ChemicalBook--->CAS DataBase List--->25057-89-0

25057-89-0

25057-89-0 Structure

25057-89-0 Structure
IdentificationBack Directory
[Name]

Bentazone
[CAS]

25057-89-0
[Synonyms]

laddok
leader
Adagio
GALAXY
Thianon
bas3510
BAS 3510
bas 351h
BASAGRAN
herbatox
bas3510h
bas3512h
bas3517h
BENTASON
BENTAZON
BasaMais
Bazargan
BENTAZONE
Pentazone
BAS 3510H
BAS 3512H
BAS 3517H
bas351-07h
basagrankv
Bendioxide
BASF 3510H
BENTAZONTP
basagran 4e
BASAGRAN(R)
BAS 351-07H
Basagran 480
Thiadiazinol
basagran-plus
graminon-plus
Basagran (BASF)
bentazon solution
Bentazone solution
Bentazone Standard
BENTAZON, 250MG, NEAT
Bentazone,aqueous(25%)
Bentazon, Herbicide Mix
BENTAZON PESTANAL, 250 MG
bentazone (bsi, iso,jmaf)
Acetochlor+Metribuzin,W.P.
bentazon (ansi,wssa,canada)
Bentazon 250mg [25057-89-0]
BENTAZON METHYL DERIVATIVE, 50MG, NEAT
3-Isopropyl-2,1,3-benzothiadiazinon-(4)-2,2-dioxid
3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-ol
3-Isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
3-isopropyl-1h-benzo-2,1,3-thiadiazin-4-one-2,2-dioxide
3-benzothiadiazin-4(3h)-one-2,2-dioxide,3-isopropyl-1h-1
3-isopropyl-1h-2,1,3-benzothiaiazin-4(3h)-one-2,2-dioxide
3-isopropyl-2,1,3-benzothiadiazinon-(4)-2,2-dioxid[german]
3-isopropyl-1h-2,1,3-benzothiadiazin-4(3h)-one-2,2-dioxide
2,2-Dioxo-3-propan-2-yl-1H-benzo[d][1,2,6]thiadiazin-4-one
2-ISO-PROPYL-(1H)-BENZO-2,1,3-THIADIAZIN 4-ONE-2,2-DIOXIDE
1h-2,1,3-benzothiadiazin-4(3h)-one,3-isopropyl-,2,2-dioxide
1H-2,1,3-Benzothiadiazin-4(3H)-one, 3-isopropyl-, 2,2-dioxide
3-(1-Methylethyl)-2,1,3-benzothiadiazin-4(3H)-one 2,2-Dioxide
3-(1-METHYLETHYL)-1H-2,1,3-BENZOTHIADIAZIN-4(3H)-ONE,2-DIOXIDE
3-(1-methylethyl)-1h-2,1,3-benzothiazain-4(3h)-one,2,2-dioxide
3-(1-Methylethyl)-1H-2,1,3-benzothiazain-4(3H)-one, 2,2-dioxide
3-(1-METHYLETHYL)-1H-2,1,3-BENZOTHIADIAZIN-4(3H)-ONE-2,2-DIOXIDE
1H-2,1,3-Benzothiadiazin-4(3H)-one,3-(1-methylethyl)-,2,2-dioxide
3,4-Dihydro-3-isopropyl-1H-2,1,3-benzothiadiazin-4-one 2,2-Dioxide
1H-2,1,3-Benzothiadiazin-4(3H)-one, 3-(1-methylethyl)-, 2,2-dioxide
3-Isopropyl-3,4-dihydro-2,1,3-benzothiadiazin-4(1H)-one 2,2-dioxide
bentazone (ISO) 3-isopropyl-2,1,3-benzothiadiazine-4-one-2,2-dioxide
3-Isopropyl-(1H)-benzo-2,1,3-thiadiazin-4-one-2,2-dioxide,aqueous(25%)
[EINECS(EC#)]

246-585-8
[Molecular Formula]

C10H12N2O3S
[MDL Number]

MFCD00078640
[MOL File]

25057-89-0.mol
[Molecular Weight]

240.28
Chemical PropertiesBack Directory
[Appearance]

Bentazon is a colorless to white crystalline powder.
[Melting point ]

137-139°C
[Boiling point ]

395.7±25.0 °C(Predicted)
[density ]

1.3387 (rough estimate)
[refractive index ]

1.5650 (estimate)
[Fp ]

2 °C
[storage temp. ]

APPROX 4°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

pKa (24°): 3.3
[color ]

White
[Water Solubility ]

0.5g/L(20 ºC)
[Merck ]

13,1051
[BRN ]

530220
[Henry's Law Constant]

4.5×103 mol/(m3Pa) at 25℃, HSDB (2015)
[Major Application]

agriculture
environmental
[InChI]

1S/C10H12N2O3S/c1-7(2)12-10(13)8-5-3-4-6-9(8)11-16(12,14)15/h3-7,11H,1-2H3
[InChIKey]

ZOMSMJKLGFBRBS-UHFFFAOYSA-N
[SMILES]

CC(C)N1C(=O)c2ccccc2NS1(=O)=O
[NIST Chemistry Reference]

Bentazone(25057-89-0)
[EPA Substance Registry System]

Bentazon (25057-89-0)
Hazard InformationBack Directory
[Uses]

Herbicide.
[Definition]

ChEBI: A benzothiadiazine that is 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide substituted by an isopropyl group at position 3.
[Potential Exposure]

A potential danger to those involved in the manufacture, formulation or application of this selective postemergent thiadiazine herbicide.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.
[Incompatibilities]

Keep away from flammable materials, heat and flame. Risk of fire and explosion if formulations contain flammable/explosive solvents.
[Description]

Bentazon is unique under these herbicides because it is the only compound that bears a sulfonyl group. A puzzle that is not solved yet is that bentazone is an excellent herbicide but has a very low pI50-value.
[Chemical Properties]

Bentazon is a colorless to white crystalline powder.
[Waste Disposal]

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
[Production Methods]

Bentazone is synthesised through a multi-step chemical process that begins with the preparation of isopropylaminosulfonyl chloride, formed by reacting isopropylamine hydrochloride with sulfonyl chloride in acetonitrile under reflux. Separately, O-aminobenzoic acid methyl ester is prepared from phthalic anhydride via a series of reactions involving aqueous ammonia, sodium hydroxide, and methanol. These two intermediates are then combined: isopropylaminosulfonyl chloride is reacted with methyl anthranilate in toluene, using ammonia or an organic base to form N-isopropylamine sulfonylmethyl anthranilate. The pH is carefully controlled and the mixture is cooled to improve product quality. Finally, cyclisation is carried out in sodium methoxide solution at 60–65 DegC for 30 minutes, followed by acidification to yield bentazone.
[Agricultural Uses]

Selective post-emergent herbicide: A post-emergence herbicide used to control broadleaf weeds in crops such as beans, corn, mint, soybeans, rice, and peanuts. All products formerly marketed in the U.S. contain the sodium salt of bentazon as the active ingredient, referred to as sodium bentazon. Also used in selective post-emergent control of broadlelaf weeds and sedges in alfalfa, asparagus, cereals, clover, digitalis, dry peas, flax, garlic, grasses, green lima beans, mint, onions, potatoes, snap beans for seed, sorghum, soybeans and sugarcane. Not currently registered in the U.S. It is reported to be used in most European countries.
[Trade name]

ASAGIO®; BAS 351-H®; BASAGRAN®; BENDIOXIDE®; BENTA®; BLAST®; ENTRY®; LADDOK®; LEADER®; PLEDGE®; STORM®
[Mechanism of action]

Selective action, absorbed by foliage with very little translocation. Inhibits photosynthesis (photosystem II).
[Environmental Fate]

Soil. Under aerobic conditions, bentazone was reported to degrade to 6- and 8-hydrox ybentazone compounds. In addition, anthranilic acid and isopropylamide were reported as soil hydrolysis products (Otto et al., 1978). Persistence in soil is less than 6 weeks (Hartley and Kidd, 1987). Bentazone is readily adsorbed onto organic carbon and therefore, is not expected to leach to groundwater (Abernathy and Wax, 1973). The dissipation half life of bentazone in field soil is 5 days (Ross et al., 1989).
Plant. Undergoes hydroxylation of the aromatic ring and subsequent conju-gation in plants (Otto et al., 1978; Hartley and Kidd, 1987) forming 6- and 8-hydroxybentazone compounds (Otto et al., 1978). The half-life in and/or on plants is 2–3 days (
Photolytic. Humburg et al. (1989) reported that 30% degradation of bentazone on glass plates occurred when exposed to UV light (λ = 200–400 nm); however, no photoproduct(s) were reported. The natural sunlight and simulated sunlight irradiation of
Chiron et al. (1995) investigated the photodegradation of bentazone (20 μg/L) in distilled water and Ebro River water using an xenon arc irradiation. In distilled water, bentazone completely disappeared after 16 hours of irradiation. Photodegradation appeared to follow pseudo-first-order kinetics with a half-life of about 2.5 hours. The presence of humic substances (4 mg/L) increased the rate of photodegradation and the disappearance of bentazone was achieved in 8 hours. No significant breakdown photoproducts were identified.
[Metabolic pathway]

14C-Bentazon degrades in soils under conventional tillage and no-tillage (3-18 years) with varying histories of bentazon application. The half-life for bentazon degradation ranges from 4.6 to 49.5 days; half-lives for some no-tillage soils with the longest histories of application are lower than those of conventional tillage soils. Half-lives for soils with no bentazon history are 3-11 times higher than the half- lives of those previously exposed to bentazon. N- Methylbentazon is the most consistently observed metabolite. The other metabolites identified in soils result from hydroxylation on the phenyl ring and the cleavage of the benzothiadiazine ring, yielding 6- and 8-hydroxybentazons and anthranilic acid via 2-amino-N-isopropylbenzamide.
[storage]

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Store in tightly closed containers in a cool, well-ventilated area away from flammablematerials, sources of heat and fire.
[Pesticide Type]

Herbicide
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H317-H319-H412
[Precautionary statements ]

P261-P273-P280-P301+P312-P302+P352-P305+P351+P338
[Hazard Codes ]

Xn,F
[Risk Statements ]

22-36-43-52/53-20/21/22-11
[Safety Statements ]

2-24-37-61-36-26-16
[RIDADR ]

UN 1648 3/PG 2
[WGK Germany ]

2
[RTECS ]

DK9900000
[TSCA ]

TSCA listed
[HS Code ]

29349990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Eye Irrit. 2
Repr. 2
Skin Sens. 1
[Safety Profile]

Moderately toxic by ingestion and skin contact. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of SO, and NOx.
[Hazardous Substances Data]

25057-89-0(Hazardous Substances Data)
[Toxicity]

LD50 in male, female rats (mg/kg): 383.2, 433.6 orally (Ugazio)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium Methoxide-->Chlorosulfonic acid-->Sodium hypochlorite-->Phthalic anhydride-->Sulfuryl chloride-->Isopropylamine-->Methyl anthranilate-->Sodium benzoate-->Tributylamine-->Phthalamic acid-->Isopropylamine hydrochloride-->Ethyl anthranilate
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Bentazone(25057-89-0).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Bentazone(25057-89-0)MS
Bentazone(25057-89-0)1HNMR
Bentazone(25057-89-0)13CNMR
Bentazone(25057-89-0)IR1
Bentazone(25057-89-0)IR2
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