Pyrazole methanol esters compounds, preparation method and application thereof

A technology of ester compounds and pyrazole carbinol, which is applied in the field of pesticides and can solve the problems that the application of pyrazole carbinol ester compounds has not been reported.

Inactive Publication Date: 2009-02-11
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] But, pyrazole carbinol ester compound and its applic

Method used

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  • Pyrazole methanol esters compounds, preparation method and application thereof
  • Pyrazole methanol esters compounds, preparation method and application thereof
  • Pyrazole methanol esters compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the preparation of (4-chloro-3-ethyl-1-methyl-5-pyrazolyl) methyl p-tert-butylbenzoate

[0055] A solution composed of p-tert-butylbenzoyl chloride (10.9g, 0.055mol) and toluene (30ml) was slowly added dropwise under stirring and cooling in an ice-water bath to 4-chloro-3-ethyl-1-methyl- In a mixture of 5-hydroxymethylpyrazole (8.7g, 0.05mol), triethylamine (6.0g, 0.06mol) and toluene (200ml). After the dropwise addition, the temperature of the reaction mixture was raised to about 30° C., and the stirring was continued at this temperature. It took about 4-5 hours to follow the chromatographic tracking until the reactant was basically converted completely. The resulting reaction mixture was poured into water (300ml). Let stand to layer. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and precipitated under reduced pressure. The residue was the title compound (Compound No.8 in Table 1), weighing 15 g, and was a li...

Embodiment 2

[0058]According to the method described in Example 1, Compound No.1 was prepared by reacting p-tert-butylbenzoyl chloride with 3-ethyl-1-methyl-5-hydroxymethylpyrazole, using benzoyl chloride and 3-ethyl Compound No.2 was prepared by reacting p-chlorobenzoyl chloride with 3-ethyl-1-methyl-5-hydroxymethylpyrazole to prepare compound No. 3. Compound No.4 was prepared by reacting o-methoxybenzoyl chloride with 3-ethyl-1-methyl-5-hydroxymethylpyrazole, using 2-chloro-5-nitro-benzoyl chloride and 3- Compound No.5 was prepared by the reaction of ethyl-1-methyl-5-hydroxymethylpyrazole, using Z-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)- 2,2-dimethylcyclopropanyl formyl chloride and 3-ethyl-1-methyl-5-hydroxymethylpyrazole react to prepare compound No.6, using 2,2-dimethyl-3-(2 , 2-dichlorovinyl) cyclopropanyl formyl chloride and 3-ethyl-1-methyl-5-hydroxymethylpyrazole reaction to prepare compound No.7, using p-chloromethylbenzene to chlorinated benzoyl chloride Compound No.9 was ...

preparation Embodiment 1

[0068] Formulation Example 1: wettable powder

[0069] 20 parts of the compound of the present invention, 10 parts of white carbon black, 55 parts of kaolin, 10 parts of sodium lauryl sulfate and 5 parts of calcium lignosulfonate were uniformly mixed together and jet milled to obtain a wettable powder with an active ingredient of 20%.

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Abstract

The invention discloses pyrazole methanol ester compounds shown as the General Formula (I): wherein, R<1> expresses C1-C5 alkyl, phenyl or substituted phenyl; R<2> expresses C1-C5 alkyl or C1-C5 alkyl halide; R<3> expresses C1-C5 alkyl, C1-C5 alkyl halide, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl or hetero aryl; X expresses hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, nitro, cyano, sulfur cyano, trifluoromethyl sulfonyl or trifluoromethyl sulfinyl. The invention also discloses a preparation method and applications of the compounds. The pyrazole methyl ester compounds has excellent control efficiency on harmful pathogenic bacteria, harmful insects and mites and can be used for preparing insecticides, acaricides or fungicides for the agriculture, horticulture and floriculture fields. The pyrazole methyl ester compounds also can be used for preparing control agents of harmful living beings in the fields of forestry, animal husbandry and public health, etc.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a novel pyrazole-methanol-containing ester compound, a preparation method of the compound and a pest control agent using the compound as an active ingredient. Background technique [0002] Since the 1990s, the development of pesticides has entered an era dominated by heterocyclic compounds. Among the published patent documents in recent years, about 90% are related to heterocyclic compounds, among which the research on pyrazole compounds is particularly active. Since the 1, 3, 4, and 5-four positions of the pyrazole ring can undergo group transformation, many substituted pyrazole compounds with biological activity have been found. Among them, not only fungicides, herbicides, but also highly effective insecticides and acaricides have been developed as pesticides and widely used in agriculture and horticulture. [0003] US 4950668 discloses that N-benzylpyrazole-5-amide deri...

Claims

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Application Information

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IPC IPC(8): C07D231/16A01N43/56A01P7/00A01P3/00
Inventor 郭丽琴马海军童益利马亚芳田辉凯曾霞刘丽刘婷李长乐徐尚成
Owner JIANGSU PESTICIDE RES INST
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