- A PROCESS FOR THE SYNTHESIS OF ANTHRANILIC ACID/AMIDE COMPOUNDS AND INTERMEDIATES THEREOF
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The present invention discloses a process for the synthesis of compound of formula (VII) or a salt thereof, wherein, R, R1, R2, R3, R4a and R4b are as defined in the detailed description. The process further comprises the synthesis of an anthranilic diamide compound of formula (I).
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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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- Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid
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The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention comprises the steps of mixing m-toluic acid and nitric acid, and carrying out nitration reaction to obtain 2-nitro-3-methyl benzoic acid, wherein the mass concentration of the nitric acid is 60-75%; mixing the 2-nitro-3-methyl benzoic acid, a hydrogenation reduction reaction solvent and a hydrogenation catalyst, and carrying out hydrogenation reduction reaction in a hydrogen atmosphere to obtain 2-amino-3-methyl benzoic acid; and mixing the 2-amino-3-methyl benzoic acid, a chlorination reagent, benzoyl peroxide and a chlorination reaction solvent, and carrying out a chlorination reaction to obtain the 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention has the advantages of cheap and easily available reaction raw materials, high product yield and high purity, and is easy for industrial production.
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- Method for preparing 2-amino-3-alkyl-5-chlorobenzoic acid
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The invention relates to a method for preparing a compound as shown in a formula (I). The method comprises the following steps of: performing chlorination reaction on a raw material as shown in a formula (II) to obtain the compound as shown in the formula
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Paragraph 0041-0177
(2021/07/14)
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- 2-amino-5-chloro-N,3-dimethylbenzamide preparation method
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The invention discloses a 2-amino-5-chloro-N,3-dimethylbenzamide preparation method, which comprises: carrying out a chlorination reaction a raw material represented by a formula I and a chlorinationreagent at the ortho-position and the para-position of amino to generate a compound represented by a formula II, carrying out a selective substitution reaction on the compound represented by the formula II and a cyano group mainly based on amino o-chlorine substitution under an alkaline catalysis condition by utilizing the thermodynamic stability difference between the o-chlorine and the p-chlorine of amino to generate a compound represented by a formula III, hydrolyzing the compound represented by the formula III into a compound represented by a formula IV, esterifying the compound represented by the formula IV to generate a compound represented by a formula V, and carrying out a reaction on the compound represented by the formula V and a monomethylamine methanol solution to generate 2-amino-5-chloro-N,3-dimethylbenzamide. According to the invention, the preparation method is high in yield, simple in reaction and small in toxic and side effects.
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Paragraph 0043; 0046; 0050; 0053; 0056; 0059
(2020/03/09)
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- Preparation method of 2-amino-5-chloro-N, 3-dimethylbenzamide
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The invention relates to a preparation method of 2-amino-5-chloro-N, 3-dimethylbenzamide. The preparation method comprises the following steps: taking 2-nitro-3-methylbenzoic acid as an initial raw material, and sequentially carrying out a reduction reaction, a chlorination reaction, an esterification reaction and an ammonolysis reaction, so as to obtain 2-amino-5-chloro-N, 3-dimethylbenzamide. The preparation method provided by the invention provides a new path for synthesis of 2-amino-5-chloro-N, 3-dimethylbenzamide, the yield of the whole path can reach 80% or above, the cost is significantly reduced, the reaction conditions of each step are mild, the number of three wastes is small, and the method is suitable for industrial production.
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- Method for preparing 2-amino-5-chloro-3-methylbenzoic acid
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A method for preparing 2-amino-5-chloro-3-methylbenzoic acid is disclosed. The method includes steps of: adding 2-amino-3-methylbenzoic acid (compound-I) into a reaction solvent, with the reaction concentration being 5-10 times (the ratio of the solvent v
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Paragraph 0009; 0011-0013
(2019/07/16)
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- Synthesis and Bioactivities Evaluation of Novel Anthranilic Diamides Containing N-(tert-Butyl)benzohydrazide Moiety as Potent Ryanodine Receptor Activator
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Anthranilic diamides have been proven to be a class of efficacious and safe insecticides targeting ryanodine receptors (RyRs) during the last decade. In order to develop innovative scaffolds with high insecticidal activity, two series of N-pyridylpyrazole
- Zhou, Yunyun,Wei, Wei,Zhu, Liangliang,Li, Yuxin
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p. 605 - 610
(2019/05/10)
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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; 0038; 0041; 0051; 0054; 0064
(2020/01/08)
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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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Paragraph 0051; 0052; 0053; 0054
(2017/05/19)
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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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- Synthesis method of 2-amino-5-chloro-N,3-dimethylbenzamide
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The invention discloses a synthesis method of 2-amino-5-chloro-N,3-dimethylbenzamide, belonging to the technical field of organic chemical synthesis. The method comprises the following steps: carrying out oxidation under the catalytic actions of N-hydroxyphthalimide and cobalt acetylacetonate to generate benzoic acid, carrying out substitution reaction with chlorine gas to generate 3,5-dichlorobenzoic acid, shielding off 5- chlorine by using a shielding reagent, carrying out methyl substitution on the 5- chlorine by using a Grignard reagent to generate 3-methyl-5-chlorobenzoic acid, carrying out nitro-substitution on the 3-methyl-5-chlorobenzoic acid and nitric acid under the catalytic action of concentrated sulfuric acid to generate 2-nitro-3-methyl-5-chlorobenzoic acid, carrying out catalytic hydrogenation to reduce the nitro group into amino group, carrying out reaction under the actions of N,N'-diisopropylcarbodiimide and 1-hydroxybenztriazole to obtain an intermediate, and carrying out reaction on the intermediate and methylamine to obtain the 2-amino-5-chloro-N,3-dimethylbenzamide. The method is simple to operate, and obviously enhances the synthesis yield to 92% or above.
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- Containing sulfide, N-cyano-sulfur (sulfone) imine structure substituted pyrazole carboxamides double-amide derivatives and process for their preparation and use
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The invention provides a double amide derivative containing a sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing pyrazolecarboxamide and a preparing method and purpose thereof, and relates to double amide derivatives containing the pyrazolecarboxamide. The double amide derivative containing the pyrazolecarboxamide has a chemical structure general formula as shown in the map I. The structure general formula and the synthetic method of the double amide derivative and the purpose for being used as insecticides, antiseptics, a plant virus resistance agent and a plant activator are disclosed. The double amide derivative containing the sulfur ether and N-sulfur cayano (sulphone) imine structure and replacing the pyrazolecarboxamide can be mixed with auxiliaries or synergists which are acceptable in agriculture to form a processing technology to be used for preparing the insecticides, the antiseptics, the plant virus resistance agent and the plant activator. The invention further discloses the purpose and preparing method of the double amide derivative containing the sulfur ether and N-sulfur cyano (sulphone) imine structure and replacing the pyrazolecarboxamide combining with commodity insecticides, commodity antiseptics, commodity plant virus resistance agents and commodity plant activators to be used for preventing and curing plant diseases, insect pests, virus diseases in agriculture, forestry and horticulture.
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Paragraph 0063-0065
(2016/10/09)
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- Design, Synthesis, and Biological Screening of Novel Anthranilic Diamides
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Three series of new anthranilic diamide derivatives containing sulfide, N-cyanomethylsulfilimine, and N-cyanomethylsulfoximine groups were designed and synthesized by combining the active substructures of anthranilic diamides and sulfoxaflor. The structures of all newly synthesized compounds were confirmed by IR and 1H/13C-NMR, and some of them were confirmed by elemental analysis or HRMS too. The synthesized compounds were screened for their insecticidal and fungicidal activities. Bioasssay results indicated that some of the synthesized compounds possessed certain degrees of insecticidal activity against Mythimna separata. However, some compounds exhibited good fungicidal activity against Sclerotinia sclerotiorum.
- Hua, Xuewen,Mao, Wutao,Fan, Zhijin,Ji, Xiaotian,Li, Fengyun,Zong, Guangning,Song, Haibin,Tatiana, Kalinina,Morzherin, Yury Yu.,Belskaya, Nataliya P.,Bakulev, Vasiliy A.
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p. 865 - 875
(2016/05/19)
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- O-carboxamido benzamide derivative based on ryanodine receptor, and preparation method and application thereof
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The invention provides a series of o-carboxamido benzamide derivatives, and preparation methods and applications thereof. The o-carboxamido benzamide derivatives have the chemical structure general formula represented as the formula I. The invention also discloses: the general formula and the synthetic method of the compounds and an application of the compounds in insecticides, acaricides and bactericides, and a process of preparing the acaricides and bactericides by mixing the compounds with agriculturally acceptable additives or synergists, and also discloses the combination of the compounds with commercial insecticides, acaricides, bactericides, anti-plant-viral agents and plant activators to prevent and treat diseases, pest damage, mite damage and viral diseases in the fields of agriculture, forestry and horticulture.
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Paragraph 0077; 0078; 0079; 0093; 0094
(2016/10/09)
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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 37
(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 36
(2015/11/27)
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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, 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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- Synthesis and bioactivity study of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives
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The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using 1H nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (EI-MS), and their biological activities at a concentration of 600 mg L -1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A. gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of -1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at R1 play crucial roles in the biological activities of the compounds.
- Ou, Junjun,Zhu, Xiaokun,Wang, Lei,Xu, Chuan,Liu, Feng,Ren, Long,Xu, Xibao,Wang, Yi,Rui, Changhui,Liu, Shangzhong
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p. 10942 - 10951
(2013/01/15)
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- PROCESS FOR MAKING 3-SUBSTITUTED 2-AMINO-5-HALOBENZAMIDES
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Disclosed is a method for preparing a compound of Formula 1 by contacting compound of Formula 2 with R1-NH2 in the presence of a carboxylic acid and a method for preparing a compound of Formula 2 by contacting a compound of Formula 4 with phosphorus tribromide. ( 1, 2, 4 ) wherein R1 is H, C1_C4 alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl; R2 is CH3 or C1; R3 is C1_C6alkyl or C3_ C6 alkenyl, each optionally substituted with up to 3 halogen and up to 1 phenyl; and X is C1 or Br. Also disclosed is a method for preparing a compound of Formula 5, wherein R4, R5, R6 and Z are as defined in the disclosure, using a compound of Formula 1 that is characterized by preparing the compound of Formula 1 by the method above.
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Page/Page column 16
(2008/06/13)
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- Design and synthesis of novel anthranilic diamides containing 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine
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A new kind of anthranilic diamides containing 5,7-dimethyl[1,2,4] triazolo[1,5-α]pyrimidine were designed and synthesised. Their structures were identified by means of elemental analysis, IR, 1H NMR and MS spectra. As the key intermediate, ethyl 5,7-dimethyl[1,2,4]triazolo[1,5-α] pyrimidine-2-carboxylate (7) was synthesised by applying microwave irradiation.
- Dong, Wei-Li,Liu, Xing-Hai,Xu, Jun-Ying,Li, Zheng-Ming
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scheme or table
p. 530 - 533
(2009/04/06)
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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 22
(2008/06/13)
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- Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators
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A novel class of anthranilic diamides has been discovered with exceptional insecticidal activity on a range of Lepidoptera. These compounds have been found to exhibit their action by release of intracellular Ca2+ stores mediated by the ryanodine receptor. The discovery, synthesis, structure-activity, and biological results are presented.
- Lahm, George P.,Selby, Thomas P.,Freudenberger, John H.,Stevenson, Thomas M.,Myers, Brian J.,Seburyamo, Gilles,Smith, Ben K.,Flexner, Lindsey,Clark, Christopher E.,Cordova, Daniel
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p. 4898 - 4906
(2007/10/03)
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- BENZOPYRAN COMPOUNDS USEFUL FOR TREATING INFLAMMATORY CONDITIONS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1). Wherein Z, X, R1, R2, R3, and R4 are as described in specification.
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- CHROMENE DERIVATIVES AS ANTI-INFLAMMATORY AGENTS
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The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (I). Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.
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- Quinazolinones and pyridinylpyrimidinones for controlling invertebrate pests
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This invention provides methods for controlling invertebrate pests comprising contacting the pests or their environment with an arthropodicidally effective amount of a compound of Formula (I), its N-oxides or agriculturally suitable salts wherein B, J, K, R3 and R4 and n are as defined in the disclosure.This invention also pertains to certain compounds of Formula (I) and compositions for controlling invertebrate pests comprising a biologically effective amount of a compound of Formula I and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
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- METHOD FOR PREPARING FUSED OXAZINONES
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A method for preparing a fused oxazinone is disclosed in which (1) a carboxylic acid is contacted with a sulfonyl chloride in the presence of an optionally substituted pyridine compound, the nominal mole ratio of sulfonyl chloride to carboxylic acid being from about 0.75 to 1.5; (2) the mixture prepared in (1) is contacted with an ortho-amino aromatic carboxylic acid in the presence of an optionally substituted pyridine compound, the nominal mole ratio of the ortho-amino aromatic carboxylic acid to carboxylic acid charged in (1) being from about 0.8 to 1.2; and (3) additional sulfonyl chloride is added to the mixture prepared in (2), the nominal mole ratio of additional sulfonyl chloride added in (3) to carboxylic acid charged in (1) being at least about 0.5. 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)2Cl as the sulfonyl chloride, a compound of Formula 2' as the carboxylic acid, and a compound of Formula 5' as the ortho-amino aromatic carboxylic acid (FORMULA 1a) (FORMULA III) (FORMULA 2') (FORMULA 5') wherein L, X, Y and R1 through R9 are as defined in the disclosure.
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