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Anilofos

Anilofos structure

Anilofos 

structure
  • CAS No:

    64249-01-0

  • Formula:

    C13H19ClNO3PS2

  • Chemical Name:

    Anilofos

  • Synonyms:

    Phosphorodithioic acid,S-[2-[(4-chlorophenyl)(1-methylethyl)amino]-2-oxoethyl] O,O-dimethyl ester;HOE 30374;HOE 574;Anilofos;Arozin;Aniloguard;Aniloguard 30EC;Shabailin

  • Categories:

    Organic Chemistry  >  Phosphines

Description

Anilofos is an anilide.

Anilofos Basic Attributes

367.85

367.85

264-756-5

71W48U40S6

DTXSID5058149

Characteristics

96.2

4.98250

colorless crystal

1.322 g/cm3

51 °C

443.6ºC at 760 mmHg

>100 °C

1.561 (24ºC)

3.70e-05 M

0-6°C

LD50 orl-rat: 472 mg/kg PEMNDP 9,36,1991

Safety Information

UN 3077

2

22-51/53

60-61

TD5185000

Xn;N,N,Xn

P264, P270, P301+P312, P330, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

(S-4-chloro-N'-isopropylcarbaniloylmethyl-O-O-dimethylphosphorodithioate)

Anilofos Use and Manufacturing

Methods of Manufacturing

Alkylation reaction: 0.376 mol of p-chloroaniline and 2-bromopropane are mixed and heated, react for several hours at a certain temperature, cool, add sodium hydroxide solution and stir to separate layers, wash the oil layer with water until it is neutral, extract the water layer with solvent, and merge the oil layers , Desolventize to obtain 64g of purple liquid, prepare 4-chloro-N-isopropylaniline with a yield of 95% to 98%. Or use p-nitrochlorobenzene to react with acetone and hydrogen simultaneously to produce 4-chloro-N-isopropylaniline. Or it can be prepared by reacting p-chloroaniline and isopropanol in the presence of a solid catalyst at 135-140℃ and 0.67-0.7MPa for 5h. Chloroacetylation reaction Mix 0.48 mol of the product in the previous step, solvent, and chloroacetyl chloride, then heat, and react at a certain temperature for several hours. Add water and stir, stand for layering, wash the oil layer with water, extract the water layer, combine the oil layers, after desolventizing, 119 g of light red N-chloroacetyl-N-isopropyl p-chloroaniline, the yield is 98%. There are also reports of using pyridine as an acid binding agent to carry out the reaction at a lower temperature. In the condensation reaction, 0.17 mol of N-chloroacetyl-N-isopropyl p-chloroaniline, acid binding agent, solvent and O, O-dimethyl dithiophosphoric acid are mixed, and the reaction is stirred for several hours at a certain temperature. After eluting with water, 63g of Sardinium product was obtained, with a yield of 88% to 90%.

Uses

Systemic organophosphorus herbicide. The agent is absorbed through the root system and transmitted to the shoots or leaves, which inhibits the growth of the plant and changes its color to dark green. Sometimes it is discolored, stops growing, and finally dies. It is used to control monocotyledonous weeds in rice fields, such as barnyard grass, sedge grass, crushed rice sedge, rhododendron, oxgrass, knotweed, flutter grass, etc. The effect of early application is good, and the late application cannot be completely controlled. The general dosage is 4.5g active ingredient/100m2. It is applied at the 2.5-leaf stage of barnyardgrass (4-8d after transplanting), sprayed with emulsifiable concentrate 3g active ingredient/100m2, and lasts for 20-30 days, with 3-6g active ingredient/ 100m2 is also effective for dry land weeds.

Computed Properties

Molecular Weight:367.9
XLogP3:3.8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:367.0232505
Monoisotopic Mass:367.0232505
Topological Polar Surface Area:96.2
Heavy Atom Count:21
Complexity:382
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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