A kind of 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-carboxamide derivative and preparation method thereof
A technology of dichloroallyloxy and methylpyrazole, which is applied in the field of pesticides and achieves the effects of low production cost, high purity and easy operation
Inactive Publication Date: 2017-11-03
NANYANG NORMAL UNIV
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[0003] In recent years, there are more and more varieties of pesticides containing pyrazole heterocycles that have been commercialized or will be commercialized, especially the pyrazole amide fungicides that have developed rapidly in recent years. Bixafen, a pyrazole amide fungicide developed by Bayers, was discovered by Syngenta. And developed Isopyrazam, the compound fluxapyroxad announced by BASF and the fungicide Sedaxane (Zhang Yibin, World Pesticides, 2014,4(36):31-33.) that Syngenta is in the late stage of research and development. The common feature of these pesticide varieties is that they contain Amide compounds of pyrazole heterocycles have high fungicidal activity, but due to long-term use, plants gradually develop high drug resistance
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[0039] A 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-carboxamide derivative, the general chemical structure is as follows:
[0040]
[0041] Wherein, R is a methyl group.
[0042] The preparation method of above-mentioned 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-carboxamide derivatives comprises the following steps:
[0043] (1) Preparation of intermediate 3-hydroxyl-1-methylpyrazole-5-methyl carboxylate:
[0044] a. Add 100mmol methylhydrazine sulfate into a three-necked round-bottomed flask, dissolve it with 200mL methanol, then add 200mmol triethylamine to free it, and finally add 100mmol dimethyl butynoate, heat to 60°C, magnetically stir, and reflux 15h;
[0045] b. After the reaction is completed, stop heating, cool to 5°C, and stand for 2 days until white crystals precipitate, filter, wash with ethanol, and dry to obtain methyl 3-hydroxy-1-methylpyrazole-5-carboxylate. Yield is 60%, purity ≥ 95%, 1 H NMR (400MHz, DMSO-d6): δ=3.79(s, 3H), 3.88(s, 3H), 6.01(s, 1...
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Abstract
The invention belongs to the pesticide technical field, and particularly relates to 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-formamide derivatives and a preparation method thereof, and a pesticide composition containing the derivatives. The 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-formamide derivatives have high bacteriostatic activity, are suitable for prevention and control of plant diseases and virus diseases in the agriculture field, the forestry field and the gardening field, and effectively prevent and control crop diseases and pests.
Description
technical field [0001] The invention belongs to the technical field of pesticides, in particular to a 3-(3,3-dichloroallyloxy)-1-methylpyrazole-5-carboxamide derivative, a preparation method thereof, and a pesticide comprising the derivative combination. Background technique [0002] Nitrogen-containing heterocyclic compounds have high physiological and pharmacological activities and are of great value in the development of pesticides. Among them, pyrazole is a 1,2-diazole five-membered heterocyclic ring containing two nitrogen atoms. Compounds containing pyrazole rings have high biological activity. In 1946, Thmaposon reported for the first time that 2-pyrazol-5-one could inhibit biological growth and in 1949, American Rubber Company synthesized pyrazoles for foliar spraying. After the development of pesticides, pyrazole compounds have achieved rapid development in the field of pesticides. For example, Geigy.s.A. introduced the pyrazole ring into carbamate and organic phos...
Claims
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IPC IPC(8): C07D231/20C07D401/12C07D417/12A01N43/78A01N43/56A01N43/84A01P1/00A01P3/00
CPCA01N43/56A01N43/78A01N43/84C07D231/20C07D401/12C07D417/12
Inventor 毛武涛鲍克燕王志强李政道刘光印曹凤璞郭瑞婷
Owner NANYANG NORMAL UNIV