{{Chembox | ImageFile = Profluralin v3.svg | ImageSize = 180px | PIN = (''N''-(Cyclopropylmethyl)-2,6-dinitro-''N''-propyl-4-(trifluoromethyl)aniline | OtherNames = ''N''-(Cyclopropylmethyl)-α,α,α-trifluoro-2,6-dinitro-''N''-propyl-''p''-toluidine; ''N''-(Cyclopropylmethyl)-2,6-dinitro-''N''-propyl-4-(trifluoromethyl)-benzenamine |Section1={{Chembox Identifiers | CASNo = 26399-36-0 | ChEBI = 82191 | ChEMBL = 1256764 | ChemSpiderID = 30913 | EC_number = 247-656-6 | KEGG = C19065 | PubChem = 33500 | UNII = 36W2L722UX | StdInChI=1S/C14H16F3N3O4/c1-2-5-18(8-9-3-4-9)13-11(19(21)22)6-10(14(15,16)17)7-12(13)20(23)24/h6-7,9H,2-5,8H2,1H3 | StdInChIKey = ITVQAKZNYJEWKS-UHFFFAOYSA-N | SMILES = CCCN(CC1CC1)C2=C(C=C(C=C2[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-] }} |Section2={{Chembox Properties | C=14|H=16|F=3|N=3|O=4 | Appearance = Yellow/Orange Solid<ref name = "sds"/> | Density = 1380 kg/m<sup>3</sup><ref name = "sds"/> | MeltingPtC = 32 | MeltingPt_ref = <ref name = "sds"/> | BoilingPtC = | BoilingPt_notes = | BoilingPt_ref = | Solubility = 0.1 ppm<ref>{{cite journal |last1=Huffman |first1=J. B. |last2=Camper |first2=N. D. |title=Growth Inhibition in Tobacco (Nicotiana tabacum) Callus by 2,6-Dinitroaniline Herbicides and Protection by D-α-Tocopherol Acetate |journal=Weed Science |date=1978 |volume=26 |issue=6 |pages=527–530 |doi=10.1017/S0043174500064468 |jstor=4042920 |bibcode=1978WeedS..26..527H |url=https://www.jstor.org/stable/4042920 |issn=0043-1745|url-access=subscription }}</ref> | VaporPressure = 8.4 mPa<ref name = "database"/> }} |Section3={{Chembox Hazards | MainHazards = | GHS_ref = <ref name="sds">{{cite web |title=SAFETY DATA SHEET |url=http://cdn.chemservice.com/product/msdsnew/External/English/N-13098%20English%20SDS%20US.pdf |publisher=Chemservice Inc}}</ref> | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|318|410}} | PPhrases = {{P-phrases|264|273}} | FlashPt = | LD50 = 10000 mg/kg (rat, oral)<ref name = "sds"/> | AutoignitionPt = }} }} '''Profluralin''' is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others.<ref name = "dna">{{cite journal |last1=Morawska |first1=Kamila |last2=Jedlińska |first2=Katarzyna |last3=Smarzewska |first3=Sylwia |last4=Metelka |first4=Radovan |last5=Ciesielski |first5=Witold |last6=Guziejewski |first6=Dariusz |title=Analysis and DNA interaction of the profluralin herbicide |journal=Environmental Chemistry Letters |date=September 2019 |volume=17 |issue=3 |pages=1359–1365 |doi=10.1007/s10311-019-00865-1|bibcode=2019EnvCL..17.1359M |doi-access=free |hdl=10195/75006 |hdl-access=free }}</ref> Profluralin has largely fallen out of use.<ref name="database">{{cite web |last1=Hertfordshire |first1=University of |title=Profluralin (Ref: CGA 10832) |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/2843.htm |website=sitem.herts.ac.uk |access-date=18 October 2024}}</ref> It rose out of the related, still in common use, trifluralin.<ref>{{cite web |last1=Moore |first1=Mark |title=Top 10 classic herbicides |url=https://www.farmprogress.com/crop-protection/top-10-classic-herbicides |date=March 2012}}</ref>
It was sold under the tradenames "Pregard" and "Tolban" (Syngenta),<ref name = "database"/> registered in August 1975 and expiring in April 1984. Tolban was a 45% profluralin emulsifiable concentrate.<ref>{{cite web |title=Tolban 4E Herbicide pesticide information |url=https://www.pomerix.com/pesticides/tolban-4e-herbicide |website=www.pomerix.com}}</ref> {{convert|48,000|lbs|t}} was used in the US in 1974.<ref>{{cite web |title=Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974 |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=91012P4O.txt |website=epa.gov |publisher=EPA |date=1977}}</ref> The USGS estimates that {{convert|5 to 65|e3lbs|t}} was used in 1994, with no usage after.<ref>{{cite web |title=2019 Pesticide Use Maps |url=https://water.usgs.gov/nawqa/pnsp/usage/maps/show_map.php?year=2019&map=PROFLURALIN&hilo=L&disp=Profluralin |website=water.usgs.gov |publisher=USGS |access-date=15 August 2025}}</ref>
Profluralin's mode of action is by binding to tubulin microtubules as they form, blocking further growth. It shares the same mechanism and resistance properties of trifluralin, and other dinitroanlines.<ref name="frontiers">{{cite journal |last1=Chen |first1=Jinyi |last2=Yu |first2=Qin |last3=Patterson |first3=Eric |last4=Sayer |first4=Chad |last5=Powles |first5=Stephen |title=Dinitroaniline Herbicide Resistance and Mechanisms in Weeds |journal=Frontiers in Plant Science |date=25 March 2021 |volume=12 |article-number=634018 |doi=10.3389/fpls.2021.634018|doi-access=free |pmid=33841462 |pmc=8027333 |bibcode=2021FrPS...1234018C |author-link5=Stephen Powles}}</ref> This makes it a Group 3 herbicide by HRAC classification. (AKA Australian Group D and global Group K1)
==Environmental Behaviour== Environmental decomposition by microörganisms happens in soil and water. Typical soil half-lives for profluralin are 80-160 days. Profluralin is adsorbed into plantmatter, so there is potential that it stay in crops after harvest. It is practically non-toxic to birds and mammals, though bees and fish are affected. If applied in high doses to rats, they may exhibit ataxia, slower breathing, salivation, prostration, hyperactivity or dyspnea. It interacts with dsDNA via electrostatic binding.<ref name = "dna"/>
Microörganisms in sewage cometabolise profluralin, trifluralin, fluchloralin and nitrofen; i.e. enzymes from other active metabolic processes also break up these chemicals. Over 88 days, profluralin levels reduced by 87% under aerobic conditions, into 9 metabolite products. Discontinuous anaerobic conditions slowed the process to a 23% reduction in the same time, with 5 metabolites.<ref>{{cite journal |last1=Jacobson |first1=Stuart N. |last2=O'Mara |first2=Nancy L. |last3=Alexander |first3=Martin |title=Evidence for Cometabolism in Sewage |journal=Applied and Environmental Microbiology |date=November 1980 |volume=40 |issue=5 |pages=917–921 |doi=10.1128/aem.40.5.917-921.1980|pmc=291690 |bibcode=1980ApEnM..40..917J }}</ref>
== Safety == Profluralin is not toxic, not considered a carcinogen. Human harm is not expected, outside of eye irritation. Profluralin is very toxic to fish though, and is theorised to bioaccumulate in them.<ref name = "sds"/>
== References == {{reflist}}
== Links == * {{PPDB|2843}}
{{Herbicides}} {{Aniline Herbicides}}
Category:Preemergent herbicides Category:Anilines Category:Trifluoromethyl compounds Category:Nitro compounds Category:Cyclopropyl compounds Category:Group 3 herbicides Category:Dinitroaniline herbicides