Page last updated: 2024-10-14

mandipropamid

Description

mandipropamid: effective against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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-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. [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 CID11292824
CHEMBL ID271907
CHEBI ID83617
SCHEMBL ID22338
MeSH IDM0548450

Synonyms (36)

Synonym
mandipropamid
CHEMBL271907
chebi:83617 ,
374726-62-2
unii-11gp4elk0u
11gp4elk0u ,
2-(4-chlorophenyl)-n-(2-(3-methoxy-4-(2-propyn-1-yloxy)phenyl)ethyl)-2-(2-propyn-1-yloxy)acetamide
hsdb 7878
revus
mpd fungicide
mandipropamid [iso]
C18522
2-(4-chlorophenyl)-n-[3-methoxy-4-(2-propynyloxy)phenethyl]-2-(2-propynyloxy)acetamide
AKOS025295244
SCHEMBL22338
pergado
2-(4-chlorophenyl)-n-(2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl)-2-(prop-2-ynyloxy)acetamide
benzeneacetamide, 4-chloro-n-(2-(3-methoxy-4-(2-propynyloxy)phenyl)ethyl)-.alpha.-(2-propynyloxy)-
(+/-)-chlorophenyl)-n-(2-(3-methoxy-4-(prop-2-ynyloxy)phenyl)ethyl)-2-(prop-2-ynyloxy)acetamide
benzeneacetamide, 4-chloro-n-(2-(3-methoxy-4-(2-propyn-1-yloxy)phenyl)ethyl)-.alpha.-(2-propyn-1-yloxy)-
mandipropamid [mi]
mandipropamid [hsdb]
2-(4-chlorophenyl)-n-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide
KWLVWJPJKJMCSH-UHFFFAOYSA-N
2-(4-chloro-phenyl)-n-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-(prop-2-ynyloxy)-acetamide
2-(4-chloro-phenyl)-n-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide
2-(4-chloro-phenyl)-n-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide
DTXSID4058075
mandipropamid 10 microg/ml in cyclohexane
mandipropamid 100 microg/ml in acetonitrile
BCP25579
2-(4-chlorophenyl)-n-[2-(3-methoxy-4-prop-2-ynoxyphenyl)ethyl]-2-prop-2-ynoxyacetamide
Q2057167
benzeneacetamide, 4-chloro-n-[2-[3-methoxy-4-(2-propyn-1-yloxy)phenyl]ethyl]-.alpha.-(2-propyn-1-yloxy)-
2-(4-chlorophenyl)-n-(3-methoxy-4-(prop-2-ynyloxy)phenethyl)-2-(prop-2-ynyloxy)acetamide
AT33985

Research Excerpts

Overview

Mandipropamid (MDP) is a widely used chiral fungicide to control oomycete pathogens with two enantiomers. It is currently registered as a soil treatment for citrus nursery container plants to manage Phytophthora root rot.

ExcerptReference
"Mandipropamid (MDP) is a widely used chiral fungicide to control oomycete pathogens with two enantiomers. "( Enantioselective Bioactivity, Toxicity, and Degradation in Vegetables and Soil of Chiral Fungicide Mandipropamid.
He, Z; Wang, M; Wang, Z; Wu, Q; Zhang, J; Zhang, Y; Zhong, Y, 2021
)
"Mandipropamid is an Oomycota fungicide that is currently registered as a soil treatment for citrus nursery container plants to manage Phytophthora root rot."( Root Absorption and Limited Mobility of Mandipropamid as Compared to Oxathiapiprolin and Mefenoxam After Soil Treatment of Citrus Plants for Managing Phytophthora Root Rot.
Adaskaveg, JE; Belisle, RJ; Förster, H; Hao, W; Riley, N, 2023
)
"Mandipropamid (MDP) is a chiral fungicide that has been widely used to control oomycete pathogens. "( The enantioselective environmental fate of mandipropamid in water-sediment microcosms: Distribution, degradation, degradation pathways and toxicity assessment.
Li, R; Li, Y; Tan, Y; Wang, M; Zhang, J; Zhang, Y; Zhou, L, 2023
)
"Mandipropamid (MPD) is a carboxylic acid amide (CAA) effective against downy mildews, such as Plasmopara viticola on grapes and potato late blight caused by Phytophthora infestans."( Mandipropamid targets the cellulose synthase-like PiCesA3 to inhibit cell wall biosynthesis in the oomycete plant pathogen, Phytophthora infestans.
Avrova, AO; Blum, M; Boehler, M; Csukai, M; Fonne-Pfister, R; Kraus, S; Moulin, F; Randall, E; Scalliet, G; Whisson, SC; Young, V, 2010
)

Dosage Studied

ExcerptReference
" This study not only provides a reasonable spray dosage of mandipropamid to ginseng but also offers a reference for the establishment of MRLs in China."( Degradation and residues of mandipropamid in soil and ginseng and dietary risk assessment in Chinese culture.
Cao, Z; Hou, X; Hou, Z; Liu, H; Lu, Z; Wei, L, 2023
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
terminal acetylenic compoundAn acetylenic compound which a carbon of the C#C moiety is attached to a hydrogen atom.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
[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 (9)

Assay IDTitleYearJournalArticle
AID420438Antioomycetic activity against Phytophthora infestans2009Bioorganic & medicinal chemistry, Jun-15, Volume: 17, Issue:12
Alkyne chemistry in crop protection.
AID1112515Antifungal activity against Pythium aphanidermatum assessed as inhibition of mycelial growth at 100 uM after 3 days2012Pest management science, Aug, Volume: 68, Issue:8
Insights into the molecular mechanism of tolerance to carboxylic acid amide (CAA) fungicides in Pythium aphanidermatum.
AID320443Antifungal activity against Phytophthora infestans in tomato late blight after 4 days2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Multicomponent reactions in fungicide research: the discovery of mandipropamid.
AID420439Antioomycetic activity against Plasmopara viticola2009Bioorganic & medicinal chemistry, Jun-15, Volume: 17, Issue:12
Alkyne chemistry in crop protection.
AID1112516Antifungal activity against Pythium aphanidermatum assessed as inhibition of mycelial growth at 10 uM after 3 days2012Pest management science, Aug, Volume: 68, Issue:8
Insights into the molecular mechanism of tolerance to carboxylic acid amide (CAA) fungicides in Pythium aphanidermatum.
AID1112503Up-regulation of CesA2 gene expression in Pythium aphanidermatum at 100 uM after 8 hr by qRT-PCR method relative to untreated control2012Pest management science, Aug, Volume: 68, Issue:8
Insights into the molecular mechanism of tolerance to carboxylic acid amide (CAA) fungicides in Pythium aphanidermatum.
AID1112504Up-regulation of CesA1 gene expression in Pythium aphanidermatum at 100 uM after 8 hr by qRT-PCR method relative to untreated control2012Pest management science, Aug, Volume: 68, Issue:8
Insights into the molecular mechanism of tolerance to carboxylic acid amide (CAA) fungicides in Pythium aphanidermatum.
AID320444Antifungal activity against Plasmopara viticola in grape downy mildew after 6 days2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Multicomponent reactions in fungicide research: the discovery of mandipropamid.
AID1112512Inhibition of germ tube elongation of Pythium aphanidermatum synchronised cytospores at 0.5 to 121 uM after 4 hr2012Pest management science, Aug, Volume: 68, Issue:8
Insights into the molecular mechanism of tolerance to carboxylic acid amide (CAA) fungicides in Pythium aphanidermatum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (6.90)29.6817
2010's12 (41.38)24.3611
2020's15 (51.72)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%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other28 (96.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]