Benthiavalicarb isopropyl

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Tolerances are established for the combined residues of benthiavalicarb-isopropyl, isopropyl[(S)-1-[[[(1R)-1-(6-fluoro-2-benzothiazolyl)ethyl]amino] carbonyl]-2-methylpropyl]carbamate and isopropyl[(S)-1-[[[(1S)-1-(6-fluoro-2-benzothiazolyl)ethyl]amino] carbonyl]-2-methylpropyl]carbamate, in or on the following raw agricultural commodities: Note: There are no USA registrations as of July 30, 2006 [Table#7169]

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 121-258(2), indicate that benthiavalicarb isopropyl is expected to have high to moderate mobility in soil(SRC). Volatilization of benthiavalicarb isopropyl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.61X10-8 atm-cu m/mole(2). Benthiavalicarb isopropyl is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-10 mm Hg(SRC), determined from a fragment constant method(3). A biodegradation half-life of 11-19 days in soil(2) suggests that biodegradation may be an important environmental fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 121-258(2), indicate that benthiavalicarb isopropyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 8.61X10-8 atm-cu m/mole(2). According to a classification scheme(4), an estimated BCF of 17(SRC), from its log Kow of 2.52(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A biodegradation half-life of 11-19 days in soil(2) suggests that biodegradation may be an important fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benthiavalicarb isopropyl, which has an estimated vapor pressure of 5.4X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Benthiavalicarb isopropyl does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Benthiavalicarb-isopropyl is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

AEROBIC: Benthiavalicarb isopropyl readily degraded in aerobic soil, with a reported degradation half-life of 11-19 days at 20 °C(1).

ANAEROBIC: Benthiavalicarb isopropyl is degraded slowly in anaerobic soil, with a reported DT50 of 40 days at 20 °C(1).

An estimated BCF of 17 was calculated in fish for benthiavalicarb isopropyl(SRC), using a log Kow of 2.52(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Tolerances are established for the combined residues of benthiavalicarb-isopropyl, isopropyl[(S)-1-[[[(1R)-1-(6-fluoro-2-benzothiazolyl)ethyl]amino] carbonyl]-2-methylpropyl]carbamate and isopropyl[(S)-1-[[[(1S)-1-(6-fluoro-2-benzothiazolyl)ethyl]amino] carbonyl]-2-methylpropyl]carbamate, in or on the following raw agricultural commodities: Note: There are no USA registrations as of July 30, 2006 [Table#7170]

A new valinamide carbamate type of fungicide being proposed for use on grapes and tomatoes (both field and greenhouse) in the EU for the control of downy mildew; [HSDB] Proposed for use only on imported grapes and tomatoes; [Reference #1]

Farming (Pesticides) [Category: Industry]

Benthiavalicarb-isopropyl (... benthiavalicarb) is a new valinamide carbamate type of fungicide being proposed for use on grapes and tomatoes (both field and greenhouse) in the EU for the control of downy mildew.

Benthiavalicarb-isopropyl is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

A process for producing substituted alkylamines ... or salts thereof, characterized by reacting a metal salt of a 2-aminothiophenol derivative ... with an amino acid N-carboxyanhydride ... and cyclizing the obtained product under acidic conditions. By this process, substituted alkylamines typified by 1-(2-benzothiazolyl)alkylamines and salts thereof can be produced in high yields from 2-aminothiophenol derivatives on an industrial scale while keeping excellent handling properties. Even when the intended substituted alkylamine is an optically active compound, the intended product can be produced without reducing the optical purity of the optically active starting material.

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

... The R-L stereoisomer of benthiavalicarb (KIF-230RL) is the main and pesticidally active component; however, the S-L stereoisomer (KIF-230S-L), which is not pesticidally active, is also present as a minor impurity. The benthiavalicarb products being proposed for use in the EU on grapes and tomatoes include a 15% water-dispersible granule (WDG), for use only on tomatoes, and a multiple active ingredient WDG formulation containing both benthiavalicarb (1.75%) and mancozeb (70%) for use on both grapes and tomatoes. These formulations are labeled for multiple foliar applications. There are currently no food/feed uses or tolerances for benthiavalicarb in the U.S.