Compounds > fenpiclonil
Page last updated: 2024-11-06

fenpiclonil

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

Description

Fenpiclonil is a broad-spectrum fungicide used to control a variety of diseases in a wide range of crops. It is a dicarboximide fungicide, meaning it inhibits the biosynthesis of certain key enzymes in fungi. Fenpiclonil's mechanism of action involves the inhibition of succinate dehydrogenase, an enzyme crucial for the fungal electron transport chain. This disruption leads to the disruption of energy production and eventually, fungal cell death. Fenpiclonil is applied to crops as a foliar spray or seed treatment, providing protection against fungal infections during various stages of plant growth. It is considered a systemic fungicide, meaning it is absorbed by the plant and translocated throughout the plant's tissues. Fenpiclonil's effectiveness against a broad spectrum of fungi makes it a valuable tool in managing fungal diseases. It is effective against fungal pathogens like Botrytis cinerea (gray mold), Venturia inaequalis (apple scab), and Monilinia spp. (brown rot). The development of resistance to fenpiclonil has been observed in some fungal pathogens. Research continues to investigate the efficacy and safety of fenpiclonil, including its potential environmental impact and the development of resistant strains of fungi. Ongoing research on fenpiclonil includes optimization of its application methods, development of alternative fungicides with similar efficacy, and the investigation of its potential impact on human health and the environment. It is typically used in combination with other fungicides to prevent the development of resistance.'

fenpiclonil : A member of the class of pyrroles carrying cyano and 2,3-dichlorophenyl substituents at positions 3 and 4 respectively. A fungicide used mainly to control seed-borne pathogens in cereal 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]

Cross-References

ID SourceID
PubMed CID91724
CHEMBL ID1770195
CHEBI ID34759
SCHEMBL ID22130
MeSH IDM0402225

Synonyms (29)

Synonym
beret
1h-pyrrole-3-carbonitrile, 4-(2,3-dichlorophenyl)-
4-cyano-3-(2,3-dichlorophenyl)pyrrole
fenpiclonil [iso]
cga 142705
brn 5433281
fenpiclonil
74738-17-3
3-(2,3-dichlorophenyl)-4-cyanopyrrole
4-(2,3-dichlorophenyl)-1h-pyrrole-3-carbonitrile
CHEMBL1770195
chebi:34759 ,
21ocb8kdq9 ,
unii-21ocb8kdq9
FT-0630838
AKOS015902859
cga-142705
galbas
gambit
fenpiclonil [mi]
SCHEMBL22130
3-cyano-4-(2,3-dichlorophenyl)pyrrole
4-(2,3-dichlorophenyl)-3-cyanopyrrole
4-(2,3-dichlorophenyl)pyrrole-3-carbonitrile
DTXSID0036633
fenpicionil
fenpiclonil, pestanal(r), analytical standard
Q3068402
ZCA73817

Research Excerpts

Overview

Fenpiclonil is an agricultural phenylpyrrole fungicide, which raise the concern about its ecotoxicological effects.

ExcerptReferenceRelevance
"Fenpiclonil is an agricultural phenylpyrrole fungicide, which raise the concern about its ecotoxicological effects. "( Mechanisms, kinetics and eco-toxicity assessment of singlet oxygen, sulfate and hydroxyl radicals-initiated degradation of fenpiclonil in aquatic environments.
Gao, J; Lv, G; Sun, X; Wang, Z; Yang, J, 2021)		2.27

Dosage Studied

ExcerptRelevanceReference
" Their fungicidal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed excellent fungicidal activities in vitro against Alternaria solani , Gibberella zeae , Physalospora piricola , Fusarium omysporum , and Cercospora arachidicola at the dosage of 50 microg mL(-1)."( Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
Feng, Q; Li, ZM; Wang, LZ; Wang, MZ; Wang, SH; Xu, H, 2009)		0.35
" Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL(-1)."( Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
Feng, Q; Li, ZM; Liu, TW; Wang, MZ; Wang, SH; Xu, H; Yu, SJ, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antifungal agrochemicalAny substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
pyrrolesAn azole that includes only one N atom and no other heteroatom as a part of the aromatic skeleton.
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
[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
AID594184Antimicrobial activity against Cercospora arachidicola at 50 ug/mL by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594188Antimicrobial activity against Alternaria solani by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594185Antimicrobial activity against Fusarium omysporum at 50 ug/mL by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594189Antimicrobial activity against Cercospora arachidicola by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594183Antimicrobial activity against Alternaria solani at 50 ug/mL by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594186Antimicrobial activity against Gibberella zeae at 50 ug/mL by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID1080778Fungicidal activity against Alternaria solani assessed as mycelium growth inhibition by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080774Fungicidal activity against Mycosphaerella arachidis assessed as mycelium growth inhibition by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID594249Antimicrobial activity against Gibberella zeae by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID1080793Fungicidal activity against Alternaria solani assessed as mycelium growth inhibition at 50 ug/mL by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080776Fungicidal activity against Botryosphaeria berengeriana assessed as mycelium growth inhibition by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080788Fungicidal activity against Botryosphaeria berengeriana assessed as mycelium growth inhibition at 50 ug/mL by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID594250Antimicrobial activity against Physalospora piricola by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID594187Antimicrobial activity against Physalospora piricola at 50 ug/mL by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID1080789Fungicidal activity against Fusarium graminearum assessed as mycelium growth inhibition at 50 ug/mL by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080775Fungicidal activity against Fusarium oxysporum assessed as mycelium growth inhibition by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID594248Antimicrobial activity against Fusarium omysporum by mycelium growth rate method2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.
AID1080784Fungicidal activity against Fusarium oxysporum assessed as mycelium growth inhibition at 50 ug/mL by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080781Fungicidal activity against Mycosphaerella arachidis assessed as mycelium growth inhibition at 50 ug/mL by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
AID1080777Fungicidal activity against Fusarium graminearum assessed as mycelium growth inhibition by mycelium growth rate method2009Journal of agricultural and food chemistry, Sep-09, Volume: 57, Issue:17
Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (66.67)29.6817
2010's3 (25.00)24.3611
2020's1 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.54

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 Index23.54 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.54)

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%
Other12 (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]		2.0110amino-acid anion
glutamine
Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.		2.1510amino acid zwitterion;
glutamine family amino acid;
glutamine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		7.1510glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
anthranilamide
[no description available]		2.0610substituted aniline
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		3.75100pyrrole;
secondary amine
3-o-methylglucose
3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.		2.1510D-aldohexose derivative
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.02101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
aminoimidazole carboxamide
Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.		2.0310aminoimidazole;
monocarboxylic acid amide		mouse metabolite
hydantoins
Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.		2.0310imidazolidine-2,4-dione
4-chloromercuribenzenesulfonate
4-Chloromercuribenzenesulfonate: A cytotoxic sulfhydryl reagent that inhibits several subcellular metabolic systems and is used as a tool in cellular physiology.		2.1510arenesulfonic acid;
arylmercury compound
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.1710glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
iprodione
iprodione : An imidazolidine-2,4-dione in which the nitrogen at position 1 is substituted by an N-(isopropyl)carboxamide group while that at position 3 is substituted by a 3,5-dichlorophenyl group. A contact fungicide, it blocks the growth of the fungal mycelium and inhibits the germination of fungal spores. It is used on fruit and vegetable crops affected by various fungal diseases. It is also used as a nematicide.		2.0310benzenes;
dichlorophenyl dicarboximide fungicide;
imidazole fungicide;
imidazolidine-2,4-dione;
ureas		antifungal agrochemical;
nematicide
vinclozolin
vinclozolin : A racemate comprising equimolar amounts of (R)- and (S)-vinclozolin. A fungicide used mainly on oilseed rape, vines, fruit and vegetables to control Botrytis, Sclerotinia and Monilia spp.. 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione : A member of the class of oxazolidinones that is 5-ethenyl-5-methyl-2,4-oxazolidinedione in which the imide hydrogen is replaced by a 3,5-dichlorophenyl group.		2.0210dicarboximide;
dichlorobenzene;
olefinic compound;
oxazolidinone
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.		2.1510D-glucopyranoseepitope;
mouse metabolite
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.17101,2,3-triazole
fludioxonil
fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.		2.0110benzodioxoles;
nitrile;
organofluorine compound;
pyrroles		androgen antagonist;
antifungal agrochemical;
estrogen receptor agonist
tolclofos-methyl
tolclofos-methyl: a fungicide used in the cultivation of cotton, sugar beets, and ornamental plants. tolclofos-methyl : An organic thiophosphate that is 2,6-dichloro-4-methylphenol in which the hydrogen of the hydroxy group group has been replaced by a dimethoxyphosphorothioyl group. Tolclofos-methyl is a phospholipid biosynthesis inhibitor and fungicide that is used for controlling soil-borne diseases caused by Typhula incarnata, Corticium rolfsii, Typhula ishikariensis, and Rhizoctonia solani.		2.0110dichlorobenzene;
organic thiophosphate		antifungal agrochemical
pencycuron
pencycuron: structure given in first source. pencycuron : A member of the class of phenylureas that is urea which is substituted by p-chlorobenzyl and cyclopentyl groups at position 1 and a phenyl group at position 3. A fungicide used to control diseases caused by Rhizoctonia solani and Pellicularia spp. It is not highly toxic to mammals but is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.		2.0110monochlorobenzenes;
phenylureas		antifungal agrochemical
eutypine
eutypine: isolated from Eutypa lata; structure in first source		2.0210
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		7.3110oxygen hydride;
oxygen radical;
reactive oxygen species
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		7.3110chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
resveratrol
trans-resveratrol : A resveratrol in which the double bond has E configuration.		710resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
stilbenes
Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.		210stilbene
oxamyl
oxamyl: RN given refers to parent cpd; structure		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials