Compounds > oxathiapiprolin
Page last updated: 2024-11-13

oxathiapiprolin

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Description

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

1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone : An N-acylpiperidine that is N-acetyl 4-(1,3-thiazol-2-yl)piperidine in which the thiazole ring is substituted at position 4 by a 5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl group and in which one of the hydrogens of the acetyl group is replaced by a 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl 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]

oxathiapiprolin : A racemate comprising equimolar amounts of (R)- and (S)-oxathiapiprolin. [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 CID56945145
CHEBI ID83271
SCHEMBL ID120216
MeSH IDM000599041

Synonyms (20)

Synonym
SCHEMBL120216
1-(4-(4-((5rs)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl)-1-piperidyl)-2-(5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl)ethanone
1003318-67-9
1-(4-(4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)-1-piperidinyl)-2-(5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl)ethanone
unii-56498aiv8r
dpx-qgu42
ethanone, 1-(4-(4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl)-1-piperidinyl)-2-(5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl)-
oxathiapiprolin [iso]
oxathiapiprolin
56498aiv8r ,
1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl]ethanone
CHEBI:83271
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl]ethanone; 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(tr
DTXSID30893604
Q27156718
IAQLCKZJGNTRDO-UHFFFAOYSA-N ,
1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone
oxathiapiprolin 100 ?g/ml in acetonitrile
zorvec
ethanone, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1h-pyrazol-1-yl]-

Research Excerpts

Overview

Oxathiapiprolin is a piperidinyl thiazole isoxazoline fungicide discovered by DuPont and commercialized by Corteva Agriscience. It can affect the metabolism of the cholesterol compounds by inhibiting oxysterol binding protein (OSBP) to exert its fungicidal effect.

ExcerptReferenceRelevance
"Oxathiapiprolin is a piperidinyl thiazole isoxazoline fungicide discovered by DuPont and commercialized by Corteva Agriscience. "( Genetic mechanism, baseline sensitivity and risk of resistance to oxathiapiprolin in oomycetes.
Carroll, A; Genet, JL; Jaworska, G; Mboup, MK; Sweigard, JW, 2022)		2.4
"Oxathiapiprolin is an efficient and chiral fungicide for peronosporomycetes. "( Enantioselective aquatic toxicity and degradation in soil of the chiral fungicide oxathiapiprolin.
Gao, Y; Shi, H; Wang, M; Wu, Q; Zhou, L, 2022)		2.39
"Oxathiapiprolin is a chiral fungicide, and it can affect the metabolism of the cholesterol compounds by inhibiting oxysterol binding protein (OSBP) to exert its fungicidal effect. "( Toxicokinetics of Two Oxathiapiprolin Enantiomers in Rats and Their Stereoselective Interaction with Oxysterol Binding Protein.
Ai, J; Chang, AK; Fu, H; Li, H; Li, J; Liang, X; Liu, K; Liu, W; Liu, Y; Pei, Y; Su, W; Zhang, X; Zhuang, C, 2022)		2.48
"Oxathiapiprolin is a novel fungicide and the first of the piperidinyl-thiazole-isoxazoline class to be discovered. "( Characterization of Italian Plasmopara viticola populations for resistance to oxathiapiprolin.
Bianco, PA; Borghi, L; Borsa, P; Coatti, M; Massi, F; Toffolatti, SL; Torriani, SF; Waldner-Zulauf, M, 2023)		2.58
"Oxathiapiprolin is a fungicide effective against downy mildews of cucumber (Pseudoperonospora cubensis) and basil (Peronospora belbahrii) and late blight of tomato (Phytophthora infestans). "( Root treatment with oxathiapiprolin, benthiavalicarb or their mixture provides prolonged systemic protection against oomycete foliar pathogens.
Cohen, Y, 2020)		2.32
"Oxathiapiprolin is a chiral fungicide used in China for the prevention and treatment of grape downy mildew, but its potential risk could be inaccurately assessed without distinguishing its enantiomers. "( Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry.
Dong, F; Jiang, D; Li, R; Liu, Q; Liu, X; Liu, Y; Wu, X; Xu, J; Zheng, Y, 2020)		2.26
"Oxathiapiprolin is a novel fungicide that was recently registered in a number of countries to control plant-pathogenic oomycetes such as Phytophthora capsici. "( Mutations in ORP1 Conferring Oxathiapiprolin Resistance Confirmed by Genome Editing using CRISPR/Cas9 in Phytophthora capsici and P. sojae.
Chi, Y; Lin, D; Liu, X; Miao, J; Tyler, BM, 2018)		2.21
"Oxathiapiprolin is a new fungicide with extremely high efficacy against oomycete plant pathogens. "( Oxathiapiprolin-based fungicides provide enhanced control of tomato late blight induced by mefenoxam-insensitive Phytophthora infestans.
Cohen, Y; Galperin, M; Rubin, AE, 2018)		3.37
"Oxathiapiprolin is a new oomycide (piperidinyl thiazole isoxazoline class) discovered by DuPont which controls diseases caused by oomycete plant pathogens. "( The Novel Oomycide Oxathiapiprolin Inhibits All Stages in the Asexual Life Cycle of Pseudoperonospora cubensis - Causal Agent of Cucurbit Downy Mildew.
Cohen, Y, 2015)		2.19

Treatment

ExcerptReferenceRelevance
"Root treatment with oxathiapiprolin, benthiavalicarb or their mixture Zorvec-Endavia [ZE (3+7, w/w)] was shown to provide prolonged systemic protection against foliar oomycete pathogens attacking cucumber, tomato and basil. "( A new strategy for durable control of late blight in potato by a single soil application of an oxathiapiprolin mixture in early season.
Cohen, Y; Rubin, AE, 2020)		1.1

Toxicity

ExcerptReferenceRelevance
"An effective and rapid analytical method for the simultaneous determination of a new fungicide oxathiapiprolin and its metabolites (IN-E8S72 and IN-WR791) residues in fruits (grape, watermelon, watermelon peel), vegetables (cucumber, tomato, potato) and cereal (wheat) was developed by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) using the modified quick, easy, cheap, effective, rugged, and safe (QuEChERS) extraction concept."( Simultaneous determination of oxathiapiprolin and two metabolites in fruits, vegetables and cereal using a modified quick, easy, cheap, effective, rugged, and safe method and liquid chromatography coupled to tandem mass spectrometry.
Dong, F; Li, Y; Liu, X; Wu, X; Xu, J; Zheng, Y, 2014)		0.91
" In this study, we evaluated the toxic effects of Otp in the Chlorella vulgaris (C."( Toxicity of the novel fungicide oxathiapiprolin to Chlorella vulgaris: Assessments at different levels of biological organization.
Ding, Z; Huang, C; Jia, H; Lv, X; Wang, F; Wang, J; Wei, J; Zhang, F, 2022)		1

Bioavailability

ExcerptReferenceRelevance
" The two oxathiapiprolin enantiomers were found to have approximately the same absorption rate and bioavailability, and both were excreted mainly in the feces."( Toxicokinetics of Two Oxathiapiprolin Enantiomers in Rats and Their Stereoselective Interaction with Oxysterol Binding Protein.
Ai, J; Chang, AK; Fu, H; Li, H; Li, J; Liang, X; Liu, K; Liu, W; Liu, Y; Pei, Y; Su, W; Zhang, X; Zhuang, C, 2022)		1.45
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (6)

ClassDescription
N-acylpiperidine
1,3-thiazoles
pyrazoles
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
isoxazolineAn organic heteromonocyclic compound that is a dihydro derivative of any isoxazole.
tertiary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a secondary amine; formula RC(=O)NHR(1)R(2).
[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]

Research

Studies (41)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's17 (41.46)24.3611
2020's24 (58.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.83

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.83 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index4.69 (4.65)
Search Engine Demand Index68.41 (26.88)
Search Engine Supply Index3.01 (0.95)

This Compound (34.83)

All Compounds (24.57)

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%
Other41 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.2510amino-acid anion
salicylic acid
Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).		2.2510monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite
ether
Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.		2.610ether;
volatile organic compound		inhalation anaesthetic;
non-polar solvent;
refrigerant
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		3.4860alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.2510cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
thiazoles
[no description available]		2.6101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
tetrachloroisophthalonitrile
tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.		2.1710aromatic fungicide;
dinitrile;
tetrachlorobenzene		antifungal agrochemical
metalaxyl
metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.		7.4110alanine derivative;
aromatic amide;
carboxamide;
ether;
methyl ester
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.2510D-glucopyranoseepitope;
mouse metabolite
s-methyl benzo(1,2,3)thiadiazole-7-carbothioate
S-methyl benzo(1,2,3)thiadiazole-7-carbothioate: induces system acquired resistance in wheat; structure in first source. acibenzolar-S-methyl : A benzothiadiazole that is the S-methyl thioester derivative of acibenzolar. A profungicide (by hydrolysis of the thioester group to give the corresponding carboxylic acid), it is used as a fungicide and plant activator on a variety of crops, including cotton, chili peppers, lettuce, onions, spinach, tobacco, and tomatoes.		2.2110benzothiadiazole;
thioester		antifungal agrochemical;
plant activator;
profungicide
famoxadone
famoxadone: strobilurin analogue; structure in first source. famoxadone : A racemate composed of equimolar amounts of (R)- and (S)-famoxadone. It prevents spore germination and mycelial growth of sensitive fungi, and is used in agriculture for the control of various fungal diseases. Only the (S)- enantiomer is active.. 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione : A member of the class of oxazolidinones that is 1,3-oxazolidine-2,4-dione in which the hydrogen attached to the nitrogen is substituted by a phenylamino group and the hydrogens at position 5 are substituted by methyl and 4-phenoxyphenyl groups.		2.9330aromatic ether;
carbohydrazide;
oxazolidinone
azoxystrobin
azoxystrobin: a methoxyacrylate analog; a strobilurin fungicide; structure given in first source. azoxystrobin : An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture.		2.1710aryloxypyrimidine;
enoate ester;
enol ether;
methoxyacrylate strobilurin antifungal agent;
methyl ester;
nitrile		antifungal agrochemical;
environmental contaminant;
mitochondrial cytochrome-bc1 complex inhibitor;
quinone outside inhibitor;
xenobiotic
jasmonic acid
jasmonic acid: a derivative of alpha-linolenic acid that has a role in plant response to herbivory analogous to the role of prostanoids in inflammation in mammals;. jasmonic acid : An oxo monocarboxylic acid that is (3-oxocyclopentyl)acetic acid substituted by a (2Z)-pent-2-en-1-yl group at position 2 of the cyclopentane ring.		2.2510oxo monocarboxylic acidjasmonates;
plant metabolite
dimethomorph
dimethomorph: structure given in first source; RN given refers to cpd without isomeric designation. (Z)-dimethomorph : An enamide resulting from the formal condensation of (2Z)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylic acid with the amino group of morpholine. The agricultural fungicide dimethomorph is a mixture of (E)- and (Z)-dimethomorph; only the Z isomer has fungicidal activity.. dimethomorph : A mixture of (E)- and (Z)-dimethomorph in an unspecified ratio. It is used as a systemic fungicide used on vines, potatoes, and greenhouse crops; only the Z isomer has fungicidal activity.		2.3110aromatic ether;
enamide;
monochlorobenzenes;
morpholine fungicide;
tertiary carboxamide
cyazofamid
cyazofamid: a fungicide; structure in first source. cyazofamid : A member of the class of imidazoles carrying dimethylsulfamyl, cyano, chloro and 4-tolyl substituents at positions 1, 2, 4 and 5 respectively. A fungicide used mainly for controlling Oomycete and Plasmodiophora diseases on potatoes and tomatoes. It is a skin and eye irritant and is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.		2.3110imidazole fungicide;
imidazoles;
nitrile;
organochlorine compound;
sulfamides;
sulfonamide fungicide		antifungal agrochemical;
mitochondrial cytochrome-bc1 complex inhibitor
mefenoxam
metalaxyl-M : A methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate that is the more active R-enantiomer of metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.		3.4960acylamino acid fungicide;
anilide fungicide;
D-alanine derivative;
methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate		agrochemical
fluopicolide
fluopicolide: structure in first source. fluopicolide : A member of the class of benzamides obtained by formal condensation of the carboxy group of 2,6-dichlorobenzoic acid with the amino group of [3-chloro-5-(trifluoromethyl)pyridin-2-yl]methylamine. A fungicide used for the control of a range of diseases including downy mildew and blight.		2.3110benzamide fungicide;
benzamides;
dichlorobenzene;
monochloropyridine;
organofluorine compound		antifungal agrochemical
mandipropamid
mandipropamid: effective against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew). mandipropamid : A racemate comprising equimolar amounts of (R)- and (S)-mandipropamid. An agricultural fungicide, it is used to control late blight and downy mildew in many salad, vegetable and fruit crops.. 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide : A monocarboxylic acid amide resulting from the condensation of the carboxy group of p-chloromandelic acid propargyl ether with the amino group of 2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethylamine.		8.2540aromatic ether;
monocarboxylic acid amide;
monochlorobenzenes;
terminal acetylenic compound
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.		2.4110chlorophyll;
methyl ester		cofactor
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Resistance
The capacity of an organism to defend itself against pathological processes or the agents of those processes. This most often involves innate immunity whereby the organism responds to pathogens in a generic way. The term disease resistance is used most frequently when referring to plants.		09.42130
Lipid Metabolism Disorders
Pathological conditions resulting from abnormal anabolism or catabolism of lipids in the body.		07.610