Preparation and application of pyrazole oxime ether compound containing trifluoro methyl pyridine

A technology of trifluoromethylpyridine and pyrazole oxime ether, which is applied in the field of pesticides to achieve excellent control effects

Active Publication Date: 2014-12-10
营口兴福化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 pr

Method used

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  • Preparation and application of pyrazole oxime ether compound containing trifluoro methyl pyridine
  • Preparation and application of pyrazole oxime ether compound containing trifluoro methyl pyridine
  • Preparation and application of pyrazole oxime ether compound containing trifluoro methyl pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of Compound Ia (R=2,3-F 2 )

[0035]

[0036] Add 5mmol of pyrazole oxime intermediate IIa, 5mmol of 2-(4-chloromethyl)-phenoxy-5-trifluoromethylpyridine and 20mL of acetonitrile in the reaction flask, drop 7.5mmol of cesium carbonate into it under stirring, and The resulting mixture was heated to reflux for 16 hours. Turn off heat. Filtrate, concentrate the mother liquor to dryness, mix the sample with silica gel and load it into a column for separation and purification to obtain the target compound Ia. White solid, yield 43.6%, 1 H NMR (400 MHz, CDCl 3 ): δ8.45(s,1H,Py-H),7.91(d,J=8.8Hz,1H,Py-H),7.85(s,1H,CH=N),7.36(d,J=8.0Hz ,2H,Ar-H and Py-H),7.11(d,J=8.0Hz,2H,Ar-H),7.02(d,J=8.4Hz,1H,Ar-H),6.93~6.97(m, 2H, ArH), 6.54(d, J=8.4Hz, 1H, Ar-H), 5.00(s, 2H, CH 2 ),3.68(s,3H,N-CH 3 ),2.36(s,3H,CH 3 ).

Embodiment 2

[0038] Synthesis of compound Ib (referring to the synthesis of compound Ia, wherein R=4-CH 3 )

[0039]

[0040] Add 3 mmol of pyrazole oxime intermediate IIb, 2.7 mmol of 2-(4-chloromethyl)-phenoxy-5-trifluoromethylpyridine intermediate III and 20 mL of DMF into the reaction flask, and add 8 mmol of carbonic acid into it under stirring. Potassium, the resulting mixture was heated to reflux for 20 hours. Turn off heat. After filtration, the mother liquor was concentrated to dryness, mixed with silica gel and packed into a column for separation and purification to obtain the target substance Ib. White solid, yield 50.5%, 1 H NMR (400MHz, CDCl 3 ): δ8.46(s,1H,Py-H),7.90(d,J=8.4Hz,1H,Py-H),7.84(s,1H,CH=N),7.39(d,J=7.6Hz ,2H,Ar-H and Py-H),7.12(d,J=7.2Hz,4H,Ar-H),7.01(d,J=8.4Hz,1H,Ar-H),6.81(d,J= 7.6Hz, 2H, Ar-H), 5.05(s, 2H, CH2), 3.61(s, 3H, N-CH 3 ),2.40(s,3H,CH 3 ),2.32(s,3H,CH 3 ).

Embodiment 3

[0042] Synthesis of compound Ic (referring to the synthesis of compound Ia, wherein R=H)

[0043]

[0044] Add 2 mmol of pyrazole oxime intermediate IIc, 2.2 mol of 2-(4-chloromethyl)-phenoxy-5-trifluoromethylpyridine intermediate III and 30 mL of DMSO into the reaction flask, and add 10 mmol of di isopropylethylamine (DIEA), and the resulting mixture was heated to 100° C. for 10 hours. Turn off heat. Filtration, concentrating the mother liquor to dryness, mixing with silica gel and packing into a column for separation and purification to obtain the target object Ic, a white solid, with a yield of 43.8%. 1 H NMR (400MHz, CDCl 3):δ8.46(s,1H,Py-H),7.91(d,J=8.4Hz,1H,Py-H),7.84(s,1H,CH=N),7.34~7.39(m,4H, Py-H and ArH), 7.01~7.12(m, 4H, ArH), 6.92(d, J=7.6Hz, 2H, Ar-H), 5.03(s, 2H, CH 2 ),3.63(s,3H,N-CH 3 ),2.40(s,3H,CH 3 ).

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Abstract

The invention relates to preparation and application of a pyrazole oxime ether compound (I) containing trifluoro methyl pyridine. The pyrazole oxime ether compound is prepared by carrying out condensation on pyrazole-containing hydroxamic acid (II) and 2-(4-chloromethyl phenoxyl)-5-trifluoro methyl pyridine (III). The pyrazole oxime ether compound (I) containing trifluoro methyl pyridine has an effective controlling effect on harmful insects and can be used for preparing insecticides for the fields of agriculture, horticulture and the like. A general formula of the pyrazole oxime ether compound (I) is shown in the specification.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a pyrazole oxime ether compound containing trifluoromethylpyridine, 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] The pyrazole oxime ether structure is a common class of insecticide active fragments, and its representative compounds are such as pyraclofen: [0004] [0005] The pyridine segment containing trifluoromethyl is also an important active segmen...

Claims

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Application Information

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IPC IPC(8): C07D401/12A01N43/40A01P7/04A01P7/02
CPCA01N43/40C07D401/12
Inventor 戴红石玉军施磊张海军曹宇锋王森林李刚李阳方源
Owner 营口兴福化工有限公司
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