2439-01-2Cc1ccc2nc3sc(=O)sc3nc2c1FBQQHUGEACOBDN-UHFFFAOYSA-NOxythioquinox (Chinomethionat) can cause cancer and developmental toxicity according to The Environmental Protection Agency (EPA).
2439-01-2DTXSID2032342CHEMBL1595865CHEBI:34620Acaricides, Fungicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Other Insecticides
Pesticide (Oxythioquinox) -> USDA PDB
log Kow = 3.78 at 20 °C
3.78
Solubility (g/L at 20 °C) in: toluene, 25; dichloromethane, 40; hexane, 1.8; isopropanol, 0.9; cyclohexanone, 18; dimethylformamide, 10; petroleum oils, 4
In water, 1 mg/L at 20 °C
0.0000002 [mmHg]
0.026 mPa (2.0X10-7 mm Hg) at 20 °C
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Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Hazard Traits - Carcinogenicity; Developmental Toxicity
2002/2076
REACH registered substance: Chinomethionate (EC: 219-455-3)
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
May cause skin irritation (especially in the presence of water); [HSDB] An eye irritant; May cause skin sensitization; [eChemPortal: ESIS] An eye irritant; May cause skin sensitization; Effects in high-dose animal studies include convulsions; [MSDSonline]
The degradation of quinomethionate (q), used as a fungicide on cucumbers, by geen algae, ankistrodesmus falcatus isolated from seeds of a cucumber culture, was studied. The algae actively decomposed q to CO2. One of two intermediary metabolites of q resulting from biohalogenation was 6-meta-2-amino-3-chloroquinoxaline, which is highly toxic to plants.
In rats, following oral administration, chinomethionat is rapidly metabolised, and about 90% is eliminated within 3 days in the feces and urine. The main metabolite is chinomethionat acid (dimethylmercaptoquinoxaline-6-carboxylic acid), which also occurs in the conjugated form.
When rats were fed carbonyl-14C-labelled oxythioquinox. It was found that most of the radioactivity was exhaled as 14CO2. After 2,3-14C- and 35S-labelled active ingredient was fed to rats, no 14CO2 was found in the air expired. In this particular case, most of the activity was present in the urine and in the feces. A small proportion of the activity was found in the blood plasma in protein-bound form. The activity is not present as oxythioquinox itself, but partially as 2,3-dithiol-6-methyl quinoxaline, in traces as the corresponding dihydroxy compound, and as other still unidentified metabolites. The quinoxaline ring is apparently not metabolized in the animal body.
... The biological half-life determination show that plasma Morestan 35S is eliminated very slowly.
After intragastric administration of (35)S-labeled oxythioquinox, it forms a complex with plasma protein, particularly albumins, in vivo and in vitro. Elimination was slow after iv administration. Morestan concentration in plasma and peripheral compartment was in equilibrium.
Oxythioquinox was shown to be irreversibly bound to bovine serum albumin and to proteins in spider mite homogenate and in rat brain, liver and blood. The binding to proteins probably involved a mechanism by which SH-group of proteins initially attacks CO-group of oxythioquinox.
Both Morestan and 6-methyl-2,3-quinoxalinedithiol (a possible metabolite) were poorly absorbed from the gastrointestinal tracts of rats and mice.
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Chinomethionat appears as yellow crystals. Non-corrosive. Used as a selective fungicide.
Yellow solid; [Merck Index]
Chinomethionate is a tan to yellow crystals. Soluble in benzene, toluene, and dioxane; insoluble in water. It has been shown to have low toxicity to mammals, birds and bees, but is highly toxic to fish and some aquatic invertebrates.
On February 1, 1999, Bayer requested voluntary cancellation of all the remaining Morestan products, contingent upon an 18-month existing stock provision which would allow them to deplete their remaining product inventory. EPA published a notice of receipt of Bayer's request for voluntary termination of oxythioquinox registrations in the Federal Register on March 17, 1999. The cancellation notice was published September 17, 1999. Per Bayer's request, the registrant will be allowed to sell and distribute existing stocks of these products for eighteen months after the effective date of cancellation, or until March 17, 2001. End-users will be allowed an additional year, until September 17, 2001 (for a total of 2 years beyond the registrant's requested date), for the use of existing stocks.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Oxythioquinox is found on List B. Case No: 2495; Pesticide type: Insecticide, fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 6-Methyl-2,3-quinoxalinedithiol cyclic S,S-dithiocarbonate; Data Call-in (DCI) Date(s): 02/21/91, 10/13/95; AI Status: The producer of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Acute Tox. 4 (100%)
Reproductive toxicity - category 2
Acute toxicity (Inhalation: Dusts and mists) - Category 4
Hazardous to the aquatic environment (Acute) - Category 1
Repr. 2
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.
A minor antagonism occurred between the effects of lipids and those of oxythioquinox, both administered in the diets of rats.
Pretreatment with phenobarbital 50 mg/kg intraperitoneally daily for five days decreased the toxicity of morestan to adult males and increased the toxicity to adult females.
Increase toxicity of oxythioquinox in oil solution to male swiss mice & Sprague-Dawley rats is due to increase resorption during protracted intestinal passage.
Administered to rats by stomach tubing oxythioquinox (Morestan) toxicity is very strongly increased after solubilisation in olive oil. The oxythioquinox LD50, in this case, is 500 mg/kg although ... 2.8 g/kg in aqueous suspensions /can be reached/. When it is administered (1 g/kg) in aqueous suspension, the decrease in body weight is the same as these observed with a 5 fold lower dose in oil. Conversion rate feed and weight of different organs decrease when animals are daily submitted to oxythioquinox in oil, during 16 days, compared with animals treated with an equivalent dose in aqueous suspension. Potentiation, in oil solutions, of the decrease of oxythioquinox intestinal transit, promoting its absorption, could explain the increase of oxythioquinox toxicity in oil solution.
For more Interactions (Complete) data for OXYTHIOQUINOX (6 total), please visit the HSDB record page.
LD50 Agelaius phoeniceus (Red-winged blackbird) oral >500 mg/kg
LC50 Anas platyrhynchos (Mallard duck, 1 day) dietary >5000 ppm/8 days
LD50 Apis mellifera (Honey bee, worker) topical 66.47 ug/bee/48 hr
LD50 Colinus virginianus (Northern bobwhite) oral 196 mg/kg
For more Ecotoxicity Values (Complete) data for OXYTHIOQUINOX (12 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 2,300 to 28,235 (2,3), indicate that oxythioquinox is expected to have slight to no mobility in soil(SRC). Volatilization of oxythioquinox from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure 2.0X10-7 mm Hg(4), and water solubility, 1 mg/L(4). Oxythioquinox is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A photolysis rate of 0.014 per day has been reported for oxythioquinox on soil(3), which corresponds to a half-life of 50 days(SRC). In moist alkaline soils, hydrolysis is expected to be an important fate process based on hydrolysis half-lives of 10 days, 80 hours, and 225 minutes that have been reported for oxythioquinox at 22 °C and pH 4, 7, and 9, respectively(4). Field dissipation half-lives of 2.0-3.6 days have been reported for oxythioquinox in two sandy loam soils(3). A half-life of 3.7 days was reported for oxythioquinox in sandy loam soil under anaerobic conditions(3).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 2,300 to 28,235(2,3), indicate that oxythioquinox is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 6.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0X10-7 mm Hg(5), and water solubility, 1 mg/L(5). According to a classification scheme(6), an estimated BCF of 160(SRC), from its log Kow of 3.78(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Hydrolysis half-lives of 10 days, 80 hours, and 225 minutes have been reported for oxythioquinox at 22 °C and pH 4, 7, and 9, respectively(5). A photolysis rate of 1.260 per day has been reported for oxythioquinox in water, which corresponds to a half-life of 0.5 day(3).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oxythioquinox, which has a vapor pressure of 2.0X10-7 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase oxythioquinox 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 4.8 days(SRC), calculated from its rate constant of 3.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase oxythioquinox may be removed from the air by wet and dry deposition(SRC). Oxythioquinox may be susceptible to direct photolysis by sunlight(SRC) based on experiments that found that it decomposed in benzene solution upon irradiation with long wavelengths (>290 nm)(4).
Oxythioquinox was detected in pears in 1 of 571 samples at 0.04 ppm in an US Food and Drug Administration (FDA) regulatory monitoring study of domestic foods that may be eaten by infants/children, 1985-1991(1). Oxythioquinox was not detected (general detection limit 0.05 ppm) in foods that were part of the Danish National Pesticide Monitoring Program 1995-1996; analysis for oxythioquinox was performed in fruits and vegetables(2). Oxythioquinox was detected at 0.03 ppm fresh weight in 1 of 10 samples of fresh strawberries from markets in Nara, Japan (Jan-Mar 1992); oxythioquinox was not detected in 10 strawberry samples obtained from markets in Nara, Japan (Jan-Mar 1993)(3). Oxythioquinox was not detected (detection limit 0.01 ppm) in a monitoring study in Japan of 10 kinds of agricultural products (brown rice, potato, cabbage, lettuce, carrot, cucumber, shiitake mushroom, apple, strawberry, and banana)(4). Oxythioquinox was reported as detectable in domestic and imported pears that were part of the US FDA Pesticide Program (1992-93)(5). Oxythioquinox was detected in <1% of 769 samples of domestic apples that were part of the US FDA Pesticide Program (1993-94) at a maximum concentration of 0.05 ppm (6).
Chemical residue analyses indicated that initial deposits of oxythioquinox were about 4-14 ppm with a half-life of 34 to 37 days for both lemons and oranges(1). Residues of oxythioquinox are readily washed off fruit by rains or washing; oxythioquinox residues largely remain on the fruit surface rather than penetrate into the wax or the rind(1).
Koc values ranging from 2,300 to 28,235 have been reported for oxythioquinox on various soil types(1,2). According to a classification scheme(3), this estimated Koc value suggests that oxythioquinox is expected to have slight to no mobility in soil. The mobility of oxythioquinox was tested in a soil thin-layer chromatographic system using Hagerstown silty clay loam (surface soil with 2.5% organic material, 39.5% clay, soil water content is 34.1%, pH is 6.8)(4). Oxythioquinox was immobile by both autoradiographic and bioassay visualization using the TLC system indicating strong absorption to the soil medium(4).
/HUMAN EXPOSURE STUDIES/ Compressions containing dry or moist oxythioquinox were applied to the forearms of 9 human volunteers for varying periods of 2, 4, 8 or 24 hours. Exposures for 24 hours resulted in reddening of the skin and occasional swelling and blistering, the incidence and severity of these injuries being more marked with the moist product.
/HUMAN EXPOSURE STUDIES/ Results of survey on the health impairment due to pesticide application in farmers of 44 homes in a citrus cultivation district from May to July 1978 are reported. Pesticides causing severe skin impairment included quinomethionate.
Oxythioquinox's production may result in its release to the environment through various waste streams; its use as a fungicide and acaricide(1) will result in its direct release to the environment. However, oxythioquinox is not currently (March 2005) registered for use as a pesticide in the US(2).
AEROBIC: Field dissipation half-lives of 2.0-3.6 days have been reported for oxythioquinox in two sandy loam soils(1).
ANAEROBIC: A half-life of 3.7 days was reported for oxythioquinox in sandy loam soil under anaerobic conditions(1). The nitrogen-containing ring structure of oxythioquinox is apparently not cleaved by anaerobic ecosystems(2).
An estimated BCF of 160 was calculated for oxythioquinox(SRC), using a log Kow of 3.78(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment. Oxythioquinox is susceptible to both hydrolysis(1) and photolysis in water(4).
On February 1, 1999, Bayer requested voluntary cancellation of all the remaining Morestan products, contingent upon an 18-month existing stock provision which would allow them to deplete their remaining product inventory. EPA published a notice of receipt of Bayer's request for voluntary termination of oxythioquinox registrations in the Federal Register on March 17, 1999. The cancellation notice was published September 17, 1999. Per Bayer's request, the registrant will be allowed to sell and distribute existing stocks of these products for eighteen months after the effective date of cancellation, or until March 17, 2001. End-users will be allowed an additional year, until September 17, 2001 (for a total of 2 years beyond the registrant's requested date), for the use of existing stocks.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Oxythioquinox is found on List B. Case No: 2495; Pesticide type: Insecticide, fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 6-Methyl-2,3-quinoxalinedithiol cyclic S,S-dithiocarbonate; Data Call-in (DCI) Date(s): 02/21/91, 10/13/95; AI Status: The producer of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
When rats were fed carbonyl-14C-labelled oxythioquinox. It was found that most of the radioactivity was exhaled as 14CO2. After 2,3-14C- and 35S-labelled active ingredient was fed to rats, no 14CO2 was found in the air expired. In this particular case, most of the activity was present in the urine and in the feces. A small proportion of the activity was found in the blood plasma in protein-bound form. The activity is not present as oxythioquinox itself, but partially as 2,3-dithiol-6-methyl quinoxaline, in traces as the corresponding dihydroxy compound, and as other still unidentified metabolites. The quinoxaline ring is apparently not metabolized in the animal body.
The absorption and distribution of Morestan 35S in the organism of the rat were studied after administration by stomach tube. It was shown that Morestan, in vivo and in vitro, forms a complex with plasma proteins and particularly with albumins. Most of the plasma Morestan is distributed like this. After intravenous admininstration, the constant of elimination, K13, and the biological half-life determination show that plasma Morestan 35S is eliminated very slowly. The K12 and K21 constants indicate that there is an equilibrium between the plasma compartment and a peripheral compartment. After intragastric administration, the increase of radioactivity in epididymal adipose tissue, indicate that the peripheral compartment should include the adipose tissue.
Used as acaricide, fungicide, fumigant, and insecticide; Not currently registered with the EPA for use in the US; [HSDB] Banned for use in the EU; [eChemPortal: ESIS] An acaricide, insecticide, and fungicide used against powdery mildews and spider mites on fruits, cotton, ornamentals, greenhouse and other crops; [Ullmann]
Farming (Pesticides) [Category: Industry]
For oxythioquinox (USEPA/OPP Pesticide Code: 054101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Non-systemic fungicidal/acaricidal control of mites, mite eggs, pear psylla, and powdery mildew, e.g. red spider mite in gooseberry, strawberry, marrow, apple, and blackcurrant; powdery mildews in blackcurrant, marrow, and gooseberry; and leaf spot in blackcurrant.
Acaricide, fungicide, fumigant, insecticide
Selective non-systemic contact fungicide with protective and eradicant action. Also has some acaricidal activity. Control of powdery mildews and spider mites on fruit (including citrus), ornamentals, cucurbits, cotton, coffee, tea, tobacco, walnuts, vegetables, and glasshouse crops; American gooseberry mildew on gooseberries and currants.
By the condensation of dimercaptomethyl-quinoxaline with phosgene.
Chinomethionate is produced by the reaction of carbonyl chloride with 6-methyl-2,3-quinoxalinedithiol in aqueous alkaline solution.
Wettable powders, smoke generators, dusts.
'Morestan', WP (250 g a.i./kg); Morestan 2', DP (20 g/kg); FU.
Morestan as produced by Chemargo has a manufacturer's designation of purity of 92%.
Dustable powder, suspension concentrate, flowable wettable powder.
The technical compound contains at least 80% pure active ingredient and the following by-products in varying concentrations: Chlormorestan; Dithioether; Monothioether; Monochlordithioether; Methyldichlorquinoxaline; 6-Methyl-quinoxaline-3-thiol-2-cyclocarbonate; Iron, probably as 2,3-dimercapto-6-methyl-quinoxaline salt; Sulfur.
In late spring or summer applications some phytotoxicity may occur when morestan is used with most fungicides & insecticides. Morestan is Incompatible with oils (phytotoxic).
...Effective in controlling several mite species on wide range of crops. ... Controlled pear psylla, cotton bollworm & aphids. ... Excellent control of powdery mildew on apples, cucumbers, squash & muskmelons. Effective control of apple scab & downy mildew ... reported.
Registered for use on citrus and ornamentals.
일반 설명Yellow crystals. Non-corrosive. Used as a selective fungicide.
정의ChEBI: A dithioloquinoxaline that results from the formal condensation of 6-methylquinoxaline-2,3-dithiol with phosgene. It has been used as a fungicide and acaricide for the control of mites and powdery mildew on citrus, vegetables, and walnuts, but is not appro ed for use in the EU.