CN111747888A - Pyridyloxyphenoxypropionamide compound with herbicidal activity and synthetic method and application thereof - Google Patents
Pyridyloxyphenoxypropionamide compound with herbicidal activity and synthetic method and application thereof Download PDFInfo
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- CN111747888A CN111747888A CN202010605054.6A CN202010605054A CN111747888A CN 111747888 A CN111747888 A CN 111747888A CN 202010605054 A CN202010605054 A CN 202010605054A CN 111747888 A CN111747888 A CN 111747888A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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Abstract
The invention discloses a pyridyloxy phenoxy propionamide compound with herbicidal activity, which is shown as a structural formula (III). The invention also discloses the application of the compound in crop weeding, preferably in preventing and killing gramineous weeds and broadleaf weeds, and more preferably in preventing and killing gramineous weeds such as barnyard grass, moleplant, crab grass and the like and broadleaf weeds in rice and wheat fields. The compound of the invention is stable under acid-base conditions, has good control performance on gramineous weeds such as barnyard grass, moleplant seed and crab grass, has small dosage, does not have any adverse effect on the normal growth of rice and wheat crops, does not need to add a safener, and is especially safe for wheat crops at low temperature.
Description
Technical Field
The invention belongs to the field of organic molecule synthesis, relates to a pyridyloxy phenoxy propionamide compound with herbicidal activity, and a synthesis method and application thereof, and particularly relates to a new compound (R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) -N- (2-fluorophenyl) -N-methylpropanamide, and a synthesis method and application thereof.
Background
Clodinafop-propargyl, chemical name: the (R) -2- [4- (5-chloro-3-fluoro-2-pyridyloxy) phenoxy ] propinyl propionate belongs to aryloxy-phenoxy-propionic acid herbicides, can effectively inhibit biosynthesis of esters, is an acetyl-coenzyme A hydroxylase inhibitor, and is a selective systemic conduction type post-seedling stem leaf treating agent. The agent is absorbed by plant leaf and leaf sheath to conduct meristem, and inhibit acetyl coenzyme A carboxylase, so as to inhibit fatty acid biosynthesis, and finally result in weed death. The drug-resistant crops are decomposed into inactive metabolites in vivo. Clodinafop-propargyl is rapidly degraded in soil into free acid phenyl and pyridine moieties which enter the soil. In addition, the clodinafop-propargyl has a certain degree of phytotoxicity and can kill crops such as wheat and the like at low temperature, so the clodinafop-propargyl must be mixed with a safener in the use process, is applied to weeding in wheat fields, and can prevent and treat gramineous weeds such as alous, oat grass, ryegrass, common bluegrass, green bristlegrass and the like. However, clodinafop-propargyl is easily hydrolyzed under alkaline conditions, and thus production and storage thereof are limited.
Therefore, there is a need for further development of herbicides having better preservation properties.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a novel compound (R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) -N- (2-fluorophenyl) -N-methylpropanamide
The purpose of the invention is realized by the following technical scheme:
a compound of formula (III):
chemical name of the compound represented by the formula (III): (R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) -N- (2-fluorophenyl) -N-methylpropanamide. English name: (R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) -N- (2-fluorophenyl) -N-methylpropanamide.
Another object of the present invention is to provide a process for producing a compound represented by the formula (III), which comprises the steps of:
step (1), carrying out chlorination reaction on a compound IV ((R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) propionic acid) and a chlorinating agent to obtain a compound I ((R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) propionyl chloride);
wherein X is a chlorinating agent;
step (2), taking the compound I and 2-fluoro-N-methylaniline as raw materials, and taking inorganic base as a catalyst to react to obtain a compound shown in a formula (III);
in the step (1), the molar ratio of the compound IV to the chlorinating agent is 1: 1.5-2, preferably 1: 1.5.
The chlorinating agent is phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, thionyl chloride or sulfuryl chloride; because the post-treatment is convenient after the thionyl chloride reaction is finished and no residue is generated, the thionyl chloride is preferably thionyl chloride.
The reaction solvent is toluene.
The molar ratio of the compound IV to the toluene is 1: 5-10, preferably 1: 7.
In the step (2), the molar ratio of the compound I to the compound II is 1: 1-1.05, and preferably 1:1.
The reaction solvent is toluene, and the molar ratio of the compound I to the toluene is 1: 3-1: 8, preferably 1: 5.
The molar ratio of the compound I to the inorganic base is 1: 3-1: 6, and preferably 1: 6.
The inorganic base is sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate and potassium carbonate, and preferably sodium hydroxide.
Specifically, the preparation method of the compound shown in the formula (III) comprises the following steps:
dissolving a compound IV in a reaction solvent at the temperature of 60-65 ℃, dropwise adding a chlorinating agent, heating to 80 ℃ after dropwise adding, and carrying out heat preservation reaction for 2 hours;
mixing a compound II, a catalyst and a reaction solvent, keeping the temperature at 20-25 ℃, dropwise adding the reaction liquid obtained in the step (1) into the mixed liquid, and reacting for 2 hours at 20-25 ℃ after dropwise adding; and (3) after the reaction is finished, filtering the reaction solution, adjusting the pH value of the filtrate to 2 by using 10% hydrochloric acid, layering, removing the solvent by rotary evaporation of an organic phase, taking hydrous ethanol as a recrystallization solvent, crystallizing at the temperature of 0-5 ℃, filtering, and drying to obtain the target product.
The hydrous ethanol is 90% ethanol.
Another object of the present invention is to provide the use of the compound represented by the formula (iii) for weeding crops, preferably for controlling grassy weeds and broadleaf weeds, more preferably for controlling grassy weeds such as barnyard grass, moleplant seeds, large crabgrass and the like and broadleaf weeds in rice and wheat fields, which have good control performance for the grassy weeds and are safe for rice and wheat, especially for wheat crops at low temperatures.
The invention also aims to provide a weeding composition which is prepared into a pesticide acceptable formulation by taking the compound shown in the formula (III) as an active ingredient or a main active ingredient and assisting with a pesticide acceptable auxiliary agent.
The mass content of the active ingredients in the weeding composition is 2-95%, and preferably 5-80%.
The skilled person can prepare the herbicidal composition into various dosage forms by known methods, for example, the active ingredients can be uniformly mixed with an auxiliary agent such as a solvent and a solid carrier, and can be uniformly mixed and ground together with a surfactant if necessary to prepare the required dosage forms, such as wettable powder, a suspending agent, a dispersible oil suspending agent, an aqueous emulsion, an emulsifiable concentrate, a water dispersible granule and the like. Depending on the nature of the herbicidal composition and the purpose and environmental conditions to which the composition is to be applied, the composition may be applied by any method selected from the group consisting of spraying, atomizing, dusting, scattering, pouring, and the like. The application method comprises the following steps: the herbicidal compositions are applied to the aerial parts, in particular to the foliage or foliar surfaces, where plants grow. The frequency of application and the amount of application depend on the biological and climatic survival conditions of the control subject. The locus of the plant, such as a paddy field, can be drenched with a liquid preparation of the composition, or the composition can be applied to the soil in solid form, such as in granular form (soil application), from where it can enter the plant through the roots of the plant (systemic action).
The above solvents may be selected from: aromatic hydrocarbons, preferably containing 8 to 12 carbon atoms, such as xylene mixtures or substituted benzenes; phthalate esters, such as dibutyl phthalate or dioctyl phthalate; aliphatic hydrocarbons such as cyclohexane or paraffin; alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol monomethyl; ketones, such as cyclohexanone; strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide; or vegetable oils, such as soybean oil.
The solid carriers mentioned above, such as those used for dusts and dispersents, are generally natural mineral fillers, such as talc, kaolin, montmorillonite or attapulgite. To manage the physical properties of the composition, it is also possible to add highly dispersible silicic acid or highly dispersible polymeric adsorbent carriers, for example granular adsorbent carriers or non-adsorbent carriers, suitable granular adsorbent carriers being porous, such as pumice, bentonite or bentonite; suitable non-adsorbent carriers are for example calcite or sand. In addition, a large number of pre-granulated materials of inorganic or organic nature, in particular dolomite, can be used as carriers.
Depending on the chemical nature of the active ingredients in the herbicidal composition according to the present invention, suitable surfactants are lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, alkaline earth metal or amine salts, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and also condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylaryl polyglycol ethers, tributyl benzene polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethylene oxide condensates, ethoxylated polyoxypropylene, lauric polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
The stability test of the compound III (shown in the table 1) is carried out by the inventor, and the pyridyloxyphenoxypropionamide compound is more stable under the acid-base condition (pH is 5-9) relative to clodinafop-propargyl.
TABLE 1 comparison of the hydrolysis rates of clodinafop-propargyl and Compound III of the invention at different pH values
Note:
pH 5: 35ml (0.2mol/L sodium hydroxide) +100ml (0.04mol/L acetic acid +0.04mol/L phosphoric acid +0.04mol/L boric acid) aqueous solution.
pH 7: 52.5ml (0.2mol/L sodium hydroxide) +100ml (0.04mol/L acetic acid +0.04mol/L phosphoric acid +0.04mol/L boric acid) aqueous solution.
pH 9: 67.7ml (0.2mol/L sodium hydroxide) +100ml (0.04mol/L acetic acid +0.04mol/L phosphoric acid +0.04mol/L boric acid) aqueous solution.
Compared with the prior art, the invention has the beneficial effects that:
the pyridyloxy phenoxy propionamide compound is stable under acidic and alkaline conditions. The pyridyloxy phenoxy propionamide compound has good control performance on gramineous weeds such as barnyard grass, moleplant seed and large crabgrass, is small in dosage, does not have any adverse effect on normal growth of rice and wheat crops, does not need to be added with a safety agent, and is especially safe for wheat crops at low temperature.
Detailed Description
Example 1
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked flask, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 119g of thionyl chloride within about 1 hour, heating to 80 ℃ after the dropwise adding is finished, and keeping the temperature for 2h to obtain a reaction solution containing the compound I.
62.5g of compound II, 230g of toluene and 120g of sodium hydroxide are added into a 2000ml three-neck flask and stirred; and (3) keeping the temperature at 20-25 ℃, dropwise adding the reaction liquid containing the compound I into the mixed liquid containing the compound II within about 1.5 hours, and after dropwise adding, keeping the temperature at 20-25 ℃ for 2 hours. And (3) after the reaction is finished, filtering to remove inorganic salt and excessive inorganic base generated in the reaction, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 196g of a compound III (white solid), wherein the content of the compound III is 96.4%, and the yield of the compound III is 93.60%.
Compound iii was identified as (R) -2- (4- ((5-chloro-3-fluoropyridin-2-yl) oxy) phenoxy) -N- (2-fluorophenyl) -N-methylpropanamide.
1H NMR(DMSO-d6,300MHz)：7.93(s,1H),7.70(d,1H),7.22(m,3H),7.13-7.15(m,5H),6.82(d,2H),4.94(dd,1H),3.42(s,3H),1.56(d,3H)。
Example 2
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked bottle, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 89.2g of thionyl chloride within about 1 hour, heating to 80 ℃ after dropwise adding, and keeping the temperature for 2h for later use.
62.5g of compound II, 230g of toluene and 120g of sodium hydroxide are added into a 2000ml three-neck flask, stirred, the temperature is kept between 20 and 25 ℃, the reaction liquid containing the compound I is dripped into the mixed liquid containing the compound II within about 1.5 hours, and heat preservation is carried out for 2 hours after dripping. And after the reaction is finished, filtering, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 202g of a finished product with the content of 98.2% and the yield of 96.46%.
Example 3
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked bottle, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 89.2g of thionyl chloride within about 1 hour, heating to 80 ℃ after dropwise adding, and keeping the temperature for 2h for later use.
62.5g of compound II, 230g of toluene and 168g of potassium hydroxide are added into a 2000ml three-neck flask, stirred, the temperature is kept between 20 and 25 ℃, the reaction liquid containing the compound I is dripped into the mixed liquid containing the compound II within about 1.5 hours, and heat preservation is carried out for 2 hours after dripping. And after the reaction is finished, filtering, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 194g of a finished product, wherein the content is 97.4%, and the yield is 92.64%.
Example 4
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked bottle, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 89.2g of thionyl chloride within about 1 hour, heating to 80 ℃ after dropwise adding, and keeping the temperature for 2h for later use.
Adding 65.7g of compound II, 230g of toluene and 120g of sodium hydroxide into a 2000ml three-neck flask, stirring, keeping the temperature at 20-25 ℃, dropwise adding the reaction solution containing the compound I into the mixed solution containing the compound II within about 1.5 hours, and preserving heat for 2 hours after dropwise adding. And after the reaction is finished, filtering, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 201g of a finished product, wherein the content of the finished product is 98.3%, and the yield of the finished product is 95.98%.
Example 5
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked bottle, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 89.2g of thionyl chloride within about 1 hour, heating to 80 ℃ after dropwise adding, and keeping the temperature for 2h for later use.
62.5g of compound II, 230g of toluene and 318g of sodium carbonate are added into a 2000ml three-neck flask, stirred, the temperature is kept between 20 and 25 ℃, the reaction liquid containing the compound I is dripped into the mixed liquid containing the compound II within about 1.5 hours, and heat preservation is carried out for 2 hours after dripping. And after the reaction is finished, filtering, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 163g of a finished product with the content of 86.2% and the yield of 77.84%.
Example 6
Adding 322g of toluene and 115.8g of compound IV into a 1000ml three-necked bottle, stirring for 30min at the temperature of 60-65 ℃, dropwise adding 89.2g of thionyl chloride within about 1 hour, heating to 80 ℃ after dropwise adding, and keeping the temperature for 2h for later use.
62.5g of compound II, 230g of toluene and 80g of sodium hydroxide are added into a 2000ml three-neck flask, stirred, the temperature is kept at 20-25 ℃, the reaction liquid containing the compound I is dripped into the mixed liquid containing the compound II within about 1.5 hours, and heat preservation is carried out for 2 hours after dripping. And after the reaction is finished, filtering, dropwise adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2, layering, carrying out rotary evaporation on an organic phase, adding 300g of 90% ethanol, crystallizing at 0-5 ℃, filtering, and drying to obtain 173g of a finished product with the content of 88.7% and the yield of 82.61%.
Example 7
15% wettable powder
15% of compound III (weight percentage, the same below), 6% of sodium lignosulfonate, 5% of alkyl sulfonate, 8% of white carbon black and kaolin, and the balance is 100%.
And (3) fully mixing the compound III with sodium lignosulfonate, alkyl sulfonate, white carbon black and kaolin according to a proportion, and crushing by using an ultrafine crusher to prepare 15% wettable powder.
Example 8
35% wettable powder
35% of compound III, 3% of bentonite, 3% of alkyl sulfonate, 5% of white carbon black and the balance of diatomite to 100%.
And (3) fully mixing the compound III with bentonite, alkyl sulfonate, white carbon black and diatomite according to a proportion, and crushing by using an ultrafine crusher to prepare 35% wettable powder.
Example 9
15% microemulsion
15% of compound III, 40% of propylene glycol, 10% of alkylaryl polyglycol ether and water, wherein the balance is up to 100%.
Example 10
Test agents: the 15% wettable powder prepared in example 7; control agents: wettable powder of 15% clodinafop-propargyl (Zhaozhenda).
As shown in Table 1, the experiment was conducted in three treatments, each of which was repeated 5 times and had an area of 20m per cell2Random block permutation.
The application is carried out in the morning at the end of 12 months for 1 time, and the stem and leaf spray method is used for uniform spraying. When the herbicide is applied, the gramineous weeds are in a 3-6 leaf stage, and the wheat is in a 6-7 leaf stage.
The number of weeds was investigated before application, and the number of residual weed plants was investigated 15d, 21d, and 45d after application. If the phytotoxicity occurs, recording the type and degree of the phytotoxicity according to the phytotoxicity grading standard. The test results are shown in Table 2.
TABLE 2 plant control and fresh weight control of the weeds for each treatment
Note: the total grass comprises grassy weeds such as barnyard grass, large crabgrass, moleplant seeds and the like and broadleaf weeds.
No obvious abnormality of the wheat in the growing period is seen in the treatment. The pyridyloxy phenoxy propionamide compound can still obtain a weeding effect similar to or better than that of clodinafop-propargyl under the condition that the application amount is reduced by half, has a wider weeding spectrum, and is more beneficial to being used in agricultural production.
Claims (10)
1. A compound of formula (III):
2. a method for synthesizing the compound of claim 1, comprising the steps of:
performing chlorination reaction on a compound IV and a chlorination reagent to obtain a compound I;
wherein X is a chlorinating agent;
step (2), taking the compound I and 2-fluoro-N-methylaniline as raw materials, and taking inorganic base as a catalyst to react to obtain a compound shown in a formula (III);
3. the method for synthesizing the compound according to claim 2, wherein the chlorinating agent is phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, thionyl chloride or sulfuryl chloride, preferably thionyl chloride.
4. The method for synthesizing the compound according to claim 2, wherein the molar ratio of the compound IV to the chlorinating agent is 1: 1.5-2, preferably 1: 1.5.
5. The method for synthesizing the compound according to claim 2, wherein in the step (1), the reaction solvent is toluene, and the molar ratio of the compound IV to the toluene is 1: 5-10, preferably 1: 7; in the step (2), the reaction solvent is toluene, and the molar ratio of the compound I to the toluene is 1: 3-1: 8, preferably 1: 5.
6. The method for synthesizing the compound according to claim 2, wherein the molar ratio of the compound I to the compound II is 1:1 to 1.05, preferably 1:1.
7. The method for synthesizing the compound according to claim 2, wherein the molar ratio of the compound I to the inorganic base is 1:3 to 1:6, preferably 1: 6.
8. The method of claim 2, wherein the inorganic base is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, and potassium carbonate, preferably sodium hydroxide.
9. Use of a compound according to claim 1 for the control of weeds in crops, preferably in grasses.
10. A herbicidal composition, characterized in that it comprises as active ingredient or as the main active ingredient, a compound according to claim 1, in addition to pesticidally acceptable adjuvants.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276275A (en) * | 2021-12-20 | 2022-04-05 | 西安近代化学研究所 | Aryloxy phenoxy propionate compound, preparation method and application |
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|---|---|---|---|---|
| US5032168A (en) * | 1987-03-18 | 1991-07-16 | Dowelanco | 4-((aryloxy)phenoxy)fluoroalkanoic acid derivatives and their herbicidal uses |
| CN104876922A (en) * | 2014-02-27 | 2015-09-02 | 南京工业大学 | Aryloxy phenoxy propionamide type herbicide |
| CN106631896A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Halogenated cyanophenyl phenoxy carboxylic acid amide compound as well as synthesis method and application thereof |
| CN106632005A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Ethyl pyridyloxyphenoxypropionate compound as well as preparation method and application thereof |
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2020
- 2020-06-29 CN CN202010605054.6A patent/CN111747888A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032168A (en) * | 1987-03-18 | 1991-07-16 | Dowelanco | 4-((aryloxy)phenoxy)fluoroalkanoic acid derivatives and their herbicidal uses |
| CN104876922A (en) * | 2014-02-27 | 2015-09-02 | 南京工业大学 | Aryloxy phenoxy propionamide type herbicide |
| CN106631896A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Halogenated cyanophenyl phenoxy carboxylic acid amide compound as well as synthesis method and application thereof |
| CN106632005A (en) * | 2016-11-29 | 2017-05-10 | 江苏富鼎化学有限公司 | Ethyl pyridyloxyphenoxypropionate compound as well as preparation method and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276275A (en) * | 2021-12-20 | 2022-04-05 | 西安近代化学研究所 | Aryloxy phenoxy propionate compound, preparation method and application |
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