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Crufomat (ISO)

Crufomate

HCID 9300
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Grundinformationen

CAS
299-86-5
Standard-SMILES
CNP(=O)(OC)Oc1ccc(C(C)(C)C)cc1Cl
InChIKey
BOFHKBLZOYVHSI-UHFFFAOYSA-N
Summenformel
C12H19ClNO3P
Durchschnittliche Molmasse
291,71 g/mol
Monoisotopische Masse
291,0791082

Überblick

Crufomate is a white crystalline solid Mp: 61.5 °C. The commercial product is a yellow oil. A phosphoramidate insecticide.

Namen und Bezeichner

Bevorzugter Name
Crufomate
IUPAC
N-[(4-tert-butyl-2-chlorophenoxy)-methoxyphosphoryl]methanamine
Lokaler Name
Crufomat (ISO)
Englischer Name
CRUFOMATE
Summenformel
C12H19ClNO3P
Molmasse
291.71

Namen und Synonyme

Crufomate299-86-5RUELENEMontrelAmidofosAmidophosRuleneRuelene drenchDowco 132Crufomate ACrufomatCrufomato
Weitere Namen anzeigen
4-tM-1261dowdo132
Ruelene 25ERuereneCrufomatumDTXSID1037515NSC 2534634-tert-Butyl-2-chlorophenyl methyl methylphosphoramidateNSC-253463Phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester

Datenbank-Bezeichner

CAS
299-86-5
PubChem CID
9300
DTXSID
DTXSID1037515
ChEMBL
CHEMBL1880767
ChEBI
CHEBI:82111
UNII
V82Q65924L
EC Number
206-083-1
Nikkaji
J5.472K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
47,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
18
Formalladung
0
Komplexität
319

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 2 Einträge

Pesticides -> Organophosphate Insecticides

Pesticide (Crufomate) -> USDA PDB

LogP3.42
Density · 5 Einträge

1.16 (NIOSH, 2024) - Denser than water; will sink

1.1618 @ 70 °C/4 °C

Relative density (water = 1): 1.5

1.16

1.16

Color/Form · 4 Einträge

WHITE CRYSTALLINE SOLID

CRYSTALS FROM PETROLEUM ETHER

Colorless

White, crystalline solid in pure form [Note: Commercial product is a yellow oil].

Solubility · 6 Einträge

Insoluble (NIOSH, 2024)

PRACTICALLY INSOLUBLE IN LIGHT PETROLEUM, WATER; SOL IN ACETONE, BENZENE, CARBON TETRACHLORIDE; SOL UB ACETONE, BENZENE, CARBON TETRACHLORIDE

READILY SOL IN ACETONITRILE

SOL IN ETHYL ETHER, METHANOL, CYCLOHEXANE

Soluble in alcohol

Solubility in water: none

Boiling Point · 4 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302+H312 (92.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]

P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory InformationThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelClass 9
Fire Hazards · 2 Einträge

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

Combustible. Liquid formulations containing organic solvents may be flammable.

Health HazardsExcerpt from NIOSH Pocket Guide for Crufomate:
Hazards Summary · 1 Eintrag

A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; [ICSC] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 5 Einträge

The signs of poisoning due to organophosphorus cmpd are those due to accumulation of acetylcholine & hence overstimulation of parasympathetic nervous system. It is usual to divide them under 3 headings: muscarinic, nicotinic & central. Muscarinic signs ... consist of hypersalivation, lacrimation, sweating & nasal discharge. Miosis, dyspnea, vomiting, diarrhea & frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness & paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions & coma. Death is due to resp failure, or sometimes cardiac arrest. There is little difference between signs produced by different organophosphorus compounds, but route of absorption may influence one system more than another. /Organophosphorus cmpd/

The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/

The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/

For more Mechanism of Action (Complete) data for RUELENE (7 total), please visit the HSDB record page.

Zugehörige Reaktionen

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Decomposes (NIOSH, 2024)

117-118 °C at 0.01 mm Hg

decomposes

Decomposes

Decomposition · 2 Einträge

When heated to decomposition it emits very toxic fumes of phosphorus oxides, nitrogen oxides, and Cl-.

60-65 °C

Melting Point · 4 Einträge

140 °F (NIOSH, 2024)

60-60.5 °C

140 °F

140 °F

Vapor Pressure · 6 Einträge

0.01 mmHg at 243 °F (NIOSH, 2024)

0.0000375 [mmHg]

0.01 MM HG AT 117 °C

Vapor pressure, Pa at 25 °C: 0.106

0.01 mmHg at 243 °

(243 °F): 0.01 mmHg

Physical Description · 5 Einträge

Crufomate is a white crystalline solid Mp: 61.5 °C. The commercial product is a yellow oil. A phosphoramidate insecticide.

White, crystalline solid in pure form. [pesticide] [Note: Commercial product is a yellow oil.]; [NIOSH]

WHITE CRYSTALS.

White, crystalline solid in pure form. The commercial product is a yellow oil.

White, crystalline solid in pure form. [pesticide] [Note: Commercial product is a yellow oil.]

Stability/Shelf Life · 3 Einträge

RELATIVELY STABLE AT PH 7.0 OR BELOW AND UNSTABLE IN STRONGLY ACID MEDIA

UNSTABLE OVER LONG PERIODS IN WATER PREPARATIONS, AT TEMPERATURES ABOVE 60 °C, & IN ALKALI.

Unstable over long periods in aqueous preparations or above 140 degrees F.

Physikochemische Eigenschaften

Schmelzpunkt
60 ℃ · 60℃
Siedepunkt
0.01 · bp0.01 117-118°
Dichte
1.176 · 1.176
Brechungsindex
20 · nD20 1.5142
Aggregatzustand
solid
pka
0.05 · 0.05±0.70(Predicted)
Wasserlöslichkeit
4.975 g/L · 4.975g/L(temperature not stated)
Henry's Law Constant
3.9 · 3.9×103 mol/(m3Pa) at 25℃, HSDB (2015)
EPA chemische Informationen
Crufomate (299-86-5)
Reactive GroupAmines, Phosphines, and Pyridines
EC ClassificationSymbol: Xn, N; R: 21/22-50/53; S: (2)-36/37-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
FIFRA Requirements40 CFR Part 180 was amended by removing section 180.295 Crufomate; tolerances for residues.
Reactivity Profile · 1 Eintrag

CRUFOMATE is combustible; liquid formulations containing organic solvents may be flammable. Incompatible with strongly basic and strongly acidic materials. Unstable over long periods in aqueous preparations or above 140 °F. Emits toxic fumes of POx, Cl2 and NOx when heated to decomposition (Hazardous Chemicals Desk Reference p. 272 (1987)).

Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including hydrogen chloride, nitrogen oxides and phosphorus oxides. Reacts with strong acids and strong bases.
Flammable LimitsCombustible Solid

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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

Use water spray, powder.

First Aid Measures · 4 Einträge

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.

Refer for medical attention .

First Aid · 2 Einträge

Excerpt from NIOSH Pocket Guide for Crufomate:

(General first aid procedures)

Safe StorageSeparated from strong bases, strong acids and food and feedstuffs. Well closed. Keep in a well-ventilated room.
Exposure Control and Personal Protection · 1 Eintrag

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Fire Fighting Procedures · 1 Eintrag

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

Storage Conditions · 3 Einträge

Rooms used for storage only should be soundly constructed & fitted with secure locks. Floors should be kept clear & pesticides clearly identified. If repacking is carried out in storage rooms, adequate light should be available; floors should be impervious & sound ... . /Pesticides/

Pesticides containers must be provided with labels indicating the degree of toxicity of the product they contain. The labels must not only give a short description of how to use the prepn, but also state basic precautions to be taken when applying it. /Organophosphorus pesticides/

Pesticides of any degree of toxicity should be transported in containers which are clearly labelled, leak-proof, and not easily damaged. They should never be transported /or stored/ beside, or above any type of food, and all spillages should be immediately reported. /Pesticides/

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 3 Einträge

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.

All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/

Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/

Spillage Disposal · 1 Eintrag

Personal protection: complete protective clothing including self-contained breathing apparatus. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Preventive Measures · 5 Einträge

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

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.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

For more Preventive Measures (Complete) data for RUELENE (12 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Toxikologische Informationen

Interactions · 5 Einträge

SINGLE ORAL DOSES OF RUELENE WERE ADMIN TO RATS TOGETHER WITH EACH OF THE 14 THEN-COMMERCIAL CHOLINESTERASE-INHIBITING INSECTICIDES. NO COMBINATION PRODUCED GREATER THAN ADDITIVE RATIOS OF EXPECTED TO OBSERVED LD50 VALUES EXCEPT RUELENE WITH MALATHION, WHERE THE RATIO WAS 5:3.

DO NOT USE IN CONJUNCTION WITH OR WITHIN A FEW DAYS OF ... ANY OTHER CHOLINESTERASE INHIBITING CMPD. (AVOID USE WITH PHENOTHIAZINE, PHENOTHIAZINE TRANQUILIZERS). /COUMAPHOS/

Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/

In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/

For more Interactions (Complete) data for RUELENE (6 total), please visit the HSDB record page.

Target OrgansEyes, skin, respiratory system, blood cholinesterase
Ecotoxicity Values · 3 Einträge

LC50 GAMMARUS FASCIATUS 3.7 MG/L/96 HR AT 15 °C (95% CONFIDENCE LIMIT: 3.4-4.1 MG/L), MATURE 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.

LC50 LEPOMIS MACRCHIRUS (BLUEGILL) 1.8 MG/L AT 8 °C (95% CONFIDENCE LIMIT: 1.3-2.4 MG/L), WT 1.0 G 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 Anas platyrhynchos (Mallard) oral 265 (confidence limits 170-414) mg/kg /purity 92%/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that ruelene is expected to have low mobility in soil(SRC). Volatilization of ruelene from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 2.5X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Ruelene is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.8X10-5 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data for ruelene are not available(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that ruelene is expected to adsorb to suspended solids and sediment in water(SRC). Ruelene is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 230(3,SRC), from an experimental log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is high(SRC). Biodegradation data for ruelene are not available(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ruelene, which has an estimated vapor pressure of 3.8X10-5 mm Hg at 25 °C(2,SRC), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ruelene 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 ll hours(3,SRC). Particulate-phase ruelene may be physically removed from the air by wet and dry deposition(SRC).

Adverse EffectsOther Poison - Organophosphate
Exposure Routes · 2 Einträge

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Milk Concentrations... WILL PASS INTO MILK OF TREATED ANIMALS.
Signs and Symptoms · 5 Einträge

Dizziness. Sweating. Laboured breathing. Nausea. Unconsciousness. Vomiting. Pupillary constriction, muscle cramp, excessive salivation.

MAY BE ABSORBED! Redness. Further see Inhalation.

Redness. Pain.

Abdominal cramps. Diarrhoea. Nausea. Vomiting. Pupillary constriction. Muscle cramps. Excessive salivation.

irritation eyes, skin, respiratory system; wheezing, dyspnea (breathing difficulty); blurred vision, lacrimation (discharge of tears); sweating; abdominal cramps, diarrhea, nausea, anorexia

Acute Toxicity LinkChemical: CRUFOMATE
ICSC Environmental DataThe substance is very toxic to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
Medical Surveillance · 4 Einträge

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications /meaning further clinical evaluations/ for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should /be protected from exposure from/ pesticides. /Organophosphorus pesticides/

... Surveillance of workers could be carried out through measurement of blood or urinary levels of the cmpd to which they are exposed, or through measurement of a metabolite. /Organic phosphorus pesticides/

... There is no change in red blood cell cholinesterase activity in adults associated with age. ... Activity of this enzyme increases progressively during the first year of life, it is higher in children under 3 yr of age than in older children, and it is markedly higher in 5 yr old children than in 3 yr olds. /Organic phosphorus pesticides/

Cholinesterase activity of plasma is significantly higher in men than in women, and this is true no matter which of several choline esters are used as substrate in measuring the enzyme activity. According to some, the difference is confined to young people. There is no sex difference in the red cell enzyme activity. Serum cholinesterase activity of blacks tends to be lower than whites of the same sex. /Organic phosphorus pesticides/

Soil Adsorption/Mobility · 1 Eintrag

The Koc of ruelene is estimated as approximately 1,700(SRC), using a measured log Kow of 3.42(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that ruelene is expected to have low mobility in soil(SRC).

Regulatorische Informationen

FIFRA Requirements40 CFR Part 180 was amended by removing section 180.295 Crufomate; tolerances for residues.

Sicherheitsdaten

OEB
B
OEL
TWA: 5 mg/m3, STEL: 20 mg/m3
ridadr
UN2783 (solid)
hs_code
29299090
risk_code
21/22-50/53
Toxizität
LD50 in male, female rats (mg/kg): 635, 460 orally (Gaines)
hazard_code
Xn,N
safety_code
36/37-60-61
Giftige Stoffe Daten
299-86-5(Hazardous Substances Data)
Metabolism/Metabolites · 5 Einträge

AFTER INCUBATION OF RUELENE WITH /SHEEP/ WHOLE BLOOD AND PLASMA, CHROMATOGRAPHY SHOWED PRESENCE OF DIMETHYLAMIDO PHOSPHORIC ACID AND PHENYLMETHYL PHOSPHORIC ACID. SEVERAL OTHER METABOLITES WERE FOUND BUT NOT COMPLETELY INDENTIFIED. RUELENE WAS FED TO LAYING HENS AT ... 100 PPM FOR 7 DAYS. 6 METABOLITES WERE ISOLATED FROM EXCRETA. ... O-METHYL-PHOSPHORIC ACID AND 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID WERE ... IDENTIFIED. SHEEP AND POULTRY HYDROLYZED BOTH ESTER AND AMIDE GROUPINGS AND FORMED ... CMPD THAT WERE EXCRETED VIA URINE OF SHEEP OR URINE & FECES OF POULTRY. ONE COMPD FROM SHEEP URINE WAS BELIEVED TO BE 4-T-BUTYL-2-CHLOROPHENYL DIHYDROGEN PHOSPHORIC ACID.

THE PRINCIPAL METABOLITE ISOLATED FROM INSECTS IS BELIEVED TO BE 4-TERT-BUTYL-2-CHLOROPHENYL DIHYDROGEN PHOSPHATE.

AFTER ORAL ADMIN TO SHEEP ... /OF/ (32)P RUELENE ... THE ULTIMATE BIOTRANSFORMATION PRODUCT OF (32)P RUELENE, INORGANIC PHOSPHATE PRODUCED BY HYDROLYSIS AND DEALKYLATION, ENTERED NORMAL BODY PROCESSES THUS RESULTING IN SOME RETENTION OF (32)P IN THE ANIMALS. IN SHEEP DOSED WITH (32)P RUELENE, (32)P PERSISTED IN THE TISSUES FOR SEVERAL WK, BUT NO (32)P WAS DETECTED AFTER 7 DAYS. THE EXTENT OF BIOTRANSFORMATION ... TO INORGANIC PHOSPHATE WAS INDICATED BY ORAL ADMIN OF (32)P PHOSPHORIC ACID TO ... SHEEP, WHEN 28-40% WAS EXCRETED MAINLY IN THE FECES, WHEREAS 85-95% OF AN ORAL DOSE OF (32)P RUELENE WAS EXCRETED MAINLY IN THE URINE.

METABOLITES IDENTIFIED FROM IN VITRO METABOLISM OF CRUFOMATE IN INTESTINAL SAC PREPN WERE 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORAMIDATE; 2-CHLORO-4(2-HYDROXY-1,1-DIMETHYLETHYL)PHENYL METHYL METHYLPHOSPHORAMIDATE; 2-[3-CHLORO-4-[((METHOXY)METHYLAMINO) PHOSPHINYL]OXY]PHENYL-2-METHYLPROPIONIC ACID; 4-TERT-BUTYL-2-CHLOROPHENOL & ITS GLUCURONIDE & AROMATIC GLUCURONIDE OF 2-CHLORO-4(2-HYDROXY-1,1-DIMETHYLETHYL)PHENOL.

For more Metabolism/Metabolites (Complete) data for RUELENE (7 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5 Einträge

... AFTER SHEEP WERE GIVEN ORAL DOSES ... 85-95% OF DOSE WAS RECOVERED IN EXCRETA. ANALYSES SHOWED THAT THIS COMPD WAS DEGRADED TO INORGANIC PHOSPHATE WHICH WAS SUBSEQUENTLY INCORPORATED IN BONE. ... RUELENE WAS FED TO LAYING HENS AT ... 100 PPM FOR 7 DAYS. SIX METABOLITES WERE ISOLATED FROM EXCRETA. RESIDUES APPEARED IN EGG YOLKS 3-5 DAYS AFTER RETURN TO NORMAL FEED.

ORALLY TREATED SHEEP ELIMINATED 85% OF THE (32)P LABELED RUELENE IN THE URINE IN 24 HR ... THE WHOLE EXTRACT OF WHOLE BLOOD CONTAINED ... /RUELENE AND 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID/ AS WELL AS TRACES OF 3 MORE POLAR METABOLITES OF UNKNOWN STRUCTURE. RUELENE IS RAPIDLY DEGRADED IN POULTRY ... TO PHOSPHORIC ACID, AND INCORPORATED IN BONE TISSUE. OF THE ORAL DOSE GIVEN IN FEED ONLY 29% WAS EXCRETED AFTER 21 DAYS. AT LEAST SIX METABOLITES WERE ISOLATED IN EXCRETA ... THOSE ... IDENTIFIED WERE 4-TERT-BUTYL-2-CHLOROPHENYL METHYL PHOSPHORIC ACID AND METHYL PHOSPHORIC ACID.

AFTER ORAL ADMIN TO SHEEP ... (32)P RUELENE WAS READILY ABSORBED AND RAPIDLY EXCRETED MAINLY IN THE 24 HR URINE. 73% OF (32)P WAS EXCRETED IN THE URINE AND 14% IN THE FECES. PEAK BLOOD LEVELS OF (32)P OCCURRED FOUR HR AFTER DOSING. THE ULTIMATE BIOTRANSFORMATION PRODUCT OF (32)P RUELENE, INORGANIC PHOSPHATE PRODUCED BY HYDROLYSIS AND DEALKYLATION, ENTERED NORMAL BODY PROCESSES ... RESULTING IN SOME RETENTION OF (32)P IN ANIMALS. IN SHEEP DOSED WITH RUELENE, (32)P PERSISTED IN TISSUES FOR SEVERAL WEEKS, BUT NO /RUELENE/ WAS DETECTED ... AFTER 7 DAYS.

... WILL PASS INTO MILK OF TREATED ANIMALS.

For more Absorption, Distribution and Excretion (Complete) data for RUELENE (13 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 5 Einträge

Used to kill cattle lice, grubs, and horn flies; [HSDB]

Farming (Pesticides) [Category: Industry]

/SRP: FORMER USE/ INSECTICIDE FOR CATTLE GRUBS, HORN FLIES & LICE ON CATTLE

Medication (vet): Anthelmintic; insecticide

Animal systemic insecticide used for cattle grub control.

Consumption Patterns100% AS AN INSECTICIDE FOR CATTLE GRUBS, HORN FLIES, & LICE ON BEEF CATTLE & NON-LACTATING DAIRY CATTLE (1973)
Methods of ManufacturingREACTION OF 4-T-BUTYL-2-CHLOROPHENYL PHOSPHONYLDICHLORIDE WITH METHANOL & THEN WITH METHYLAMINE
Formulations/PreparationsREADY TO USE POUR-ON (122 G AI/L); WORMER DRENCH (210 G AI/L); POUR OR SPRAY (250 G AI/L); FOR DIPPING VAT USE (375 G AI/L).
Use ClassificationINSECTICIDES
General Manufacturing Information · 5 Einträge

The WHO Recommended Classification of Pesticides by Hazard identifies Crufomate (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

PRODUCT DISCONTINUED BY THE DOW CHEMICAL CO.

INCOMPATABILITIES: ... IT IS INCOMPATIBLE WITH ALKALINE PESTICIDES ... .

ORALLY EFFECTIVE AGAINST HAEMONCHUS CONTORTUS, OSTERTAGIA SPECIES, & TRICHOSTRONGYLUS SPECIES, BUT RELATIVELY INEFFECTIVE AGAINST MANY IMMATURE FORMS & NEMATODIURUS IN SHEEP. IN CATTLE WARBLE CONTROL THERE IS SEASONAL VARIATIONS IN TOXICITY WHICH APPEARS TO BE ASSOCIATED WITH DEATH & ABSORPTION OF LARVAE RATHER THAN TOXICITY OF INSECTICIDE PER SE. USE DRUG BEFORE LARVAE REACH GULLET & EPIDURAL AREAS. THIS IS SEPTEMBER FOR MOST OF USA, ITALY, BULGARIA, & IRELAND.

CRUFOMATE IS A SYSTEMIC INSECTICIDE & ANTHELMINTIC USED MAINLY FOR THE TREATMENT OF CATTLE AGAINST WARBLE FLIES, ECTOPARASITES & HELMINTHS. IT IS NOT USED IN CROP PROTECTION. ... NONHAZARDOUS TO WILDLIFE.

Anbieter28 Anbieter

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