Zytron

Zytron
Names
	Preferred IUPAC name N-[(2,4-dichlorophenoxy)-methoxyphosphinothioyl]propan-2-amine
	Other names DMPA; o-2,4-dichlorophenyl o-methyl isopropyl phosphoramidothioate;
Identifiers
CAS Number	299-85-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	8940 ;
DrugBank	DB11768;
PubChem CID	9299;
UNII	IK51552IFH;
CompTox Dashboard (EPA)	DTXSID1058052 ;
	InChI InChI=1S/C10H14Cl2NO2PS/c1-7(2)13-16(17,14-3)15-10-5-4-8(11)6-9(10)12/h4-7H,1-3H3,(H,13,17) Key: PJFGPJQBWSEWKX-UHFFFAOYSA-N;
	SMILES CC(C)NP(=S)(OC)OC1=C(C=C(C=C1)Cl)Cl;
Properties
Chemical formula	C10H14Cl2NO2PS
Molar mass	314.16 g·mol−1
Appearance	Solid
Vapor pressure	6.14x10-5 mm Hg
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	270 mg/kg (rat, oral); >1000 mg/kg (dog, oral);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Zytron, also known as DMPA, is a chlorophenoxy herbicide.^[1] It controls crabgrass and other weeds in turf preëmergently, and ants, chinch bugs and grubs.^[2] It is used on baseball pitches in Australia.^[3]

Zytron inhibits microtubule assembly, preventing mitosis. making it a Group 3 / D / K1, similar to dinitroanilines like trifluralin.^[4] It was tested and commercially available in the US in 1959, and applied at 10-20 lbs per acre on turf,^[5] a high rate compared to other herbicides.

Zytron disappears almost completely from the body within one hour of mammalian exposure.^[2] It does not accumulate in soil and is non-harmful to microflora.^[6] DMPA has in testing been applied at rates as high as 67 lbs per acre.^[7]

Zytron may cause neurotoxicity in chickens. It is an organophosphorus ester, and other such chemicals are known to cause similar neurotoxicity. 100 mg/kg daily for 10 days was considered the minimum effective dose to observably alter hens' behaviour.^[8]

Zytron has been sold under the tradenames "Dow Crabgrass Killer", "Dow 1329", "Dowco 118" and "T-H Crabgrass Killer."^[9]^[10]

References

^ ^a ^b ^c ^d "Zytron". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b St. John, Jr., Leigh E.; Lisk, Donald J. (January 1970). "Metabolic studies with Zytron herbicide in a lactating cow". Journal of Agricultural and Food Chemistry. 18 (1): 125–127. Bibcode:1970JAFC...18..125S. doi:10.1021/jf60167a031. PMID 5535663.
^ "2019 Baseball_Australia_Facility_Resource_2019.pdf" (PDF). Baseball Australia. 2019. Retrieved 5 November 2024.
^ "List of Herbicides Globally". www.weedscience.org.
^ Ahrens, J. F.; Olson, A. R. (March 1961). "Prevention and Control of Crabgrass in Lawns" (PDF). The Connecticut Agricultural Experiment Station (Bulletin 642). New Haven. Retrieved 5 November 2024.
^ Fields, M.L.; Hemphill, D.D. (14 March 1966). "Effect of Zytron and Its Degradation Products on Soil Microorganisms". Applied Microbiology. 14 (5). Department of Horticulture, University of Missouri: American Society for Microbiology: 724–731. doi:10.1128/am.14.5.724-731.1966. PMID 5970460.
^ Gibeault V. A.mSkogley, C.R., Effects of DMPA (Zytron) on Colonial Bentgrass, Kentucky Bluegrass, and Red Fescue Root Growth, uly, 1967
^ B. M. Francis, L. G. Hansen & R. L. Metcalf (1980) Neurotoxicity of halogenated o‐phenyl o‐alkyl alkylphosphonothioates, Journal of Environmental Science & Health Part B, 15:4, 313-331, DOI: 10.1080/03601238009372186
^ Macksam, William G.; Frost, Kenneth R.; Martin, Dean M. (1963). "Pre-Emergence Cr gence Crabgrass Contr ass Control" (PDF). South Dakota State University.
^ Briggs, Shirley A. (1992). BASIC GUIDE TO PESTICIDES -- Their Characteristics and Hazards. Taylor&Francis. ISBN 1-56032-253-5.

[pubchem-1] "Zytron". pubchem.ncbi.nlm.nih.gov.

[cow-2] St. John, Jr., Leigh E.; Lisk, Donald J. (January 1970). "Metabolic studies with Zytron herbicide in a lactating cow". Journal of Agricultural and Food Chemistry. 18 (1): 125–127. Bibcode:1970JAFC...18..125S. doi:10.1021/jf60167a031. PMID 5535663.

[3] "2019 Baseball_Australia_Facility_Resource_2019.pdf" (PDF). Baseball Australia. 2019. Retrieved 5 November 2024.

[4] "List of Herbicides Globally". www.weedscience.org.

[5] Ahrens, J. F.; Olson, A. R. (March 1961). "Prevention and Control of Crabgrass in Lawns" (PDF). The Connecticut Agricultural Experiment Station (Bulletin 642). New Haven. Retrieved 5 November 2024.

[6] Fields, M.L.; Hemphill, D.D. (14 March 1966). "Effect of Zytron and Its Degradation Products on Soil Microorganisms". Applied Microbiology. 14 (5). Department of Horticulture, University of Missouri: American Society for Microbiology: 724–731. doi:10.1128/am.14.5.724-731.1966. PMID 5970460.

[7] Gibeault V. A.mSkogley, C.R., Effects of DMPA (Zytron) on Colonial Bentgrass, Kentucky Bluegrass, and Red Fescue Root Growth, uly, 1967

[8] B. M. Francis, L. G. Hansen & R. L. Metcalf (1980) Neurotoxicity of halogenated o‐phenyl o‐alkyl alkylphosphonothioates, Journal of Environmental Science & Health Part B, 15:4, 313-331, DOI: 10.1080/03601238009372186

[9] Macksam, William G.; Frost, Kenneth R.; Martin, Dean M. (1963). "Pre-Emergence Cr gence Crabgrass Contr ass Control" (PDF). South Dakota State University.

[10] Briggs, Shirley A. (1992). BASIC GUIDE TO PESTICIDES -- Their Characteristics and Hazards. Taylor&Francis. ISBN 1-56032-253-5.

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