Benthiavalicarb isopropyl

381.47

381.46

605-799-5

AJ55PMS5IT

DTXSID9058232

White powder

109

2.52 to 2.59 at pH 5 to 9

1.25 g/cu cm at 20.5 deg C

152.0 °C

550.6±40.0 °C(Predicted)

286.8±27.3 °C

1.559

In water (20 deg C), 10.96 mg/L at pH 5; 13.14 mg/L at unadjusted pH; 12.76 mg/L at pH 9

5.38X10-10 mm Hg at 25 deg C (est)

Henry's Law constant = 8.61X10-8 atm-cu m/mol at 25 °C (8.72X10-3 Pa-cu m/mol)

No dissociation from pH 1.12 to 12.81 at 20 °C

Hydroxyl radical reaction rate constant = 5.49X10-11 cu cm/molec-sec at 25 °C (est)

FB1330000

P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P405, P501

H317

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.

U.S. Environmental Protection Agency, Office of Prevention, Pesticides and Toxic Substances; Fact Sheet for Benthiavalicarb-Isopropyl. New Tolerances Established. 16 p. (August 2006)|U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Benthiavalicarb-Isopropyl: Human Health Risk Assessment for Proposed Uses on Imported Grapes and Tomatoes. 87 p. (June 29, 2006)

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 227 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

LD50 Rat oral >2,000 mg/kg

Benthiavalicarb isopropyl's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).

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 stable in water(1). Benthiavalicarb isopropyl does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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).

The Koc values of benthiavalicarb isopropyl of 121-258 have been reported(1). According to a classification scheme(2), this estimated Koc value suggests that benthiavalicarb isopropyl is expected to have high to moderate mobility in soil.

The Henry's Law constant for benthiavalicarb isopropyl is estimated as 8.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that benthiavalicarb isopropyl is expected to be essentially nonvolatile from water surfaces(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).

Occupational exposure to benthiavalicarb isopropyl may occur through inhalation and dermal contact with this compound at workplaces where benthiavalicarb isopropyl is produced or used. (SRC)

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

During a metabolism study in rats, both the low and high dose radiolabeled forms were absorbed rapidly, with nearly full recovery of radioactive label (89-100%) within 168 hours. Radioactivity was recovered primarily in the feces (62-83%) and urine (7-24%), with up to 85% recovery in 48 hours. Urinary excretion was slightly higher in females than males. Absorption was greater in the low dose group than in the high dose group, indicating incomplete absorption in the high dose group. Radiolabeled residues preferentially partitioned into plasma. In both dose groups (at all time points), the concentration of radioactivity was higher in the kidneys and liver than it was in plasma.

Analysis of the metabolites in bile, urine, and feces of cannulated rats identified a total of 13 compounds, including the parent, which accounted for 43-60% of the radiolabeled dose. The metabolite profile was similar between the sexes. A total of 11 metabolites were identified in the urine, most present in concentrations <2% of the administered dose. A total of 8 metabolites were found in the bile, with the principal metabolites being isomers of hydroxylated glutathione conjugates and a glucuronide conjugate. Parent compound was not present in the urine or bile. Based upon the components identified in excreta, the metabolism of benthiavalicarb in rats primarily involves either hydroxylation of the phenyl ring followed by glucuronic acid conjugation or glutathione conjugation and hydroxylation of the phenyl ring with subsequent degradation of the glutathione moiety, resulting in a variety of metabolites present in small quantities. Cleavage and hydroxylation of the valyl side chain also occurs to a limited extent. Parent (excreted in feces only) and metabolites, M15 (urine and feces) and M18 (urine only), were also the principal components detected in plasma, liver, and kidneys.|In grapes and tomatoes, the metabolism of benthiavalicarb was minimal with parent being the only major residue in fruit and foliage (55-95% TRR). Parent was also the principal 14C-residue in potato foliage (88-90% TRR), but other minor metabolites were identified. In potatoes, the metabolism of benthiavalicarb occurs primarily via direct hydroxylation of the phenyl ring or defluorination and hydroxylation of the phenyl ring. Secondary metabolism occurs via conjugation of sugars. Chiral analysis of potato foliage extracts also indicates that there was no isomeric conversion of the active R-L isomer to other possible isomers (S-L, R-D, or S-D) ... The metabolism of benthiavalicarb is more extensive in rats than it is in grapes, tomatoes, and potatoes. In all plant species tested, metabolism of parent benthiavalicarb occurred to a very limited extent. In both plants and animals, the primary metabolic pathways are hydroxylation of the phenyl ring with subsequent conjugation with sugars or glutathione. The only metabolic pathway occurring in plants that did not occur in rats was the defluorination that occurred in potatoes.

/Target Species/ Its mode of action is through the inhibition of phospholipid biosynthesis.|Mechanism Study of Thyroid Tumors in Rats. 12 male Fisher rats/sex/dose were fed KIF- 230 in their diets at concentrations of 0, 13.3, or 661.4 mg/kg/day for 14 days. The data indicated that the administration of KIF-230 in the diet at a dose of 661.4 mg/kg/day resulted in decreased serum T4 levels (11-18%) in male rats. Absolute and relative-to-body liver weights were increased (22-24%) compared to controls, and macroscopic examination revealed enlarged liver in all rats in this dose group, which is consistent with enzyme induction. TSH levels were non-significantly increased compared to controls, and T3 levels remained similar to controls. The observed increase in UDP-GT activity (16%) on T4 could cause a decrease in circulating T4 levels, resulting in increased serum TSH levels via a feedback mechanism. This mechanism could ultimately cause hyperthyroidism following a sufficient duration of exposure in rats.|Mechanism Study of Thyroid Tumors in Mice. 12 Scl:B6C3F1 male mice/dose were exposed to KIF-230 in their diet at concentrations of 0, 17.0, or 855.0 mg/kg/day for 14 days. No effects were observed on mortality, clinical observations, body weights, cumulative body weight gains, or food consumption. Increased absolute and relative liver weights were observed at 855 mg/kg/day, which is consistent with enzyme induction and the increased UDP-GT activity on T4 seen in this study. While serum T4 levels were decreased 25-29%, T3 and TSH remained similar to controls throughout the study. Typical UDP-GT inducers are known to cause hyperthyroidism by inducing TSH through a decrease in serum thyroid hormone levels; and thyroid hyperplasia is a potential mechanism for the induction of thyroid tumors. The lack of an appropriate antibody (anti-mouse TSH) could cause inaccurate measurements of TSH in the radioimmunoassay used to determine serum levels of TSH. While the mechanism is plausible, no definitive conclusions can be reached concerning this mechanistic study.

((1S)-1-((((1R)-1-(6-fluoro-2-benzothiazolyl)ethyl)amino)carbonyl)-2-methylpropyl)carbamic acid

... 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.

Analyte: benthiavalicarb-isopropyl; matrix: soil; procedure: high-performance liquid chromatography; quantitation limit: 0.01-0.02 mg/kg

Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Benthiavalicarb has known environmental transformation products that include M-1, M-3, M-4, M-5, and M-8.