CN111269223B - Isoxazole oxime ester derivative and application thereof - Google Patents
Isoxazole oxime ester derivative and application thereof Download PDFInfo
- Publication number
- CN111269223B CN111269223B CN202010266132.4A CN202010266132A CN111269223B CN 111269223 B CN111269223 B CN 111269223B CN 202010266132 A CN202010266132 A CN 202010266132A CN 111269223 B CN111269223 B CN 111269223B
- Authority
- CN
- China
- Prior art keywords
- isoxazole
- methyl
- reaction
- oxy
- benzaldehyde oxime
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Abstract
The invention discloses a 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxygen radical) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl]An ester derivative having the general formula I, wherein X represents: chlorine, fluorine, nitro, hydrogen, methyl, methoxy. The compound has remarkable inhibiting effect on 6 weeds of barnyard grass, pond, green bristlegrass, abutilon, leaf mustard and descurainia sophia, and can be used as an active ingredient of herbicide.
Description
Technical Field
The invention belongs to the field of herbicides, and particularly relates to a 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative and an active component with a weeding effect.
Background
Due to the diversity of the molecular structure and the wide biological activity of the nitrogen heterocyclic compound, and the advantages of high efficiency, low toxicity, environmental friendliness and the like, the nitrogen heterocyclic compound has become one of the hot spots for research in the field of new pesticide preparation. Among them, isoxazoles and pyrimidines are particularly widely used as herbicides, bactericides, insecticides and acaricides. In addition, many derivatives having oxime carboxylate functional groups among many pesticidal functional groups have excellent biological activities such as weeding and pest killing. Such as the carbamate pesticides such as cotton-fruit-tree, methomyl, cotton-fruit-tree, phosphocarb and the like, which all have carboxylic acid oxime ester subunits. Well known herbicide varieties such as the herbicides trifluobexime and pyribenzoxim, also have oxime carboxylate subunits. It follows that the incorporation of oxime carboxylate subunits is also considered an effective strategy in the design of pesticide active compound backbones.
In view of the background, the principle of active substructure splicing is adopted to reasonably splice the isoxazole, pyrimidine ether and oxime carboxylate so as to obtain a pesticide candidate variety or lead compound with pesticide activity, particularly herbicidal activity, which is certainly one of hot spots created by current new pesticides. In addition, due to the long-term and large-scale use of the existing herbicide, the sensitivity of agricultural weeds to the existing commercial herbicide is reduced, so that the resistance problem faced by a plurality of herbicide varieties at present is increasingly outstanding, and the development of more herbicide varieties with novel structures becomes an important way for solving the resistance problem.
Disclosure of Invention
Aiming at the problems existing in the prior art, the invention provides a 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative with herbicidal activity and application thereof; the compounds can be used as active components with weeding effect and applied to the field of herbicides, enriches the types of nitrogen heterocyclic herbicides, and can effectively relieve the problem of increasingly serious drug resistance.
The invention provides a 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxygen group) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative, the structural general formula of which is shown as I:
in formula I, R represents: chlorine, fluorine, nitro, hydrogen, methyl, methoxy;
the preparation route of the 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative is shown in the following formula:
wherein X represents: chlorine, fluorine, nitro, hydrogen, methyl, methoxy;
the preparation method of the 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxygen group) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative comprises the following steps:
(1) Preparation of 2/4- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde a
Sequentially adding salicylaldehyde, 4, 6-dimethoxy-2-methylsulfonyl pyrimidine, potassium carbonate powder and solvent DMF into a three-necked bottle provided with a reflux condenser, gradually heating to 60 ℃, stirring and reacting for 1-3 h, and carrying out TLC tracking reaction to the end point. Stopping the reaction, transferring the reaction system into a proper amount of water while the reaction system is hot, and fully stirring the water to separate out white or pale yellow solid; the same method can prepare 4- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde which is directly used for the next reaction without purification. Wherein 10mmol of aldehyde is added with 10mmol of 4, 6-dimethoxy-2-methylsulfonyl pyrimidine, 20mmol of potassium carbonate and 30ml of DMF and 100ml of water.
(2) Preparation of 2/4- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime b
Sequentially adding the 2- (4, 6-dimethoxy pyrimidine-2-oxyl) benzaldehyde a prepared by the reaction in the previous step into a reaction bottle, adding a proper amount of ethanol, fully stirring at room temperature of 20 ℃, adding an aqueous solution of hydroxylamine hydrochloride in batches after complete dissolution, and detecting the reaction until the raw materials disappear by TLC after the addition, namely stopping the reaction. Removing ethanol, suction filtering, washing the filter cake for multiple times, and drying to obtain white powder, namely 2- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime; in the same manner, 4- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime can be prepared. Wherein the feed ratio was 5mmol of 2- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde in 20ml of an aqueous solution of 10ml of ethanol and 6mmol of hydroxylamine hydrochloride.
(3) Preparation of 2 (4) - (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-carbonyl ] ester I
Adding the 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxyl) benzaldehyde oxime b prepared by the previous reaction into a three-necked bottle provided with a drying tube, slowly dropwise adding a dichloromethane solution of 3-aryl-5-methyl-isoxazole-4-formyl chloride c under the ice bath condition, stirring the mixture fully at room temperature for reaction after the dropwise adding, and carrying out TLC tracking reaction for about 1 hour. The reaction was stopped, the system was washed with saturated brine to neutrality, and the aqueous phase was extracted with dichloromethane, and the organic phases were combined. And (3) drying the mixture over night with anhydrous sodium sulfate, filtering out the sodium sulfate, and removing dichloromethane by a rotary evaporator to obtain a crude product. Recrystallizing with ethanol to obtain the final product. Wherein the feed ratio was 1mmol of 2 (4) - (4, 6-dimethoxypyrimidine-2-oxo) benzaldehyde oxime, 10ml of dichloromethane, 1.5mmol of triethylamine, 1.2mmol of 3-aryl-5-methyl-isoxazole-4-carboxylic acid chloride in 15ml of dichloromethane.
The application of the 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative disclosed by the invention is that a greenhouse potting method weeding activity test method is utilized, weeding activity evaluation is carried out on 5 weeds of barnyard grass, pond, green bristlegrass, abutilon and descurainia sophia according to an activity evaluation standard of pesticide biological activity evaluation SOP, and the result shows that part of the compound with the structural formula I has a remarkable inhibition effect on the 5 weeds of barnyard grass, pond, green bristlegrass, abutilon and descurainia sophia and can be used as an effective ingredient of a herbicide.
The invention has the beneficial effects that:
the 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative has 70-100% of weeding activity on 6 weeds of barnyard grass, pond, green bristlegrass, abutilon, leaf mustard and descurainia sophia under the condition of 450gai/ha, can be used as an active ingredient of herbicide, enriches the variety of heterocyclic herbicides, and can effectively relieve the problem of increasingly serious drug resistance.
Detailed Description
The process for the preparation of the compounds of formula I according to the invention is described in detail by way of the examples which are given only for illustration and not for limitation.
Example 1
I-1:2- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (3-chlorophenyl) isoxazole-4-carbonyl ] ester
(1) Preparation of 2- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde a
To a 100ml three-necked flask equipped with a reflux condenser, (10 mmol) of salicylaldehyde, (10 mmol) of 4, 6-dimethoxy-2-methylsulfonyl pyrimidine, (20 mmol) of potassium carbonate powder and 30ml of DMF were sequentially added, the mixture was gradually heated to 60℃and stirred for 1 to 3 hours, and TLC followed by reaction to the end point. Stopping the reaction, transferring the reaction system into 100ml of water while the reaction system is hot, fully stirring the reaction system, and separating out 2.1g of white or pale yellow solid, wherein the yield is 81%, and the temperature is between m.p.75 and 76 ℃; the product is directly used for the next reaction without purification.
(2) Preparation of 2- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime b
To a 50ml single bottle, sequentially adding (5 mmol) of 2- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde 10a-1, adding 10ml of ethanol, stirring thoroughly at room temperature and 20 ℃, after complete dissolution, adding (6 mmol) of hydroxylamine hydrochloride in 20ml of water solution in batches, and after the addition, detecting the reaction until the raw material disappears by TLC, namely stopping the reaction. After removing ethanol, carrying out suction filtration, washing a filter cake for multiple times, and drying to obtain 1.3g of white powder, wherein the yield is 90%, and the temperature is m.p.117-118 ℃;
(3) Preparation of 2- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-carbonyl ] ester I
To a 50ml three-necked flask equipped with a dry tube, 10b of (1 mmol) intermediate 2- (4, 6-dimethoxypyrimidine-2-oxo) benzaldehyde oxime, 10ml of dichloromethane and 1.5mmol of triethylamine were added, 15ml of (1.2 mmol) intermediate 3-aryl-5-methyl-isoxazole-4-carbonyl chloride solution of dichloromethane was slowly added dropwise under ice bath conditions, the dropwise addition was completed, the reaction was transferred to room temperature with stirring, and the reaction was followed by TLC for about 1 hour. The reaction was stopped, the system was washed with saturated brine to neutrality, and the aqueous phase was extracted with dichloromethane, and the organic phases were combined. And (3) drying the mixture over night with anhydrous sodium sulfate, filtering out the sodium sulfate, and removing dichloromethane by a rotary evaporator to obtain a crude product. Recrystallizing with ethanol to obtain the final product. The yield is 75 percent, and the melting point is 130-132 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.81(s,3H,- 3 CH),3.80(s,3H+3H,-O 3 CH,-O 3 CH),5.84(s,1H),7.18～8.12(m,8H,ArH),8.32(s,1H,-CH＝N-)；
13 C NMR(100MHz,CDCl 3 ):δ13.81,54.37,85.39,106.77,122.86,123.19,125.98,127.44,127.73,129.32,130.01,130.06,133.01,134.08,152.29,152.34,159.23,161.11,163.88,173.02,177.27；MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 ClN 4 O 6 :C,58.25；H,3.87；N,11.32；Found:C,58.40；H,4.11；N,11.66.
Compounds I-2 to I-4 are prepared in a similar manner to compound I-1.
IX-2:2- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (4-chlorophenyl) isoxazole-4-carbonyl ] ester
Yield 78%, melting point 141-142 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.79(s,3H,- 3 CH),3.82(s,3H+3H,-O 3 CH,-O 3 CH),5.84(s,1H),7.20～8.12(m,8H,ArH),8.43(s,1H,-CH＝N-)；
MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 ClN 4 O 6 C,58.25; h,3.87; n,11.32; found, C,58.29; h,4.27; n,11.40.ix-3:2- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime-O- [ 5-methyl-3- (2-chloro-4-chlorophenyl) isoxazole-4-carbonyl]Esters of
The yield is 82 percent, and the melting point is 124-126 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.78(s,3H,- 3 CH),3.82(s,3H+3H,-O 3 CH,-O 3 CH),5.85(s,1H),7.20-7.80(m,7H,ArH),8.39(s,1H,-CH＝N-)；
MS(EI)(m/z):528(M + )；
Anal.Calcd for C 24 H 18 Cl 2 N 4 O 6 :C,54.46；H,3.43；N,10.58；Found:C,54.61；H,3.71；N,10.79.
IX-4:2- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (2-chlorophenyl) isoxazole-4-carbonyl ] ester
Yield 81%, melting point 137-139 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.82(s,3H,- 3 CH),3.83(s,3H+3H,-O 3 CH,-O 3 CH),5.87(s,1H),7.15～8.09(m,8H+1H,ArH,-CH＝N-)；
MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 ClN 4 O 6 :C,58.25；H,3.87；N,11.32；Found:C,58.40；H,3.90；N,11.67
Example 2
I-5:4- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (2-chloro-4-chlorophenyl) isoxazole-4-carbonyl ] ester
(1) Preparation of 4- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde a
To a 100ml three-necked flask equipped with a reflux condenser, (10 mmol) of salicylaldehyde, (10 mmol) of 4, 6-dimethoxy-2-methylsulfonyl pyrimidine, (20 mmol) of potassium carbonate powder and 30ml of DMF were sequentially added, the mixture was gradually heated to 60℃and stirred for 1 to 3 hours, and TLC followed by reaction to the end point. Stopping the reaction, transferring the reaction system into 100ml of water while the reaction system is hot, fully stirring the reaction system, precipitating white or pale yellow solid, and directly using the reaction system for the next reaction without purification, wherein the yield is 92 percent, and the temperature is m.p.91-92 ℃.
(2) Preparation of 4- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime b
To a 50ml single bottle, sequentially adding (5 mmol) of 2- (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde 10a-1, adding 10ml of ethanol, stirring thoroughly at room temperature and 20 ℃, after complete dissolution, adding (6 mmol) of hydroxylamine hydrochloride in 20ml of water solution in batches, and after the addition, detecting the reaction until the raw material disappears by TLC, namely stopping the reaction. After ethanol is removed, the filter cake is filtered by suction and washed for multiple times, and white powder is obtained after drying, and the yield is 89%.
(3) Preparation of 4- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-carbonyl ] ester I
To a 50ml three-necked flask equipped with a dry tube, 10b (1 mmol) of intermediate 4- (4, 6-dimethoxypyrimidine-2-oxy) benzaldehyde oxime, 10ml of dichloromethane and 1.5mmol of triethylamine were added, 15ml (1.2 mmol) of intermediate 3-aryl-5-methyl-isoxazole-4-carbonyl chloride c in dichloromethane was slowly added dropwise under ice bath conditions, the dropwise addition was completed, the reaction was transferred to room temperature with stirring, and the reaction was followed by TLC for about 1 hour. The reaction was stopped, the system was washed with saturated brine to neutrality, and the aqueous phase was extracted with dichloromethane, and the organic phases were combined. And (3) drying the mixture over night with anhydrous sodium sulfate, filtering out the sodium sulfate, and removing dichloromethane by a rotary evaporator to obtain a crude product. Recrystallizing with ethanol to obtain the final product. The yield is 82 percent, and the melting point is 158-161 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.77(s,3H,- 3 CH),3.74(s,3H+3H,-O 3 CH,-O 3 CH),5.75(s,1H),7.20-7.80(m,7H,ArH),8.41(s,1H,-CH＝N-)；
MS(EI)(m/z):528(M + )；
Anal.Calcd for C 24 H 18 Cl 2 N 4 O 6 C,54.46; h,3.43; n,10.58; found, C,54.79; h,3.51; n,10.99. Compounds I-6 to I-8 were all prepared according to a similar procedure to Compound I-5.
I-6:4- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (2-chlorophenyl) isoxazole-4-carbonyl ] ester
The yield is 71 percent, and the melting point is 119 to 121 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.88(s,3H,- 3 CH),3.84(s,3H+3H,-O 3 CH,-O 3 CH),5.82(s,1H),7.25～7.76(m,8H,ArH),8.02(s,1H,-CH＝N-)；
MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 Cl 1 N 4 O 6 :C,58.25；H,3.87；N,11.32；Found:C,58.77；H,3.88；N,11.49.
I-7- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (4-chlorophenyl) isoxazole-4-carbonyl ] ester
The yield is 69 percent, and the melting point is 155-157 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.85(s,3H,-CH 3 ),3.81(s,3H+3H,-O 3 CH,-O 3 CH),5.83(s,1H),7.21～8.09(m,8H,ArH),8.39(s,1H,-CH＝N-)；
MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 Cl 1 N 4 O 6 :C,58.25；H,3.87；N,11.32；Found:C,58.39；H,4.07；N,11.59.
I-8:4- (4, 6-Dimethoxypyrimidin-2-oxy) benzaldehyde oxime-O- [ 5-methyl-3- (4-chlorophenyl) isoxazole-4-carbonyl ] ester
Yield 77%, melting point 143-145 ℃.
1 H NMR(CDCl 3 ,400MHz)δ2.77(s,3H,- 3 CH),3.75(s,3H+3H,-O 3 CH,-O 3 CH),5.74(s,1H),7.20-7.70(m,8H,ArH),8.06(s,1H,-CH＝N-)；
13 C NMR(100MHz,CDCl 3 ):δ13.67,54.29,85.15,106.62,122.36,122.68,126.30,127.63,129.30,129.52,130.03,133.48,133.89,155.64,156.00,159.19,160.92,163.41,172.79,177.18；MS(EI)(m/z):494(M + )；
Anal.Calcd for C 24 H 19 ClN 4 O 6 :C,58.25；H,3.87；N,11.32；Found:C,58.37；H,3.93；N,11.51.
Pot method herbicidal activity inhibition experiment of 2 (4) - (4, 6-dimethoxy pyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-formyl ] ester derivative
Test agent: weighing a certain mass of crude drugs by an analytical balance, and adding an emulsifying agent (Tween-80) and a solvent (DMF or DMSO or water) to prepare a small emulsifiable concentrate preparation or aqueous solution with the concentration of 1.0-5.0%. Then diluted with distilled water to a concentration of 450gai/ha for further use.
Test harrow mark: the test targets of the compounds (numbered 1-8) are barnyard grass, crab grass, green bristlegrass, leaf mustard, abutilon and descurainia sophia.
Culturing a test material: the test soil is garden soil, mountain soil and purchased decomposed organic soil collected from the unused land, which are prepared according to the volume ratio of 1:1:1, and the test soil is used as the special soil for the test after being uniformly mixed and stirred. Flower pots with diameters of 9.5cm and depths of 8cm are respectively taken, and 3/4 of the flower pot is filled with soil. After the soil is fully moistened, sowing broadleaf weeds and grass weed seeds into the pot, ensuring 10-15 seeds for each weed, covering 1-3 cm thick sand-mixing fine soil after sowing, discharging accumulated water at the bottom of the flowerpot after the soil in the flowerpot is saturated with water, and then placing the flowerpot in a greenhouse for culture and growth. The water is replenished every day, so that the soil humidity is kept at about 80% RH, the growth temperature is 15-30 ℃, and the air humidity is more than 50%. And when the grass weeds grow to 2-leaf stage and broadleaf weed is in true leaf stage, spraying the stems and leaves after the buds are formed. The pre-emergence treatment was planted 2 days before spraying, and soil treatment was performed before emergence of weeds.
The test method comprises the following steps: the weed seeds to be tested are respectively and evenly sown into pot with inner diameter of 9cm, and are cultivated in a greenhouse. When monocotyledonous weeds grow to 1-1.5 leaf stage and dicotyledonous weeds grow to true leaf stage, spraying the stem and leaf after the bud on an automatic spraying device. And repeating the treatment for 3 times, setting a blank control, standing for 4-5 hours after the treatment, and transferring the leaves into a greenhouse for cultivation after the liquid medicine on the leaves is dried. Plant growth was observed daily, signs of injury were recorded periodically, and the combined herbicidal activity was visually investigated 25 days after the drug, respectively.
Evaluation criteria: the result investigation adopts a visual method to evaluate the influence degree of the medicament on plant growth inhibition, deformity, yellowing, decay, necrosis and the like by visual inspection, and then the weeding activity is evaluated by visual inspection according to a comprehensive damage degree by a 0-100% grading method. The evaluation criteria are specifically shown in Table 1. The evaluation results are shown in Table 2.
TABLE 1 evaluation criteria for herbicidal Activity visual inspection
Table 2 herbicidal activity data (percentage) for Compounds I-1 to I-8
Claims (2)
1. A 2- (4, 6-dimethoxypyrimidine-2-oxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-carbonyl ] ester derivative characterized by the structural formula represented by the derivative:
2. the use of 2- (4, 6-dimethoxypyrimidin-2-yloxy) benzaldehyde oxime-O- [ 3-aryl-5-methyl-isoxazole-4-yl ] ester derivative according to claim 1, characterized in that the compound has a remarkable inhibitory effect on 5 weeds of barnyard grass, mare, green bristlegrass, abutilon and leaf mustard, and the compound I-2 has a remarkable inhibitory effect on myrtle and is useful as an active ingredient of a herbicide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010266132.4A CN111269223B (en) | 2020-04-07 | 2020-04-07 | Isoxazole oxime ester derivative and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010266132.4A CN111269223B (en) | 2020-04-07 | 2020-04-07 | Isoxazole oxime ester derivative and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111269223A CN111269223A (en) | 2020-06-12 |
| CN111269223B true CN111269223B (en) | 2023-08-11 |
Family
ID=70996322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010266132.4A Active CN111269223B (en) | 2020-04-07 | 2020-04-07 | Isoxazole oxime ester derivative and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111269223B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111623A (en) * | 1993-11-13 | 1995-11-15 | 株式会社乐喜 | Novel herbicidal pyrimidine derivatives, process for preparation thereof and their use as herbicide |
| CN1245487A (en) * | 1997-01-03 | 2000-02-23 | 巴斯福股份公司 | 3-aminocarbonyl/1-aminothiocarbonyl-substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal effect |
| JP2002332269A (en) * | 2001-05-10 | 2002-11-22 | Ube Ind Ltd | Novel dialkoxyamide oxime derivative and method of producing the same |
| CN107652242A (en) * | 2017-10-09 | 2018-02-02 | 中国农业大学 | A kind of synthesis of pyrimidine salicylic acid oxime ester and the application as herbicide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2871324A1 (en) * | 2013-11-14 | 2015-05-14 | ViroCura Therapeutics, Inc. | Substituted acyloxyamidines as hcv ns3/4a inhibitors |
-
2020
- 2020-04-07 CN CN202010266132.4A patent/CN111269223B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111623A (en) * | 1993-11-13 | 1995-11-15 | 株式会社乐喜 | Novel herbicidal pyrimidine derivatives, process for preparation thereof and their use as herbicide |
| CN1245487A (en) * | 1997-01-03 | 2000-02-23 | 巴斯福股份公司 | 3-aminocarbonyl/1-aminothiocarbonyl-substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal effect |
| JP2002332269A (en) * | 2001-05-10 | 2002-11-22 | Ube Ind Ltd | Novel dialkoxyamide oxime derivative and method of producing the same |
| CN107652242A (en) * | 2017-10-09 | 2018-02-02 | 中国农业大学 | A kind of synthesis of pyrimidine salicylic acid oxime ester and the application as herbicide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111269223A (en) | 2020-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111961041B (en) | Thiotriazinone isoxazoline compound, preparation method and application thereof, protoporphyrinogen oxidase inhibitor and herbicide | |
| CN106946856B (en) | Pyrazole oxime derivative containing tetrazole biphenyl structure and preparation method and application thereof | |
| JP2854640B2 (en) | Cyclic amide derivatives and herbicides | |
| CN106432081B (en) | Preparation method and application of pyrazole oxime ether compound containing 4-chloro-3-ethyl-1-methylpyrazole structure | |
| EP0040082A1 (en) | Novel substituted oxonicotinates, their use as plant growth regulators and plant growth regulating compositions containing them | |
| CN104072455B (en) | 6-aroyl acetyl oxygen base Aurone compound and the application on pesticide thereof | |
| CN106632007B (en) | Pyridine-3-radical aryloxy phenoxy alkyl acid ester compound and application thereof | |
| CN110078673B (en) | Aryl uracil compound, preparation method thereof and pesticide composition | |
| CN111269223B (en) | Isoxazole oxime ester derivative and application thereof | |
| RU2338377C1 (en) | Method of promoting sugar beet growth by growth regulator | |
| CN110845478A (en) | Preparation and use of pyrazole formyloxime derivatives containing 1-substituted pyridyl-3-trifluoromethylpyrazole units | |
| CN110746356A (en) | Preparation method and application of difluoromethyl pyrazole oxime ester containing 3-trifluoromethyl-5-chloropyrazole structure | |
| CN107629012B (en) | Phenazine-1-carboxylic acid bisamide compound and application thereof | |
| CA1167855A (en) | Isonicotinanilide derivatives, process for preparing the same and plant growth regulator containing the same | |
| CN109232442A (en) | Acceptable salt, preparation method, herbicidal composition on aryi-uracile class compound or its Pesticide Science | |
| CN112390727B (en) | Oxime carboxylate compound and application thereof | |
| CN109867624B (en) | 3-fluoro-5-chloropyridinyloxy phenoxypropanamide compound and application thereof | |
| CN107176950B (en) | Aryloxy phenoxy propionate compound and preparation method and application thereof | |
| CN105859698A (en) | N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative | |
| CN104230762B (en) | A kind of benzenesulfonamides of phosphinylidyne-containing amine group and Synthesis and applications thereof | |
| CN115322159B (en) | (R) -2- [4- ((quinazoline-4-ketone) -2-oxygen) phenoxy ] propionate derivative and application thereof | |
| JPS59122402A (en) | Plant growth regulator composition consisting of isonicotinic acid anilide derivative and control of plant growth | |
| CN110066282B (en) | Pyrazolopyrimidinone compound and preparation method and application thereof | |
| CN110041198B (en) | Synthesis method of chalcone-containing aryloxycarboxylate compound and application of the compound in pesticide | |
| CN108059630B (en) | 6-chloro benzoxazolyl phenoxypropanamide compound and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |