81777-89-1 Usage
Description
The 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 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 on
rice, peas, pumpkins, soybeans, sweet potatoes, winter
squash, cotton, tobacco and fallow wheat fields to control
annual grasses and broadleaf weeds.
Trade name
CERANO?; COLZOR TRIO?;
COMMAND?; COMMENCE?, DIBEL?; FMC? 57020;
GAMBIT?; MAGISTER?; MERIT?; STRATEGY?
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 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 81777-89-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,7,7 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 81777-89:
(7*8)+(6*1)+(5*7)+(4*7)+(3*7)+(2*8)+(1*9)=171
171 % 10 = 1
So 81777-89-1 is a valid CAS Registry Number.
InChI:InChI=1/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
81777-89-1Relevant articles and documents
Preparation method of high-content clomazone
-
Paragraph 0005; 0021-0032, (2021/07/21)
The invention discloses a preparation method of high-content clomazone, which comprises the following steps: putting an aqueous solution of 4,4-dimethyl-3-isoxazolone sodium salt, sodium carbonate and sodium iodide into a reaction kettle, pumping o-chlorochlorobenzene, and stirring and heating the reactants; keeping the temperature and reacting for 1.5-3 hours; performing sampling and central control, and then washing, layering and desolventizing the reaction product to obtain a crude clomazone product. A small amount of sodium chloride is added in the synthesis process of the clomazone, so that the reaction speed is greatly increased, the reaction time is shortened from 10 hours to 2 hours, the main content can reach 85% or above, and by-products are reduced to 3% or below.
Preparation method of clomazone
-
Paragraph 0003-0004, (2021/06/26)
The invention relates to a preparation method of clomazone. The method comprises: by taking hydroxylamine hydrochloride as a raw material, dropwise adding chloro pivaloyl chloride under the action of a self-made ether catalyst to obtain an intermediate 3-chloro-N-hydroxyl-2, 2-dimethyl propionamide with high yield, then cyclizing to prepare 4, 4-dimethyl-3-isoxazolone, and carrying out benzylation under pioneered caustic soda flake catalysis without separation to directly prepare 2-(2-chlorphenyl) methyl-4, 4-dimethyl-3-isoxazolone. Compared with existing literature methods, the method of the invention has the advantages that the self-made ether catalyst is innovatively used, so that the yield in the first step is remarkably improved, and the content and optical purity of the product are high; in the final benzylation reaction, caustic soda flakes are used to improve the yield, and water is used as a solvent in the whole reaction process, so that the cost is low, the recovery and post-treatment are simple, the reaction is mild, and the intermediate control is simple; and the preparation method provided by the invention has the advantages of easily available reaction raw materials, mild reaction, high yield, simple separation and purification, low cost and environment-friendly preparation process.
Low-temperature synthesis process of clomazone
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Paragraph 0025-0027; 0031-0031; 0037-0039, (2019/09/05)
The invention discloses a low-temperature synthesis process of clomazone. The low-temperature synthesis process of the clomazone comprises condensation reaction, cyclization reaction, synthesis reaction and configuration conversion. The low-temperature synthesis process of the clomazone disclosed in the invention starts from analyzing side reaction products, determines the chemical composition ofimpurities, and reduces the amount of the impurities by optimizing process parameters, finding high-efficiency catalysts and controlling side reactions; then, through chemical treatment on the produced isomers, part of the isomers are converted into the product, and part of irreversible by-products are converted into high-boiling-point polymer compounds through reaction, so that the clomazone product is easy to separate; finally, the clomazone product is purified through physical methods to obtain the clomazone with a purity greater than 97%.
