Page last updated: 2024-12-06

isoprothiolane

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

Description

Isoprothiolane is a fungicide used to control diseases in various crops, including rice, wheat, and vegetables. Its synthesis involves a multi-step process starting from 2-chloro-4-nitroaniline. Isoprothiolane acts as a systemic fungicide, meaning it is absorbed by the plant and translocated throughout its system, offering protection against a wide range of fungal diseases. Its mode of action involves inhibiting the biosynthesis of ergosterol, an essential component of fungal cell membranes. This disruption disrupts fungal growth and development. The importance of isoprothiolane lies in its effectiveness against various fungal diseases, contributing to crop yield and quality. It is particularly effective against rice blast, a serious disease affecting rice production worldwide. Research on isoprothiolane focuses on understanding its efficacy, mode of action, environmental impact, and potential for resistance development in fungal pathogens. Continued research aims to optimize its application and develop sustainable strategies for fungal disease management.'

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

isoprothiolane : A malonate ester that is diisopropyl malonate in which the two methylene hydrogens at position 2 are replaced by a 1,3-dithiolan-2-ylidene group. An insecticide and fungicide used to control a range of diseases including Pyricularia oryzae, Helminthosporium sigmoideum and Fusarium nivale. [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 CID39681
CHEMBL ID35280
CHEBI ID6047
SCHEMBL ID71267
MeSH IDM0081646

Synonyms (51)

Synonym
BIDD:ER0504
propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester
di-isopropyl 1,3-dithiolane-2-ylidenemalonate
bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate
di(propan-2-yl) 1,3-dithiolan-2-ylidenemalonate
CHEBI:6047 ,
diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate
diisopropyl 1,3-dithiolan-2-ylidenemalonate
fudiolan
1,3-dithiolan-2-ylidenepropanedioic acid, bis(1-methylethyl) ester
nkk 100
nnf-109
ss 11946
isoprothiolane [bsi:iso]
brn 2128528
fuji 1
ipt (pesticide)
fujione
isoprothiolane
50512-35-1
CHEMBL35280
dipropan-2-yl 2-(1,3-dithiolan-2-ylidene)propanedioate
ufhlmyogrxocsl-uhfffaoysa-
inchi=1/c12h18o4s2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8h,5-6h2,1-4h3
2-(1,3-dithiolan-2-ylidene)propanedioic acid dipropan-2-yl ester
A828146
88hcs898g6 ,
unii-88hcs898g6
fuji-one
nnf 109
FT-0630634
AKOS015898851
isoprothiolane [iso]
propanedioic acid, 2-(1,3-dithiolan-2-ylidene)-, bis(1-methylethyl) ester
SCHEMBL71267
DTXSID8058110
diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate #
1,3-bis(propan-2-yl) 2-(1,3-dithiolan-2-ylidene)propanedioate
isoprothiolane, analytical standard
mfcd00210314
isoprothiolane 10 microg/ml in acetonitrile
isoprothiolane 10 microg/ml in cyclohexane
bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate, 9ci
diisopropyl (1,3-dithiolan-2-ylidene)malonate
AS-15491
Q18816455
A12577
CS-0013924
isoprothiolane 1000 microg/ml in acetone
fuji-one; ipt;nkk 100; nnf 109
HY-B1858

Research Excerpts

Actions

ExcerptReferenceRelevance
"Isoprothiolane was found to suppress the radial growth of AvrPik allele isolates at all concentrations (1, 5, 10, 15, and 20 μg/mL)."( Assessment of sensitivity and virulence fitness costs of the AvrPik alleles from Magnaporthe oryzae to isoprothiolane.
He, CP; Liang, YQ; Wang, L; Wu, WH; Yi, KX; Zhang, S; Zheng, XL, 2014
)
1.34

Dosage Studied

ExcerptRelevanceReference
" This study demonstrates that melatonin and isoprothiolane function synergistically and can be used to reduce the dosage and residual level of isoprothiolane, potentially contributing to the environment-friendly and sustainable control of crop diseases."( Melatonin targets MoIcl1 and works synergistically with fungicide isoprothiolane in rice blast control.
Bi, R; Cai, H; Chen, XL; Li, G; Li, Q; Li, R; Luo, CX; Sun, P; Teng, H; Wu, B; Xu, Z; Yang, W; Zhao, J; Zheng, L; Zhou, Y, 2023
)
1.41
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
insecticideStrictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
phospholipid biosynthesis inhibitorAny compound that inhibits the biosynthesis of any phospholipid.
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
malonate esterAn ester of malonic acid; any compound containing a malonate ester skeleton.
dithiolanes
isopropyl esterAny carboxylic ester resulting from the formal condensation of a carboxylic acid with the hydroxy group of propan-2-ol.
[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 (5)

Assay IDTitleYearJournalArticle
AID1081276Antifungal activity against Phomopsis asparagi by mycelium growth rate test2010Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5
Synthesis, fungicidal activity, and structure-activity relationship of spiro-compounds containing macrolactam (macrolactone) and thiadiazoline rings.
AID1081277Antifungal activity against Magnaporthe oryzae by mycelium growth rate test2010Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5
Synthesis, fungicidal activity, and structure-activity relationship of spiro-compounds containing macrolactam (macrolactone) and thiadiazoline rings.
AID1081279Antifungal activity against Sclerotinia sclerotiorum by mycelium growth rate test2010Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5
Synthesis, fungicidal activity, and structure-activity relationship of spiro-compounds containing macrolactam (macrolactone) and thiadiazoline rings.
AID1081280Antifungal activity against Botryotinia fuckeliana by mycelium growth rate test2010Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5
Synthesis, fungicidal activity, and structure-activity relationship of spiro-compounds containing macrolactam (macrolactone) and thiadiazoline rings.
AID1081278Antifungal activity against Rhizoctonia solani Kuhn by mycelium growth rate test2010Journal of agricultural and food chemistry, Mar-10, Volume: 58, Issue:5
Synthesis, fungicidal activity, and structure-activity relationship of spiro-compounds containing macrolactam (macrolactone) and thiadiazoline rings.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (19.35)18.7374
1990's7 (22.58)18.2507
2000's4 (12.90)29.6817
2010's9 (29.03)24.3611
2020's5 (16.13)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.70

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

MetricThis Compound (vs All)
Research Demand Index44.70 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index82.84 (26.88)
Search Engine Supply Index2.56 (0.95)

This Compound (44.70)

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%
Other32 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]