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Picolinafen derivative as well as preparation method and application thereof

A technology of flufenamid and its derivatives, which is applied in the field of flufenamid derivatives and its preparation, can solve the problems of no reports and achieve good herbicidal activity

Active Publication Date: 2021-12-28
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A kind of novel diflufenamide derivative (A) provided by the present invention, there is no report at present

Method used

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  • Picolinafen derivative as well as preparation method and application thereof
  • Picolinafen derivative as well as preparation method and application thereof
  • Picolinafen derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment one, the preparation of compound a

[0027] 1. Preparation of Intermediate 2

[0028]

[0029] 2-Chloro-6-trichloromethylpyridine (230.9 g, 1.0 mol) and 98% concentrated sulfuric acid (120 g, 1.2 mol) were successively added into a round bottom flask, and the reaction was stirred at 120° C. for 6 h. After the reaction, the temperature was lowered to 60°C, and 27% ammonia water (172.8ml, 1.2mol) was slowly added dropwise. After cooling to room temperature, suction filtration under reduced pressure gave 146.8 g of a white solid (Intermediate 2), with a yield of 93.5%.

[0030] 2. Preparation of Intermediate 4

[0031]

[0032] In a round-bottomed flask, 2-chloro-6-carboxypyridine (157.0 g, 1.0 mol), thionyl chloride (142.8 g, 1.2 mol), and 300 ml of toluene were sequentially added, and the mixture was refluxed for 5 h. After cooling down to room temperature, p-fluoroaniline (111.1 g, 1.0 mol) was added, and triethylamine (121.5 g, 1.2 mol) was added dr...

Embodiment 2

[0036] Embodiment two, the preparation of compound b

[0037] Except for using N-methyl-m-trifluoromethylaniline instead of m-trifluoromethylaniline, it was synthesized by the same method as that of compound a, and the total yield was 50.6%. The structural formula is as follows:

[0038]

[0039] ESI MS:390.2[M+H] +1 , 1 H-NMR (400MHz, DMSO) δ9.22(s, 1H), 8.02(d, 1H, J=7.5Hz), 7.88(d, 1H, J=7.5Hz), 7.69-7.51(m, 3H), 7.33 (m, 2H), 7.27 (s, 1H), 7.13 (m, 2H), 6.93 (m, 1H), 2.13 (s, 3H).

Embodiment 3

[0040] Embodiment three, the preparation of compound c

[0041] Except for using N-ethyl m-trifluoromethylaniline instead of m-trifluoromethylaniline, it was synthesized by the same method as that of compound a, and the total yield was 51.2%. The structural formula is as follows:

[0042]

[0043] ESI MS:404.6[M+H] +1 , 1 H-NMR (400MHz, DMSO) δ9.17(s, 1H), 8.11(d, 1H, J=7.5Hz), 7.93(d, 1H, J=7.5Hz), 7.62-7.43(m, 3H), 7.35 (m, 2H), 7.27 (s, 1H), 7.16 (m, 2H), 6.97 (m, 1H), 2.27 (m, 2H), 1.35 (m, 3H).

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Abstract

The invention belongs to the field of pesticide chemical industry, and relates to a picolinafen derivative as well as a preparation method and application thereof, the structural formula of the picolinafen derivative is shown in the specification, and the preparation method comprises the following steps: (1) preparing 2-chloro-6-carboxypyridine from 2-chloro-6-trichloromethylpyridine under the action of concentrated sulfuric acid; (2) preparing 2-chloro-6-acyl chloride pyridine from the 2-chloro-6-carboxypyridine under the action of phosphorus trichloride, phosphorus pentachloride or thionyl chloride; and (3) carrying out amidation reaction on the 2-chloro-6-acyl chloride pyridine and p-fluoroaniline, and then substituting a chlorine substituent group in the 2-chloro-6-acyl chloride pyridine and the p-fluoroaniline with N-substituted m-trifluoromethylaniline to obtain the picolinafen derivative. The picolinafen derivative disclosed by the invention has better herbicidal activity and can be used for preparing herbicides.

Description

technical field [0001] The invention belongs to the field of pesticide chemical industry, and relates to a diflufenamide derivative and a preparation method and application thereof. Background technique [0002] Picolinafen, a pyridine amide structure compound, is the earliest herbicide developed by BASFSE (BASF Corporation). It was launched in the market in 2002 and is mainly used for the control of various Annual grasses and some broadleaf weeds. This variety is a selective contact and residual herbicide, and its mode of action is to hinder the biosynthesis of carotenoids through the inhibition of phytoene dehydrogenase. Compared with other pyridinamide herbicides, flupifenamide has the characteristics of high herbicidal activity, long duration, not easy to decompose, and safe to crops. In the 1990s, BASF and Bayer had many patent reports on related derivatives of this class of inhibitors, and the research and development of novel fenpyramid derivatives still has extensi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81A01N43/40A01P13/00
CPCC07D213/81A01N43/40Y02A50/30
Inventor 黄险峰王艺翰朱玉岚王子璇
Owner CHANGZHOU UNIV
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