Page last updated: 2024-12-07

s-methyl benzo(1,2,3)thiadiazole-7-carbothioate

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

Description

S-methyl benzo(1,2,3)thiadiazole-7-carbothioate: induces system acquired resistance in wheat; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID86412
CHEMBL ID425055
CHEBI ID73178
SCHEMBL ID50864
MeSH IDM0260899

Synonyms (53)

Synonym
bth (agrochemical)
actigard
acibenzolar-s-methyl [iso]
bion
bendicar
1,2,3-benzothiadiazole-7-carbothiolic acid, s-methyl ester
cga 245704
hsdb 7021
einecs annex i index 016-083-00-1
bion (pesticide)
ASM ,
acibenzolar-s-methyl
135158-54-2
s-methyl 1,2,3-benzothiadiazole-7-carbothioate
NCGC00168291-01
chebi:73178 ,
CHEMBL425055
NCGC00168291-02
ec 420-050-0
benz(1,2,3)thiadiazole-7-carbothioic acid-s-methyl ester
benzo(1,2,3)thiadiazole-7-carbothioic acid s-methyl ester
1,2,3-benzothiadiazole-7-carbothioic acid, s-methyl ester
unii-bcw6119347
gga 245704
ccris 9239
bcw6119347 ,
s-methyl benzo(1.2.3)thiadiazole-7-carbothioate
dtxcid9012519
dtxsid1032519 ,
cas-135158-54-2
tox21_300864
NCGC00254768-01
s-methyl benzo[1,2,3]thiadiazole-7-carbothioate
1,2,3-benzothiadiazole-7-carboxlic acid thiomethyl ester
benzo-(1,2,3)-thiadiazole-7-carbothioic acid s-methyl ester
7-(methylthiocarbonyl)-benzo-1,2,3-thiadiazole
AKOS015904137
1,2,3-benzothiadiazole-7-carbothioic acid s-methyl ester
s-methyl benzo(1,2,3)thiadiazole-7-carbothioate
acibenzolar-s-methyl [hsdb]
acibenzolar-s-methyl [mi]
SCHEMBL50864
acibenzolar s-methyl
acibenzolar-s-methyl, pestanal(r), analytical standard
acibenzolar-s-methyl 10 microg/ml in cyclohexane
bth derivative
benzothiadiazole derivative
benzo(1,2,3)-thiadiazole-7-carbothioic acid s-methyl ester
J-006653
pesticide5_acibenzolar-s-methyl_c8h6n2os2_actigard
Q341312
acibnzolar-s-methyl
bion, bth

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response and time course experiments revealed a similar pattern of transcript accumulation and lipoxygenase activity in BTH-treated rice leaves."( Characterization of RCI-1, a chloroplastic rice lipoxygenase whose synthesis is induced by chemical plant resistance activators.
Dudler, R; Schaffrath, U; Zabbai, F, 2000
)
0.31
"Soil drenches of SA and INA and root dip application of SA and BTH inhibited nematode reproduction, at specific dosage ranges, without affecting plant growth."( Systemic acquired resistance activation in solanaceous crops as a management strategy against root-knot nematodes.
Molinari, S, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
plant activatorAny compound that protects plants by activating their defence mechanisms.
antifungal agrochemicalAny substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
profungicideA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active fungicide for which it is a profungicide.
[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 (2)

ClassDescription
benzothiadiazole
thioesterA compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'.
[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]

Pathways (2)

PathwayProteinsCompounds
methylsalicylate degradation17
superpathway of methylsalicylate metabolism311

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency51.70990.002541.796015,848.9004AID1347395; AID1347397; AID1347398
pregnane X receptorRattus norvegicus (Norway rat)Potency56.23410.025127.9203501.1870AID651751
GLI family zinc finger 3Homo sapiens (human)Potency48.55770.000714.592883.7951AID1259392
AR proteinHomo sapiens (human)Potency14.52030.000221.22318,912.5098AID1259243; AID1259247
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency15.45720.001022.650876.6163AID1224838; AID1224893
progesterone receptorHomo sapiens (human)Potency54.48270.000417.946075.1148AID1346795
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID1104767Antifungal activity against Botryotinia fuckeliana infected grape assessed as decrease in lesion diameter at 1 mg/ml applied by dipping 24 hr prior to infection measured after 4 days at 4 degC relative to untreated-control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1104777Growth inhibition of Botryotinia fuckeliana at 0.5 mg/ml after 4 days relative to control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092019Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 100 ug/mL compound through leaf spray followed by 7 days culture under green house conditions assessed as inhibition of viral growth in leaves infect2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092024Antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 10 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104770Antifungal activity against Botryotinia fuckeliana infected in grape assessed as lesion diameter at 1 mg/ml applied by dipping 24 hr prior to infection measured after 4 days at 24 degC (Rvb = 30.56 mm)2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092029In vivo antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 500 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092028In vivo antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 1000 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID264707Induction of systemic acquired resistance of tobacco plant against TMV at 100 ug/ml by soil treatment2006Bioorganic & medicinal chemistry letters, May-15, Volume: 16, Issue:10
Discovery of bitriazolyl compounds as novel antiviral candidates for combating the tobacco mosaic virus.
AID1092023In vivo antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 10 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092021Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 1000 ug/mL compound through leaf spray followed by 7 days culture under green house conditions assessed as inhibition of viral growth in leaves infec2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092017Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 10 ug/mL compound through leaf spray followed by 7 days culture under green house conditions assessed as inhibition of viral growth in leaves infecte2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1102593Induction of N-gene mediated systemic acquired resistance against TMV in Nicotiana tabacum cv. Xanthi nc (tobacco) assessed as decrease in lesion size at 0.1 mg/pot applied by soil-drench 5 days prior to infection measured after 5 days relative to control2003Bioscience, biotechnology, and biochemistry, Dec, Volume: 67, Issue:12
Pyrazolecarboxylic acid derivative induces systemic acquired resistance in tobacco.
AID1092018Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 50 ug/mL compound through leaf spray followed by 7 days culture under green house conditions assessed as inhibition of viral growth in leaves infecte2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092027In vivo antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 50 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID264706Induction of systemic acquired resistance of tobacco plant against TMV at 100 ug/ml by leaf spray treatment2006Bioorganic & medicinal chemistry letters, May-15, Volume: 16, Issue:10
Discovery of bitriazolyl compounds as novel antiviral candidates for combating the tobacco mosaic virus.
AID1092031Antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 500 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092020Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 500 ug/mL compound through leaf spray followed by 7 days culture under green house conditions assessed as inhibition of viral growth in leaves infect2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104776Growth inhibition of Botryotinia fuckeliana at 1 mg/ml after 4 days relative to control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1104774Antifungal activity against Botryotinia fuckeliana assessed as mycelial growth at 3 mg/ml after 4 days (Rvb = 85 mm)2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092013Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 100 ug/mL compound through irrigation based soil treatment followed by 7 days culture under green house conditions assessed as inhibition of viral gr2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092033Antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 50 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104764Antifungal activity against Botryotinia fuckeliana infected grape assessed as decrease in lesion diameter at 1 to 3 mg/ml applied by dipping 24 hr prior to infection measured after 5 to 7 days at 4 degC relative to untreated-control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1104775Antifungal activity against Botryotinia fuckeliana assessed as mycelial growth at 2 mg/ml after 4 days (Rvb = 85 mm)2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092014Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 500 ug/mL compound through irrigation based soil treatment followed by 7 days culture under green house conditions assessed as inhibition of viral gr2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104771Antifungal activity against Botryotinia fuckeliana assessed as mycelial growth after 4 days2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1104773Growth inhibition of Botryotinia fuckeliana at 4 mg/ml after 4 days relative to control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1102607Induction of systemic acquired resistance against Oidium in Nicotiana tabacum cv. Xanthi nc (tobacco) assessed as decrease in lesion size applied as soil-drench 5 days prior to infection measured after 5 days2003Bioscience, biotechnology, and biochemistry, Dec, Volume: 67, Issue:12
Pyrazolecarboxylic acid derivative induces systemic acquired resistance in tobacco.
AID1104768Antifungal activity against Botryotinia fuckeliana infected grape assessed as decrease in lesion diameter at 3 mg/ml applied by dipping 24 hr prior to infection measured after 3 days at 24 degC relative to untreated-control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092032Antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 100 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104765Antifungal activity against Botryotinia fuckeliana infected grape assessed as decrease in lesion diameter at 3 mg/ml applied by dipping 24 hr prior to infection measured after 3 days at 4 degC relative to untreated-control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1092011Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 10 ug/mL compound through irrigation based soil treatment followed by 7 days culture under green house conditions assessed as inhibition of viral gro2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104766Antifungal activity against Botryotinia fuckeliana infected grape assessed as decrease in lesion diameter at 3 mg/ml applied by dipping 24 hr prior to infection measured after 4 days at 4 degC relative to untreated-control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1104769Antifungal activity against Botryotinia fuckeliana infected grape assessed as lesion diameter at 3 mg/ml applied by dipping 24 hr prior to infection measured after 4 days at 24 degC (Rvb = 30.56 mm)2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
AID1091989Antifungal activity against Puccinia triticina inoculated on 500 ug/mL compound pre-treated wheat plants with 3 to 5 leaves assessed as growth inhibition2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092015Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 1000 ug/mL compound through irrigation based soil treatment followed by 7 days culture under green house conditions assessed as inhibition of viral g2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092012Induction of systemic acquired resistance against Tobacco mosaic virus (TMV) in tobacco plants exposed to 50 ug/mL compound through irrigation based soil treatment followed by 7 days culture under green house conditions assessed as inhibition of viral gro2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092026Antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 1000 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1092030In vivo antiviral activity against Tobacco mosaic virus (TMV) infected tobacco leaves exposed to 100 ug/mL for 20 min assessed as inhibition of viral growth measured 72 hr post compound treatment compound by half-leaf juice rubbing method2009Journal of agricultural and food chemistry, May-27, Volume: 57, Issue:10
Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance.
AID1104772Growth inhibition of Botryotinia fuckeliana at 5 mg/ml after 4 days relative to control2010Pest management science, Sep, Volume: 66, Issue:9
Sensitivity of Botrytis cinerea to chitosan and acibenzolar-S-methyl.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (94)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.06)18.7374
1990's1 (1.06)18.2507
2000's33 (35.11)29.6817
2010's37 (39.36)24.3611
2020's22 (23.40)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.34

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

MetricThis Compound (vs All)
Research Demand Index11.34 (24.57)
Research Supply Index4.58 (2.92)
Research Growth Index5.93 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.34)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.03%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other96 (98.97%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]