Compounds > molinate
Page last updated: 2024-12-05

molinate

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

Description

Molinate, a thiocarbamate herbicide, is synthesized via the reaction of methyl chloroformate with N-methyl-N-cyclohexyldithiocarbamic acid. It acts as a pre-emergent and post-emergent herbicide, inhibiting lipid biosynthesis and growth in rice weeds. Molinate is widely used for weed control in rice paddies, but its persistence in the environment and potential for aquatic toxicity have raised concerns. Research on molinate focuses on its degradation pathways, environmental fate, and ecotoxicological effects. Studies aim to understand its impact on aquatic organisms, assess its potential for bioaccumulation, and evaluate the effectiveness of mitigation strategies to minimize its environmental footprint.'

molinate : A member of the class of azepanes that is azepane in which the nitrogen is substituted by an (ethylsulfanyl)carbonyl group, -C(=O)SEt. A thiocarbamate herbicide not approved for use in the U.S. or European Union, it is used control grass weeds in rice paddies. [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 CID16653
CHEMBL ID1865916
CHEBI ID6964
SCHEMBL ID63895
MeSH IDM0054872

Synonyms (78)

Synonym
BIDD:ER0419
1h-azepine-1-carbothioic acid, hexahydro-, s-ethyl ester
NCGC00091443-01
MLS001065581
smr000568482
malerbane giavoni l
s-ethyl hexahydroazepine-1-carbothioate
r-4572
perhydroazepin-1-carbothioate
molinate estrella
jalan
yalan
sakkimol
s-ethyl-n-hexamethylenethiocarbamate
sc 998
higalnate
r 4572
molmate
felan
yulan
epa pesticide chemical code 041402
stauffer r-4,572
s-aethyl-n-hexahydro-1h-azepinthiolcarbamat [german]
caswell no. 444
ethyl 1-hexamethyleneiminecarbothiolate
s-ethyl perhydroazepine-1-thiocarboxylate
einecs 218-661-0
s-ethyl 1-hexamethyleneiminothiocarbamate
s-ethyl hexahydro-1h-azepine-1-carbothioate
hydram
s-ethyl-n,n-hexamethylenethiocarbamate
hsdb 873
brn 1239196
s-ethyl perhydroazepin-1-carbothioate
molinate [bsi:iso]
s-ethyl n,n-hexamethylenethiocarbamate
2212-67-1
molinate
ordram
NCGC00091443-02
s-ethyl azepane-1-carbothioate
NCGC00091443-03
NCGC00091443-04
NCGC00091443-05
HMS3039B07
unii-68n5g08djq
5-20-04-00034 (beilstein handbook reference)
ccris 8083
s-aethyl-n-hexahydro-1h-azepinthiolcarbamat
68n5g08djq ,
cas-2212-67-1
dtxsid6024206 ,
NCGC00254721-01
tox21_201572
tox21_300817
dtxcid204206
NCGC00259121-01
AKOS006230487
FT-0603598
CHEMBL1865916
chebi:6964 ,
molinate [iso]
molinate [hsdb]
molinate [mi]
sc-9908
SCHEMBL63895
s-ethyl n,n-hexamethylenothiocarbamate
s-ethyl perhydroazepine-1-carbothioate
DEDOPGXGGQYYMW-UHFFFAOYSA-N
s-ethyl 1-azepanecarbothioate #
KS-5374
molinate, pestanal(r), analytical standard
molinate 100 microg/ml in cyclohexane
molinate 10 microg/ml in cyclohexane
J-014537
mfcd00055352
AS-13882
Q1943471

Research Excerpts

Overview

Molinate is a thiocarbamate herbicide used worldwide in rice crop protection. Administration of molinate results in reproductive toxicity in male rats. Molinate has been demonstrated to affect reproduction in the rat via alterations in sperm production.

ExcerptReferenceRelevance
"Molinate is a thiocarbamate herbicide used worldwide in rice crop protection. "( Microbial degradation of the herbicide molinate by defined cultures and in the environment.
Lopes, AR; Manaia, CM; Nunes, OC, 2013)		2.1
"Molinate is a pesticide widely used, both in space and time, for weed control in rice paddies. "( Assessment of combined electro-nanoremediation of molinate contaminated soil.
Dias-Ferreira, C; Fan, G; Gomes, HI; Mateus, EP; Ribeiro, AB, 2014)		2.1
"Molinate is a recalcitrant thiocarbamate used to control grass weeds in rice fields. "( Structure-guided engineering of molinate hydrolase for the degradation of thiocarbamate pesticides.
Duarte, M; Ferreira-da-Silva, F; Gales, L; Leite, JP; Matias, PM; Nunes, OC; Paiva, AM, 2015)		2.14
"Molinate is a thiocarbamate herbicide used as a pre-emergent in rice patty fields. "( Relative inhibitory potency of molinate and metabolites with aldehyde dehydrogenase 2: implications for the mechanism of enzyme inhibition.
Allen, EM; Anderson, DG; Doorn, JA; Florang, VR; Hurley, TD; Khanna, M, 2010)		2.09
"Molinate is a preemergent herbicide that has been demonstrated to affect reproduction in the rat via alterations in sperm production. "( Mode of action: reduction of testosterone availability--molinate-induced inhibition of spermatogenesis.
Cummings, A; Kavlock, R, )		1.82
"Molinate is a thiocarbamate herbicide widely used in rice culture. "( Testicular toxicity of molinate in the rat: metabolic activation via sulfoxidation.
Hess, RA; Jewell, WT; Miller, MG, 1998)		2.05
"Molinate is a thiocarbamate herbicide used on rice. "( Molinate: rodent reproductive toxicity and its relevance to humans--a review.
Ellis, MK; Foster, JR; Tomenson, JA; Wickramaratne, GA, 1998)		3.19
"Molinate is a thiocarbamate herbicide used for weed control in rice fields. "( An assessment of fertility in male workers exposed to molinate.
Barraj, L; Cockett, AT; Francis, M; McCusker, J; Northrop, HL; Pastoor, TP; Taves, DR; Tomenson, JA; Wickramaratne, GA, 1999)		1.99
"Molinate is a thiocarbamate herbicide used in the rice industry for over 25 years, and regulatory reports have shown that administration of molinate results in reproductive toxicity in male rats. "( Identification of a S-hexahydro-1H-azepine-1-carbonyl adduct produced by molinate on rat hemoglobin beta(2) and beta(3) chains in vivo.
Amarnath, K; Valentine, HS; Valentine, WM; Zimmerman, LJ, 2002)		1.99

Effects

ExcerptReferenceRelevance
"Molinate has been widely used as a pre-emergent herbicide in the rice fields of California's Central Valley. "( Development of PBPK model of molinate and molinate sulfoxide in rats and humans.
Campbell, A, 2009)		2.09

Treatment

Molinate treatment caused a marked inhibition of nonspecific esterase activity in both liver and testis. Both thiocarbamate herbicides increased significantly SCE frequency.

ExcerptReferenceRelevance
"Molinate treatment caused a marked inhibition of nonspecific esterase activity in both liver and testis."( Identification of a carboxylesterase as the major protein bound by molinate.
Jewell, WT; Miller, MG, 1998)		1.26
"Molinate and butylate treatments for 4 h of Vicia faba root tip meristems, showed that both thiocarbamate herbicides increased significantly SCE frequency. "( In vivo and in vitro promutagen activation by Vicia faba of thiocarbamate herbicides molinate and butylate to products inducing sister chromatid exchanges in human lymphocyte cultures.
Calderón-Segura, ME; Espinosa-Ramírez, M; Gómez-Arroyo, S; Villalobos-Pietrini, R, 1999)		1.97

Toxicity

ExcerptReferenceRelevance
" Moreover, molinate is metabolized readily by both liver and testis microsomal enzymes, suggesting that the molinate toxic metabolite could be formed in the testis in close proximity to its site of action."( Testicular toxicity of molinate in the rat: metabolic activation via sulfoxidation.
Hess, RA; Jewell, WT; Miller, MG, 1998)		1
" During the evaluation of the compound for regulatory compliance, an adverse effect on male reproduction in rats was observed."( Molinate: rodent reproductive toxicity and its relevance to humans--a review.
Ellis, MK; Foster, JR; Tomenson, JA; Wickramaratne, GA, 1998)		1.74
" Results showed that toxic concentrations (0."( Comparative toxicity of bentazon and molinate on growth, photosynthetic pigments, photosynthesis, and respiration of the Portuguese ricefield cyanobacterium Nostoc muscorum.
Fernández-Valiente, E; Galhano, V; Gomes-Laranjo, J; Peixoto, F, 2010)		0.63

Pharmacokinetics

ExcerptReferenceRelevance
" Adjusted animal biomonitoring equivalents for molinate and its primary sulfoxide from animal studies were scaled to human biomonitoring equivalents using known species allometric scaling factors and human metabolic data with a simple physiologically based pharmacokinetic (PBPK) model."( Human plasma concentrations of herbicidal carbamate molinate extrapolated from the pharmacokinetics established in in vivo experiments with chimeric mice with humanized liver and physiologically based pharmacokinetic modeling.
Murayama, N; Nishiyama, S; Shimizu, M; Suemizu, H; Yamashita, M; Yamazaki, H, 2014)		0.91

Bioavailability

The toxicity and bioavailability of molinate to Vibrio fischeri (Microtox((R))) were determined in both laboratory and river water in the absence and presence of sediment after 0, 24, 48, 72 and 96-h exposure. The herbicides atrazine and molinate reduced the bioavailability to five Australian freshwater organisms.

ExcerptReferenceRelevance
" Although there have been some studies on the toxicity of herbicides to aquatic organisms using laboratory or natural water, information on the effect of sediments, suspended particulates, and dissolved organic matter on their bioavailability is quite limited."( Toxicity of atrazine and molinate to the cladoceran Daphnia carinata and the effect of river water and bottom sediment on their bioavailability.
Lim, RP; Phyu, YL; Warne, MS, 2004)		0.63
"The toxicity and bioavailability of molinate to Vibrio fischeri (Microtox((R))) were determined in both laboratory and river water in the absence and presence of sediment after 0, 24, 48, 72 and 96-h exposure."( Effect of river water, sediment and time on the toxicity and bioavailability of molinate to the marine bacterium Vibrio fischeri (Microtox).
Lim, RP; Phyu, YL; St J Warne, M, 2005)		0.83
"05) reduced the bioavailability of the herbicides atrazine and molinate to five Australian freshwater organisms."( Assessing the biological relevance of exposing freshwater organisms to atrazine and molinate in environmentally realistic exposure test systems.
Lim, RP; Phyu, YL; St J Warne, M, 2008)		0.81

Dosage Studied

Previous work demonstrated an in vivo decrease in liver aldehyde dehydrogenase (ALDH) activity in rats treated with molinate and motor function deficits in dogs dosed chronically with this compound. Rats were dosed intraperitoneally with Molinate as a function of exposure duration.

ExcerptRelevanceReference
"The potential effects that the thiocarbamate herbicide Ordram has on the immune system of mice was evaluated following 12 days of acute dosing by oral gavage."( Evaluation of immune function in mice exposed to Ordram.
Luebke, RW; Riddle, MM; Rogers, RR; Rowe, DG; Smialowicz, RJ, 1985)		0.27
" Following dermal dosing the ratio of trans/cis cyclopropane acids is approximately 1:1, compared to 2:1 after oral administration."( Biological monitoring for pesticide exposure--the role of human volunteer studies.
Batten, PL; Chester, G; Marsh, JR; Wilkes, MF; Woollen, BH, 1993)		0.29
" Rats were dosed intraperitoneally with molinate as a function of exposure duration."( Identification of a S-hexahydro-1H-azepine-1-carbonyl adduct produced by molinate on rat hemoglobin beta(2) and beta(3) chains in vivo.
Amarnath, K; Valentine, HS; Valentine, WM; Zimmerman, LJ, 2002)		0.81
" Previous work demonstrated an in vivo decrease in liver aldehyde dehydrogenase (ALDH) activity in rats treated with molinate and motor function deficits in dogs dosed chronically with this compound."( Relative inhibitory potency of molinate and metabolites with aldehyde dehydrogenase 2: implications for the mechanism of enzyme inhibition.
Allen, EM; Anderson, DG; Doorn, JA; Florang, VR; Hurley, TD; Khanna, M, 2010)		0.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antispermatogenic agentAn agent that destroy spermatozoa in the male genitalia and block spermatogenesis.
herbicideA substance used to destroy plant pests.
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
azepanes
monothiocarbamic esterA thiocarbamic ester formally derived from a monothiocarbamic acid.
[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)Potency9.46620.003245.467312,589.2998AID2517
AR proteinHomo sapiens (human)Potency0.00130.000221.22318,912.5098AID588516
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency26.53030.001022.650876.6163AID1224838
progesterone receptorHomo sapiens (human)Potency29.76750.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency33.62130.003041.611522,387.1992AID1159552; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency21.25300.000817.505159.3239AID1159527
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.25120.000229.305416,493.5996AID588513
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency67.70690.000627.21521,122.0200AID651741
gemininHomo sapiens (human)Potency0.00730.004611.374133.4983AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1100793Binding affinity to SafBP receptor in Zea mays (maize) seedlings by [3H]Saf(R-29148) binding assay2000Journal of agricultural and food chemistry, Mar, Volume: 48, Issue:3
Comparative three-dimensional quantitative structure-activity relationship study of safeners and herbicides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (92)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (8.70)18.7374
1990's21 (22.83)18.2507
2000's37 (40.22)29.6817
2010's23 (25.00)24.3611
2020's3 (3.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.93

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 Index36.93 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other96 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		2.0810amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
ammonium hydroxide
azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.		2.0510azane;
gas molecular entity;
mononuclear parent hydride		EC 3.5.1.4 (amidase) inhibitor;
metabolite;
mouse metabolite;
neurotoxin;
NMR chemical shift reference compound;
nucleophilic reagent;
refrigerant
carbamates
[no description available]		5.48210amino-acid anion
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		2.0510monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
nitric acid
Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.		2.0310nitrogen oxoacidprotic solvent;
reagent
acetochlor
acetochlor : A monocarboxylic acid amide that is N-phenylacetamide carrying an ethyl and a methyl group at positions 2 and 6 respectively on the benzene ring while one of the methyl hydrogens as well as the hydrogen attached to the nitrogen atom have been replaced by a chloro and an ethoxymethyl group respectively.		210aromatic amide;
monocarboxylic acid amide;
organochlorine compound		environmental contaminant;
herbicide;
xenobiotic
alachlor
alachlor : An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.		2.3920aromatic amide;
monocarboxylic acid amide;
organochlorine compound		environmental contaminant;
herbicide;
xenobiotic
atrazine
[no description available]		3.470chloro-1,3,5-triazine;
diamino-1,3,5-triazine		environmental contaminant;
herbicide;
xenobiotic
bentazone
bentazone: RN given refers to parent cpd; structure. bentazone : A benzothiadiazine that is 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide substituted by an isopropyl group at position 3.		2.730benzothiadiazineenvironmental contaminant;
herbicide;
xenobiotic
benzo(a)pyrene
Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.		2.0310ortho- and peri-fused polycyclic arenecarcinogenic agent;
mouse metabolite
carbofuran
Carbofuran: A cholinesterase inhibitor that is used as a systemic insecticide, an acaricide, and nematocide. (From Merck Index, 11th ed)		3.49201-benzofurans;
carbamate ester		acaricide;
agrochemical;
avicide;
carbamate insecticide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nematicide
chlorpyrifos
Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.		7.0510chloropyridine;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
insecticide;
xenobiotic
cypermethrin
cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.		2.3820aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organochlorine compound		agrochemical;
molluscicide;
pyrethroid ester acaricide;
pyrethroid ester insecticide
dichlorvos
Dichlorvos: An organophosphorus insecticide that inhibits ACETYLCHOLINESTERASE.. dichlorvos : An alkenyl phosphate that is the 2,2-dichloroethenyl ester of dimethyl phosphate.		210alkenyl phosphate;
dialkyl phosphate;
organochlorine acaricide;
organophosphate insecticide		anthelminthic drug;
antibacterial agent;
antifungal agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor
disulfoton
Disulfoton: An organothiophosphate insecticide.. disulfoton : An organic thiophosphate that is the diethyl ester of S-[2-(ethylsulfanyl)ethyl] dihydrogen phosphorodithioate.		1.9910organic thiophosphate;
organothiophosphate insecticide		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor
diuron
Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.		7.47203-(3,4-substituted-phenyl)-1,1-dimethylurea;
dichlorobenzene		environmental contaminant;
mitochondrial respiratory-chain inhibitor;
photosystem-II inhibitor;
urea herbicide;
xenobiotic
fenthion
Fenthion: Potent cholinesterase inhibitor used as an insecticide and acaricide.. fenthion : An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen atom of the hydroxy group is replaced by a 3-methyl-4-(methylsulfanyl)phenyl group. It exhibits acaricidal and insecticidal activities.		1.9910organic thiophosphateacaricide;
agrochemical;
avicide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
insecticide
hexobarbital
Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.		6.9710barbiturates
methyl parathion
Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.		3.0910C-nitro compound;
organic thiophosphate;
organothiophosphate insecticide		acaricide;
agrochemical;
antifungal agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
genotoxin
metolachlor
metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.		210aromatic amide;
benzenes;
ether;
organochlorine compound
prometone
prometone: structure. prometon : A methoxy-1,3,5-triazine that is 6-methoxy-1,3,5-triazine-2,4-diamine in which the one of the hydrogens of each amino group is substituted by an isopropyl group.		2.0410diamino-1,3,5-triazine;
methoxy-1,3,5-triazine		environmental contaminant;
herbicide;
xenobiotic
propachlor
propachlor: structure. propachlor : An anilide that consists of 2-chloroacetanilide bearing an N-isopropyl substituent.		210anilide;
monocarboxylic acid amide;
organochlorine compound		environmental contaminant;
herbicide;
xenobiotic
propanil
Propanil: A chlorinated anilide that is used as an herbicide.. propanil : An anilide resulting from the formal condensation of the carboxy group of propanoic acid with the amino group of 3,4-dichloroaniline. It is a herbicide used for the treatment of numerous grasses and broad-leaved weeds in rice, potatoes, and wheat.		2.3820anilide;
dichlorobenzene		herbicide
safrole
Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.		2.6930benzodioxolesflavouring agent;
insecticide;
metabolite;
plant metabolite
triallate
Triallate: A pre-emergence, selective herbicide for the control of wild oats in various crops.		210tertiary amine
trifluralin
Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.		2.4320(trifluoromethyl)benzenes;
C-nitro compound;
substituted aniline		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
aniline
[no description available]		7.0210anilines;
primary arylamine
carbaryl
Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.		6.9510carbamate ester;
naphthalenes		acaricide;
agrochemical;
carbamate insecticide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant growth retardant
ethanethiol
ethanethiol: RN given refers to parent cpd; structure. ethanethiol : An alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks.		2.0410alkanethiolrodenticide
michler's ketone
[no description available]		2.0310benzophenones
cdaa
CDAA: structure		210tertiary carboxamide
2-methyl-4-chlorophenoxyacetic acid
2-Methyl-4-chlorophenoxyacetic Acid: A powerful herbicide used as a selective weed killer.. (4-chloro-2-methylphenoxy)acetic acid : A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.		3.0910chlorophenoxyacetic acid;
monochlorobenzenes		environmental contaminant;
phenoxy herbicide;
synthetic auxin
2,4-di-tert-butylphenol
2,4-di-tert-butylphenol: structure given in first source. 2,4-di-tert-butylphenol : A member of the class of phenols carrying two tert-butyl substituents at positions 2 and 4.		2.0310alkylbenzene;
phenols		antioxidant;
bacterial metabolite;
marine metabolite
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		1.9910mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
sulfoxide
sulfoxide: synergistic insecticide for use with pyrethrum, allethrin, rotenone, ryania, etc.; RN given refers to parent cpd; structure. sulfoxide : An organosulfur compound having the structure R2S=O or R2C=S=O (R =/= H).		2.6930benzodioxoles
2,4-dinitrotoluene
2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.		2.0410dinitrotoluene
cyclonite
cyclonite: explosive & convulsant; structure. 1,3,5-trinitro-1,3,5-triazinane : An N-nitro compound that is 1,3,5-triazinane in which all three of the hydrogens attached to the nitrogens have been replaced by nitro groups. It is widely used in both industrial and military explosives.		2.04101,3,5-triazinanes;
N-nitro compound		explosive
captan
Captan: One of the phthalimide fungicides.. captan : A dicarboximide that is 3a,4,7,7a-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethyl group. A non-systemic fungicide introduced in the 1950s, it is widely used for the control of fungal diseases in fruits, vegetables, and ornamental crops.		1.9810isoindoles;
organochlorine compound;
organosulfur compound;
phthalimide fungicide		antifungal agrochemical
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		2.9640isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
linuron
Linuron: A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed). linuron : A member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3.		2.0410dichlorobenzene;
phenylureas		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
2,6-dinitrotoluene
2,6-dinitrotoluene: RN given refers to cpd with specified locants for nitrogen moieties. 2,6-dinitrotoluene : A dinitrotoluene carrying nitro substituents at positions 2 and 6.		2.0410dinitrotoluenegenotoxin
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		1.9510acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
eptc
EPTC: minor descriptor (72-82); online & Index Medicus search HERBICIDES, CARBAMATE (72-82)		2.4220tertiary amine
ametryne
ametryne: minor descriptor (72-83); on-line & Index Medicus search HERBICIDES, TRIAZINE (75-83) & HERBICIDES (72-74) & TRIAZINES (72-74); RN given refers to unlabeled cpd; structure. ametryn : A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by an ethylamino and an isopropylamino group at positions 4 and 6 respectively.		2.0410diamino-1,3,5-triazine;
methylthio-1,3,5-triazine		environmental contaminant;
herbicide
pebulate
pebulate: structure		210tertiary amine
cycloate
[no description available]		210primary aliphatic amine
s,n,n'-tripropylthiocarbamate
Reward: An object or a situation that can serve to reinforce a response, to satisfy a motive, or to afford pleasure.. vernolate : A monounsaturated fatty acid anion that is the conjugate base of vernolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.		2.3920tertiary amine
butylate
butylate: RN in Chemline for carbamothioic-(14)C-labeled cpd: 61772-76-7		2.3920tertiary amine
mercury
Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.		7.0210elemental mercury;
zinc group element atom		neurotoxin
titanium
Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.		2.110titanium group element atom
ozone
Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.		2.0410elemental molecule;
gas molecular entity;
reactive oxygen species;
triatomic oxygen		antiseptic drug;
disinfectant;
electrophilic reagent;
greenhouse gas;
mutagen;
oxidising agent;
tracer
titanium dioxide
titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.		2.110titanium oxidesfood colouring
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.0810glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
benthiocarb
Saturn: The sixth planet in order from the sun. It is one of the five outer planets of the solar system. Its twelve natural satellites include Phoebe and Titan.		4.3660monochlorobenzenes;
monothiocarbamic ester
dichlormid
dichlormid: antidote for EPTC injury in corn; structure		210tertiary carboxamide
isoprothiolane
isoprothiolane: structure given in first source. isoprothiolane : A malonate ester that is diisopropyl malonate in which the two methylene hydrogens at position 2 are replaced by a 1,3-dithiolan-2-ylidene group. An insecticide and fungicide used to control a range of diseases including Pyricularia oryzae, Helminthosporium sigmoideum and Fusarium nivale.		1.9910dithiolanes;
isopropyl ester;
malonate ester		antifungal agrochemical;
environmental contaminant;
insecticide;
phospholipid biosynthesis inhibitor
fluazifop-butyl
fluazifop-butyl: RN given for cpd without isomeric designation. fluazifop-butyl : A racemate that is the butyl ester of fluazifop. It is used as a post-emergence herbicide for the control grass weeds in various broad-leaved crops.. butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate : A carboxylic ester resulting from the formal condensation of the carboxy group 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid with the hydroxy group of butan-1-ol.		1.9810aromatic ether;
carboxylic ester;
organofluorine compound;
pyridines
clomazone
clomazone: an herbicide. clomazone : An isoxazolidinone that is 1,2-oxazolidin-3-one substituted by a 2-chlorobenzyl group at position 2 and two methyl groups at position 4.		2.9640isoxazolidinone;
monochlorobenzenes		agrochemical;
carotenoid biosynthesis inhibitor;
environmental contaminant;
herbicide;
xenobiotic
methyl bensulfuron
methyl bensulfuron: RN given refers to parent cpds. bensulfuron-methyl : The methyl ester of bensulfuron. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of both annual and perennial weeds in crops, particularly wheat and rice. It is not licensed for use within the UK.		3.0910aromatic ether;
methyl ester;
N-sulfonylurea;
pyrimidines		agrochemical;
EC 2.2.1.6 (acetolactate synthase) inhibitor;
herbicide
r 29148
R-29148 : A member of the class of oxazolidines that is 1,3-oxazolidine which is substituted by two methyl groups, dichloroacetyl group and a methyl group at positions 2, 3 and 5, respectively. It is a herbicide safener.		210organochlorine compound;
oxazolidines;
tertiary carboxamide		herbicide safener
benoxacor
benoxacor: a herbicide safener that protects corn from injury by metachlor		210benzoxazine
oxazolidin-2-one
Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.		2.9640carbamate ester;
oxazolidinone		metabolite
di-n-butyl-2,2-dichlorovinyl phosphate
[no description available]		210
glucuronic acid
Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.		1.9710D-glucuronic acidalgal metabolite
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		7.0610cobalt group element atom;
metal allergen		micronutrient
s-methyl diethylthiocarbamate
S-methyl diethylthiocarbamate: structure in first source		2.4420
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		2.0410oxygen hydride;
oxygen radical;
reactive oxygen species
fenton's reagent
Fenton's reagent: used for oxidizing sugars & alcohols		2.110
retinol
Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).		2.0710retinol;
vitamin A		human metabolite;
mouse metabolite;
plant metabolite
retinaldehyde
Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.		2.0710retinal;
vitamin A		gap junctional intercellular communication inhibitor;
human metabolite;
mouse metabolite
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.0110chalcogen;
nonmetal atom		macronutrient
chlorophyll a
Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.		2.4220chlorophyll;
methyl ester		cofactor
chitosan
[no description available]		2.1310
pyrethrins
[no description available]		2.3820
pheophytin a
pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S*,11S*),4beta,21beta))-isomer		2.4220
dinitrobenzenes
Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.5420
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		07.5420
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.7230
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.0210
Sterility, Male
[description not available]		0210
Infertility, Male
The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.		0210
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9610
Delayed Hypersensitivity
[description not available]		01.9610