Profluralin

{{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

| Density = 1380 kg/m³

| MeltingPtC = 32

| MeltingPt_ref =

| BoilingPtC =

| BoilingPt_notes =

| BoilingPt_ref =

| Solubility = 0.1 ppm{{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 |url=https://www.jstor.org/stable/4042920 |issn=0043-1745|url-access=subscription }}

| VaporPressure = 8.4 mPa

}}

|Section3={{Chembox Hazards

| MainHazards =

| GHS_ref = {{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)

| AutoignitionPt =

}}

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Profluralin is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others.{{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.{{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}}

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.

It was sold under the tradenames "Pregard" and "Tolban" (Syngenta), registered in August 1975 and expiring in April 1984. Tolban was a 45% profluralin emulsifiable concentrate.{{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}}

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.{{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 |doi=10.3389/fpls.2021.634018|doi-access=free |pmid=33841462 |pmc=8027333 }}