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Dicamba

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285: 190: 502: 497: 669: 918: 29: 975:"substantially understated risks that it acknowledged and failed entirely to acknowledge other risks." The EPA's Office of the Inspector General concluded that the EPA had deviated from typical procedures in its 2018 decision despite the best efforts of EPA's career scientists and managers to recommend a different approach that was scientifically, procedurally, and legally sound. 728:
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. 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
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Complaints against dicamba accelerated after the United States EPA approved a Monsanto-created soybean which could tolerate it in 2016. The soybean was a part of Monsanto's Xtend products. Dicamba was approved by the EPA for "over-the-top" (OTT) use on those dicamba-tolerant soybean and cotton crops.
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launched a criminal investigation into the illegal application of older, drift prone formulations of dicamba onto these new plants. Older formulations have been reported to drift after application and affect other crops not meant to be treated. A less volatile formulation of dicamba made by Monsanto,
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banned the sale and use of dicamba in July 2017 in response to complaints of crop damage due to drift. Monsanto responded by arguing that not all instances of crop damage had been investigated and a ban was premature. Monsanto sued the state of Arkansas to stop the ban, but the case was dismissed in
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On 27 January 2020, the first trial concerning dicamba-related products began in Cape Girardeau, Missouri. The lawsuit involves a peach farmer who alleged that dicamba-based herbicides caused significant damage to his crops and trees. It had also been filed in November 2016, when dicamba was still
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Despite the control measures implemented by the EPA in 2020, the 2021 incident reports showed little change in the number, severity, and/or geographic extent of dicamba-related incidents. In March 2022 and in February 2023, EPA approved additional labeling to further restrict use of OTT dicamba to
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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. In October 2020 the EPA issued a decision on the registration application of three dicamba-based products, Xtendimax,
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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. By August 2019, more lawsuits were filed, alleging that dicamba had damaged crops,
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On 17 February, it was announced that dicamba would face many more lawsuits. 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.
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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.
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identified spray drift as the primary ecological risk for dicamba due to its potential effects on non-target terrestrial plants. Dicamba is also available in a drift-resistant formulation, which is less likely to affect neighboring fields.
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and found in favor of the peach grower, Bader Farms owner Bill Bader. Bayer and BASF were also ordered to pay Bader $ 15 million in damages. On 15 February 2020, Monsanto and BASF were ordered to pay an additional $ 250 million in
660:. Dicamba came under significant scrutiny due to its tendency to spread from treated fields into neighboring fields, causing damage. The controversy led to litigation, state bans and additional restrictions over dicamba use. 853:(strain DI-6) converts dicamba to 3,6-dichlorosalicylic acid (3,6-DCSA), which lacks herbicidal activity. The enzymes responsible for this first breakdown step comprise a three-component system called dicamba O-demethylase. 1088: 676:
Dicamba is a selective and systemic herbicide that 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
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reduce the likelihood of volatility and offsite movement of OTT dicamba by avoiding application on days with high temperatures. The restriction apply to Minnesota, Iowa, Illinois, Indiana, and South Dakota.
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to handlers mixing and loading dry flowable formulations for application to sod and field crops. The Agency did not identify dietary, residential, aggregate, or post-application risks of concern.
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In 2017 and again in 2018, EPA amended the registrations of all OTT dicamba products following reports that farmers had experienced crop damage and economic losses resulting from spray drifting.
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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. On 25 November 2020, U.S. District Judge
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is a common concern with herbicide. In the laboratory, researchers have demonstrated weed resistance to dicamba within three generations of exposure. This effect is illustrated by
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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).
638:. 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." 1795: 1005:. 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. 560: 1732:"Dicamba affects sex steroid hormone level and mRNA expression of related genes in adult rare minnow (Gobiocypris rarus) at environmentally relevant concentrations" 2010:
Krueger, James P.; Butz, Robert G.; Atallah, Yousef H.; Cork, Douglas J. (1989). "Isolation and identification of microorganisms for the degradation of Dicamba".
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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
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Cranston, Harwood J.; Kern, Anthony J.; Hackett, Josette L.; Miller, Erica K.; Maxwell, Bruce D.; Dyer, William E. (2001). "Dicamba resistance in kochia".
2921: 2409: 940:, which hydroxylates the methyl group of dicamba. The hydroxymethylated derivative hydrolyzes readily to an inactive dichlorosalicylic acid or its 827:
Dicamba and its derivatives are practically nontoxic to aquatic invertebrates. Studies suggest that dicamba should be considered to be a potential
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Increased lung and colon cancer rate ratios and positive exposure–response patterns were reported for dicamba, in a review of data gathered in the
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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).
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Dicamba use in the US in 2019. Usage has substantially increased since dicamba was approved for use over dicamba-resistant GMO crops in 2016.
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Milligan, Peter W.; Häggblom, Max M. (1 April 1999). "Biodegradation and Biotransformation of Dicamba under Different Reducing Conditions".
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Kolpin, Dana W.; Barbash, Jack E.; Gilliom, Robert J. (November 2000). "Pesticides in Ground Water of the United States, 1992–1996".
777:'s Agricultural Health Study. The Cross-Canada Study of Pesticides and Health found that exposure to dicamba increased the risk of 839:
The 2022 EPA draft ecological risk assessment identified potential adverse effects to birds, and bee larvae for all dicamba uses.
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Engenia, and Tavium. They approved of their use from 2021 to 2025 with some additional changes, including labeling restrictions.
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owned by Monsanto. On 14 February 2020, the jury involved in the lawsuit ruled against dicamba owner Bayer and its co-defendant
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identified dicamba's potential for long-range transport through the atmosphere as a critical area of concern. In 2022, the
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in England was evaluating dicamba in the field. Dicamba has since been used for household and commercial weed control.
1716: 3599: 3061: 968: 299: 1295:"Mutant Analysis in Arabidopsis Provides Insight into the Molecular Mode of Action of the Auxinic Herbicide Dicamba" 1239: 804:
in rats: >200 mg/L). In a three-generation study, dicamba did not affect the reproductive capacity of rats.
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The growth regulating properties of dicamba were first discovered by Zimmerman and Hitchcock in 1942. Soon after,
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Farmers have expressed concern about being forced to grow resistant crops as protection against drifting dicamba.
585: 972: 724: 3026: 1963:"Crystal Structure of Dicamba Monooxygenase: A Rieske Nonheme Oxygenase that Catalyzes Oxidative Demethylation" 1358: 819:
In dog tests, some enlargement of liver cells has occurred, but a similar effect has not been shown in humans.
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found dicamba in 0.13% of the groundwaters surveyed. The maximum level detected was 0.0021 mg/L.
556: 3297: 3071: 2903: 1599:"Conclusion on the peer review of the pesticide risk assessment of the active substance dicamba | EFSA" 879: 501: 2558: 3635: 2961: 2642: 1393: 1084: 883: 649:, whereby dicamba inadvertently migrates to non-targeted neighboring areas, damaging those plants. 645:(EPA), dicamba's primary ecological risk is for non-target terrestrial plants from exposure through 3554: 2898: 2694: 641:
Despite its success in improving crop yields, dicamba has attracted controversy. According to the
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February 2018. It has also been acknowledged that the use of dicamba had increased since 2017.
3625: 3524: 1450: 933: 628: 496: 3630: 3476: 1633:"A Review of Pesticide Exposure and Cancer Incidence in the Agricultural Health Study Cohort" 1143:"Dicamba Resistance: Enlarging and Preserving Biotechnology-Based Weed Management Strategies" 778: 524: 489: 2654: 2206:"Farmers, Conservationists Challenge Approval of Monsanto's Crop-damaging Dicamba Pesticide" 2054: 1935: 1743: 1306: 1154: 926: 875: 729: 716: 251: 41: 167: 83: 8: 3534: 3499: 2893: 2687: 2356: 2272:"EPA Offers Clarity to Farmers in Light of Recent Court Vacatur of Dicamba Registrations" 2091: 828: 73: 2058: 1939: 1747: 1673: 1310: 1275: 1158: 284: 189: 127: 3494: 2669: 2522: 2372:"Monsanto's defense: Fungal disease, not dicamba, to blame for peach farmer's problems" 1987: 1962: 1947: 1767: 1712: 1657: 1632: 1571: 1367: 1329: 1294: 1178: 971:
blocked sales of three dicamba-based herbicides in the United States, finding that the
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Bayer To Pay More Than $ 10 Billion To Resolve Cancer Lawsuits Over Weedkiller Roundup
1077: 3009: 2539: 2531: 2410:"Dicamba Goes on Trial: The History Behind Monsanto's Friendship-Wilting Weed Killer" 2070: 2027: 1992: 1759: 1598: 1334: 1170: 690: 2584:"More Than 2,000 Farmer Are Expected To File Dicamba-Damage Lawsuits, Says Law Firm" 1771: 2062: 2019: 1982: 1974: 1943: 1872: 1751: 1652: 1644: 1606: 1324: 1314: 1182: 1162: 1062: 1002: 433: 357: 2659: 2617: 2485:"Monsanto, BASF Will Pay $ 250 Million in Punitive Damages in First Dicamba Trial" 1796:"Crime in the Fields: How Monsanto And Scofflaw Farmers Hurt Soybeans in Arkansas" 1119:"Dicamba (Banvel) Herbicide Profile 10/83, Pesticide Management Education Program" 715:
Increasing use of dicamba has been reported with the release of dicamba-resistant
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first registered in 1967. Brand names for formulations of this herbicide include
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Dicamba is poorly soluble in water. A study conducted from 1991 to 1996 by the
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Dicamba has low toxicity by ingestion and inhalation or dermal exposure (oral
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reduced the punitive damage amount in the Bader Farms case to $ 60 million.
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Dumitru, Razvan; Jiang, Wen Zhi; Weeks, Donald P.; Wilson, Mark A. (2009).
1763: 1338: 1174: 1446:"Suspected illegal herbicide use takes toll on southeast Missouri farmers" 3466: 3461: 3219: 3201: 3181: 3171: 3163: 3088: 3036: 2989: 2824: 2814: 2784: 2749: 2391:"Dicamba on trial: Monsanto officials limited testing on their own plots" 1544:"Dicamba Know-How: Seven Things to Know Before You Spray Dicamba in 2020" 1249: 1196: 1033: 937: 646: 567: 2023: 1648: 3584: 3564: 3544: 3504: 3410: 3370: 3272: 3136: 3118: 3103: 2994: 2946: 2941: 2936: 2865: 2845: 2840: 2804: 2734: 1422: 1371: 702: 458: 444: 391: 308:
InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12)
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InChI=1/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12)
3574: 3549: 3529: 3365: 3287: 3267: 3186: 3113: 3108: 3093: 2974: 2969: 2754: 2714: 2618:"District Judge orders reduction of punitive damages in dicamba case" 1394:"U.S. agency searches for proof of criminal use of herbicide dicamba" 601: 2665:
Dicamba Pesticide Information Profile – Extension Toxicology Network
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Dicamba Technical Fact Sheet – National Pesticide Information Center
2111:"Missouri and Arkansas ban dicamba herbicide as complaints snowball" 1419:"EPA Probes Dicamba Use- Federal Search Warrants Issued in Missouri" 578:
Except where otherwise noted, data are given for materials in their
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incorporated one component of the three enzymes into the genome of
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Dicamba General Fact Sheet – National Pesticide Information Center
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Reporting, Johnathan Hettinger Midwest Center for Investigative.
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Reporting, Johnathan Hettinger Midwest Center for Investigative.
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Reporting, Johnathan Hettinger Midwest Center for Investigative.
1497:"EPA approves Monsanto's less-volatile form of dicamba herbicide" 1397: 861: 694: 682: 678: 462: 448: 412: 218: 1674:"Non-Hodgkin's Lymphoma and Specific Pesticide Exposures in Men" 932:
It is biodegraded by both aerobic and anaerobic bacteria to 3,6-
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In 2016, dicamba was approved for use in the United States over
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Weichenthal, Scott; Moase, Connie; Chan, Peter (August 2010).
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Revealed: Monsanto predicted crop system would damage US farms
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species but is in general less toxic to grasses. Dicamba is a
3314: 2503:"Missouri Farm Awarded $ 265M in Suit Against BASF and Bayer" 2185:"Despite Federal, State Efforts, Dicamba Complaints Continue" 2092:"Dicamba Lawsuit | Crop Damage Compensation for Farmers" 1829: 813: 686: 600:(3,6-dichloro-2-methoxybenzoic acid) is a selective systemic 118: 96: 2466:"Bayer's Dicamba Hit Tests Patience of Frustrated Investors" 2339:"Dicamba-Related Federal Trial Begins in Southeast Missouri" 1826:"Business: Monsanto's Superweeds Saga Is Only Getting Worse" 1567:"Dow Corn, Resistant to a Weed Killer, Runs into Opposition" 1293:
Gleason, Cynthia; Foley, Rhonda C.; Singh, Karam B. (2011).
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gardens, and trees of neighbors of the farmers who used it.
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that functions by increasing plant growth rate, leading to
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114 to 116 Â°C (237 to 241 Â°F; 387 to 389 K)
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10.1614/0043-1745(2001)049[0164:DRIK]2.0.CO;2
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from treated fields onto neighboring crops. In 2011, the
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is Group I (Aus), Group O (Global), Group 4 (numeric).
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Feeley, Jef; Bross, Tim; Bloomberg (17 February 2020).
1960: 534: 2134:"Monsanto Responds to Arkansas, Missouri Dicamba Bans" 2009: 1057:
Arnold P. Appleby, Franz MĂĽller. "Weed Control, 2" in
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developed resistance to dicamba already in the 1990s.
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Dicamba came under scrutiny due to its reputation for
2320:"Dicamba Damage Lawsuit - Monsanto Herbicide Lawyers" 2247:"Final Cancellation Order for Three Dicamba Products" 831:
for fish at environmentally relevant concentrations.
2556: 1925: 1630: 1520: 1703: 1701: 1699: 530: 2520:McGlashen, Andy (Winter 2022). "Bitter Harvest". 2086: 2084: 1292: 3612: 2044: 1678:Cancer Epidemiology, Biomarkers & Prevention 947: 230: 2675:EPA Dicamba Reregistration Eligibility Decision 1696: 82: 2200: 2198: 2081: 1624: 1523:"Estimated Agricultural Use for Dicamba, 2019" 1059:Ullmann's Encyclopedia of Industrial Chemistry 796:in rats: 757 mg/kg body weight, dermal LD 2695: 2179: 2177: 1665: 1345: 1245:United States Environmental Protection Agency 1202:United States Environmental Protection Agency 842: 750:United States Environmental Protection Agency 643:United States Environmental Protection Agency 2709: 1729: 1366:(3). Agricultural History Society: 243–254. 1089:Institute for Occupational Safety and Health 800:in rats: >2,000 mg/kg, inhalation LC 2195: 1891:"Australia Herbicide Classification Lookup" 2702: 2688: 2174: 2012:Journal of Agricultural and Food Chemistry 1711:. Pesticide Management Education Program, 1465: 1437: 283: 188: 166: 2670:Monsanto's Xtend Crop System Product Page 2519: 1986: 1709:"Pesticide Information Profile – Dicamba" 1656: 1328: 1318: 1053: 1051: 1049: 1047: 250: 2357:"Bayer/BASF-Dicamba Lawsuit | KDUZ" 2154: 1521:US Geological Survey (12 October 2021). 1391: 1354:"The Discovery and Development of 2,4-D" 1351: 916: 667: 1820: 1818: 1793: 1789: 1787: 1785: 1783: 1781: 1730:Zhu, L; Li, W; Zha, J; Wang, Z (2015). 1564: 1536: 1136: 1134: 1132: 279: 3613: 2615: 2586:. Successful Farming. 26 February 2020 2244: 2047:Environmental Science & Technology 1044: 663: 572:199 Â°C (390 Â°F; 472 K) 179: 2683: 2509:. Associated Press. 15 February 2020. 2426: 2388: 2369: 2131: 1913:Herbicide Resistance Action Committee 1901: 1895:Herbicide Resistance Action Committee 1234: 1232: 936:. This conversion is catalyzed by a 921:Pathway for biodegradation of dicamba 912: 766:In 2022 the EPA identified potential 311:Key: IWEDIXLBFLAXBO-UHFFFAOYSA-N 146: 126: 2482: 2407: 2336: 2108: 1815: 1778: 1494: 1471: 1443: 1268: 1230: 1228: 1226: 1224: 1222: 1220: 1218: 1216: 1214: 1212: 1129: 810:U.S. Environmental Protection Agency 681:in pastures, as well as controlling 710:Jealott's Hill Experimental Station 656:dicamba-resistant crops created by 321:Key: IWEDIXLBFLAXBO-UHFFFAOYAV 221: 205: 16:Chemical compound used as herbicide 13: 2483:Ruff, Corinne (15 February 2020). 2155:Nosowitz, Dan (20 February 2018). 1948:10.1111/j.1745-6584.2000.tb00684.x 1392:Weinraub, Mark (25 October 2016). 1248:. 16 February 2023. Archived from 822: 46:3,6-Dichloro-2-methoxybenzoic acid 14: 3652: 2643:Appendix E: Herbicide Information 2636: 2616:Reeves, J.C. (15 December 2020). 2408:Ruff, Corinne (24 January 2020). 2337:Ruff, Corinne (28 January 2020). 1637:Environmental Health Perspectives 1565:Pollack, Andrew (25 April 2012). 1256: 1209: 969:9th U.S. Circuit Court of Appeals 834: 816:for this study at 3 (mg/kg)/day. 2445: 1715:. September 1993. Archived from 500: 495: 375: 369: 27: 2609: 2598: 2576: 2550: 2513: 2495: 2476: 2458: 2439: 2420: 2401: 2382: 2363: 2349: 2330: 2312: 2286: 2264: 2238: 2216: 2210:Center for Biological Diversity 2148: 2125: 2102: 2038: 2003: 1954: 1919: 1883: 1856: 1844: 1723: 1591: 1558: 1514: 1495:Gray, Bryce (9 November 2016). 1488: 1411: 1385: 1286: 973:Environmental Protection Agency 886:-resistant crops (marketed as ' 624:. This chemical compound is a 582:(at 25 Â°C , 100 kPa). 2645:, US Department of Agriculture 2132:Pucci, Jackie (10 July 2017). 1794:Charles, Dan (1 August 2016). 1472:Gray, Bryce (14 August 2016). 1282:. University of Hertfordshire. 1189: 1111: 1071: 1026: 746:European Food Safety Authority 381: 363: 1: 2245:US EPA, OCSPP (8 June 2020). 1832:, TakePart.com. 2 August 2016 1444:Gray, Bryce (5 August 2016). 1280:Pesticide Properties DataBase 1019: 948:Use on dicamba-tolerant crops 870: 775:National Institutes of Health 756: 2298:Texas Agricultural Extension 1967:Journal of Molecular Biology 1320:10.1371/journal.pone.0017245 7: 2109:Gray, Bryce (7 July 2017). 1061:2011, Wiley-VCH, Weinheim. 986: 10: 3657: 1352:Peterson, Gale E. (1967). 1091:, accessed on 2023-12-12. 878:after the introduction of 843:Genetically modified crops 784: 3517: 3475: 3434:Photosystem II inhibitors 3432: 3423: 3348:Photosystem II inhibitors 3337: 3296: 3258: 3233: 3210: 3162: 3153: 3127: 3079: 3070: 3017: 3008: 2960: 2912: 2879: 2823: 2721: 2113:. St. Louis Post-Dispatch 1979:10.1016/j.jmb.2009.07.021 1276:"Dicamba (Ref: SAN 837H)" 1085:GESTIS Substance Database 761: 689:. In combination with a 576: 476: 471: 350: 330: 295: 66: 52: 40: 35: 26: 3307:Photosystem I inhibitors 1736:Environmental Toxicology 1611:10.2903/j.efsa.2011.1965 1476:. St Louis Post-Dispatch 1067:10.1002/14356007.o28_o01 735: 547:Precautionary statements 407:White crystalline solid 342:Clc1ccc(Cl)c(c1OC)C(=O)O 2489:news.stlpublicradio.org 2414:news.stlpublicradio.org 2343:news.stlpublicradio.org 1501:St. Louis Post-Dispatch 1167:10.1126/science.1141596 850:Pseudomonas maltophilia 723:. In October 2016, the 2620:. Southeast Missourian 2226:. Reuters. 4 June 2020 1853:scientificamerican.com 1851:The Rise of Superweeds 1451:St Louis Post-Dispatch 934:dichlorosalicylic acid 922: 673: 2189:Illinois Public Media 1719:on 27 September 2020. 938:dicamba monooxygenase 920: 890:'). The weed species 779:non-Hodgkins lymphoma 671: 1546:. Progressive Farmer 1359:Agricultural History 1252:on 23 December 2023. 1014:Stephen Limbaugh Jr. 927:U.S. Geologic Survey 876:Herbicide resistance 730:US Geological Survey 717:genetically modified 42:Preferred IUPAC name 3641:Systemic herbicides 3535:aminocyclopyrachlor 3500:sulfometuron methyl 2649:Chemical Fact Sheet 2472:. 14 February 2020. 2059:1999EnST...33.1224M 2024:10.1021/jf00086a057 1940:2000GrWat..38..858K 1748:2015EnTox..30..693Z 1649:10.1289/ehp.0901731 1605:. 14 January 2011. 1311:2011PLoSO...617245G 1205:. 16 February 2023. 1159:2007Sci...316.1185B 847:The soil bacterium 829:endocrine disruptor 664:Use as an herbicide 434:Solubility in water 399: g·mol 23: 3621:Auxinic herbicides 3495:metsulfuron-methyl 3164:Nitrophenyl ethers 2507:The New York Times 2274:. EPA. 8 June 2020 2096:ConsumerNotice.org 1713:Cornell University 1603:www.efsa.europa.eu 1572:The New York Times 1265:The Guardian, 2020 1123:Cornell University 967:In June 2020, the 923: 913:Environmental fate 893:Amaranthus palmeri 812:(EPA) has set the 768:occupational risks 674: 586:Infobox references 21: 3608: 3607: 3513: 3512: 3419: 3418: 3333: 3332: 3254: 3253: 3155:Protox inhibitors 3149: 3148: 3145: 3144: 3072:ACCase inhibitors 2300:. 9 November 2020 2191:. 31 August 2019. 2067:10.1021/es981117e 1756:10.1002/tox.21947 1579:on 4 January 2013 1425:. 25 October 2016 691:phenoxy herbicide 594:Chemical compound 592: 591: 525:Hazard statements 264:CompTox Dashboard 108:Interactive image 3648: 3636:Salicylyl ethers 3430: 3429: 3344: 3343: 3303: 3302: 3212:Pyrimidinediones 3160: 3159: 3077: 3076: 3015: 3014: 2962:Organophosphorus 2704: 2697: 2690: 2681: 2680: 2630: 2629: 2627: 2625: 2613: 2607: 2602: 2596: 2595: 2593: 2591: 2580: 2574: 2573: 2571: 2569: 2554: 2548: 2547: 2526:. New York, NY: 2517: 2511: 2510: 2499: 2493: 2492: 2480: 2474: 2473: 2462: 2456: 2455: 2443: 2437: 2436: 2424: 2418: 2417: 2405: 2399: 2398: 2386: 2380: 2379: 2367: 2361: 2360: 2353: 2347: 2346: 2334: 2328: 2327: 2316: 2310: 2309: 2307: 2305: 2290: 2284: 2283: 2281: 2279: 2268: 2262: 2261: 2259: 2257: 2242: 2236: 2235: 2233: 2231: 2220: 2214: 2213: 2202: 2193: 2192: 2181: 2172: 2171: 2169: 2167: 2152: 2146: 2145: 2143: 2141: 2129: 2123: 2122: 2120: 2118: 2106: 2100: 2099: 2088: 2079: 2078: 2053:(8): 1224–1229. 2042: 2036: 2035: 2007: 2001: 2000: 1990: 1958: 1952: 1951: 1923: 1917: 1916: 1905: 1899: 1898: 1887: 1881: 1880: 1860: 1854: 1848: 1842: 1841: 1839: 1837: 1822: 1813: 1812: 1810: 1808: 1791: 1776: 1775: 1727: 1721: 1720: 1705: 1694: 1693: 1691: 1689: 1669: 1663: 1662: 1660: 1643:(8): 1117–1125. 1628: 1622: 1621: 1619: 1617: 1595: 1589: 1588: 1586: 1584: 1575:. Archived from 1562: 1556: 1555: 1553: 1551: 1540: 1534: 1533: 1531: 1529: 1518: 1512: 1511: 1509: 1507: 1492: 1486: 1485: 1483: 1481: 1469: 1463: 1462: 1460: 1458: 1441: 1435: 1434: 1432: 1430: 1415: 1409: 1408: 1406: 1404: 1389: 1383: 1382: 1380: 1378: 1349: 1343: 1342: 1332: 1322: 1290: 1284: 1283: 1272: 1266: 1260: 1254: 1253: 1236: 1207: 1206: 1193: 1187: 1186: 1153:(5828): 1185–8. 1138: 1127: 1126: 1115: 1109: 1108: 1106: 1098: 1092: 1075: 1069: 1055: 1042: 1037:, 11th Edition, 1030: 1003:punitive damages 907:resistance class 705:and cell death. 562: 558: 554: 540: 536: 532: 504: 499: 398: 383: 377: 371: 365: 358:Chemical formula 288: 287: 272: 270: 254: 234: 223: 209: 192: 181: 170: 150: 130: 110: 86: 31: 24: 20: 3656: 3655: 3651: 3650: 3649: 3647: 3646: 3645: 3611: 3610: 3609: 3604: 3509: 3471: 3415: 3329: 3292: 3250: 3229: 3206: 3141: 3123: 3066: 3004: 2956: 2922:flurochloridone 2908: 2894:copper arsenate 2875: 2819: 2717: 2708: 2639: 2634: 2633: 2623: 2621: 2614: 2610: 2603: 2599: 2589: 2587: 2582: 2581: 2577: 2567: 2565: 2555: 2551: 2528:Audubon Society 2518: 2514: 2501: 2500: 2496: 2481: 2477: 2464: 2463: 2459: 2444: 2440: 2425: 2421: 2406: 2402: 2387: 2383: 2368: 2364: 2355: 2354: 2350: 2335: 2331: 2324:ClassAction.com 2318: 2317: 2313: 2303: 2301: 2292: 2291: 2287: 2277: 2275: 2270: 2269: 2265: 2255: 2253: 2243: 2239: 2229: 2227: 2222: 2221: 2217: 2204: 2203: 2196: 2183: 2182: 2175: 2165: 2163: 2153: 2149: 2139: 2137: 2130: 2126: 2116: 2114: 2107: 2103: 2090: 2089: 2082: 2043: 2039: 2008: 2004: 1959: 1955: 1924: 1920: 1907: 1906: 1902: 1889: 1888: 1884: 1861: 1857: 1849: 1845: 1835: 1833: 1824: 1823: 1816: 1806: 1804: 1792: 1779: 1728: 1724: 1707: 1706: 1697: 1687: 1685: 1670: 1666: 1629: 1625: 1615: 1613: 1597: 1596: 1592: 1582: 1580: 1563: 1559: 1549: 1547: 1542: 1541: 1537: 1527: 1525: 1519: 1515: 1505: 1503: 1493: 1489: 1479: 1477: 1470: 1466: 1456: 1454: 1442: 1438: 1428: 1426: 1417: 1416: 1412: 1402: 1400: 1390: 1386: 1376: 1374: 1350: 1346: 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3383: 3378: 3373: 3368: 3363: 3358: 3352: 3350: 3341: 3335: 3334: 3331: 3330: 3328: 3327: 3322: 3317: 3311: 3309: 3300: 3294: 3293: 3291: 3290: 3285: 3280: 3275: 3270: 3264: 3262: 3256: 3255: 3252: 3251: 3249: 3248: 3243: 3237: 3235: 3231: 3230: 3228: 3227: 3222: 3216: 3214: 3208: 3207: 3205: 3204: 3199: 3194: 3189: 3184: 3179: 3174: 3168: 3166: 3157: 3151: 3150: 3147: 3146: 3143: 3142: 3140: 3139: 3133: 3131: 3129:DIM herbicides 3125: 3124: 3122: 3121: 3116: 3111: 3106: 3101: 3096: 3091: 3085: 3083: 3081:FOP herbicides 3074: 3068: 3067: 3065: 3064: 3059: 3054: 3049: 3044: 3039: 3034: 3029: 3023: 3021: 3012: 3006: 3005: 3003: 3002: 2997: 2992: 2987: 2982: 2977: 2972: 2966: 2964: 2958: 2957: 2955: 2954: 2949: 2944: 2939: 2934: 2929: 2924: 2918: 2916: 2914:HPPD inhbitors 2910: 2909: 2907: 2906: 2901: 2896: 2891: 2889:cacodylic acid 2885: 2883: 2877: 2876: 2874: 2873: 2868: 2863: 2858: 2853: 2848: 2843: 2838: 2832: 2830: 2821: 2820: 2818: 2817: 2812: 2807: 2802: 2797: 2792: 2787: 2782: 2777: 2772: 2767: 2762: 2757: 2752: 2747: 2742: 2737: 2731: 2729: 2719: 2718: 2707: 2706: 2699: 2692: 2684: 2678: 2677: 2672: 2667: 2662: 2657: 2652: 2646: 2638: 2637:External links 2635: 2632: 2631: 2608: 2597: 2575: 2549: 2512: 2494: 2475: 2457: 2438: 2419: 2400: 2381: 2362: 2348: 2329: 2311: 2285: 2263: 2237: 2215: 2194: 2173: 2147: 2124: 2101: 2080: 2037: 2018:(2): 534–538. 2002: 1973:(2): 498–510. 1953: 1934:(6): 858–863. 1918: 1900: 1882: 1855: 1843: 1814: 1777: 1742:(6): 693–703. 1722: 1695: 1664: 1623: 1590: 1557: 1535: 1513: 1487: 1464: 1436: 1410: 1384: 1344: 1285: 1267: 1255: 1208: 1188: 1128: 1110: 1107:. 8 June 2006. 1093: 1070: 1043: 1024: 1023: 1021: 1018: 988: 985: 949: 946: 942:conjugate base 914: 911: 872: 869: 856:In the 2000s, 844: 841: 836: 835:Birds and bees 833: 824: 821: 801: 797: 792: 786: 783: 763: 760: 758: 755: 737: 734: 665: 662: 593: 590: 589: 584: 580:standard state 577: 574: 573: 570: 564: 563: 561:P305+P351+P338 550: 545: 542: 541: 528: 523: 520: 519: 514: 509: 506: 505: 493: 488: 485: 484: 474: 473: 469: 468: 465: 455: 454: 451: 441: 440: 437: 432: 429: 428: 425: 419: 418: 415: 409: 408: 405: 401: 400: 394: 388: 387: 384: 378: 372: 366: 361: 356: 353: 352: 348: 347: 345: 344: 341: 333: 332: 331: 328: 327: 325: 324: 320: 317: 316: 314: 310: 307: 306: 298: 297: 296: 293: 292: 290: 289: 276: 274: 262: 259: 258: 256: 255: 247: 245: 239: 238: 236: 235: 227: 225: 217: 214: 213: 211: 210: 202: 200: 194: 193: 183: 175: 174: 172: 171: 163: 161: 155: 154: 152: 151: 143: 141: 135: 134: 132: 131: 123: 121: 115: 114: 112: 111: 103: 101: 94: 91: 90: 88: 87: 79: 77: 72: 69: 68: 64: 63: 54: 50: 49: 45: 44: 38: 37: 33: 32: 15: 9: 6: 4: 3: 2: 3653: 3642: 3639: 3637: 3634: 3632: 3629: 3627: 3626:Benzoic acids 3624: 3622: 3619: 3618: 3616: 3601: 3598: 3596: 3593: 3591: 3588: 3586: 3583: 3581: 3578: 3576: 3573: 3571: 3568: 3566: 3563: 3561: 3558: 3556: 3553: 3551: 3548: 3546: 3543: 3541: 3538: 3536: 3533: 3531: 3528: 3526: 3523: 3522: 3520: 3516: 3506: 3503: 3501: 3498: 3496: 3493: 3491: 3490:flazasulfuron 3488: 3486: 3485:chlorsulfuron 3483: 3482: 3480: 3478: 3474: 3468: 3465: 3463: 3460: 3458: 3455: 3453: 3450: 3448: 3445: 3443: 3440: 3439: 3437: 3435: 3431: 3428: 3426: 3422: 3412: 3409: 3407: 3404: 3402: 3399: 3397: 3394: 3392: 3389: 3387: 3384: 3382: 3379: 3377: 3374: 3372: 3369: 3367: 3364: 3362: 3359: 3357: 3354: 3353: 3351: 3349: 3345: 3342: 3340: 3336: 3326: 3323: 3321: 3318: 3316: 3313: 3312: 3310: 3308: 3304: 3301: 3299: 3295: 3289: 3286: 3284: 3281: 3279: 3276: 3274: 3271: 3269: 3266: 3265: 3263: 3261: 3257: 3247: 3246:sulfentrazone 3244: 3242: 3241:carfentrazone 3239: 3238: 3236: 3234:Triazolinones 3232: 3226: 3223: 3221: 3218: 3217: 3215: 3213: 3209: 3203: 3200: 3198: 3195: 3193: 3190: 3188: 3185: 3183: 3180: 3178: 3175: 3173: 3170: 3169: 3167: 3165: 3161: 3158: 3156: 3152: 3138: 3135: 3134: 3132: 3130: 3126: 3120: 3117: 3115: 3112: 3110: 3107: 3105: 3102: 3100: 3097: 3095: 3092: 3090: 3087: 3086: 3084: 3082: 3078: 3075: 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795: 782: 780: 776: 771: 769: 754: 751: 747: 743: 733: 731: 726: 722: 718: 713: 711: 706: 704: 700: 696: 692: 688: 684: 680: 670: 661: 659: 655: 650: 648: 644: 639: 637: 635: 630: 627: 623: 619: 615: 611: 607: 603: 599: 587: 581: 575: 571: 569: 566: 565: 551: 548: 544: 543: 529: 526: 522: 521: 518: 515: 512: 508: 507: 503: 498: 494: 491: 487: 486: 482: 480: 475: 470: 467:922 g/L 466: 464: 460: 457: 456: 453:810 g/L 452: 450: 446: 443: 442: 438: 435: 431: 430: 426: 424: 423:Melting point 421: 420: 416: 414: 411: 410: 406: 403: 402: 395: 393: 390: 389: 362: 359: 355: 354: 349: 340: 339: 336: 329: 315: 305: 304: 301: 294: 286: 282: 281:DTXSID4024018 278: 277: 275: 265: 261: 260: 253: 249: 248: 246: 244: 241: 240: 233: 229: 228: 226: 220: 216: 215: 208: 204: 203: 201: 199: 196: 195: 191: 187: 184: 182: 180:ECHA InfoCard 177: 176: 169: 165: 164: 162: 160: 157: 156: 149: 145: 144: 142: 140: 137: 136: 129: 125: 124: 122: 120: 117: 116: 109: 105: 104: 102: 98: 93: 92: 85: 81: 80: 78: 75: 71: 70: 65: 58: 55:3,6-Dichloro- 51: 43: 39: 34: 30: 25: 19: 3631:Chloroarenes 3595:pyribenzoxim 3590:prosulfocarb 3580:metam sodium 3442:chlortoluron 3225:saflufenacil 2927:isoxaflutole 2850: 2836:aminopyralid 2800:pretilachlor 2770:dimethenamid 2765:diflufenican 2711:Pest control 2622:. Retrieved 2611: 2600: 2588:. Retrieved 2578: 2566:. Retrieved 2562: 2552: 2521: 2515: 2506: 2497: 2488: 2478: 2469: 2460: 2452:stltoday.com 2451: 2441: 2433:stltoday.com 2432: 2422: 2413: 2403: 2395:stltoday.com 2394: 2384: 2376:stltoday.com 2375: 2365: 2351: 2342: 2332: 2323: 2314: 2302:. Retrieved 2297: 2288: 2276:. Retrieved 2266: 2254:. Retrieved 2250: 2240: 2228:. Retrieved 2218: 2209: 2188: 2164:. Retrieved 2160: 2150: 2138:. Retrieved 2127: 2115:. Retrieved 2104: 2095: 2050: 2046: 2040: 2015: 2011: 2005: 1970: 1966: 1956: 1931: 1927: 1921: 1912: 1903: 1894: 1885: 1868: 1865:Weed Science 1864: 1858: 1846: 1834:. Retrieved 1805:. Retrieved 1799: 1739: 1735: 1725: 1717:the original 1686:. Retrieved 1681: 1677: 1667: 1640: 1636: 1626: 1614:. Retrieved 1602: 1593: 1581:. Retrieved 1577:the original 1570: 1560: 1548:. Retrieved 1538: 1526:. Retrieved 1516: 1504:. Retrieved 1500: 1490: 1478:. Retrieved 1467: 1455:. Retrieved 1449: 1439: 1427:. Retrieved 1413: 1401:. Retrieved 1387: 1375:. Retrieved 1363: 1357: 1347: 1302: 1298: 1288: 1279: 1270: 1258: 1250:the original 1243: 1200: 1191: 1150: 1146: 1122: 1113: 1096: 1079: 1073: 1058: 1038: 1032: 1028: 1011: 1007: 994: 990: 981: 977: 966: 955: 951: 931: 924: 904: 897: 891: 874: 866: 855: 848: 846: 838: 826: 818: 806: 788: 772: 765: 739: 714: 707: 675: 651: 640: 636:-anisic acid 633: 621: 617: 613: 609: 605: 597: 596: 516: 478: 148:ChEMBL476936 67:Identifiers 59:-anisic acid 56: 53:Other names 18: 3467:tebuthiuron 3462:monolinuron 3220:butafenacil 3202:oxyfluorfen 3182:fluorodifen 3172:acifluorfen 3089:chlorazifop 3037:dichlorprop 2990:glufosinate 2952:sulcotrione 2861:pyrithiobac 2815:trifluralin 2785:metolachlor 2780:metazachlor 2750:benfluralin 2624:15 December 2568:17 December 2563:fortune.com 2136:. Crop Life 1928:Groundwater 1616:23 December 1528:27 December 1377:10 November 1034:Merck Index 647:spray drift 626:chlorinated 568:Flash point 511:Signal word 404:Appearance 351:Properties 186:100.016.033 128:CHEBI:81856 3615:Categories 3585:metribuzin 3565:indaziflam 3545:bromoxynil 3505:tribenuron 3411:metamitron 3371:hexazinone 3298:Quaternary 3273:fluroxypyr 3137:sethoxydim 3119:quizalofop 3104:fenoxaprop 3000:piperophos 2995:glyphosate 2947:sethoxydim 2942:nitisinone 2937:mesotrione 2881:Arsenicals 2866:quinclorac 2846:clopyralid 2841:chloramben 2805:propachlor 2735:acetochlor 2715:herbicides 1871:(2): 164. 1423:KTIC Radio 1403:29 October 1078:Record of 1020:References 884:glyphosate 871:Resistance 757:Toxicology 719:plants by 703:senescence 629:derivative 490:Pictograms 459:Solubility 445:Solubility 392:Molar mass 252:SJG3M6RY6H 159:ChemSpider 95:3D model ( 74:CAS Number 3575:methazole 3550:clomazone 3530:aclonifen 3406:terbutryn 3386:propazine 3381:prometryn 3366:cyanazine 3339:Triazines 3315:cyperquat 3288:triclopyr 3283:thiazopyr 3268:dithiopyr 3260:Pyridines 3187:fomesafen 3114:haloxyfop 3109:fluazifop 3094:cyhalofop 2975:bialaphos 2970:bensulide 2871:quinmerac 2760:diethatyl 2755:butachlor 2536:0004-7694 2075:0013-936X 2032:0021-8561 1480:16 August 1457:16 August 1429:4 October 1240:"Dicamba" 1197:"Dicamba" 602:herbicide 481:labelling 84:1918-00-9 3540:Bentazon 3396:simetryn 3391:simazine 3376:prometon 3361:atrazine 3325:paraquat 3278:imazapyr 3197:nitrofen 3192:lactofen 3099:diclofop 3057:mecoprop 3042:fenoprop 2985:fosamine 2980:ethephon 2856:picloram 2825:Aromatic 2810:propanil 2790:oryzalin 2775:flamprop 2740:alachlor 2727:anilines 2723:Anilides 2590:11 March 1997:19616011 1836:3 August 1807:1 August 1772:45373092 1764:24420721 1688:13 April 1583:1 August 1339:21408147 1299:PLOS ONE 1175:17525337 987:Lawsuits 961:Missouri 957:Arkansas 858:Monsanto 781:in men. 742:drifting 721:Monsanto 658:Monsanto 622:Vanquish 472:Hazards 22:Dicamba 3570:juglone 3560:dinoseb 3457:monuron 3452:linuron 3356:ametryn 3177:bifenox 3062:2,4,5-T 3010:Phenoxy 2851:dicamba 2544:6823366 2523:Audubon 2278:11 June 2256:11 June 2230:11 June 2166:7 March 2140:10 July 2117:10 July 2055:Bibcode 1988:3109874 1936:Bibcode 1744:Bibcode 1658:2920083 1550:10 July 1506:24 June 1398:Reuters 1372:3740338 1330:3050828 1307:Bibcode 1183:7093076 1155:Bibcode 1147:Science 1087:of the 1083:in the 1080:Dicamba 862:soybean 785:Mammals 695:conifer 683:legumes 679:bracken 598:Dicamba 463:ethanol 449:acetone 413:Density 219:PubChem 3518:Others 3320:diquat 3032:2,4-DB 3019:Auxins 2745:asulam 2542:  2534:  2530:: 45. 2304:26 May 2251:US EPA 2073:  2030:  1995:  1985:  1770:  1762:  1655:  1370:  1337:  1327:  1181:  1173:  762:Humans 618:Oracle 614:Diablo 610:Banvel 606:Dianat 517:Danger 439:"low" 397:221.03 335:SMILES 207:C18597 139:ChEMBL 61:Dianat 36:Names 3600:Ziram 3425:Ureas 3027:2,4-D 2828:acids 1830:Yahoo 1768:S2CID 1368:JSTOR 1179:S2CID 1105:(PDF) 814:NOAEL 736:Drift 687:cacti 417:1.57 300:InChI 119:ChEBI 97:JSmol 3555:DCBN 3525:3-AT 3447:DCMU 3052:MCPB 3047:MCPA 2904:MSMA 2899:DSMA 2626:2020 2592:2020 2570:2020 2540:OCLC 2532:ISSN 2306:2021 2280:2020 2258:2020 2232:2020 2168:2018 2142:2017 2119:2017 2071:ISSN 2028:ISSN 1993:PMID 1838:2016 1809:2016 1760:PMID 1690:2021 1684:(11) 1618:2023 1585:2016 1552:2020 1530:2021 1508:2017 1482:2016 1459:2016 1431:2017 1405:2016 1379:2020 1335:PMID 1171:PMID 1039:3026 998:BASF 959:and 896:and 685:and 620:and 557:P280 553:P273 539:H412 535:H318 531:H302 243:UNII 232:3030 198:KEGG 168:2922 2063:doi 2020:doi 1983:PMC 1975:doi 1971:392 1944:doi 1873:doi 1801:NPR 1752:doi 1653:PMC 1645:doi 1641:118 1607:doi 1325:PMC 1315:doi 1163:doi 1151:316 1063:doi 725:EPA 654:GMO 631:of 479:GHS 461:in 447:in 269:EPA 222:CID 3617:: 2713:: 2561:. 2538:. 2505:. 2487:. 2468:. 2450:. 2431:. 2412:. 2393:. 2374:. 2341:. 2322:. 2296:. 2249:. 2208:. 2197:^ 2187:. 2176:^ 2159:. 2094:. 2083:^ 2069:. 2061:. 2051:33 2049:. 2026:. 2016:37 2014:. 1991:. 1981:. 1969:. 1965:. 1942:. 1932:38 1930:. 1911:. 1893:. 1869:49 1867:. 1828:. 1817:^ 1798:. 1780:^ 1766:. 1758:. 1750:. 1740:30 1738:. 1734:. 1698:^ 1682:10 1680:. 1676:. 1651:. 1639:. 1635:. 1601:. 1569:. 1499:. 1448:. 1421:. 1396:. 1364:41 1362:. 1356:. 1333:. 1323:. 1313:. 1301:. 1297:. 1278:. 1242:. 1211:^ 1199:. 1177:. 1169:. 1161:. 1149:. 1145:. 1131:^ 1121:. 1046:^ 802:50 798:50 793:50 791:LD 732:. 616:, 612:, 608:, 559:, 555:, 537:, 533:, 483:: 376:Cl 2725:/ 2703:e 2696:t 2689:v 2628:. 2594:. 2572:. 2546:. 2491:. 2454:. 2435:. 2416:. 2397:. 2378:. 2359:. 2345:. 2326:. 2308:. 2282:. 2260:. 2234:. 2212:. 2170:. 2144:. 2121:. 2098:. 2077:. 2065:: 2057:: 2034:. 2022:: 1999:. 1977:: 1950:. 1946:: 1938:: 1915:. 1897:. 1879:. 1875:: 1840:. 1811:. 1774:. 1754:: 1746:: 1692:. 1661:. 1647:: 1620:. 1609:: 1587:. 1554:. 1532:. 1510:. 1484:. 1461:. 1433:. 1407:. 1381:. 1341:. 1317:: 1309:: 1303:6 1185:. 1165:: 1157:: 1125:. 1065:: 1041:. 634:o 385:3 382:O 379:2 373:6 370:H 367:8 364:C 271:) 267:( 99:) 57:o

Index


Preferred IUPAC name
CAS Number
1918-00-9
JSmol
Interactive image
ChEBI
CHEBI:81856
ChEMBL
ChEMBL476936
ChemSpider
2922
ECHA InfoCard
100.016.033
Edit this at Wikidata
KEGG
C18597
PubChem
3030
UNII
SJG3M6RY6H
CompTox Dashboard
DTXSID4024018
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Density
Melting point

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