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3-halogen diarylaminopyrazole amides and their application in pesticides

A technology of diarylaminopyrazole amides and compounds, which is applied in the field of 3-halogen diarylaminopyrazole amides, can solve the problems such as low concentration effect decline, achieve good effect, huge economic value, and good control effect Effect

Active Publication Date: 2021-07-30
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent application CN201610019343.1 discloses a pyrazole carboxamide compound containing a diarylamine group. Sheath blight, wheat scab, corn small spot, potato infestation, tobacco anthracnose, powdery mildew, tomato gray mold, apple rot, grape black pox and rape sclerotinia have certain antibacterial effect, but pot activity experiments show that the effect of the drug is good at a certain concentration, and the effect drops sharply at low concentrations

Method used

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  • 3-halogen diarylaminopyrazole amides and their application in pesticides
  • 3-halogen diarylaminopyrazole amides and their application in pesticides
  • 3-halogen diarylaminopyrazole amides and their application in pesticides

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Experimental program
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Effect test

Embodiment 1

[0043] Preparation of compound 1

[0044] For the synthesis method of pyrazole carboxamide, please refer to the reference (Xiao-Xiao Zhang et al, synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modified scaffold as potent antifungal agents. Chinese Chemical Letters 28(2017) 1731–1736).

[0045] For the synthesis method of 3,5-dichloro-2-aminodiphenylamine, see reference (Xiao-Xiao Zhang et al, synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modified scaffold as potent antifungal agents. Chinese Chemical Letters 28(2017) 1731 –1736)

[0046] Put 20mmol of 3,5-dichloro-2-aminodiphenylamine in a three-necked flask, then add 25mL of anhydrous dichloromethane and 5mL of triethylamine, stir in an ice bath, and then add 20mmol of pyrazole carboxylic acid chloride Transfer to a constant pressure funnel and slowly add it dropwise to a three-necked flask. After 30 minutes, the temperature was naturally raised to room...

Embodiment 2

[0050] The preparation method of compound 2 is the same as that of compound 1.

[0051] 1 H NMR (400MHz, DMSO-d 6): δ10.13(s,1H),8.41(s,1H),7.45(dd,J=7.9,1.5Hz,1H),7.41(s,1H),7.37(d,J=8.4Hz,1H) ,7.43–7.30(m,1H),7.36(t,J=54.0Hz,1H),7.33(s,1H),7.24(td,J=7.6,1.4Hz,1H),6.77(dd,J=8.4 ,2.4Hz,1H),6.74(d,J=2.4Hz,1H),3.95(s,3H);ESI-HRMS:m / z[M+H] + 411.0593.

[0052]

Embodiment 3

[0054] The preparation method of compound 3 is the same as that of compound 1.

[0055] 1 H NMR (400MHz, DMSO-d 6 ): δ9.58(s,1H),8.39(s,1H),7.55(s,1H),7.55(dd,J=8.0,1.2Hz,1H),7.44(t,J=54.0Hz,1H) ,7.22(dd,J=8.0,1.6Hz,1H),7.25(dd,J=5.2,3.9Hz,1H),7.13(dd,J=8.0,1.3Hz,1H),7.08(td,J=7.8 ,1.4Hz,1H),6.95(dd,J=6.4,2.8Hz,1H),6.88(d,1H),3.95(s,3H);ESI-HRMS:m / z[M+H] + 395.0886.

[0056]

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Abstract

The invention relates to 3-halogen diarylaminopyrazole amide compounds and applications thereof, belonging to the technical field of pesticides. The structure of the compound is shown in the following formula (I): wherein, R 1 is fluorine, chlorine or bromine; R 2 , R 3 are respectively fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethoxy or hydrogen, and R 2 , R 3 Cannot be hydrogen at the same time. The pot plant activity experiment of the 3-halogen diarylaminopyrazole amide compound of the present invention shows that the effect is good at high drug concentration, and the control effect on fungi is still good at low concentration, and the control effect does not drop sharply. If it encounters rain or fog during the application process, it still has a good control effect and high economic value.

Description

technical field [0001] The invention relates to 3-halogen diarylaminopyrazole amide compounds and applications thereof, belonging to the technical field of pesticides. Background technique [0002] In recent years, the fungicide market has grown rapidly, with many varieties on the market, and several blockbuster products have emerged, such as BASF’s flufenapyramide, Syngenta’s benzovinfluconazole, and DuPont’s fluthiazolpyridone , Inatreq of Dow AgroSciences, etc. Among them, succinate dehydrogenase inhibitor (SDHI) fungicides are growing rapidly in their own system. Among the top 20 pesticides in terms of global sales, SDHI fungicides have the fastest growth. In 2015, the global sales of SDHI fungicides were US$1.576 billion, a year-on-year increase of 14.9%, and the compound annual growth rate from 2010 to 2015 was as high as 29.8%. [0003] Succinate dehydrogenase inhibitors are a class of fungicides that act on pathogenic bacteria succinate dehydrogenase to inhibit the...

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 侯太平张爱贵金洪陶科
Owner SICHUAN UNIV
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