Endothall
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Endothall
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CAS No:
145-73-3
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Formula:
C8H10O5
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Chemical Name:
Endothall
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Synonyms:
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid;1,2-Cyclohexanedicarboxylic acid,3,6-endo-epoxy-;3,6-Endooxyphthalic acid,hexahydro-;Endothal;Endothall;1,2-Benzenedicarboxylic acid,hexahydro-3,6-endo-oxy-;Hydout;Herbon pennout;Aquothol;Hydrothol;Aquathol;NSC 112771;Endothallic acid;Endothalic acid;349466-39-3;857020-72-5
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CAS No:
Description
Endothall, when pure, is a white crystalline solid. The technical grade is a light brown liquidThe monohydrate is in the form of colorless crystals. Non corrosive. Used as a selective herbicide.
The monohydrate is in the form of colorless crystals. Non corrosive. Used as a selective herbicide.
The monohydrate is in the form of colorless crystals. Non corrosive. Used as a selective herbicide.
Endothall Basic Attributes
186.16
186.16
205-660-5
18F7018HG1
2811|3077
DTXSID7024081
Cyrstalline, white solid
2932190013
Characteristics
83.83000
1.91 (LogP)
The monohydrate is in the form of colorless crystals. Non corrosive. Used as a selective herbicide.
1.431 g/cm3
144 °C
447.8±40.0 °C(Predicted)
190.5ºC
1.568
soluble in water (>25 mg/ml), methanol, acetone, and DMSO. Insoluble in benzene.Stable up to 90°C, above which ENDOTHAL undergoes slow hydrolysis.
+2C to +8C
1.57e-10 mmHg
LD50 in adult male, female rats (mg/kg): 57, 46 orally (Gaines, Linder)
Odorless
pKa1 = 3.40; pKa2 = 6.7
When heated rapidly melts at about 144 C, decomposing into anhydride and water
Stable up to 90°C, above which it undergoes slow hydrolysis.
Acids, Carboxylic
A phthalic acid derivative.
Non-corrosive to metals
Safety Information
II
6.1(a)
UN 2811 6.1/PG 2
1
21-25-36/37/38
36/37/39-45
RN7875000
T
Stable to about 90 °C, at which temperature it undergoes slow conversion to anhydride; stable in acid and light.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P088, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.
Endothal is a dibasic acid, and forms water-soluble amine and alkali-metal salts.
California Environmental Protection Agency; Public Health Goal for Endotall in Drinking Water, December 1997[California Environmental Protection Agency; Public Health Goal for Endotall in Drinking Water, December 1997; Available from, as of March 13, 2014: http://oehha.ca.gov/water/phg/pdf/endo_c.pdf]|California State Dept Food and Agriculture. Pesticide Use Report Annual 1984|Finlayson BJ; Bull Environ Contam Toxicol 25 (4): 676-81 (1980). Toxicity of endothall is reviewed.|Folmar LC; Tech Pap US Fish Wildl Serv 88: 1-16 (1977). Toxicity of dalapon, dichlobenil and endothall to aquatic organisms is discussed.|For more Special Reports (Complete) data for ENDOTHALL (8 total), please visit the HSDB record page.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P330, P332+P313, P337+P313, P362, P405, and P501
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|When opening container, mixing or applying product, wear protective rubber or PVC gloves and rubber boots. Wear clean clothing daily. Wear a mask or pesticide respirator jointly approved by MESA/NIOSH.|Extinguishing method: Self-contained breathing apparatus, rubber gloves, hats, suits, and boots must be worn.|General handling procedure: Wear rubber gloves for all handling.|Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Nonflammable
Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
May be absorbed through skin, causing light to moderate irritation. ... Also irritating to nose, eye, and throat. Greatest occupational hazard is eye irritation caused by burning of tissues on exposure.|May be very irritating to skin, eyes, mucous membranes.
P088; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
P088; As stipulated in 40 CFR 261.33, when endothall, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
Toxicity
The combined preparation of endothall and isopropyl phenylcarbamate, Murbetol, is hundreds of times more herbicidal than either of the ingredients alone.|Cell adhesion and neurite outgrowth, mediated by the neural cell adhesion molecule L1, are inhibited in a dose-dependent manner by ethanol and other small alcohols. Ethanol inhibition of L1-mediated adhesion may contribute to the development of fetal alcohol syndrome. Although the pharmacology of ethanol inhibition of L1 adhesion is well characterized and antagonist molecules have been identified, the cellular mechanism underlying this phenomenon is unclear. The identification of ethanol-sensitive and insensitive cell lines derived from the same stable transfection of L1 suggests that additional cellular factors regulate the ethanol effect. Here we investigate the role of intracellular signaling molecules in ethanol inhibition of L1 adhesion. L1-mediated functions can be controlled by phosphorylation events and several kinases are known to phosphorylate L1, including casein kinase II (CK2), ERK 1/2 and p90rsk. Pharmacological inhibition of CK2 activity blocked ethanol inhibition of L1 adhesion in ethanol-sensitive NIH/3T3 cells stably expressing human L1 (2A2-L1) and in BMP-7 treated NG108 cells. However, ethanol had no direct effect on CK2 activity or subunit localization. We next asked what effect protein phosphatase inhibitors would have on ethanol sensitivity. Pretreating 2A2-L1 cells and BMP-7 treated NG108 cells with okadaic acid significantly reduced ethanol inhibition of L1 adhesion in a dose dependent manner (IC50 = 10 nM). Similar effects were seen with another phosphatase inhibitor, endothall. Neither of these drugs had any effect on L1 adhesion in. the absence of ethanol. The necessity of CK2 and phosphatase activity for ethanol sensitivity may be explained by the fact that phosphatase PP2A is activated by CK2. Thus, inhibiting CK2 could also reduce PP2A activity. The fact that ethanol has no direct effect on CK2 activity supports the idea that another protein (PP2A), besides CK2, may be a more direct regulator of ethanol sensitivity for L1 adhesion. Together, these results show that ethanol' inhibition of L1 adhesion can be controlled by intracellular signaling pathways and suggest new avenues for the development of ethanol antagonists.|The beneficial effect of phosphodiesterase 5A inhibition in ischemia/reperfusion injury and cardiac hypertrophy is well established. Inhibition of the cardiac Na(+)/H(+) exchanger (NHE-1) exerts beneficial effects on these same conditions, and a possible link between these therapeutic strategies was suggested. Experiments were performed in isolated cat cardiomyocytes to gain insight into the intracellular pathway involved in the reduction of NHE-1 activity by phosphodiesterase 5A inhibition. NHE-1 activity was assessed by the rate of intracellular pH recovery from a sustained acidic load in the absence of bicarbonate. Phosphodiesterase 5A inhibition with sildenafil (1 umol/L) did not affect basal intracellular pH; yet, it did decrease proton efflux (J(H); in millimoles per liter per minute) after the acidic load (proton efflux: 6.97 +/- 0.43 in control versus 3.31+/- 0.58 with sildenafil; P<0.05). The blockade of both protein phosphatase 1 and 2A with 100 nmol/L of okadaic acid reverted the sildenafil effect (proton efflux: 6.77+/- 0.82). In contrast, selective inhibition of protein phosphatase 2A (1 nmol/L of okadaic acid or 100 umol/L of endothall) did not (3.86 +/- 1.0 and 2.61+/- 1.2), suggesting that only protein phosphatase 1 was involved in sildenafil-induced NHE-1 inhibition. Moreover, sildenafil prevented the acidosis-induced increase in NHE-1 phosphorylation without affecting activation of the extracellular signal-regulated kinase 1/2-p90(RSK) pathway. Our results suggest that phosphodiesterase 5A inhibition decreases NHE-1 activity, during intracellular pH recovery after an acidic load, by a protein phosphatase 1-dependent reduction in NHE-1 phosphorylation.
A male died after swallowing two mouthfuls of 175 g/L disodium endothall. This represents a dose of approximately 100 mg/kg.
LD50 Rat oral 38-51 mg/kg for acid (technical)|LD50 Rat oral 182-197 mg/kg /Sodium salt (19.2% solution)/|LD50 Rat oral 206 mg/kg /Amine salt (66.7% formulation)/|LD50 Rat (male) oral 57 mg/kg|For more Non-Human Toxicity Values (Complete) data for ENDOTHALL (6 total), please visit the HSDB record page.
/AQUATIC SPECIES/ Acute and behavioral toxicity to goldfish Carassius auratus was determined for the aquatic herbicides diquat and endothall, separately and combined as a 1:1 mixture by volume. Goldfish did not avoid the mixture at 0.11 mg/L diquat: 0.17 mg/L endothall, but did avoid 10 times and 100 times these concn. When exposed to the chemicals individually, goldfish did not avoid endothall at 0.17 or 1.70 mg/L, but avoided it at 17.0 mg/L. The 96 hr median tolerance limit was 372 mg/L for endothall.|/AQUATIC SPECIES/ The 14 day median lethal concentration of endothall to chinook salmon was 62.5 ppm. The seawater entry test was the more sensitive indicator of toxicity, as the fish that had been exposed to levels as low as 3 ppm for 4 days died when placed in seawater. Some behavioral and gross anatomical changes were observed, and histopathological examination revealed hypertrophy of branchial epithelial cells in the fish exposed to greater than 10 ppm endothall.|/AQUATIC SPECIES/Thirty healthy smolts /coho salmon Oncorhynchus kisutch/ were first exposed to 5.0 mg endothall in freshwater for 96 hr, then challenged with seawater for 24 hr. Blood plasma sodium was measured as an indicator of the smolts' ability to osmoregulate. Mean plasma sodium concentrations did not differ substantially between exposed (170.7 meq/L) and control (170.9 meq/L) groups.|/AQUATIC SPECIES/ When potassium endothall was applied to the 1093 acre Chickahominy Reservoir in Virginia to control Egeria densa Planchon, concentrations of 0.17 mg/L endothall did not alter bluegill respiration rate. Concentrations as high as 17.0 mg/L endothall tested over 96 hours in bioassays did not cause histopathological changes in hematocrit, total plasma proteins, plasma protein electropherograms, or white blood cell differentials. Goldfish exposed had no alterations in plasma glucose, glucocorticoids, androgens, estrogens, hematocrit, or white blood cell differential. /Potassium endothall/|For more Ecotoxicity Excerpts (Complete) data for ENDOTHALL (11 total), please visit the HSDB record page.
Endothall's production may result in its release to the environment through various waste streams; it's use as an herbicide and defoliant(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 13(2), determined from a log Kow of 1.91(3) and a regression-derived equation(2), indicates that endothall is expected to have very high mobility in soil(SRC). The pKa values for the carboxylic acid moieties of endothall are 3.4 and 6.7(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5) nor do they volatilize from moist soil surfaces. Endothall is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.57X10-10 mm Hg(4). The half-life of endothall is reported to be 4 to 5 days in clay soils and 9 days in soils with high organic content(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 13(2), determined from a log Kow of 1.91(3) and a regression-derived equation(2), indicates that endothall is not expected to adsorb to suspended solids and sediment(SRC). The pKa values for the carboxylic acid moieties of endothall are 3.4 and 6.7(4), indicating that endothall will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), a BCF of <1 in bluegill sunfish (Lepomis macrochirus)(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). If released to water, endothall will biodegrade under aerobic conditions with a half-life of approximately 1 week or less(7), suggesting that biodegradation may be an important environmental fate process in water(SRC).|AQUATIC FATE: Endothall applied to a pond at various concentrations ranging from 0.3 to 10 ppm was undetectable after an average of 2.5 days and a maximum of 4 days(1) and in another study, 55% of the 1.2 ppm endothall added to pond water was removed after 12 days(2). In experimental greenhouse pools treated with 0.03, 1.6 or 4.5 ppm endothall, an overall half-life of 4 days was reported(3). In farm reservoirs, approx 71% removal of 0.3 to 1.4 ppm endothall was observed in 12 days(1). Endothall added to the water of irrigation supply ponds at 2 ppm decreased linearly with the predicted concentration of zero at 26 days (half-life 12 days)(4). Only 28% removal of endothall was observed 30 days after addition of endothall to anoxic water(1).|AQUATIC FATE: A mixture of diquat dibromide and potassium endothall was applied at 2.83 liters of each chemical per 0.4 surface acre to the 1093 acre Chickahominy Reservoir, Virginia because of nuisance populations of Egeria densa Planchon (egeria)(1). Both herbicides declined to very low levels in the water 3 days after treatment and were undetectable within 16 days after treatment(1). No endothall was found in bottom sediments nor in fish muscle tissue(1).|For more Environmental Fate (Complete) data for ENDOTHALL (7 total), please visit the HSDB record page.
Endothall does not undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1,2). Endothall has been reported to be stable in the presence of sunlight(2).|(14)Carbon endothall, labled at positions 1 and 2 of ring, was added to pond water and to hydrosoil. Within 10 days, 25% of label was evolved as (14)CO2.
A BCF of <1 of endothall has been measured using bluegill sunfish (Lepomis macrochirus)(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
123.03 L/kg|The Koc of endothall is estimated as 13(1), using a log Kow of 1.91(2) and a regression-derived equation(1). According to a classification scheme(3), these Koc values suggest that endothall is expected to have very high mobility in soil. The pKa values for the two carboxylic acid moieties of endothall are 3.4 and 6.7(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). The Koc of endothall in sediment/water systems has been measured to be < 2(2) and 10(6).
The pKa values for the carboxylic acid moieties of endothall are 3.4 and 6.7(1), indicating that this compound will primarily exist in anion form in the environment and anions do not volatilize from water or moist soil surfaces. Endothall is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.57X10-10 mm Hg(1).
Occupational exposure to endothall may occur through dermal contact with this compound at workplaces where endothall is produced or used. Use data indicate that the general population may be exposed to endothall via dermal contact with this compound and other consumer products containing endothall. Additional exposure may occur through dermal contact and ingestion of contaminated water where this compound was used as an algaecide. (SRC)
Drug Information
A male died after swallowing two mouthfuls of 175 g/L disodium endothall. This represents a dose of approximately 100 mg/kg.
May be absorbed through skin ...|Over 90% of radioactivity from (14)carbon labeled endothall administration orally to rats recovered in feces. Remainder recovered from urine and as expired air. Virtually complete recovery of administered dose within 48 hr.|When bluegills were exposed in aquaria to water containing 2 ppm of (14)Carbon endothall, less than 1% of the herbicide was absorbed by the fish. The concentration of (14)Carbon residues were highest in the viscera and lowest in the flesh. Endothall is also absorbed by the fish when fed through the digestive tract.|...labeled endothall /was administered/ to two lactating rats to determine whether endothall was secreted in milk The animals received a daily oral dose of 0.2 mg endothall (in 10% sucrose solution) for five consecutive days prior to delivery. After birth, dams received a daily dose of 0.4 mg endothall in 10% sucrose solution for five consecutive days. After sacrifice of the pups, no radioactivity was detected in any of the tissues or stomach contents suggesting that endothall was not secreted into the milk of lactating rats.|For more Absorption, Distribution and Excretion (Complete) data for ENDOTHALL (6 total), please visit the HSDB record page.
The fate of the widely used herbicide, endothall, in various organisms and systems is reviewed. Limited results indicate that endothall absorbed by plants and fish is completely metabolized, but in mammals it is excreted largely as the bound form.
Cyclic AMP-dependent protein kinase (PKA) and Ca(2+)-calmodulin dependent protein kinase II (CaMKII)-mediated phosphorylation activate histamine synthesis in nerve endings, but the phosphatases deactivating it had not been studied. In this work we show that the protein phosphatase 2A (PP2A)/protein phosphatase 1 (PP1) inhibitor okadaic acid increases histamine synthesis up to twofold in rat cortical miniprisms containing histaminergic nerve endings. This effect was mimicked by the PP2A/PP1 inhibitor calyculin, but not by the inactive analog 1-norokadaone. Other phosphatase inhibitors like endothall (PP2A), cypermethrin and cyclosporin A (protein phosphatase 2B, PP2B) had much lower effects. The effects of okadaic acid appeared to be mediated by an activation of the histamine synthesizing enzyme, histidine decarboxylase. PKA-mediated activation of histamine synthesis decreased the EC(50) and maximal effects of okadaic acid. On the other hand, CaMKII-mediated activation of histamine synthesis decreased okadaic acid maximal effects, but it increased its EC(50). In conclusion, our results indicate that brain histamine synthesis is subjected to regulation by phosphatases PP2A and PP1, and perhaps also PP2B as well as by protein kinases.|... Protein phosphatase (PP) inhibitors and rat cerebellar glial cells in primary culture /were used/ to investigate the role of PP activity in the ability of glial cells to detoxify exogenously applied hydrogen peroxide (H2O2). The marine toxin okadaic acid (OKA), a potent PP1 and PP2A inhibitor, caused a concentration-dependent degeneration of astrocytes and increased the formation of hydroperoxide radicals significantly. Subtoxic exposures to OKA significantly potentiated toxicity by exogenous H2O2. The concentration of H2O2 that reduced by 50% the survival of astrocytes after 3 hr was estimated at 720+/-40 uM in the absence and 85+/-30 uM in the presence of the toxin. The PP inhibitors calyculin A and endothall also potentiated H2O2 toxicity in cerebellar astrocytes. OKA caused a time-dependent inhibition of both glial catalase and glutathione peroxidase, reducing by approximately 50% the activity of these enzymes after 3 hr, whereas other enzymatic activities remained unaffected. Also, OKA reduced the cellular content of total glutathione and elevated oxidized glutathione to about 25% of total glutathione. OKA-treated astrocytes cleared H2O2 from the incubation medium approximately two times more slowly than control cultures. Our results suggest a prominent role for PP activity in the antioxidant mechanisms protecting astrocytes against damage by H2O2.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Wash endothall from the skin with soap and water. Flush contamination from the eyes with copious amounts of clean water. Obtain medical attention if irritation of skin or eyes persists.|If a large quantity has been ingested, the patient is seen within an hour of exposure, and is fully alert and not convulsing, gastrointestinal decontamination should be considered... . Lavage is usually contraindicated due to the corrosive nature of this agent.|If there are indications of corrosive effects in the pharynx, gastric intubation should not be attempted because of the risk of esophageal perforation. Treatment procedures appropriate for ingestions of corrosives (strong acids and alkalis) may be necessary. Referral should be made to a surgeon or gastroenterologist for consideration of endoscopy.|Oxygen should be given by mask, if respiratory drive is weak, pulmonary ventilation may have to be supported mechanically.|For more Antidote and Emergency Treatment (Complete) data for ENDOTHALL (11 total), please visit the HSDB record page.
/SIGNS AND SYMPTOMS/ Ingestion may cause severe GI inflammation with erosion.|/SIGNS AND SYMPTOMS/ May be absorbed through skin, causing light to moderate irritation. More severe effects at concentrations over 1%, with immediate burning sensation on abraded skin. Also irritating to nose, eye, and throat. Greatest occupational hazard is eye irritation caused by burning of tissues on exposure.|/CASE REPORTS/ A fatal case of suicidal ingestion of the herbicide endothall is described in a male after apparently ingesting about two mouthfuls ... 175 g/L of disodium endothall. Autopsy revealed widespread focal hemorrhages and edema in lungs, and gastrointestinal tract showed gross hemorrhage. Concn of endothall in stomach contents, liver and blood were 4.0, 1.7, and 1.0 mg%, respectively. /Disodium endothall/|/CASE REPORTS/ A 23-year-old man ingested 40 mL /endothall/ and developed vomiting with abdominal pain. gastric decontamination with charcoal and chocolate milk was performed. Symptoms stabilized, but 6 hours later, hematemesis occurred and was followed by acidosis, anuria, disseminated intravascular coagulation, and hypotension and cardiovascular collapse. The patient died 12 hours post-ingestion.|For more Human Toxicity Excerpts (Complete) data for ENDOTHALL (6 total), please visit the HSDB record page.
endothall
Endothall Use and Manufacturing
Endothall is made by the condensation of furan and maleic anhydride ... The reaction is conducted at 35 °C and atmospheric pressure in the liquid phase. Isopropyl ether may be used as a reaction diluent. No catalyst is used and the reaction time is about 7 hours.|Endothal is made by reduction of the Diels-Alder condensation product of furan and maleic anhydride.|Furan undergoes the Diels-Alder reaction with strong dienophiles. Hydrogenation of the product resulting from reaction with maleic anhydride, followed by hydrolysis and neutralization gives a herbicide, endothall.|Olin, Unites States of America Patent 2550494 (1951 to Sharples Chemicals.)
Defoliant, herbicide. Preemergence and postemergence herbicide for control of broad-leaved weeds and annual grass in vegetable crops. The disodium and dipotassium salts are used as defoliants and herbicides.Herbicide, Algaecide: Endothall is used as a cotton defoliant and as a selective contact herbicide on both terrestrial and aquatic weeds. The potassium and amine salts of endothall are used as aquatic herbicides to control a variety of plants including plankton, pondweed, niad, coontai
(1984) In California in 1984, 3.96X10+7 g of the mono(N,N-diethylalkylamine) salt were used; 1.83X10+6 g of the dimethylamine salt were used; minor amounts (less than 1X10+3 g) of the dimethylalkylamine and dipotassium salts were used.|(1991) Exceeded 5000 lb or USA $5000 in value
Cotton production, 95.6%; Sugarbeets, 3.9%; Remainder in landscape maintenance or "public health pest control" (1984) /California use, calculated from table/|In terms of pounds used, endothall is most readily used as an aquatic herbicide. For terrestrial endothall uses, the majority of use is on potatoes (approximately 5% crop treated) and cotton (less than 2.5% crop treated). Of the two forms of endothall, the N, N-dimethylalkylamine salt accounts for the most use.
Endothan weed killer, Aquathol, Endothal turf herbicide (disodium endothall-15.5% acid equiv); Herbicide 273, Potassium Endothal (dipotassium endothall 28.6% acid equiv); Herbicide 282, Herbicide 283 (di- and mono-(N,N-dimethylalkylamine) salts ... 18.8% and 23.36% acid equiv); Endothal harvest acid (disodium endothall plus ammonium sulfate 5.1% acid equiv); Des-I-cate, Accelerate (mono-(N,N-dimethylaklamine) salt ... plus ammonium sulfate 0.52% acid equiv); Aquathol plus (dipotassium salt ... and potassium salt of silvex 15.7% + 22.2% acids equiv); Endothal-TCA (disodium salt ... +TCA 5.76%= 11.9% acids equiv). Murbetol (endothal-sodium salt 14.24% active plus propham 8.55% active).|Aquathol; 1.46 lb/gal liquid concentrate of endothall disodium salt|Aquathol Granular; 7.2% endothall dipotassium salt|Aquathol K; 3 lb/gal endothall dipotassium salt|For more Formulations/Preparations (Complete) data for ENDOTHALL (12 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies endothal-sodium (technical grade) as Class II: moderately hazardous; Main Use: herbicide. /Endothal-sodium/|Introduced by the Sharples Chemical Corporation. (now merged with Pennwalt Corp.)|The compound is selectively toxic to plants.|... In production of hops /endothall is promising for control of downy mildew by its use on basal leaves and suckers of the plants/.|For more General Manufacturing Information (Complete) data for ENDOTHALL (8 total), please visit the HSDB record page.
Method: EPA-NERL 548.1; Procedure: gas chromatograpy with flame ionization detection; Analyte: endothall Matrix: drinking water sources and finished drinking water; Detection Limit: 0.7 ug/L.|Method: EPA-NERL 548.1; Procedure: gas chromatograpy with mass spectrometry detection; Analyte: endothall Matrix: drinking water sources and finished drinking water; Detection Limit: 1.79 ug/L.|Product analysis is by GLC with a flame ionization detector. Residues may be determined by GLC of a derivative, which is measured by microcoulometric detection.
HERBICIDES
Computed Properties
Molecular Weight:186.16
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:186.05282342
Monoisotopic Mass:186.05282342
Topological Polar Surface Area:83.8
Heavy Atom Count:13
Complexity:235
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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