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Thiazolidinylpyridine amine compounds and their preparation methods and applications

A technology of thiazolidinyl pyridine amines and compounds, applied in the fields of botany equipment and methods, applications, organic chemistry, etc.

Active Publication Date: 2019-02-01
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many harmful germs, pests, and weed control agents on the market, due to the continuous expansion of the market and the resistance of foreign harmful germs, pests, weeds, the service life of drugs, the economics of drugs and other issues and people's expectations The increasing emphasis on the environment and beneficial organisms requires scientists to continue to study, and then develop new varieties of bactericidal, insecticidal, and herbicides that are efficient, safe, economical, environmentally compatible, and have different modes of action

Method used

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  • Thiazolidinylpyridine amine compounds and their preparation methods and applications
  • Thiazolidinylpyridine amine compounds and their preparation methods and applications
  • Thiazolidinylpyridine amine compounds and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1 This example illustrates the preparation method of compound 01 in Table 1

[0076]

[0077] 5-Chloromethylthiazole 5-hydroxymethylthiazole (0.15mol), thionyl chloride (0.25mol) and chloroform (150mL) were reacted under reflux conditions for 3 to 5 hours, and the solvent and excess dichloromethane were removed under reduced pressure. sulfoxide to obtain 16.6 g of the title compound.

[0078] N-(thiazol-5-ylmethyl)methanamine, at room temperature, slowly add a mixture of 5-chloromethylthiazole (7.5g) and chloroform (50mL) dropwise to 40% methylamine aqueous solution (150mL), and dropwise Afterwards, the stirring reaction was continued for 6-8 hrs, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed to obtain 4.5 g of the title compound.

[0079] 6-methoxy-N-((thiazol-5-yl)methyl)-N-methyl-3-nitropyridin-2-amine (compound 01 in Table 1) 2-chloro-6-methoxy -3-nitropyridine (0.05mol), N-(thiazol-5-ylmethyl)methanamine...

Embodiment 2

[0080] Example 2 This example illustrates the preparation method of compound 07 in Table 1

[0081]

[0082] N-(thiazol-5-ylmethyl)ethylamine at room temperature, slowly add a mixture of 5-chloromethylthiazole (7.5g) and chloroform (50mL) dropwise to 60% ethylamine aqueous solution (150mL), dropwise Afterwards, the stirring reaction was continued for 7-10 hrs, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed to obtain 4.2 g of the title compound.

[0083] 6-methoxy-N-((thiazol-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine (compound 07 in Table 1) 2-chloro-6-methoxy -3-nitropyridine (0.05mol), N-(thiazol-5-ylmethyl)ethylamine (0.05mol), potassium carbonate (0.05mol) and N,N-dimethylformamide (100mL), in React at room temperature for 16-20 hrs, extract with ethyl acetate, dry over anhydrous sodium sulfate, and remove the solvent. The resulting crude product is purified by column chromatography to obtain 5.2 g of the title product a...

Embodiment 3

[0084] Embodiment 3 This embodiment illustrates the preparation method of compound 25 in Table 1

[0085]

[0086] 6-methoxy-N-((4-trifluoromethylthiazol-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine (compound 25 in Table 1) with reference to the examples 1 or 2, using 4-trifluoromethyl-5-chloromethylthiazole instead of 5-chloromethylthiazole to synthesize 4.5 g of the title compound as a yellow viscous solid. 1 H NMRδ(CDCl 3 )(ppm)1.237(t,J=4.2Hz,3H,CH 3 ), 3.265 (q, J=7.2Hz, 2H, CH 2 ),3.841(s,3H,CH 3 ),5.112(s,2H,CH 2 ), 6.225(d, J=9Hz, 1H, Py H), 8.175(d, J=9Hz, 1H, Py H), 8.700(s, 1H, Thiazole H); GC-MS (EI, 70Ev) (m / z)362(M + ).

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Abstract

The present invention discloses a thiazole alkyl pyridylamine compound shown in formula (I) and a preparation method and application thereof, wherein R, R ', Z, R1 and R2 are as defined in the specification. The thiazole alkyl pyridylamine compound shown in formula (I) has bactericidal, acaricidal or herbicidal biologically activity, and has high activity on pathogenic bacteria such as sclerotinia sclerotiorum, botrytis cinerea pers, and the like.

Description

technical field [0001] The invention belongs to the field of bactericidal, insecticidal and herbicides, and in particular relates to thiazolidinylpyridinylamine compounds with bactericidal, insecticidal and herbicidal biological activities, a preparation method thereof, and a bactericidal, insecticidal and herbicidal composition containing the compounds , and use and method of controlling harmful germs, pests and weeds with these compounds. Background technique [0002] The control of harmful bacteria, pests, and weeds is very important in the process of achieving efficient agriculture. At the same time, the control of harmful germs, pests and weeds is also very important in forestry, animal husbandry, sideline, fishery and public health. Although there are many harmful germs, pests, and weed control agents on the market, due to the continuous expansion of the market and the resistance of foreign harmful germs, pests, weeds, the service life of drugs, the economics of drugs...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A01N43/78A01P3/00A01P7/02A01P7/04A01P13/00
Inventor 柳爱平王晓光欧晓明陈昊彬李建明刘民华何莲刘兴平任叶果孙炯
Owner HUNAN CHEM RES INST