- A PROCESS FOR THE SYNTHESIS OF ANTHRANILIC ACID/AMIDE COMPOUNDS AND INTERMEDIATES THEREOF
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The present invention disclosed a process for the synthesis of compound of formula (Z) or a salt thereof, wherein, R, R1, R2, R3 and R10 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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- Improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide
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The invention discloses an improved synthesis process of 2-amino-5-chloro-N, 3-dimethylbenzamide, which comprises the following steps: preparing an instrument and a reagent for synthesizing 2-amino-5-chloro-N, 3-dimethylbenzamide, synthesizing 12-amino-3-methylbenzoic acid in a three-neck flask, adding ferric trichloride hexahydrate and activated carbon, stirring, heating, reacting, cooling, filtering, adding 2328-methyl-2H-3, 1-benzoxazine-2, 4(1H)-dione (MAD, 3) into a three-necked flask, adding 2-amino-3-methylbenzoic acid (MAA), pyridine and nitrile, heating under stirring until the reaction is completed, adding the reaction solution obtained in the second step into the three-neck flask, heating under stirring, then dropwise adding a mixed solution of sulfonyl chloride and acetonitrile, carrying out heat preservation reaction, then cooling to room temperature, directly filtering the reaction solution, and distilling the filtered filtrate to obtain 3-dimethylbenzamide. According tothe method for preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the working procedure is simple and perfect in the process of preparing the 2-amino-5-chloro-N, 3-dimethylbenzamide, the preparation time can be well shortened, and the product quality is guaranteed.
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- AN EFFICIENT NEW PROCESS FOR SYNTHESIS OF 2-AMINO-5-CHLORO-N-,3-DIMETHYLBENZAMIDE
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Described herein are novel methods of synthesizing 2-amino-5-chloro-N,3- dimethylbenzamide. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.
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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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- Synthetic method of chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide
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The invention relates to a synthetic method of a chlorantraniliprole pesticide intermediate 2 - amino -5 - chlorine - N and 3 -dimethylbenzamide. Chloro, formylation gave 2 - amino -5 - chloro - N, 3 - dimethyl. The method has the advantages of simple reaction, low cost and high yield, and is a method suitable for industrial production.
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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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- 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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- A PROCESS FOR PREPARING ANTHRANILIC DIAMIDES AND INTERMEDIATES THEREOF
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The present invention relates a novel process for preparing a compound of Formula I, wherein, R1, R2, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description. The process comprises a novel and inventive step of converting a dione of Formula II into an isatoic anhydride of Formula V in a single step, wherein, R2 is F, Cl, Br or I; R1, R3a, R3b, R3c, R4, R5, R6, R7 and Z are as defined in the description.
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Page/Page column 14
(2020/09/08)
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- Synthesis and structure-insecticidal activity relationship of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety
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A series of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety, i.e., diamides 11, simple aryl-bearing amides 12 and acylthioureas 14 were successfully synthesized based on the key fluoro-containing phenylpyrazole acid intermediate. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and elemental analysis or HRMS. The bioassay results indicated that some of the compounds possessed excellent insecticidal activities towards oriental armyworm, diamondback moth and corn borer at low concentrations. For examples, compounds 11a, 11e?g and 14b exhibited remarkable larvicidal activities with LC50 values of 0.13 ? 0.39 mg/L and 0.0002 ? 0.0014 mg/L against oriental armyworm and diamondback moth, respectively, were comparable with those of the control chlorantraniliprole. Particularly, 11e were found superior to chlorantraniliprole in oriental armyworm tests (LC50: 0.23 mg/L vs. 0.26 mg/L); 11a, 11e, 11f and 14c in diamondback moth tests with LC50 values of 0.0002 mg/L, 0.0002 mg/L, 0.0008 mg/L and 0.0005 mg/L, respectively, were more effective than that of chlorantraniliprole. In addition, 12a also showed a promising insecticidal potential and development/optimization advantage. Compounds 11a, 11e–g, 12a, 14b and 14c could be considered as possible new leading structures for further study. The SAR investigation indicated that the compounds with fluorine motif (e.g., -F, -CF2H, -CF3) held apparently favorable insecticidal potentials, which provided useful guidance for further design/development of new phenylpyrazole-containing agrochemicals.
- Wang, Baolei,Wang, Hongxue,Liu, Hang,Xiong, Lixia,Yang, Na,Zhang, Yan,Li, Zhengming
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p. 739 - 745
(2019/08/20)
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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, insecticidal activities, and structure-activity relationship of phenylpyrazole derivatives containing a fluoro-substituted benzene moiety
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Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L-1, while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10-5 mg L-1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.
- Gao, Li,Li, Huangong,Li, Yuxin,Li, Zhengming,Ma, Yi,Meng, Fanfei,Sun, Binqiao,Sun, Pengwei,Xie, Yongtao,Xiong, Lixia,Yang, Na,Zhang, Yan,Zhao, Yangyang,Zhou, Sha
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p. 11282 - 11289
(2020/11/09)
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- 3 - Substituted -2 - amino -5 - halogenated benzamide preparation method
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The invention discloses a 3 - trifluoro methyl thiophenol and its derivatives of the preparation method, which belongs to the technical field of chemical synthesis. This invention is to solve the above problems of the prior art, provides a 3 - substituted - 2 - amino - 5 - halogenated benzamide of the preparation method, the method comprises the following steps: the compound of formula II, formula III compounds and organic solvent mixed, the response results in the type I of 3 - substituted - 2 - amino - 5 - halogenated benzamide. The invention through the reaction condition of a large number of optimization experiments, can be under mild conditions, in order to obtained in a high yield of high-purity 3 - substituted - 2 - amino - 5 - halogenated benzamide, after treatment is simple, is 3 - substituted - 2 - amino - 5 - halogenated benzamide for industrial production of the favorable conditions.
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Paragraph 0050; 0051; 0055-0057; 0061; 0062; 0069-0071
(2019/03/31)
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- Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives
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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
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supporting information
p. 417 - 420
(2018/05/24)
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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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- 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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- 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, 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 and insecticidal activities of 2,3-dihydroquinazolin-4(1H)-one derivatives targeting calcium channel
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A series of compounds containing dihydroquinazolinone moiety was designed and synthesized. Amine bridge part was changed in comparison with known anthranilic diamides insecticides. Their insecticidal activities against oriental armyworm (Mythimna separata) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compounds 5a and 5k showed 80% larvicidal activities against oriental armyworm at the concentration of 5 mg/L. The present study also explored the possible effects of target compounds on the high voltage-gated calcium channel and the calcium channels in the endoplasmic reticulum in the central neurons isolated from the third instar larvae of Spodoptera exigua using whole-cell patch clamp and calcium imaging technique. The results showed that compound 5a activated the high voltage-gated calcium channel in the central neurons of S. exigua weakly. The peak currents only increased by 6% of the initial value at the end of the 10-min recording after treated with 0.22 μM 5a, while chlorantraniliprole has an opposite effect. The effects of 5a on the intracellular calcium ion concentration ([Ca2+]i) in neurons were well investigated. The experimental results indicated that these novel compounds have different mechanism compared with chlorantraniliprole.
- Zhou, Yunyun,Feng, Qi,Di, Fengjuan,Liu, Qiaoxiao,Wang, Duoyi,Chen, Youwei,Xiong, Lixia,Song, Haibin,Li, Yuxin,Li, Zhengming
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p. 4968 - 4975
(2013/09/02)
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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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- 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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Page/Page column 29-30
(2012/08/08)
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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 and insecticidal activities of novel anthranilic diamides containing modified N-pyridylpyrazoles
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In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by 1H NMR, 13C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. 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, while compound 19 showed comparable higher activity at the concentration of 0.125 mg/L. The preliminary structure-activity relationship (SAR) was discussed.
- Feng, Qi,Liu, Zhi-Li,Xiong, Li-Xia,Wang, Ming-Zhong,Li, Yong-Qiang,Li, Zheng-Ming
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p. 12327 - 12336
(2011/09/14)
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- PROCESS FOR PREPARING 2-AMINO-5-CYANOBENZOIC ACID DERIVATIVES
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Disclosed is a method for preparing a compound of Formula 1 comprising (1) contacting a compound of Formula 2, with (2) at least one alkali metal cyanide and (3) at least one compound of Formula (4); wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; and X is Br, Cl or I. Also disclosed is a method for preparing a compound of Formula (4 )comprising contacting a mixture of (i) at least one compound of Formula (9 )and (ii) at least one metal reducing agent with (iii) dichlorobis(triphenylphosphine)nickel, and further disclosed is a method for removing nickel impurities from a mixture thereof with compounds of Formula (1 )comprising contacting the mixture with oxygen in the presence of an aqueous cyanide solution, and additionally disclosed is a method for preparing a compound of Formula (5); wherein R5, R6, R7 and Z are as defined in the disclosure, using a compound of Formula (1,) characterized by preparing the compound of Formula (1) by the method disclosed above.
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Page/Page column 28
(2009/03/07)
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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 15-16
(2008/06/13)
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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 24
(2008/06/13)
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