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A substituted pyrazolylpyrazolesulfonylurea compound or its salt acceptable as a pesticide, composition and use thereof

A technique for pyrazolylpyrazolesulfonylureas and compounds, which is applied in the fields of chemicals, applications, organic chemistry, etc. for biological control, and can solve the problems of undisclosed pyrazolesulfonylurea compounds and compounds with insufficient activity , to achieve the effect of good selectivity and safety, good activity and selectivity

Active Publication Date: 2022-02-18
HAILIR PESTICIDES & CHEM GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for important crops, these compounds may not be active enough or have selectivity issues
However, in the prior art, there is no specific disclosure of pyrazole sulfonylurea compounds in which substituents are combined on the pyrazole ring of the pyrazole ring.

Method used

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  • A substituted pyrazolylpyrazolesulfonylurea compound or its salt acceptable as a pesticide, composition and use thereof
  • A substituted pyrazolylpyrazolesulfonylurea compound or its salt acceptable as a pesticide, composition and use thereof
  • A substituted pyrazolylpyrazolesulfonylurea compound or its salt acceptable as a pesticide, composition and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] 2-(N-((1-(3-Cl-4,5,6,7-tetrahydropyrazolo[1,5A]pyridin-2-yl)4-cyano-1H-pyrazole-5- base) carbamoyl) sulfonamide) methyl benzoate (compound 1) synthesis:

[0098]

[0099] Add 5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridin-2yl)-1H-pyrazole-4-methanol to the reaction flask Nitrile 2.62g (10mmol), acetonitrile 30mL, 2-sulfonyl isocyanate methyl benzoate 2.4g (10mmol) was added under stirring, stirred at room temperature for 6h, TLC followed the reaction (ethyl acetate:petroleum ether=1:1, GF254 , UV color development), after the reaction was complete, spin out the solvent, and purify the compound by column chromatography to obtain 3.15 g of the target compound, a white solid powder, melting point: 110-112 ° C; 1 H-NMR (CDCl 3 -d 6 ,500MHz)δ:8.12-8.09(m,1H),7.79-7.76(s,1H),7.72-7.69(m,1H),7.48-7.54(m,2H),4.34-4.30(t,2H), 3.90-3.86 (s, 3H), 2.73-2.69 (t, 2H), 1.73-1.69 (m, 2H), 1.46-1.42 (m, 2H).

Embodiment 2

[0101] 2-(N-((1-(3-Cl-4,5,6,7-tetrahydropyrazolo[1,5A]pyridin-2-yl)4-cyano-1H-pyrazol-5yl ) carbamoyl) sulfonamide) benzoic acid synthesis (compound 2):

[0102]

[0103] Add 2-(N-((1-(3-Cl-4,5,6,7-tetrahydropyrazolo[1,5A]pyridin-2-yl)4-cyano-1H- Pyrazole-yl) carbamoyl) sulfonamide) methyl benzoate 5.03g (10mmol), methanol 30mL, add sodium hydroxide 0.41g (1.1mmol), water 1mL under stirring, stir at room temperature for 6h, follow the reaction by TLC (Ethyl acetate:petroleum ether=1:1, GF254, UV color development), after the reaction is complete, spin out the solvent, add 50mL dichloromethane, 10mL saturated saline, separate layers, and spin dry the solvent; column chromatography purifies the compound , to obtain 2.93g of the target compound, light yellow solid powder, melting point: 111-113°C; 1 H-NMR (CDCl 3 -d 6 ,500MHz)δ:8.18-8.14(d,1H),8.09-8.06(d,1H),7.91-7.88(s,1H),7.72-7.68(m,2H),4.25-4.23(t,2H), 2.82-2.78 (t, 2H), 2.11-2.07 (m, 2H), 1.97-1.92 (m, 2H).

Embodiment 3

[0105] Synthesis of compound 3:

[0106]

[0107] Add 5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-A]pyridin-2yl)-1H-pyrazole-4carbonitrile into the reaction flask 2.62g (10mmol), 30mL of acetonitrile, 2.6g (10mmol) of methyl 2-((isocyanatesulfonyl)methyl)benzoate was added under stirring, the reaction was stirred at room temperature for 6h, and the reaction was tracked by TLC (ethyl acetate:petroleum ether= 1:1, GF254, UV color development), after the reaction is complete, spin out the solvent, and purify the compound by column chromatography to obtain 3.04g of the target compound, a white solid powder, melting point: 115-117°C; 1 H-NMR (CDCl 3 -d 6 ,500MHz)δ:7.92-7.88(d,1H),7.78-7.76(s,1H),7.53-7.49(d,1H),7.48-7.43(m,1H),7.32-7.28(m,1H), 5.07-5.04(s,2H),4.05-4.03(t,2H),3.84-3.80(s,3H),2.72-2.68(t,2H),2.04-1.99(m,2H),1.87-1.84(m ,2H).

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Abstract

The present invention belongs to the field of pesticides, and specifically relates to a substituted pyrazolylpyrazolesulfonylurea compound or its acceptable salt, composition and use as a pesticide. The compound has the structure of formula (I): Group definitions are as indicated in the specification. The compound with the substituted pyrazolylpyrazole sulfonylurea structure of the present invention has higher herbicidal activity than known compounds, especially excellent herbicidal activity against common weeds in paddy fields.

Description

technical field [0001] The invention belongs to the technical field of pesticides, in particular to a substituted pyrazolylpyrazole sulfonylurea compound or its salts and compositions acceptable as pesticides, and to these compounds or their acceptable salts and compositions as pesticides Use as a herbicide. Background technique [0002] It is known that substituted pyrazole derivatives have herbicidal activity, and pyrazole sulfonylurea compounds and their herbicidal activity are described in the patent application number CN200580013624.6, and related pyrazolyl sulfonylurea compounds are also disclosed in CN94195190.1 middle. However, for important crops, these compounds may not be active enough or have selectivity issues. However, pyrazole sulfonylurea compounds in which substituents are bonded to the pyrazole ring of the pyrazole ring have not been specifically disclosed in the prior art. Contents of the invention [0003] In order to solve the above-mentioned proble...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N47/36A01P13/00
CPCC07D471/04A01N47/36C07D231/54C07D231/38
Inventor 杨春河李建国邢阳阳王旭刘明东葛家成
Owner HAILIR PESTICIDES & CHEM GRP