Biphenyl compound and application thereof

A compound, biphenyl technology, applied in application, organic chemistry, animal repellent, etc., can solve problems such as unreported compounds

Active Publication Date: 2016-05-04
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there is no report of the compound shown in the general formula I of the present invention

Method used

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  • Biphenyl compound and application thereof
  • Biphenyl compound and application thereof
  • Biphenyl compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1: the preparation of compound 1

[0072]

[0073] 1.1, the preparation of intermediate IV-1

[0074] Weigh 3-(2,2,2-trifluoroethylthio)-4-methyl-6-fluoroaniline (intermediate III-1, which can be prepared by referring to methods reported in WO2010100189, US2012053052, JP2012519662, EP2403837 or CN102341376, etc. (obtained) 10.00 g (41.80 mmol) was placed in a 500 ml three-necked flask, 60 ml of concentrated hydrochloric acid was added, the temperature was lowered to 0-5° C., and the reaction was stirred for 30 minutes. A 100 ml aqueous solution of 3.46 g (50.15 mmol) of sodium nitrite was slowly added dropwise therein, and during this process, the reaction temperature was maintained not to exceed 0-5°C. After the dropwise addition was completed, the stirring reaction was continued for 1 hour.

[0075] A 100 ml aqueous solution of 13.88 g (83.61 mmol) of potassium iodide was slowly added dropwise to the diazonium salt solution, and during this process, th...

Embodiment 2

[0080] Embodiment 2: the preparation of compound 2 and 3

[0081]

[0082] 2.00 g (4.48 mmol) of compound 1 was dissolved in 20 ml of chloroform, and the temperature was lowered to 0-5°C. At this temperature, 0.98 g (4.68 mmol, 85% purity) of m-chloroperoxybenzoic acid was added in three portions. The reaction mixture was stirred at a temperature of 0-5°C for 2 hours. After the reaction was monitored by TLC, the reaction solution was washed successively with aqueous sodium thiosulfate and aqueous sodium bicarbonate and dried with anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure. The residue was column chromatographed (eluent was ethyl acetate and petroleum ether, the volume ratio is 1:6 to 1:3) to obtain 1.21 g of compound 2 (white solid) and 0.70 g of compound 3 (white solid) after purification. NMR and mass spectrometry data are as follows:

[0083] Compound 2: 1 HNMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):2.45(s,3H),2.54...

Embodiment 3

[0087] Embodiment 3: Determination of acaricidal activity

[0088] The compound of the present invention was used to test the activity of Tetranychus cinnabarinus. The method of determination is as follows:

[0089] After the compound to be tested prepared in the above synthesis example was dissolved in acetone, it was diluted to the required concentration with water containing 0.1% Tween 80, and the content of acetone in the total solution was not more than 10%.

[0090] Taking Tetranychus cinnabarinus Boisduval as the target, the Airbrush spray method was used to measure the activity, and the pressure of the Airbrush spray treatment was 0.7kg / cm 2 , the spray volume is 0.5ml, and placed in the standard observation room after treatment. After 72 hours, the number of surviving mites was investigated and the mortality rate was calculated.

[0091] The test results are as follows:

[0092] When the concentration of the drug solution was 100mg / L, the lethality of compounds 1, 2...

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Abstract

The invention belongs to the field of agricultural acaricides, and concretely relates to a biphenyl compound and an application thereof. The structure of the compound is represented by general formula I, and all substituent groups in the general formula I are defined in the description. The compound of the general formula I has excellent acaricidal activity, and can be used to prevent and control various mite damages.

Description

technical field [0001] The invention belongs to the field of agricultural acaricides, and in particular relates to a biphenyl compound and its application. Background technique [0002] Compounds with biphenyl structure have been extensively studied and applied in the field of medicine. Patent JP2009023910A discloses compounds of the following general formula, which are mainly used as acaricides and insecticides. [0003] [0004] There is no report on the compound represented by the general formula I of the present invention in the prior art. Contents of the invention [0005] The object of the present invention is to provide a kind of biphenyl compound that can control multiple harmful mites in a very small dose, which can be applied to prevent and control harmful mites in the fields of agriculture, forestry and sanitation. [0006] Technical scheme of the present invention is as follows: [0007] A biphenyl compound, as shown in general formula I: [0008] [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/09C07C317/14A01N31/16A01N41/10A01P7/02
CPCA01N31/16A01N41/10C07C317/14C07C323/09A01N31/08A01N25/02A01N25/30
Inventor 张立新张静班兰凤李鹏李轲轲徐靖博
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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