Related Searches: Acetylphosphoramidothioic

Acetylphosphoramidothioic(CAS No. 30560-19-1)

Acetylphosphoramidothioic C4H10NO3PS (cas 30560-19-1) Molecular Structure

30560-19-1 Structure

Identification and Related Records

【Name】
Acetylphosphoramidothioic
【CAS Registry number】
30560-19-1
【Synonyms】
75 SP
Ortran
RE 12420
Acephat [German]
Phosphoramidothioic acid, acetyl-, O,S-dimethyl ester
Payload
Ortril
Acetamidophos
Acephate [ANSI:BSI:ISO]
Chevron RE 12,420
Phosphoramidothioic acid,acetyl-,O,S-dimethyl ester
Chevron Orthene
Acephate, technical
EPA Pesticide Chemical Code 103301
O,S-Dimethylacetylphosphoroamidothioate
ENT 27822
N-(methoxy-methylsulfanyl-phosphoryl)acetamide
Acephat [German] 95%TC 75%SP
【EINECS(EC#)】
250-241-2
【Molecular Formula】
C4H10NO3PS (Products with the same molecular formula)
【Molecular Weight】
183.166
【Inchi】
InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)
【InChIKey】
YASYVMFAVPKPKE-UHFFFAOYSA-N
【Canonical SMILES】
CC(=O)NP(=O)(OC)SC
【MOL File】
30560-19-1.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.35
【Melting Point】
93℃
【Boiling Point】
2 °C
【Refractive Index】
1.475
【Flash Point】
2?°C
【Water】
readily soluble
【Solubilities】
Very soluble (slightly soluble in acetone and alcohol)
【Color/Form】
Colorless crystals
Colorless to white solid
【Stability】
Relatively
【Storage temp】
APPROX 4°C
【Computed Properties】
Molecular Weight:183.165861 [g/mol]
Molecular Formula:C4H10NO3PS
XLogP3:-0.8
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:3
Tautomer Count:3
Exact Mass:183.0119
MonoIsotopic Mass:183.0119
Topological Polar Surface Area:80.7
Heavy Atom Count:10
Formal Charge:0
Complexity:172
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:128

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
S2;S36
【HazardClass】
6.1
【Safety】

when exposure to acephate,it will have a slight irritation to eyes and skin.
Hazard Codes:? Xn,F
Acephate's Risk Statements:
22:Harmful if swallowed?
36:Irritating to the eyes?
20/21/22:? Harmful by inhalation, in contact with skin and if swallowed
Acephate's Safety Statements:
2:Keep out of the reach of children?
36:Wear suitable protective clothing?
36/37:Wear suitable protective clothing and gloves?
16:? Keep away from sources of ignition - No smoking?
RIDADR? UN1648 3/PG 2

【PackingGroup 】
I; II; III
【Skin, Eye, and Respiratory Irritations】
Organophosphorus cmpd can produce dermal irritation but most are weak sensitizers. /Organophosphorus cmpd/
【Cleanup Methods】
Environmental considerations- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid and solid, NOS/
Environmental considerations- water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid and solid, NOS/
Environmental considerations- air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid and solid, NOS/
【Transport】
50kgs
【Fire Fighting Procedures】
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/
If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/
【Formulations/Preparations】
BONIDE SYSTEMIC INSECTICIDE GRANULES Active Ingredient 1.5% Acephate
DEXOL SYSTEMIC PLANT CARE Active Ingredient 1.5% Acephate
MULTITUDE 75WSP INSECTICIDE Active Ingredient 75.0% Acephate
ORTHENE SYSTEMIC ROSE & FLOWER CARE and ORTHENE GRANUALS Active Ingredient 1.5 % Acephate
ORTHENE SYSTEMIC INSECT CONTROL Active Ingredient 9.40% Acephate
ORTHO SYSTEMIC ROSE & FLORAL SPRAY Active Ingredient 0.1% Resmethrin, 0.25% Acephate, 0.10% Triforine
ISOTOX INSECT KILLER FORMULA IV active ingredient 8.0% Acephate, 0.50% Fenbutatin-oxide
ORTHO ORTHENE FIRE ANT KILLER FORMULA II Active Ingredient 50.0% Acephate
WHITMIRE MICRO-GEN PT 1320 TR Active Ingredient 12.0% Acephate
WHITMIRE TC 136 Active Ingredient 1.5% Acephate,1.0% Fenpropathrin
BORER-STOP ECOTAB Active Ingredient 97% Acephate
ACE-JET Active Ingredient 97.4% Acephate
PRECISE ACEPHATE Active Ingredient 4.0% Acephate
LANCER TECHNICAL Active Ingredient 98.3% Acephate
CHEMINOVA ACEPHATE 90SP Active Ingredient 90% Acephate
Soluble powder, granules.
Technical product (80-90% pure)
25% soluble powder, 75% suspension, 0.25-1% pressurized sprays; various granular formulations.
Wettable powder, soluble powder, soluble extruded pellets, granular, and liquid formulations
Technical grade is 97% pure
【Other Preventative Measures】
... NOTES TO PHYSICIAN: This material contains a cholinesterase inhibitor. Measurement of blood cholinesterase activity may be useful in monitoring exposure. If signs and/or symptoms of cholinesterase inhibition appear, atropine sulfate is antidotal. ... PROTOPAM is also antidotal and may be used in conjunction with atropine but should not be used alone. /Orthene Fire Ant Killer 1 (50% acephate)/
In order to mitigate occupational risks, the following risk mitigation measures are necessary: Formulate all soluble powder formulations into water soluble bags, except for soluble powders sold for fire ant, harvester ant, or hopper box seed treatment uses. Limit the 1 pound active ingredient per acre (lb ai/A) cotton aerial application rate to cotton grown in California and Arizona; reduce the maximum aerial application rate for cotton to 0.75 ai/A for all other areas of the United States. Delete aerial application to turf. Require enclosed cockpits and mechanical flagging for all aerial applications. Reduce maximum sod farm and golf course turf application rates (non-granular formulations) to 3 lb ai/A and 4 lb ai/A, respectively. Reduce maximum application rates for greenhouse floral and foliage plant crops, and outdoor floral and ground covers to 1 lb ai per 100 gallons water (not to exceed 0.75 lb ai/A for cut flowers and 1.0 lb ai/A for other ornamentals). Delete the application of acephate by low pressure handwand to treat trees, shrubs, and outdoor flora; for the control of wasps; and for perimeter treatment by PCOs. Delete the use of granular formulations to be applied by belly grinder, shaker can, or by hand to trees, shrubs, and 12" pots. Add personal protective equipment to end use product labels for workers who mix and load, and/or apply acephate.
In order to mitigate residential postapplication risk, the following risk mitigation measures are necessary: Delete residential indoor uses. Delete all turfgrass uses (except golf course, sod farm, and spot or mound treatment for ant control). Establish a 3 day pre-harvest interval (PHI) for the harvesting of sod.
Keep out of reach of children. Avoid contact with mouth, skin, and eyes.
In case of damage to, or leaking from containers of this material, contact the Pesticide Safety Team Network at (800) 424-9300. /Organophosphorus pesticide, solid not otherwise specified, (cmpd & prepn) (insecticide, other than agricultural, not elsewhere classified); Organophosphorus pesticide, liq, not otherwise specified (cmpd & prepn) (agricultural insecticides, not elsewhere classified, liq), (insecticides, other than agricultural, not otherwise classified), and (agricultural insecticides, not elsewhere classified, liq); Organophosphorus pesticide, solid, not otherwise specified (cmpd & prepn) (insecticides, other than agricultural, not elsewhere classified); and (agricultural insecticides, not elsewhere classified, other than liq)/
The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed ... each time when it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Organophosphorus pesticides/
In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/
Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/
Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/
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. /Organophosphorus pesticides/
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, flammable, toxic/
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, liquid, NOS/
Personnel protection: Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. /Organophosphorus pesticides, liquid, flammable, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Organophosphorus pesticides, solid, NOS/
【Protective Equipment and Clothing】
Workers handling and applying organophosphate pesticides (opp) must ... be given personal protective equipment comprising overalls made of a tight fabric or polyvinyl chloride, gloves, and rubber boots. They must wear a respirator with an activated-carbon gas filter cartridge affording protection for a determined number of working hours. The eyes should be protected by goggles. The signalmen for aerial dusting operations should be equipped with a hat and cape made of polyvinyl chloride or a fabric impregnated with a water repellent. /Pesticides, organophosphorus/
PERSONAL PROTECTION EYES AND FACE: For application of product in accordance with label instructions, no special eye protection is needed. Handling of the product is not likely to present an eye exposure concern during normal handling. In the event of an accidental discharge of the material during manufacture or handling which could cause eye contact, workers should wear goggles or a face shield. SKIN: Wear protective clothing when handling or applying this product including long pants, long sleeved shirt, socks, shoes, and chemical resistant gloves. RESPIRATORY: No special respiratory protection is normally required. However, if operating conditions create airborne concentrations which exceed the recommended exposure standards, the use of an approved respirator is required. /Orthene Fire Ant Killer 1(50% acephate)/
Personnel protection ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, flammable, toxic/
Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Organophosphorus pesticides, liquid and solid, NOS/
【Octanol/Water Partition Coefficient】
log Kow = -0.85
【Disposal Methods】
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/
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/
SMALL SPILL: Sweep up material and place in disposable container. ... LARGE SPILL: Clean up spills immediately, observing precautions in Exposure Controls/ Personal Protection section. Vacuum with machines equipped with high efficiency filters or sweep up material and place in a disposable container. Scrub contaminated area with detergent and water using a stiff broom. Pick up liquid with Oil Dry, cat litter, clay, rags or other absorbent and place in a disposable container. /Orthene Fire Ant Killer 1 (50% acephate)/
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Produced by acetylation of O,O-dimethyl phosphoroamidothioate followed by isomerization.
Acephate may be produced by the acetylation of O,O-dimethylphosphoroamidothioate, (which is prepared from O,O-dimethylphosphorothioic acid chloride and ammonia).
Preparation and activity: Magee, US 3716600 and US 3845172 (1973, 1974 both to Chevron).
Consumption Patterns

Annual domestic use is approximately 4 to 5 million pounds of active ingredient per year.
2.2 Million lbs US consumption (1982).
【Usage】

Contact and systemic insecticide

【Sampling Procedures】
If phosphorus forms are to be differentiated, filter sample immediately after collection. Preserve by freezing at or below -10 deg C. Add 40 mg mercury chloride/l to the samples. ... Do not add either acid or chloroform as a preservative when phosphorus forms are to be determined. /Phosphorus forms/
NIOSH Method 7905. Analyte: Phosphorus. Matrix: Air. Sampler: Solid sorbent tube (Tenax Gas chromatography, 100 mg/50 mg). Flow Rate: 0.01 to 0.2 l/min: Sample Size: 12 liters. Shipment: Routine. Sample Stability; 94% recovery after 7 days at 25 deg C. /Phosphorus/
NIOSH Method 7300. Analyte: Phosphorus. Matrix: Air. Sampler: Filter (0.8 um cellulose ester membrane) Flow Rate: 1 to 4 l/min: Sample Size: 500 liters. Shipment: Routine. Sample Stability; Stable. /Phosphorus/

Biomedical Effects and Toxicity

【Biological Activity】
Anticholinesterase insecticide that produces cholinotoxicity. Displays weak inhibition of rat acetylcholinesterase (AChE) but potently inhibits cockroach AChE.
【Pharmacological Action】
- Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
【Biomedical Effects and Toxicity】
Within 1 hr, 130 day-old loblolly pine seedlings absorbed and distributed (14)C-orthene from nutrient solution.
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/
The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/
... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/
Many of the organophosphorus insecticides are excreted in the milk. ... /Organophosphorus insecticides/
An investigation was conducted of inhalation and skin acephate exposures in pesticide formulation workers. The cohort consisted of four persons employed at a small Italian pesticide formulation factory. Breathing zone samples were collected over a full 8 hour shift and analyzed for acephate. Gauze pads were attached to the hands, face, and body of two workers to measure skin exposure. Urine samples were collected daily and analyzed for acephate and methamidophos, a major acephate metabolite. Venous blood samples were collected and analyzed for erythrocyte acetylcholinesterase (AChE) and plasma cholinesterase (PChE). Median 8 hour time weighted acephate concentrations ranged from 0.278 to 2.170 mg/m3. Urine acephate concentrations ranged from 1 to 10 milligrams per liter (mg/L), median 0.4 to 1.1mg/L. Methamidophos was not detected in any samples. Median total skin deposition of acephate ranged from 26.1 to 41.9 milligrams per day (mg/day). Assuming that 30 to 50% of the breathing zone exposure and 10 to 20% of the skin dose were absorbed, the median intake of acephate was estimated to be 10 to 20 mg/day. Skin absorption was significantly correlated with urinary excretion of acephate. No significant changes in AChE or PChE activity were noted in subjects whose urinary acephate concentrations averaged 1 to 2mg/L or less. Higher urinary acephate concentrations were associated with a 20% decrease in PChE and an 18% decrease in AChE activity. These decreases were not considered biologically significant. The authors conclude that this investigation does not support the notion that acephate is substantially converted into methamidophos in humans. NOTE: Methamidophos may be RELT [Maroni M et al; Arch Environ Contam Toxicol 19 (5): 782-8 (1990)] PubMed Abstract
... Male Wistar rats ... received by stomach tube a single 270 milligram per kilogram dose of acephate. Blood samples were obtained at 0.5, 8, 24, and 72 hours after dosing and were analyzed for erythrocyte and plasma cholinesterase activity. Rats were then sacrificed and the brains and livers were excised. Brains were homogenized, centrifuged, and the supernatants were analyzed for cholinesterase activity. Livers were cut into small pieces, added to acetonitrile and analyzed for acephate. Acephate was found to be quickly absorbed from the intestines and transported to the liver. This rapid increase was followed by a decline until by the end of 72 hours little or no acephate was found in the liver. Erythrocyte and brain cholinesterases were inhibited by nearly 50 percent and plasma cholinesterase by 18 percent at 0.5 hour after dosing. A recovery then occurred so that after 72 hours enzyme activities were about 85 percent of normal. The authors conclude that, compared to paraoxon, acephate is approximately six orders of magnitude weaker as an inhibitor of cholinesterases.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of acephate with photochemically-produced hydroxyl radicals has been estimated as 1.1 X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 34 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1) Hydrolysis of acephate at 20 deg C was measured in buffered distilled water over a 20 day period(1); the percentage of initial acephate that hydrolyzed ranged from 2.4% at pH 4.0 to 22.1% at pH 8.2 with the hydrolysis rate increasing with increasing pH(2); at 30 deg C, the percentage of initial acephate that hydrolyzed ranged from 4.5% at pH 4.0 to 82.2% at pH 8.2(2). Hydrolysis tests conducted at 37 deg C identified DMPT (O,S-dimethyl phosphorothiolate) as the major hydrolysis product(3); methamidophos and OMPT (O-methylacetyl phosphoramidothiolate) were identified as minor hydrolysis products(3). The direct photolysis of acephate was examined by exposing thin films of the compound to sunlight and ultraviolet light(4); no measurable photodegradation occurred in either sunlight or UV light after 72 hr exposures(4). Acephate, at 8.94 ppm, was photolytically stable in sterile pH 7 phosphate buffer solution that was irradiated for 35 days under natural sunlight(5). In sterile buffer in the presence of a photosensitizer (1% acetone), acephate, at 9.35 ppm, degraded with a dark-control-corrected half-life of 39.6 days in sterile pH 7 aqueous buffer solution that was irradiated for 31 days under natural sunlight(5). Acephate was hydrolytically stable in pH 5 and 7 aqueous buffer solutions, but the hydrolytic half-life was 18 days at pH 9 with O,S-dimethyl phosphorothioate, methamidophos, and O-methyl N-acetylphosphoramidate observed as degradation products(5).

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