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Description

clethodim: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

clethodim : An oxime O-ether resulting from the formal conversion ot the acyclic keto group of 5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propionylcyclohex-2-en-1-one to the corresponding oxime with subsequent O-alkylation of the oxime by an (E)-3-chloroallyl group. It is used as a selective postemergence herbicide for the control of annual and perennial grasses in numerous crops, including alfalfa, celery, clover, conifers, cotton, cranberries, garlic, onions, ornamentals, peanuts, soybeans, strawberries, sugarbeet, sunflowers, and vegetables; the (-)-enantiomer has been reported to be more active than the (+)-enantiomer. [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 CID135491728
CHEBI ID70721
SCHEMBL ID53788
SCHEMBL ID336564
SCHEMBL ID10769831
MeSH IDM0022842

Synonyms (50)

Synonym
clethodim
clethodim [iso]
select
centurion
NCGC00163922-01
2-[(1e)-n-{[(2e)-3-chloroprop-2-en-1-yl]oxy}propanimidoyl]-5-[2-(ethylthio)propyl]-3-hydroxycyclohex-2-en-1-one
2-cyclohexen-1-one, 2-(1-(((3-chloro-2-propenyl)oxy)imino)propyl)-5-(2-(ethylthio)propyl)-3-hydroxy-
99129-21-2
C18609
ogive
epa pesticide chemical code 121011
re 45601
prism (pesticide)
volunteer
trigger [pesticide]
hsdb 7960
prism
2-((1e)-n-(((2e)-3-chloro-2-propen-1-yl)oxy)propanimidoyl)-5-(2-(ethylsulfanyl)propyl)-3-hydroxy-2-cyclohexen-1-one
select max
centurion 240
2-(1-(((3-chloro-2-propenyl)oxy)imino)propyl)-5-(2-(ethylthio)propyl)-3-hydroxy-2-cyclohexen-1-one
clethodime
05sb62ib6f ,
ccris 9262
unii-05sb62ib6f
2-{(e)-1-[(e)-3-chloroallyloxyimino]propyl}-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one
2-(n-{[(2e)-3-chloroprop-2-en-1-yl]oxy}propanimidoyl)-5-[2-(ethylsulfanyl)propyl]-3-hydroxycyclohex-2-en-1-one
CHEBI:70721
2-[1-[[[(2e)-3-chloro-2-propen-1-yl]oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one
SCHEMBL53788
SCHEMBL336564
SCHEMBL10769831
dtxcid1014458
NCGC00357238-01
tox21_304029
dtxsid3034458 ,
cas-99129-21-2
mfcd01632327
2-[(e)-n-[(e)-3-chloroprop-2-enoxy]-c-ethylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one
AKOS032954338
clethodim, technical grade
AS-15187
Q27294484
(z)-clethodim
clethodim 100 microg/ml in acetonitrile
clethodim, (e,e)-(+/-)-
DLY40VJ33K
2-((e)-n-((e)-3-chloroallyloxy)-c-ethyl-carbonimidoyl)-5-(2-ethylsulfanylpropyl)-3-hydroxy-cyclohex-2-en-1-one
clethodim, (e)-
AKOS040744641

Toxicity

ExcerptReference
" Photodegraded solutions of clethodim were shown to be more toxic to the bacteria Vibrio fischeri than the herbicide itself, reaching the maximum toxicity when the herbicide is completely degraded."( Photolysis of clethodim herbicide and a formulation in aquatic environments: Fate and ecotoxicity assessment of photoproducts by QSAR models.
Alonso-Prados, JL; Calvo, L; López-Goti, C; Sandín-España, P; Sevilla-Morán, B; Villaverde, JJ, 2018
)
"Clethodim is one of the most widely used herbicides in agriculture, however, its potential toxic effects on organisms and the underlying toxicity mechanism are still poorly understood."( Clethodim exposure induced development toxicity and behaviour alteration in early stages of zebrafish life.
Cao, Z; Huang, P; Jiang, F; Liao, X; Lu, H; Meng, Z; Su, M; Wang, H; Zhang, S; Zhou, L, 2019
)

Dosage Studied

ExcerptReference
" Subsequent comparisons of the dose-response characteristics of the original and low dose-selected VLR1 lines demonstrated increased tolerance of diclofop-methyl in the selected line."( Recurrent selection with reduced herbicide rates results in the rapid evolution of herbicide resistance in Lolium rigidum.
Neve, P; Powles, S, 2005
)
" Dose-response experiment indicated that Lujiang population was highly resistant to fenoxaprop-p-ethyl (199."( Target-site mechanism of ACCase-inhibitors resistance in American sloughgrass (Beckmannia syzigachne Steud.) from China.
Du, L; Li, L; Liu, W; Wang, J; Yuan, G, 2014
)
" Dose-response experiments showed that the AHSX-1 population has evolved a very high level resistance to fenoxaprop-p-ethyl (RI = 275) and mesosulfuron-methyl (RI = 788)."( Multiple resistance to ACCase and AHAS-inhibiting herbicides in shortawn foxtail (Alopecurus aequalis Sobol.) from China.
Bi, Y; Du, L; Guo, W; Li, Q; Liu, W; Wang, J; Yuan, G; Zhang, C, 2015
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency37.27470.002541.796015,848.9004AID1347395; AID1347398
pregnane X receptorRattus norvegicus (Norway rat)Potency31.62280.025127.9203501.1870AID651751
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency2.11320.001530.607315,848.9004AID1224841
pregnane X nuclear receptorHomo sapiens (human)Potency70.79460.005428.02631,258.9301AID720659
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency34.37620.000627.21521,122.0200AID651741
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Acetyl-CoA carboxylase 1 Rattus norvegicus (Norway rat)IC50 (µMol)40.00000.05300.17880.5900AID30370
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID493458Antimalarial activity against Plasmodium falciparum D102010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Dimeric cyclohexane-1,3-dione oximes inhibit wheat acetyl-CoA carboxylase and show anti-malarial activity.
AID30370Inhibitory concentration against rat heart ACC by the carboxylation of acetyl-CoA with [14C]-HCO3- to form [14C]-malonyl CoA; 18-40 uM2003Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19
Cyclohexanedione herbicides are inhibitors of rat heart acetyl-CoA carboxylase.
AID493460Inhibition of maize ACC2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Dimeric cyclohexane-1,3-dione oximes inhibit wheat acetyl-CoA carboxylase and show anti-malarial activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (16.00)29.6817
2010's13 (52.00)24.3611
2020's8 (32.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]