- Method for synthesizing chlorantraniliprole
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The invention discloses a synthesis method of chlorantraniliprole, which comprises the following steps: dissolving phosgene in a solvent to form a material A, mixing 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid and 2-amino-5-chloro-3-methylbenzoic acid as raw materials in the presence of alkali and the solvent, and adding the material A to carry out a reaction to obtain 2-(3-Bromo-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazine-4-one (oxazinone, for short), and directly reacting the oxazinone with monomethylamine without purification to synthesize the chlorantraniliprole. The synthesis method has the advantages of cheap raw materials, high reaction activity, simple post-treatment process and no residue; the reaction synthesis conditions aremild, less three wastes are generated, special equipment is not needed, and industrial production is easy to realize.
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Paragraph 0023; 0026-0027
(2021/03/31)
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- PROCESS FOR PREPARATION OF ARTHROPODICIDAL ANTHRANILAMIDE COMPOUNDS
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The present invention provides a process for preparation of arthropodicidal anthranilamide compounds. The present invention further relates to one pot process for preparation of anthranilamide compounds.
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Page/Page column 21
(2021/08/20)
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- Preparation method of chlorantraniliprole
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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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- 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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Page/Page column 9; 11-12
(2021/02/26)
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- Method for synthesizing chlorantraniliprole
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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.
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- PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE
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The present disclosure relates to a process for the preparation of Chlorantraniliprole. The process of the present disclosure is carried out at an ambient temperature by using an inorganic base which can be readily separated from Chlorantraniliprole. The process is simple, efficient, environment friendly, and provides Chlorantraniliprole with high purity and high yield.
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Page/Page column 7-9
(2021/05/29)
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- PROCESS FOR PREPARATION OF ANTHRANILAMIDES
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The present invention provides a process for preparation and purification of anthranilamides.
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Page/Page column 34-35
(2020/07/15)
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- METHOD FOR PREPARING N-PHENYLPYRAZOLE-1-CARBOXAMIDES
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A method is disclosed for preparing compounds of Formula 1 by combining compounds of Formulae 2 and 3 and a sulfonyl chloride in a continuous process.
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Page/Page column 41-46
(2020/07/05)
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- Preparation method of chlorantraniliprole
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The invention relates to the technical field of synthesis processes of insecticides, and discloses a preparation method of chlorantraniliprole, which comprises the following steps: 1) adding 4-8 partsof maleic anhydride and 4-8 parts of methanol into a single-necked bottle, stirring the mixture, heating to 50 DEG C, and carrying out heat preservation reaction for 0.5-1.5 hours to obtain monomethyl maleate; and 2) cooling 80-120 parts of a hydrogen bromide-glacial acetic acid solution to 0 DEG C, then dropwise adding 3-5 parts of the monomethyl maleate, after addition is completed, carrying out heat preservation and stirring for 3-7 min, so that a large amount of a yellow viscous substance appears, and the monomethyl 3-bromomaleate can be prepared. The invention discloses a preparation method of chlorantraniliprole. The maleic anhydride, 2,3-dichloropyridine and 2-amino-3-methylbenzoic acid are adopted as starting materials to synthesize the target compound chlorantraniliprole througha convergent reaction. The structure is determined through HNMR, the route is mild in reaction condition, easy and convenient to operate and separate, raw materials are easy to obtain, special equipment is not needed, industrial production is easy to achieve, the action mechanism is novel and unique, and wide application and development prospects are achieved.
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Paragraph 0028; 0040; 0041; 0053; 0054; 0066
(2020/01/08)
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- Method for preparing benzamide compound by using pressure reducing method
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The invention relates to a method for preparing a benzamide compound represented by a general formula (I), wherein the reaction formula is defined in the specification, and each group in the formula is defined in the specification. According to the method, 3-bromo-1-(substituted pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (IV) is used as a raw material, and is simultaneously subjected to acyl chlorination and oxidation under a pressure reducing condition to prepare acyl chloride represented by a general formula (III), and the benzamide compound represented by the general formula (I) isprepared from the acyl chloride (III) and substituted aniline (II) in the absence of an acid-binding agent in a high yield manner.
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Paragraph 0038; 0040; 0042; 0055; 0056; 0057; 0058
(2019/08/01)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF ANTHRANILAMIDE DERIVATIVES
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The present invention relates to an improved process for the preparation of anthranilamide derivatives. More particularly, the present invention relates to an improved process for the preparation of Chlorantraniliprole-(Ia) and Cyantraniliprole-(Ib).
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- A synthesis method of chlorine insect benzamide (by machine translation)
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The present invention discloses one kind of chlorine insect benzamide synthesis method, relates to the field of organic synthesis. The invention two key intermediate 1 - (3 - chloro - 2 - pyridyl) - 3 - bromo - 1 H - 5 - pyrazole carboxylic acid with N - methyl - 3 - methyl - 2 - amino - 5 - chloro - benzamide synthesis method to re-design and improvement. Finally through the amidation reaction synthesize a final product chlorine insect benzamide. The synthesizing method of the invention for the intermediate 1 - (3 - chloro - 2 - pyridyl) - 3 - bromo - 1 H - 5 - pyrazole carboxylic acid synthesis provides a path; in the synthesis method steps of mild reaction conditions, and the steps can get better yield, overcomes the harsh reaction conditions in the prior art, the key steps to the problem of low yield, greatly reduces the production cost of the chlorine insect benzamide; in this synthetic method, the various steps in the few by-products, easy separation and purification, to further facilitate the industrial production. (by machine translation)
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- Intermediate 1 - (3 - chloro - 2 - pyridyl) - 3 - bromo - 1H - 5 - pyrazolyl formic acid
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Relating to the organic synthesis field, the invention in particular discloses a synthesis method for an intermediate 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazolecarboxylic acid. The synthesis method includes the steps of: taking 3-aminocrotononitrile as the raw material, mixing the raw material with hydrazine hydrate, carrying out cyclization reaction, bromination reaction, oxidation reaction and condensation reaction in order to obtain 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazolecarboxylic acid. The synthesis method provided by the invention provides a path for synthesis of the intermediate 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazolecarboxylic acid, the reaction conditions of each step are mild, good yield can be achieved, and the production cost is reduced.
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Paragraph 0048; 0049
(2017/08/25)
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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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- 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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Page/Page column 43
(2015/09/23)
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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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Page/Page column 42
(2015/11/27)
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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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- 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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- METHOD FOR PREPARING 2-AMINOBENZAMIDE DERIVATIVES
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A method for preparing a compound of Formula (1) comprising contacting a compound of Formulae (2) and (3) in the presence of a palladium source, a ligand, a base and carbon monoxide wherein R1, R2, X and R3 are as defined in the disclosure. A method for preparing a compound of Formula 5 wherein R1, R2, R3, R4, R5, R6 and Z are as defined in the disclosure, using a compound of Formula (1) characterized by preparing a compound of Formula (1) by the method disclosed above or using a compound of Formula (1) prepared by the method above.
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- COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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The present invention provides an arthropod pests control composition comprising, as active ingredients, 4-oxo-4-[(2-phenylethyl)amino]-butyric acid and a compound of formula (A); a method of controlling arthropod pests, which comprises applying effective amounts of 4-oxo-4-[(2-phenylethyl)amino]-butyric acid and a compound of formula (A) to a plant or growing site of plant; and so on.
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Page/Page column 6
(2011/06/19)
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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 4
(2010/12/29)
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- Rynaxypyr: A new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator
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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.
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p. 6274 - 6279
(2008/03/14)
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- METHOD FOR PREPARING N-PHENYLPYRAZOLE-1-CARBOXAMIDES
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A method is disclosed for preparing compounds of Formula (I) by combining compounds of Formulae (II and III) and a sulfonyl chloride. Also disclosed are compounds of Formula (III), which are useful as starting materials for this method.
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Page/Page column 28
(2008/06/13)
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- METHOD FOR PREPARING FUSED OXAZINONES
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A method for preparing a fused oxazinone is disclosed in which a carboxylic acid is contacted with a sulfonyl chloride and an isatoic anhydride in the presence of a tertiary amine, the nominal mole ratio of said sulfonyl chloride to said carboxylic acid being from about 1.0 to 1.5 and the nominal mole ratio of said isatoic anhydride to said carboxylic acid is from about 0.8 to 1.2. Also disclosed is a method for preparing a compound of Formula (III), using a compound of Formula (1a) that is characterized by preparing the fused oxazinone of Formula (1a) by the method above, using a compound of the formula LS(O)2CI as the sulfonyl chloride, a compound of Formula (2’) as the carboxylic acid, and a compound of Formula (5') as the isatoic anhydride wherein L, X, Y and R1 through R9 are as defined in the disclosure.
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