# Profluralin
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> Markdown URL: https://mediated.wiki/source/Profluralin.md
> Source: https://en.wikipedia.org/wiki/Profluralin
> Source revision: 1349858483
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{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[{{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 }}]
| VaporPressure = 8.4 mPa[{{cite web |title=SAFETY DATA SHEET |url=http://cdn.chemservice.com/product/msdsnew/External/English/N-13098%20English%20SDS%20US.pdf |publisher=Chemservice Inc}}]
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|318|410}}
| PPhrases = {{P-phrases|264|273}}
| FlashPt =
| LD50 = 10000 mg/kg (rat, oral)[{{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 }}] Profluralin has largely fallen out of use.[{{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}}] It rose out of the related, still in common use, [trifluralin](/source/trifluralin).[{{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}}]
It was sold under the [tradename](/source/tradename)s "Pregard" and "Tolban" (Syngenta),[{{cite web |title=Tolban 4E Herbicide pesticide information |url=https://www.pomerix.com/pesticides/tolban-4e-herbicide |website=www.pomerix.com}}] {{convert|48,000|lbs|t}} was used in the US in 1974.[{{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}}] The USGS estimates that {{convert|5 to 65|e3lbs|t}} was used in 1994, with no usage after.[{{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}}]
Profluralin's [mode of action](/source/mode_of_action) is by binding to [tubulin](/source/tubulin) [microtubule](/source/microtubule)s as they form, blocking further growth. It shares the same mechanism and [resistance properties of trifluralin](/source/Trifluralin), and other dinitroanlines.[{{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}}] This makes it a [Group 3](/source/%3ACategory%3AGroup_3_herbicides) herbicide by [HRAC classification](/source/HRAC_classification). (AKA Australian Group D and global Group K1)
==Environmental Behaviour==
Environmental decomposition by [microörganism](/source/microorganism)s 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 [bird](/source/bird)s and [mammal](/source/mammal)s, though [bee](/source/bee)s and [fish](/source/fish) are affected. If applied in high doses to rats, they may exhibit [ataxia](/source/ataxia), slower breathing, salivation, [prostration](/source/prostration), hyperactivity or [dyspnea](/source/dyspnea). It interacts with [dsDNA](/source/dsDNA) via electrostatic binding.[{{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 }}]
== Safety ==
Profluralin is not toxic, not considered a [carcinogen](/source/carcinogen). Human harm is not expected, outside of eye irritation. Profluralin is very toxic to fish though, and is theorised to bioaccumulate in them.