Dicamba

Dicamba[1]
Names
Preferred IUPAC name
3,6-Dichloro-2-methoxybenzoic acid
Other names
3,6-Dichloro-o-anisic acid
Dianat
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.033
KEGG
UNII
  • 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
  • Clc1ccc(Cl)c(c1OC)C(=O)O
Properties
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)
500 g/L
Solubility in acetone 810 g/L
Solubility in ethanol 922 g/L
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
H302, H318, H412
P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P501
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 broad-spectrum herbicide first registered in 1967.[2] 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.[3]

Around 2016, dicamba's use came under significant scrutiny due to its tendency to spread from treated fields into neighboring fields, causing damage.[4]

Use as an herbicide

Dicamba kills annual and perennial broadleaf weeds. Its primary commercial applications are weed control for grain crops and turf areas. It is also used to control brush and bracken in pastures, as well as controlling legumes and cacti. In combination with a phenoxy herbicide or with other herbicides, dicamba can be used for weed control in range land and other noncrop areas (fence rows, roadways, and wastage). Dicamba is toxic to conifer species but is in general less toxic to grasses.[5]

Dicamba is a synthetic auxin that functions by increasing plant growth rate, leading to senescence and cell death.[5][6]

The growth regulating properties of dicamba were first discovered by Zimmerman and Hitchcock in 1942.[7] 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 plants.[8][9] Older formulations have been reported to drift after application and affect other crops not meant to be treated.[10][11] A less volatile formulation of dicamba made by Monsanto, designed to be less prone to vaporizing and inhibit unintended drift between fields, was approved for use in the United States by the EPA in 2016, and was commercially available in 2017.[12] As a result, the use of dicamba in US agriculture rose sharply from approximately 8,000,000 pounds (3,600,000 kg) in 2016 to 30,000,000 pounds (14,000,000 kg) in 2019, according to the US Geological Survey.[13]

Resistance

Some farmers and researchers have expressed concern about herbicide resistance after the introduction of resistant crops.[14][15] In the laboratory, researchers have demonstrated weed resistance to dicamba within three generations of exposure.[14] Similar herbicide resistant weeds arose after the introduction of glyphosate-resistant crops (marketed as 'Roundup Ready').[14][15][16][17] Some weed species, like Amaranthus palmeri, 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.[18]

Genetically modified crops

The soil bacterium Pseudomonas maltophilia (strain DI-6) converts dicamba to 3,6-dichlorosalicylic acid (3,6-DCSA), which is adsorbed to soil much more strongly than is dicamba, but lacks herbicidal activity. Little information is available on the toxicity of this breakdown intermediate. The enzymes responsible for this first breakdown step comprise a three-component system called dicamba O-demethylase.

Monsanto recently incorporated one component of the three enzymes into the genome of soybean, cotton, and other broadleaf crop plants, making them resistant to dicamba.[19] Monsanto has marketed their dicamba resistant crops under the brand name Xtend.[14]

Farmers have expressed concern about being forced to grow resistant crops as protection against drifting dicamba.[14]

Volatilization

Dicamba came under scrutiny due to its tendency to vaporize from treated fields and spread to neighboring crops.[20] Monsanto began offering crops resistant to dicamba before a reformulated and drift resistant herbicide, which they claimed would be less likely to affect neighboring fields, had gained approval from the Environmental Protection Agency. Incidents in which dicamba affected neighboring fields led to complaints from farmers and fines in some US states.[21][upper-alpha 1] A lower volatility formulation, M1768, was approved by the EPA in November 2016.[22] However, this formulation has not been evaluated by experts outside of Monsanto.[23]

Dicamba formulations, including those registered in the late 2010s, can be especially prone to volatility, temperature inversions near ground level, and drift.[24]

Toxicological effects

Dicamba does not present unusual handling hazards.[25]

Humans

Increased cancer rate ratios and positive exposure–response patterns were reported (among other Canada/US-registered pesticides) for dicamba, in a review of data gathered in the National Institutes of Health's Agricultural Health Study.[26] In addition, the risk of non-Hodgkins lymphoma in men was statistically significantly increased by exposure to dicamba, in the Cross-Canada Study of Pesticides and Health.[27]

Mammals

It is moderately toxic by ingestion and slightly toxic by inhalation or dermal exposure (oral LD50 in rats: 757 mg/kg body weight, dermal LD50 in rats: >2,000 mg/kg, inhalation LC50 in rats: >200 mg/L). In a three-generation study, dicamba did not affect the reproductive capacity of rats.[28]

When rabbits were given doses of 0, 0.5, 1, 3, 10, or 20 (mg/kg)/day of technical dicamba from days 6 through 18 of pregnancy, toxic effects on the mothers, slightly reduced fetal body weights, and increased loss of fetuses occurred at the 10 mg/kg dose. U.S. Environmental Protection Agency (EPA) has set the NOAEL for this study at 3 (mg/kg)/day.[28]

In dog tests, some enlargement of liver cells has occurred, but a similar effect has not been shown in humans.[28]

Aquatic animals

Dicamba was tested for acute toxicity in a variety of aquatic animals. The studies accepted by the U.S. EPA found dicamba acid and DMA salt to be practically nontoxic to aquatic invertebrates. Studies accepted by the U.S. EPA found dicamba acid to be slightly toxic to cold water fish (rainbow trout), and practically nontoxic to warm water fish. Recent studies suggest that dicamba should be considered to be a potential endocrine disruptor for fish at environmentally relevant concentrations.[29]

Environmental fate

Soil

Dicamba is released directly to the environment by its application as an herbicide for the control of annual broadleaf weeds. It may cause damage to plants as a result of its absorption from the soil by plant roots. Dicamba is mobile in most soils and significant leaching is possible. The adsorption of dicamba to organo-clay soil is influenced by soil pH with the greatest adsorption to soil occurring in acidic soils. Dicamba is moderately persistent in soil. Its reported half-life in soil ranges from 1 to 6 weeks. Dicamba is likely to be more rapidly degraded in soils with high microbial populations, but dissipates more slowly in hardwood forests and wetlands than would be expected from the results of laboratory studies.

At a level of 10 mg/kg in sandy loam soil, dicamba caused a transient decrease in nitrification after two but not three weeks of incubation. The investigator determined that the decrease in nitrification is not substantial and does not suggest the potential for a prolonged impact on microbial activity. In the same study, dicamba did not affect ammonia formation or sulfur oxidation. In a more recent laboratory study, dicamba, at a concentration of 1 mg/kg soil, did not affect urea hydrolysis or nitrification in four soil types.

Water

Dicamba salts used in some herbicides are highly soluble in water. A recent study conducted from 1991 to 1996 by the U.S. Geologic Survey found dicamba in 0.13% of the ground waters surveyed. The maximum level detected was 0.0021 mg/L.[30] The prevalence of dicamba in groundwater from agricultural areas (0.11%) did not correlate with nonagricultural urban areas (0.35%).

Legality

Arkansas and Missouri banned the sale and use of dicamba in July 2017 in response to complaints of crop damage due to drift.[31] Monsanto responded by arguing that not all instances of crop damage had been investigated and a ban was premature.[32] Monsanto sued the state of Arkansas to stop the ban, but the case was dismissed in February 2018.[33] It has also been acknowledged that the use of dicamba had increased since 2017.[34][35] Complaints against dicamba accelerated after the EPA approved a Monsanto-created soybean which could tolerate it in 2016.[36] The soybean was a part of Monsanto's Xtend products.[36]

In June 2020, the 9th U.S. Circuit Court of Appeals blocked sales of three dicamba-based herbicides in the United States, finding that the Environmental Protection Agency understated risks of spraying.[37][38] On 8 June 2020, the EPA clarified that existing stocks of the dicamba-based pesticides bought before 3 June 2020 may be used according to their previous labels until 31 July 2020.[39] In October 2020 the EPA issued a decision on the registration application of three dicamba-based products, Xtendimax, Engenia, and Tavium. They approved of their use from 2021 to 2025 with some additional changes, including labeling restrictions.[40]

Lawsuits

In February 2018, it was reported that numerous farmers from 21 states had filed lawsuits against Monsanto alleging that dicamba damaged their crops, with the most prominent cases coming from Missouri and Arkansas.[41] By August 2019, more lawsuits were filed, alleging that dicamba had damaged crops, gardens, and trees of neighbors of the farmers who used it.[34][35]

On 27 January 2020, the first trial concerning dicamba-related products began in Cape Girardeau, Missouri.[42][43] The lawsuit involves a peach farmer who alleged that dicamba-based herbicides caused significant damage to his crops and trees.[44] It had also been filed in November 2016, when dicamba was still owned by Monsanto.[45][46][47] On 14 February 2020, the jury involved in the lawsuit ruled against dicamba owner Bayer and its co-defendant BASF and found in favor of the peach grower, Bader Farms owner Bill Bader.[48] Bayer and BASF were also ordered to pay Bader $15 million in damages.[49] On 15 February 2020, Monsanto and BASF were ordered to pay an additional $250 million in punitive damages.[50][51] Court documents revealed Monsanto had used dicamba drift as a sales pitch to convince farmers to buy their proprietary dicamba-resistant seeds or face devastated crops.[52]

On 17 February, it was announced that dicamba would face many more lawsuits.[53] On 26 February, the Peiffer Wolf Carr & Kane Law Firm announced that after the Bader verdict, more than 2,000 U.S. farmers hired the law firm to represent them in upcoming lawsuits.[54]

In June 2020, Bayer agreed to a settlement of up to $400 million for all 2015-2020 crop year dicamba claims, not including the $250 million judgement.[55] On 25 November 2020, U.S. District Judge Stephen Limbaugh Jr. reduced the punitive damage amount in the Bader Farms case to $60 million.[56]

References

Notes
  1. According to an article by NPR, this may force farmers into buying dicamba resistant seeds from Monsanto, as they have been adversely affected. Moreover, there is some risk that pigweed will become resistant to the product, thereby forcing farmers to get into other crops.[14][15]

Citations
  1. Merck Index, 11th Edition, 3026.
  2. "Reregistration Eligibility Decision for Dicamba and Associated Salts - US EPA" (PDF). 8 June 2006.
  3. "Dicamba (Banvel) Herbicide Profile 10/83, Pesticide Management Education Program". Cornell University.
  4. Revealed: Monsanto predicted crop system would damage US farms The Guardian, 2020
  5. Arnold P. Appleby, Franz Müller. "Weed Control, 2" in Ullmann's Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.o28_o01
  6. Gleason, Cynthia; Foley, Rhonda C.; Singh, Karam B. (2011). "Mutant Analysis in Arabidopsis Provides Insight into the Molecular Mode of Action of the Auxinic Herbicide Dicamba". PLOS ONE. 6 (3): e17245. Bibcode:2011PLoSO...617245G. doi:10.1371/journal.pone.0017245. PMC 3050828. PMID 21408147.
  7. Peterson, Gale E. (1967). "The Discovery and Development of 2,4-D". Agricultural History. Agricultural History Society. 41 (3): 243–254. JSTOR 3740338. Retrieved 10 November 2020.
  8. Weinraub, Mark (25 October 2016). "U.S. agency searches for proof of criminal use of herbicide dicamba". Reuters. Retrieved 29 October 2016.
  9. "EPA Probes Dicamba Use- Federal Search Warrants Issued in Missouri". KTIC Radio. 25 October 2016. Retrieved 4 October 2017.
  10. Gray, Bryce (5 August 2016). "Suspected illegal herbicide use takes toll on southeast Missouri farmers". St Louis Post-Dispatch. Retrieved 16 August 2016.
  11. Gray, Bryce (14 August 2016). "Illegal herbicide use may threaten survival of Missouri's largest peach farm". St Louis Post-Dispatch. Retrieved 16 August 2016.
  12. Gray, Bryce (9 November 2016). "EPA approves Monsanto's less-volatile form of dicamba herbicide". St. Louis Post-Dispatch. Retrieved 24 June 2017.
  13. US Geological Survey (12 October 2021). "Estimated Agricultural Use for Dicamba, 2019". Retrieved 27 December 2021.
  14. Charles, Dan (1 August 2016). "Crime in the Fields: How Monsanto And Scofflaw Farmers Hurt Soybeans in Arkansas". NPR. Retrieved 1 August 2016.
  15. "Business: Monsanto's Superweeds Saga Is Only Getting Worse". Yahoo, TakePart.com. 2 August 2016. Retrieved 3 August 2016.
  16. The Rise of Superweeds scientificamerican.com
  17. Dewey, Caitlin (29 August 2017). "This miracle weed killer was supposed to save farms. Instead, it's devastating them". The Washington Post. Retrieved 30 August 2017.
  18. Cranston, Harwood J.; Kern, Anthony J.; Hackett, Josette L.; Miller, Erica K.; Maxwell, Bruce D.; Dyer, William E. (2001). "Dicamba resistance in kochia". Weed Science. 49 (2): 164. doi:10.1614/0043-1745(2001)049[0164:DRIK]2.0.CO;2.
  19. Behrens, M. R.; Mutlu, N.; Chakraborty, S.; Dumitru, R.; Jiang, W. Z.; Lavallee, B. J.; Herman, P. L.; Clemente, T. E.; Weeks, D. P. (2007). "Dicamba Resistance: Enlarging and Preserving Biotechnology-Based Weed Management Strategies". Science. 316 (5828): 1185–8. Bibcode:2007Sci...316.1185B. doi:10.1126/science.1141596. PMID 17525337. S2CID 7093076.
  20. Pollack, Andrew (25 April 2012). "Dow Corn, Resistant to a Weed Killer, Runs into Opposition". The New York Times. Retrieved 1 August 2016.
  21. Tatge, Jason (9 November 2017). "Protecting Your Business with Ag Data: What Dicamba Can Teach Us (Guest Column) | PrecisionAg". PrecisionAg. Retrieved 12 November 2017.
  22. Final Registration of Dicamba on Dicamba-Tolerant Cotton and Soybean, 9 November 2016
  23. "Scant oversight, corporate secrecy preceded U.S. weed killer crisis". Reuters. 9 August 2017.
  24. "Dicamba Know-How: Seven Things to Know Before You Spray Dicamba in 2020". Progressive Farmer. Retrieved 10 July 2020.
  25. "dicamba (Banvel) Herbicide Profile 10/83". Cornell University. 17 October 1983. Archived from the original on 27 September 2011. Retrieved 16 May 2023.
  26. A Review of Pesticide Exposure and Cancer Incidence in the Agricultural Health Study Cohort
  27. McDuffie, Helen H.; Pahwa, Punam; McLaughlin, John R.; Spinelli, John J.; Fincham, Shirley; Dosman, James A.; Robson, Diane; Skinnider, Leo F.; Choi, Norman W. (November 2001). "Non-Hodgkin's Lymphoma and Specific Pesticide Exposures in Men". Cancer Epidemiology, Biomarkers & Prevention. 10 (11). Retrieved 13 April 2021.
  28. Pesticide Information Profile – Dicamba, Pesticide Management Education Program, Cornell University.
  29. Zhu, L; Li, W; Zha, J; Wang, Z (2015). "Dicamba affects sex steroid hormone level and mRNA expression of related genes in adult rare minnow (Gobiocypris rarus) at environmentally relevant concentrations". Environmental Toxicology. 30 (6): 693–703. Bibcode:2015EnTox..30..693Z. doi:10.1002/tox.21947. PMID 24420721. S2CID 45373092.
  30. Kolpin, D. W., J. E. Barbash, and R. J. Gilliom. 2000. Pesticides in Ground Water of the United States, 1992–1996. Groundwater 38:858–863.
  31. Gray, Bryce (7 July 2017). "Missouri and Arkansas ban dicamba herbicide as complaints snowball". St. Louis Post-Dispatch. Retrieved 10 July 2017.
  32. Pucci, Jackie (10 July 2017). "Monsanto Responds to Arkansas, Missouri Dicamba Bans". Crop Life. Retrieved 10 July 2017.
  33. Nosowitz, Dan (20 February 2018). "Monsanto's Lawsuit Against Arkansas for Dicamba Ban Dismissed". Modern Farmer. Retrieved 7 March 2018.
  34. "Despite Federal, State Efforts, Dicamba Complaints Continue". Illinois Public Media. 31 August 2019.
  35. "Farmers, Conservationists Challenge Approval of Monsanto's Crop-damaging Dicamba Pesticide". Center for Biological Diversity.
  36. "Dicamba Lawsuit | Crop Damage Compensation for Farmers". ConsumerNotice.org.
  37. "U.S. Court Blocks Sales of Bayer Weed Killer in United States". Reuters. 4 June 2020. Retrieved 11 June 2020.
  38. US EPA, OCSPP (8 June 2020). "Final Cancellation Order for Three Dicamba Products". US EPA. Retrieved 11 June 2020.
  39. "EPA Offers Clarity to Farmers in Light of Recent Court Vacatur of Dicamba Registrations". EPA. 8 June 2020. Retrieved 11 June 2020.
  40. "EPA Approves Dicamba Pesticides Through 2025; Additional Restrictions Imposed". Texas Agricultural Extension. 9 November 2020. Retrieved 26 May 2021.
  41. "Dicamba Damage Lawsuit - Monsanto Herbicide Lawyers". ClassAction.com.
  42. Ruff, Corinne (28 January 2020). "Dicamba-Related Federal Trial Begins in Southeast Missouri". news.stlpublicradio.org.
  43. "Bayer/BASF-Dicamba Lawsuit | KDUZ".
  44. Reporting, Johnathan Hettinger Midwest Center for Investigative. "Monsanto's defense: Fungal disease, not dicamba, to blame for peach farmer's problems". stltoday.com.
  45. Reporting, Johnathan Hettinger Midwest Center for Investigative. "Dicamba on trial: Monsanto officials limited testing on their own plots". stltoday.com.
  46. Ruff, Corinne (24 January 2020). "Dicamba Goes on Trial: The History Behind Monsanto's Friendship-Wilting Weed Killer". news.stlpublicradio.org.
  47. Reporting, Johnathan Hettinger Midwest Center for Investigative. "Peach farmer takes stand in lawsuit against Bayer, BASF". stltoday.com.
  48. Gray, Bryce. "Jury finds in favor of Missouri peach grower in lawsuit against Bayer, BASF". stltoday.com.
  49. "Bayer's Dicamba Hit Tests Patience of Frustrated Investors". Bloomberg.com. 14 February 2020.
  50. Ruff, Corinne (15 February 2020). "Monsanto, BASF Will Pay $250 Million in Punitive Damages in First Dicamba Trial". news.stlpublicradio.org.
  51. "Missouri Farm Awarded $265M in Suit Against BASF and Bayer". The New York Times. Associated Press. 15 February 2020.
  52. McGlashen, Andy (Winter 2022). "Bitter Harvest". Audubon. New York, NY: Audubon Society: 45. ISSN 0004-7694. OCLC 6823366.
  53. Feeley, Jef; Bross, Tim; Bloomberg (17 February 2020). "Bayer is facing a new wave of herbicide lawsuits—and this time it's not over Monsanto's Roundup". fortune.com. Retrieved 17 December 2020.
  54. "More Than 2,000 Farmer Are Expected To File Dicamba-Damage Lawsuits, Says Law Firm". Successful Farming. 26 February 2020. Retrieved 11 March 2020.
  55. Bayer To Pay More Than $10 Billion To Resolve Cancer Lawsuits Over Weedkiller Roundup
  56. Reeves, J.C. (15 December 2020). "District Judge orders reduction of punitive damages in dicamba case". Southeast Missourian. Retrieved 15 December 2020.
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