5259-88-1CC1=C(C(=O)Nc2ccccc2)S(=O)(=O)CCO1AMEKQAFGQBKLKX-UHFFFAOYSA-NOxycarboxin is an anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-4,4-dioxo-1,4-oxathiine-3-carboxylic acid. A fungicide for the control of rust diseases on ornamentals, cereals and nursery trees as well as fairy rings on turf. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is an anilide, a sulfone, an oxacycle, an organosulfur heterocyclic compound and an anilide fungicide.
Fungicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Fungicides
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Pesticide (Oxycarboxin) -> USDA PDB
log Kow = 0.772
1.13
OFF-WHITE CRYSTALS
White solid
In water, 1,400 mg/L at 25 °C
83.7 g/L in acetone, 8.8 g/L in hexane
38 [ug/mL] (The mean of the results at pH 7.4)
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)
Commission Regulation (EC) No 33/2008
2002/2076
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Carboxin (and Oxycarboxin). EPA 738-R-04-015 September 2004. Available from the Database Query page at http://cfpub.epa.gov/oppref/rereg /status.cfm?show=rereg as of April 22, 2005. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Oxycarboxin (5259-88-1) as of April 20, 2005.
The Reregistration Eligibility Decision (RED) document for the active ingredient carboxin (PC code 090201) was completed in September 2004 as part of Reregistration Case 0012. Reregistration Case 0012 also includes another active ingredient, oxycarboxin (PC code 090202), that was inadvertently omitted. The Environmental Protection Agency (EPA or Agency) has since reviewed the occupational exposure to oxycarboxin fungicide from use on ornamentals grown in enclosed commercial structures such as greenhouses, which is the only registered use. The Agency has determined that oxycarboxin containing products are eligible for reregistration provided that the required confirmatory data are submitted.
Oxycarboxin inhibited the growth of rhizobia in vitro at concentration of 19 ug/mL. Growth inhibition appeared to be primarily due to inhibition of respiration. The effect of oxycarboxin was more pronounced on RNA. Inhibition was transitory and the bacterium overcame this initial inhibition without mutation.
/Oxycarboxin inhibits/ oxidative metabolism and succinic dehydrogenase in mitochondria of liver and bone.
Oxycarboxin inhibits oxidative metabolism and specifically succinate dehydrogenase activity in both fungal and vertebrate mitochondria, but the potency was much higher against the enzyme from the target species (Rhizoctonia solani, I50 = 6.8 uM; Ustilago maydis, I50 = 8.0 uM) than vertebrates (rat and mouse liver , I50 = 50-100 uM). It is less potent than carboxin as an inhibitor of complex II in both fungi and vertebrates.
The most prominent metabolites /of oxycarboxin/ result from the opening of the oxathiin ring.
When bean plants were exposed to oxycarboxin, four degradation products found in the plants and solution in which the plants were incubated were identified as: 2-(2-hydroxyethylsulfonyl)acetanilide, 4-phenyl-3-thiomorpholinone-1,1-dioxide, 2-(vinylsulfonyl)acetanilide.
In plants carboxin and its metabolite, carboxin sulfoxide, are absorbed by germinating seeds /and/ moved upward in the plant, traveling with the transpiration system and moving into the lower stem and first leaves of the plant. Carboxin does not redistribute into new growth as the plant matures, and is not found in seeds or upper leaves of crops grown from treated seeds. Oxycarboxin is more stable in plants than carboxin but it is distributed in a similar manner.
/Oxycarboxin is/ ... excreted in urine and feces.
現在のフィルター条件では反応記録がありません。
読み込み中…
5259-88-1DTXSID8034792CHEMBL1712057CHEBI:78580.00000004 [mmHg]
4.2X10-8 mm Hg
化学的特性Oxydisulfoton is a white corrosive solid.
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. Oxycarboxin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0012; Pesticide type: Fungicide; Registration Standard Date: 08/08/81; 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): Oxycarboxin; Data Call-in (DCI) Date(s): 02/17/94, 10/13/95; AI Status: The producers 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%)
Acute toxicity - category 4
Acute Tox. 4 *
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.
Do not inhale dust or spray mist; avoid contact with skin and mucous membranes
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
LC50 /Colinus virginianus/ (Northern bobwhite quail) dietary >10000 mg/kg/8 days
LC50 Mallard ducks oral >4640 mg/kg in 8-day diet
LC50 Bluegill 28.1 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LC50 Rainbow trout 19.9 mg/L/96 hr /Conditions of bioassay not specified in source examined/
For more Ecotoxicity Values (Complete) data for OXYCARBOXIN (14 total), please visit the HSDB record page.
TERRESTRIAL FATE: FIVE DIFFERENT SOILS WERE TESTED FOR PERSISTENCE & DEGRADATION OF CARBOXIN & OXYCARBOXIN. IN ONE SOIL ONLY, BOTH WERE DEGRADED WITH ACCUMULATION OF AMMONIUM & NITRITE. UNDER CONDITIONS OF FORCED CIRCULATION OF AIR & CONTINUOUS PERFUSION, OXYCARBOXIN WAS MORE SUSCEPTIBLE TO DEGRADATION THAN CARBOXIN. UNDER SIMULATED RICE FIELD CONDITIONS, CONVERSION OF CARBOXIN TO ITS SULFOXIDE & TO NONTOXIC DERIVATIVE OF OXYCARBOXIN WAS OBSERVED IN ALL SOILS. IN ORGANIC MATTER FREE SOIL DEGRADATION WAS DELAYED. ON THREE FORMS OF MONOIONIC CLAYS, CARBOXIN WAS RAPIDLY CONVERTED TO ITS SULFOXIDE BUT OXYCARBOXIN WAS TRANFORMED TO AN UNIDENTIFIED DERIVATIVE.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that oxycarboxin is expected to have very high mobility in soil(SRC). Volatilization of oxycarboxin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 4.2X10-8 mm Hg(3), and water solubility, 1400 mg/L(3). Oxycarboxin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The half-life of oxycarboxin has been reported to range from about 2.5 to 8 weeks in soils(3).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that oxycarboxin is not 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 1.1X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 4.2X10-8 mm Hg(4), and water solubility, 1400 mg/L(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from a log Kow of 0.77(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis half-life of oxycarboxin was reported as 44 days at pH 6 and 25 °C(4). Oxycarboxin may be subject to indirect photolysis in sunlit surface waters containing humic and fulvic acids which act as photosensitizing agents(7). Oxycarboxin solutions containing 1 ppm humic or fulvic acids were photodegraded approximately 25% following 8 hours of irradiation with simulated sunlight and approximately 20% photodegradation was observed for oxycarboxin solutions containing soil suspensions(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oxycarboxin, which has a vapor pressure of 4.2X10-8 mm Hg at 25 °C(2), is expected to exist primarily in the particulate phase in the ambient atmosphere. Particulate-phase oxycarboxin may be removed from the air by wet and dry deposition(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for oxycarboxin can be estimated to be 20(SRC). According to a classification scheme(2), this estimated Koc value suggests that oxycarboxin is expected to have very high mobility in soil.
Oxycarboxin's production may result in its release to the environment through various waste streams(SRC). Oxycarboxin is only registered for use as a fungicide for ornamentals grown in enclosed commercial structures such as greenhouses and its direct release to the environment from this use is unlikely(1). Oxycarboxin has been identified as a degradation product of a related fungicide, carboxin(1); therefore, the use and subsequent degradation of carboxin may result in the indirect release of oxycarboxin in the environment(SRC).
MICROORGANISMS FOUND IN WET SOILS WERE EXAMINED FOR THEIR ABILITY TO DEGRADE FUNGICIDES. THE BLUE-GREEN ALGAE ANABAENA, NOSTOC, & TOLYPOTHRIX EXTENSIVELY DEGRADED OXYCARBOXIN & CARBOXIN. THE PHOTOSYNTHETIC BACTERIUM RHODOSPIRILLUM DEGRADED OXYCARBOXIN TO A GREATER EXTENT THAN CARBOXIN. THE PROTOZOA, COLPODA BROUGHT ABOUT AN EXTENSIVE DEGRADATION OF CARBOXIN BUT NOT OF OXYCARBOXIN.
AN ISOLATE OF SOIL PSEUDOMONAS HYDROLYZED OXYCARBOXIN TO ANILINE & WAS CAPABLE OF UTILIZING OXYCARBOXIN AS ITS SOLE SOURCE OF C & N.
When incubated with a Norcardia sp species isolated from soil, oxycarboxin was found to undergo amide hydrolysis(1). Blue-green algae (Anabaena, Nostoc, Tolypothrix, and Chlorella vulgaris) isolated from wet soil were found to degrade oxycarboxin(2). Oxycarboxin was found to degrade in five different soil types including 3 monoionic clays (red sandy loam, black clayey, laterite, saline alkalai, and coffee plantation), were found to degrade oxycarboxin in 10 days under aerobic conditions(3).
The half-life of oxycarboxin in a sandy loam was reported to range from 2.5 to 8 weeks(1).
An estimated BCF of 3 was calculated for oxycarboxin(SRC), using a log Kow of 0.77(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 Henry's Law constant for oxycarboxin is estimated as 1.1X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 4.2X10-8 mm Hg(1), and water solubility, 1400 mg/L(1). This Henry's Law constant indicates that oxycarboxin is expected to be essentially nonvolatile from water surfaces(2). Oxycarboxin is not expected to volatilize from dry soil surfaces(SRC) based upon vapor pressure(1).
/LABORATORY ANIMALS: Acute Exposure/ Mild eye irritant; not a skin irritant (rabbits).
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Feeding to albino rats or dogs at 300, 1000, and 3000 mg/kg diet daily for 2 yr induces no toxic effects.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In 2-year dietary studies a NOEL for rats was observed at 15mg/kg/day based on minor thyroid changes.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ F-461 /(oxycarboxin)/ Technical was given to CD derived rats in the feed for 2 years at 0, 300, 1000 or 3000 ppm, 30/sex/experimental group, 60/sex/control. Possible adverse effects noted. NOEL approx. 300 ppm, based on thyroid findings. Thyroids had increased weight in all groups at 6 months (but no dose relationship at 6 months and no thyroid weight differences at subsequent sacrifices). Hyperplastic alterations were observed in males at 3000 ppm at 6, 12 and 24 months. In addition, there was an apparent treatment-related incidence of "clumped basophilic-staining colloid in the follicles" in 1000 ppm males.
For more Non-Human Toxicity Excerpts (Complete) data for OXYCARBOXIN (9 total), please visit the HSDB record page.
The hydrolysis half-life of oxycarboxin was reported as 44 days at pH 6 and 25 °C(1). Less than 10% photodegradation was observed when oxycarboxin solutions were exposed to light > 290 nm for 8 hours; however, this reaction was shown to be enhanced with the addition of humic and fulvic acids which act as photosensitizing agents(2). Oxycarboxin solutions containing 1 ppm humic or fulvic acids were photodegraded approximately 25% following 8 hours of irradiation with simulated sunlight and approximately 20% photodegradation was observed for oxycarboxin solutions containing soil suspensions(2).
Occupational exposure to oxycarboxin may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Since oxycarboxin is only registered for use on ornamentals in enclosed structures such as greenhouses and can only be applied by commercial applicators utilizing hand held equipment(1), exposure to the general population is expected to be low(SRC).
Oxycarboxin's production may result in its release to the environment through various waste streams. Oxycarboxin is only registered for use as a fungicide for ornamentals grown in enclosed commercial structures such as greenhouses and its direct release to the environment from this use is unlikely. Oxycarboxin has been identified as a degradation product of a related fungicide, carboxin; therefore, the use and subsequent degradation of carboxin may result in the indirect release of oxycarboxin in the environment. If released to air, a vapor pressure of 4.2X10-8 mm Hg at 25 °C indicates oxycarboxin will exist primarily in the particulate phase in the ambient atmosphere. Particulate-phase oxycarboxin will be removed from the atmosphere by wet and dry deposition. If released to soil, oxycarboxin is expected to have very high mobility based upon an estimated Koc of 20. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.1X10-11 atm-cu m/mole. Oxycarboxin is not expected to volatilize from dry soil surfaces based upon its vapor pressure. The half-life of oxycarboxin has been reported to range from about 2.5 to 8 weeks in soils. If released into water, oxycarboxin is not expected to adsorb to suspended solids and sediment based upon the estimated Koc value. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. Hydrolysis occurs slowly in aqueous environments based upon a hydrolysis half-life of 44 days at pH 6. Indirect photolysis in sunlit surface waters may be an important environmental fate process for oxycarboxin. Oxycarboxin solutions in which 1 ppm humic or fulvic acids were added were photodegraded roughly 25% when irradiated with simulated sunlight over an 8 hour photoperiod. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to oxycarboxin may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Since oxycarboxin is only registered for use on ornamentals in enclosed structures such as greenhouses and can only be applied by commercial applicators utilizing hand held equipment, exposure to the general population is expected to be low. (SRC)
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/
The Reregistration Eligibility Decision (RED) document for the active ingredient carboxin (PC code 090201) was completed in September 2004 as part of Reregistration Case 0012. Reregistration Case 0012 also includes another active ingredient, oxycarboxin (PC code 090202), that was inadvertently omitted. The Environmental Protection Agency (EPA or Agency) has since reviewed the occupational exposure to oxycarboxin fungicide from use on ornamentals grown in enclosed commercial structures such as greenhouses, which is the only registered use. The Agency has determined that oxycarboxin containing products are eligible for reregistration provided that the required confirmatory data are submitted.
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. Oxycarboxin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0012; Pesticide type: Fungicide; Registration Standard Date: 08/08/81; 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): Oxycarboxin; Data Call-in (DCI) Date(s): 02/17/94, 10/13/95; AI Status: The producers 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.
Used as systemic fungicide on ornamentals, cereals, and nursery trees; [HSDB] Used as a fungicide on ornamentals grown in a greenhouse; [EPA REDs]
Farming (Pesticides) [Category: Industry]
For oxycarboxin (USEPA/OPP Pesticide Code: 090202) ACTIVE products with label matches. /SRP: Registered for 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./
Systemic fungicide; Foliar application for rust on carnations and geraniums (greenhouse only).
Plantvax was effective in controlling Udbatta disease of rice caused by Ephelis oryzae.
Oxycarboxin was excellent against stripe rust (Puccinia striiformis), good against stripe smut (Ustilago striiformis), & completely eradicated flag smut (Urocystis agropyri) after soil application.
Oxycarboxin is produced by oxidation of oxathiin, which is prepared by reaction of acetoacetanilide with sulfonyl chloride, followed by treatment with a potassium hydroxide solution and then with 2-mercaptoethanol.
BY OXIDATION OF VITAVAX WITH HYDROGEN PEROXIDE.
Emulsifiable concentrate, wettable powder
Technical grade is >/=97% pure.
Products: Plantvax; Carboject. Discontinued products: Ringmaster.
In the U.S., there are two products containing oxycarboxin: A technical product and an end-use product. Both products are supported by Crompton Corporation. The single oxycarboxin end-use product (Plantvax 75W, EPA Registration Number 400-144) is a wettable powder fungicide to be used as a foliar spray for control of rust diseases of ornamentals grown in enclosed commercial structures such as greenhouses, shadehouses and interiorscapes. It can only be applied by commercial applicators utilizing hand held equipment.
INTRODUCED IN 1966 BY UNIROYAL AS AN EXPERIMENTAL SYSTEMIC SEED TREATMENT FUNGICIDE. FIRST DESCRIBED BY B VON SCHMELING & M KULKA, SCI 152: 659 (1966); ... US PATENTS 3,399,214 & 3,402,241. ... INCOMPATIBILITIES: COMPATIBLE WITH ALL BUT HIGHLY ACIDIC OR BASIC PESTICIDES. EFFECTIVE SYSTEMIC FUNGICIDE THAT CONTROLS BY SEED, SOIL, OR FOLIAR TREATMENT THE RUSTS OF SMALL GRAINS, VEGETABLES & ORNAMENTALS. SUGGESTED RATES 1.5 TO 4.0 LB PER ACRE FOR FOLIAR AND SOIL TREATMENTS.
用途ミトコンドリア複合体Ⅱ阻害剤花卉・ムギ類のさび病
定義ChEBI: An anilide obtained by formal condensation of the amino group of aniline with the carboxy group of 2-methyl-5,6-dihydro-4,4-dioxo-1,4-oxathiine-3-carboxylic acid. A fungicide for the control of rust diseases on ornamentals, cereals and nursery trees as wel as fairy rings on turf.