CN113402512A - Preparation method of benzoxazine-4-one derivative - Google Patents
Preparation method of benzoxazine-4-one derivative Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- HTWMTDKMOSSPMU-UHFFFAOYSA-N 1,2-benzoxazin-4-one Chemical class C1=CC=C2C(=O)C=NOC2=C1 HTWMTDKMOSSPMU-UHFFFAOYSA-N 0.000 title claims description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 13
- MOXMPWAWQLBNGS-UHFFFAOYSA-N 5-bromo-2-(3-chloropyridin-2-yl)pyrazole-3-carbonyl chloride Chemical compound ClC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl MOXMPWAWQLBNGS-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 2-amino-5-chloro-3-substituted benzoic acid Chemical class 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 63
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 2
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical class NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 10
- BWAJAQXAVGEBKS-UHFFFAOYSA-N 2-[5-bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-6-chloro-3,1-benzoxazin-4-one Chemical class O1C(=O)C2=CC(Cl)=CC=C2N=C1C1=CC(Br)=NN1C1=NC=CC=C1Cl BWAJAQXAVGEBKS-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 5
- KOPXCQUAFDWYOE-UHFFFAOYSA-N 2-amino-5-chloro-3-methylbenzoic acid Chemical compound CC1=CC(Cl)=CC(C(O)=O)=C1N KOPXCQUAFDWYOE-UHFFFAOYSA-N 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 3
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- KFKMXDHAVQQNQL-UHFFFAOYSA-N 2-[5-bromo-2-(3-chloropyridin-2-yl)pyrazol-3-yl]-6,8-dichloro-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(Cl)=CC(Cl)=C2N=C1C1=CC(Br)=NN1C1=NC=CC=C1Cl KFKMXDHAVQQNQL-UHFFFAOYSA-N 0.000 description 1
- KTHTXLUIEAIGCD-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzoic acid Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(O)=O KTHTXLUIEAIGCD-UHFFFAOYSA-N 0.000 description 1
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses a preparation method of a benzoxazine-4-ketone derivative, which comprises the steps of taking 2-amino-5-chloro-3-substituted benzoic acid and 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride as raw materials in an organic solvent, adding alkali into a system, dropwise adding a sulfonyl chloride solution under a low temperature condition, heating the solution and the sulfonyl chloride solution to carry out cyclization reaction, cooling, filtering, washing and drying after the cyclization reaction is finished to obtain the benzoxazine-4-ketone derivative, namely 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-yl ] -6-chloro-4H-3 shown in a formula 3, 1-benzoxazin-4-one; in the method, the 2-amino-5-chloro-benzoic acid derivative and the 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride are used as raw materials to be directly cyclized to obtain the target product, so that the synthesis yield is high, and the three wastes are less in generation amount.
Description
Technical Field
The invention relates to a preparation method of a benzoxazine-4-one derivative, in particular to a preparation method of a 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one derivative, and belongs to the technical field of chemical synthesis.
Background
The 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one derivative is an important intermediate for synthesizing bisamide pesticide, for example, 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-8-methyl 4H-3, 1-benzoxazine-4-one is a precursor for synthesizing chlorantraniliprole.
CN1678192A discloses two synthetic methods of the benzoxazine-4-ketone derivative, wherein the benzoxazine-4-ketone derivative is prepared by the reaction of methylsulfonyl chloride, pyrazolecarboxylic acid corresponding to formula (2) and anthranilic acid of formula (1) in the presence of tertiary amine; the other is prepared by the reaction of isatoic anhydride with a corresponding structure and pyrazole acyl chloride shown in a formula (2) in pyridine or pyridine acetonitrile solvent.
The research and development of the two methods show that the method has the problems of low yield, difficult treatment of a large amount of three wastes caused by excessive use of organic base and unsuitability for industrial production.
Therefore, a low-cost, safe and efficient synthesis method for synthesizing the benzoxazine-4-one derivative is needed.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a preparation method of a benzoxazine-4-one derivative (2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one derivative) shown in a formula 3 aiming at the defects in the prior art, wherein in the method, 2-amino-5-chloro-benzoic acid derivative and 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride are used as raw materials to be directly cyclized to obtain a target product, so that the synthesis yield is high, and the three wastes are generated in a small amount.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing a benzoxazine-4-one derivative, comprising the steps of:
in an organic solvent, 2-amino-5-chloro-3-substituted benzoic acid shown in a formula 1 and 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride shown in a formula 2 are used as raw materials, alkali is added into a system, then sulfuryl chloride solution is dropwise added under a low temperature condition, a compound shown in the formula 1 and a compound shown in the formula 2 are heated and subjected to cyclization reaction, and after the cyclization reaction is finished, 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3 shown in the formula 3 is obtained through cooling, filtering, washing and drying, 1-benzoxazin-4-one; the chemical reaction formula is shown as follows:
wherein: r1 is Me or Cl.
In the above technical solution, the organic solvent is any one of acetonitrile, acetone, methyl ethyl ketone, ethyl acetate, chloroform, dichloroethane, and toluene, or a mixture of two or more thereof, preferably acetonitrile.
In the technical scheme, the mass ratio of the compound shown in the formula 2 to the organic solvent is 1: 1.5-3, and preferably 1: 2.
In the technical scheme, the molar ratio of the compound shown in the formula 1 to the compound shown in the formula 2 is 1: 0.8-1, and preferably 1: 0.95.
In the technical scheme, the alkali is any one of pyridine, 3-methylpyridine and 2-methylpyridine, and 3-methylpyridine is preferable.
In the technical scheme, the molar ratio of the alkali to the compound shown in the formula 2 is 1.5-4: 1, and preferably 2.2: 1.
In the technical scheme, the sulfonyl chloride solution refers to a solution obtained by dissolving sulfonyl chloride in a solvent; the sulfonyl chloride is any one of methanesulfonyl chloride, propanesulfonyl chloride and benzenesulfonyl chloride, and is preferably methanesulfonyl chloride; the solvent is any one or a mixture of two or more of chloroform, dichloroethane, dichloromethane, acetonitrile and ethyl acetate, and acetonitrile is preferred.
In the technical scheme, the molar ratio of the solute sulfonyl chloride in the sulfonyl chloride solution to the compound shown in the formula 2 is 1-5: 1, and preferably 1.2: 1.
In the technical scheme, the temperature of dropwise adding the sulfonyl chloride solution is-20-15 ℃, and preferably-5-10 ℃.
In the technical scheme, the cyclization reaction is carried out at the temperature of 5-35 ℃, preferably at the temperature of 25 ℃ for 2-6 h, preferably at the temperature of 2 h.
In the above technical scheme, the temperature reduction refers to reducing to 0-10 ℃, preferably to 5 ℃.
The invention has the technical effects that: the novel preparation method of 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one has the advantages of simple operation, high yield, low cost and less three wastes, and is suitable for industrial production.
Detailed Description
The following detailed description of the embodiments of the present invention is provided, but the present invention is not limited to the following descriptions:
the invention will now be illustrated with reference to specific examples:
example 1
A method for preparing 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one, comprising the steps of:
placing 10.5g (56.7mmol) of 2-amino-5-chloro-3-methylbenzoic acid and 17.3g (53.9mmol) of 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride into a flask, adding 30g of acetonitrile, adding 10g of 3-methylpyridine, cooling to 0-5 ℃, dropwise adding 10g of acetonitrile () solution containing 7.4g of methanesulfonyl chloride, after dropwise adding, raising to 25 ℃, stirring for 2H, then cooling to 0-5 ℃, stirring for 0.5H, filtering, washing a filter cake with glacial acetonitrile, and drying to obtain 23.1g of a target product, wherein the yield is 95%.
Example 2
A method for preparing 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one, comprising the steps of:
placing 10.5g (56.7mmol) of 2-amino-5-chloro-3-methylbenzoic acid and 17.3g (53.9mmol) of 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride in a flask, adding 30g of acetonitrile, adding 10g of 3-methylpyridine, cooling to 0-5 ℃, dropwise adding 10g of acetonitrile () solution containing 7.4g of methanesulfonyl chloride, after dropwise adding, raising to 25 ℃, stirring for 2H, then cooling to 0-5 ℃, stirring for 0.5H, filtering, washing a filter cake with glacial acetonitrile, and drying to obtain 22.6g of a target product, wherein the yield is 93%.
Example 3
A method for preparing 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one, comprising the steps of:
placing 10.5g (56.7mmol) of 2-amino-5-chloro-3-methylbenzoic acid and 17.3g (53.9mmol) of 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride into a flask, adding 30g of acetonitrile, adding 10g of 3-methylpyridine, cooling to 0-5 ℃, dropwise adding 10g of acetonitrile () solution containing 7.4g of methanesulfonyl chloride, after dropwise adding, raising to 25 ℃, stirring for 2H, then cooling to 0-5 ℃, stirring for 0.5H, filtering, washing a filter cake with glacial acetonitrile, and drying to obtain 23.1g of a target product, wherein the yield is 95%.
Example 4
A method for preparing 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3, 1-benzoxazine-4-one, comprising the steps of:
placing 10.5g (56.7mmol) of 2-amino-5-chloro-3-methylbenzoic acid and 17.3g (53.9mmol) of 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride into a flask, adding 30g of acetonitrile, adding 10g of 3-methylpyridine, cooling to 0-5 ℃, dropwise adding 10g of acetonitrile () solution containing 7.4g of methanesulfonyl chloride, after dropwise adding, raising to 25 ℃, stirring for 2H, then cooling to 0-5 ℃, stirring for 0.5H, filtering, washing a filter cake with glacial acetonitrile, and drying to obtain 22.9g of a target product, wherein the yield is 94%.
Example 5
A method for preparing 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6, 8-dichloro-4H-3, 1-benzoxazine-4-one, comprising the steps of:
putting 11.7g (56.7mmol) of 2-amino-3, 5-dichlorobenzoic acid and 17.3g (53.9mmol) of 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride into a flask, adding 30g of acetonitrile, adding 10g of 3-methylpyridine, cooling to 0-5 ℃, dropwise adding 10g of acetonitrile solution containing 7.4g of methanesulfonyl chloride, raising the temperature to 25 ℃ after dropwise adding, stirring for 2H, then cooling to 0-5 ℃, stirring for 0.5H, filtering, washing a filter cake with glacial acetonitrile, and drying to obtain 23.4g of a target product with the yield of 92%.
The above examples are only for illustrating the technical concept and features of the present invention, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (10)
1. A method for preparing a benzoxazine-4-one derivative, comprising the steps of:
in an organic solvent, 2-amino-5-chloro-3-substituted benzoic acid shown in a formula 1 and 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazole-5-carbonyl chloride shown in a formula 2 are used as raw materials, alkali is added into a system, then sulfuryl chloride solution is dropwise added under a low temperature condition, a compound shown in the formula 1 and a compound shown in the formula 2 are heated and subjected to cyclization reaction, and after the cyclization reaction is finished, 2- [ 3-bromo-1- (3-chloro-2-pyridyl) -1H-pyrazol-5-yl ] -6-chloro-4H-3 shown in the formula 3 is obtained through cooling, filtering, washing and drying, 1-benzoxazin-4-one; the chemical reaction formula is shown as follows:
wherein: r1 is Me or Cl.
2. The method according to claim 1, wherein the organic solvent is one or a mixture of two or more selected from acetonitrile, acetone, methyl ethyl ketone, ethyl acetate, chloroform, dichloroethane and toluene.
3. The preparation method according to claim 1, wherein the mass ratio of the compound represented by the formula 2 to the organic solvent is 1: 1.5-3.
4. The preparation method according to claim 1, wherein the molar ratio of the compound represented by the formula 1 to the compound represented by the formula 2 is 1: 0.8-1.
5. The process according to claim 1, wherein the base is any one of pyridine, 3-methylpyridine and 2-methylpyridine.
6. The preparation method according to claim 1, wherein the molar ratio of the base to the compound represented by formula 2 is 1.5 to 4: 1.
7. The preparation method according to claim 1, wherein the sulfonyl chloride solution is a solution obtained by dissolving sulfonyl chloride in a solvent; the sulfonyl chloride is any one of methanesulfonyl chloride, propanesulfonyl chloride and benzenesulfonyl chloride; the solvent is any one of chloroform, dichloroethane, dichloromethane, acetonitrile and ethyl acetate, or a mixture of two or more of the above.
8. The preparation method according to claim 1, characterized in that the molar ratio of the solute sulfonyl chloride in the sulfonyl chloride solution to the compound represented by formula 2 is 1-5: 1.
9. The process according to claim 1, wherein the cyclization reaction is carried out at a temperature of 5 ℃ to 35 ℃ for 2 hours to 6 hours.
10. The preparation method according to claim 1, wherein the sulfuryl chloride solution is dropwise added at a temperature of-20 ℃ to 15 ℃; the temperature reduction refers to reducing to 0-10 ℃.
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| CN115745959A (en) * | 2022-11-30 | 2023-03-07 | 山东友道化学有限公司 | Industrial production method of chlorantraniliprole |
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