Clomazone

Clomazone
Skeletal formula of clomazone
Ball-and-stick model of the clomazone molecule
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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:3751 ☒N
ChEMBL
  • ChEMBL1076356 checkY
ChemSpider
  • 49469 checkY
ECHA InfoCard 100.125.682 Edit this at Wikidata
KEGG
  • C11095 checkY
PubChem CID
  • 54778
UNII
  • 570RAC03NF checkY
CompTox Dashboard (EPA)
  • DTXSID1032355 Edit this at Wikidata
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 checkY
    Key: KIEDNEWSYUYDSN-UHFFFAOYSA-N checkY
  • 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
  • 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 checkY☒N ?)
Infobox references
Chemical compound

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 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]

References

  1. ^ Tomlin, CD. 1997. The pesticide manual, 11th edition. British Crop Protection Council. Farnham, Surrey, UK. p 256-257. ISBN 978-1901396881.
  2. ^ Mervosh, T. L., G.K. Sims, and E.W. Stoller. 1995. Clomazone fate in soil as affected by microbial activity, temperature, and soil moisture. J. Agric. Food Chem. 43:537-543. https://doi.org/10.1021/jf00050a052.
  3. ^ Mervosh, T. L., G.K. Sims, E.W. Stoller, and T.R. Ellsworth. 1995. Clomazone sorption in soil: Incubation time, temperature, and soil moisture effects. J. Agric. Food Chem. 43:2295-2300. https://doi.org/10.1021/jf00056a062.
  4. ^ Mervosh, T. L., E.W. Stoller, T.R. Ellsworth, and G.K. Sims. 1995. Effects of starch encapsulation on clomazone and atrazine movement in soil and clomazone volatilization. Weed Science. 43:445-453. DOI: https://doi.org/10.1017/S0043174500081455.
  5. ^ Storzer, Werner "The residue behaviour of new herbicides in crop plants" Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 2002, vol. 54, 193-203.
  6. ^ Gara, Pedro M. David; Rosso, Janina A.; Martin, Marcela V.; Bosio, Gabriela N.; Gonzalez, Monica C.; Martire, Daniel O. "Characterization of humic substances and their role in photochemical processes of environmental interest" Trends in Photochemistry & Photobiology 2011, vol. 13, pages 51-70.
  • v
  • t
  • e
Anilides/anilinesAromatic acidsArsenicals
HPPD inhbitors
OrganophosphorusPhenoxy
Auxins
ACCase inhibitors
FOP herbicides
DIM herbicides
Protox inhibitors
Nitrophenyl ethers
Pyrimidinediones
Triazolinones
PyridinesQuaternary
Photosystem I inhibitors
Triazines
Photosystem II inhibitors
Ureas
Photosystem II inhibitors
ALS inhibitors
Others


Stub icon

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e