CN108640875B - Pyrazole amide compound and preparation method and application thereof - Google Patents
Pyrazole amide compound and preparation method and application thereof Download PDFInfo
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- CN108640875B CN108640875B CN201810786548.1A CN201810786548A CN108640875B CN 108640875 B CN108640875 B CN 108640875B CN 201810786548 A CN201810786548 A CN 201810786548A CN 108640875 B CN108640875 B CN 108640875B
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- pyrazole
- pyrazole amide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- Chemical & Material Sciences (AREA)
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention provides a pyrazole amide compound and a preparation method and application thereof, wherein the chemical name of the pyrazole amide compound is (N- (4- (tert-butyl) benzyl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-formamide), and the pyrazole amide compound is prepared by reacting 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid with 4-tert-butylbenzylamine in an EDCl, HOBt, triethylamine and dichloromethane system, washing, drying, desolventizing and performing crude product column chromatography. The compound has herbicidal activity, can be used independently, can also be used together with other active compounds, is used for preventing and controlling common weeds in agriculture, provides a new choice for herbicides, and has potential application prospects.
Description
Technical Field
The invention relates to a novel herbicide, in particular to a pyrazole amide compound and a preparation method and application thereof.
Background
Pyrazole amide compounds have insecticidal and bactericidal activity, and currently, in the field of bactericides, a plurality of bactericide varieties with SDHI targets are sold on the market, such as fluxapyroxad, bixafen and benzovindiflupyr.
Schrenming et al [ CN106336380A ] reported the synthesis of compounds A1 and A2, which have preventive and therapeutic effects on cucumber powdery mildew and rice sheath blight disease.
Yanguangfu et al (WO 2015058444) synthesized pyrazole 4-carboxamide compound A3 containing difluoromethyl, which has certain therapeutic effect on rice sheath blight.
At present, in the field of herbicides, few pyrazole amide compounds are reported, and the development of novel pyrazole amide compounds and application thereof in the aspect of herbicides have important significance.
Disclosure of Invention
An object of the present invention is to provide a novel pyrazole amide compound or a pharmaceutically acceptable salt thereof.
The invention also provides a preparation method of the pyrazole amide compound or the pharmaceutically acceptable salt thereof.
The invention also provides application of the pyrazole amide compound or the pharmaceutically acceptable salt thereof in herbicides.
The fourth object of the present invention is to provide a pesticidal composition containing the above pyrazole amide compound or a pharmaceutically acceptable salt thereof as an active ingredient.
One of the objects of the invention is achieved by:
a pyrazole amide compound or a pharmaceutically acceptable salt thereof has a chemical structural formula shown as a formula (I):
the chemical name is (N- (4- (tert-butyl) benzyl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide).
The second purpose of the invention is realized by the following steps:
a preparation method of pyrazole amide compounds or pharmaceutically acceptable salts thereof comprises the following steps of reacting 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid with 4-tert-butylbenzylamine in a system of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCl), 1-hydroxybenzotriazole (HOBt), triethylamine and dichloromethane, washing, drying, desolventizing and performing crude column chromatography to obtain the pyrazole amide compounds shown in the formula (I), wherein the reaction formula is as follows:
the third purpose of the invention is realized by the following steps:
the pyrazole amide compound shown in the formula (I) or the pharmaceutically acceptable salt thereof has herbicidal activity on common agricultural weeds such as large crabgrass, eleusine indica, descurainia sophia, shepherd's purse, chenopodium quinoa and the like, and can be used independently or used together with other compounds with herbicidal activity. The compound having herbicidal activity may be a compound known to have herbicidal activity.
The fourth purpose of the invention is realized by the following steps:
a pesticide composition comprises an active component and an agriculturally acceptable carrier, wherein the active component comprises a pyrazole amide compound shown in a formula (I) or a pharmaceutically acceptable salt thereof. The carrier can be the existing carrier commonly used in agriculture.
The novel pyrazole amide compound prepared by the invention has herbicidal activity on common agricultural weeds, can be used alone or combined with other active substances with herbicidal activity, and improves the comprehensive performance of the product; the herbicide composition has low toxicity to beneficial organisms, is easy to degrade and has good environmental compatibility, provides a new choice for a new variety of creative herbicides, and has potential industrial application prospects.
Detailed Description
The invention is further illustrated by the following examples, which are given by way of illustration only and are not intended to limit the scope of the invention in any way.
Procedures and methods not described in detail in the following examples are conventional methods well known in the art, and the reagents used in the examples are either analytically or chemically pure and are either commercially available or prepared by methods well known to those of ordinary skill in the art. The following examples all achieve the objects of the present invention.
EXAMPLE 1 preparation of Compounds of formula I
1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (0.176, 1.0 mmol) and 4-tert-butylbenzylamine (0.163 g, 1.0 mmol) were dissolved in 30 ml of dichloromethane, to which Et was added3N (0.202 g, 2.0 mmol), followed by the addition of 1- (3-dimethylamino)Propyl) -3-ethylcarbodiimide hydrochloride (EDCl) (0.287 mg, 1.5 mmol), 1-hydroxybenzotriazole (HOBt) (0.20 g, 1.5 mmol), 25oC reaction for 2 h, T L C detection reaction is complete, reaction liquid is washed by water (20 ml x 2), saturated saline solution is washed by water (20 ml x 1), anhydrous sodium sulfate is dried and desolventized, crude product column chromatography is carried out to obtain white solid, yield is 80%, m.p.93-95%oC。
1HNMR(400MHz,CDCl3):3.90(s,3H,CH3),4.60(d,J=5.6Hz,2H,CH2),6.70(s,1H,NH),6.90(t,J=54.4Hz,HCF2),7.30(s,1H,CH),7.40(d,J=8.4Hz,Ph),7.63(d,J=8.4Hz,Ph),7.98(s,1H,CH)。
Example 2 herbicidal Activity testing of Compounds of formula I
The test method comprises the following steps: preparation of the compound: weighing a certain mass of the compound of the formula I by using an analytical balance (0.0001 g), preparing 1.0-5.0% of mother liquor by using 1% of DMF of Tween-80 emulsifier, and then diluting the mother liquor by using distilled water for later use.
Potting method (screening compound): a flowerpot with the inner diameter of 6cm is taken, a flowerpot with the inner diameter of 7.5 cm is taken, composite soil (garden soil: seedling culture medium, 1: 2, v/v) is filled to 3/4, and five weed targets are directly sown: the crabgrass, goosegrass herb, descurainia sophia, shepherd's purse and gooseberry (the bud ratio is more than or equal to 85 percent), the soil is covered by 0.2 cm, the weeds are reserved when the weeds grow to about 3-leaf stage, and the weeds are sprayed after the soil before the seedlings are treated and planted. The formula I compound is according to 2000 ga.i./hm2After the weed foliage liquid medicine is dried after the weed foliage liquid medicine is applied to an automatic spraying tower (model: 3 WPSH-700E), the weed foliage liquid medicine is moved to a greenhouse for culture, and the result is investigated after 35 days.
And (4) common screening results: the dosage of the compound is 2000 ga.i/hm through a herbicide activity common sieve2In the meantime, the stems and leaves and the soil were treated, and the general screening results are shown in Table 1.
TABLE 1 herbicidal Activity of Compounds of formula I
The compound of formula I is present at 2000g a.i/hm2Has certain control effect on the tested weeds under the dosage, and the herbicide composition has the advantages of high effect, low cost, no toxicity, no side effect and no side effectThe inhibition rate of the herbicide on the soil treatment of the goosegrass herb reaches 64.49%, and the herbicide can be used as a candidate compound of the herbicide.
Claims (5)
1. A pyrazole amide compound or a pharmaceutically acceptable salt thereof, characterized in that the chemical structural formula is shown as formula (I):
(I)。
2. the preparation method of pyrazole amide compounds according to claim 1, characterized in that 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid and 4-tert-butylbenzylamine are reacted in a system of EDCl, HOBt, triethylamine and dichloromethane, and the pyrazole amide compounds represented by formula (I) can be obtained by washing, drying, desolventizing and crude column chromatography.
3. The pyrazole amide compound or a pharmaceutically acceptable salt thereof according to claim 1, for use as a herbicide.
4. The use of a pyrazole amide compound or a pharmaceutically acceptable salt thereof as claimed in claim 3 as a herbicide, wherein the pyrazole amide compound represented by the formula (I) is used alone.
5. A pesticidal composition, which comprises an active ingredient comprising the pyrazole amide-based compound represented by the formula (I) of claim 1 or a pharmaceutically acceptable salt thereof, and an agriculturally acceptable carrier.
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| CN201810786548.1A CN108640875B (en) | 2018-07-17 | 2018-07-17 | Pyrazole amide compound and preparation method and application thereof |
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| CN108640875A CN108640875A (en) | 2018-10-12 |
| CN108640875B true CN108640875B (en) | 2020-07-14 |
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