Dicamba
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| Category | Agricultural |
| Catalog number | BBF-05901 |
| CAS | 1918-00-9 |
| Molecular Weight | 221.03 |
| Molecular Formula | C8H6Cl2O3 |
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Description
Dicamba is a broad-spectrum herbicide used to control grain crops and turf areas.
Specification
| Synonyms | Benzoic acid, 3,6-dichloro-2-methoxy-; Mdba |
| IUPAC Name | 3,6-dichloro-2-methoxybenzoic acid |
| Canonical SMILES | COC1=C(C=CC(=C1C(=O)O)Cl)Cl |
| InChI | InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12) |
| InChI Key | IWEDIXLBFLAXBO-UHFFFAOYSA-N |
Properties
| Application | Herbicide |
| Melting Point | 115°C |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity | LD50: 757 mg/kg body weight (oral, rats), LD50 >2,000 mg/kg (dermal, rats), LC50 >200 mg/L (inhalation, rats). |
Reference Reading
1. Evaluation of dicamba volatilization when mixed with glyphosate using imazethapyr as a tracer
Maria Leticia Zaccaro-Gruener, Jason K Norsworthy, Chad B Brabham, L Tom Barber, Thomas R Butts, Trenton L Roberts, Andy Mauromoustakos J Environ Manage. 2022 Sep 1;317:115303. doi: 10.1016/j.jenvman.2022.115303. Epub 2022 May 22.
Expansion of dicamba-resistant crops increased the frequency of off-target movement issues, especially in the midsouthern United States. Six field trials were conducted over two growing seasons with the purpose to determine the contribution of volatilization and physical suspension of particles to the off-target movement of dicamba when applied with glyphosate and imazethapyr - a non-volatile herbicide used as a tracer for physical off-target movement. Applications included dicamba at 560 g ha-1, glyphosate at 1260 g ha-1, and imazethapyr at 105 g ha-1. Applicators include glyphosate with dicamba to increase the spectrum of weed control from these applications; however, this addition increases potential for dicamba volatilization. Following application of the mixture, air samplers were placed in the field to collect dicamba and imazethapyr. Results showed there was at least 50 times more dicamba than imazethapyr detected even though the dicamba:imazethapyr ratio applied was 5.3:1. Dicamba was detected in the treated area and the off-site locations and all intervals of air sampling, ranging from 126 to 5990 ng. No more than 37.5 ng of imazethapyr was detected during the first 24-h after application (HAA) inside the treated area. Imazethapyr was only detected in 9 of the 20 sampling combinations during these experiments, and most of these detections (6) occurred during the first 24 HAA and inside the treated area. While some movement from the suspension of particles occurred based on the detection of imazethapyr in air samples, results show that most dicamba detection was due to the volatilization of the herbicide.
2. Inheritance of dicamba-resistance in allotetraploid Chenopodium album
Hossein Ghanizadeh, Kerry C Harrington, Lulu He, Trevor K James Pest Manag Sci. 2022 Nov;78(11):4939-4946. doi: 10.1002/ps.7114. Epub 2022 Aug 17.
Background: Chenopodium album L. is a troublesome weed in spring-planted crops, and different levels of ploidy have been documented for this weed species. A population of C. album has evolved resistance to dicamba. The level of ploidy and inheritance of dicamba resistance was studied in this population. Results: The resistant and susceptible individuals of C. album were confirmed as tetraploid by flow cytometry. Pair-crosses were made between ten resistant and susceptible individuals. Eight F1 individuals from five crosses were confirmed resistant after treating with dicamba at 400 g a.e. ha-1 . These individuals were selfed, and the response of their progenies to dicamba was assessed in dose-response experiments, and the results confirmed the resistance trait was dominant. Furthermore, an analysis of the segregation patterns revealed that the segregation response of all F2 progenies fitted a 3:1 (resistant/susceptible) ratio when treated with dicamba at 200, 400 and 800 g a.e. ha-1 , suggesting a single gene was responsible for dicamba resistance. Conclusions: Dicamba resistance in the studied tetraploid population of C. album is governed by a single dominant gene. This type of inheritance suggests that selection for dicamba resistance can occur readily. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
3. Utility of roller wiper applications of dicamba for Palmer amaranth control in soybean
Rodger Farr, Jason K Norsworthy, L Tom Barber, Thomas R Butts, Trent Roberts Pest Manag Sci. 2022 Jun;78(6):2151-2160. doi: 10.1002/ps.6838. Epub 2022 Mar 12.
Background: The commercialization of dicamba-resistant soybean has resulted in increased concern for off-target movement of dicamba onto sensitive vegetation. To mitigate the off-target movement through physical drift, one might consider use of rope wicks and other wiper applicators. Although wiper-type application methods have been efficacious in pasture settings, the utility of dicamba using wiper applicators in agronomic crops is not available in scientific literature. To determine the utility of roller wipers for dicamba applications in dicamba-resistant soybean, two separate experiments were conducted in the summer of 2020 and replicated in both Keiser and Fayetteville, AR, USA. Results: Utilizing opposing application directions and a 2:1:1 ratio of water: formulated glyphosate: formulated dicamba were the most efficacious practices for controlling Palmer amaranth. The high herbicide concentrations and wiping in opposing directions increased dicamba-resistant soybean injury when the wiper contacted the crop, but no yield loss was observed because of this injury. Broadcast applications resulted in greater Palmer amaranth mortality than roller wiper applications, and the most effective roller wiper treatments were when two sequential applications were made inside the crop canopy. Conclusions: Dicamba applications require adequate coverage for optimum weed control. While efforts can be made to increase roller wiper efficacy by optimizing coverage and timing of applications, broadcast applications are superior to roller wiper applicators for weed control. Roller wiper applications did not reduce soybean yield, thus wiper-type applications may be safely used in dicamba-resistant soybean, albeit the likelihood for off-target damage caused by volatilization of these treatments would need to be investigated. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
LC-MS/MS Spectrum - 45V, Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H6Cl2O3
Molecular Weight (Monoisotopic Mass): 219.9694 Da
Molecular Weight (Avergae Mass): 221.037 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: CDCl3
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
