Zytron
{{Short description|Weed control herbicide}}
{{Chembox
| Reference =
| ImageFile = Zytron.svg
| PIN = N-[(2,4-Dichlorophenoxy)-methoxyphosphinothioyl]propan-2-amine
| OtherNames = {{ubl|DMPA|O-2,4-Dichlorophenyl O-methyl isopropyl phosphoramidothioate}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8940
| KEGG_Ref = {{keggcite|changed|kegg}}
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| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI =
| StdInChI=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)
| StdInChIKey = PJFGPJQBWSEWKX-UHFFFAOYSA-N
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL =
| DrugBank = DB11768
| EC_number =
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 299-85-4
| PubChem = 9299
| UNII = IK51552IFH
| UNNumber =
| SMILES = CC(C)NP(=S)(OC)OC1=C(C=C(C=C1)Cl)Cl
}}
|Section2={{Chembox Properties
| C=10|H=14|Cl=2|N=1|O=2|P=1|S=1
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| Solubility =
| Solvent1 = acetone
| Solubility1 =
| VaporPressure = 6.14x10−5 mm Hg{{cite web |title=Zytron |url=https://pubchem.ncbi.nlm.nih.gov/compound/Zytron#section=Vapor-Pressure |website=pubchem.ncbi.nlm.nih.gov |language=en}}
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|Section3={{Chembox Hazards
| MainHazards =
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| LD50 = {{ubl|270 mg/kg (rat, oral)|>1000 mg/kg (dog, oral)}}
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Zytron, also known as DMPA, is a chlorophenoxy herbicide. It controls crabgrass and other weeds in turf preëmergently, and ants, chinch bugs and grubs.{{cite journal |last1=St. John, Jr. |first1=Leigh E. |last2=Lisk |first2=Donald J. |title=Metabolic studies with Zytron herbicide in a lactating cow |journal=Journal of Agricultural and Food Chemistry |date=January 1970 |volume=18 |issue=1 |pages=125–127 |doi=10.1021/jf60167a031|pmid=5535663 |bibcode=1970JAFC...18..125S }} It is used on baseball pitches in Australia.{{cite web |title=2019 Baseball_Australia_Facility_Resource_2019.pdf |url=https://www.baseballqueensland.com.au/wp-content/uploads/2023/06/2019-Field-Maintenance-Excerpt.pdf |publisher=Baseball Australia |access-date=5 November 2024 |date=2019}}
Zytron inhibits microtubule assembly, preventing mitosis. making it a Group 3 / D / K1, similar to dinitroanilines like trifluralin.{{cite web |title=List of Herbicides Globally |url=https://www.weedscience.org/Pages/Herbicide.aspx?MOAID=15# |website=www.weedscience.org}} It was tested and commercially available in the US in 1959, and applied at 10-20 lbs per acre on turf,{{cite journal |last1=Ahrens |first1=J. F. |last2=Olson |first2=A. R. |title=Prevention and Control of Crabgrass in Lawns |journal=The Connecticut Agricultural Experiment Station |date=March 1961 |issue=Bulletin 642 |url=https://portal.ct.gov/-/media/caes/documents/publications/bulletins/b642pdf.pdf |access-date=5 November 2024 |location=New Haven}} a high rate compared to other herbicides.
Zytron disappears almost completely from the body within one hour of mammalian exposure. It does not accumulate in soil and is non-harmful to microflora.{{cite journal |last1=Fields |first1=M.L. |last2=Hemphill |first2=D.D. |title=Effect of Zytron and Its Degradation Products on Soil Microorganisms |journal=Applied Microbiology |date=14 March 1966 |volume=14 |issue=5 |pages=724–731 |publisher=American Society for Microbiology |location=Department of Horticulture, University of Missouri|doi=10.1128/am.14.5.724-731.1966 |pmid=5970460 |pmc=1058404 }} DMPA has in testing been applied at rates as high as 67 lbs per acre.Gibeault V. A.mSkogley, C.R., Effects of DMPA (Zytron) on Colonial Bentgrass, Kentucky Bluegrass, and Red Fescue Root Growth, uly, 1967
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.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
Zytron has been sold under the tradenames "Dow Crabgrass Killer", "Dow 1329", "Dowco 118" and "T-H Crabgrass Killer."{{cite web |last1=Macksam |first1=William G. |last2=Frost |first2=Kenneth R. |last3=Martin |first3=Dean M. |title=Pre-Emergence Cr gence Crabgrass Contr ass Control |publisher=South Dakota State University |url=https://core.ac.uk/download/345017385.pdf |date=1963}}{{cite book |last1=Briggs |first1=Shirley A. |title=BASIC GUIDE TO PESTICIDES -- Their Characteristics and Hazards |date=1992 |publisher=Taylor&Francis |isbn=1-56032-253-5}}