Conditions | Yield |
---|---|
With chlorosulfonic acid; trichlorophosphate In water; 1,2-dichloro-ethane | 96.7% |
With chlorosulfonic acid; trichlorophosphate In water; 1,2-dichloro-ethane | 96.8% |
With sulfur trioxide; trichlorophosphate In water; 1,2-dichloro-ethane | 94.1% |
N-isopropyl-N'-o-carbomethoxy-phenyl-sulfamide
Bentazon
Conditions | Yield |
---|---|
With sodium methylate In methanol at 40℃; for 2h; |
2-carbomethoxyaniline
Bentazon
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / toluene / 1 h / 80 °C 2: MeONa / methanol / 2 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
With sulfur trioxide; trichlorophosphate In 1,2-dichloro-ethane |
2-amino-N-isopropylbenzamide
Bentazon
Conditions | Yield |
---|---|
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 |
Bentazon
Conditions | Yield |
---|---|
In isobutanolic potassium hydroxide | 97.3% |
2-biphenylmethanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 91% |
Bentazon
1-bromomethyl-4-nitro-benzene
3-Isopropyl-1-(4-nitro-benzyl)-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 0.333333h; Heating; | 89% |
1-naphthalene methanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 88% |
pyridine-4-methanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 86% |
3-Nitrobenzyl alcohol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 82% |
methyl 5-(bromomethyl)-furan-2-carboxylate
Bentazon
5-(3-Isopropyl-2,2,4-trioxo-3,4-dihydro-2H-2λ6-benzo[1,2,6]thiadiazin-1-ylmethyl)-furan-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 0.333333h; Heating; | 79% |
2-Naphthalenemethanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 76% |
biphenyl-4-yl methanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 76% |
Bentazon
α-bromoacetophenone
3-Isopropyl-2,2-dioxo-1-(2-oxo-2-phenyl-ethyl)-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 0.333333h; Heating; | 75% |
3-(bromomethyl)-1,1'-biphenyl
Bentazon
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 3h; | 74% |
zinc(II) nitrate
Bentazon
Conditions | Yield |
---|---|
With sodium hydroxide In water Bazagran is added to a soln. of NaOH, filtn., a soln. of the metal salt is added to the filtrate with stirring.; The ppt. is left under the mother soln. for 1 day, concg., filtn. under reduced pressure, washing with cold water, drying in air, elem. anal.; | 71% |
1-bromo-butane
Bentazon
1-Butyl-3-isopropyl-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 0.333333h; Heating; | 69% |
3,5-bis(1,1-dimethylethyl)benzenemethanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 68% |
3-iodobenzylalcohol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 67% |
Bentazon
Conditions | Yield |
---|---|
With sodium hydroxide In water Bazagran is added to a soln. of NaOH, filtn., a soln. of the metal salt is added dropwise to the filtrate with stirring.; The ppt. is left under the mother soln. for 1 day, filtn. under reduced pressure, washing with cold water, drying in air, elem. anal.; | 65% |
1,1-Diphenylmethanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 63% |
benzoyl chloride
Bentazon
1-benzyl-3-isopropyl-2,2-dioxo-2,3-dihydro-1H-2λ6-benzo[1,2,6]thiadiazin-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 0.333333h; Heating; | 52% |
3,5-di-tert-butyl-4-hydroxybenzyl alcohol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 45% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; |
2-(2-Hydroxyethyl)pyridine
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 39% |
(4-hydroxyphenyl)methanol
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 21% |
1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione
Bentazon
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 20% |
Bentazon
cyclohexanol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; | 12% |
Bentazon
2-isopropyl-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide
Conditions | Yield |
---|---|
In hexane Irradiation; |
benzene-1,2-diol
Bentazon
Conditions | Yield |
---|---|
laccase from Polyporus pinsitus at 25℃; for 4h; pH=3.0 - 7.0; Substitution; Enzymatic reaction; |
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 12h; Methylation; |
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 (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.
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).
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. |
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Hazard Codes: Xn,F
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 , 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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