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A kind of 1,5-diaryl-3-carboxylate pyrazole compound, preparation method and use

A technology of methyl pyrazoles and ester pyrazoles, applied in the field of pesticides, can solve the problem that pyrazole-3-formyl compounds are not widely used, and achieve broad-spectrum high-efficiency bactericidal activity, good control effect, high yield effect

Active Publication Date: 2017-11-24
INST OF PLANT PROTECTION HENAN ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, as synthetic fragments with excellent biological activity, pyrazole-3-carboxyl compounds have not been widely used in agriculture

Method used

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  • A kind of 1,5-diaryl-3-carboxylate pyrazole compound, preparation method and use
  • A kind of 1,5-diaryl-3-carboxylate pyrazole compound, preparation method and use
  • A kind of 1,5-diaryl-3-carboxylate pyrazole compound, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of compound (1)

[0047] (1) The synthetic process of compound 1a:

[0048]

[0049] Add metal sodium (0.46g, 0.02mol) in batches to a flask containing 100ml of anhydrous methanol, stir, and add diethyl oxalate (2.92g, 0.02mol) and 4'-fluorobenzene Ethanone (1.38 g, 0.01 mol) was mixed, and the mixture was stirred and reacted at room temperature for 2-3 hours. After the reaction was completed, it was acidified to neutral, and a large amount of solids precipitated out. The product 1a could be obtained after filtration and draining. It could be used in the next reaction to prepare compound (1) without further purification. The purity of the obtained compound 1a was 90%, and the yield was 90%. The detection results of compound 1a are as follows:

[0050] 1 HNMRδ:8.05(q,2H,J 1 =8.4Hz,J2 =5.2Hz, Ar-H); 7.19(t, 2H, J=

[0051] 8.4Hz, Ar-H); 7.04(s,1H,CH); 3.94(s,3H); ESI-MS: m / z 247.1[M+Na] + ,Such as figure 1 shown.

[0052] (2) The sy...

Embodiment 2

[0055] Embodiment 2: the synthesis of compound (2)

[0056] (1) Synthetic process of compound 2a

[0057]

[0058] The synthesis process of compound 2a is the same as that of compound 1a, except that the raw materials used are 100 ml of anhydrous methanol, 0.02 mol of sodium metal, 0.02 mol of diethyl oxalate, and 0.01 mol of p-methylacetophenone. The purity of the obtained compound 2a was 90%, and the yield was 95%. The detection results of compound 2a are as follows:

[0059] 1 HNMRδ: 7.91 (d, 2H, J = 8.4Hz, Ar-H); 7.31 (d, 2H, J = 8.4Hz, Ar-H); 7.06 (s, 1H, CH); 3.94 (s, 3H, - OCH3); 2.37(s,3H,-CH3); ESI-MS: m / z 243.1[M+Na] + .Such as image 3 shown.

[0060] (2) Synthetic process of compound (2)

[0061]

[0062] The synthetic process of compound (2) is the same as that of compound (1), except that the raw material reactants used are compound 2a and 4'-cyanophenylhydrazine, with a yield of 85% and a purity of 95%. . The detection results of compound (2) are ...

Embodiment 3

[0064] Embodiment 3: the synthesis of compound (3)

[0065] (1) Synthesis process of compound 3a

[0066]

[0067] The synthesis process of compound 3a is the same as that of compound 1a, except that the raw materials used are 100 ml of anhydrous methanol, 0.02 mol of sodium metal, 0.02 mol of diethyl oxalate, and 0.01 mol of 2-acetylphenanthrene. The purity of the obtained compound 3a was 90%, and the yield was 85%. The detection results of compound 3a are as follows: 1 HNMRδ: 9.3(s, 1H); 8.80(d, 1H, J=8.0Hz, Ar-H); 8.13-7.65(m, 7H, Ar-H); 7.30(s, 1H, pyrazole-H); 3.99 (s,3H,-OCH3); ESI-MS: m / z 329.1[M+Na] + .Such as Figure 5 shown.

[0068] (2) Synthetic process of compound (3)

[0069]

[0070] The synthetic process of compound (3) is the same as that of compound (1), except that the raw material reactants used are compound 3a and 4'-cyanophenylhydrazine, and the yield of compound (3) is 80%. , with a purity of 95%. The detection results of compound (3) are a...

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Abstract

The invention discloses 1,5-diaryl-3-formate pyrazole compounds, a preparation method and application. The 1,5-diaryl-3-formate pyrazole compounds have a structural general formula as shown in the specification. In the structural general formula, aryl Ar is selected from the group consisting of a 2-phenanthryl group, a 3-phenanthryl group or a substituted phenyl ring, wherein the substituted phenyl ring is a halogen substituted phenyl group or a methylphenyl group; and R1 is -O(Ra), wherein Ra is an alkyl group with 1 to 3 carbon atoms. The compounds prepared by using the method provided by the invention have the advantages of short synthetic route, high yield and simple process, can effectively prevent and treat agricultural fungal diseases, and show strong bactericidal effect on wheat take-all fungus.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and specifically relates to a 1,5-diaryl-3-carboxylate pyrazole compound, a preparation method and an application. technical background [0002] As a large agricultural country, pesticides are an indispensable tool for preventing and controlling agricultural diseases. During the use of traditional chemical pesticides, there are serious pesticide residues, endangering the health of humans and animals, and polluting the environment. As the resistance of harmful organisms gradually increases, the amount of pesticides increases, and the phenomenon of pesticide residues and environmental pollution becomes more and more serious. Therefore, the development of green pesticides with high efficiency, low toxicity and environmental friendliness has become an inevitable trend in the development of pesticides. [0003] Pyrazole derivatives are nitrogen-containing heterocyclic compounds with a wide range o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/14A01N43/56A01P3/00
CPCA01N43/56C07D231/14
Inventor 马毅辉霍好胜郭梅燕张永超高新菊王恒亮
Owner INST OF PLANT PROTECTION HENAN ACAD OF AGRI SCI
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