Clomazone

Base Information

• Chemical Name: Clomazone
• CAS No.: 81777-89-1
• Deprecated CAS: 89493-06-1
• Molecular Formula: C12H14ClNO2
• Molecular Weight: 239.702
• Hs Code.: 2934999027
• European Community (EC) Number: 617-258-0
• UNII: 570RAC03NF
• DSSTox Substance ID: DTXSID1032355
• Nikkaji Number: J134.068I
• Wikipedia: Clomazone
• Wikidata: Q2187383
• Metabolomics Workbench ID: 67771
• ChEMBL ID: CHEMBL1076356
• Mol file: 81777-89-1.mol

Synonyms:2-(2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone;clomazone;Command herbicide;dimethazone

Chemical Property of Clomazone

Chemical Property:

• Vapor Pressure: 0.00038mmHg at 25°C
• Melting Point: 25 °C
• Refractive Index: 1.55
• Boiling Point: 317.6 °C at 760 mmHg
• PKA: -1.48±0.40(Predicted)
• Flash Point: 145.9 °C
• PSA: 29.54000
• Density: 1.223 g/cm³
• LogP: 2.57790
• Storage Temp.: 0-6°C
• Water Solubility.: 在水中的溶解度1.1g/L，易容于丙酮，乙腈、氯仿、环已酮、二氯甲烷、甲醇、甲笨等有机溶剂
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 239.0713064
• Heavy Atom Count: 16
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

Clomazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Herbicides, Other
• Canonical SMILES: CC1(CON(C1=O)CC2=CC=CC=C2Cl)C
• 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.
• Uses: Herbicide.

Technology Process of Clomazone

There total 9 articles about Clomazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

1-chloro-2-(chloromethyl)benzene (611-19-8) + 4,4-dimethyl-3-isoxazolidinone (81778-07-6) → clomazone (81777-89-1,89493-06-1)

Guidance literature:

With pyridin-3-ylamine; In water; at 120 ℃; for 9h; pH=9; Reagent/catalyst; Temperature; pH-value;

Reference yield: 36.0%

→ clomazone (81777-89-1,89493-06-1)

Guidance literature:

Reference yield:

3-Chloropivaloyl chloride (4300-97-4) + 1-chloro-2-(chloromethyl)benzene (611-19-8) → clomazone (81777-89-1,89493-06-1)

Guidance literature:

3-Chloropivaloyl chloride; With hydroxylamine hydrochloride; In water; at 15 - 25 ℃; pH=6.5 - 7;

With sodium chloride; In water; 1,2-dichloro-ethane; at 45 ℃; for 3h; pH=8.5;

1-chloro-2-(chloromethyl)benzene; With tetrabutylammomium bromide; In water; 1,2-dichloro-ethane; at 85 ℃; for 3.5h; Reagent/catalyst; Temperature; pH-value;

upstream raw materials:

3-chloro-N-(2-chlorobenzyl)-N-hydroxy-2,2-dimethyl-propionamide

3-Chloropivaloyl chloride

1-chloro-2-(chloromethyl)benzene

4,4-dimethyl-3-isoxazolidinone

Downstream raw materials:

4,4-dimethyl-3-isoxazolidinone

2-Chlorobenzyl alcohol

2-chloro-benzaldehyde

2-chlorobenzyl isocyanate

Refernces

• 1、 -. "Preparation method of 2-(2-chlorphenyl)methyl-4, 4-dimethyl-3-isoxazolone". Paragraph 0013-0048. . Retrieved 2021/11/10.
• 2、 -. "Method for producing carbendazim by electrodialysis method and production device thereof (by machine translation)". . . Retrieved 2020/04/17.