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Home > Encyclopedia > Acibenzolar-S-methyl

Acibenzolar-S-methyl

Acibenzolar-S-methyl structure

Acibenzolar-S-methyl 

structure
  • CAS No:

    135158-54-2

  • Formula:

    C8H6N2OS2

  • Chemical Name:

    Acibenzolar-S-methyl

  • Synonyms:

    1,2,3-Benzothiadiazole-7-carbothioic acid,S-methyl ester;CGA 245704;Actigard;Benzothiadiazole;BTH;Acibenzolar-S-methyl;Bendicar;Bion;Bion (pesticide);BTH (agrochemical);Bion 50WG;Bion 49;Actigard AM 87;Bion 500WG;1135442-78-2

  • Categories:

    Agrochemicals  >  Fungicides

Description

ChEBI: A benzothiadiazole that is the S-methyl thioester derivative of acibenzolar. It is used as a fungicide and plant activator on a variety of crops, including cotton, chili peppers, lettuce, onions, spinach, tobacco, and tomatoes.


Acibenzolar-S-methyl is 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. It has a role as a plant activator, an antifungal agrochemical and a profungicide. It is a benzothiadiazole and a thioester. It derives from an acibenzolar.

Acibenzolar-S-methyl Basic Attributes

226.34

210.28

420-050-0

BCW6119347

DTXSID1032519

White to beige fine powder

Characteristics

96.4

3.1 @ 25 deg C

Beige fine powder

1.54X10+3 g/cu cm @ 22 deg C

132.9 °C

267 °C (approx)

154.5ºC

1.5690 (estimate)

In water, 7.7 mg/l @ 25 deg C

0-6°C

4.4 x 10 -4 Pa (25 °C)

LD50 in rats (mg/kg): >2000 orally; >2000 dermally (Ruess)

Burnt-like odor|Odorless

Stability: hydrolysis DT50 (20 °C) 3.8 yr (pH 5), 23 weeks (pH 7), 19.4 hr (pH 9).

Safety Information

UN 3077 9 / PGIII

3

36/37/38-43-50/53

24/25-37-46-59-60-61

Xi,N

P261-P273-P280-P305 + P351 + P338-P501

H315-H317-H319-H335-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, 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, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 195 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

LD50 Rat oral >5000 mg/kg (90-day subchronic rat feeding)

Acibenzolar-S-methyl's production may result in its release to the environment through various waste streams; it's use as a plant activator(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a log Kow of 3.10(2) and a regression-derived equation(3), indicates that acibenzolar-S-methyl is expected to have low mobility in soil(SRC). Volatilization of acibenzolar-S-methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 3.3X10-6 mm Hg(2), and water solubility, 7.7 mg/l(2). Acibenzolar-S-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation in soil may be an important environmental fate process with a half-life of 5 hrs reported; the major metabolite was benzo(1,2,3)thiadiazole-7-carboxylic acid(4). The compound has been reported to dissipate in soil via hydrolysis, with a half-life of 0.3 days(2). Degradation by photolysis on soil was rapid, rate not indicated, at environmental pH's of 6 to 9(4). The major metabolite was benzo(1,2,3)thiadiazole-7-carboxylic acid in hydrolysis and soil photolysis studies(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,200(SRC), determined from a log Kow of 3.10(2) and a regression-derived equation(3), indicates that acibenzolar-S-methyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-17 atm-cu m/mole(SRC), derived from its vapor pressure, 3.30X10-6 mm Hg(2), and water solubility, 7.7 mg/l(2). According to a classification scheme(4), an estimated BCF of 49(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation in water may be an important environmental fate process with a half-life of 1 day reported; the major metabolite was benzo(1,2,3)thiadiazole-7-carboxylic acid(6). The hydrolysis half-life in water is <1 day(2). Degradation by photolysis in water was rapid, rate not indicated, at environmental pH's of 6 to 9(6). The major metabolite was benzo(1,2,3)thiadiazole-7-carboxylic acid in alhthough considerably less metabolite apparent than that produced in soil photolysis tests(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acibenzolar-S-methyl, which has a vapor pressure of 3.30X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acibenzolar-S-methyl is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 48 hrs(SRC), calculated from its rate constant of 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase acibenzolar-S- methyl may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of acibenzolar-S-methyl with photochemically-produced hydroxyl radicals has been estimated as 7.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 48 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The hydrolysis half-life in natural water was <1 day, with an 8 day half-life reported for the primary hydrolysis product(2). Acibenzolar-S-methyl is rapidly hydrolyzed in soils, with a half-life of 0.3 days; metabolites decome completly degraded and mineralized(2). The major metabolite was benzo(1,2,3)thiadiazole-7-carboxylic acid in hydrolysis and soil photolysis studies(3). Degradation by photolysis in water and on soil was rapid, rate not indicated, at environmental pH's of 6 to 9(3).

An estimated BCF of 49 was calculated for acibenzolar-S-methyl(SRC), using a log Kow of 3.10(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc of acibenzolar-S-methyl is estimated as 1,200(SRC), using a log Kow of 3.10(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that acibenzolar-S-methyl is expected to have low mobility in soil.

The Henry's Law constant for acibenzolar-S-methyl is estimated as 1.2X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 3.30X10-6 mm Hg(1), and water solubility, 7.7 mg/l(1). This Henry's Law constant indicates that acibenzolar-S-methyl is expected to be essentially nonvolatile from water surfaces(2). Acibenzolar-S-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2).

Occupational exposure to acibenzolar-S-methyl may occur through inhalation of dust and dermal contact with this compound at workplaces where acibenzolar-S-methyl is produced or used. (SRC)

Drug Information

Following oral treatment of rats, acibenzolar-S-methyl was rapidly & nearly completely (>90% of admin dose) absorbed from the GI tract into the general circulation. The majority (88-95%) of the admin dose was excreted in the urine within the first 48 hr. The major metabolite (79-92%) in the urine was the carboxylic acid derivative of the parent.

Following oral treatment of rats, ... the major metabolite (79-92%) in the urine was the carboxylic acid derivative of the parent.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

acibenzolar-S-methyl

Acibenzolar-S-methyl Use and Manufacturing

Methods of Manufacturing

Prepn: R. Schurter et al., EP 313512; eidem US 5523311 (1989, 1996 both to Ciba-Geigy).

Uses

Plant disease resistance activator.

Water dispersible granules|50% active ingredient

Agrochemicals -> Plant Activators|Plant activators, Fungicides, Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Acibenzolar-S-Methyl has known environmental transformation products that include CGA210007 and SYN546642.

Computed Properties

Molecular Weight:210.3
XLogP3:2.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:209.99215517
Monoisotopic Mass:209.99215517
Topological Polar Surface Area:96.4
Heavy Atom Count:13
Complexity:212
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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