4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine and application thereof

An alkyl and aryl technology, applied in the field of new compounds and their preparation, can solve the problems of no reports of insecticidal activity

Inactive Publication Date: 2011-05-25
HUNAN UNIV
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Problems solved by technology

[0003] The preparation of 4-alkyl-6-aryl-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine and its insecticidal activity have not been reported

Method used

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  • 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine and application thereof
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  • 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine and application thereof

Examples

Experimental program
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Effect test

Embodiment 14

[0040] Preparation of Example 14-tert-butyl-6-(4-methoxyphenyl)-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine

[0041] (1) Preparation of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone

[0042] Chloropinatone (0.05mol), 1,2,4-triazole (0.05mmol), potassium carbonate (0.10mol), catalytic amount PEG600, ethyl acetate (60mL) were stirred and refluxed, reacted for 5.0h, filtered, and Add 60% HNO dropwise to the filtrate 3 (0.05mol) into a salt, filtered, the filter cake was placed in ethyl acetate, ammonia water was added dropwise, the solid was dissolved, separated, dried, and the solvent was recovered by distillation to obtain 3,3-dimethyl-1-(1,2, 4-triazol-1-yl)-2-butanone; yield 85.6%, melting point 60-62°C.

[0043] (2) Preparation of 4,4-dimethyl-1-(4-methoxyphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one

[0044] 3,3-Dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone (0.011mol), piperidine (0.1mL), toluene (30mL), add dropwise 4- Methoxybenzaldehyde (0.010mol) toluene solution (20...

Embodiment 24

[0047] Example 24- Preparation of tert-butyl-6-(4-chlorophenyl)-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine hydrochloride

[0048] (1) Preparation of 4,4-dimethyl-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one

[0049] 3,3-Dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone (0.011mol), piperidine (0.1mL), toluene (30mL), add dropwise 4- Chlorobenzaldehyde (0.010mol) toluene solution (20mL), stirred and refluxed, reacted for 8h, the reaction solution was washed with 3 × 50mL water, separated and distilled to recover the solvent to obtain yellow viscous 4,4-dimethyl-1-( 4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one.

[0050] (2) 4-tert-butyl-6-(4-chlorophenyl)-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine hydrochloride to prepare

[0051] 4,4-Dimethyl-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one, thiourea (0.011mol) , ethanol (60ml), stirred and refluxed, and reacted for 6h. Cooled, precipitated solid, filtered and dried to obtain 4-tert-butyl-6-(4-chlor...

Embodiment 34

[0052] Example 34- Preparation of tert-butyl-6-(2-methoxyphenyl)-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine

[0053] (1) Preparation of 4,4-dimethyl-1-(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one

[0054] 3,3-Dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone (0.011mol), piperidine (0.1mL), toluene (30mL), add dropwise 4- Chlorobenzaldehyde (0.010mol) toluene solution (20mL), stirred and refluxed, reacted for 7h, the reaction solution was washed with 3×50mL water, separated, dried, and the solvent was recovered by distillation to obtain a yellow sticky substance 4,4-dimethyl-1 -(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one.

[0055] (2) Preparation of 4-tert-butyl-6-(2-methoxyphenyl)-5-(1,2,4-triazol-1-yl)-2-amino-1,3-thiazine

[0056] 4,4-Dimethyl-1-(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-one, thiourea (0.011 mol), ethanol (60ml), stirred and refluxed, reacted for 24h, added ammonia water for neutralization, vacuum distillation and column chroma...

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Abstract

The invention discloses 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine shown as a chemical structural formula I and salts thereof. A method for preparing the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine has the following steps: heating 1-aryl-2-(1, 2, 4-triazole-1-yl)-3-alkyl-1-propylene-3-ketone and thiourea in ethanol, stirring materials for reaction, using ammonia for neutralization, and preparing and obtaining the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine through reduced pressure distillation and column chromatography. The invention also discloses application of the 4-alkyl-6-aryl-5-(1, 2, 4-triazole-1-yl)-2-amino-1, 3-thiazine to the preparation of pesticide.

Description

technical field [0001] The present invention relates to a new class of compounds and their preparation methods and applications, specifically 4-alkyl-6-aryl-5-(1,2,4-triazol-1-yl)-2-amino-1, 3-thiazine and its preparation method and application. Background technique [0002] Azole heterocyclic derivatives have always been paid attention to by drug and pesticide workers because of their good biological activity, high drug efficacy, wide bactericidal spectrum, and good systemic property [Comperhensive Heterocylic Chemistry. Pergamon Oxford, 1983, 5: 733-735], and triazoles are one of the more influential ones. The bactericidal mechanism of triazole fungicides is to affect the formation of fungal cell walls by hindering the biosynthesis of fungal ergosterol, and have good control effects on most fungal diseases that endanger crop growth. Triazole fungicides also have certain plant growth regulating activity [Pesticides, 1994, 33 (4): 19-20; J Med Chem, 1996, 39 (12): 842-849]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A01P7/04
Inventor 胡艾希王健华叶姣石磊
Owner HUNAN UNIV
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