Prodiamine

Prodiamine
Names
	IUPAC name 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)-1,3-benzenediamine
Identifiers
CAS Number	29091-21-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82032;
ChEMBL	ChEMBL1223140;
ChemSpider	31719;
ECHA InfoCard	100.044.914
EC Number	249-421-3;
KEGG	C18884;
PubChem CID	34469;
UNII	IJI5J414Q6;
CompTox Dashboard (EPA)	DTXSID1034210 ;
	InChI InChI=1S/C13H17F3N4O4/c1-3-5-18(6-4-2)11-9(19(21)22)7-8(13(14,15)16)10(17)12(11)20(23)24/h7H,3-6,17H2,1-2H3 Key: RSVPPPHXAASNOL-UHFFFAOYSA-N;
	SMILES CCCN(CCC)C1=C(C=C(C(=C1[N+](=O)[O-])N)C(F)(F)F)[N+](=O)[O-];
Properties
Chemical formula	C13H17F3N4O4
Molar mass	350.298 g·mol−1
Melting point	124–125 °C (255–257 °F; 397–398 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H332, H410
Precautionary statements	P261, P271, P273, P304+P312, P304+P340, P312, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Prodiamine is a preemergent herbicide of the dinitroaniline class. Prodiamine is used with crops such as soybeans, alfalfa, cotton, and ornamental crops. Prodiamine inhibits the formation of microtubules.^[2]

Prodiamine was developed by Sandoz AG and marketed beginning in 1987.^[3]

Prodiamine can be obtained from 2,4-dichlorobenzotrifluoride by reaction with nitric acid in the presence of sulfuric acid, dipropylamine, and ammonia.^[4]

References

^ Endeshaw, Molla M; Li, Catherine; Leon, Jessica de; Yao, Ni; Latibeaudiere, Kirk; Premalatha, Kokku; Morrissette, Naomi; Werbovetz, Karl A (2010). "Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii". Bioorganic & Medicinal Chemistry Letters. 20 (17): 5179. doi:10.1016/j.bmcl.2010.07.003. PMC 2922421.
^ "Herbicide Mode-Of-Action Summary". Purdue University.
^ "Prodiamin" (in German).
^ Thomas A. Unger (1996). Pesticide Synthesis Handbook. p. 877. ISBN 978-0-8155-1401-5.

[1] Endeshaw, Molla M; Li, Catherine; Leon, Jessica de; Yao, Ni; Latibeaudiere, Kirk; Premalatha, Kokku; Morrissette, Naomi; Werbovetz, Karl A (2010). "Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii". Bioorganic & Medicinal Chemistry Letters. 20 (17): 5179. doi:10.1016/j.bmcl.2010.07.003. PMC 2922421.

[2] "Herbicide Mode-Of-Action Summary". Purdue University.

[3] "Prodiamin" (in German).

[unger-4] Thomas A. Unger (1996). Pesticide Synthesis Handbook. p. 877. ISBN 978-0-8155-1401-5.

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