Ioxynil (ISO)

Log Kow = 0.90 at pH 6.5

3.51

Faint phenolic /tech grade/

Odorless when pure

SOLUBILITY IN WATER @ 20-25 °C: 22% /LITHIUM SALT/; 14% /SODIUM SALT/; 10.7% /POTASSIUM SALT/

SOLUBILITY IN WATER: 0.005% @ 20 °C; IN CYCLOHEXANONE: 14%; IN DIMETHYLFORMAMIDE: 74%

SLIGHTLY SOL IN CHLOROFORM; SOL IN ETHER

AT 25 °C: IN ACETONE MORE THAN 10 G/100 ML; IN BENZENE 1.1 G/100 ML; IN CARBON TETRACHLORIDE 0.14 G/100 ML; IN METHANOL 3.3 G/100 ML; IN WATER 130 PPM

In water 50 mg/l (25 °C). In acetone 70, ethanol, methanol 20, cyclohexanone 140, tetrahydrofuran 340, dimethylformamide 740, chloroform 10, carbon tetrachloride <1 (all in g/l, 25 °C)

Solubility in water: none

212-213 °C

CREAM POWDER; FAINT PHENOLIC ODOR; MELTING POINT: 200 °C /TECHNICAL PRODUCT/

212-213 °C

0.00000014 [mmHg]

Vapor pressure: 2.77X10-5 mm Hg at 105 °C /Octanoate/

Less than 1 mPa at 20 °C

Vapor pressure, Pa at 20 °C:

Colorless odorless solid; [ICSC] Technical product is cream solid; Decomposed by sunlight and ultraviolet light; [HSDB] Powder; [MSDSonline]

ODOURLESS COLOURLESS CRYSTALS.

PRACTICALLY NON-VOLATILE

NO DETERIORATION IN LESS THAN 2 YEARS OF STORAGE

Very stable to acids and bases. Decomposed by sunlight and UV light.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]；H312: Harmful in contact with skin [Warning Acute toxicity, dermal]；H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H331: Toxic if inhaled [Danger Acute toxicity, inhalation]；H361d ***: Suspected of damaging the unborn child [Warning Reproductive toxicity]；H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

04/58/EC, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Ioxynil: Does not have an individual approval but may be used under an appropriate group standard

A mild skin and eye irritant; Can be absorbed through skin; May be a developmental toxin, based on animal studies; [ICSC] In acute poisoning, workers had vomiting, increase in body temperature, excessive perspiration, elevated thiocyanate in urine, and abnormal liver enzymes; No adverse effects were observed in 90-day 111 ppm oral study with rats; Inhibited oxidative phosphorylation in rat liver mitochondria; [HSDB] See Benzonitrile.

Ioxynil

Marine pollutant

Acute Tox. 3 (100%)；Acute Tox. 4 (100%)；Eye Irrit. 2 (100%)；Acute Tox. 3 (100%)；Repr. 2 (61.3%)；Repr. 2 (38.7%)；STOT RE 2 (100%)；Aquatic Acute 1 (100%)；Aquatic Chronic 1 (100%)

Reproductive toxicity - category 2；Acute toxicity - category 3；Acute toxicity - category 3；Acute toxicity - category 4；Eye irritation - category 2；Hazardous to the aquatic environment (acute) - category 1；Hazardous to the aquatic environment (chronic) - category 1；Specific target organ toxicity (repeated exposure) - category 2

Repr. 2；Acute Tox. 3 *；Acute Tox. 3 *；Acute Tox. 4 *；STOT RE 2 *；Eye Irrit. 2；Aquatic Acute 1；Aquatic Chronic 1

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.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

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.

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.

LD50 MALLARD ORAL 1200 MG/KG /TECHNICAL IOXYNIL OCTANOATE/

LD50 PHEASANT ORAL 1000 MG/KG /TECHNICAL IOXYNIL OCTANOATE/

LC50 HARLEQUIN FISH 3.3 PPM/48 HR /SODIUM SALT/

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).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.；Other Poison - Uncoupler

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

MAY BE ABSORBED! Pain. Redness.

Pain. Redness.

See Inhalation.

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).

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.../HAS/ HALF-LIFE OF LESS THAN 2 WK IN SOILS. WHEN STERILE SOILS WERE TREATED WITH IOXYNIL...LITTLE OR NO DEGRADATION WAS /DETECTED/... IN NONSTERILE SOILS...DEGRADATION WAS RAPID. DEGRADATION PRODUCTS FROM NONSTERILE SOILS TREATED WITH ...IOXYNIL WERE...IDENTIFIED AS THE BENZOIC ACID DERIVATIVES WITH TRACES OF INORGANIC IODIDE FROM IOXYNIL.

/Researchers/ attributed the reduced effectiveness of ... herbicide during adaptation studies to microbial degradation. Recent studies ... have also provided indirect evidence for the adaptation of Erwinia carotovora, Pseudomonas fluorescens, and Bacillus species to ioxynil.

In nonsterile soil, Bantrol was biodegraded to 3,5-diiodo-4-hydroxybenzoic acid through its intermediate amide; free iodine was also liberated(1). Degradation of both ring and cyano-labelled Bantrol to CO2 in a clay loam soil with high organic matter content was measured; 14CO2 was released more quickly initially from the cyano-labelled Bantrol(2). No 14CO2 was released from autoclaved soil or from ring-labelled Bantrol under anaerobic conditions(2). Cyano-labelled Bantrol under anaerobic conditions released a small amount of 14CO2. Metabolites from the aerobic biodegradation of Bantrol were 3,5-diiodo-4-hydroxybenzamide and 3,5-diiodo-4-hydroxybenzoic acid(2). The aerobic half-life of Bantrol degradation in a clay loam soil with high organic matter content was 9-10 days(3).

04/58/EC, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Ioxynil: Does not have an individual approval but may be used under an appropriate group standard

/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.

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.

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.

Used as selective contact herbicide for post-emergence control of many annual broad-leaved weeds in cereals, onions, flax, sugar cane, forage grasses, lawns, and freshly sown turf; Also used as a molluscicide; Not marketed in the US; Produced by Rhone-Poulenc in New Zealand (Axall), Ireland (Brottox), and Ethiopia and Kenya (Maytril); [HSDB]

Farming (Pesticides) [Category: Industry]

MOLLUSCICIDE

Selective contact herbicide with some systemic activity. Absorbed by the foliage...used for post-emergence control of a wide range of annual broad-leaved weeds, especially young seedlings of the Polygonaceae, Compositae, and Boraginaceae, in cereals, onions, leeks, garlic, shallots, flax, sugar cane, forage grasses, lawns, and newly-sown turf.

/IT IS USED FOR/ POST-EMERGENCE CONTROL FOR SEEDLING WEEDS (BINDWEED, SMARTWEED, BUTTERCUPS, CHICKWEED, CORNFLOWER, DANDELION, FAT HEN, GROUNDSEL, MAYWEEDS, MUSTARDS, PLANTAINS, SHEPHERDSPURSE, SPEEDWELLS, ETC) IN CEREALS. BELGRAN, CERTROL DS FOR SUGAR CANE. ACTRIL DS FOR SUGARCANE, CITRUS, RICE, AND OIL PALM. IOTOX FOR SPORTS TURF.

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.

Herbicides, Transformation products

Environmental transformation -> Pesticides (parent, predecessor)；Environmental transformation -> Pesticide transformation products (metabolite, successor)

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.