Profluralin
| |
| Names | |
|---|---|
| Preferred IUPAC name (N-(Cyclopropylmethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)aniline | |
| Other names N-(Cyclopropylmethyl)-α,α,α-trifluoro-2,6-dinitro-N-propyl-p-toluidine; N-(Cyclopropylmethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)-benzenamine | |
| Identifiers | |
| ECHA InfoCard | 100.043.309 |
CompTox Dashboard (EPA) |
|
| Properties | |
| C14H16F3N3O4 | |
| Molar mass | 347.294 g·mol−1 |
| Appearance | Yellow/Orange Solid[1] |
| Density | 1380 kg/m3[1] |
| Melting point | 32 °C (90 °F; 305 K)[1] |
| 0.1 ppm[2] | |
| Vapor pressure | 8.4 mPa[3] |
| Hazards | |
| GHS labelling:[1] | |
 
| |
| Warning | |
| H318, H410 | |
| P264, P273 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
10000 mg/kg (rat, oral)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Profluralin is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others.[4] Profluralin has largely fallen out of use.[3] It rose out of the related, still in common use, trifluralin.[5]
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.[4]
It was sold under the tradenames "Pregard" and "Tolban" (Syngenta),[3] registered in August 1975 and expiring in April 1984. Tolban was a 45% profluralin emulsifiable concentrate.[6] 48,000 pounds (22 t) was used in the US in 1974.[7]
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.[8]
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.[1]
References
- ^ a b c d e f "SAFETY DATA SHEET" (PDF). Chemservice Inc.
- ^ Huffman, J. B.; Camper, N. D. (1978). "Growth Inhibition in Tobacco (Nicotiana tabacum) Callus by 2,6-Dinitroaniline Herbicides and Protection by D-α-Tocopherol Acetate". Weed Science. 26 (6): 527–530. ISSN 0043-1745.
- ^ a b c Hertfordshire, University of. "Profluralin (Ref: CGA 10832)". sitem.herts.ac.uk. Retrieved 18 October 2024.
- ^ a b Morawska, Kamila; Jedlińska, Katarzyna; Smarzewska, Sylwia; Metelka, Radovan; Ciesielski, Witold; Guziejewski, Dariusz (September 2019). "Analysis and DNA interaction of the profluralin herbicide". Environmental Chemistry Letters. 17 (3): 1359–1365. Bibcode:2019EnvCL..17.1359M. doi:10.1007/s10311-019-00865-1.
- ^ Moore, Mark (March 2012). "Top 10 classic herbicides".
- ^ "Tolban 4E Herbicide pesticide information". www.pomerix.com.
- ^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
- ^ Chen, Jinyi; Yu, Qin; Patterson, Eric; Sayer, Chad; Powles, Stephen (25 March 2021). "Dinitroaniline Herbicide Resistance and Mechanisms in Weeds". Frontiers in Plant Science. 12. doi:10.3389/fpls.2021.634018. PMC 8027333. PMID 33841462.
Links
- Profluralin in the Pesticide Properties DataBase (PPDB)