2439-10-3CC(=O)O.CCCCCCCCCCCCN=C(N)NYIKWKLYQRFRGPM-UHFFFAOYSA-NDodine is a white crystalline solid. Used as a fungicide.
Pesticide -> EPA IRIS
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Fungicides
Fungicides
Pesticide (Dodine) -> USDA PDB
Slightly waxy solid
Colorless crystals
Sol in alcohol, hot water; slightly sol in other solvents.
Insol in most org solvents. Readily sol in mineral acids.
IN LOW MOL WT ALCOHOLS RANGES FROM ABOUT 7% TO 23% @ ROOM TEMP; SOL IN ACIDS; 0.063% BY WT IN WATER @ 25 °C.
In distilled water 0.07%. Soluble in methanol, ethanol. Practically insoluble in most organic solvents.
In water, 630 mg/l @ 25 °C
0.00000015 [mmHg]
1.5X10-7 mm Hg @ 25 °C
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Regulation (EC) No 396/2005 (amended)
Dodine is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2011/9/EU, Reg. (EU) 2020/2007, Reg. (EU) 2026/372 , Reg. (Eu) 2024/1206, Reg.(EU) 2018/1266, Reg.(EU) No 540/2011
Dodine: HSNO Approval: HSR003128 Approved with controls
A strong skin and eye irritant (concentrations >50%); [Hawley] Dodine and DGH (Dodecylguanidine hydrochloride) are toxicologically equivalent; No evidence of carcinogenicity; No evidence of reproductive or neurological toxicity; [EPA REDs] A skin, eye, and GI tract irritant; [HSDB] A skin and eye irritant; [eChemPortal: ESIS] See Dodecylguanidine hydrochloride.
... 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.
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 ... .
Used as agricultural fungicide; [Merck Index] Used primarily on fruits and nuts; A similar product, dodecylguanidine hydrochloride (DGH) is used as a biocide against algae, fungi, and slime-forming bacteria; [EPA REDs]
Farming (Pesticides) [Category: Industry]
For Cyprex (USEPA/OPP Pesticide Code: 044301) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Dodecylguanidine salts ... are highly effective for agricultural applications, particularly in the control of apple scab and cherry leaf spot. They are also effective algal growth inhibitors, useful in the manufacture of microorganisms-stable oil and water emulsions and in treatment of saline process water. /Dodecylguanidine salts/
Fungicide
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2439-10-3DTXSID3020548CHEMBL450348、CHEMBL74474CHEBI:74889Dodine is a white crystalline solid. Used as a fungicide.
Colorless solid; [HSDB]; [MSDSonline] White solid; [CAMEO]
FREE BASE, REG NUMBER (112-25-2), IS LIBERATED BY CONCENTRATED ALKALI.
CMPD IS SURFACE-ACTIVE; SALT OF STRONG BASE & WEAK ACID.
化学的特性White Solid
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Dodine is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0161; Pesticide type: fungicide, antimicrobial; Registration Standard Date: 02/26/87; Case Status:OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Dodine; Data Call-in (DCI) Date(s): 12/09/91, 06/16/92, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Tolerances are established for residues of the fungicide dodine (n-dodecylguanidine acetate) in or on the following raw agricultural commodities: apples; cherries, sour; cherries, sweet; meat; milk; peaches; pears; pecans; strawberries; and walnuts.
Tolerances with regional registration, as defined in 180.1(n), are established for residues of dodine in or on the following raw agricultural commodities: spinach.
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.
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute toxicity (Oral) - Category 4
Acute Tox. 4 *
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.
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))
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 ... .
Tolerances are established for residues of the fungicide dodine (n-dodecylguanidine acetate) in or on the following raw agricultural commodities: apples, 5.0 ppm; cherries, sour, 5.0 ppm; cherries, sweet, 5.0 ppm; meat, 0 ppm; milk, 0 ppm; peaches, 5.0 ppm; pears, 5.0 ppm; pecans, 0.3 ppm; strawberries, 5.0 ppm; and walnuts, 0.3 ppm.
Tolerances with regional registration, as defined in 180.1(n), are established for residues of dodine in or on the following raw agricultural commodities: spinach, 12.0 ppm.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Protective clothing: goggles, face shield, rubber gloves when handling.
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.
LC50 Gammarus fasciatus 1.1 mg/l/96 hr. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/l as calcium carbonate and alkalinity of 30-35 mg/l.
LD50 Mallard duck oral 1142 mg/kg
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)
Dodine
Endocrine
4 x 10 ^-3 mg/kg-day
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).
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.
Achromobacter and Flavobacterium species, both common to soil, can grow with cyprex as the sole source of carbon(1). When river mud from the Denver area was treated with 14C-labeled cyprex, five percent of the fungicide was degraded in 68 days(1).
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).
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Dodine is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0161; Pesticide type: fungicide, antimicrobial; Registration Standard Date: 02/26/87; Case Status:OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Dodine; Data Call-in (DCI) Date(s): 12/09/91, 06/16/92, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Tolerances are established for residues of the fungicide dodine (n-dodecylguanidine acetate) in or on the following raw agricultural commodities: apples; cherries, sour; cherries, sweet; meat; milk; peaches; pears; pecans; strawberries; and walnuts.
Tolerances with regional registration, as defined in 180.1(n), are established for residues of dodine in or on the following raw agricultural commodities: spinach.
Dodine may be made by the reaction of dodecyl chloride with sodium cyanamide followed by treatment of the product of the first reaction with ammonia. Dodine may also be made by the reaction of dodecyl amine with cyanamide in the presence of acetic acid.
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.
Fungicides
FUNGICIDES
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.
用途農業用殺菌剤
使用Dodine is used to control scab on apples, pears and pecans, leaf spot diseases of cherries, olives, blackcurrants, celery and other crops, and foliar diseases of strawberries. It is also used on other fruit, vegetable, nut and ornamental crops and shade trees.
一般的な説明White crystalline solid. Used as a fungicide.
定義ChEBI: An acetate salt resulting from the reaction of equimolar amounts of 1-dodecylguanidine and acetic acid. It is used as a fungicide to control black spot and foliar diseases on apples, pears, peaches, nectarines and strawberries.