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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
  • 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
  • 54778
UNII
  • 570RAC03NF Y
  • DTXSID1032355
  • 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
  • Clc1ccccc1CN2OCC(C2=O)(C)C
Properties
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 ?)

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.
  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.
  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.
  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.
  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.


clomazone, agricultural, herbicide, been, active, ingredient, products, named, command, commence, molecule, consists, chlorobenzyl, group, bound, heterocycle, called, isoxazolidinone, white, solid, namespreferred, iupac, name, chlorophenyl, methyl, dimethyl, o. 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 NamesPreferred IUPAC name 2 2 Chlorophenyl methyl 4 4 dimethyl 1 2 oxazolidin 3 oneOther names DimethazoneIdentifiersCAS Number 81777 89 1 Y3D model JSmol Interactive imageChEBI CHEBI 3751 NChEMBL ChEMBL1076356 YChemSpider 49469 YECHA InfoCard 100 125 682KEGG C11095 YPubChem CID 54778UNII 570RAC03NF YCompTox Dashboard EPA DTXSID1032355InChI 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 YKey KIEDNEWSYUYDSN UHFFFAOYSA N YInChI 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 2H3Key KIEDNEWSYUYDSN UHFFFAOYADSMILES Clc1ccccc1CN2OCC C2 O C CPropertiesChemical formula C12H14ClNO2Molar mass 239 69806Appearance white solidMelting 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 Y N 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 References Edit Tomlin CD 1997 The pesticide manual 11th edition British Crop Protection Council Farnham Surrey UK p 256 257 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 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 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 Storzer Werner The residue behaviour of new herbicides in crop plants Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 2002 vol 54 193 203 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 amp Photobiology 2011 vol 13 pages 51 70 This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Clomazone amp oldid 1119345577, wikipedia, wiki, book, books, library,

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