Acibenzolar-S-Methyl
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Basic Info
| Common Name | Acibenzolar-S-Methyl(F05024) |
| 2D Structure | |
| Description | Acibenzolar-S-methyl is a fungicide that works by activating a plant's own defense system by increasing the transcription of W-box controlled genes such as CAD1, NPR1 and PR2. It is a methyl derivative of acibenzolar. |
| FRCD ID | F05024 |
| CAS Number | 135158-54-2 |
| PubChem CID | 86412 |
| Formula | C8H6N2OS2 |
| IUPAC Name | S-methyl 1,2,3-benzothiadiazole-7-carbothioate |
| InChI Key | UELITFHSCLAHKR-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H6N2OS2/c1-12-8(11)5-3-2-4-6-7(5)13-10-9-6/h2-4H,1H3 |
| Canonical SMILES | CSC(=O)C1=C2C(=CC=C1)N=NS2 |
| Isomeric SMILES | CSC(=O)C1=C2C(=CC=C1)N=NS2 |
| Synonyms |
S-Methyl 1,2,3-benzothiadiazole-7-carbothioate
Acibenzolar-S-Methyl
Actigard
135158-54-2
Bendicar
Bion
Bion (pesticide)
BTH (agrochemical)
Acibenzolar-S-Methyl [ISO]
UNII-BCW6119347
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzothiadiazoles |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzothiadiazoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 1,2,3-benzothiadiazole - Thiobenzoic acid or derivatives - Benzenoid - Azole - Thiadiazole - Heteroaromatic compound - Carbothioic s-ester - Thiocarboxylic acid ester - Azacycle - Sulfenyl compound - Thiocarboxylic acid or derivatives - Carboxylic acid derivative - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzothiadiazoles. These are heterocyclic aromatic compounds containing a benzene ring fused to a thiadiazole ring. Thiadiazole is a five-membered aromatic heterocycle made up of one sulfur atom and two nitrogen atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 210.269 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 212 |
| Monoisotopic Mass | 209.992 |
| Exact Mass | 209.992 |
| XLogP | 2.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9668 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5410 |
| P-glycoprotein Substrate | Non-substrate | 0.7347 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8733 |
| Non-inhibitor | 0.9625 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8326 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5522 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7541 |
| CYP450 2D6 Substrate | Non-substrate | 0.8454 |
| CYP450 3A4 Substrate | Non-substrate | 0.6669 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8663 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8152 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8971 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8289 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5155 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9649 |
| Non-inhibitor | 0.9573 | |
| AMES Toxicity | Non AMES toxic | 0.6462 |
| Carcinogens | Non-carcinogens | 0.9148 |
| Fish Toxicity | High FHMT | 0.9466 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9441 |
| Honey Bee Toxicity | High HBT | 0.5539 |
| Biodegradation | Not ready biodegradable | 0.9367 |
| Acute Oral Toxicity | III | 0.4724 |
| Carcinogenicity (Three-class) | Non-required | 0.6425 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8698 | LogS |
| Caco-2 Permeability | 1.3302 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4010 | LD50, mol/kg |
| Fish Toxicity | 1.3998 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3840 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Peas (with pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260030 | European Union | 0.01* | 05/06/2018 | |
| Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,) | 0500040 | European Union | 0.01* | 05/06/2018 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 05/06/2018 | |
| Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba... | 0243020 | European Union | 0.01* | 05/06/2018 | |
| (a) grapes | 0151000 | European Union | 0.01* | 05/06/2018 | |
| Others (2) | 1016990 | European Union | 0.02* | 05/06/2018 | |
| (a) potatoes (Andigena,) | 0211000 | European Union | 0.01* | 05/06/2018 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 05/06/2018 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 05/06/2018 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 05/06/2018 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 05/06/2018 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 05/06/2018 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 05/06/2018 | |
| Others (2) | 0110990 | European Union | 0.01* | 05/06/2018 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 05/06/2018 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 05/06/2018 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 05/06/2018 | |
| Chestnuts | 0120040 | European Union | 0.01* | 05/06/2018 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 05/06/2018 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1 | 05/06/2018 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Control of Citrus Huanglongbing via Trunk Injection of Plant Defense Activatorsand Antibiotics. | Phytopathology | 2018 Feb | 28945516 |
| Heterogeneous Photochemistry of Agrochemicals at the Leaf Surface: A Case Studyof Plant Activator Acibenzolar-S-methyl. | J Agric Food Chem | 2017 Sep 6 | 28805053 |
| The impact of systemic and copper pesticide applications on the phyllospheremicroflora of tomatoes. | J Sci Food Agric | 2015 Mar 30 | 25410588 |
| Postharvest Survival of Porcine Sapovirus, a Human Norovirus Surrogate, onPhytopathogen-Infected Leafy Greens. | J Food Prot | 2015 Aug | 26219360 |
| Integrated approach to TYLCD management in Sardinia (Italy). | Commun Agric Appl Biol Sci | 2009 | 20222567 |
| Salicylate activity. 1. Protection of plants from paraquat injury. | J Agric Food Chem | 2005 Dec 14 | 16332128 |
Targets
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
- Gene Name:
- CYP2A6
- Uniprot ID:
- P11509
- Molecular Weight:
- 56501.005 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]