insecticides, the bactericides, the plant virus resisting agents and the plant activators in a manner that the compounds are mixed with agriculturally-acceptable assistants or synergists. The invention further discloses uses of combination of the compounds with the commercial insecticides, bactericides, plant virus resisting agents and plant activators in the prevention and treatment of the diseases, insect pests and viral diseases in agriculture, forestry and horticulture and a preparation method thereof.
- -
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Paragraph 0081; 0082; 0083
(2017/12/01)
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- A cyano sulphone containing N - (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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The invention provides o-formylamino benzamide derivatives containing N-cyano sulfone(sulfur)imine, a preparation method thereof and uses thereof. The invention relates to bisamide derivatives containing pyrazolecarboxamide, and the general chemical formula of the derivatives is shown as the formula I. The invention discloses a general structural formula and synthesis methods of the compounds, uses of the compounds serving as insecticides, bactericides, plant virus resisting agents and plant activators, and processing processes for the compounds in the preparation of the insecticides, the bactericides, the plant virus resisting agents and the plant activators in a manner of being mixed with agriculturally-acceptable assistants or synergists. The invention further discloses uses of combination of the compounds with the commercial insecticides, bactericides, plant virus resisting agents and plant activators in the prevention and treatment of the diseases, insect pests and viral diseases in agriculture, forestry and horticulture and a preparation method thereof.
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- Preparation process of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid
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The invention relates to a preparation process of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid. The preparation process comprises five steps including synthesis of 3-chloro-2-hydrazinopyridine, synthesis of 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate, synthesis of 3-bromo-1-(3-chloropyridine-2-yl)-4,5-dihydro-1H-pyrazole-5-ethyl formate, synthesis of 3-bromo-1-(3-chloropyridine-2-yl)-1H-pyrazole-5-ethyl formate and synthesis of the 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid. The preparation process of the 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid has the advantages that a sodium ethoxide solution is directly adopted; compared with the utilization of ethanol and metal sodium, a reaction is accelerated so that the reaction time is shortened; meanwhile, bromine remained in the reaction is removed by sodium hydrogen sulfite, so that the purity of the product is greatly improved; in the whole process, reaction conditions are relative moderate, so that the preparation process is suitable for industrial production and the yield of the product is greatly improved.
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- Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
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A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1–14 were designed and synthesized. The structures of all the title compounds were confirmed by 1H-NMR, 13C-NMR, 31P-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20–80% larvicidal activity against Mythimna separata at 1000?mg/L.
- Wang, Wei,Wang, Lie-Ping,Ning, Bin-Ke,Mao, Ming-Zhen,Xue, Chao,Wang, Hai-Yang
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p. 1362 - 1367
(2016/09/28)
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- Synthesis, Crystal Structure, and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group
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In search of environmentally benign insecticides with high activity, low toxicity, and low residue, a series of novel anthranilic diamide containing propargyl ether were designed and synthesized. All compounds were characterized by1H NMR spectroscopy, high-resolution mass spectrometry, or elemental analysis. The single crystal structure of 18g was determined by X-ray diffraction. The insecticidal activities against Lepidoptera pests of the new compounds were evaluated. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration.
- Huang, Zhiqiang,Tong, Jun,Zhou, Sha,Xiong, Lixia,Wang, Hongxue,Zhao, Yu
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p. 1036 - 1045
(2016/07/28)
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- Anthranilamide arthropodicide treatment
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This invention pertains to methods for protecting a propagule or a plant grown therefrom from invertebrate pests comprising contacting the propagule or the locus of the propagule with a biologically effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention also relates to propagules treated with a compound of Formula I and compositions comprising a Formula I compound for coating propagules.
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- Method of controlling particular insect pests by applying anthranilamide compounds
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This invention pertains to a method for controlling lepidopteran, homopteran, hemipteran, thysanopteran and coleopteran insect pests comprising contacting the insects or their environment with an arthropodicidally effective amount of a compound of Formula I, its N-oxide or an agriculturally suitable salt thereof wherein A and B and R1 through R8 are as defined in the disclosure. This invention further relates to a benzoxazinone compound of Formula 10 wherein R4 through R8 are as defined in the disclosure, useful for preparation of a compound of Formula I.
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- Novel chlorantraniliprole derivatives as potential insecticides and probe to chlorantraniliprole binding site on ryanodine receptor
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The lepidopteran pests such as diamondback moth are the regularly harmful pests of crops in the world, which brings enormous losses in crop production. Chlorantraniliprole is an anthranilic diamide insecticide registered for the control of lepidopteran pests with high insecticidal activity, however with uncertain binding site action target of chlorantraniliprole on ryanodine receptor, a series of new chlorantraniliprole derivatives were synthesized and the insecticidal activities of these compounds against diamondback moth were evaluated with chlorantraniliprole and indoxacarb as control. All compounds except 8h, 8p and 8t exhibited varying degree of activities against diamondback moth. Especially, compounds 8c, 8i, 8k and 8l displayed good insecticidal activities against diamondback moth and the activities are even better than that of indoxacarb during 72 h period. The Ki values of all synthesized compounds were calculated through autodocking program respectively. The relationship between calculation value of molecular docking and results of insecticidal activities indicated that the proposed specific receptor, the membrane-spanning domain protein of diamondback moth ryanodine receptor in our study might have chlorantraniliprole binding sites.
- Luo, Min,Chen, Qichao,Wang, Jin,Hu, Changyan,Lu, Jing,Luo, Xiaomin,Sun, Dequn
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p. 1987 - 1992
(2014/04/17)
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- Novel anthranilic diamide insecticides: Design, synthesis, and insecticidal evaluation
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Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by coupling the active substructures of anthranilic diamides and sulfoxaflor. The structures of the synthesized compounds were confirmed by infrared spectroscopy, 1H and 13C NMR, and elemental analysis. Several unique structural characteristics were revealed via the crystal structure analysis of compound N-(2-(2-methyl-2-(methylthio)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 16e. Bioassay results indicated that most of the synthesized compounds showed superior insecticidal activities against Mythimna separata and Plutella xylostella when compared with the positive control cyantraniliprole. In particular, N-(2-(2-methyl-2-(N-cyanomethylsulfideimino)propylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 17e showed excellent insecticidal activity against Mythimna separata, with a mortality rate of 100% at a concentration of 1μgmL-1. These results indicated that sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine moieties, as important active substructures, could improve or maintain the activity of the anthranilic diamide and promote novel pesticide development.
- Hua, Xuewen,Mao, Wutao,Fan, Zhijin,Ji, Xiaotian,Li, Fengyun,Zong, Guangning,Song, Haibin,Li, Juanjuan,Zhou, Like,Zhou, Lifeng,Liang, Xiaowen,Wang, Genhao,Chen, Xiaoyan
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p. 1491 - 1503
(2014/12/11)
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- Synthesis, insecticidal activities, and SAR studies of novel pyridylpyrazole acid derivatives based on amide bridge modification of anthranilic diamide insecticides
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Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, 1H NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
- Wang, Bao-Lei,Zhu, Hong-Wei,Ma, Yi,Xiong, Li-Xia,Li, Yong-Qiang,Zhao, Yu,Zhang, Ji-Feng,Chen, You-Wei,Zhou, Sha,Li, Zheng-Ming
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p. 5483 - 5493
(2013/07/27)
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- Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether
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In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamides containing allyl ether were designed and synthesized. All the compounds were characterized by 1H NMR spectroscopy, HRMS or elemental analysis. The single crystal structure of 18e was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results showed that some compounds exhibited excellent insecticidal activities against Lepidoptera pests. Among this series compounds, 18l showed 100 % larvicidal activity against Mythimna separate Walker and Plutella xylostella Linnaeus at the test concentration.
- Zhao, Yu,Xiong, Li-Xia,Xu, Li-Ping,Wang, Hongxue,Xu, Han,Li, Hua-Bin,Tong, Jun,Li, Zheng-Ming
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p. 3071 - 3088
(2013/09/23)
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- Synthesis, structure and insecticidal activities of some novel amides containing N-pyridylpyrazole moeities
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In our search for environmentally benign insecticides with high activity, low toxicity and low residue, a novel series of amides containing N-pyridylpyrazole moieties were designed and synthesized. The structures of the title compounds were characterized and confirmed by 1H-NMR and elemental analysis. Furthermore, the structure of compound 7l was determined by single crystal X-ray diffraction. The preliminary bioassay tests showed that some of them exhibited good insecticidal activities against Mythimna separata Walker, Plutella xylostella (Linnaeus, 1758) and Laphygma exigua Huebner.
- Dong, Wei-Li,Xu, Jing-Ying,Xiong, Li-Xia,Li, Zheng-Ming
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p. 10414 - 10428
(2012/11/07)
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- Design, synthesis and biological activities of novel anthranilic diamide insecticide containing trifluoroethyl ether
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Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole.
- Zhao, Yu,Li, Yongqiang,Xiong, Lixia,Wang, Hongxue,Li, Zhengming
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p. 1748 - 1758
(2012/11/13)
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- Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea
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Two series of anthranilic diamides containing acylthiourea and acylurea linkers were designed and synthesized, with changed length and flexibility of the linkers to compare to known anthranilic diamide insecticides. In total, 26 novel compounds were synthesized, and all compounds were characterized by 1H nuclear magnetic resonance and high-resolution mass spectrometry. Their insecticidal activities against oriental armyworm (Mythimna separata), mosquito larvae (Culex pipiens pallens), and diamondback moth (Plutella xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a-13e, 14a-14e, and 15a-15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a-17k) exhibited 100% larvicidal activity at 200 mg/L. The whole-cell patch-clamp technique indicated that compound 13b and chlorantraniliprole exhibited similar effects on the voltage-gated calcium channel. The calcium-imaging technique was also applied to investigate the effects of compounds 13b and 15a on the intracellular calcium ion concentration ([Ca2+]i), which indicated that they released stored calcium ions from endoplasmic reticulum. Experimental results denoted that several new compounds are potential activators of the insect ryanodine receptor (RyR).
- Zhang, Ji-Feng,Xu, Jun-Ying,Wang, Bao-Lei,Li, Yu-Xin,Xiong, Li-Xia,Li, Yong-Qiang,Ma, Yi,Li, Zheng-Ming
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p. 7565 - 7572
(2012/10/18)
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- Synthesis of some new n-pyridylpyrazoles and determination of their fungicidal activity
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Two series of novel N-pyridylpyrazole derivatives were designed and synthesized, and their structures were characterized by IR, 1H NMR, 13C NMR, high-resolution mass spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The fungicidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent fungicidal activities, which were comparable to the commercial fungicides.
- Zhao, Yu,Wang, Gang,Dong, Weili,Shi, Yanxia,Li, Baoju,Wang, Suhua,Li, Zhengming
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experimental part
p. 16 - 30
(2010/10/03)
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- Preparation Method of Phenylcarboxamides
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A preparation method of phenylcarboxamides of formula (I), the reaction scheme of which is as follows: wherein the groups are defined in the description. In this method, 3-halo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid esters (V) as the raw materials are hydrolyzed to obtain carboxylic acids of formula (IV) under a basic condition, and carboxylic acids (IV) are simultaneously acyl halogenated and oxidated to get acyl halide of formula (III), and then without the presence of a acid binging agent, acyl chlorides (III) are reacted with substituted anilines (II) to get phenylcarboxamides of formula (I) in high yield.
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Page/Page column 7
(2010/12/29)
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- CONVERSION OF 2-PYRAZOLINES TO PYRAZOLES USING BROMINE
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This invention relates to a method for preparing a compound of Formula 1 wherein L, R1, R2 and X are as defined in the disclosure, comprising contacting a 2 pyrazoline of Formula 2 with bromine at a temperature of at least about 80°C. (Formula 1) (Formula 2). This invention also discloses preparation of a compound of Formula 3 wherein X, Z, R5, R6, R7, R8a, R8b and n are as defined in the disclosure, using a compound of Formula 1a wherein R10 is as defined in the disclosure, prepared by the aforesaid method for preparing a compound of Formula 1. (Formula 3) (Formula 4).
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Page/Page column 27-29
(2008/06/13)
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