Preparation method and application of pyrazole amide compound containing chloropyridine methoxy aryl structure
By synthesizing pyrazole amide compounds containing chloropyridine methoxyaryl groups, the problem of pesticide resistance has been solved, achieving highly efficient control of pests such as armyworms, and making them suitable for insecticide applications in agriculture and horticulture.
Patent Information
- Application Number
- CN202511146139.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-08-15
- Publication Date
- 2025-11-21
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
Existing pesticides have the problem of pesticide resistance when controlling pests, and there is a need to develop new, highly effective and low-toxicity insecticides.
Pyrazole amide compounds containing chloropyridine methoxyaryl groups were synthesized and applied to insecticides. They were combined with common pesticide adjuvants to form formulations such as emulsions and suspensions for application methods such as foliar spraying and soil treatment.
The compound exhibits good insecticidal effects against pests such as armyworms, making it suitable for agricultural and horticultural applications and providing highly effective pest control.
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Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the field of chemical pesticides, in particular to a preparation method and use of pyrazole amide compounds containing chloropyridine methoxy aryl structure. BACKGROUND
[0002] In recent years, pesticides play an important role in the effective prevention and control of pests. However, with the continuous use of pesticides, some pests have developed resistance to traditional pesticides. Therefore, pesticide workers need to continuously develop novel high-efficiency low-toxicity pesticides.
[0003] Pyrazole amide is an important nitrogen-containing heterocyclic unit, and pyrazole amide compounds often exhibit excellent insecticidal activity and are widely used in plant protection.
[0004] In addition, substituted pyridine rings are also important members of nitrogen-containing heterocyclic systems, and substituted pyridine compounds often exhibit good biological activity and play an important role in agricultural production.
[0005] Therefore, in order to continue to explore compounds with good insecticidal activity from pyrazole amide compounds, the substituted pyridine structure is organically connected with the pyrazole amide skeleton, and the present application discloses a pyrazole amide compound containing chloropyridine methoxy aryl structure, which has agricultural insecticidal application value. SUMMARY
[0006] The purpose of the present application is to provide pyrazole amide compounds containing chloropyridine methoxy aryl structure, which have good insecticidal effect on pests such as armyworms and are efficient, in order to meet the demand for high-efficiency insecticides in crop protection.
[0007] Another purpose of the present application is to provide a preparation method of the above-mentioned compounds.
[0008] Still another purpose of the present application is to provide the use of the above-mentioned compounds in the preparation of insecticides.
[0009] To solve the above technical problems, the first aspect of the present application provides pyrazole amide compounds containing chloropyridine methoxy aryl structure, which have the following structure:
[0010]
[0011]
[0012] The second aspect of the present application provides a preparation method of the above-mentioned pyrazole amide compounds containing chloropyridine methoxy aryl structure, characterized in that it comprises the following steps:
[0013]
[0014] The chloropyridylmethoxy arylmethylamine intermediate and the pyrazole acid intermediate are prepared by conventional synthesis methods.
[0015] The compounds of the present application have good insecticidal effect on pests such as armyworm, and thus can be used for preparing insecticides to protect plants in agriculture, horticulture and the like. Of course, the harmful organisms that can be controlled by the compounds of the present application are not limited to the above examples.
[0016] When the compounds of the present application are used as insecticides in the fields of agriculture, horticulture and the like, they can be used alone or in the form of an insecticidal composition, such as a water emulsion, a suspension, a water dispersible granule, an emulsifiable concentrate and the like, prepared by using the compounds of the present application as an active ingredient together with a conventional agricultural adjuvant.
[0017] The conventional agricultural adjuvants include: liquid carriers such as water; organic solvents such as toluene, xylene, cyclohexanol, methanol, butanol, ethylene glycol, acetone, dimethylformamide, acetic acid, dimethyl sulfoxide, animal and vegetable oils and fatty acids; conventional surface agents such as emulsifiers and dispersants, including anionic, cationic, nonionic and amphoteric surfactants; and other adjuvants such as humectants, thickeners and the like.
[0018] When the compounds of the present application are used as an active ingredient in insecticides, the content thereof in the insecticides is selected in the range of 0.1% to 99.5%, and the appropriate content of the active ingredient can be determined depending on the formulation form and the method of application. Generally, the content of the active ingredient in a water emulsion is 5% to 50% by weight, preferably 10% to 40%; and the content of the active ingredient in a suspension is 5% to 50%, preferably 5% to 40%.
[0019] For the use of the insecticides of the present application, conventional methods of application such as stem-leaf spraying, soil treatment and seed treatment can be selected. For example, when stem-leaf spraying is employed, the concentration of the compound as an active ingredient used is in the range of 1 to 1000 μg / mL, preferably 1 to 500 μg / mL, in the form of a water emulsion, a suspension, a water dispersible granule or an emulsifiable concentrate.
[0020] The pyrazole amide compounds of the present application having a chloropyridylmethoxy aryl structure have good insecticidal effect on pests such as armyworm, and thus can be used for preparing insecticides for use in the fields of agriculture, horticulture and the like. DETAILED DESCRIPTION
[0021] The above-mentioned scheme will be further described below in connection with specific examples. It should be understood that these examples are for illustrating the present application and are not intended to limit the scope of the present application. The conditions employed in the examples can be further adjusted according to the conditions of the specific manufacturer, and the conditions not mentioned are generally the conditions in conventional experiments.
[0022] Example 1:
[0023]
[0024] In a reaction flask was added 1 mmol of intermediate IIIa, 1 mmol of benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and 25 mL of N,N-dimethylformamide (DMF), stirred at room temperature for 10 min, then 3 mmol of N,N-diisopropylethylamine (DIPEA) and 1 mmol of intermediate IIa were added, and then stirred at room temperature for 12 hours. After removing the solvent, the obtained crude product was purified by silica gel column chromatography to obtain the target product Ia; 1 H NMR (400 MHz, DMSO-d6) δ 9.24 (t, J = 6.0 Hz,
[0025] 1H), 8.48 ~ 8.51 (m, 2H), 8.19 ~ 8.21 (m, 1H), 7.90 ~ 7.93 (m, 1H), 7.62 ~ 7.65 (m, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.26 (s, 1H), 6.99 (d, J = 8.4 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.76 ~ 6.78 (m, 1H),
[0026] 8.0 Hz, 1H), 7.26 (s, 1H), 6.99 (d, J = 8.4 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.76 ~ 6.78 (m, 1H),
[0027] 5.11 (s, 2H), 4.28 (d, J = 6.0 Hz, 2H), 3.74 (s, 3H).
[0028] Example 2:
[0029]
[0030] In a reaction flask was added 1 mmol of intermediate IIIa, 1 mmol of benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and 25 mL of N,N-dimethylformamide (DMF), stirred at room temperature for 10 min, then 3 mmol of N,N-diisopropylethylamine (DIPEA) and 1 mmol of intermediate IIa were added, and then stirred at room temperature for 12 hours. After removing the solvent, the obtained crude product was purified by silica gel column chromatography to obtain the target product Ia; 1HNMR (400 MHz, DMSO-d6) δ 9.28 (t, J = 6.0 Hz, IH), 8.50 ~ 8.51 (m, 2H), 8.19 ~ 8.21 (m, IH), 7.93 ~ 7.95 (m, IH), 7.62 ~ 7.66 (m, IH), 7.57 (d, J = 8.0 Hz, IH), 7.20 ~ 7.25 (m, 2H), 7.10 ~ 7.14 (m, IH), 7.03 (d, J = 8.4 Hz, IH), 5.22 (s, 2H), 4.29 (d, J = 5.6 Hz, 2H).
[0031] Example 3:
[0032]
[0033] In a reaction flask was added 2 mmol of intermediate IIIa, 2 mmol of benzotriazole-N, N, N', N'-tetramethyluronium hexafluorophosphate (HBTU) and 35 mL of dichloromethane, stirred at room temperature for 10 min, then 4 mmol of triethylamine and 3 mmol of intermediate IIc were added, and then the stirring was continued at room temperature for 11 hours. After removing the solvent, the obtained crude product was separated by silica gel column chromatography to obtain the target product Ic; 1 HNMR (400 MHz, DMSO-d6) δ 9.28 (t, J = 6.0 Hz, IH), 8.50 ~ 8.51 (m, 2H), 8.19 ~ 8.21 (m, IH), 7.93 ~ 7.95 (m, IH), 7.62 ~ 7.66 (m, IH), 7.57 (d, J = 8.0 Hz, IH), 7.20 ~ 7.25 (m, 2H), 7.10 ~ 7.14 (m, IH), 7.03 (d, J = 8.4 Hz, IH), 5.22 (s, 2H), 4.29 (d, J = 5.6 Hz, 2H).
[0034] Example 4:
[0035] Test of insecticidal activity of the compound on P. xylostella
[0036] The leaf dipping method proposed by the International Resistance Action Committee (IRAC) was used. The test object was P. xylostella, and a proper amount of corn leaves was dipped in the prepared pesticide solution, then naturally dried, placed in a culture dish lined with filter paper, and then P. xylostella 3rd instar larvae were introduced and cultured in a 25°C observation room. The results were observed after 48 hours. The insect body was touched with a brush, and no reaction was considered dead. The test concentration was 500 μg / mL.
[0037] The insecticidal activity test data of compounds la-lc are shown in Table 1. As shown in Table 1, compounds la-lc all show good insecticidal effect on armyworm, and the killing effect of compounds la, lb and lc on armyworm is 100%, 100% and 100% respectively at a test concentration of 500 μg / mL.
[0038] Table 1. Preliminary insecticidal activity data of la-lc
[0039]
[0040] The above test results show that the new compounds obtained by introducing substituted pyridine structure into pyrazole amide compound molecules all have good insecticidal effect.
[0041] The above shows and describes the basic principles, main features and advantages of the present application. Those skilled in the art should understand that the present application is not limited by the above examples, and the above examples and descriptions in the specification are only to illustrate the principles of the present application. Without departing from the spirit and scope of the present application, various changes and improvements can be made to the present application, and these changes and improvements all fall within the scope of the claimed present application. The scope of protection of the present application is defined by the appended claims and their equivalents.
Claims
1. A pyrazolamide compound (I) containing a chloropyridine methoxyaryl structure, characterized in that... The structure is as follows:
2. The method for preparing the pyrazole amide compound (I) containing a chloropyridine methoxyaryl structure as described in claim 1, characterized in that... The method is as follows:
3. Use of the pyrazole amide compound (I) containing a chloropyridine methoxyaryl structure as described in claim 1 in the preparation of insecticides.