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Preparation method and application of 5-pyrazol amide compound having triazinone structure

A technology of pyrazole amide and compound is applied in the field of preparation of new compounds, which can solve the problem that insecticidal activity is not reported in literature and the like, and achieve the effect of good killing activity

Active Publication Date: 2018-06-12
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The insecticidal activity of 5-pyrazole amide compounds containing 4-amino3-methyl-6-phenyl-1,2,4-triazin-5-one structure has not been reported in the literature

Method used

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  • Preparation method and application of 5-pyrazol amide compound having triazinone structure
  • Preparation method and application of 5-pyrazol amide compound having triazinone structure
  • Preparation method and application of 5-pyrazol amide compound having triazinone structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 4-amino-3-alkyl-6-phenyl-1,2,4-triazin-5-(4H)-one (4.9mmol) to the reaction flask, 4-chloro-1-alkyl-3 -Alkyl-1H-pyrazole-5-carboxylic acid (4.9mmol) was dissolved in DMF, added Et 3 N (0.99g, 9.8mmol), then added EDCI (5.9mmol), HOBt (5.9mmol), reacted at 50°C for 8 hours, TLC detected that the reaction was complete. Post-treatment process: remove DMF under reduced pressure, add dichloromethane (50ml) to dilute, wash three times with water, wash once with brine, dry the dichloromethane layer with anhydrous sodium sulfate, remove dichloromethane under reduced pressure to obtain a crude product, and the crude product is chromatographed Column separation [V 石油醚 :V 乙酸乙酯 =6:1~4:1] 800mg of white crystals were obtained, m.p.92-95°C, yield 44%. 1 H NMR (400MHz, CDCl 3 )δ: 9.02(s, 1H, NH), 8.26(d, J=7.3Hz, 2H, C 6 h 5 ), 7.45-7.51 (m, 3H, C 6 h 5 ), 4.13 (s, 3H, NHCH 3 ), 2.70 (q, J=7.6Hz, 2H, CH 2 CH 3 , pyrazole), 2.64(s, 3H, CH 3 ), 1.28(t, J=7.6Hz, 3H, CH ...

Embodiment 2

[0034] Determination of insecticidal activity of 5-pyrazole amides containing triazinone structure.

[0035] Targets are armyworm, alfalfa aphid, cinnabar leafworm and rice planthopper.

[0036] Test medicament: embodiment 1 compound

[0037] Test concentration: The screening concentration is 500mg / L.

[0038] Test method: the compound of Example 1 was prepared into 5.0% EC preparation with emulsifier (Tween-80) and DMF, and diluted with distilled water to prepare a medicinal solution with the required concentration. The screening concentration is 500 mg / L, and the volume of drug treatment solution is 10 mL. With reference to the "National Southern Pesticide Creation Center Bioassay Standard Procedure", the insecticidal activity of the compound of Example 1 on armyworm (Mythima separata) was tested by the leaf dipping method.

[0039] Armyworm: soak an appropriate amount of cut corn leaf segments in the prepared medicinal solution, dry them naturally in the shade, put them ...

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Abstract

The invention provides 4-chloro-1-alkyl-3-alkyl-N-(3-alkyl-5-oxo-6-phenyl-1,2,4-triazine-4-(5H)-yl)-pyrazol-5-formamide shown as a formula (I), wherein R1 is H or straight-chain or branch-chain alkylcontaining 1 to 6 carbon atoms; R2 is H, halogen or straight-chain or branch-chain alkyl containing 1 to 6 carbon atoms; R3 is H or straight-chain or branch-chain alkyl containing 1 to 6 carbon atoms.The compound provided by the invention and a pharmaceutically-acceptable salt thereof have higher sterilizing activity under the test concentration, and can be taken as effective components of pesticides or pest compositions; a new option is provided for pesticides. The formula (I) is shown in the description.

Description

technical field [0001] The invention relates to a preparation method and application of a class of novel compounds, in particular to 5-pyrazole amide compounds containing a triazone structure and their application in the preparation of insecticides. Background technique [0002] N-Alkyl-pyrazole-5-carboxamides are compounds with insecticidal and acaricidal activities newly reported in the 1990s. They are highly regarded for their unique mechanism of action, safety and high efficiency, no cross-resistance and small dosage. focus on. Representative species such as tebufenpyrad and tofenpyrad. The action mechanism of tofenpyrad is similar to that of tebufenpyrad, and it has a broad insecticidal spectrum, and has contact killing effects on Phosphoptera, Hemiptera, Thrips and mites. [0003] [0004] Triazinone is an important structural fragment in pesticide molecules, and pymetrozine contains 4-amino 6-methyl-4,5-dihydro-1,2,4-triazin-3-one structure, which is used to cont...

Claims

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Application Information

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IPC IPC(8): C07D403/12A01N43/707A01P7/04A01P7/02
CPCA01N43/707C07D403/12
Inventor 李婉杨子辉武世杰
Owner HEBEI UNIVERSITY
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