145701-23-1
Florasulam
CAS: 145701-23-1
Molecular Formula: C12H8F3N5O3S
145701-23-1 - Names and Identifiers
| Name | Florasulam |
| Synonyms | de-570 Florasulam FLORASULAM Florasulam [iso] florasulam (bsi,iso) N-(2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide N-(2,6-Difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide florasulam (ISO) 2',6',8-trifluoro-5-methoxy-5-triazolo[1,5-c] pyrimidine-2-sulfonanilide [1,2,4]Triazolo[1,5-c]pyrimidine-2-sulfonamide, N-(2,6-difluorophenyl)-8-fluoro-5-methoxy- |
| CAS | 145701-23-1 |
| InChI | InChI=1/C12H8F3N5O3S/c1-23-12-16-5-8(15)10-17-11(18-20(10)12)24(21,22)19-9-6(13)3-2-4-7(9)14/h2-5,19H,1H3 |
| InChIKey | QZXATCCPQKOEIH-UHFFFAOYSA-N |
145701-23-1 - Physico-chemical Properties
| Molecular Formula | C12H8F3N5O3S |
| Molar Mass | 359.28 |
| Density | 1.75±0.1 g/cm3(Predicted) |
| Melting Point | 220-221° (dec) (Van Heertum); also reported as 193.5-230.5° (Thompson) |
| Appearance | neat |
| pKa | 4.54(at 25℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.676 |
| Physical and Chemical Properties | Storage Conditions: 0-6 ℃ |
145701-23-1 - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 2 |
| Toxicity | LD50 in rat, quail (mg/kg): >6000, 1046 orally; percutaneously in rabbit: >2000 mg/kg; LC50 in rainbow trout, bluegill (96 hr): >96, >98 mg/l (Thompson) |
145701-23-1 - Reference Information
Open Data Unverified Data
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) | |
| Sulfonamide herbicides | Difluorosulfamide is a sulfonamide herbicide, similar to sulfonylurea herbicides, sulfonamide herbicides are also typical Acetolactate synthase inhibitor. Targeting ALS, they are mixed inhibitors involving pyruvate and thiamine pyrophosphate (TPP), competing for the binding site of the enzyme, but not for the matrix or cofactors. Sulfonamide herbicides are a new class of acetolactate synthase inhibitors developed by Dow Yinong Company in the United States. Its main structural form is triazolopyrimidinesulfonamide. There are currently 6 varieties, all of which are dry field herbicides, including oxifolamine, methoxysulfuramine, chlorosolamine, dichlorosulfuramine, and difluorosolamine and penoxolamine. Zazimuron is safe for soybean, corn, wheat, barley, pea, alfalfa, clover, etc., and has no adverse effect on subsequent crops. Methodoxamine is used to control most of the main broad-leaved weeds in wheat, barley, and rye fields after seedlings. It can be used before and after seedlings to control most of the main broad-leaved weeds in corn fields. Chloroester sulfonamide is mainly used to prevent and remove broadleaf weeds before and after seedling in soybean fields, and has special effects on Xanthium sibiricum, ragweed, trifid leaf ragweed, sweet potato and Abutilon. Dichlorosulfamethoxamine is a soybean field herbicide. Bifolamide is mainly used to control broad-leaved weeds in winter wheat fields after seedlings. Pentafosulforamine is a recently reported herbicide, which is mainly used to control weeds in rice fields. at present, sulfamide herbicide preparations 5.8% difluorosulfamethoxamine suspending agent and 80% sulfamethoxamine water dispersible granules have been approved for registration in China. Diflon sulfamethoxamine is the fifth triazolidine sulfonamide herbicide successfully developed in the mid-2090s after sulfamethoxamine, sulfuroxamine, chloroester sulfamethoxamine and dichlorosulfamethoxamine. New varieties. Figure 1 is the structural formula of difluorosamine. | |
| the original drug and preparation | the original drug and preparation | the drug was developed by Dow Yinong company and registered in Israel in 1998. In 1998, Dow Yinong submitted an application for registration of difluorosamine to the European Union, which was listed in Appendix 1 of the EU Pesticide Registration Directive (91/414) on October 1, 2002. In 1999, diflumesulam was listed in Belgium and the United Kingdom. From 2000 to 2002, diflumosamine was listed in France, the Netherlands and Spain. By 2002, the annual sales of bisfoxalamine were about US $0.14 billion. In 2008, the U.S. Environmental Protection Agency plans to register difluorosamine. The residual activity period of bisfluorosulforamine is short, so it is generally used in combination with other herbicide active ingredients. In 2001, the compound product of bisfoxalamine and 2,4-D was Mustang on the market in Croatia. In 2002, the double-packaged products of bisfluorosulforamine and glyphosate were launched in France. In 2003, double-packaged compound products such as difluorosulfamethoxamine + glyphosate, difluorosulfamethoxamine + MCPA, and difluorosulfamethoxamine + dichloropyridyl acid + 2methyl 4 chlorine were introduced into the Canadian market. On January 9, 2011, Dow Yinong obtained the Chinese registration of the original drug and suspending agent of the 97% of bisfluorosulfamate, and also obtained the Chinese registration of the compound suspension emulsion of bisfluorosulfamate and 2, 4-isooctyl ester. after experiencing a decline in sales in 2008, due to the growth of demand in the European grain market, the difluorosulfuramine market recovered to a certain extent in 2011 and brought sales revenue of us $0.195 billion to Dow beneficial farmers in that year. At present, there are 4 domestic enterprises with the original drug registration certificate of bifurcamide, namely: Jiangsu Agricultural Hormone Engineering Technology Research Center Co., Ltd., Shandong United Pesticide Industry Co., Ltd., Yongnong Biological Science Co., Ltd. and Shandong Weifang Runfeng Chemical Co., Ltd. The difluorosulfamethoxamine preparations registered in China are mainly suspending agents. At present, the domestic enterprises registered in China are: 50g/L suspending agent of bisfluorosulfamide from Jiangsu Agricultural Hormone Engineering Technology Research Center Co., Ltd. In addition, the difluoro-octyl 459g/l suspending agent of zhongnongzhushang (Tianjin) agrochemicals co., ltd. and the difluoro-tazolamide 175g/l suspending agent of Jiangsu Suzhou jiahui chemical co., ltd. also obtained the sub-packaging registration certificate. on August 15, 2015, the European Commission issued regulation (EU)2015/1397 to update the approved active substance difluorosulfamethoxamine (Florasulam). This Regulation shall come into force on the 20th of its promulgation and shall come into force on the 1st of January 2016. According to Article 20(3) and 13(4) of Regulation (EC)No 1107/2009, Annex to EU Regulation (EU)No 540/2011 shall be revised accordingly. Regulation (EU)No 540/2011 Annex Part A Entry 36 Bifolamide is deleted, Part B adds the corresponding entry, and the number of Bifolamide is 90. On August 25, 2015, Dow Yinong herbicide difluorosulfamethoxamine was renewed for registration in the European Union. The original registration of this product will expire on December 31, 2015, and the renewal registration will take effect from January 1, 2016. The European Commission pointed out that member states should pay special attention to the risks of products to aquatic organisms and non-target terrestrial plants. Conditions of use should include appropriate risk mitigation measures. |
| toxicity | acute oral LD50>6000 mg/kg in rats and acute percutaneous LD50>2000 mg/kg in rabbits. It is irritating to rabbit eyes and non-irritating to rabbit skin. No teratogenic, carcinogenic, mutagenic effects, no adverse genetic effects. NOEL data: large and mouse (90d)100mg/kg d. No teratogenic, carcinogenic, mutagenic effects, and no adverse effects on genetics. Quail acute oral LD50>6000mg/kg. Quail and wild ducks were fed with LD50(5d)>5000mg/kg feed. Fish poison LC50(96h,mg/L): rainbow trout> 86, big sunfish> 98. LD50(48h)>100 μg/bee (via mouth and contact). Earthworm LD50(14d)>1320mg/kg soil. | |
| Degradation | Bfo-sulforamine disappears mainly through microbial degradation in soil, which is safe for most subsequent crops. the degradation rate of bisflurane in soil is determined by soil temperature and humidity, with a half-life of 1.0-8.5 days at 20-25 ℃ and 6.4-85 days at 5 ℃. The main degradation product is 5-hydroxydifluorosulfamethoxamine, and the secondary degradation products are: N-(2, 6-difluorophenyl) -5-aminosulfonyl-1H-1, 2, 4-triazol-3-carboxylic acid, 5-aminosulfonyl-1H-1, 2, 4-triazol-3-carboxylic acid and 1H-1,2, 4-triazol-3-sulfonamide, all primary and secondary degradation products are harmless to plants. Photodegradation is also a factor for the disappearance of BFFA, especially on the soil surface with low microbial activity, photoenzyme reduction may be important; in the summer of 40 ° north latitude, BFFA is photolysis on the soil surface The half-life is l4 days, and the semi-wrapping period of photolysis in sterilization buffer water is 36 days; the photolysis is rapid in natural water, and the half-life is 3.3 days in summer at 51.5 ° north latitude. Therefore, the photodegradation process is important to promote the disappearance of bisfluorosulfuran in the environment, especially in the water environment. | |
| application | difluorosamine is mainly used to prevent broad-leaved weeds in winter wheat fields such as pig calamity, trichophyllum, polygonum weeds, Compositae weeds, etc. after seedlings. the usage is only 3-10g of active ingredients/ha [the usage per mu is 0.2-0.67g(a. I)], and difluorosamine is used as an inhibitor of acetolactate synthase (ALS), it is highly selective for wheat crops and lawns, and can be widely used in winter wheat, winter wheat, spring wheat, spring barley, lawns, onions and grasslands, pastures, etc. The highest dosage of the drug per hectare is 7.5g in Europe and 5g in Canada. 154 field experiments completed in Britain, France and Greece in 1994 and 1997 proved that the application of the highest dose of double treatment is also very safe for crops. The safety of difluorosulfuran against winter wheat is higher than that of sulfonylurea herbicide metsulfuron. The dosage of 5-15g per hectare is very selective for lawn and pasture ryegrass, multiflorum ryegrass, fescue, purple fescue, reed fescue bluegrass, timothy and bentgrass. Bifofosulforamine is a broad-spectrum weeding agent for the treatment of stems and leaves after seedlings to control broad-leaved weeds. The dosage of 5g per hectare can effectively control Dianthus, madder, Malvaceae, and Polygonaceae. Weeds, important weeds in the field such as Stellaria, Pig, Solanum nigrum, Polygonum curl, etc. are very sensitive to them. At a dose of 5g/hm2, it can prevent pigs with a plant height of 20cm, 2.5g can prevent 6 strands in the true leaf stage, and 5g can completely prevent strands and mother chrysanthemum in the late growth stage. bisfluorosulforamine has strong miscibility and is suitable for mixing with plant growth regulators, other herbicides, fungicides, etc. liquid nitrogen can be added to wheat fields, and the dosage per hectare can be reduced to 2.5g. Herbicides that can be mixed with it include zolimuronazide, 2methyl 4 chloride, oxazolaopyrin, fluorocene, ethofotaxane, dichlorepidinic acid, methyl carboxylic dewormether, etc. The application method of bisflurane is flexible. It can be mixed with soil before sowing and soil treatment before seedling, or sprayed after seedling. | |
| Synthesis method | Using 2,4-dichloro-5-fluoropyrimidine as the starting material, through etherification reaction, hydrazinization reaction, cyclization reaction, benzyl thioetherification reaction, isomerization reaction, chlorine oxidation reaction and amidation reaction, seven-step reaction to synthesize difluorosulfuramide. | |
| patent status | 1. European patent: Tao agricultural science company-EP 0343752, the patent application date: may 24, 1989, and the patent termination date: may 23, 2009. On October 1, 2002, difofosulfamide was included in Appendix 1 of the EU Pesticide Registration Directive (91/414), and its registration data obtained the right of protection for 10 years starting from this day. Therefore, the protection period of its registration data is until September 30, 2012. 2. UK Supplementary Protection Certificate (SPCs):SPC/GB00/009EP0343752-Bifolosulfamide is valid until December 3, 2013. 3. U.S. patent: Tao Agricultural Science Corporation-US 5010195, which expired on May 24, 2008. 4. Chinese patent: "preparation method of alkoxy -1,2, 4-triazolo [1,5-C] pyrimidine-2-sulfamate" patent number: CN1030606C; Application number: 89103624.5; Application date: 1989.05.24; Patent publication date: 1990.02.14. "Herbicidal methods and compositions using alkoxy -1,2,4-triazolo [1,5-c] pyrimidine -2-sulfamate" patent number: CN1106010A; Application number: 93116973.9; Application date: 1989.05.24; Patent publication date: 1995.08.02, both of which expired on May 23, 2009. | |
| use | winter wheat herbicide. | |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:43:38
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