Dodine

287.44

287.257263

219-459-5

259C423Y98

3082

DTXSID3020548

Slightly waxy solid|Colorless crystals

2925290014

102

4.67220

Dodine is a white crystalline solid. Used as a fungicide.

0.9636 (rough estimate)

136 °C

352.8ºC at 760 mmHg

>100 °C

In water, 630 mg/l @ 25 deg C

0-6°C

5 x 10 -6 Pa (20 °C, est.)

Oral-Rat LD50: 660 mg/kg; Oral-Mouse LD50: 266 mg/kg

Combustion produces toxic nitrogen oxide gas

pKa = 9

FREE BASE, REG NUMBER (112-25-2), IS LIBERATED BY CONCENTRATED ALKALI.|CMPD IS SURFACE-ACTIVE; SALT OF STRONG BASE & WEAK ACID.

Soluble in hot water.

Salts, Acidic

Acidic organic/inorganic salts, such as DODINE, are generally soluble in water. The resulting solutions contain moderate to high concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Noncorrosive

UN 3077

3

22-36/38-50/53

26-60-61

MF1750000

Xn;N,N,Xn

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

AT ORDINARY TEMP CMPD IS STABLE AS SOLID OR IN SOLN; STABLE UNDER MODERATELY ALKALINE OR ACID CONDITIONS.

P273-P305 + P351 + P338-P501

H302-H315-H319-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.|Recommendable methods: Incineration. Peer-review: Large amt: Incinerate in a unit equipped with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

It is incompatible with lime and anionic surfactants.|... Incompatible with chlorobenzilate, lime, sulfur, oils, oil emulsions, & hard water.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 139 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P260, P264, P270, P271, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P314, P320, P321, P330, P332+P313, P362, P403+P233, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Protective clothing: goggles, face shield, rubber gloves when handling.

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.|TRANSFER OR MIX /PRODUCT/ WITH ADEQUATE VENTILATION ... .

Strong irritant to eyes and skin over 50% concentration.|It ... is irritating to skin, eyes, and gastrointestinal tract.|Cause severe irritation of the skin and eyes when there is contact with strong solutions.

Cyprex was not found in ambient air during a nationwide air monitoring program operated during 1970 and 1971 by the USEPA(1).

highly toxic

MICE WERE TREATED INTRAGASTRICALLY DURING LAST WEEK OF PREGNANCY WITH DODINE & SODIUM NITRITE 0.05%. MALIGNANT LYMPHOMAS, LUNG ADENOMAS & HEPATOMAS OCCURRED IN 30-70%. IN PARENT GENERATION TUMORS APPEARED 4 MO AFTER DELIVERY & AT 6-7 MO IN F1 GENERATION. SPONTANEOUS TUMORS IN CONTROLS WERE 6%. DODINE ALONE HAD NO EFFECT ON CANCER INCIDENCE.|Dodine at 60 mg/kg for 8 days and sodium nitrite at 22.5 mg/kg alone or in combination altered liver structure in male rats. The liver alterations incl reduced granular endoplasmic reticulum, incr smooth endoplasmic reticulum, polymorphism and mitochondrial edema, incr lysosome numbers, glycogen reduction, collagen proliferation, incr Kupffer cell numbers. The alterations were more marked by the combination of the chemicals, the endoplasmic reticulum being particularly affected.|Oral admin of 1/10 LD50 sodium nitrite and dodine, individually or in combination, to rats enhanced the activity of glutamic-oxaloacetic transaminase, glutamic-pyruvic transaminase, lactate dehydrogenase, glucose 6-phosphate dehydrogenase, isocitrate dehydrogenase, and succinate dehydrogenase, reduced the activity of cholinesterase, and decr the concn of total protein, all in the blood serum. Quant estimation of the results from liver functional investigations revealed a summation of the toxic effect, tending to potentiation with combined exposure of the two agents.|A single oral admin of 22.5 mg/kg of sodium nitrite (0.1 LD50) alone or in combination with 60 mg dodine (0.1 LD50) inhibited mixed-function oxidase of rat liver microsomes by 28.7-36 and 64-68.6%, respectively, whereas dodine alone was ineffective. The dodine addition also prolonged the enzyme depression. Within 30 days the enzyme activities approached the normal level. Only dodine-sodium nitrite lowered the microsomal protein by 15.5-21.6% on days 2, 4, and 15 after the administration. Nitrosation of dodine by sodium nitrite potentiates the effect of sodium nitrite.|Experiments were carried out on albino rats in which 1/10 LD50 sodium nitrite and dodecylguanidineacetate were given orally & in combination. The activity of mixed function oxidases was determined at 2 levels of biological organization: the intact organism after loading with aminopyrine & subsequent determination of its basic metabolites in the urine; subcellular level (microsomal liver fraction) by the velocity of N-demethylation of aminopyrine, hydroxylation of aniline and by the cytochrome p450 content. The combined action of the 2 agents caused considerable mixed function oxidases inhibition (63-67%) on the 1st, 2nd, 4th and 15th days at both levels. A new compound is apparently formed under the conditions of the experiment, probably through in vivo nitrosification of the pesticide. This is testified by the established qualitatively different effects of the preliminary induction of mixed function oxidases with phenobarbital on the acute toxicity of the noxae studied: lack of effect for dodecyclguanidineacetate, increase for sodium nitrite and decrease for their combination.

LD50 Rat (male) oral approx 1000 mg/kg|LD50 Rabbit percutaneous >1500 mg/kg|LD50 Rat percutaneous >6000 mg/kg|LD50 Rat dermal >6000 mg/kg|For more Non-Human Toxicity Values (Complete) data for CYPREX (10 total), please visit the HSDB record page.

Cyprex's production and use as a fungicide(1) will result in its direct release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1X10+5 measured in soil(2), indicates that cyprex is expected to be immobile in soil(SRC). The pKa of cyprex is 9(3), indicating that this compound will primarily exist as the cation in the environment. Cyprex is also a salt and will be dissociated in the environment. Volatilization from moist soil surfaces is not expected to be an important fate process for cyprex because cations and salts are not expected to volatilize(SRC). When river mud from the Denver area was treated with 14C-labeled cyprex, only five percent of the fungicide was degraded in 68 days(4), which suggests biodegradation will occur slowly in soils(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1X10+5 measured in soil(2), indicates that cyprex is expected to adsorb to suspended solids and sediment(SRC). A pKa of 9(4) indicates that cyprex will exist almost entirely in the ionized form at environmental pH values and therefore volatilization from water surfaces is not expected to be an important fate process, particularly in acid to neutral environments. In addition, cyprex is a salt and will exist in the dissociated form in the environment; therefore, volatilization from water surfaces is not expected to occur. According to a classification scheme(5), an estimated BCF of 16(SRC), calculated from its water solubility of 630 mg/l(6) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low (SRC). When river mud from the Denver area was treated with 14C-labeled cyprex, only five percent of the fungicide was degraded in 68 days(7), which suggests biodegradation will occur slowly in water(SRC).|ATMOSPHERIC FATE: Since cyprex is an acetate salt of dodecylguanidine, it will not be found in the vapor phase in the atmosphere; cyprex will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cyprex may be removed from the air by wet and dry deposition. (SRC)

The pKa of cyprex is 9(1), which indicates that this compound will primarily exist as a cation in the environment.

Cyprex, an acetate salt of dodecylguanidine, is expected to exist in the dissociated form in aquatic environments. An estimated BCF value of 16 was calculated for non-dissociated cyprex(SRC), using a water solubility of 630 mg/l(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).

Cyprex is an organic base that has a pKa of 9(1), which indicates that cyprex will exist primarily as a cation in moist soils and cations adsorb strongly to soils(SRC). The Koc of cyprex measured in soil is 1X10+5(2). According to a classification scheme(3), this Koc value suggests that cyprex is expected to be immobile in soil(SRC).

Cyprex is an organic base with a pKa of 9(1) and an acetate salt, which indicates that cyprex will be dissociated and exist primarily as a cation under environmental conditions and will not volatilize from moist soils or waters(SRC). Cyprex is not expected to volatilize from dry soil surfaces(SRC) based on its vapor pressure of 1.5X10-7 mm Hg at 25 °C(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,403 workers (none of these are female) are potentially exposed to cyprex in the US(1). The NOES data do not include farm workers who are likely to be exposed to these compounds. Occupational exposure to cyprex may occur through inhalation and dermal contact with this compound at workplaces where cyprex is produced or used(SRC).

NO TRANSLOCATION FROM FOLIAGE TO FRUIT & DEGRADATION PRODUCTS TRANSLOCATED ONLY VERY SLIGHTLY.|TRACES OF RADIOTAGGED CARBON APPEARED IN FRUIT. ... MOST OF RADIOACTIVITY SETTLED IN PROTEIN OR PEPTIDE PORTION OF FRUIT /AFTER APPLICATION TO APPLE TREES/.|It is absorbed across the skin ... .

... DEGRADATION OF (14)C DODINE OCCURRED AFTER APPLICATION TO APPLE TREES. ... ONE OF 4 CMPD DETECTED APPEARED TO BE GUANIDINE OR GUANIDINE MONOSUBSTITUTED WITH SMALL GROUP. NO METABOLITES HAVE BEEN DEMONSTRATED /IN FUNGI/.|IN PLANTS, DODINE IS CONVERTED TO CREATINE VIA THE ACTION OF A METHYLTRANSFERASEAND SIMULTANEOUS OXIDATIVE CLEAVAGE OF THE DODECYL MOIETY.

... DODECYLGUANIDINE INHIBITS OXIDATION OF GLUCOSE BY CELLS OF FUNGUS (SACCHAROMYCES PASTORIANUS). OTHER STUDIES ATTRIBUTE TOXICITY OF DODINE TO BLOCKING OF VITAL ANIONIC SITES @ CELL SURFACE & INACTIVATION OF ENZYMES.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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. 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. (ERG, 2016)

INGESTION CAUSES VOMITING, DIARRHEA.|ENVIRONMENTAL CHEMICALS INCL PESTICIDES CARRYING SECONDARY AND TERTIARY AMINO GROUPS ARE SUGGESTED TO BE A HEALTH HAZARD TO MAN SINCE POTENTIALLY CARCINOGENIC NITROSO COMPOUNDS MAY BE FORMED IN THE PRESENCE OF NITRITE AT LOW pH VALUES RESEMBLING CONDITIONS IN THE HUMAN STOMACH.|Cause severe irritation of the skin and eyes when there is contact with strong solutions.

Carpen

FUNGICIDE, OF WHICH APPROXIMATELY 64% IS USED ON APPLES AND 36% ON OTHER DECIDUOUS FRUITS AND NUTS (1975).

USEPA/OPP Pesticide Code 044301; Trade Names: Cytox 2160; Cyprex; AC 5223; Melprex.|... Include wettable powder (650 and 800 ai/kg); liquid (200 and 250 g/l); dust (750 g/kg).|A COMBINATION OF DODINE & CAPTAN HAS ALSO SHOWN PROMISE, PARTICULARLY IN PREVENTING FRUIT INFECTION.

Guanidine, N-dodecyl-, acetate (1:1): ACTIVE|Discontinued by American Cyanamide Co.|... PERFORM DOUBLE ROLE OF RESIDUAL PROTECTION & PARTIAL THERAPY OF ESTABLISHED INFECTIONS. FUNGUS IS NOT KILLED BUT IS INHIBITED FROM DEVELOPING FURTHER. THIS INCLUDES LARGE GROUP OF POPULAR FUNGICIDES SUCH AS ... DODINE ... .|... Is an effective contact fungicide against early infections of the apple scabfungus and destroys the fungus effectively because it invades only the superficial epidermal layer of the apple leaf ... . Even though the fungus /Diplocarpon earliana/ is very susceptible to the fungitoxicity of dodine, the fungicide functions only as a residual or contact protectant to destroy the spores before they can become established. /Monilinia fructicola/ infects the acid tissues of fruits ... dodine loses its fungitoxicity as the medium becomes acid. The brown rot fungus is inhibited at very low concn, near 5 ppm, by dodine in spore germination tests, but will not affect fungal growth on the peach fruit at 1600 ppm.|CLASSIFICATION OF SOME OF COMMON FUNGICIDES INDICATING THEIR CHARACTERISTICS AS OBSERVED FROM FIELD EXPT: DODINE; RESIDUAL 3, CONTACT 2, TOPICAL THERAPY 2, FUNGICIDAL 3, FUNGISTATIC 1. 1= LIGHTLY EFFECTIVE OR RESPONSIVE; 2= MODERATELY EFFECTIVE OR RESPONSIVE; 3= STRONGLY EFFECTIVE OR RESPONSIVE. /FROM TABLE/|For more General Manufacturing Information (Complete) data for CYPREX (12 total), please visit the HSDB record page.

DODINE RESIDUES WERE EXTRACTED FROM APPLE & CHERRIES ... IN METHANOL. ... DODECYLQUANIDINE CATION IS EXTRACTED FROM CHLOROFORM INTO AQ ALKALI & MEASURED COLORIMETRICALLY.|A GLC METHOD WAS DEVELOPED FOR THE DETERMINATION OF DODINE RESIDUES ON FRUIT CROPS. THE METHOD YIELDS MEAN RECOVERIES OF 84% OR GREATER FROM 0.05-10.0 PPM OF RESIDUES AND HAS A LOWER DETECTABLE LIMIT OF 8 PPB. CONFIRMATION OF THE DERIVATIVE BY GLC/MS IS DESCRIBED.|AOAC Method 964.19. Dodine Pesticide Residues by Spectrophotometric Method.|/Product analysis is by/ dissolution in a mixture of acetic acid and acetic anhydride and potentiometric titration with perchloracetic acid. Residue analysis is by colorimetric of a derivative.|For more Analytic Laboratory Methods (Complete) data for CYPREX (6 total), please visit the HSDB record page.

Agrochemicals -> Fungicides|Fungicides|FUNGICIDES