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Benazolin

Benazolin structure

CAS No:
3813-05-6
Formula:
C9H6ClNO3S
Chemical Name:
Benazolin
Synonyms:
(4-chloro-2-oxobenzothiazol-3-yl)-aceticaci;4-chloro-2-oxo-3(2h)-benzothiazoleaceticaci;4-chloro-2-oxo-3-benzothiazolineaceticaci;4-chloro-2-oxo-3-benzothiazolineaceticacid;4-chloro-2-oxobenzothiazol-3-ylaceticacid;ben-30;benasalox;benazalox
Categories:
Agrochemicals > Herbicides

Description

ChEBI: A member of the class of benzothiazoles that is 4-chloro-1,3-benzothiazol-2(3H)-one which is substituted on the nitrogen by a carboxymethyl group and at position 4 by chlorine. A post-emergence herbicide used (generally as a salt or este ) for the control of annual weeds in wheat and oilseed rape. It is not approved for use with the European Union.

Benazolin is a member of the class of benzothiazoles that is 4-chloro-1,3-benzothiazol-2(3H)-one which is substituted on the nitrogen by a carboxymethyl group and at position 4 by chlorine. A post-emergence herbicide used (generally as a salt or ester) for the control of annual weeds in wheat and oilseed rape. It is not approved for use with the European Union. It has a role as a herbicide and a synthetic auxin. It is a member of benzothiazoles, a monocarboxylic acid and an organochlorine pesticide. It is a conjugate acid of a benazolin(1-).

Moderately toxic by ingestion. Anherbicide. When heated to decomposition it emits toxicfumes of SOx, Cl-, and NOx.

Benazolin Basic Attributes

Molecular Weight：

243.67

Exact Mass：

243.67

EC Number：

223-297-0

UNII：

RB02FMB0BR

NSC Number：

521058

DSSTox ID：

DTXSID2041620

Color/Form：

White, crystalline solid

HScode：

29342000

Characteristics

PSA：

82.9

XLogP3：

2.21

Density：

1.3274 (rough estimate)

Melting Point：

192-196°C

Boiling Point：

468.4±55.0 °C(Predicted)

Flash Point：

100 °C

Refractive Index：

1.6300 (estimate)

Water Solubility：

0.6g/L(20 ºC)

Storage Conditions：

0-6°C

Vapor Pressure：

7.50e-10 mmHg

Toxicity：

Benazolin is primarily excreted in the urine as N-[2-chloro-6-(methylsulfinyl)phenyl]glycine and N-[N-[2-chloro-6-(methylthio)phenyl]glycinyl]aniline. Acid-labile conjugates of benazolin acid and N-[2-chloro- 6-(methylthio)phenylglycine] are also formed in small amounts. The acute oral LD50for rat and mice are >5000 mg/kg and >4000 mg/kg, respectively. See Table 21 for a list of toxicological data for benazolin.

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides, sulfur oxides and chloride gases

PKA：

3.50±0.10(Predicted)

Henrys Law Constant：

4.2×106mol/(m3Pa) at 25℃, Ebert et al. (2023)

Critical Temperature & Pressure：

0-6°C

Safety Information

Transport codes：

UN 3077

hazard class code：

Xi;N,N,Xi

safety instructions：

22-61

RTECS Number：

AF9700000

Marks：

Xi;N,N,Xi

Storage features：

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

Precautionary statement(s)：

P273-P305 + P351 + P338

Hazard Statements：

36/38-52/53

RIDADR：

UN 3077

GHS Classification：

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 197 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

moderately toxic

Mobility：

33.11 L/kg

Drug Information

MeSH Entry Terms：

2-(2-methylbenzo(b)thien-3-ylmethyl)-2-imidazoline

Benazolin Use and Manufacturing

Methods of Manufacturing

O-Chloroaniline reacts with ammonium thiocyanate to prepare o-chlorophenyl thiourea, then cyclize with chlorine gas to prepare 2-amino-4-chlorobenzothiazole, and then diazotize and hydrolyze to prepare 2-hydroxy-4 -Chlorobenzothiazole, finally reacts with ethyl chloroformate to produce ethyl chlorphenir, which is hydrolyzed to form chlorphenir

Uses

Suitable for weeding in sensitive crop rape fields

Benazolin is a selective systemic herbicide developed in the 1960s that has growth-regulatory action in susceptible plants. Structurally, it is a benzothiazolacetic acid and is unrelated to the four major groups of synthetic auxins discussed thus far. Benazolin controls a range of annual broadleaf weeds in alfalfa (Medicago sativa), canola (Brassica spp.), cereals, clover (Trifolium spp.), corn (Zea mays), grassland, and flax (Linum usitatissimum), and it has a relatively low persistence in the environment.

Use Classification：

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:243.67
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:242.9756919
Monoisotopic Mass:242.9756919
Topological Polar Surface Area:82.9
Heavy Atom Count:15
Complexity:299
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Benazolin

CAS No.: 3813-05-6

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