CN114437083A - Synthetic method of thioketone - Google Patents
Synthetic method of thioketone Download PDFInfo
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- CN114437083A CN114437083A CN202210127039.4A CN202210127039A CN114437083A CN 114437083 A CN114437083 A CN 114437083A CN 202210127039 A CN202210127039 A CN 202210127039A CN 114437083 A CN114437083 A CN 114437083A
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- China
- Prior art keywords
- fluoro
- triazolo
- pyrimidine
- methoxy
- methoxypyrimidine
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- Pending
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- 238000010189 synthetic method Methods 0.000 title description 3
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 title description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 36
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- CWCLTMYHVXUXDW-UHFFFAOYSA-N (5-fluoro-2-methoxypyrimidin-4-yl)hydrazine Chemical compound COC1=NC=C(F)C(NN)=N1 CWCLTMYHVXUXDW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- BMMSPZWKTCWKBD-UHFFFAOYSA-N 8-fluoro-5-methoxy-2h-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione Chemical compound COC1=NC=C(F)C2=NNC(=S)N12 BMMSPZWKTCWKBD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000003860 storage Methods 0.000 claims abstract description 8
- 238000005086 pumping Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 3
- 238000001308 synthesis method Methods 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000005529 Florasulam Substances 0.000 description 4
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000012432 intermediate storage Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NGBMMSDIZNGAOK-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine-5-sulfonamide Chemical compound NS(=O)(=O)C1=NC=C2NN=NC2=N1 NGBMMSDIZNGAOK-UHFFFAOYSA-N 0.000 description 1
- 108010000700 Acetolactate synthase Proteins 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione, which comprises the following steps: (1) dissolving 5-fluoro-4-hydrazino-2-methoxypyrimidine in a solvent for later use; (2) putting hydrogen peroxide into a storage tank for later use; (3) placing the carbon disulfide in a storage tank for later use; (4) at a certain temperature, respectively pumping 5-fluoro-4-hydrazino-2-methoxypyrimidine solution and carbon disulfide into a microchannel reactor I by using a diaphragm metering pump to complete the reaction; (5) then pumping hydrogen peroxide into a micro-channel reactor II by using a diaphragm metering pump, and finishing the oxidation reaction; (6) the reaction liquid is centrifuged by a centrifuge to obtain 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone solution. The method has the advantages of simple operation steps, low danger, high equipment utilization rate, complete reaction, high product stability and high yield.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone.
Background
Florasulam is a triazolopyrimidine sulfonamide herbicide developed by the Dow agricultural science company in the United states, and the action mechanism of the florasulam is to inhibit the synthesis of acetolactate synthase so as to prevent the synthesis of related amino acid, so that the plants cannot synthesize protein to cause death. The florasulam is a high-efficiency low-toxicity broad-spectrum herbicide for preventing and killing broadleaf weeds by post-emergence stem and leaf treatment, and can effectively prevent and kill most broadleaf weeds such as cleavers, mai-home cocktails and the like in wheat fields and lawns.
8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione is used as an important intermediate for synthesizing florasulam, the synthesis reaction is an oxidation reaction which is one of 18 critical processes which are monitored in an important mode, and the conventional synthesis of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione generally adopts a kettle type reaction, so that the method is high in risk, low in equipment utilization rate, incomplete in reaction, poor in product stability, low in yield and not suitable for industrial production.
Disclosure of Invention
Aiming at the problems in the related art, the invention provides a synthetic method of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione.
The reaction equation is as follows:
in order to achieve the purpose, the invention provides the following technical scheme:
the invention provides a method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone, which comprises the following steps:
(1) dissolving 5-fluoro-4-hydrazino-2-methoxypyrimidine in a solvent for later use;
(2) putting hydrogen peroxide into a storage tank for later use;
(3) placing the carbon disulfide in a storage tank for later use;
(4) at a certain temperature, respectively pumping 5-fluoro-4-hydrazino-2-methoxypyrimidine solution and carbon disulfide into a microchannel reactor I by using a diaphragm metering pump, and finishing the reaction;
(5) then pumping hydrogen peroxide into a micro-channel reactor II by using a diaphragm metering pump, and finishing the oxidation reaction;
(6) the reaction liquid is centrifuged by a centrifuge to obtain 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone solution.
Preferably, the solvent is methanol or chloroform.
Preferably, the concentration of the 5-fluoro-4-hydrazino-2-methoxypyrimidine is 30-40%, and the dissolving temperature of the 5-fluoro-4-hydrazino-2-methoxypyrimidine solution is 30-40 ℃.
Preferably, the concentration of the hydrogen peroxide is 30% and 35%.
Preferably, the error of the diaphragm metering pump is less than 0.05%.
Preferably, the molar ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the carbon disulfide is 1: 1.10-1.30.
Preferably, the molar ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the hydrogen peroxide is 1: 1.05-1.20.
Preferably, the reaction temperature in the microchannel reactor I is 50-70 ℃; the residence time in the microchannel reactor I is 5-8 min.
Preferably, the reaction temperature in the microchannel reactor II is 30-50 ℃; and the residence time in the microchannel reactor II is 3-5 min.
Preferably, the rotating speed of the centrifugal machine is 2000-2500 r/min; the solid centrifuged by the centrifuge is sulfur.
Compared with the prior art, the invention has the beneficial effects that:
the method has the advantages of simple operation steps, low danger, high equipment utilization rate, complete reaction, high product stability and high yield, thereby being suitable for industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The synthesis of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to this example had the following steps:
(1) transferring 1400Kg of dry methanol into a 3000L reaction kettle through a flowmeter, opening a manhole, adding 600Kg of 5-fluoro-4-hydrazino-2-methoxypyrimidine, heating to 30 ℃, stirring for 1h, fully dissolving for later use, and detecting the content of the 5-fluoro-4-hydrazino-2-methoxypyrimidine;
(2) setting the reaction temperature of a microchannel reactor I to be 50 ℃, respectively conveying 5-fluoro-4-hydrazino-2-methoxypyrimidine and carbon disulfide to two channels of the microchannel reactor I by using a diaphragm metering pump, adjusting the flow rate of the diaphragm metering pump, ensuring that the mol ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the carbon disulfide is 1:1.1, keeping the retention time of materials in the microchannel reactor I for 5min, and after the reaction is finished, feeding feed liquid into an intermediate storage tank for later use;
(3) setting the reaction temperature of the microchannel reactor II to be 30 ℃, respectively conveying the feed liquid and 30% of hydrogen peroxide which are subjected to upper reaction to two channels of the microchannel reactor II by using a diaphragm metering pump, adjusting the flow rate of the diaphragm metering pump, ensuring that the mol ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the hydrogen peroxide is 1:1.08, ensuring that the residence time of the materials in the microchannel reactor II is 3min, and after the reaction is finished, feeding the feed liquid into a finished product storage tank;
(4) and (3) conveying the feed liquid in the finished product tank to a centrifugal machine by using a gear pump, adjusting the rotating speed of the centrifugal machine to 2000r/min, and obtaining a methanol solution of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone after the centrifugation is finished, wherein the liquid phase normalization is 97.3%, and the yield is 92.5%.
EXAMPLES example 2
The synthesis of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to this example had the following steps:
(1) transferring 1400Kg of dry chloroform into a 3000L reaction kettle through a flowmeter, opening a manhole, adding 600Kg of 5-fluoro-4-hydrazino-2-methoxypyrimidine, heating to 30 ℃, stirring for 1h, fully dissolving for later use, and detecting the content of the 5-fluoro-4-hydrazino-2-methoxypyrimidine;
(2) setting the reaction temperature of a microchannel reactor I to be 60 ℃, respectively conveying 5-fluoro-4-hydrazino-2-methoxypyrimidine and carbon disulfide to two channels of the microchannel reactor I by using a diaphragm metering pump, adjusting the flow rate of the diaphragm metering pump, ensuring that the mol ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the carbon disulfide is 1:1.2, keeping the retention time of materials in the microchannel reactor I for 6min, and after the reaction is finished, feeding a feed liquid into an intermediate storage tank for later use;
(3) setting the reaction temperature of the microchannel reactor II to 50 ℃, respectively conveying the feed liquid and 30% of hydrogen peroxide which are subjected to upper reaction to two channels of the microchannel reactor II by using a diaphragm metering pump, adjusting the flow rate of the diaphragm metering pump, ensuring that the mol ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the hydrogen peroxide is 1:1.05, the retention time of the materials in the microchannel reactor II is 3min, and after the reaction is finished, feeding the feed liquid into a finished product storage tank;
(4) and (3) conveying the feed liquid in the finished product tank to a centrifuge by using a gear pump, adjusting the rotating speed of the centrifuge to 2000r/min, and obtaining a chloroform solution of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone after the centrifugation is finished, wherein the liquid phase normalization is 97.8%, and the yield is 93.3%.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (10)
1. A method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione, comprising the steps of:
(1) dissolving 5-fluoro-4-hydrazino-2-methoxypyrimidine in a solvent for later use;
(2) putting hydrogen peroxide into a storage tank for later use;
(3) placing the carbon disulfide in a storage tank for later use;
(4) at a certain temperature, respectively pumping 5-fluoro-4-hydrazino-2-methoxypyrimidine solution and carbon disulfide into a microchannel reactor I by using a diaphragm metering pump, and finishing the reaction;
(5) then pumping hydrogen peroxide into a micro-channel reactor II by using a diaphragm metering pump, and finishing the oxidation reaction;
(6) the reaction liquid is centrifuged by a centrifuge to obtain 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thioketone solution.
2. The method of claim 1, wherein in step one, the solvent is selected from the group consisting of chlorobenzene, toluene, dichloromethane, dichloroethane, benzene, xylene, chloroform, methanol, ethanol, and isopropanol.
3. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the concentration of 5-fluoro-4-hydrazino-2-methoxypyrimidine in the 5-fluoro-4-hydrazino-2-methoxypyrimidine solution is 20-60%; the dissolving temperature of the 5-fluoro-4-hydrazino-2-methoxypyrimidine solution is 20-40 ℃.
4. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the concentration of hydrogen peroxide is 27.5-70%.
5. The method of synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione of claim 1, wherein the tolerance of said diaphragm metering pump is less than 0.05%.
6. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the molar ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to the carbon disulfide is 1: 1.05-1.60.
7. The synthesis method of 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the molar ratio of the 5-fluoro-4-hydrazino-2-methoxypyrimidine to hydrogen peroxide is 1: 1.02-1.30.
8. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the reaction temperature in the microchannel reactor I is 10-80 ℃; the residence time in the microchannel reactor I is 5-20 min.
9. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the reaction temperature in the microchannel reactor II is 5-60 ℃; and the residence time in the microchannel reactor II is 2-10 min.
10. The method for synthesizing 8-fluoro-5-methoxy-2H- [1,2,4] triazolo [4,3-c ] pyrimidine-3-thione according to claim 1, wherein the rotation speed of the centrifuge is 1200-2500 r/min; the solid centrifuged by the centrifuge is sulfur.
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| CN202210127039.4A CN114437083A (en) | 2022-02-11 | 2022-02-11 | Synthetic method of thioketone |
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| CN202210127039.4A CN114437083A (en) | 2022-02-11 | 2022-02-11 | Synthetic method of thioketone |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995012597A1 (en) * | 1993-11-05 | 1995-05-11 | Dowelanco | 2-alkoxy-4-hydrazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2-4-triazolo[4,3-c]pyrimidine-3(2h)-thione compounds |
| US5480991A (en) * | 1993-11-05 | 1996-01-02 | Dowelanco | 2-Alkoxy-4-hydroazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds |
| CN1205336A (en) * | 1993-11-05 | 1999-01-20 | 道农业科学公司 | 5-Alkoxy [1,2,4] triazolo [1,5,-C] pyrimidine -2[3H]-thione compounds and their use |
| CN103923086A (en) * | 2014-03-31 | 2014-07-16 | 齐鲁工业大学 | Preparation method of 5-alkoxy-1,2,4-triazole[4,5-c]pyrimidine-3(2H)-thioketone |
-
2022
- 2022-02-11 CN CN202210127039.4A patent/CN114437083A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995012597A1 (en) * | 1993-11-05 | 1995-05-11 | Dowelanco | 2-alkoxy-4-hydrazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2-4-triazolo[4,3-c]pyrimidine-3(2h)-thione compounds |
| US5480991A (en) * | 1993-11-05 | 1996-01-02 | Dowelanco | 2-Alkoxy-4-hydroazinopyrimidine compounds and their use in the preparation of 5-alkoxy-1,2,4-triazolo[4,3-c]pyrimidine-3(2H)-thione compounds |
| CN1205336A (en) * | 1993-11-05 | 1999-01-20 | 道农业科学公司 | 5-Alkoxy [1,2,4] triazolo [1,5,-C] pyrimidine -2[3H]-thione compounds and their use |
| CN103923086A (en) * | 2014-03-31 | 2014-07-16 | 齐鲁工业大学 | Preparation method of 5-alkoxy-1,2,4-triazole[4,5-c]pyrimidine-3(2H)-thioketone |
Non-Patent Citations (3)
| Title |
|---|
| 刘敬等: "8-氟-5-甲氧基-1,2,4-三唑并[4,3-c]嘧啶-3(2H)-硫酮的合成", 《广东化工》 * |
| 张梅凤等: "除草剂双氟磺草胺的合成", 《农药》 * |
| 王胜得等: "除草剂双氟磺草胺的合成研究", 《农药科学与管理》 * |
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Application publication date: 20220506 |