Dicamba

Dicamba

Names
IUPAC name 3,6-Dichloro-2-methoxybenzoic acid
Other names 3,6-Dichloro-o-anisic acid Dianat
Identifiers
CAS Number	1918-00-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:81856 N
ChEMBL	ChEMBL476936 Y
ChemSpider	2922 Y
ECHA InfoCard	100.016.033
KEGG	C18597 N
PubChem	10433671
UNII	SJG3M6RY6H Y
InChI InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12) Y Key: IWEDIXLBFLAXBO-UHFFFAOYSA-N Y InChI=1/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12) Key: IWEDIXLBFLAXBO-UHFFFAOYAV
SMILES Clc1ccc(Cl)c(c1OC)C(=O)O
Properties
Chemical formula	C8H6Cl2O3
Molar mass	221.03 g·mol−1
Appearance	White crystalline solid
Density	1.57
Melting point	114 to 116 °C (237 to 241 °F; 387 to 389 K)
Solubility in water	500 g/L
Solubility in acetone	810 g/L
Solubility in ethanol	922 g/L
Hazards
Flash point	199 °C (390 °F; 472 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Dicamba (3,6-dichloro-2-methoxybenzoic acid) is a broad-spectrum herbicide. Brand names for formulations of this herbicide include Banvel, Diablo, Oracle and Vanquish. This chemical compound is an organochloride and a derivative of benzoic acid.

Dicamba controls annual and perennial rose weeds in grain crops and highlands, and it is used to control brush and bracken in pastures, as well as legumes and cacti. It kills broadleaf weeds before and after they sprout. In combination with a phenoxy herbicide or with other herbicides, dicamba is used in pastures, range land, and noncrop areas (fence rows, roadways, and wastage) to control weeds. Dicamba is toxic to conifer species but is in general less toxic to grasses.

Dicamba functions by increasing plant growth rate. At sufficient concentrations, the plant outgrows its nutrient supplies and dies.

The growth regulating properties of dicamba were first discovered by Zimmerman and Hitchcock in 1942. Soon after Jealott's Hill Experimental Station in England was evaluating dicamba in the field. Dicamba has since been used for household and commercial weed control.

Increasing use of dicamba has been reported with the release of dicamba resistant genetically modified plants by Monsanto. In October 2016, the EPA launched a criminal investigation into the illegal application of older, drift prone formulations of dicamba onto these new plant. Older formulations have been reported to drift after application and affect other crops not meant to be treated. New formulations of dicamba designed to be less airborne and inhibit unintended drift between fields are currently under review for EPA approval in the United States.

Some weed species have developed resistance to dicamba. Dicamba resistance in Bassia scoparia was discovered in 1994 and has not been explained by common modes of resistance such as absorption, translocation, or metabolism.