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1-(1,2,4-triazolyl)ketoxime ether-acylamide and application thereof

A kind of ketoxime ether amide, triazole-based technology, applied in the field of new compounds and their preparation, can solve the problems such as no reports on herbicidal and insecticidal activities, etc.

Inactive Publication Date: 2013-06-12
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No herbicidal and insecticidal activity reported for this type of compound

Method used

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  • 1-(1,2,4-triazolyl)ketoxime ether-acylamide and application thereof
  • 1-(1,2,4-triazolyl)ketoxime ether-acylamide and application thereof
  • 1-(1,2,4-triazolyl)ketoxime ether-acylamide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 N-benzyl-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-methyleneaminooxy]acetamide (4a ) preparation

[0034]

[0035] 2.16g (20.2mmol) benzylamine, 1.95g (14.1mmol) potassium carbonate, 1.73g (2.88mmol) PEG600, 20mL dichloromethane, N 2 For protection, 3.02 g (27.0 mmol) of chloroacetyl chloride was slowly added dropwise under ice bath conditions, and the dropwise addition was completed in 30 minutes, and the reaction was tracked by TLC for 6.9 hours. Rotary evaporation, washing with water, drying, and ethanol recrystallization gave 2.67 g of white solid 3a, yield 71.9%, m.p.88-90°C.

[0036] 0.92g (5.0mmol) compound 2, 0.86g (4.96mmol) N-benzyl-2-chloroacetamide, 0.15g (0.5mmol) tetrabutylammonium bromide (TBAB), 0.08g (0.05mmol) KI, 15 mL of toluene. 1.98g of 20% sodium hydroxide (9.9mmol) solution was slowly added dropwise, and the dropwise addition was completed within 10min, and the temperature was slowly raised to 60°C, and the reaction was comple...

Embodiment 2

[0037] Example 2 N-(3-methylphenyl)-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-methyleneamine oxide The preparation of base] acetamide (4b)

[0038]

[0039] Prepare 3b according to Example 1, react for 3.9h, and obtain 2.32g white solid after recrystallization from ethanol, yield 62.7%, m.p.86~87°C; prepare compound 4b according to Example 1, react for 2.8h, yield 24.2% , m.p.101-102°C. 1 H NMR (CDCl 3 , 400Hz) δ: 1.14(s, 9H, 3×CH 3 ), 2.37 (s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 4.73 (s, 2H, CH 2 ), 5.09 (s, 2H, NOCH 2 ), 6.97 (d, J=7.6Hz, 1H, C 6 h 4 4-H), 7.25(t, J=8.4Hz, 1H, C 6 h 4 5-H), 7.37(d, J=8.4Hz, 1H, C 6 h 4 6-H), 7.47(s, 1H, C 6 h 4 2-H), 7.94(s, 1H, C 2 h 2 N 3 3-H), 8.23(s, 1H, C 2 h 2 N 3 5-H), 9.19 (s, 1H, CONH).

Embodiment 3

[0040] Example 3 N-(3,4-dimethylphenyl)-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-ylidene Preparation of methylaminooxy]acetamide (4c)

[0041]

[0042] Prepare 3c according to Example 1, react for 1.5h, and obtain 2.75g off-white solid after ethanol recrystallization, yield 69.2%, m.p.94~96°C; prepare compound 4c according to Example 1, react for 1.4h, yield 49.5% , m.p.121-123°C. 1 H NMR (CDCl 3 , 400Hz) δ: 1.14(s, 9H, 3×CH 3 ), 2.24(s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 4.73 (s, 2H, CH 2 ), 5.09 (s, 2H, NOCH 2 ), 7.11 (d, J=7.6Hz, 1H, C 6 h 3 5-H), 7.30 (dd, J 1 =8.0Hz,J 2 = 2.4Hz, 1H, C 6 h 3 6-H), 7.40(s, 1H, C 6 h 3 2-H), 7.93(s, 1H, C 2 h 2 N 3 3-H), 8.20(s, 1H, C 2 h 2 N 3 5-H), 9.15 (s, 1H, CONH).

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Abstract

The invention discloses 1-(1,2,4-triazolyl)ketoxime ether-acylamide disclosed as a chemical structural formula I, wherein R is selected from hydrogen, C1-C2 alkyl group, and C3-C4 straight-chain or branched alkyl group; R1 is selected from hydrogen, C1-C2 alkyl group, and C3-C4 straight-chain or branched alkyl group; and Y is selected from aromatic group or benzyl group. The 1-(1,2,4-triazolyl)ketoxime ether-acylamide disclosed as the chemical structural formula I can be used for preparing bactericide or weedicide for killing Sclerotinia scleotiorum.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, specifically 1-(1,2,4-triazolyl)ketoxime ether amide, its preparation method and its application as a fungicide or herbicide. Background technique [0002] Wang Shengde et al. [Journal of Natural Sciences of Hunan Normal University, 2005, 28(1): 57-59] described a series of 4-chloroacetophenone oxime ether amide compounds, and determined the fungicidal, herbicidal and insecticidal properties of the new compounds. Activity, the compounds with better activity were screened out for general screening, the results of general screening are shown in Table 1. [0003] Table 1 Antibacterial, herbicidal and insecticidal activities of 4-chloroacetophenone oxime ether amides [0004] [0005] [Chemical Bulletin, 2006, 69 (8): 635-638], etc. [Chemical Bulletin, 2006, 69 (8): 635-638] described a series of oxime ether amide compounds in order to find new pesticid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08A01N43/653A01P1/00A01P3/00A01P13/00
Inventor 叶姣玄文静胡艾希刘臻彧
Owner HUNAN UNIV
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