Acibenzolar-S-methyl

Acibenzolar-S-methyl
Skeletal formula of acibenzolar-S-methyl
Skeletal formula of acibenzolar-S-methyl
Space-filling model of the acibenzolar-S-methyl molecule
Names
Preferred IUPAC name
S-Methyl 1,2,3-benzothiadiazole-7-carbothioate
Other names
BTH, CGA245704
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.101.876 Edit this at Wikidata
EC Number
  • 420-050-0
MeSH S-methyl+benzo(1,2,3)thiadiazole-7-carbothioate
UNII
  • InChI=1S/C8H6N2OS2/c1-12-8(11)5-3-2-4-6-7(5)13-10-9-6/h2-4H,1H3 checkY
    Key: UELITFHSCLAHKR-UHFFFAOYSA-N checkY
  • InChI=1/C8H6N2OS2/c1-12-8(11)5-3-2-4-6-7(5)13-10-9-6/h2-4H,1H3
    Key: UELITFHSCLAHKR-UHFFFAOYAA
  • CSC(=O)c1cccc2nnsc12
  • CSC(=O)C1=C2SN=NC2=CC=C1
Properties[1]
C8H6N2OS2
Molar mass 210.27 g·mol−1
Appearance White to beige crystalline powder
Melting point 133 °C (271 °F; 406 K)
Boiling point 267 °C (513 °F; 540 K)
7.7 mg/L (20 °C)
log P 3.1
Hazards[2]
GHS labelling:
GHS07: Exclamation mark GHS09: Environmental hazard
Warning
H315, H317, H319, H335, H410
P261, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
Related compounds
Related compounds
 1,2,3-benzothiadiazole-7-carboxylic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acibenzolar-S-methyl is the ISO common name[3] for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.[4][5][6]

  1. ^ Pesticide Properties Database. "Acibenzolar-S-methyl". University of Hertfordshire.
  2. ^ "Acibenzolar-S-Methyl". US National Library of Medicine. Retrieved 2020-09-07.
  3. ^ "Compendium of Pesticide Common Names: acibenzolar". BCPC.
  4. ^ "Fact Sheet: Acibenzolar-S-Methyl" (PDF). EPA. 2000-08-11. Retrieved 2020-09-03.
  5. ^ Vlot, A.C.; Klessig, D.F.; Park, S.W. (August 2008). "Systemic acquired resistance, the elusive signal(s)". Current Opinion in Plant Biology. 11 (4): 436–442. doi:10.1016/j.pbi.2008.05.003. hdl:11858/00-001M-0000-0012-36EC-0. PMID 18614393.
  6. ^ Gozzo, Franco; Faoro, Franco (2013). "Systemic Acquired Resistance (50 Years after Discovery): Moving from the Lab to the Field". Journal of Agricultural and Food Chemistry. 61 (51): 12473–12491. doi:10.1021/jf404156x. PMID 24328169.