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Novel phenylamine compounds

A compound, selected technology, applied in the field of compounds, can solve problems that need to be improved, and achieve the effect of enhancing activity

Inactive Publication Date: 2020-01-10
PI IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the phenylamidine derivatives described in the previous literature have good effects, many situations still need to be improved

Method used

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Examples

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Effect test

preparation example Construction

[0197] Tank mix compositions are generally prepared by diluting one or more premix compositions containing different insecticides with any other adjuvants in a solvent such as water. Suitable carriers and adjuvants can be solid or liquid, substances commonly used in formulation technology, such as natural minerals or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers .

[0198] Generally, the content of ingredients required in tank mix preparations for foliar or soil application is 0.1-20%, especially 0.1-15%; the content of solid or liquid adjuvants (including solvents, such as water) is 99.9-80%, especially 99.9% to 85%. Wherein the adjuvant may be a surfactant based on the tank mix, with a content of 0-20%, especially 0.1-15%. Usually, the content of required ingredients in the premix preparation for foliar application is 0.1-99.9%, especially 1-95%, and the content of solid or liquid adjuvant (including solvent, su...

example 1

[0402] Example 1: Preparation of N-ethyl-N'-(4-(2-((3-fluorophenyl)thio)acetyl)-2,5-dimethylphenyl)-N-methylimine imine amide

[0403] The preparation of step A N-(2,5-dimethylphenyl) acetamide

[0404] To a stirred solution of 2,5-dimethylaniline (50 g, 413 mmol) in dichloromethane (500 ml) was added triethylamine (144 ml, 1031 mmol) and acetyl chloride (35.2 ml, 495 mmol) at 0°C. The reaction mixture was stirred at 0 °C for 2 hours. After the reaction was complete, the reaction mixture was poured into water. The aqueous layer was extracted with dichloromethane (3 x 1000 mL). The combined dichloromethane layers were separated and washed with water (2 x 500 mL) and brine solution (1 x 250 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under high vacuum to afford the desired N-(2,5-dimethylphenyl)acetamide (60 g, 368 mmol, 89% yield). LCMS (M+H): 165.50

[0405] Step B: Preparation of N-(4-(2-chloroacetyl)-2,5-dimethylph...

example 3

[0413] Example 3: N'-(4-(2-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)thio)acetyl)-2,5-dimethylphenyl)- Preparation of N-ethyl-N-methylformamidine

[0414] Perform steps A-D according to the procedure described in the general scheme.

[0415]To 1-(4-amino-2,5-dimethylphenyl)-2-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)thio)ethan-1-one ( To a stirred solution of 0.25 g, 0.667 mmol) in trimethyl orthoformate (10 mL), p-toluenesulfonic acid hydrate (6.34 mg, 0.033 mmol) was added, and the resulting mixture was stirred at 105° C. for 2 h. After complete conversion of the aniline derivative, the volatiles were evaporated to give the intermediate. This intermediate was dissolved in 1,4-dioxane (10ml), N-ethylmethylamine (0.394g, 6.67mmol) was added, and the mixture was stirred at 105°C for 2 hours. After completion of the reaction, the reaction mixture was evaporated to give the crude compound, which was purified by preparative HPLC to give the desired N'-(4-(2-((3-chloro-5-(tri...

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Abstract

The present invention relates to 4-substituted phenylamidine derivatives of the general formula (I), wherein R5-R6, ArA4, D, G, B, Q and an integer m have the meanings as defined in the description. The invention further relates to methods for their preparation and use of said compounds for controlling undesired phytopathogenic microorganisms, and agents for said purpose, comprising said phenylamine derivatives. This invention further relates to a method for controlling undesired phytopathogenic microorganisms by application of said 4-substituted phenylamidine derivatives of general formula (I) to such undesired microorganisms and / or to their habitat, according to the invention.

Description

technical field [0001] The present invention relates to compounds for the purpose of protecting crops by combating unwanted pathogenic microorganisms. More precisely, the subject of the present invention relates to novel aniline compounds for the purpose of protecting crops by combating undesired pathogenic microorganisms. Background technique [0002] Controlling the degree of damage of pathogenic microorganisms to crops is extremely important to achieve efficient cultivation. For example, the output of ornamental plants, vegetables, fields, grains and fruit trees will decrease significantly after being damaged by plant diseases and insect pests, and the prices will also rise. There are a variety of compounds on the market that can be used to control these hazards. Demand for new compounds that work better while being less expensive, less toxic, more environmentally friendly and / or have a different mechanism of action is increasing. It has been documented in the literatu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/12A01N37/52C07D231/12C07D235/04C07D249/08C07D471/04C07D207/333C07D209/04C07D209/12C07D277/74
CPCA01N37/52C07C257/12C07D231/12C07D235/04C07D249/08C07D471/04C07D207/333C07D209/04C07D209/12C07D277/74A01N39/00A01N43/36A01N43/38A01N43/40A01N43/50A01N43/52A01N43/56A01N43/653A01N43/78A01N43/84A01N43/90C07C323/45C07D207/36C07D213/81C07D231/44C07D231/56C07D239/26C07D277/68C07D295/16
Inventor 马鲁蒂·奈克维沙·A·马哈詹古拉布·E·瓦卢尼迪帕克·D·尼维东格苏卢尔·G·曼朱纳塔鲁芝·加尔嘉桑托什·什里达尔·奥特加尼婷·拉梅什·滕巴哈雷哈加拉瓦迪·M·文卡泰莎康斯坦婷·波斯沙尔尼亚历山大·G·M·克劳泽纳
Owner PI IND LTD
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