cas 500011-91-6, 5-BROMO-2-(3-CHLORO-PYRIDIN-2-YL)-3,4-DIHYDRO-2H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER

Articles about 500011-91-6Total 37 be found

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Preparation method of bromopyrazole carboxylate compound
A preparation method for a bromopyrazole carboxylate compound. The chemical formula is as shows below, formula (I), formula (II), and the definition of each group in the formula is shown in the specification. A method for preparing a bromopyrazole carboxylate compound as a key intermediate in benzamide insecticides. The method is simple and easy to operate, safer, more reliable, and easier for industrial production.
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Paragraph 0026-0033

(2022/02/24)

Design, synthesis, insecticidal activities, and molecular docking of novel pyridylpyrazolo carboxylate derivatives
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
(2022/03/31)

Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities
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
(2022/02/03)

A PESTICIDALLY ACTIVE MIXTURE COMPRISING THIETANYLOXY COMPOUND, OXIDES OR SALTS THEREOF
The present invention relates to a pesticidal active mixture comprising thietanyloxy compound of formula (I), oxides or a salt thereof, Formula (I) wherein, R1, R2, R3, R4, R5 and R6, are as defined in the description, and at least one insecticidally active compound (II) or at least one fungicidally active compound (III).
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Page/Page column 79

(2022/02/06)

Preparation method of chlorantraniliprole
The invention relates to the field of insecticide synthesis, and discloses a preparation method of chlorantraniliprole. The preparation method comprises the following steps: synthesis of an intermediate I, synthesis of an intermediate II and synthesis of chlorantraniliprole. The method comprises the following steps: reacting 2, 3, 6-trichloropyridine serving as a raw material with hydrazine hydrate under the action of a catalyst A to obtain 3, 6-dichloro-2-hydrazinopyridine, carrying out hydrogenation reduction reaction under the action of a catalyst B to obtain an intermediate I, reacting theintermediate I with diethyl maleate, and preparing the 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate under the action of a catalyst C, and hydrolyzing after bromination to obtain an intermediate II, and preparing chlorantraniliprole from the intermediate II. According to the invention, 2, 3, 6-trichloropyridine is adopted to replace 2, 3-dichloropyridine as a raw material to preparethe intermediate I, so that the defects of difficulty in obtaining the 2, 3-dichloropyridine raw material, harsh synthesis conditions, low yield and the like are avoided, the total reaction yield ofthe intermediate I is improved, the intermediate II is prepared by a one-pot method, the post-treatment operation is reduced, and the synthesis cost of chlorantraniliprole is reduced.
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(2021/03/30)

PROCESS FOR THE PREPARATION OF CARBOXYLIC ACID DERIVATIVES OF 3-BROMO-4,5-DIHYDRO-1H-PYRAZOLES
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)

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE
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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Page/Page column 9; 13-15

(2021/02/26)

Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
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
p. 1429 - 1436
(2021/05/06)

Preparation method of key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid
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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(2021/06/26)

Preparation method and application of bromo pyrazole compound intermediate
The invention discloses a preparation method and application of a bromo pyrazole compound, namely 3-bromine-1-(3-chloro-5-R1-2-pyridyl)-4, 5-dihydro-1H-pyrazole-5-carboxylic ester. The preparation method comprises the following steps: step 1, enabling maleic acid diester and 3-chloro-5-R1-2-hydrazinopyridine to react in an alkaline solution to generate 3-hydroxy-1-(3-chloro-5-R1-2-pyridyl)-4, 5-dihydro-1H-pyrazol-5-carboxylate sodium salt; and step 2, enabling the sodium salt generated in the step 1 to react with phosphorus oxybromide to generate 3-bromine-1-(3-chloro-5-R1-2-pyridyl)-4, 5-dihydro-1H-pyrazole-5-carboxylic ester. According to the method, the bromo pyrazole compound is prepared through continuous reaction, raw materials such as acetic acid and sodium bicarbonate are omitted,generation of hydrolysis by-products of an intermediate is prevented, operation is simplified, the yield is increased and generation of waste water is reduced.
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Paragraph 0031-0032; 0034; 0035-0040

(2020/05/08)

Preparation method of trifluoromethyl tetralone compound
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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Paragraph 0036

(2020/07/12)

Design, synthesis and insecticidal-activity evaluation of N-pyridylpyrazolo-5-methyl amines and its derivatives
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
p. 4304 - 4311
(2020/09/21)

Insecticide containing chlorantraniliprole (by machine translation)
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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(2020/06/02)

Preparation method of chlorfenaphenamide intermediate and application thereof
The invention discloses a preparation method of a chlorfenaphenamide intermediate and an application thereof. The method comprises the following steps: step 1, at low temperature, dimethyl maleate reacts with hydrazine hydrate to generate methyl 3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate; step 2, methyl 3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate reacts with phosphorus oxybromide to generate methyl 3-bromine-4,5-dihydro-1H-pyrazole-5-carboxylate; step 3, in an alkaline solution, methyl 3-bromine-4,5-dihydro-1H-pyrazole-5-carboxylate reacts with 2,3-dichloropyridine to generate methyl3-bromine-1-(3-Chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylate as the key intermediate of chlorfenaphenamide. The preparation method has the advantages of simple operation steps, mild conditions and low production cost.
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Paragraph 0038; 0043-0044

(2019/11/13)

Synthesis and Insecticidal Evaluation of Novel N-pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4-Oxadiazole Moieties
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
p. 1330 - 1336
(2019/01/30)

Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives
To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.
Liu, Weijie,Li, Jiao,He, Kai,Huang, Fangfang,Ma, Yi,Li, Yuxin,Li, Qingshan,Xu, Fengbo
p. 417 - 420
(2018/05/24)

NOVEL ANTHRANILAMIDES, THEIR USE AS INSECTICIDE AND PROCESSES FOR PREPARING THE SAME.
The present invention relates to novel anthranilamides of Formula I, wherein, the definition of W1, W2, B1, B2, D, Z1, E, R1, R3, R4, m is as described in the description. The present invention also relates to the composition, combination, use and method of application of the anthranilamides of Formula I.
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Page/Page column 84

(2019/08/26)

Preparation technology of chlorantraniliprole impurity
The invention discloses a preparation technology of chlorantraniliprole impurity, and belongs to the technical field of organic synthesis. The technical problem to be solved by the invention is to provide a high-efficiency and low-cost technology for preparing a series of chlorantraniliprole impurity. The technology comprises the following steps: firstly using M1 as a raw material to prepare a compound M2, then carrying out oxidation and bromination with a one-pot method to prepare and obtain S1, then carrying out hydrolysis on S1 to prepare and obtain S2, and carrying out amidation on S2 to prepare S3. According to the method, separation and purification of an intermediate M2 are eliminated, the using amounts of a brominating agent and a solvent are reduced, the technological steps are shortened, the production cost is reduced, and dangerous chemical reagents such as bromine and hydrogen peroxide do not need to be used; according to the method, a series of chlorantraniliprole impuritycan be prepared, and effective guarantee is provided for production quality control for chlorantraniliprole.
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Paragraph 0141-0143; 0145-0146

(2018/05/30)

A kind of including sulphone (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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 0078; 0079; 0080

(2017/12/01)

A cyano sulphone containing N - (sulfur) imine O-formyl amino benzamide derivatives and its preparation and use
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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(2017/05/19)

Preparation process of 1-(3-chloropyridine-2-yl)-3-bromo-1H-pyrazole-5-formic acid
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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Paragraph 0009; 0012

(2017/02/17)

Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
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
p. 1362 - 1367
(2016/09/28)

Synthesis, Crystal Structure, and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group
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
p. 1036 - 1045
(2016/07/28)

Anthranilamide arthropodicide treatment
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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(2015/11/27)

Method of controlling particular insect pests by applying anthranilamide compounds
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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(2015/09/23)

Novel chlorantraniliprole derivatives as potential insecticides and probe to chlorantraniliprole binding site on ryanodine receptor
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
p. 1987 - 1992
(2014/04/17)

Novel anthranilic diamide insecticides: Design, synthesis, and insecticidal evaluation
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
p. 1491 - 1503
(2014/12/11)

Synthesis, insecticidal activities, and SAR studies of novel pyridylpyrazole acid derivatives based on amide bridge modification of anthranilic diamide insecticides
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
p. 5483 - 5493
(2013/07/27)

Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether
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
p. 3071 - 3088
(2013/09/23)

Synthesis, structure and insecticidal activities of some novel amides containing N-pyridylpyrazole moeities
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
p. 10414 - 10428
(2012/11/07)

Design, synthesis and biological activities of novel anthranilic diamide insecticide containing trifluoroethyl ether
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
p. 1748 - 1758
(2012/11/13)

Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea
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
scheme or table
p. 7565 - 7572
(2012/10/18)

Synthesis of some new n-pyridylpyrazoles and determination of their fungicidal activity
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
experimental part
p. 16 - 30
(2010/10/03)

Preparation Method of Phenylcarboxamides
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 3

(2010/12/29)

Rynaxypyr: A new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator
Rynaxypyr is a highly potent and selective activator of insect ryanodine receptors with exceptional activity on a broad range of Lepidoptera. A strong correlation between insecticidal activity and ryanodine receptor activation is observed along with selective activity against insect over mammalian receptors. The synthesis and biological results are presented.
Lahm, George P.,Stevenson, Thomas M.,Selby, Thomas P.,Freudenberger, John H.,Cordova, Daniel,Flexner, Lindsey,Bellin, Cheryl A.,Dubas, Christine M.,Smith, Ben K.,Hughes, Kenneth A.,Hollingshaus, J. Gary,Clark, Christopher E.,Benner, Eric A.
p. 6274 - 6279
(2008/03/14)

METHOD FOR PREPARING 3-HALO-4,5-DIHYDRO-1H-PYRAZOLES
This invention relates to a method for preparing 3-halo-4,5-dihydro-1H-pyrazole compound of Formula (I), comprising contacting with HX1 a different 4,5-dihydro-1H-pyrazole compound of Formula (II), wherein X1 is halogen
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Page 20

(2008/06/13)

ANTHRANILAMIDE INSECTICIDES
This invention provides compounds of Formula I, N-oxides and suitable salts thereof (INSERT FORMULA I HERE) wherein A is O or S(O)?m#191;J is a phenyl or heterocyclic ring as defined herein; andR1 through R12, n, m and r are as defined in the disclosure.Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I, an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I, an N-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.
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Page 18-19

(2010/02/06)