imazethapyr profile

Imazethapyr is a synthetic herbicide that belongs to the imidazolinone chemical class. It is widely used for pre-emergent and post-emergent weed control in various crops, including corn, soybeans, and wheat. Imazethapyr inhibits the enzyme acetohydroxyacid synthase (AHAS), which is essential for the biosynthesis of branched-chain amino acids, leading to disruption of plant growth and development. This mode of action makes imazethapyr effective against a broad spectrum of weeds, including grasses and broadleaf plants. Imazethapyr is known for its persistence in the soil, providing long-lasting weed control. However, its persistence can also lead to environmental concerns, such as potential leaching into groundwater. The herbicide has been the subject of research to evaluate its potential for weed control in different crop systems, its environmental fate, and its effects on non-target organisms.'

imazethapyr: do not confuse with imazapyr, which is the 5-desethyl analog of imazethapyr [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	54740
CHEMBL ID	1903400
CHEBI ID	82022
SCHEMBL ID	18516
MeSH ID	M0246881

Synonym
3-pyridinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl]-5-ethyl-
5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-1h-imidazol-2-yl)pyridine-3-carboxylic acid
imazethapyr
LS-10985
(rs)-5-ethyl-2(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid
ac 263,499
(+-)-2-(4,5-dihydro-4-methyl-4(1-methylethyl)-5-oxo-1h-imidazol-2yl)-5-ethyl-3-pyridinecarboxylic acid
imazethapyr [ansi:bsi:iso]
epa pesticide chemical code 128922
cl 263499
hsdb 6678
pivot
3-pyridinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-, (+-)-
2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid
5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1h-imidazol-2-yl)nicotinic acid
81335-77-5
pursuit
NCGC00168319-01
XVOKUMIPKHGGTN-UHFFFAOYSA-N
2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-5-ethylpyridine-3-carboxylic acid
5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid
5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid
5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-3-pyridinecarboxylic acid
A840101
5-ethyl-2-(4-methyl-5-oxidanylidene-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid
AKOS004910000
NCGC00168319-02
3-pyridinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1- methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-
C18865
72t2in94i4 ,
unii-72t2in94i4
3-pyridinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-
dtxsid3024287 ,
cas-81335-77-5
dtxcid004287
NCGC00258891-01
tox21_201339
NCGC00254914-01
tox21_301012
FT-0630888
chebi:82022 ,
CHEMBL1903400
fabian
5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) nicotinic acid
2-(4,5-dihydro-4-methyl-4(1-methylethyl)-5-oxo-1h- imidazol-2yl)-5-ethyl-3-pyridinecarboxylic acid, (+/-)-
5-ethyl-2(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2- yl)nicotinic acid, (rs)-
cl-263499
imazethapyr [mi]
2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol- 2-yl)-5-ethyl-3-pyridinecarboxylic acid
imazethapyr [hsdb]
5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1h-imidazol-2-yl)nicotinic acid, (+/-)-
3-pyridinecarboxylic acid, 2-(4,5-dihydro-4-methyl-4-(1- methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-, (+/-)-
imazethapyr, (+/-)-
ac-263499
imazethapyr [iso]
SCHEMBL18516
imazethapyr, pestanal(r), analytical standard
imazethapyr 10 microg/ml in acetonitrile
mfcd00274561
Q22808273
F82542
HY-133188
5-ethyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1h-imidazol-2-yl]pyridine-3-carboxylic acid
CS-0113200

Research Excerpts

Overview

Imazethapyr (IM) is an imidazolinone herbicide that is currently used for broad-spectrum weed control in soybean and other legume crops. It inhibits the synthesis of branched-chain amino acids (BCAAs)

Excerpt	Reference	Relevance
"Imazethapyr (IM) is an acetolactate synthase (ALS)-inhibiting herbicide that has been widely used in recent years. "	( Effects of imazethapyr spraying on plant growth and leaf surface microbial communities in Arabidopsis thaliana. Ke, M; Li, Y; Liu, W; Lu, T; Pan, X; Qian, H; Zhang, Z; Zhu, Y, 2019)	2.35
"Imazethapyr (IM) is a chiral herbicide with two enantiomers (R-IM and S-IM). "	( Enantioselective effects of imazethapyr on Arabidopsis thaliana root exudates and rhizosphere microbes. Li, Y; Liu, W; Lu, T; Pan, X; Qian, H; Qu, Q; Xu, N; Zhang, Z; Zhao, Q, 2020)	2.29
"Imazethapyr (IM) is a widely used acetolactate synthase-inhibiting chiral herbicide. "	( Enantioselective effects of imazethapyr residues on Arabidopsis thaliana metabolic profile and phyllosphere microbial communities. Ke, M; Li, Y; Liu, W; Pan, X; Qian, H; Qu, Q; Yuan, W; Zhao, Q, 2020)	2.29
"Imazethapyr (IMZT) is a typical chiral pesticide with two enantiomers with the R-IMZT having the main herbicidal activity. "	( Enantioselectivity effects of imazethapyr enantiomers to metabolic responses in mice. Meng, Z; Sheng, J; Tian, S; Yan, S; Yao, C; Zhou, Z; Zhu, W, 2020)	2.29
"Imazethapyr (IM) is an imidazolinone herbicide that is currently used for broad-spectrum weed control in soybean and other legume crops. "	( Determination of genotoxic effects of Imazethapyr herbicide in Allium cepa root cells by mitotic activity, chromosome aberration, and comet assay. Ciğerci, İH; Liman, R; Öztürk, NS, 2015)	2.13
"Imazethapyr (IM) is a widely used chiral herbicide that inhibits the synthesis of branched-chain amino acids (BCAAs). "	( Analyzing Arabidopsis thaliana root proteome provides insights into the molecular bases of enantioselective imazethapyr toxicity. Ding, H; Fu, Z; Lavoie, M; Li, Y; Liu, W; Lu, H; Qian, H, 2015)	2.07
"Imazethapyr (IM) is an acetolactate synthase (ALS)-inhibiting chiral herbicide that has been widely used in recent years with racemate."	( Enantioselective phytotoxicity of the herbicide imazethapyr on the response of the antioxidant system and starch metabolism in Arabidopsis thaliana. Fu, Z; Han, X; Liu, W; Lu, T; Peng, X; Qian, H, 2011)	1.35
"Imazethapyr (IM) is a chiral herbicide and a widely used racemic mixture. "	( Enantioselective phytotoxicity of the herbicide imazethapyr and its effect on rice physiology and gene transcription. Chen, X; Fu, Z; Hu, H; Liu, W; Lu, T; Qian, H; Wang, R; Ye, H, 2011)	2.07
"Imazethapyr (IM) is a chiral herbicide with reported enantioselective biological activities between its enantiomers. "	( Imazethapyr enantioselectively affects chlorophyll synthesis and photosynthesis in Arabidopsis thaliana. Fu, Z; Han, X; Qian, H; Sun, L; Sun, Z; Zhang, Q, 2013)	3.28
"Imazethapyr is a herbicide which acts on the enzyme ALS, the first common enzyme in the biosynthetic pathway of valine, leucine and isoleucine."	( Cross resistance to ALS-inhibiting herbicides in Euphorbia heterophylla L. biotypes resistant to imazethapyr. De Prado, R; Osuna, MD; Plaza, G, 2003)	1.26

Toxicity

Excerpt	Reference	Relevance
" In addition, a toxic effect of the applied pesticides on the nodulation and root growth of the tested plants was observed."	( Pesticide side effect on the symbiotic efficiency and nitrogenase activity of Rhizobiaceae bacteria family. Klama, J; Niewiadomska, A, 2005)	0.33
" IM also had adverse effects on cell organelles, such as statocytes, mitochondria, dictyosomes, and endoplasmic reticulum in maize roots."	( Enantioselectivity in the phytotoxicity of herbicide imazethapyr. Liu, W; Xu, C; Zhang, Y; Zhou, Q, 2009)	0.6
" IM is thought to exert its toxic effects on amino acid synthesis mainly through inhibition of acetolactate synthase activity, but little is known about the potential effects of IM on other key biochemical pathways."	( Analyzing Arabidopsis thaliana root proteome provides insights into the molecular bases of enantioselective imazethapyr toxicity. Ding, H; Fu, Z; Lavoie, M; Li, Y; Liu, W; Lu, H; Qian, H, 2015)	0.63
" The Verosil(®) formulation was highly toxic to the non-target green alga (median effective concentration (EC50) = 1."	( Phytotoxicity and genotoxicity assessment of imazethapyr herbicide using a battery of bioassays. Fassiano, AV; Juárez, ÁB; Magdaleno, A; March, H; Moretton, J; Peralta Gavensky, M; Ríos de Molina, MC; Santos, M, 2015)	0.68
"Effectively controlling target organisms while reducing the adverse effects of pesticides on non-target organisms is a crucial scientific inquiry and challenge in pesticide ecotoxicology research."	( Phytotoxicity alleviation of imazethapyr to non-target plant wheat: active regulation between auxin and DIMBOA. Chen, H; Huang, J; Li, J; Shen, C; Wen, Y, 2023)	1.2

Bioavailability

Excerpt	Reference	Relevance
" Therefore, enantiomeric differences should be considered when evaluating the bioavailability of the herbicide IM."	( Enantioselectivity in the phytotoxicity of herbicide imazethapyr. Liu, W; Xu, C; Zhang, Y; Zhou, Q, 2009)	0.6

Dosage Studied

We performed in vivo dose-response assays, and confirmed that both populations had strong resistance to chlorimuron-ethyl, diclosulam and imazethapyr.

Excerpt	Relevance	Reference
" 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)	0.33
" Whole-plant dose-response studies showed that the purified subpopulation was highly resistant to chlorsulfuron, metosulam and imazamox, with LD₅₀ or GR₅₀ R/S ratio of > 1024, > 512 and > 137 respectively."	( A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides. Friesen, S; Han, H; Li, M; Powles, SB; Purba, E; Walsh, M; Yu, Q, 2012)	0.38
" In vivo AHAS assay and the comparison of parameters from dose-response curves have been used as a valid tool for comparing sunflower lines and hybrids differing in imidazolinone resistance."	( Acetohydroxyacid synthase (AHAS) in vivo assay for screening imidazolinone-resistance in sunflower (Helianthus annuus L.). Breccia, G; Gil, M; Nestares, G; Picardi, L; Vega, T; Zorzoli, R, 2012)	0.38
"We performed in vivo dose-response assays, and confirmed that both populations had strong resistance to chlorimuron-ethyl, diclosulam and imazethapyr when compared with a susceptible population (S)."	( Target-site resistance to acetolactate synthase (ALS)-inhibiting herbicides in Amaranthus palmeri from Argentina. Larran, AS; Lieber, L; Palmieri, VE; Permingeat, HR; Perotti, VE; Tuesca, D, 2017)	0.66
" Whole-plant dose-response tests showed that the SX population exhibited 11."	( The basis of resistance mechanism to mesosulfuron-methyl in Tausch's goatgrass (Aegilops tauschii Coss.). Huang, H; Huang, Z; Sui, B; Wei, S; Zhang, C, 2019)	0.51

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
aromatic carboxylic acid	Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.
pyridines	Any organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
[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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	0.0968	0.0060	38.0041	19,952.5996	AID1159521
AR protein	Homo sapiens (human)	Potency	0.7943	0.0002	21.2231	8,912.5098	AID588516
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	54.8805	0.0002	14.3764	60.0339	AID720691
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	17.3547	0.0008	17.5051	59.3239	AID1159531
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	61.5769	0.0002	29.3054	16,493.5996	AID743078
Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)	Potency	39.8107	0.0158	23.5273	44.6684	AID651778
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Acetolactate synthase	Raphanus raphanistrum	IC50 (µMol)	334.2353	0.0070	2.9264	6.8380	AID1112484; AID1112486; AID1112487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
negative regulation of cytokine production involved in inflammatory response	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of reactive oxygen species biosynthetic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of hepatocyte apoptotic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of signaling receptor activity	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of ATP biosynthetic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of transformation of host cell by virus	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
response to hypoxia	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
gluconeogenesis	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
heart development	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
response to nutrient	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
epidermis development	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
cellular response to starvation	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
regulation of cellular ketone metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of macrophage derived foam cell differentiation	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of cholesterol storage	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of sequestering of triglyceride	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
regulation of fatty acid metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
intracellular receptor signaling pathway	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of fatty acid beta-oxidation	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of appetite	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
response to insulin	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
circadian regulation of gene expression	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
behavioral response to nicotine	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
wound healing	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
lipoprotein metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
regulation of circadian rhythm	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
steroid hormone mediated signaling pathway	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
response to ethanol	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of gluconeogenesis	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of blood pressure	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of glycolytic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of DNA-templated transcription	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
nitric oxide metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of fatty acid oxidation	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of lipid biosynthetic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of inflammatory response	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of cell growth involved in cardiac muscle cell development	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
enamel mineralization	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
cellular response to fructose stimulus	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of miRNA transcription	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
negative regulation of leukocyte cell-cell adhesion	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
regulation of fatty acid transport	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
hormone-mediated signaling pathway	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
fatty acid metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
positive regulation of fatty acid metabolic process	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
cell differentiation	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription activator activity	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
transcription coactivator binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription factor activity	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
nuclear steroid receptor activity	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
nuclear receptor activity	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
protein binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
zinc ion binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
lipid binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
phosphatase binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
protein domain specific binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
mitogen-activated protein kinase kinase kinase binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
ubiquitin conjugating enzyme binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
sequence-specific DNA binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
protein-containing complex binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
NFAT protein binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
MDM2/MDM4 family protein binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
DNA-binding transcription factor binding	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
nucleoplasm	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
chromatin	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
nucleus	Peroxisome proliferator-activated receptor alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay ID	Title	Year	Journal	Article
AID1112493	Herbicidal activity against two to three leaf stage ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant assessed as reduction in survival measured 3 weeks after compound treatment	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1112492	Herbicidal activity against two to three leaf stage ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish) assessed as reduction in survival measured 3 weeks after compound treatment	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1112484	Inhibition of ALS in ALS-herbicide-susceptible Raphanus raphanistrum WARR33 (wild radish)	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1081408	Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 400 ug/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1080558	Phytotoxicity in Zea mays (maize) assessed as shoot height at 800 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1081407	Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 800 ug/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1081412	Inhibition of in vitro ALS activity of Zea mays (maize) at 200 ug/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1080559	Phytotoxicity in Zea mays (maize) assessed as total root length measured per plant at 100 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080563	Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 800 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1112490	Herbicidal activity against two to three leaf stage ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant assessed as reduction in dry weight of above-ground biomass measured 3 weeks after compound treatment	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1080564	Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 200 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1082416	Induction of caffeic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080568	Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 800 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1082407	Induction of p-coumaric acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080570	Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 100 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1081411	Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 100 ug/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1082400	Induction of DAHPS enzyme expression in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by immunoblot	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080560	Phytotoxicity in Zea mays (maize) assessed as shoot height at 200 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080562	Phytotoxicity in Zea mays (maize) assessed as shoot height at 100 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080569	Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 200 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080567	Phytotoxicity in Zea mays (maize) assessed as shoot dry weight assessed per 10 plants at 400 ug/L measured 5 days post compound treatment (Rvb = 101.2 +/- 4.5 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1081409	Inhibition of in vitro ALS activity in first leaf of the plant grew out Zea mays (maize) seedlings measured at 520 OD/ mg of protein/hr at 200 ug/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1080557	Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 200 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080551	Reduction in root tips in Zea mays (maize) seedlings at 100 to 800 ug/L	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1082414	Induction of sinapic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080566	Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 100 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1082405	Induction of ferulic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1081410	Inhibition of in vitro ALS activity of Zea mays (maize) at 25 mg/L at 37 degC	2010	Journal of agricultural and food chemistry, Apr-14, Volume: 58, Issue:7	Molecular mechanism of enantioselective inhibition of acetolactate synthase by imazethapyr enantiomers.
AID1082386	Increase in lignin content in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 10 days post onset of compound treatment	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080565	Phytotoxicity in Zea mays (maize) assessed as root dry weight assessed per 10 plants at 400 ug/L measured 5 days post compound treatment (Rvb = 42.8 +/- 0.7 mg)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1112486	Inhibition of ALS in ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish)	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1080554	Increase in root diameter in Zea mays (maize) seedlings at 100 to 800 ug/L	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080552	Effect on root surface area in Zea mays (maize) seedlings at 100 to 800 ug/L	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1112485	Resistance index, ratio of I50 for ALS Ala122Tyr mutant in ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant to I50 for ALS-herbicide-susceptible Raphanus raphanistrum (wild radish)	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1082408	Reduction in sinapic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 3 to 10 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080555	Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 400 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1112487	Inhibition of ALS Ala122Tyr mutant in ALS-herbicide-resistant Raphanus raphanistrum WARR30 (wild radish) expressing ALS Ala122Tyr mutant	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1082389	Induction of PAL activity in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1082417	Induction of p-coumaric acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1112489	Herbicidal activity against two to three leaf stage ALS-herbicide-susceptible Raphanus raphanistrum WARR7 (wild radish) assessed as reduction in dry weight of above-ground biomass measured 3 weeks after compound treatment	2012	Pest management science, Aug, Volume: 68, Issue:8	A novel amino acid substitution Ala-122-Tyr in ALS confers high-level and broad resistance across ALS-inhibiting herbicides.
AID1082419	Growth inhibition in Pisum sativum (pea) at 69 uM added to nutrient medium measured 22 to 23 days post onset of compound treatment	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1082415	Induction of ferulic acid accumulation in Pisum sativum (pea) leaves at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080553	Effect on root volume in Zea mays (maize) seedlings at 100 to 800 ug/L	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080556	Phytotoxicity in Zea mays assessed (maize) as total root length measured per plant at 800 ug/L measured 5 days post compound treatment (Rvb = 12.32 +/- 1.46 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1082406	Induction of caffeic acid accumulation in Pisum sativum (pea) roots at 69 uM added to nutrient medium measured 5 to 15 days post onset of compound treatment by HPLC method	2011	Journal of agricultural and food chemistry, Sep-28, Volume: 59, Issue:18	Role of exogenously supplied ferulic and p-coumaric acids in mimicking the mode of action of acetolactate synthase inhibiting herbicides.
AID1080548	Reduction of root hair growth in Zea mays (maize) seedlings at 400 ug/L measured 48 hr post dose by microscopy	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
AID1080561	Phytotoxicity in Zea mays (maize) assessed as shoot height at 400 ug/L measured 5 days post compound treatment (Rvb = 6.89 +/- 0.30 cm)	2009	Journal of agricultural and food chemistry, Feb-25, Volume: 57, Issue:4	Enantioselectivity in the phytotoxicity of herbicide imazethapyr.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	3 (2.73)	18.2507
2000's	33 (30.00)	29.6817
2010's	53 (48.18)	24.3611
2020's	21 (19.09)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	112 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.06	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2	1	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
carbamates [no description available]	2.02	1	amino-acid anion
glycine [no description available]	2.78	3	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.41	1	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	3.63	9	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.03	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
putrescine [no description available]	2.06	1	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.44	2	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
atrazine [no description available]	7.05	1	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.9	2	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
dicamba Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.	7.41	1	dichlorobenzene; methoxybenzoic acid	agrochemical; environmental contaminant; herbicide; synthetic auxin; xenobiotic
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.01	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
uridine [no description available]	2.11	1	uridines	drug metabolite; fundamental metabolite; human metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.02	1	kanamycins	bacterial metabolite
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	2.01	1	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2	1	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.13	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
monomethylarsonic acid monomethylarsonic acid: structure given in first source	2.02	1	arsonic acids; one-carbon compound; organoarsonic acid
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.	2.31	1	isoxazoles; 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.	2.03	1	dichlorobenzene; phenylureas	agrochemical; environmental contaminant; herbicide; xenobiotic
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.05	1	dialdehyde	biomarker
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	1	diamino-1,3,5-triazine; methylthio-1,3,5-triazine	environmental contaminant; herbicide
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	7.13	1	copper group element atom; elemental silver	Escherichia coli metabolite
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.	2.72	3	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.04	1	cadmium molecular entity; zinc 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.	2.06	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	2.02	1	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
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.	2.72	3	titanium oxides	food colouring
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.47	2
metribuzin metribuzin : A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, tert-butyl group at position 6 and a methylsulfanyl group at position 3.	2.5	2	1,2,4-triazines; cyclic ketone; organic sulfide	agrochemical; environmental contaminant; herbicide; xenobiotic
dichlorfop-methyl dichlorfop-methyl: structure; herbicide for control of wild oat & foxtails in cereal crops. diclofop-methyl : A racemate composed of equimolar amounts of (R)- and (S)-diclofop-methyl. A proherbicide for diclofop, it is used for the control of wild oats and annual weeds in wheat, barley, rye and broad-leaved crops.. methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate : A methyl ester resulting from the formal condensation of the carboxylic acid group of 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid with methanol.	2.02	1	aromatic ether; dichlorobenzene; diether; methyl ester
chlorsulfuron chlorsulfuron: RN given refers to parent cpd; structure given in first source. chlorsulfuron : An N-sulfonylurea that is N-carbamoyl-2-chlorobenzenesulfonamide in which one of the hydrogens attached to the non-sulfonylated nitrogen has been replaced by a 4-methoxy-6-methyl-1,3,5-triazin-2-yl group. A herbicide used for the control of broadleaf weeds in wheat, barley and oats.	8.28	6	methoxy-1,3,5-triazine; monochlorobenzenes; N-sulfonylurea	agrochemical; EC 2.2.1.6 (acetolactate synthase) inhibitor; herbicide
haloxyfop haloxyfop: RN given refers to parent cpd. haloxyfop : A racemate comprising equimolar amounts of haloxyfop-P (the more active, R enantiomer) and (S)-haloxyfop (the less active enantiomer). A post-emergence herbicide used to control annual and perennial grass weeds. Commercial use of the racemate was phased out in favour of the most active enantiomer, used as the proherbicide esters haloxyfop-P-methyl and haloxyfop-P-etotyl.. 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid : A monocarboxylic acid that is 2-phenoxypropanoic acid in which the hydrogen at the para position of the phenyl ring has been replaced by a [3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy group.	2.02	1	aromatic ether; monocarboxylic acid; organochlorine compound; organofluorine compound; pyridines
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.	2.02	1	aromatic ether; carboxylic ester; organofluorine compound; pyridines
metsulfuron methyl metsulfuron methyl : A N-sulfonylurea in which the sulfonyl group is attached to a 2-(methoxycarbonyl)phenyl group while a (4-methoxy-6-methyl-1,3,5-triazin-2-yl group replaces one of the amino hydrogens of the remaining urea group.	3.29	5	1,3,5-triazines; benzoate ester; N-sulfonylurea	environmental contaminant; herbicide; xenobiotic
quizalofop-ethyl quizalofop-ethyl: RN given refers to parent cpd. quizalofop-ethyl : A racemate coprising equimolar amounts of quizalofop-P-ethyl and its enantiomer, (S)-quizalofop-ethyl. A proherbicide for quizalofop.. ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate : An ethyl ester resulting from the formal condensation of the carboxy group of 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid with ethanol.	2.13	1	aromatic ether; ethyl ester; organochlorine compound; quinoxaline derivative
imazapyr, (+-)-isomer imazapyr: RN given refers to parent cpd without isomeric designation. imazapyr : A racemate comprising equimolar amounts of (R)- and (S)-imazapyr. An inhibitor of acetohydroxyacid synthase, it is used (generally as the isopropylamine salt, known as imazapyr-isopropylammonium) as a herbicide, particularly for the control of perennial grasses, broad-leaved weeds, woody plants, brambles, etc., on non-crop land. It is not approved for use within the European Union.. 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid : A pyridinemonocarboxylic acid that is nicotinic acid which is substituted at position 2 by a 4,5-dihydro-imidazol-2-yl group, which in turn is substituted at positions 4, 4, and 5 by isopropyl, ethyl, and oxo groups, respectively.	3.73	10	imidazolines; imidazolone; pyridinemonocarboxylic acid; pyridines
imazaquin imazaquin: RN given refer to parent cpd. imazaquin : A racemate comprising equimolar amounts of (R)- and (S)-imazaquin. It is a pre- and post-emergence herbicide used for the control of grasses and broad-leaved weeds.. 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid : A quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2.	3.62	9	imidazolone; monocarboxylic acid; quinolinemonocarboxylic acid
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.	7.31	1	isoxazolidinone; monochlorobenzenes	agrochemical; carotenoid biosynthesis inhibitor; environmental contaminant; herbicide; xenobiotic
chlorimuron ethyl chlorimuron ethyl: structure in first source. chlorimuron-ethyl : An ethyl ester resulting from the formal condensation of the carboxy group of chlorimuron with ethanol. A proherbicide for chloimuron, it is used as herbicide for the control of broad-leaved weeds in peanuts, soya beans, and other crops.	2.47	2	aromatic ether; ethyl ester; N-sulfonylurea; organochlorine pesticide; pyrimidines; sulfamoylbenzoate	agrochemical; EC 2.2.1.6 (acetolactate synthase) inhibitor; proherbicide
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.	2.31	1	carbamate ester; oxazolidinone	metabolite
raptors imazamox: an experimental imidazolinone herbicide; structure in first source. 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid : A pyridinemonocarboxylic acid that is nicotinic acid which is substituted substituted at position 5 by a methoxymethyl group and at position 2 by a 4,5-dihydro-1H-imidazol-2-yl group, that in turn is substituted by isopropyl, methyl, and oxo groups at positions 4, 4, and 5, respectively.. imazamox : A racemate composed of equimolar amounts of (S)- and (R)-imazamox. An inhibitor of acetohydroxyacid synthase, it is used (particularly as the corresponding ammonium salt, known as imazamox-ammonium) as a herbicide for the control of grass, broad-leaf weeds, and pond weed.	3.08	4	ether; imidazolines; imidazolone; pyridinemonocarboxylic acid
n-(2,6-difluorophenyl)-5-methyl(1,2,4)-triazol(1,5-a)pyrimidine-2-sulfonamide [no description available]	2.07	1	sulfonamide
ac 263,222 imazapic: imidazolinone herbicide. imazapic : A racemate comprising equimolar amounts of (R)- and (S)-imazapic. It is a selective imidazolinone herbicide for pre- and post-emergent control of some annual and perennial grasses and broadleaf weeds. It kills plants by inhibiting the activity of the enzyme acetohydroxy acid synthase (AHAS).. 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid : A pyridinemonocarboxylic acid that is 5-methylpyridine-3-carboxylic acid which is substituted at position 2 by a 4,5-dihydro-imidazol-2-yl group, which in turn is substituted at positions 4, 4, and 5 by isopropyl, methyl, and oxo groups, respectively.	3.22	5	imidazolines; imidazolone; methylpyridines; pyridinemonocarboxylic acid
s 53482 flumioxazin : A benzoxazine that is N-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one which is substituted at position 6 by a 1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl group and at position 7 by a fluorine. A protoporphyrinogen oxidase inhibitor, it is used for the control of weeds in soya, peanuts, and a variety of vegetable and fruit crops.	2.76	2	benzoxazine; dicarboximide; organofluorine compound; terminal acetylenic compound	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide; teratogenic agent
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	7.03	1	oxygen hydride; oxygen radical; reactive oxygen species
propisochlor [no description available]	2.03	1
mesotrione mesotrione: brandname is after the Callistemon (MYRTACEAE) plant it was found in; structure in first source. mesotrione : An aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group.	2.15	1	aromatic ketone; beta-triketone; C-nitro compound; sulfone	carotenoid biosynthesis inhibitor; EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor; environmental contaminant; herbicide; xenobiotic
bispyribac bispyribac: acute human self-poisoning with bispyribac-containing herbicide Nominee has been reported; structure in first source. bispyribac : A member of the class of benzoic acids that is benzoic acid substituted by (4,6-dimethoxypyrimidin-2-yl)oxy groups at positions 2 and 6. Its sodium salt is used as a broad spectrum post emergent herbicide for the control of grasses, sedges and broadleaf weeds in rice crops.	7.8	3	aromatic ether; benzoic acids; monocarboxylic acid; pyrimidines	herbicide
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.66	2	cyclodextrin
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.06	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.06	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.02	1	metalloid atom; pnictogen	micronutrient
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	7.6	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
ferrihydrite ferric oxyhydroxide: an antiferromagnetic material; constitutes the core of natural ferritin; mol form 5Fe2O3.9H2O	2.7	3
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.05	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
mesosulfuron-methyl mesosulfuron-methyl: an herbicide	2.21	1
florasulam florasulam: structure in first source	2.86	3	sulfonamide
granite granite: crystalline rock of quartz, orthoclase, muscovite & biotite	2.11	1	triazolopyrimidines
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.13	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
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.	2.08	1	chlorophyll; methyl ester	cofactor
chitosan [no description available]	2.66	2
pyrithiobac sodium [no description available]	2.55	2	organic molecular entity
mannans [no description available]	2.15	1
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	2.02	1
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	2.74	3
volunteers clethodim: structure in first source. 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.	2.02	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.07	1

Condition	Relationship Strength	Studies
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)	2.45	2
Abnormalities, Autosome [description not available]	2.52	2
Chromosome-Defective Micronuclei [description not available]	2.11	1
Bladder Cancer [description not available]	2.05	1
Cancer of Colon [description not available]	2.05	1
Agricultural Worker Disease [description not available]	2.05	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.05	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.05	1

imazethapyr

Description

Cross-References

Synonyms (64)

Research Excerpts

Overview

Toxicity

Bioavailability

Dosage Studied

Drug Classes (2)

Protein Targets (7)

Potency Measurements

Inhibition Measurements

Biological Processes (50)

Molecular Functions (23)

Ceullar Components (3)

Bioassays (47)

Research

Studies (110)

Market Indicators

Research Demand Index: 40.69

Study Types

imazethapyr

Description

Cross-References

Synonyms (64)

Research Excerpts

Overview

Toxicity

Bioavailability

Dosage Studied

Drug Classes (2)

Protein Targets (7)

Potency Measurements

Inhibition Measurements

Biological Processes (50)

Molecular Functions (23)

Ceullar Components (3)

Bioassays (47)

Research

Studies (110)

Market Indicators

Research Demand Index: 40.69

Study Types

Related Drugs (69)

Related Conditions (8)