Dinitramine

Dinitramine is a preëmergent dinitroaniline herbicide incorporated into soil to control weeds for months after.^[2][3] It is no longer approved in the United States, and is not in the European Union,^[4] though in Iran it has been used to control annual grasses and broadleaf weeds in cotton and soybeans,^[5] as it was in the U.S. as of 1975,^[6] where it was also used on sunflower.^[3]

Dinitramine

Names
Preferred IUPAC name N,N-Diethyl-2,6-dinitro-4-(trifluoromethyl)benzene-1,3-diamine
Other names Cobex (trademark) N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)-m-phenylenediamine N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)-1,3-benzenediamine
Identifiers
CAS Number	29091-05-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81959
ChEMBL	ChEMBL1223066
ChemSpider	31718 N
ECHA InfoCard	100.044.912
EC Number	249-419-2
KEGG	C18785
PubChem CID	34468
UNII	XHQ6D15979
CompTox Dashboard (EPA)	DTXSID9040265
InChI InChI=1S/C11H13F3N4O4/c1-3-16(4-2)9-7(17(19)20)5-6(11(12,13)14)8(15)10(9)18(21)22/h5H,3-4,15H2,1-2H3 Key: OFDYMSKSGFSLLM-UHFFFAOYSA-N
SMILES CCN(CC)c1c(cc(c(N)c1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O
Properties
Chemical formula	C11H13F3N4O4
Molar mass	322.244 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H312, H400
Precautionary statements	P273, P280, P302+P352, P317, P321, P362+P364, P391, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)	3,000 mg/kg (rat, oral)[1] 10,000 mg/kg (mallard ducks) 1200 mg/kg (bobwhite quail)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dinitramine is chemically similar to trifluralin and other dinitroanilines, with which it shares many characteristics, such as mode of action and resistance information. In a 1977 trial, it was the only dinitroaniline to exceed trifluralin's phytotoxicity by a significant margin, on sorghum, soybeans, jimsonweed and velvetleaf, although falling short on morning glory.^[7] Trifluralin's greater popularity may be helped because toxicity to crops is usually considered bad.

Cobex (or Kobex) was a dinitramine formulation sold in the U.S. by the United States Borax & Chemical Corporation, and introduced in 1973.^[8] It was an emulsifiable concentrate of 2 pounds per gallon dinitramine (25% by weight) used on soybeans, cotton and sunflower, applied at rates of 0.25 to 0.75 pounds per acre to crops.^[3]

Dinitramine's mode of action is inhibition of microtubule assembly, so its HRAC classification is Group D (Australia), Group K1 (global) or Group 3 (numeric).^[9]

Environmental effects

Dinitramine's soil-halflife varies dramatically with temperature, taking 31 to 47 weeks at 10 °C, but only 3.2-2.3 weeks at 30-40 °C.^[10] In a 1977 greenhouse trial, its halflife was only 1.2 months, the least persistent of any dinitroaninile.^[7]

Dinitramine accumulates in fish's flesh at up to 20 times its water concentration, though it is metabolised with a half life under 24 hours. It is toxic to fish at concentrations of 0.590-1.52 mg/L.^[6] Zebrafish embryos suffer developmental malformations under as little as 1.6 mg/L of dinitramine exposure.^[4]

Lists

Dinitramine has been marketed to control these weeds: Barnyardgrass, Florica pusley, Pigweed, Brachiaria, Foxtail species, carelessweed, carpetweed, Goosegrass, Purslane, Crabgrass, Johnsongrass, Texas panicum, Fall panicum, Smartweed, Black nightshade, Junglerice, Lambsquarters, kochia, Annual morningglory, Teaweed, Velvetleaf, Annual ragweed and hairy nightshade.^[3]