Ioxynil

370.91

370.91

2364041

216-881-1

8Y734M4V9E

0900

2588

DTXSID8022161

Colorless crystalline solid

29269095

44.02000

3.60

beige amorphous powder

2.4947 (estimate)

212-213 °C

282.6±40.0 °C(Predicted)

124.7±27.3 °C

1.805

Insoluble

0-6°C

0.00194mmHg at 25°C

Oral-Rat LD50: 110 mg/kg; Oral-Mouse LD50: 230 mg/kg

Combustion produces toxic nitrogen oxides and iodide gas

Faint phenolic /tech grade/|Odorless when pure

PK: 3.96

133.06 Ų [M-H]-

HYDROLYZED TO THE BENZAMIDE WHEN WARMED WITH CONCN SULFURIC ACID; PROLONGED TREATMENT WITH CONCN SULFURIC ACID @ 40 °C RESULTS IN FORMATION OF THE CORRESPONDING BENZOIC ACID; RAPIDLY DECOMPOSES TO PRODUCE FREE IODINE & IODIDE IONS WHEN HEATED ABOVE 60 °C IN UV LIGHT OR SUNLIGHT|SUBLIMES AT ABOUT 140 °C @ 0.13 mbar|Solubilities: In water 107 g/l (20-25 °C). In acetone 60, 20% aqueous acetone 560, tetrahydrofurfuryl alcohol 750, methyl cellosolve 770 (all in g/l, 20-25 °C /Potassium salt/|Very stable to acids and alkalis. Acidic in reaction, and forms salts.|Decomposed by sunlight and UV light.

Dust explosion possible if in powder or granular form, mixed with air.

Non-corrosive

III

6.1

3276

3

63-50/53-48/22-36-23/25-21

61-60-45-36/37-63

DI4025000

N-T,N,T

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

PRACTICALLY NON-VOLATILE|NO DETERIORATION IN LESS THAN 2 YEARS OF STORAGE|Very stable to acids and bases. Decomposed by sunlight and UV light.

P201-P261-P273-P280-P301 + P310 + P330-P304 + P340 + P312

H301 + H331-H312-H319-H361d-H373-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P314, P321, P322, P330, P337+P313, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P309+P311, P311, P312, P314, P321, P322, P330, P337+P313, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 202 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, foam, carbon dioxide.

Wear protective gloves when handling concentrate.

Avoid skin and eye contact and inhalation of spray fumes. Prevent drifting.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is mildly irritating to the eyes and skin.

Animal tests show that this substance possibly causes toxicity to human reproduction or development.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

STRICT HYGIENE! AVOID ALL CONTACT! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

URBAN AIR: Bantrol was not detected in air collected from Kitakyushu, Japan, in either July 1991 or April 1992 (detection limit=0.4 ng/cu m)(1).

highly toxic

DIFFERENTIAL FOLIAR...UPTAKE MAY...BE AFFECTED BY THE PRESENCE OR ABSENCE OF A SURFACTANT IN THE HERBICIDE FORMULATION.

LD50 Rat oral 110 mg/kg|LD50 Rat dermal 210 mg/kg|LD50 Rabbit oral 160 mg/kg|LD50 Mouse oral 200 mg/kg|For more Non-Human Toxicity Values (Complete) data for BANTROL (7 total), please visit the HSDB record page.

Bantrol's use as a selective contact herbicide outside of the United States(1,2), will result in its direct release to the environment(SRC).

TERRERSTRIAL FATE: IOXYNIL IS LOOSELY BOUND, PROBABLY TO THE COLLOIDAL FRACTION OF SOILS. DISAPPEARANCE IS LESS RAPID IN STERILE SOILS INDICATING THAT SOIL MICROBES AID BREAKDOWN. ... RESULTANT AVG PERSISTENCE: VIRTUALLY NO PREEMERGENCE EFFECT FROM NORMAL APPLICATION RATES @ ANY PERIOD AFTER SPRAYING.|TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 75(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that Bantrol will have high mobility in soil(SRC). Bantrol is expected to rapidly biodegrade in soil under aerobic conditions with a measured half-life of 9-10 days(4). Some degradation in anaerobic environments is possible; cyano-labelled Bantrol under anaerobic conditions released a small amount of 14CO2(5). Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(5). Volatilization of Bantrol should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.5X10-10 atm-cu m/mole(SRC), using a recommended regression equation(6). Volatilization from dry soil surfaces is not expected(SRC) based on an estimated vapor pressure of 1.4X10-7 mm Hg(SRC), from a fragment constant method(7).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 75(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), suggests that Bantrol will not adsorb to suspended solids and sediment in water(SRC). Based on soil studies, Bantrol is expected to biodegrade under aerobic conditions; some biodegradation may be seen in anaerobic environments(SRC). An aerobic biodegradation half-life of 9-10 days was measured in a clay loam soil with high organic matter content(3). Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(4). Bantrol should not volatilize from water surfaces based on an estimated Henry's Law constant of 5.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF value of 3(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Bantrol was stable for several weeks in natural water exposed to UV light; 10% degradation required greater than 1 month(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Bantrol, which has an estimated vapor pressure of 1.4X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Bantrol 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 about 75 days(3,SRC). Particulate-phase Bantrol may be physically removed from the air by wet and dry deposition(SRC).

DILUTE SOLUTIONS OF IOXYNIL WERE FOUND TO DECOMPOSE IN SUNLIGHT WITH LIBERATION OF IODIDE ION.../IN ONE STUDY, WHILE ANOTHER/ REPORTED THAT IRRADIATION IN BENZENE SOLN WITH MERCURY LIGHT RESULTED IN A FREE-RADICAL REACTION TO FORM 3,5-DIPHENYL-4-CYANOPHENOL.|The rate constant for the vapor-phase reaction of Bantrol with photochemically produced hydroxyl radicals has been estimated as 2.2X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 75 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Under oxidizing conditions, small amounts of iodine may be liberated from Bantrol in the same way as most 2-iodophenols(2). Exposure of benzene solutions of Bantrol to UV light for 20 hours results in the free-radical formation of 3,5-diphenyl-4-cyanobenzonitrile(3). Bantrol was stable for several weeks in natural water exposed to UV light; 10% degradation required greater than 1 month(4).

An estimated BCF value of 3 was calculated for Bantrol(SRC), using a measured log Kow of 0.90(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Koc of Bantrol is estimated as approximately 75(SRC), using a measured log Kow of 0.90(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that Bantrol has high mobility in soil(SRC). Alkaline soils adsorbed small amounts of Bantrol on soil particles(4).

The Henry's Law constant for Bantrol is estimated as 5.5X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that Bantrol will be essentially nonvolatile from water surfaces(2,SRC). Bantrol's estimated values for vapor pressure, 1.4X10-7 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).

SURFACE WATER: Bantrol was not detected in either surface waters or groundwater collected from the Granta catchment, United Kingdom, from 1985-1988 despite its use in the area (detection limit = 0.06 ug/l)(1). Surface water collected from the Anglian Water region in the United Kingdom from 1987 contained Bantrol in 2% of the samples with a maximum concentration of 0.1 ug/l(2). 1 of 48 soil water samples (0.09 ug/l), 0 of 20 drainage water samples, and 7 of 47 stream water samples (range = 0.01-0.7 ug/l) collected from the Hojvads Rende region in Denmark from 1989-1991 contained Bantrol(3). 0 of 54 soil water samples and 2 of 56 stream water samples (range = 0.01-0.05 ug/l) collected from the Bolbro Baek region in Denmark from 1989 to 1991 contained Bantrol(3).|RAINWATER: Rainwater, collected from 3 sites in Norway during June-September 1992, did not contain measurable concentrations of Bantrol (detection limit = 0.010 ppb)(1).

The general population may be exposed to Bantrol through the ingestion of contaminated food. Occupational exposure would be by inhalation or dermal contact. (SRC)

NO RESIDUES OF IOXYNIL WERE FOUND IN MILK OF DAIRY COW. NO IOXYNIL OR A POSSIBLE METABOLITE, 3,5-DIIODO-4-HYDROXYBENZOIC ACID, WERE FOUND IN THE MILK, URINE, OR FECES BY GAS CHROMATOGRAPHY ANALYSIS.|...IOXYNIL.../IS/ ABSORBED BY FOLIAGE & TRANSLOCATED. ...PRIMARY ROUTE OF FOLIAR PENETRATION...APPEARS TO BE CUTICULAR RATHER THAN STOMATAL... TRANSLOCATION STUDIES WITH (14)C-BROMOXYNIL HAVE SHOWN THAT MOST OF THE (14)C REMAINS IN TREATED LEAVES OF BOTH RESISTANT & SUSCEPTIBLE SPECIES. ... SIMILAR OBSERVATIONS, WHICH SUGGEST LIMITED SYMPLASTIC TRANSLOCATION, HAVE ALSO BEEN REPORTED FOR IOXYNIL.|AUTORADIOGRAPHY OF [CYANO-(14)C]IOXYNIL-TREATED MUSTARD, COTTON...BEAN, BARLEY, & PEA PLANTS HAS SHOWN THAT MOST OF THE RADIOACTIVITY REMAINS AT OR CLOSE TO SITE OF FOLIAR APPLICATION. BASIPETAL MOVEMENT OF (14)C TO BASE OF PETIOLE WAS OBSERVED IN MOST OF TREATED LEAVES AFTER 5 HR. FURTHER MOVEMENT UP THE STEM TO YOUNGER LEAVES & THE SHOOT APEX...WITH BYPASSING OF MATURE LEAVES WAS...OBSERVED. OUTWARD MOVEMENT TO TIPS OF TREATED LEAVES WAS NOTED, BUT TRANSLOCATION OF (14)C FROM TREATED ROOTS WAS LIMITED. STEM TREATMENTS RESULTED IN CONSIDERABLE UPWARD (14)C MOVEMENT, PARTICULARLY WHEN THE HERBICIDE WAS PLACED OVER AN INCISION. CONCENTRATED AREAS OF (14)C WERE NOTED IN THE VEINS OF THE LEAVES AFTER STEM TREATMENT.|... Binding /of ioxynil/ to human plasma proteins was compaired with that of T3, to gain insight into possible effects in humans. after incubating human serum with (125)I ioxynil, 2DIEP against anti-whole human serum and rocket immunoelectrophoresis against anti-TBPA, albumin or TBG were carried out. Ioxynil bound to TBPA but not to TBG nor albumin. The Ka calculated for the TBPA-ioxynil complex was 2.6x10(6) l mol/l. Ioxynil competed for the iodothymidine binding sites of TBPA.

FOUR DAYS AFTER FOLIAR TREATMENT WITH [CYANO-(14)C]IOXYNIL, UNCHANGED IOXYNIL, TRACE AMT OF BENZAMIDE & BENZOIC ACID DERIVATIVES, AND AT LEAST 2 OTHER UNKNOWN (14)C COMPOUNDS WERE TENTATIVELY IDENTIFIED IN RESISTANT BARLEY. ... THESE LIMITED DEGRADATION STUDIES /OF SUSCEPTIBLE COAST FIDDLENECK AND RESISTANT WINTER WHEAT/ SUGGEST THAT THE UNHINDERED NITRILE GROUPS OF ... IOXYNIL ARE SLOWLY HYDROLYZED IN THE PLANT TO THE CORRESPONDING BENZAMIDE AND BENZOIC ACID DERIVATIVES WITH POSSIBLE FURTHER DEGRADATION THROUGH DECARBOXYLATION, DEHALOGENATION, OR CONJUGATION OF THE BENZYL MOIETY OR THE AROMATIC RING. DECARBOXYLATION &...CONJUGATION REACTIONS MAY BE MUCH FASTER THAN HYDROLYSIS. THIS IS SUPPORTED BY THE DETECTION OF TRACE AMT OF THE HYDROLYSIS PRODUCTS & THE RAPID ACCUMULATION OF INSOLUBLE RESIDUES WITH (CYANO-14C)IOXYNIL...|BREAKDOWN OF IOXYNIL IN ROOT-TREATED BEAN PLANTS TO...BENZOIC ACID & IODIDE IONS HAS BEEN SUGGESTED & IODIDE HAS...BEEN SHOWN TO BE PRESENT IN BEAN PLANTS TREATED WITH IOXYNIL.

/Ioxynil is a/ highly active uncoupler of oxidative phosphorylation in plants & animals & inhibitor of photoreduction and photophosphorylation reactions in chloroplasts. ...higher concn of ioxynil ... also inhibit electron transport in isolated mitochondria and chloroplasts. ... Indirect evidence suggests that ioxynil ... causes a rapid and severe alteration in the energy balance of the plant cell. ... Levels of ATP were reduced 90% in excised soybean hypocotyls when compared to controls 3 hr after treatment with high concn (2X10-4 M) of ioxynil. ... The hormonal control of proteolytic and amylolytic enzyme activity in germinating seeds has been studied extensively. The studies indicate that ... ioxynil may either interfere with the development or transport of cytokinin & gibberellin hormones, or may interfere with the biosynthetic processes leading to enzyme formation.|Acts by inhibition of the second light reaction of photosynthesis...|The herbicide ... ioxynil ... inhibited energy dependent Ca(2)+ uptake in plant (maize, zucchini) mitochondria at a concn where /it/ did not inhibit ADP phosphorylation and did not interfere with tubulin polymerization. A common mechanism of action of /this herbicide/ is probably the inhibition of the regulation of cytoplasmic free Ca(2)+ concn which may in turn lead to many physiological malfunctions.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

SYMPTOMS OF POISONING: INCREASED BODY TEMPERATURE, SWEATING & INCR RESPIRATION.|FOUR WORKERS INVOLVED IN PRODUCTION OF IOXYNIL SUDDENLY DEVELOPED SUBACUTE POISONING. SYMPTOMS: WT LOSS DUE TO EXCESSIVE PERSPIRATION, FEVER, EMESIS. ELEVATED THIOCYANATE LEVELS IN URINE AND ENZYMES SGOT, CREATINE PHOSPHOKINASE, LACTATE DEHYDROGENASE & ALDOLASE WERE ELEVATED. THE URINARY THIOCYANATE LEVELS WERE ELEVATED IN THREE CASES (15-40 MG/L), WHILE NO AROMATIC AMINES WERE FOUND.|A 54 yr old man who had undergone gastrectomy swallowed a small amount of an unknown fluid, which he had stored with his homemade wine. He died 45 min later en route to the hospital. Chemical analysis ... established that the remaining material was ioxynil at a concn of 11.3%. It was estimated that the victim had swallowed 2000-3000 mg. Alcohol was also present at a concn of 0.135%. Autopsy revealed hyperemia of all organs, edema of the lungs, and edema of the brain with an occipital cone.|Signs and symptoms: Gastroenteritis, fever/hyperthermia (increased metabolic rate). /From table/

ioxynil

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Dizziness. Headache. Sweating. Vomiting. Weakness. Fever.

MAY BE ABSORBED! Pain. Redness.

Pain. Redness.

These incl aq concn of salts Actrilawn; emulsifiable concn of esters: Mate, Totril; mixtures incl as salts: Actril 3 (ioxynil + dichlorprop + MCPA); Actril 4, Actril S, Dantril, Tetroxone (ioxynil + bromoxynil + dichlorprop + MCPA), Certrol-Lin Onions; wettable powder (ioxynil + linuron), Certrol PA (ioxynil + dichlorprop + MCPA); Actril C, Iotox (ioxynil + mecoprop). As octanoates and esters: Actril DS (ioxynil + 2,4-D-isooctyl), Brittox (ioxynil + bromoxynil), Oxytril P (isoxynil + bromoxynil + dichlorprop-isooctyl).|AQ SOLN OF SODIUM SALT (25% WT/VOL EQUIV) IN AQ TETRAHYDROFURFURYL ALCOHOL.|ACTRIL C, ACTRIL M FOR USE ON WINTER AND SPRING SOWN CEREALS (IOXYNIL + MECOPROP SALTS). OXYTRIL CM FOR USE IN UNDERSOWN CEREAL CROPS WHERE CORN MARIGOLD IS A PROBLEM (IOXYNIL + BROMOXYNIL ESTERS), OXYTRIL M BRITTOX FOR USE IN WINTER AND SPRING-SOWN CEREALS (IOXYNIL + BROMOXYNIL + CMPP ESTERS). OXYTRIL P FOR USE ON SPRING-SOWN CEREALS (IOXYNIL + BROMOXYNIL). ACTRIL DS FOR USE IN SUGARCANE (IOXYNIL + 2,4-D ESTERS. IOTOX (IOXYNIL + CMPP SALTS) FOR USE IN SPORTS TURF. BRIOTRIL IS A MIXTURE OF BROMOXYL AND IOXYNIL.|Technical grade is circa 95% pure...|For more Formulations/Preparations (Complete) data for BANTROL (7 total), please visit the HSDB record page.

Introduced by May & Baker Ltd and by Amchem Products Inc (now Union Carbide Agricultural Products Co, Inc) (GBP 107033 to May & Baker Ltd; USP 3397054 to Union Carbide) as code number ACP 63-303 (Amchem for ioxynil); M&B 8873 (May & Baker for ioxynil), M&B 11641 (May & Baker for octanoate), 15830 RP (Rhone-Poulenc for octanoate); trade marks Certrol (Amchem for ioxynil and its esters), Mylone (Union Carbide for the esters), Actril (May & Baker for ioxynil and its esters), Mylone (Union Carbide for the esters), Actril (May & Baker for ioxynil and its octanoate), Totril (May & Baker for octanoate).|PHOTOLYSIS OF...IOXYNIL WAS FACTOR IN ITS HERBICIDAL ACTION. HERBICIDAL... ACTIONS...ARE MORE TOXIC IN LIGHT THAN DARK...|INCOMPATIBILITIES: WITH LIQUID FERTILIZERS & WATER SOLUBLE 2,4-D FORMULATIONS. PRETEST COMPATIBILITY WITH EMULSIFIABLE FORMULATIONS.|PHOTOSYNTHETIC & RESPIRATORY INHIBITOR /OF PLANTS/. THE ESTERS HAVE CAPACITY TO RESIST REMOVAL FROM FOLIAGE BY RAIN; ALKALI METAL SALTS DO NOT BECAUSE THEY ARE WATER SOLUBLE.|For more General Manufacturing Information (Complete) data for BANTROL (13 total), please visit the HSDB record page.

Product analysis is by titration or by estimation of iodine (HS Segal & ML Sutherland; Anal Methods Pestic, Plant Growth Regul Food Addit, 1967, 5, 423; Anal Methods Pestic Plant Growth Regul, 1972, 6, 654).|Residues may be determined by gas liquid chromatography of derivatives; TH Byast et al; Anal Methods Pestic, Plant Growth Regul Food Addit, 1967, 5, 423; (Tech Rep ARC Weed Res Organ, No 15 (2nd Ed), p 13) or by infra red spectrometry as ioxynil, or by HPLC after alkylation (EG Cotterill, Analyst, 1982, 107,76).|EIGHTEEN MIXED FORMULATIONS OF HERBICIDES SUCH AS IOXYNIL WERE ANALYZED BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY USING A 5-MUM NUCLEOSIL 50 COLUMN.|RESIDUES IN CROP SAMPLES: QUANT ESTIMATION IS BY GLC WITH ELECTRON CAPTURE DETECTOR.|For more Analytic Laboratory Methods (Complete) data for BANTROL (9 total), please visit the HSDB record page.

A high pressure liquid chromatographic method for determination of chlorophenoxy herbicides, bromoxynil, ioxynil in biological specimens to aid in diagnosis of acute /intoxication/.

Agrochemicals -> Herbicides|Herbicides, Transformation products|Environmental transformation -> Pesticides (parent, predecessor)

Ioxynil has known environmental transformation products that include 3,5-di-iodo-4-hydroxybenzoic acid.