Page last updated: 2024-09-26

quizalofop

Description

quizalofop : A racemate comprising equimolar amounts of quizalofop-P of and (S)-quizalofop. Quizalofop is used (commonly as the corresponding ethyl ester, known as quizalofop-ethyl) as a selective post-emergence herbicide against annual and winter-hard grasses. The active isomer is the R enantiomer, which is known as quizalofop-P. [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]

2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid : A monocarboxylic acid that is 2-phenoxypropanoic acid in which the phenyl group is substituted at the para position by a (6-chloroquinoxalin-2-yl)oxy group. [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 CID178795
CHEMBL ID51789
CHEBI ID137509
CHEBI ID81943
SCHEMBL ID111413
MeSH IDM0453684

Synonyms (36)

Synonym
quizalofop
2-[4-(6-chloroquinoxalin-2-yl)oxyphenoxy]propanoic acid
76578-12-6
CHEBI:137509
2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propionic acid
2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid
CHEMBL51789
chebi:81943
C18763
AKOS015960672
(rs)-2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propionic acid
ccris 9407
xylafop
propanoic acid, 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-
137f325077 ,
quizalofop [bsi:iso]
(+-)-2-(4-(6-chloro-2-quinoxalinyloxy)phenoxy)propanoic acid
unii-137f325077
FT-0630846
quizalofop [iso]
SCHEMBL111413
ABOOPXYCKNFDNJ-UHFFFAOYSA-N
2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionic acid
2-[4-(6-chloro-2-quinoxalyloxy)phenoxy]propionic acid
DTXSID60273935
propanoic acid, 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-
quizalofop (free acid) 10 microg/ml in acetonitrile
quizalofop (free acid)
as sur-
2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propanoic acid
propaquizafop acid (cga 287422)
BCP07599
FT-0772688
Q2123552
n-acetyl-l-cysteine;acetylcysteine
D85430

Research Excerpts

Overview

ExcerptReference
"Quizalofop-p-ethyl (QPE) is a post-emergence herbicide that effectively controls grass weeds and is often detected in the environment. "( Li, J; Li, M; Liu, Y; Wang, G; Zhang, H, 2017)

Drug Classes (4)

ClassDescription
quinoxaline derivativeAny naphthyridine derivative that is a derivative of quinoxaline (1,4-naphthyridine).
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
monocarboxylic acidAn oxoacid containing a single carboxy group.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
[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]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID278576Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after 48 hrs2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Inhibitors of nonhousekeeping functions of the apicoplast defy delayed death in Plasmodium falciparum.
AID493460Inhibition of maize ACC2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Dimeric cyclohexane-1,3-dione oximes inhibit wheat acetyl-CoA carboxylase and show anti-malarial activity.
AID121317In vivo activity tested against C3H mice bearing colon adenocarcinoma -38(colon-38) tumor measured as % treated/control calculated at 1590 mg/kg (po)2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469).
AID278577Inhibition of Plasmodium falciparum FCK2 growth as [3H]hypoxanthine uptake after 96 hrs2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Inhibitors of nonhousekeeping functions of the apicoplast defy delayed death in Plasmodium falciparum.
AID1102195Increase of PHA synthase level in BC3 transgenic Nicotiana tabacum (tobacco) at 10 uM sprayed on five leaf stage plant once in a week measured after 2 weeks by immunoblot analysis2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102198Increase of poly-3-hydroxybutyrate production in BC3 transgenic Nicotiana tabacum (tobacco) at 2 to 50 uM sprayed on five-leaf stage plant once in a week measured after 2 weeks relative to control2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID493458Antimalarial activity against Plasmodium falciparum D102010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Dimeric cyclohexane-1,3-dione oximes inhibit wheat acetyl-CoA carboxylase and show anti-malarial activity.
AID1102191Increase of poly-3-hydroxybutyrate production in rCAB8 transgenic Nicotiana tabacum (tobacco) at 50 uM sprayed on five-leaf stage plant once in a week measured after 1 week relative to control2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102189Increase of poly-3-hydroxybutyrate production in BC3 transgenic Nicotiana tabacum (tobacco) plastids at 10 uM sprayed on five-leaf stage plant once in a week measured after 2 weeks relative to cytosol2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102194Increase of PHA synthase level in rCAB8 transgenic Nicotiana tabacum (tobacco) at 50 uM sprayed on five leaf stage plant once in a week measured after 2 weeks by immunoblot analysis2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID124039In vivo activity tested against C3H mice bearing colon adenocarcinoma -38(colon-38) tumor measured as body weight loss at 1590 mg/kg (po)2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469).
AID1102197Increase of leaf dry weight in rCAB8 transgenic Nicotiana tabacum (tobacco) at 10 to 250 uM sprayed on five leaf stage plant once in a week measured after 2 weeks2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102196Increase of poly-3-hydroxybutyrate production in rCAB8 transgenic Nicotiana tabacum (tobacco) at 50 uM sprayed on five-leaf stage plant once in a week measured after 2 weeks relative to control2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102188Increase of poly-3-hydroxybutyrate production in rCAB8 transgenic Nicotiana tabacum (tobacco) plastids at 50 uM sprayed on five-leaf stage plant once in a week measured after 2 weeks relative to cytosol2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID124269In vivo activity tested against C3H mice bearing colon adenocarcinoma -38(colon-38) tumor measured as log Kill value was based on tumors that grew at 1590 mg/kg (po); None2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469).
AID1102193Increase of leaf dry weight in BC3 transgenic Nicotiana tabacum (tobacco) at 10 uM sprayed on five leaf stage plant once in a week measured after 1 week2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102190Increase of poly-3-hydroxybutyrate production in BC3 transgenic Nicotiana tabacum (tobacco) at 10 uM sprayed on five leaf stage plant once in a week measured after 2 weeks relative to control2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID1102192Increase of poly-3-hydroxybutyrate production in BC3 transgenic Nicotiana tabacum (tobacco) at 10 uM sprayed on five-leaf stage plant once in a week measured after 1 week relative to control2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
AID123114In vivo activity tested against C3H mice bearing colon adenocarcinoma -38(colon-38) tumor measured as activity rating at 1590 mg/kg (po)2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469).
AID1102199Increase of leaf dry weight in BC3 transgenic Nicotiana tabacum (tobacco) sprayed on five-leaf stage plant once in a week measured after 2 weeks2002Bioscience, biotechnology, and biochemistry, Dec, Volume: 66, Issue:12
Enzyme inhibitors to increase poly-3-hydroxybutyrate production by transgenic tobacco.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (28.00)29.6817
2010's12 (48.00)24.3611
2020's6 (24.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (2)

ArticleYear
Safety profile evaluation of different herbicides used on peach rootstock seedlings.
Ying yong sheng tai xue bao = The journal of applied ecology, Volume: 34, Issue: 6
2023
Chiral quizalofop-ethyl and its metabolite quizalofop-acid in soils: Enantioselective degradation, enzymes interaction and toxicity to Eisenia foetida.
Chemosphere, Volume: 152
2016
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
Enantioselective metabolism of quizalofop-ethyl in rat.
PloS one, Volume: 9, Issue: 6
2014
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Quizalofop resistance in weedy rice (Oryza sativa L.) is mainly conferred by an Ile1781Leu mutation.
Plant science : an international journal of experimental plant biology, Volume: 336
2023
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]