Clomazone CAS 81777-89-1
Introduction：Basic information about Clomazone CAS 81777-89-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Clomazone Basic information
| Product Name: | Clomazone |
| Synonyms: | 2-((2-chlorophenyl)methyl)-4,4-dimethyl-3-isoxazolidinon;2-(2-Chlorobenzyl)-4,4-dimethyl-3-isoxazolidinone;dimethazone;3-Isoxazolidinone, 2-(2-chlorophenyl)methyl-4,4-dimethyl-;clomazone (bsi,ansi,draft e-iso,draft f-iso);Clomazon;Comazone;Dimethazon |
| CAS: | 81777-89-1 |
| MF: | C12H14ClNO2 |
| MW: | 239.7 |
| EINECS: | |
| Product Categories: | Alphabetic;CO - CZ;Agricultural Usage;CI - CLPesticides&Metabolites;Alpha sort;C;CAlphabetic;Herbicides;Others;Pesticides&Metabolites;HERBICIDE;81777-89-1 |
| Mol File: | 81777-89-1.mol |
Clomazone Chemical Properties
| Melting point | 25°C |
| Boiling point | 275.4°C |
| density | 1.192 |
| refractive index | 1.5388 (estimate) |
| Fp | 157 °C |
| storage temp. | Sealed in dry,2-8°C |
| solubility | DMF: 33 mg/ml,DMSO: 16 mg/ml,Ethanol: 33 mg/ml,PBS (pH 7.2): 1 mg/ml |
| form | Solid |
| pka | -1.48±0.40(Predicted) |
| color | White to off-white |
| Water Solubility | 1.101g/L(temperature not stated) |
| BRN | 7480026 |
| Major Application | agriculture environmental |
| InChI | 1S/C12H14ClNO2/c1-12(2)8-16-14(11(12)15)7-9-5-3-4-6-10(9)13/h3-6H,7-8H2,1-2H3 |
| InChIKey | KIEDNEWSYUYDSN-UHFFFAOYSA-N |
| SMILES | CC1(C)CON(Cc2ccccc2Cl)C1=O |
| CAS DataBase Reference | 81777-89-1(CAS DataBase Reference) |
| NIST Chemistry Reference | Dimethazone(81777-89-1) |
| EPA Substance Registry System | Clomazone (81777-89-1) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/22-36/38 |
| Safety Statements | 26-36 |
| RIDADR | 2902 |
| WGK Germany | 2 |
| RTECS | NY2977000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 81777-89-1(Hazardous Substances Data) |
| Toxicity | LD50 in male rats, female rats, mallard duck-bobwhite quail (mg/kg): 2077, 1369, >2510 orally; in rabbits (mg/kg): >2000 dermally (Chen) |
| Description | The molecular target site of clomazone has recentlybeen determined. With clomazone, carotenoid synthesisis inhibited, but no intermediates in the carotenoidcommittedportion of the pathway accumulate (5,6).Synthesis of the derivatives of GGPP (gibberellic acid,phytol, carotenoids) is inhibited by clomazone (5–8).However, the synthesis of certain sesquiterpenoids andtriterpenoids is not inhibited (9). Until recently, there wasno credible report of the effect of clomazone on any enzymeof the terpenoid pathway (10–12). This was due to thefact that clomazone is a proherbicide and that the properenzyme had not been tested. |
| Chemical Properties | Depending purity, it may be clear and colorless to pale yellow or brownish liquid. Commercially available as emulsifiable concentrates that can be dissolved in water |
| Uses | Herbicide. |
| Definition | ChEBI: A oxazolidinone that is 1,2-oxazolidin-3-one substituted by a 2-chlorobenzyl group at position 2 and two methyl groups at position 4. |
| Hazard | Moderately toxic by ingestion, inhalation,and skin contact. A reproductive hazard. |
| Agricultural Uses | Herbicide: Clomazone is a broad-spectrum herbicide used onrice, peas, pumpkins, soybeans, sweet potatoes, wintersquash, cotton, tobacco and fallow wheat fields to controlannual grasses and broadleaf weeds. |
| Trade name | CERANO®; COLZOR TRIO®;COMMAND®; COMMENCE®, DIBEL®; FMC® 57020;GAMBIT®; MAGISTER®; MERIT®; STRATEGY® |
| Synthesis | 611-19-8 81778-07-6 81777-89-1 1. 1000 kg of water was added to a 4000 L reactor followed by 460 kg of 4,4-dimethylisoxazolidin-3-one. The mixture was stirred for 1 hour at room temperature.2. 383kg of sodium carbonate (Na2CO3) was added to the reaction mixture in small portions. The temperature of the mixture was raised to 85°C and the mixture was stirred continuously at this temperature for 2 hours.3. 672 kg of o-chlorobenzyl chloride (2-chlorobenzyl chloride) was added slowly and dropwise over a period of 5 hours at 85°C. The mixture was kept at the same temperature for 2 hours. After the dropwise addition was completed, the temperature was maintained at 85°C until the reaction was complete.4. The reaction mixture was cooled to room temperature, 800 kg of dichloromethane was added and stirred at room temperature for 15 hours.5. The aqueous phase was separated and the aqueous phase was extracted three times with dichloromethane.6. Recover the dichloromethane by distillation followed by addition of 2000 kg of hexane to the reactor. The mixture was refluxed for 1 hour, then cooled to 10-15 °C and continued stirring for 1 hour.7. The solid product was separated by filtration, washed several times with hexane and finally dried under high vacuum to give pure 2-(2-chlorobenzyl)-4,4-dimethyloxazolidin-3-one (815 kg, purity: 96%).Note: Similar results were obtained using sodium hydroxide instead of sodium carbonate as base. |
| Potential Exposure | Clomazone is a oxazolidione broadspectrum herbicide used on rice, peas, pumpkins, soybeans, sweet potatoes, winter squash, cotton, tobacco, and fallow wheat fields to control annual grasses and broadleaf weeds. |
| Metabolic pathway | By the preparative incubation of clomazone withmicroorganisms that have the ability to metabolizeclomazone, the metabolites are identified via majorbiotransformation reactions which involvehydroxylation at the 5-methylene carbon and one ofthe 3-methyl groups of the isoxazolidone ring and atthe 3 0 -position of the phenyl ring. Minor metabolicroutes include dihydroxylation on the phenyl ring,cleavage of the isoxazolinone ring, or completeremoval of the isoxazolinone ring to form2-chlorobenzyl alcohol. Under aerobic conditions ofsoils, degradation of clomazone proceeds primarily byCO2 evolution and the formation of bound soilresidues. In flooded soils, clomazone is found rapidlyto degrade via the formation of the reductive product N-[(2-chlorophenyl)methyl]-3-hydroxy-2,2-dimethylpropionamide. In tolerant soybean cellsuspension cultures, the only metabolite identified isb-glycosyl-2-chlorobenzyl alcohol. |
| Shipping | UN2902 Pesticide, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. |
| Incompatibilities | Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. |
| Waste Disposal | Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. |
| References | [1] Patent: WO2015/353, 2015, A1. Location in patent: Page/Page column 16; 17 [2] Patent: CN106749072, 2017, A. Location in patent: Paragraph 0018; 0021; 0024; 0027 |
Clomazone Preparation Products And Raw materials
| Raw materials | Dichloromethane-->Thionyl chloride-->Hydroxylamine hydrochloride-->Pivaloyl chloride-->DOYLE DIRHODIUM CATALYST-RH2(4S-MEOX)4-->Extractant-->Pivalic acid-->2-Chlorobenzyl chloride-->Isoxazole-->3,3-Dimethyl-1-(1,2,4-triazole-1-yl)-2-butanone-->3-Chloropivaloyl chloride-->Pivaldehyde-->Propanamide, 3-chloro-N-[(2-chlorophenyl)methyl]-N-hydroxy-2,2-dimethyl--->4，4-dimethyl isoxazolidin-3-one-->3-CHLORO-N-HYDROXY-2,2-DIMETHYL-PROPANAMIDE |
