Clomazone

Clomazone is an agricultural herbicide, and has been the active ingredient of products named "Command" and "Commence". The molecule consists of a 2-chlorobenzyl group bound to a N-O heterocycle called isoxazolidinone. It is a white solid.

Clomazone

Names
Preferred IUPAC name 2-[(2-Chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one
Other names Dimethazone
Identifiers
CAS Number	81777-89-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3751 N
ChEMBL	ChEMBL1076356 Y
ChemSpider	49469 Y
ECHA InfoCard	100.125.682
KEGG	C11095 Y
PubChem CID	54778
UNII	570RAC03NF Y
CompTox Dashboard (EPA)	DTXSID1032355
InChI 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 Y Key: KIEDNEWSYUYDSN-UHFFFAOYSA-N Y 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 Key: KIEDNEWSYUYDSN-UHFFFAOYAD
SMILES Clc1ccccc1CN2OCC(C2=O)(C)C
Properties
Chemical formula	C12H14ClNO2
Molar mass	239.69806
Appearance	white solid
Melting point	33.9 °C (93.0 °F; 307.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Clomazone was first registered by the USEPA on March 8, 1993, and was commercialized by FMC Corporation. It is used for broadleaf weed control in several crops, including soybeans, peas, maize, oilseed rape, sugar cane, cassava, pumpkins and tobacco.^[1] It may be applied pre-emergence of incorporated before planting the crop. Clomazone is relatively volatile (vapor pressure is 19.2 mPa) and vapors induce striking visual symptoms on non-target sensitive plants. Clomazone undergoes biological degradation, exhibiting a soil half life of one to four months.^[2] Adsorption of the herbicide to soil solids slows degradation and volatilization.^[3] Encapsulation helps reduce volatility and therefore reduces off-target damage to sensitive plants.^[4]

Clomazone suppresses the biosynthesis of chlorophyll and other plant pigments.^[5][6]