Nitrofor

Not to be confused with "Nitrofor", a trademark of the drug Nitrofurantoin[1].
Nitrofor
Names
Preferred IUPAC name
N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)aniline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 982-770-6
  • InChI=1S/C11H12F3N3O4/c1-3-15(4-2)10-8(16(18)19)5-7(11(12,13)14)6-9(10)17(20)21/h5-6H,3-4H2,1-2H3
    Key: NLLHXVBITYTYHA-UHFFFAOYSA-N
  • CCN(CC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
Properties
C11H12F3N3O4
Molar mass 307.229 g·mol−1
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H317, H331, H351, H410
P203, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P316, P318, P321, P330, P333+P317, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nitrofor is a dinitroaniline herbicide, useful for weed control in cabbage, tomato, and cotton crops,[2] used in the Soviet Union.[3] It is not approved in the EU.[4] It can be applied at 3-6 kg/ha, and works by the inhibition of microtubule formation mode of action, making it an HRAC Group D / K3 / 3 herbicide.[2] It appears not to be in current use anywhere.

The USSR tested it for senna (cassia acutifolia) crops. The closely related herbicide trifluralin was slightly more effective than nitrofor, but had to be imported to the USSR, whereas nitrofor was produced domestically. Also tested, were prometryn, simazine, linuron and maloran, with trifluralin and prometryn being found most effective.[3]

In a Soviet test in the 1970s, nitrofor at 3 kg/Ha increased the levels of NPK (nitrogen, phosphorus and potassium), in leached heavy-loam chernozem soil. The nitrofor was pre-plant incorporated. Final NPK levels were 1.6-2.0 times greater in castor beans and 5 times greater in the seed.[5]

An American test in the 1960s compared trifluralin analogs, one being nitrofor, which is equivalent to trifluralin with ethyl groups instead of propyls. Trifluralin itself was the most active agent, however nitrofor was among a few analogs recommended for further testing, still having high herbicidal activity but offering greater crop safety.[6]

References

  1. ^ "Nitrofurantoin (IARC Summary & Evaluation, Volume 50, 1990)". inchem.org. 11 November 1997. Retrieved 5 March 2025.
  2. ^ a b Nyporko, A. Yu.; Yemets, A. I.; Brytsun, V. N.; Lozinsky, M. O.; Blume, Ya. B. (August 2009). "Structural and biological characterization of the tubulin interaction with dinitroanilines". Cytology and Genetics. 43 (4): 267–282. doi:10.3103/S0095452709040082.
  3. ^ a b Sulmankulov, R.; Bukina, N. V.; Pushkina, G. P. (May 1976). "Herbidices in senna (Cassia acutifolia) crops". Pharmaceutical Chemistry Journal. 10 (5): 633–635. doi:10.1007/BF00757693. Retrieved 29 October 2025.
  4. ^ Giglio, Anita; Vommaro, Maria Luigia (1 November 2022). "Dinitroaniline herbicides: a comprehensive review of toxicity and side effects on animal non-target organisms". Environmental Science and Pollution Research. 29 (51): 76687–76711. Bibcode:2022ESPR...2976687G. doi:10.1007/s11356-022-23169-4. PMC 9581837. PMID 36175724.
  5. ^ Vasil'ev, D. S.; Baranova, L. A. (1975). "The effect of Nitrofor on the nutrient status of the soil in castor-bean crops". Agrokhimiya. 12 (4). Krasnodar, USSR: Vses. n-i Inst. maslich. Kul'tur: 121–123.
  6. ^ Gentner, W. A. (April 1966). "Herbicidal Properties of Trifluralin Analogs". Weeds. 14 (2): 176–178. doi:10.2307/4040959. JSTOR 4040959.

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