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Dicamba information


Dicamba[1]
Names
Preferred IUPAC name
3,6-Dichloro-2-methoxybenzoic acid
Other names
3,6-Dichloro-o-anisic acid
Dianat
Identifiers
CAS Number
  • 1918-00-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:81856 checkY
ChEMBL
  • ChEMBL476936 checkY
ChemSpider
  • 2922 checkY
ECHA InfoCard 100.016.033 Edit this at Wikidata
KEGG
  • C18597 checkY
PubChem CID
  • 3030
UNII
  • SJG3M6RY6H checkY
CompTox Dashboard (EPA)
  • DTXSID4024018 Edit this at Wikidata
InChI
  • InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12) checkY
    Key: IWEDIXLBFLAXBO-UHFFFAOYSA-N checkY
  • 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
"low"[2]
Solubility in acetone 810 g/L
Solubility in ethanol 922 g/L
Hazards
GHS labelling:[3]
Pictograms
GHS05: CorrosiveGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H318, H412
Precautionary statements
P273, P280, P305+P351+P338
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).
Infobox references

Dicamba (3,6-dichloro-2-methoxybenzoic acid) is a selective systemic herbicide first registered in 1967.[4] Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid.[5] It has been described as a "widely used, low-cost, environmentally friendly herbicide that does not persist in soils and shows little or no toxicity to wildlife and humans."[6]

Despite its success in improving crop yields, dicamba has attracted controversy. According to the United States Environmental Protection Agency (EPA), dicamba's primary ecological risk is for non-target terrestrial plants from exposure through spray drift, whereby dicamba inadvertently migrates to non-targeted neighboring areas, damaging those plants.[7][8]

In 2016, dicamba was approved for use in the United States over GMO dicamba-resistant crops created by Monsanto. Dicamba came under significant scrutiny due to its tendency to spread from treated fields into neighboring fields, causing damage.[9] The controversy led to litigation, state bans and additional restrictions over dicamba use.

  1. ^ Merck Index, 11th Edition, 3026.
  2. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  3. ^ Record of Dicamba in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2023-12-12.
  4. ^ "Reregistration Eligibility Decision for Dicamba and Associated Salts - US EPA" (PDF). 8 June 2006.
  5. ^ "Dicamba (Banvel) Herbicide Profile 10/83, Pesticide Management Education Program". Cornell University.
  6. ^ Cite error: The named reference Weeks was invoked but never defined (see the help page).
  7. ^ "Dicamba". United States Environmental Protection Agency. 16 February 2023.
  8. ^ "Dicamba". United States Environmental Protection Agency. 16 February 2023. Archived from the original on 23 December 2023.
  9. ^ Revealed: Monsanto predicted crop system would damage US farms The Guardian, 2020

and 27 Related for: Dicamba information

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Dicamba

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Dicamba (3,6-dichloro-2-methoxybenzoic acid) is a selective systemic herbicide first registered in 1967. Brand names for formulations of this herbicide...

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Pesticide drift

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treatment of Dicamba with amines, which form ammonium salts. These salts are described by their acronyms BAPMA-Dicamba and DGA-Dicamba. Although these...

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BASF

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lawsuit concerning Dicamba-related products began in Cape Girardeau, Missouri. The lawsuit involves a peach farmer who alleged that Dicamba-based herbicides...

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Erigeron canadensis

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glyphosate and other herbicides. Farmers are advised to include 2,4-D or dicamba in a burndown application prior to planting to control horseweed. The Zuni...

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Monsanto

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settlements in lawsuits involving ex-Monsanto products Roundup, PCBs and Dicamba. Owing to the massive financial and reputational blows caused by ongoing...

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Bayer

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destruction of his peach trees which was caused by the usage of dicamba by nearby farmers. Dicamba was another product which Bayer acquired from Monsanto. Bayer...

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Herbicide

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of the herbicide is of primary affecting efficacy. 2,4-D, mecoprop, and dicamba control many broadleaf weeds but remain ineffective against turf grasses...

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Monsanto legal cases

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litigation related to ex-Monsanto products such as glyphosate, PCBs and dicamba. In 2020 it paid over $10 billion to settle lawsuits involving the glyphosate...

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Demethylation

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Wen Zhi; Weeks, Donald P.; Wilson, Mark A. (2009). "Crystal Structure of Dicamba Monooxygenase: A Rieske Nonheme Oxygenase that Catalyzes Oxidative Demethylation"...

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Mecoprop

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in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA, which mimic the plant hormone IAA (auxin) and kill most broadleaf...

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Soliva sessilis

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germinate. Effective herbicides are typically combinations of MCPA and Dicamba, which target broad-leaved plants but not grasses. These chemicals have...

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Dichlorosalicylic acid

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herbicide dicamba. Chlorosalicylic acid Dumitru, Razvan; Jiang, Wen Zhi; Weeks, Donald P.; Wilson, Mark A. (2009). "Crystal Structure of Dicamba Monooxygenase:...

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Tribulus terrestris

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and dicamba are effective on T. terrestris. Like most postemergents, they are more effectively maintained when caught small and young. Dicamba and 2...

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Amaranthus palmeri

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documented a population of Palmer amaranth with resistance to 2,4-D and Dicamba in Kansas. Previously, Palmer amaranth in Kansas has developed resistance...

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Auxin

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compounds with auxinic activity. Synthetic auxins fall into four classes: dicamba quinolinecarboxylic acids, which includes quinclorac derivatives of pyridinecarboxylic...

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Phenoxy herbicide

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Agricultural Use for Dicamba, 2019". Retrieved 2021-12-27. Gray, Bryce (2016-11-09). "EPA approves Monsanto's less-volatile form of dicamba herbicide". St....

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Centaurea calcitrapa

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aminopyralid, chlorsulfuron, clopyralid, clopyralid + 2,4-D, dicamba, diflufenzopyr + dicamba, picloram, and triclopyr + clopyralid for the Pacific Northwest...

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Onopordum acanthium

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Therefore, several years of re-treatment may be necessary. Picloram, dicamba, 2,4-D, dicamba + 2,4,-D, and metsulfuron are effective for controlling cotton...

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Genetically modified crops

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occurred from dicamba formulations intended to reduce volatilization drifting when sprayed on resistant soybeans in 2017. The newer dicamba formulation...

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Gila National Forest

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allowing 21 herbicides within the forest, including dicamba, picloram and aminocyclopyrachlor (ACP). Dicamba is a threat to monarch butterfly habitat. ACP is...

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Brunnichia

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closing production due to damage to native wildflowers from the herbicide Dicamba, and possibly relocating to Mississippi. Redvine was specifically cited...

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Convolvulus arvensis

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glyphosate. Other herbicides usually recommended for this species are 2,4-D, dicamba, picloram, quinclorac and paraquat. In one of the tales collected by Jacob...

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Centaurea iberica

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clopyralid, clopyralid + 2,4-Dichlorophenoxyacetic acid, dicamba, diflufenzopyr + dicamba, picloram, and triclopyr + clopyralid for the Pacific Northwest...

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Centaurea solstitialis

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for post-emergence control, including 2,4-D, aminopyralid, clopyralid, dicamba, picloram and triclopyr. In California, aminopyralid, which has both post-...

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American Soybean Association

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yields and nutrition qualities. Representing both users of dicamba and some of the victims of dicamba drift - and recognizing that one important invisible asset...

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List of genetically modified crops

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engineered to be resistant to the herbicides 2,4-dichlorophenoxyacetic acid, dicamba, glufosinate glyphosate, sulfonylurea, oxynil mesotrione and isoxaflutole...

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Euphorbia myrsinites

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spurge can be effectively controlled with products containing 2, 4-D and dicamba (i.e. Weed B Gon) applied in late fall. Biological control There are currently...

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