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Phenyl pyrazole amide derivatives as well as preparation method and application thereof

A kind of technology of phenyl bipyrazole amide and carboxamide group, which is applied in the field of phenyl bipyrazole amide derivatives, and can solve the problems such as no disclosure

Active Publication Date: 2016-07-27
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the prior art, there is no disclosure of the compound shown in the above-mentioned general structural formula (I) and the general structural formula (II) or the report that the compound shown in the above-mentioned general structural formula (I) and the general structural formula (II) is used for agrochemical nematicides

Method used

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  • Phenyl pyrazole amide derivatives as well as preparation method and application thereof
  • Phenyl pyrazole amide derivatives as well as preparation method and application thereof
  • Phenyl pyrazole amide derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1: the preparation of intermediate (C-1)

[0084] Dry the reaction device, put 10 mmoles of 2-amino-1-propanol (B), 12 mmoles of triethylamine, and 100 ml of dichloromethane into a single-necked flask, and slowly drop 10 mmoles of 3-difluoromethane in an ice bath Dichloromethane solution of 1-(2,6-2 chloro-4-trifluoromethylphenyl)-1H-pyrazole-4-carbonyl chloride (A) in 30ml of dichloromethane, stirred at room temperature for 1 hour after dropping, and placed After 3 hours, separated by TLC (developing solvent: ethyl acetate), a white solid (C-1)3-(difluoromethyl)-N-(1-hydroxypropan-2-yl)-1-phenyl-1H-pyrazole was obtained -4-carboxamide.

[0085] The above (B) can also be replaced with 2-amino-1-propanol (L type), 2-amino-2-methyl-1-propanol, aminoethanol, etc. to obtain the corresponding intermediate (C-1).

Embodiment 2

[0086] Embodiment 2: the preparation of target compound (E-2)

[0087] Weigh 10 millimoles of the intermediate (C-1) prepared in Example 1 in a single-necked flask, use 20 ml of tetrahydrofuran as a solvent, and drop into 10 millimoles of 2-methyl-3-chloro-phenylisocyanate (D), Stir overnight at room temperature, concentrate, and separate by TLC (developing solvent is a mixture of V (ethyl acetate): V (petroleum ether) = 4:1) to obtain the target product (E-2), whose NMR data are as follows:

[0088] NMR 1 HNMR (600MHz, CDCl 3): δ8.04(s,1H),7.72(s,2H),7.51(t,J=54Hz,1H),7.19(d,J=7.9Hz,1H),7.10(t,J=8.1Hz, 1H),6.94(s,1H),6.82(s,1H),4.52-4.47(m,1H),4.38(dd,J=11.3,7.9Hz,1H),4.20(dd,J=11.6,3.4Hz ,1H),2.26(s,3H),1.31(d,J=6.5Hz,3H).

[0089] All compounds E-1 to E-107 can be synthesized by the same method.

[0090] 2. Preparation

Embodiment 3

[0091] Embodiment 3: Wettable powder formulation

[0092] 15% compound (E-a or E-b), 5% lignosulfonate (M q ), 1% lauryl polyoxyethylene ether (JFC), 35% diatomaceous earth and 44% light calcium carbonate are evenly mixed and pulverized to obtain a wettable powder.

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Abstract

The invention discloses a phenyl pyrazole amide compound shown in a structural general formula (E) and a preparation method thereof. Definition of each substituent is shown in the specification. The phenyl pyrazole amide compound is suitable for controlling nematodes.

Description

technical field [0001] The present invention relates to a class of phenylpyrazole amide derivatives. Background technique [0002] Patent documents WO2005028485, WO2007065661, WO2007000462, WO2008014905, WO2007003540, WO2006120219, WO2007031323, and US2009176844 report a class of compounds with high-efficiency fungicidal activity, which have the following general structural formula (I): [0003] [0004] Patent documents WO2007141009, WO2007144174, WO2007134799, WO2008151828, WO2008148570, WO2009024342, WO2009003672, WO2009 / 127726, WO2009 / 127722, WO2009 / 127718 have reported the following general structure of a class of similar bactericidal compounds [0005] [0006] In the above two types of structures, Q represents a substituted aryl group. [0007] In the prior art, there is no disclosure of the compound shown in the above-mentioned general structural formula (I) and the general structural formula (II) or the report that the compound shown in the above-mentioned ge...

Claims

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Application Information

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IPC IPC(8): C07D231/14A01N47/20A01P5/00
Inventor 彭伟立邢家华许天明陈杰孔小林董得臻朱冰春侯建宇黄红英姬文娟郑志文
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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