Clomazone

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;CI - CLPesticides&Metabolites;Alpha sort;C;Agricultural Usage;HERBICIDE;CAlphabetic;Herbicides;Others;Pesticides&Metabolites;81777-89-1
Mol File:81777-89-1.mol
Clomazone Structure
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 neat
pka-1.48±0.40(Predicted)
Water Solubility 1.101g/L(temperature not stated)
BRN 7480026
InChIKeyKIEDNEWSYUYDSN-UHFFFAOYSA-N
CAS DataBase Reference81777-89-1(CAS DataBase Reference)
NIST Chemistry ReferenceDimethazone(81777-89-1)
EPA Substance Registry SystemClomazone (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
Hazardous Substances Data81777-89-1(Hazardous Substances Data)
ToxicityLD50 in male rats, female rats, mallard duck-bobwhite quail (mg/kg): 2077, 1369, >2510 orally; in rabbits (mg/kg): >2000 dermally (Chen)
MSDS Information
Clomazone Usage And Synthesis
DescriptionThe molecular target site of clomazone has recently been determined. With clomazone, carotenoid synthesis is inhibited, but no intermediates in the carotenoidcommitted portion 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 and triterpenoids is not inhibited (9). Until recently, there was no credible report of the effect of clomazone on any enzyme of the terpenoid pathway (10–12). This was due to the fact that clomazone is a proherbicide and that the proper enzyme had not been tested.
Chemical PropertiesDepending purity, it may be clear and colorless to pale yellow or brownish liquid. Commercially available as emulsifiable concentrates that can be dissolved in water
UsesHerbicide.
DefinitionChEBI: 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.
HazardModerately toxic by ingestion, inhalation, and skin contact. A reproductive hazard.
Agricultural UsesHerbicide: Clomazone is a broad-spectrum herbicide used on rice, peas, pumpkins, soybeans, sweet potatoes, winter squash, cotton, tobacco and fallow wheat fields to control annual grasses and broadleaf weeds.
Trade nameCERANO®; COLZOR TRIO®; COMMAND®; COMMENCE®, DIBEL®; FMC® 57020; GAMBIT®; MAGISTER®; MERIT®; STRATEGY®
Potential ExposureClomazone 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 pathwayBy the preparative incubation of clomazone with microorganisms that have the ability to metabolize clomazone, the metabolites are identified via major biotransformation reactions which involve hydroxylation at the 5-methylene carbon and one of the 3-methyl groups of the isoxazolidone ring and at the 3 0 -position of the phenyl ring. Minor metabolic routes include dihydroxylation on the phenyl ring, cleavage of the isoxazolinone ring, or complete removal of the isoxazolinone ring to form 2-chlorobenzyl alcohol. Under aerobic conditions of soils, degradation of clomazone proceeds primarily by CO2 evolution and the formation of bound soil residues. In flooded soils, clomazone is found rapidly to degrade via the formation of the reductive product N-[(2-chlorophenyl)methyl]-3-hydroxy-2,2- dimethylpropionamide. In tolerant soybean cell suspension cultures, the only metabolite identified is b-glycosyl-2-chlorobenzyl alcohol.
ShippingUN2902 Pesticide, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
IncompatibilitiesIncompatible 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 DisposalDo 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.
ISOXAFLUTOLE Dimethylbenzylcarbinyl acetate Methyl Benzyl chloride Benzylchloromethyl ether OXYPHENYL BUTAZONE Clomazone Phenylacetone Trazodone tert-Butyldimethylsilyl chloride ETHANE Oxadiazon Benzyldimethylcarbinyl butyrate Dimethyl sulfide Sulcotrione Dimethyl fumarate Dimethyl ether Dimethyl phthalate

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