Page last updated: 2024-12-05

dicamba

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dicamba: A chlorinated organic herbicide. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3030
CHEMBL ID476936
CHEBI ID81856
SCHEMBL ID18336
MeSH IDM0006261

Synonyms (126)

Synonym
unii-sjg3m6ry6h
3,6-dichloor-2-methoxy-benzoeizuur
kyselina 3,6-dichlor-2-methoxybenzoova
3,6-dichlor-3-methoxy-benzoesaeure
mais banvel wg
aviator
acido (3,6-dicloro-2-metossi)-benzoico
celebrity b
sjg3m6ry6h ,
velsicol 58cs11
KBIO1_001468
DIVK1C_006524
banvel
SPECTRUM_001827
o-anisic acid, 3,6-dichloro-
benzoic acid, 3,6-dichloro-2-methoxy-
SPECTRUM5_001960
OPREA1_626816
BSPBIO_002347
banvel herbicide
3,6-dichloor-2-methoxy-benzoeizuur [dutch]
3,6-dichloro-o-anisic acid
hsdb 311
dicamba [ansi:bsi:iso]
banvel 70wp
compound b [velsicol]
velsicol 58-cs-11
acido (3,6-dicloro-2-metossi)-benzoico [italian]
einecs 217-635-6
brn 2453039
compound b dicamba
3,6-dichlor-3-methoxy-benzoesaeure [german]
2,5-dichloro-6-methoxybenzoic acid
epa pesticide chemical code 029801
ai3-27556
velsicol compound r
ccris 1471
kyselina 3,6-dichlor-2-methoxybenzoova [czech]
banvel ii herbicide
banvel cst
dianat [russian]
brush buster
2-methoxy-3,6-dichlorobenzoic acid
mdba
banvel sgf
mediben
banvel 480
dianat
banlen
caswell no. 295
dicamba, plant cell culture tested, bioreagent
NCGC00094526-01
NCGC00094526-03
NCGC00094526-02
KBIO2_004897
KBIO2_007465
KBIO2_002329
KBIOGR_001067
KBIO3_001847
KBIOSS_002332
SPECPLUS_000428
SPECTRUM4_000664
SPECTRUM2_001882
SPECTRUM3_000824
SPBIO_001784
SPECTRUM330032
3,6-dichloro-2-methoxybenzoic acid
dicamba
1918-00-9
NCGC00094526-05
NCGC00094526-04
D3M ,
AKOS000273802
CHEMBL476936
chebi:81856 ,
3,6 dichloromethoxybenzoic acid
FT-0666529
inchi=1/c8h6cl2o3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3h,1h3,(h,11,12)
iwedixlbflaxbo-uhfffaoysa-
NCGC00094526-06
NCGC00094526-07
C18597
dtxsid4024018 ,
cas-1918-00-9
dtxcid904018
tox21_201356
tox21_300661
NCGC00258908-01
NCGC00254569-01
A813521
CCG-39335
3,6-dichloro-2-methoxy-d3-benzoic acid
FT-0633910
dicamba [iso]
dicamba [mi]
dicamba [hsdb]
STL455891
SCHEMBL18336
KS-5270
3,6-dichloro-2-methoxy-benzoic acid
2-methoxy-3,6-dichloro-benzoic acid
banex (salt/mix)
banvel d (salt/mix)
banvel 200 (salt/mix)
fallow master (salt/mix)
banvel 4s (salt/mix)
velsicol compound ''r''
3,6-dichloro-o-anisic acid plant cell*culture tes
62610-39-3
benzoic acid,3,6-dichloro-2-methoxy-
mfcd00055283
dicamba, pestanal(r), analytical standard
dicamba, certified reference material, tracecert(r)
dicamba 10 microg/ml in acetonitrile
dicamba 100 microg/ml in acetonitrile
J-012397
dicamba-[13c6]
Q424684
dicamba, [ring-14c(u)]
89300-29-8
D4800
AMY40792
CS-0081338
H10363
SY107360
EN300-8153644

Research Excerpts

Overview

Dicamba is an important herbicide for controlling post-emergent resistant weeds in soybean farming. Dicamba O-demethylase is a multicomponent enzyme from Pseudomonas maltophilia, strain DI-6. It catalyzes the conversion of the widely used herbicide dicamba (2-methoxy-3,6-dichlorobenzoic acid) to DCSA.

ExcerptReferenceRelevance
"Dicamba is an important herbicide for controlling post-emergent resistant weeds in soybean farming. "( Conversations about the Future of Dicamba: The Science Behind Off-Target Movement.
Hapeman, CJ; Kruger, GR; MacInnes, A; Pai, N; Reiss, R; Riter, LS; Vieira, BC, 2021
)
2.34
"Dicamba is a widely applied herbicide for crop protection and has potential for volatility. "( Dicamba-Based Herbicides: Herbicidal Ionic Liquids versus Commercial Forms.
Chrzanowski, Ł; Kaczmarek, DK; Niemczak, M; Pernak, J; Praczyk, T; Rzemieniecki, T, 2020
)
3.44
"Dicamba is a benzoic acid herbicide used to target woody and broadleaf weeds in industrial, domestic, and municipal spheres. "( Dicamba elevates concentrations of S-adenosyl methionine but does not induce oxidative stress or alter DNA methylation in rainbow trout (Oncorhynchus mykiss) hepatocytes.
Hontela, A; Ilnytskyy, Y; Jamwal, A; Miller, JGP; Wiseman, SB, 2020
)
3.44
"Dicamba is a benzoic acid herbicide that has been detected in surface and ground water. "( Dicamba affects sex steroid hormone level and mRNA expression of related genes in adult rare minnow (Gobiocypris rarus) at environmentally relevant concentrations.
Li, W; Wang, Z; Zha, J; Zhu, L,
)
3.02
"Dicamba is a very important herbicide that is widely used to control more than 200 types of broadleaf weeds and is a suitable target herbicide for the engineering of herbicide-resistant transgenic crops. "( A Tetrahydrofolate-Dependent Methyltransferase Catalyzing the Demethylation of Dicamba in Sphingomonas sp. Strain Ndbn-20.
Ding, DR; He, J; Hong, Q; Qiu, JG; Tao, Q; Xie, XT; Yan, X; Yao, L; Yu, LL; Zhang, JJ, 2016
)
2.1
"Dicamba O-demethylase is a multicomponent enzyme that catalyzes the conversion of the herbicide 2-methoxy-3,6-dichlorobenzoic acid (dicamba) to 3,6-dichlorosalicylic acid (DCSA). "( A three-component dicamba O-demethylase from Pseudomonas maltophilia, strain DI-6: purification and characterization.
Arendsen, AF; Behrens, M; Carlson, DL; Chakraborty, S; Hagen, WR; Herman, PL; Wang, XZ; Weeks, DP, 2005
)
2.1
"Dicamba O-demethylase is a multicomponent enzyme from Pseudomonas maltophilia, strain DI-6, that catalyzes the conversion of the widely used herbicide dicamba (2-methoxy-3,6-dichlorobenzoic acid) to DCSA (3,6-dichlorosalicylic acid). "( A three-component dicamba O-demethylase from Pseudomonas maltophilia, strain DI-6: gene isolation, characterization, and heterologous expression.
Barycki, J; Behrens, M; Chakraborty, S; Chrastil, BM; Herman, PL; Weeks, DP, 2005
)
2.1
"Dicamba is an herbicide commonly applied to crops in the United States and abroad. "( Cancer incidence among pesticide applicators exposed to dicamba in the agricultural health study.
Alavanja, MC; Blair, A; Dosemeci, M; Hoppin, JA; Hou, L; Lubin, J; Rusiecki, J; Samanic, C; Sandler, DP, 2006
)
2.02

Effects

ExcerptReferenceRelevance
"Dicamba has been used worldwide for 60 years, but few studies have been conducted on its environmental safety and health effects. "( Teratogenic effects of the dicamba herbicide in Zebrafish (Danio rerio) embryos.
Bernert, K; da Silva Milhorini, S; Felisbino, K; Guiloski, IC; Kirsten, N; Marçal, IS; Nominato-Oliveira, L; Schiessl, R, 2023
)
2.65

Actions

ExcerptReferenceRelevance
"Dicamba alone did not increase the number or volume of these altered hepatic foci."( Promoting activity of the herbicide dicamba (2-methoxy-3, 6-dichlorobenzoic acid) in two stage hepatocarcinogenesis.
Espandiari, P; Glauert, HP; Lee, EY; Robertson, LW, 1999
)
1.3

Toxicity

The results could indicate that dicamba-based formulation Banvel(®) is the less toxic emerging pollutant reported so far. Commonly used herbicides 2,4-D and Dicamba were shown to increase toxicity measured with the Microtox test.

ExcerptReferenceRelevance
" Female animals showed increased sensitivity to the toxic effects by DNOC at the highest dose."( Genetic safety evaluation of pesticides in different short-term tests.
Cantelli-Forti, G; Colacci, A; Grilli, S; Hrelia, P; Maffei, F; Morotti, M; Perocco, P; Vigagni, F, 1994
)
0.29
" Commonly used herbicides 2,4-D and dicamba were shown to increase toxicity measured with the Microtox test at low irradiation doses resulting from formation of more toxic transient products, which can be decomposed at larger doses."( Monitoring of toxicity during degradation of selected pesticides using ionizing radiation.
Bojanowska-Czajka, A; Drzewicz, P; Gryz, M; Głuszewski, W; Kulisa, K; Nałecz-Jawecki, G; Sawicki, J; Trojanowicz, M; Wołkowicz, S, 2004
)
0.6
"Pesticides are toxic agents intentionally released into the environment; their use raises public health and environmental concerns."( Modulation of the genotoxicity of pesticides reacted with redox-modified smectite clay.
Plewa, MJ; Sorensen, KC; Stucki, JW; Wagner, ED; Warner, RE, 2005
)
0.33
" Further investigations are needed to acquire a comprehensive knowledge of the possible mechanism/s through dicamba and banvel exert their toxic effects."( Dicamba-induced genotoxicity in Chinese hamster ovary (CHO) cells is prevented by vitamin E.
González, NV; Larramendy, ML; Soloneski, S, 2009
)
2.01
" All DMO forms maintain the characteristics of Rieske oxygenases that have a history of safe use."( Safety assessment of dicamba mono-oxygenases that confer dicamba tolerance to various crops.
Bell, E; Burzio, LA; Glenn, KC; Kessenich, C; Koch, MS; Li, B; Silvanovich, A; Wang, C, 2016
)
0.75
" However the knowledge of their potential toxic effects are still limited."( Toxicity evaluation of selected ammonium-based ionic liquid forms with MCPP and dicamba moieties on Pseudomonas putida.
Chrzanowski, Ł; Heipieper, HJ; Piotrowska, A; Syguda, A; Wyrwas, B, 2017
)
0.68
" The results showed delayed toxic effects of auxin simulators, especially 2,4-D in the Lemna test."( The impact of humic acid on toxicity of individual herbicides and their mixtures to aquatic macrophytes.
Ivančev Tumbas, I; Lazić, S; Mihajlović, V; Molnar Jazić, J; Šunjka, D; Teodorović, I; Tomić, T; Tubić, A, 2019
)
0.51
" The aim of this study was to evaluate the acute toxic effects and the prevailing interactions on stage 36 tadpoles of the anuran species Rhinella arenarum when exposed to equitoxic and non-equitoxic combinations of these herbicide combinations."( Toxicity to Rhinella arenarum tadpoles (Anura, Bufonidae) of herbicide mixtures commonly used to treat fallow containing resistant weeds: glyphosate-dicamba and glyphosate-flurochloridone.
Brodeur, JC; Larramendy, ML; Ruiz de Arcaute, C; Soloneski, S, 2020
)
0.76
"Due to rising concerns for environmental and human health, many toxic compounds, such as auxin-based herbicides, have been tested in relation their toxicity effect."( Searching an auxinic herbicide to use as positive control in toxicity assays.
Alves, TA; Clarindo, WR; Ferreira, A; Henrique, MKC; Pinheiro, PF; Praça-Fontes, MM; Roberto, CEO, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
"A simultaneous pharmacokinetic study of two chemicals has been conducted on a clinically stabilized human who had intentionally ingested a mixture of 2,4-D and Dicamba."( Pharmacokinetic study of a patient intoxicated with 2,4-dichlorophenoxyacetic acid and 2-methoxy-3,6-dichlorobenzoic acid.
Haley, TJ; Young, JF, 1977
)
0.45

Dosage Studied

English Pointer dogs dosed with encapsulated 2,4-D or 2-methoxy-3,6-dichlorobenzoic acid developed varying degrees of myotonia. A low H2O2 dosage in photocatalysis using UV 300 nm would enhance the decay rate of dicamba by 2.

ExcerptRelevanceReference
"English Pointer dogs dosed po with encapsulated 2,4-dichlorophenoxyacetic acid (2,4-D) or 2-methoxy-3,6-dichlorobenzoic acid (dicamba) developed varying degrees of myotonia."( 2,4-D toxicosis. I: A pilot study of 2,4-dichlorophenoxyacetic acid- and dicamba-induced myotonia in experimental dogs.
Arnold, EK; Beasley, VR; Lovell, RA; Parker, AJ, 1991
)
0.72
" The data, although apparently influenced by season, showed an inverted or U-shaped dose-response pattern for reduced litter size, with the low end of the dose range producing the greatest decrease in the number of live pups born."( Developmental toxicity of a commercial herbicide mixture in mice: I. Effects on embryo implantation and litter size.
Cavieres, MF; Jaeger, J; Porter, W, 2002
)
0.31
" zea showed no negative effects when feeding on soybeans dosed with dicamba."( Direct and indirect effects of the synthetic-auxin herbicide dicamba on two lepidopteran species.
Bohnenblust, E; Egan, JF; Mortensen, D; Tooker, J, 2013
)
0.87
" Using similar methods, a dose-response study was conducted on 2,4-D with and without dicamba."( Unintended effects of the herbicides 2,4-D and dicamba on lady beetles.
Freydier, L; Lundgren, JG, 2016
)
0.91
" Mice orally dosed with each of these DMO proteins showed no adverse effects as evidenced by analysis of body weight gain, food consumption and clinical observations."( Safety assessment of dicamba mono-oxygenases that confer dicamba tolerance to various crops.
Bell, E; Burzio, LA; Glenn, KC; Kessenich, C; Koch, MS; Li, B; Silvanovich, A; Wang, C, 2016
)
0.75
"Levels of 2,4-D and dicamba (3,6-dichloro-2-methoxybenzoic acid) resistance were quantified in a dose-response study and the populations were further screened for auxin selectivity, 2,4-D translocation and metabolism, expression of key 2,4-D-responsive genes and activation of the mitogen-activated proein kinase (MAPK) pathway."( 2,4-D and dicamba resistance mechanisms in wild radish: subtle, complex and population specific?
Goggin, DE; Kaur, P; Owen, MJ; Powles, SB, 2018
)
1.21
" Progenies were subjected to herbicide dose-response studies following drift selection."( Herbicide drift exposure leads to reduced herbicide sensitivity in Amaranthus spp.
Amundsen, KL; Gaines, TA; Kruger, GR; Luck, JD; Vieira, BC; Werle, R, 2020
)
0.56
" Interestingly, subsequent dose-response experiments conducted for two selected dicamba-based products confirmed that the greatest phytotoxicity was expressed by compounds containing a decyl substituent."( Toward revealing the role of the cation in the phytotoxicity of the betaine-based esterquats comprising dicamba herbicide.
Kaczmarek, DK; Niemczak, M; Rzemieniecki, T; Smolibowski, M; Stachowiak, W, 2022
)
1.16
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
herbicideA substance used to destroy plant pests.
synthetic auxinA synthetic compound exhibiting auxin activity.
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
methoxybenzoic acidAny benzoic acid carrying one or more methoxy substituents.
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.17780.003245.467312,589.2998AID2517
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency19.95260.177814.390939.8107AID2147
phosphopantetheinyl transferaseBacillus subtilisPotency7.07950.141337.9142100.0000AID1490
GLI family zinc finger 3Homo sapiens (human)Potency68.58960.000714.592883.7951AID1259369
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency39.81070.011212.4002100.0000AID1030
retinoid X nuclear receptor alphaHomo sapiens (human)Potency54.94100.000817.505159.3239AID1159527
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency0.03550.010039.53711,122.0200AID588545
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID439610Antagonist activity at human T1R2/T1R3 receptor expressed in HEK293E cells assessed as inhibition of sucralose-induced intracellular calcium mobilization up to 1 mM2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Phenoxy herbicides and fibrates potently inhibit the human chemosensory receptor subunit T1R3.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (227)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (12.33)18.7374
1990's17 (7.49)18.2507
2000's58 (25.55)29.6817
2010's73 (32.16)24.3611
2020's51 (22.47)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.93

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.93 (24.57)
Research Supply Index5.48 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index131.01 (26.88)
Search Engine Supply Index3.86 (0.95)

This Compound (43.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews6 (2.52%)6.00%
Case Studies3 (1.26%)4.05%
Observational0 (0.00%)0.25%
Other229 (96.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]