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Bentazone

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Name

Bentazone

EINECS 246-585-8
CAS No. 25057-89-0 Density 1.345 g/cm3
PSA 74.86000 LogP 2.36420
Solubility 0.5g/L(20 oC) Melting Point 137-139 °C
Formula C10H12N2O3S Boiling Point 395.7 °C at 760 mmHg
Molecular Weight 240.283 Flash Point 193.1 °C
Transport Information UN 1648 3/PG 2 Appearance powder
Safety 2-24-37-61-36-26-16 Risk Codes 22-36-43-52/53-20/21/22-11
Molecular Structure Molecular Structure of 25057-89-0 (Bentazone) Hazard Symbols HarmfulXn,FlammableF
Synonyms

1H-2,1,3-Benzothiadiazin-4(3H)-one,3-isopropyl-, 2,2-dioxide (8CI);3,4-Dihydro-3-isopropyl-4-oxo-1H-2,1,3-benzothiadiazine2,2-dioxide;3-Isopropyl-1H-2,1,3-benzothiadiazine-4(3H)-one 2,2-dioxide;3-Isopropyl-4-oxo-2,1,3-benzothiadiazine2,2-dioxide;BAS 351-07H;BAS 3510;BAS 3510H;BAS 3512H;BAS 3517H;BAS 351H;Basagran;Basagran 480;Basamais;Bazargan;Bendioxide;Bentazon;Pentazone;Corsar;Leader;Bentazone;;

Article Data 13

Bentazone Synthetic route

109-06-8

α-picoline

30391-89-0

2-amino-N-isopropylbenzamide

25057-89-0

Bentazon

Conditions
ConditionsYield
With chlorosulfonic acid; trichlorophosphate In water; 1,2-dichloro-ethane96.7%
With chlorosulfonic acid; trichlorophosphate In water; 1,2-dichloro-ethane96.8%
With sulfur trioxide; trichlorophosphate In water; 1,2-dichloro-ethane94.1%
86071-21-8

N-isopropyl-N'-o-carbomethoxy-phenyl-sulfamide

25057-89-0

Bentazon

Conditions
ConditionsYield
With sodium methylate In methanol at 40℃; for 2h;
134-20-3

2-carbomethoxyaniline

25057-89-0

Bentazon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / toluene / 1 h / 80 °C
2: MeONa / methanol / 2 h / 40 °C
View Scheme
98-94-2

N,N-dimethyl-cyclohexanamine

30391-89-0

2-amino-N-isopropylbenzamide

25057-89-0

Bentazon

Conditions
ConditionsYield
With sulfur trioxide; trichlorophosphate In 1,2-dichloro-ethane
30391-89-0

2-amino-N-isopropylbenzamide

25057-89-0

Bentazon

Conditions
ConditionsYield
With sulfur trioxide; triethylamine; trichlorophosphate In 1,2-dichloro-ethane
With sulfur trioxide; 2,3-Dimethylaniline; trichlorophosphate In 1,1-dichloroethane
With sulfur trioxide; trichlorophosphate In quinoline; 1,1-dichloroethane
25057-89-0

Bentazon

mecoprop, potassium salt

Conditions
ConditionsYield
In isobutanolic potassium hydroxide97.3%
2928-43-0

2-biphenylmethanol

25057-89-0

Bentazon

1-biphenyl-2-ylmethyl-3-isopropyl-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction;91%
25057-89-0

Bentazon

100-11-8

1-bromomethyl-4-nitro-benzene

132575-80-5

3-Isopropyl-1-(4-nitro-benzyl)-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 0.333333h; Heating;89%
4780-79-4

1-naphthalene methanol

25057-89-0

Bentazon

3-isopropyl-1-naphthalen-1-ylmethyl-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction;88%
586-95-8

pyridine-4-methanol

25057-89-0

Bentazon

3-isopropyl-2,2-dioxo-1-pyridin-4-ylmethyl-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction;86%

Bentazone Chemical Properties

IUPAC Name: 2,2-dioxo-3-propan-2-yl-1H-benzo[c][1,2,6]thiadiazin-4-one 
Empirical Formula: C10H12N2O3S
Molecular Weight: 240.2789g/mol
EINECS: 246-585-8 
Structure of Bentazone (CAS NO.25057-89-0):

Index of Refraction: 1.582
Molar Refractivity: 59.66 cm3
Molar Volume: 178.5 cm3
Polarizability: 23.65×10-24cm3
Surface Tension: 48 dyne/cm
Density: 1.345 g/cm3
Flash Point: 193.1 °C
Enthalpy of Vaporization: 64.59 kJ/mol 
Melting Point: 137-139°C
Boiling Point: 395.7 °C at 760 mmHg
Vapour Pressure: 1.8E-06 mmHg at 25°C 
Product Categories: HERBICIDE;Alphabetic;BA - BH;BA - BHPesticides&Metabolites;A-BAlphabetic;Alpha sort;B;Herbicides;Others;Pesticides&Metabolites 
Canonical SMILES: CC(C)N1C(=O)C2=CC=CC=C2NS1(=O)=O
InChI: 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

Bentazone Uses

 Bentazone (25057-89-0) is a systemic herbicide, be adequate for rice, wheat, corn, sorghum, soybeans, peanuts, peas, alfalfa and other crops and pasture hemlock. It has excellent control efficiency for broad leaved weed and sedge.

Bentazone Production

Isopropylamine hydrochloride reacts with dichloro sulfuryl to gain isopropylamine sulfonyl chloride, then condensation with anthranilic acid methyl ester, and through closed loop to obtain Bentazone (25057-89-0).

Bentazone Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 500mg/kg (500mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 36, 1973.
dog LD50 oral 450mg/kg (450mg/kg)   Pesticide Science. Vol. 3, Pg. 242a, 1972.
duck LD50 oral 15gm/kg (15000mg/kg)   Defense des Vegetaux. Vol. 27, Pg. 78, 1973.
mouse LD50 oral 1130mg/kg (1130mg/kg)   Yakkyoku. Pharmacy. Vol. 37, Pg. 319, 1986.
quail LD50 oral 720mg/kg (720mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 36, 1973.
rabbit LD50 oral 750mg/kg (750mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.
rat LC50 inhalation 5100mg/m3/4H (5100mg/m3)   Pesticide Manual. Vol. 9, Pg. 65, 1991.
rat LD50 oral 1100mg/kg (1100mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 36, 1973.
rat LD50 parenteral 1100mg/kg (1100mg/kg)   Defense des Vegetaux. Vol. 26, Pg. 5, 1972.
rat LD50 skin 2500mg/kg (2500mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.

Bentazone Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Bentazone Safety Profile

Hazard Codes: HarmfulXn,FlammableF
Risk Statements: 22-36-43-52/53-20/21/22-11
R22:Harmful if swallowed. 
R36:Irritating to eyes. 
R43:May cause sensitization by skin contact. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R11:Highly flammable.
Safety Statements: 2-24-37-61-36-26-16
S2:Keep out of the reach of children. 
S24:Avoid contact with skin. 
S37:Wear suitable gloves. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S16:Keep away from sources of ignition.
RIDADR: UN 1648 3/PG 2
RTECS: DK9900000
Hazardous Substances Data 25057-89-0(Hazardous Substances Data)
Moderately toxic by ingestion and skin contact. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of SOx and NOx.

Bentazone Specification

  Bentazone , its cas register number is 25057-89-0. It also can be called 1H-2,1,3-Benzothiadiazin-4(3H)-one, 3-(1-methylethyl)-, 2,2-dioxide (9CI) ; 1H-2,1,3-Benzothiadiazin-4(3H)-one-2,2-dioxide, 3-isopropyl- ; 3-(1-Methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide ; 3-Isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide ; 3-Isopropyl-1H-benzo-2,1,3-thiadiazin-4-one 2,2-dioxide ; 3-Isopropyl-2,1,3-benzothiadiazinon-(4)-2,2-dioxid ; Basagran ; Basagran-plus ; Bendioxide ; Bentazon ; EPA Pesticide Chemical Code 275200 ; Graminon-plus ; HSDB 3430 ; Herbatox ; Laddok ;
 Leader ; Pentazone ; Pledge.
Storage of Bentazone (CAS NO.25057-89-0): Protect against physical damage. Keep in tightly closed container in a shaded, well-ventilated area, away from heat, sparks and other sources of ignition. Keep out of reach of children and uninformed persons. Do not contaminate water, food or feed by storage or disposal.

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