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Preparation method and application of pyrazole oxime compound containing 1-methyl-3-ethyl-4-chloro-5-formylpyrazole structure
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A formyl pyrazole, pyrazole oxime technology, applied in the field of pesticides, to achieve excellent control effect
Active Publication Date: 2020-03-31
浙江金果知识产权有限公司
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Problems solved by technology
However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice
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Embodiment 1
[0029]
[0030] 5 mmol of compound IIa was dissolved in 20 mL of dichloromethane, followed by the addition of 15 mmol of pyridine. Add 6mmol of intermediate III to it under ice-bath conditions, and after the addition is complete, continue to stir in ice-bath for 5 hours. The reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ia. 1 H NMR (400MHz, CDCl 3 ):δ8.18(s,1H,CH=N),7.29-7.35(m,1H,Ar-H),6.71-6.90(m,3H,Ar-H),4.11(s,3H,N-CH 3 ),3.63(s,3H,N-CH 3 ),2.65(q,J=7.6Hz,2H,CH 2 ),2.52(s,3H,CH 3 ), 1.23(t, J=7.6Hz, 3H, CH 3 ).
Embodiment 2
[0032]
[0033] 6 mmol of compound IIb was dissolved in 30 mL of tetrahydrofuran, followed by the addition of 24 mmol of triethylamine. 9mmol of Intermediate III was added thereto under ice-bath conditions, and after the addition was complete, stirring was continued for 9 hours in ice-bath. The reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ib. 1 H NMR (400MHz, CDCl 3 ):δ8.17(s,1H,CH=N),7.27-7.31(m,1H,Ar-H),7.14(d,J=8.0Hz,1H,Ar-H),6.83-6.99(m, 2H,Ar-H),4.11(s,3H,N-CH 3 ),3.63(s,3H,N-CH 3 ),2.65(q,J=7.6Hz,2H,CH 2 ),2.52(s,3H,CH 3 ), 1.23(t, J=7.6Hz, 3H, CH 3 ).
Embodiment 3
[0035]
[0036] 4 mmol of compound IIc was dissolved in 25 mL of chloroform, followed by the addition of 20 mmol of triethylamine. At room temperature, 5 mmol of intermediate III was added thereto, and after the addition was completed, the reaction was heated under reflux for 10 hours. The reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained residue was separated and purified by column chromatography to obtain the target compound Ic. 1 H NMR (400MHz, CDCl 3 ): δ8.15(s, 1H, CH=N), 7.65(d, J=9.2Hz, 2H, Ar-H), 6.74(d, J=8.8Hz, 2H, Ar-H), 4.11(s ,3H,N-CH 3 ),3.62(s,3H,N-CH 3 ),2.64(q,J=7.6Hz,2H,CH 2 ),2.51(s,3H,CH 3 ), 1.24(t, J=7.6Hz, 3H, CH 3 ).
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Abstract
The invention relates to a pyrazolyl oxime compound (I) containing a 1-methyl-3-ethyl-4-chloro-5-formacyl pyrazolyl structure, and a preparation method and application thereof. The pyrazolyl oxime compound (I) is prepared by condensing pyrazolyl oxime (II) and 1-methyl-3-ethyl-4-chloropyrazolyl-5-formacyl chloride (III). The pyrazolyl oxime compound (I) containing a 1-methyl-3-ethyl-4-chloro-5-formacyl pyrazolyl structure has the effect of preventing and controlling harmful insects. The compound can be used for preparing insecticide in the fields of agriculture, gardening and the like.
Description
technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a pyrazole oxime compound containing a 1-methyl-3-ethyl-4-chloro-5-formylpyrazole structure and a preparation method and application thereof. Background technique [0002] Pest control has always been the core field of pesticide scientific research, and the widespread use of insecticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice. [0003] Pyrazole oxime compounds are an important class of nitrogen-containing heterocyclic compounds, and their representative compounds, such as pyraflux, play an important role in killing insects in the field of pesticides. ...
Claims
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