Tri-allate

{{Chembox | ImageFile = Tri-allate.svg | ImageSize = 180px | PIN = S-(2,3,3-trichloroprop-2-en-1-yl) di(propan-2-yl)carbamothioate | OtherNames = {{UBL|Triallate| S-2,3,3-tricloroallyl di-isopropylthiocarbamate|S-(2,3,3-trichloro-2-propenyl) bis(1-methylethyl)carbamothioate}} |Section1={{Chembox Identifiers | CASNo = 2303-17-5 | ChEBI = 81978 | ChEMBL = 1884767 | ChemSpiderID = 5342 | EC_number = 218-962-7 | KEGG = C18813 | PubChem = 5543 | UNII = A9S097HS99 | UNNumber = 2588 (TRIALLATE, [SOLID]) | StdInChI= InChI=1S/C10H16Cl3NOS/c1-6(2)14(7(3)4)10(15)16-5-8(11)9(12)13/h6-7H,5H2,1-4H3 | StdInChIKey = MWBPRDONLNQCFV-UHFFFAOYSA-N | SMILES = CC(C)N(C(C)C)C(=O)SCC(=C(Cl)Cl)Cl }} |Section2={{Chembox Properties | C=10|H=16|Cl=3|N=1|O=1|S=1 | Appearance = White crystalline solid<ref name = "database"/> or amber liquid<ref name="epa 1980">{{cite web |title=Triallate: Decision Document |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=9101D8XC.txt |website=nepis.epa.gov |publisher=US EPA |date=November 1980}}</ref> | Density = 1.27<ref name = "database"/> | MeltingPtC =33.5 | MeltingPt_ref =<ref name = "database"/> | BoilingPtC = 279 | BoilingPt_notes = 148°C also claimed<ref name = "epa 1980"/> | BoilingPt_ref =<ref name = "database"/> | Solubility = 4.1 mg/L<ref name = "database"/> | VaporPressure = 12 mPa<ref name = "database"/> }} |Section3={{Chembox Hazards | MainHazards = | GHS_ref = | GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} | GHSSignalWord = Warning | HPhrases = {{HPhrases|373|410|302|317}}<ref name="4f sds">{{cite web |title=4Farmers Tri-Allate 500 EC SDS |url=https://4farmers.com.au/wp-content/uploads/2021/03/4FARMERS-TRI-ALLATE-500-EC-SELECTIVE-HERBICIDE-v2.pdf |publisher=4Farmers Australia}}</ref> | PPhrases = {{P-phrases|260|261|264|270|272|273|280|301+317|302+352|319|321|330|333+317|362+364|391|501}} | FlashPt = | LD50 = {{ubl|1700mg/kg (rat, oral)|930mg/kg (mouse, oral)|3500mg/kg (dermal, rat)<ref name = "4f sds"/>}} | AutoignitionPt = }} }} '''Tri-allate''' or '''triallate''' is a selective preëmergent thiocarbamate herbicide, used to control wild oats and sundry grasses and broadleaf weeds, often co-applied with trifluralin,<ref name = "4f leaflet"/> which is much weaker against wild oats than tri-allate. Residual control can be expected for 6 to 8 weeks. It is used in Australia,<ref name = "4f infosheet"/> India<ref>{{cite book |last1=Paranjape |first1=Kalyani |last2=Gowariker |first2=Vasant |last3=Krishnamurthy |first3=V.N. |last4=Gowariker |first4=Sudha |publisher=CABI |date = 2015 |title=The Pesticide Encyclopedia |isbn=978-1-78064-014-3}}</ref> and the United States.<ref name="usa 2023">{{cite web |title=US EPA, Pesticide Product Label, TRIALLATE/FAR-GO HERBICIDE,09/23/2024 |url=https://www3.epa.gov/pesticides/chem_search/ppls/010163-00286-20240923.pdf |website=www3.epa.gov |access-date=17 May 2025}}</ref> It was first registered in 1961.<ref name = "epa 2001"/>

In 2001, US agriculture used {{convert|2.3|e6lb|t}} annually.<ref name="epa 2001">{{cite web |title=R.E.D. Facts Triallate |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=200005E9.txt |publisher=US EPA}}</ref>

Tri-allate is a mitosis-inhibitor; its HRAC classification is Group J (Aus), Group K3 (global), Group 15 (numeric).<ref name = "4f infosheet"/><ref name = "database">{{cite journal |last1=Lewis |first1=Kathleen A. |last2=and Green |first2=Andrew |title=An international database for pesticide risk assessments and management |journal=Human and Ecological Risk Assessment|date=18 May 2016 |volume=22 |issue=4 |pages=1050–1064 |doi=10.1080/10807039.2015.1133242|bibcode=2016HERA...22.1050L |hdl=2299/17565 |hdl-access=free }}</ref> Affected weeds are prevented from germinating, or their shoots will be swollen and bright green.<ref name = "4f infosheet"/>

== Environmental behaviour == Under very dry conditions, tri-allate can persist in soil for several months, and can damage field oats and sorghum.<ref name = "4f leaflet"/> Degradation is dependent on soil microörganisms and moisture levels.<ref name = "epa 1980"/> Tri-allate is nontoxic to birds and bees, though it is very toxic to aquatic life. It doesn't bioaccumulate in plants, and has low mobility in soil.<ref name = "4f sds"/> The aquatic toxicity is most potent against invertebrates and algae.<ref name = "database"/> The EPA says "the overall ecological risk associated with the use of triallate is low".<ref name = "epa 2001"/>

The average soil half life is 82 days in "typical" conditions;<ref name = "4f sds"/> it is also measured at 46 days, under "field" conditions. Similar half-life is seen in water sediment and in acidic (pH 9) solution.<ref name = "database"/>

== Properties == Triallate is synthesised from diisopropylamine, phosgene and 2,3,4-trichloro-phenyl-1-thiol.<ref>{{cite web |title=Source Assessment : Pesticide Manufacturing Air Emissions, Overview and Prioritization |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=9101Y8ME.txt |website=nepis.epa.gov |date=1978}}</ref> Its surface tension is 0.049 N/m, as a 90% solution at 20&nbsp;°C.<ref name = "database"/> Monsanto manufactured it in the 1960s by the reaction of diisopropylthiocarbamate salt with 1,1,1,3-tetrachloro-propene.<ref name = "epa 1980"/> It is soluble in acetone, ether, ethyl alcohol, heptane, benzene, ethyl acetate and most organic solvents.<ref name = "extox"/>

Diallate is almost identical, but missing one of triallate's 3 chlorine atoms. Unlike triallate, it has cis- and trans- isomers.<ref name = "epa 1980"/>

== Health == Exposure to large amounts of tri-allate may harm the liver, spleen and kidneys.<ref name = "database"/> The EPA considers tri-allate to be a possible carcinogen, the result being "borderline" statistically significant in a trial on mice, though their rough estimate is that the chance of cancer from dietary triallate is one in 14 million.<ref name = "epa 2001"/> This trial only showed an increased incidence of tumors in one measured category, in a sample size of 15. Diallate, a very similar herbicide, was carcinogenic, possibly prompting the concern for triallate.<ref name = "epa 1980"/>

In tests on rabbits, no fetotoxic or teratogenic effects were observed, although a small decrease of birth weight was strongly evidenced.<ref name = "epa 1980"/>

== Regulatory status == Tri-allate is limited to the US states of California, Colorado, Idaho, Kansas, Minnesota, Montana, Nebraska, Nevada, North Dakota, Oregon, South Dakota, Utah, Washington and Wyoming, as of 2023.<ref name = "usa 2023"/> In Australia, all states allow it to control wild oats and most allow its broader use in combination with trifluralin.<ref name = "4f leaflet"/> It is used in the United Kingdom, Morocco and the EU states of Belgium, France, Ireland and the Netherlands.<ref name = "database"/>

== Application == It is incorporated to soil pre-sowing or (IBS) incorporated by sowing,<ref name="4f leaflet">{{cite web |title=4Farmers Tri-Allate 500 EC Leaflet |url=https://4farmers.com.au/wp-content/uploads/2018/06/63450-Tri-Allate-500-Leaflet-297x210-1.pdf |publisher=4Farmers Australia}}</ref> and is applied immediately before or up to 3 weeks before sowing. It is recommended to incorporate it 2–4&nbsp;cm deep, and within 6 hours if the soil is moist, or 24 hours if dry, to minimise volatilisation. Proper incorporation is essential for efficacy,<ref name="4f infosheet">{{cite web |title=4Farmers Tri-Allate 500 EC Infosheet |url=https://4farmers.com.au/wp-content/uploads/2018/06/4F-Tri-Allate-500-EC.pdf |publisher=4Farmers Australia}}</ref> and two-pass incorporation is needed for maximum efficacy. Efficacy can also be reduced if the top 2&nbsp;cm of soil is very dry.<ref name = "4f leaflet"/>

Tri-allate is applied at 0.8-1.0&nbsp;kg/Ha (0.71-0.89&nbsp;lbs/ac) in Australia, with a spraywater volume of 30 to 100 L/Ha (3.2-10.7 US gal/ac). Triallate is sold as an emulsifiable concentrate of 500 g/L active ingredient.<ref name = "4f infosheet"/>

=== Compatibility === Tri-allate is compatible with spray mixes containing chlorsulfuron, diclofop-methyl, trifluralin, glyphosate and oryzalin.<ref name = "4f leaflet"/>

=== Crops applied to === Tri-allate is applied to wheat, triticale, chickpeas, barley, peas, linseed, lupins, canola, faba beans and safflower.<ref name = "4f leaflet"/> It was used on canary grass, but this registration was not renewed by the manufacturers, circa 2000.<ref name = "epa 2001"/>

=== Weeds controlled === Tri-allate is used to control wild oats, annual ryegrass, wireweed, phalaris spp, fumitory, cereal oats, sand fescue, silvergrass, wintergrass, paradoxa grass (canary grass), corn gromwell (sheepweed) and rough poppy. It suppresses brome grass, barleygrass, cornered jack (doublegee), caltrop (yellowvine & bullhead), yellow burr weed, deadnettle and speedwell.<ref name = "4f leaflet"/>

=== Tradenames === Triallate has been sold as ''Avadex'', ''Buckle'', ''Far-Go'', ''Showdown'',<ref name = "extox">{{cite web |title=EXTOXNET PIP - TRIALLATE |url=http://extoxnet.orst.edu/pips/trialla.htm |website=extoxnet.orst.edu}}</ref> ''Check Mate'',<ref>{{cite web |title=Apparent Check Mate 20L Active: 500g/L Triallate Comparable to Nufarm Avadex Xtra |url=https://www.fmb.com.au/apparent-check-mate-20l-active-500g-l-triallate-comparable-to-nufarm-avadex-xtra.html |website=www.fmb.com.au |access-date=17 May 2025 |language=en}}</ref> ''Triallate Gold'',<ref>{{cite web |title=Genfarm Triallate Gold 500 Selective Herbicide |url=https://www.genfarm.com.au/crop-protection/herbicides/genfarm-triallate-gold-500-selective-herbicide |website=Genfarm |language=en}}</ref> ''Triallate''<ref>{{cite web |title=Tri-Allate 500 EC Herbicide |url=https://www.imtrade.com.au/product/tri-allate-500-ec-herbicide/ |website=Imtrade CropScience}}</ref> and ''Tri-Allate''.<ref>{{cite web |title=TRI-ALLATE 500 EC {{!}} 4Farmers |url=https://4farmers.com.au/products/herbicides/triallate-500ec/ |website=4farmers.com.au |publisher=4Farmers Australia}}</ref>

== References == {{reflist}}

== Links == *{{PPDB|650}}

{{Herbicides}}

Category:Thiocarbamates Category:Diisopropylamino compounds Category:Organochlorides Category:Group 8 herbicides Category:Group 15 herbicides Category:Preemergent herbicides