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Home > Encyclopedia > Binapacryl

Binapacryl

pharmaceutical raw materials
Binapacryl structure

Binapacryl 

structure
  • CAS No:

    485-31-4

  • Formula:

    C15H18N2O6

  • Chemical Name:

    Binapacryl

  • Synonyms:

    2-Butenoic acid,3-methyl-,2-(1-methylpropyl)-4,6-dinitrophenyl ester;Crotonic acid,3-methyl-,2-sec-butyl-4,6-dinitrophenyl ester;HOE 2784;NIA 9044;Acricid;Binapacryl;2-sec-Butyl-4,6-dinitrophenyl 3-methyl-2-butenoate;2-(1-Methylpropyl)-4,6-dinitrophenyl β,β-dimethacrylate;Morocide;Niagara 9044;2-sec-Butyl-4,6-dinitrophenyl 3-methylcrotonate;Endosan;Dinapacryl;1135443-30-9

  • Categories:

    Agrochemicals  >  Insecticides

Description

Generic name for 2-sec-butyl-4,6- dinitrophenyl-3-methyl-2-butenoate. C1 5 H8O 6 N2.


COLOURLESS CRYSTALLINE POWDER.


2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate is an enoate ester obtained by formal condensation of the carboxy group of 3,3-dimethylacrylic acid with the phenolic hydroxy group of dinoseb. It is a C-nitro compound and an enoate ester. It derives from a dinoseb.

Binapacryl Basic Attributes

322.31

322.31

207-612-9

0835

2779

DTXSID9040269

COLORLESS CRYSTALLINE POWDER|Pale yellow to brownish crystals

Characteristics

118

4.75 (est)

COLOURLESS CRYSTALLINE POWDER.

1.2307 g/cm3 @ Temp: 20 °C

66-67 °C

436.7±45.0 °C at 760 mmHg

171.7±30.7 °C

1.553

Solubility in water: none

0-6°C

Vapour pressure, Pa at 60°C: 0.013

Oral-Rat  LD50: 58 mg/kg; Oral-Mouse LD50: 1600 mg/kg

Combustion produces toxic nitrogen oxide gas

Faint aromatic odor

VAPOR PRESSURE: 1X10-4 MM HG @ 60 °C

Safety Information

III

6.1(b)

2779

3

61-21/22-50/53

53-45-60-61

GQ5600000

T,N

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

Unstable in alkali & concentrated acids, suffers slight hydrolysis on long contact with water & is slowly decomposed by ultra violet light.

P201-P273-P280-P308 + P313-P501

H302 + H312-H360D-H410

Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|The disposal of large quantities of binapacryl requires the use of an incinerator with an afterburner. Recommendable method: Incineration. Not recommendable method: Hydrolysis. Peer-review: Acid and alkaline hydrolysis yield dinitrophenol. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/|Group III Containers (both combustible and non-combustible) that previously held organic mercury, lead, cadmium, arsenic, or inorganic pesticides should be triple rinsed, punctured and disposed of in a sanitary landfill. Non-rinsed containers should be encapsulated and buried at a specially designated landfill site. /Organic mercury, lead, cadmium, arsenic, or inorganic pesticides/

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P308+P313, P312, P322, P330, P363, P391, P405, and P501|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P302+P352, P312, P321, P322, P330, P361, P363, P405, and P501

Use water spray, powder, foam, carbon dioxide.

... BURNS AT TEMP ABOVE 150 °C.

Avoid skin and eye contact, and inhalation of the dust and spray mist.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

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. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Keep in a well-ventilated room.

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 may cause effects on the metabolism. This may result in high body temperature and sweating. The effects may be delayed. Medical observation is indicated.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

Toxicity

highly toxic

LD50 Rat, female oral 58 mg/kg|LD50 Rat male oral 63 mg/kg|LD50 Mouse oral 1600 mg/kg|LD50 Guinea pig oral 300 mg/kg|LD50 Rabbit dermal 750 mg/kg in acetone.

Binapacryl is an anthropogenic compound and it is not known to exist in nature. (SRC)

Binapacryl has been used as a fungicide and a miticide for the control of spider mites in pome fruit or nut and hop cultivation, and in the control of powdery mildews in fruit cultivations(1). It may be released to the environment as a fugitive emission during its production and during its application as a pesticide(SRC).

TERRESTRIAL FATE: If released to soil, binapacryl may undergo slow hydrolysis in basic soils(1,2). A calculated soil adsorption coefficient of 2400(3,SRC), based on an estimated log octanol/water partition coefficient(4) indicates that binapacryl is expected to be essentially immobile in soil(5). A laboratory study has also shown that binapacryl displays limited mobility in soil(6). Binapacryl is known to slowly decompose under the influence of UV light(7) and it may undergo photolysis on sunlit soil surfaces(SRC). Binapacryl is not expected to significantly volatilize from either dry or moist soils(1,8,SRC).|AQUATIC FATE: If released to water, binapacryl is expected to undergo slow hydrolysis under basic conditions(1). A calculated bioconcentration factor of 2400(2,SRC), based on an estimated log octanol/water partition coefficient(3,SRC), indicates that this compound may significantly bioconcentrate in fish and aquatic organisms(SRC). Based on an estimated Henry's Law constant of 3.37x10E-7 atm/cu-m mol at 25 °C(2,SRC), binapacryl is not expected to significantly volatilize from water to the atmosphere(SRC). Binapacryl may under photolysis in aquatic systems(4,SRC).|ATMOSPHERIC FATE: Binapacryl is known to slowly decompose under the influence of UV light(1) and it may undergo photolysis in the atmosphere. An estimated rate constant for the gas-phase reaction of binapacryl with photochemically produced hydroxyl radicals leads to an estimated half-life of 4.63 hours in the ambient atmosphere(2,SRC). An estimated half-life of 3.72 hrs can be calculated for the gas-phase reaction with ozone(2,SRC); however, the rate of these latter two atmospheric processes may be greatly attenuated as binapacryl is expected to exist predominately adsorbed particulates in the atmosphere(SRC).

Binapacryl is described as undergoing hydrolysis in dilute basic solutions(1) indicating it has the potential to hydrolyze under alkaline environmental conditions. Binapacryl has been described as amenable to hydrolytic transformations in soil(2); the hydrolysis product is dinoseb. During experiments designed to determine the mobility of binapacryl in soil, it was found to undergo significant hydrolysis(3). Binapacryl is known to slowly decompose under the influence of UV light(4) and it may undergo photolysis on sunlit soil surfaces in water, or in the atmosphere(SRC). An estimated rate constant for the gas-phase reaction of binapacryl with photochemically produced hydroxyl radicals of 8.32x10E-11 cu-cm/molec-sec translates to a half-life of 4.63 hours using an average hydroxyl radical concentration of 5x10E-5 molec/cu-cm(4,SRC). An estimated rate constant for the gas-phase reaction of binapacryl with ozone of 7.39X10E-17 cu-cm/molec-sec translates to a half-life of 3.72 hrs using an average ozone concentration of 7X10E-11 mole/cu-cm(4,SRC). However, the rate of these gas-phase atmospheric processes may be greatly attenuated as binapacryl is expected to exist predominately as a particulate in the ambient atmosphere(SRC).

Based on an estimated log octanol/water partition coefficient of 4.75(1,SRC), a calculated bioconcentration factor of 2400 can be calculated for binapacryl using an appropriate regression equation(2,SRC). The magnitude of this value indicates that binapacryl may significantly bioconcentrate in fish and aquatic organisms(SRC).

Based on an estimated log octanol/water partition coefficient of 4.75(1,SRC), a calculated soil adsorption coefficient of 9100 can be calculated for binapacryl using an appropriate regression equation(2,SRC). This value indicates that binapacryl will be essentially immobile in soil(3). The movement of binapacryl through a silty clay loam was investigated by TLC experiments in which it was found to have an Rf of 0.03, indicating very limited mobility(4).

Based on a calculated Henry's Law constant of 3.37x10E-7 atm/cu-m mol at 25 °C(1,SRC), and its vapor pressure, 3.16x10E-7 mm Hg at 20 °C(2), binapacryl is not expected to significantly volatilize from either moist or dry soil(SRC). Based on the Henry's Law constant, the estimated half-life for the volatilization of binapacryl from a model river 1 m deep, flowing at 1 m/sec, with a wind speed of 3 m/sec is approx 63 yrs(3,SRC), indicating that it will be too slow to be environmentally significant.

The probable routes of exposure to binapacryl are by dermal contact or inhalation of binapacryl dust during its production, formulation, or use as a pesticide. (SRC)|Workers involved with the application of binapacryl to fruit orchards via airblast spraying were found to receive dermal exposure of 29.6 mg/hr and respiratory exposure of 0.07 mg/hr(1).

Drug Information

BINAPACRYL WAS ABSORBED POORLY, IF AT ALL, THROUGH SKIN OF MICE AND RABBITS.|After a single administration of binapacryl, both rats and rabbits excreted 7-17% in the urine within 48 hr. As late as the tenth day, 0.12% of the dose was detected in the urine of rats ... .

WHEN ADMINISTERED ORALLY TO GUINEA PIGS, THIS COMPOUND GIVES RISE TO ... /2-SEC-BUTYL-4,6-DINITROPHENOL/ IN BLOOD.|Following oral doses of binapacryl, the urine of both rabbits and rats contained oxidation products of the butyl side chain of dinoseb, including the acid. In addition, rat urine contained traces of free 6-aminophenol and the urine of rabbits contained a substantial amount of this compound and its glucuronide.

BASIC MECHANISM OF TOXICITY IS STIMULATION OF OXIDATIVE METABOLISM IN CELL MITOCHONDRIA, BY INTERFERENCE WITH NORMAL COUPLING OF CARBOHYDRATE OXIDN TO PHOSPHORYLATION (ADP TO ATP). INCR OXIDATIVE METABOLISM LEADS TO PYREXIA, TACHYCARDIA, & DEHYDRATION, & ULTIMATELY DEPLETES CARBOHYDRATE & FAT STORES. /NITROPHENOLIC COMPOUNDS/

Fresh air, rest. Artificial respiration may be needed. 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.

1) WASH CONTAMINATED SKIN & HAIR PROMPTLY WITH SOAP & WATER, OR WITH WATER ALONE IF SOAP IS NOT AVAILABLE. 2) FLUSH CHEMICAL FROM EYES WITH COPIOUS AMT OF CLEAN WATER. 3) IN...SYSTEMIC POISONING: A) REDUCE ELEVATED BODY TEMP BY PHYSICAL MEANS. ADMIN SPONGE BATHS & COVER VICTIM WITH LOW-TEMP BLANKETS. IN FULLY CONSCIOUS PATIENT, ADMIN COLD, SUGAR-CONTAINING LIQ BY MOUTH AS TOLERATED. B) ADMIN OXYGEN CONTINUOUSLY BY MASK TO MINIMIZE TISSUE ANOXIA. C) UNLESS THERE ARE MANIFESTATIONS OF CEREBRAL EDEMA, ADMIN IV FLUIDS AT MAX TOLERATED RATES TO ENHANCE URINARY EXCRETION OF TOXICANT & TO SUPPORT PHYSIOLOGIC MECHANISMS FOR HEAT LOSS. IN THE PRESENCE OF CEREBRAL EDEMA, IV FLUIDS MUST BE ADMIN VERY CAUTIOUSLY TO AVOID INCR THE CEREBRAL INJURY. /NITROPHENOLIC HERBICIDES/|3D) ALTHOUGH NOT PREVIOUSLY USED IN THIS TYPE OF POISONING, DIAZEPAM (VALIUM) SHOULD HELP: ADULT DOSE, 5-10 MG SLOWLY IV, OR IM (DEEP); CHILD'S DOSE, 0.1 MG/KG. REPEAT EVERY 2-4 HR AS NEEDED. AMOBARBITAL OR PENTOBARBITAL MAY BE NEEDED. DOSE IN ADULTS: 200 MG, IM OR SLOWLY IV, EVERY 4-6 HR; CHILD'S DOSE: UP TO 5 MG/KG. CAUTION: BE PREPARED TO COUNTERACT RESP DEPRESSION & HYPOTENSION WHICH MAY FOLLOW...ANTICONVULSANTS & SEDATIVES. /NITROPHENOLIC HERBICIDES/|4) IF TOXICANT ... INGESTED, EVACUATE STOMACH & INTESTINE. A) IF VICTIM IS ALERT & RESP IS NOT DEPRESSED, GIVE SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER, TO INDUCE VOMITING (ADULTS 12 YR & OLDER: 30 ML; CHILDREN UNDER 12: 15 ML). CAUTION: OBSERVE VICTIM CLOSELY AFTER ADMIN IPECAC. IF CONSCIOUSNESS LEVEL DECLINES, OR IF VOMITING HAS NOT OCCURRED IN 15 MIN, IMMEDIATELY INTUBATE, ASPIRATE, & LAVAGE THE STOMACH /SRP: TAP WATER IN CHILDREN, SALINE IN ADULTS/. FOLLOWING EMESIS, HAVE VICTIM DRINK A SUSPENSION OF /SRP: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/...TO BIND TOXICANT REMAINING IN GI TRACT. /NITROPHENOLIC HERBICIDES/|4B) IF VICTIM IS NOT FULLY ALERT, EMPTY STOMACH IMMEDIATELY BY INTUBATION, ASPIRATION, & LAVAGE, USING /SRP: TAP WATER (CHILDREN), ISOTONIC SALINE (ADULT)/ ... BECAUSE THESE PESTICIDES ARE USUALLY DISSOLVED IN PETROLEUM DISTILLATES, EMESIS & INTUBATION ... INVOLVE ... RISK THAT SOLVENT WILL BE ASPIRATED ... FOR THIS REASON: 1) IF VICTIM IS UNCONSCIOUS OR OBTUNDED & FACILITIES ARE AT HAND, INSERT ENDOTRACHEAL TUBE (CUFFED, IF AVAILABLE) PRIOR TO GASTRIC INTUBATION. 2) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH & TURNED TO THE LEFT, DURING INTUBATION & LAVAGE (TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD). 3) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. 4) AFTER ASPIRATION OF GASTRIC CONTENTS & WASHING OF STOMACH, INSTILL /SRP: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/ ... THROUGH STOMACH TUBE TO LIMIT ABSORPTION OF REMAINING TOXICANT. DO NOT INSTILL CREAM, MILK, OR OTHER ... VEGETABLE OR ANIMAL FATS ... LIKELY TO ENHANCE ABSORPTION. /NITROPHENOLIC HERBICIDES/|For more Antidote and Emergency Treatment (Complete) data for BINAPACRYL (6 total), please visit the HSDB record page.

ALL PESTICIDES OF THIS TYPE ACT BY INCREASING OXIDATIVE METAB AND HEAT PRODUCTION, THUS RESEMBLING DINITROPHENOL ... .|... Two workers developed headache, nausea, vomiting, abdominal pain, diarrhea, & breathing difficulties after spraying tomatoes with binapacryl for 2 hr. Fever, weak pulse, and tremor were noted later. ... Recovery was complete within a week.|Symptomatology: 1. Marked fatigue, tremendous thirst, profuse sweating, flushing of face. 2. Nausea, vomiting, abdominal pain, & occasionally diarrhea. 3. Restlessness, anxiety, excitement, occasionally leading to convulsions. 4. A rise in body temp, which is roughly proportional to the toxic dose, may culminate in severe hyperpyrexia ... 5. Tachycardia, hyperpnea, dyspnea, cyanosis, & sometimes muscle cramps. 6. Loss of consciousness, cessation of breathing, & death. 7. Late complications: A. Decreased urine output with albuminuria, casts, pigment, & sometimes blood cells, due to toxic nephritis. B. Jaundice & tenderness in liver region due to toxic hepatitis. 8. Occasional hypersensitivity reactions after repeated exposures (or in chronic poisoning) include agranulocytic angina, skin rashes, peripheral, ... /SRP: neuropathy/ & late cataract formation. /2,4-Dinitrophenol/|Toxic by ingestion and inhalation.

binapacrile

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

Abdominal pain. Diarrhoea. Headache. Sweating. Nausea. Shortness of breath. Vomiting. Weakness.


MAY BE ABSORBED! See Inhalation.


Redness.

Binapacryl Use and Manufacturing

Methods of Manufacturing

/IT IS/ MADE BY ESTERIFICATION OF DINOSEB ... WITH 3-METHYLCROTONOYL CHLORIDE ... .

Uses

Fungicide, miticide.

MOROCIDE 25 WETTABLE POWDER; MOROCIDE 50 WETTABLE POWDER; MOROCIDE 40 EMULSIFIABLE CONCENTRATE; MOROCIDE 4 DUST; AND COMBINATIONS WITH OTHER PESTICIDES.|AVAILABLE IN DUST FORMULATION CONTAINING 4% (ACTIVE INGREDIENT) WITH 4% (ACTIVE INGREDIENT) OF THIODAN & AS LIQUID FORMULATION WITH TETRADIFON. /FORMER USE/|Technical grade (purity greater than or equal to 97%) ... emusifiable concentrate (384 g ai/l); dispersion (500 g/l).

The WHO Recommended Classification of Pesticides by Hazard identifies Binapacryl (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide. The international trade of ... Binapacryl ... is regulated by the Rotterdam convention on Prior Informed Consent (see http://www.pic.int/), which entered force on 24 February 2004. According to the PIC Convention, export of /Binapacryl/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).|Incompatible with alkalies. It may be phytotoxic when mixed with some organophosphorus compounds. Binapacryl is a non-systemic acaricide which is effective against powdery mildews, used mainly against all stages of spider mites and powdery mildews of apples, citrus, cotton, pears and top fruit at 25-50 g ai/100 l.|... MCDANIEL MITE ON APPLE HAS DEVELOPED RESISTANCE TO THE DINITRO CMPD, BINAPACRYL, IN WASHINGTON STATE ... . /FORMER USE/|/IT IS/ EFFECTIVE ON CONTACT AND BY GAS PHASE AGAINST ALL STAGES OF SPIDER MITES FROM DIFFERENT SPECIES, SOME BUD MITES ... ON A RANGE OF CROPS. /FORMER USE/|/MOROCIDE IS A/ CONTACT MITICIDE WITH OVICIDAL ACTION ... CONTROLS SEVERAL SPIDER MITE SPECIES ON ... PLUMS, PRUNES, ALMONDS, & WALNUTS. ALSO FOR USE ON NON-BEARING TREES ... OR VINES, OR AS POST-HARVEST APPLICATIONS ON BEARING TREES OR VINES. /FORMER USE/

... BY EXTRACTING WITH HEPTANE, TREATING THE EXTRACT WITH SODIUM ETHOXIDE, STEAM DISTILLING THE DINOSEB SO FORMED & MEASURING ITS ABSORPTION @ 420 NM IN DILUTE SODIUM HYDROXIDE; ALTERNATIVELY THE NITRO GROUPS ARE DETERMINED BY THE TITANIUM TRICHLORIDE METHOD.|NITRO-GROUP DETERMINATION, BACK-TITRATION. ... OR GAS CHROMATOGRAPHIC METHOD AND COLORIMETRIC METHOD.|GENERAL SAMPLE, GAS CHROMATOGRAPHY.|EPA Method 515. Capillary Column Gas Chromatography with electron capture detection for the determination of chlorinated herbicides in drinking water. For Dinoseb the estimated detection limit is 0.01 ug/l, and the method detection limit is 0.07 ug/l. Using a packed column, the mean recovery is 86% with a standard deviation of 4% at a spike level of 0.5 ug/l in drinking water. Using a capillary column, the mean recovery is 56% with a Standard deviation of 19% at a spike level of 4.12 ug/l. /Dinoseb/

ACARICIDES

Computed Properties

Molecular Weight:322.31
XLogP3:4.6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:322.11648630
Monoisotopic Mass:322.11648630
Topological Polar Surface Area:118
Heavy Atom Count:23
Complexity:489
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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