Product Name

  • Name

    METHOXYFENOZIDE

  • EINECS 815-184-5
  • CAS No. 161050-58-4
  • Article Data9
  • CAS DataBase
  • Density 1.099 g/cm3
  • Solubility
  • Melting Point 204-205oC
  • Formula C22H28N2O3
  • Boiling Point
  • Molecular Weight 368.476
  • Flash Point
  • Transport Information
  • Appearance white crystal powder
  • Safety 60
  • Risk Codes 51/53
  • Molecular Structure Molecular Structure of 161050-58-4 (METHOXYFENOZIDE)
  • Hazard Symbols N
  • Synonyms 3,5-Dimethylbenzoicacid N-tert-butyl-N-(3-methoxy-2-methylbenzoyl)hydrazide;Intrepid(pesticide);Methoxyfenozide;Methoxyphenozide;RG 102398;RH 112485;RH 2485;Runner;Intrepid;
  • PSA 58.64000
  • LogP 4.59700

Synthetic route

3-methoxy-2-methylbenzoyl chloride
24487-91-0

3-methoxy-2-methylbenzoyl chloride

N-(3,5-Dimethylbenzoyl)-N-tert-Butyl-Hydrazine
162752-59-2

N-(3,5-Dimethylbenzoyl)-N-tert-Butyl-Hydrazine

methoxyfenoside
161050-58-4

methoxyfenoside

Conditions
ConditionsYield
With triethylamine for 4h; Acylation;61.6%
In 1,2-dichloro-ethane at 20℃; for 15h;
N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine
163336-50-3

N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine

3,5-dimethylbenzoyl chloride
6613-44-1

3,5-dimethylbenzoyl chloride

methoxyfenoside
161050-58-4

methoxyfenoside

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane
3-methoxy-2-methylbenzoic acid
55289-06-0

3-methoxy-2-methylbenzoic acid

N-(3,5-Dimethylbenzoyl)-N-tert-Butyl-Hydrazine
162752-59-2

N-(3,5-Dimethylbenzoyl)-N-tert-Butyl-Hydrazine

methoxyfenoside
161050-58-4

methoxyfenoside

Conditions
ConditionsYield
In thionyl chloride; dichloromethane
tert-butylhydrazine
32064-67-8

tert-butylhydrazine

3-methoxy-2-methylbenzoyl chloride
24487-91-0

3-methoxy-2-methylbenzoyl chloride

3,5-dimethylbenzoyl chloride
6613-44-1

3,5-dimethylbenzoyl chloride

methoxyfenoside
161050-58-4

methoxyfenoside

Conditions
ConditionsYield
Stage #1: tert-butylhydrazine With di-tert-butyl dicarbonate; sodium hydroxide In toluene at 0 - 5℃; for 10h;
Stage #2: 3,5-dimethylbenzoyl chloride With sodium hydroxide In water; toluene at 0 - 5℃; for 4h;
Stage #3: 3-methoxy-2-methylbenzoyl chloride Further stages;
...Expand
3,5-dimethylbenzoic acid
499-06-9

3,5-dimethylbenzoic acid

methoxyfenoside
161050-58-4

methoxyfenoside

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / toluene / 6.7 h / 55 °C
2.1: di-tert-butyl dicarbonate; sodium hydroxide / toluene / 10 h / 0 °C
2.2: 5 h / 0 °C
3.1: 1,2-dichloro-ethane / 15 h / 20 °C
View Scheme
phosgene
75-44-5

phosgene

methoxyfenoside
161050-58-4

methoxyfenoside

5-(3,5-dimethylphenyl)-3-(3-methoxy-2-methylbenzoyl)-3H-[1,3,4]-oxadiazol-2-one

5-(3,5-dimethylphenyl)-3-(3-methoxy-2-methylbenzoyl)-3H-[1,3,4]-oxadiazol-2-one

Conditions
ConditionsYield
Stage #1: methoxyfenoside With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: phosgene In tetrahydrofuran; ethyl acetate at -78℃;		95%
thiophosgene
463-71-8

thiophosgene

methoxyfenoside
161050-58-4

methoxyfenoside

3-(3-methoxy-2-methylbenzoyl)-5-(3,5-dimethylphenyl)-3H-[1,3,4]-oxadiazol-2-thione

3-(3-methoxy-2-methylbenzoyl)-5-(3,5-dimethylphenyl)-3H-[1,3,4]-oxadiazol-2-thione

Conditions
ConditionsYield
Stage #1: methoxyfenoside With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: thiophosgene In tetrahydrofuran; ethyl acetate at -78℃;		75%
α-chlorobenzyl chloroformate
81363-09-9

α-chlorobenzyl chloroformate

methoxyfenoside
161050-58-4

methoxyfenoside

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-phenyl-methyl ester
353755-64-3

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-phenyl-methyl ester

Conditions
ConditionsYield
Stage #1: methoxyfenoside With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: α-chlorobenzyl chloroformate In tetrahydrofuran at 20℃;
methoxyfenoside
161050-58-4

methoxyfenoside

C9H8Cl2O2
400848-58-0

C9H8Cl2O2

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-p-tolyl-methyl ester
353757-40-1

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-p-tolyl-methyl ester

Conditions
ConditionsYield
Stage #1: methoxyfenoside With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: C9H8Cl2O2 In tetrahydrofuran at 20℃;
methoxyfenoside
161050-58-4

methoxyfenoside

C9H8Cl2O2
400848-56-8

C9H8Cl2O2

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-o-tolyl-methyl ester
353757-39-8

N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(3-methoxy-2-methyl-benzoyl)-hydrazinecarboxylic acid chloro-o-tolyl-methyl ester

Conditions
ConditionsYield
Stage #1: methoxyfenoside With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: C9H8Cl2O2 In tetrahydrofuran at 20℃; for 4h;

Methoxyfenozide Chemical Properties

IUPAC Name: N-tert-Butyl-N'-(3-methoxy-2-methylbenzoyl)-3,5-dimethylbenzohydrazide
Synonyms: Benzoic acid,3-methoxy-2-methyl-,2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide ; Intrepid ; Methoxyfenozide [ISO:ANSI:BSI] ; N'-(3,5-Dimethylbenzoyl)-3-methoxy-2-methyl-N'-(2-methyl-2-propanyl)benzohydrazid ; N'-(3,5-Dimethylbenzoyl)-3-methoxy-2-methyl-N'-(2-methyl-2-propanyl)benzohydrazide ; N'-(3,5-Diméthylbenzoyl)-3-méthoxy-2-méthyl-N'-(2-méthyl-2-propanyl)benzohydrazide
CAS NO: 161050-58-4
Molecular Formula of Methoxyfenozide (CAS NO.161050-58-4) : C22H28N2O3
Molecular Weight of Methoxyfenozide (CAS NO.161050-58-4) :368.47
Molecular Structure of Methoxyfenozide (CAS NO.161050-58-4) :
Mol File: 161050-58-4.mol
Index of Refraction: 1.558
Surface Tension: 41.4 dyne/cm
Density: 1.098 g/cm3
storage temp. 0-6°C
Melting point: 202 ~ 205 °C,
Appearance: pure white powder
Stability: Stable at 25 °C.
Solubility: The solubility in organic solvents are: dimethyl sulfoxide 11g/100g, cyclohexanone 9.9g/100g, acetone 9g/100g, in water solubility <1mg / L.
 

Methoxyfenozide Uses

 Methoxyfenozide (CAS NO.161050-58-4) is diaryl hydrazine insect growth regulators, insecticides of molting hormones ,interfere with normal growth and development of insects and suppress feeding. In particular, there are effects on the larvae and eggs.

Methoxyfenozide Production

Raw materials :N,N-Dimethylformamide-->Thionyl chloride-->Hexane-->tert-Butylhydrazine hydrochloride-->2,6-Dichlorotoluene-->3,5-Dimethylbenzoic acid-->3-Methoxy-2-methylbenzoic acid-->TERT-BUTYL-HYDRAZINE-->3,5-DIMETHOXYBENZOYL CHLORIDE-->3-Methoxy-2-methylbenzoyl chloride
1. Methoxyfenozide (CAS NO.161050-58-4) can be obtained by the way of Oxadiazole ring-opening.
2. Obtained by amino protection.

Methoxyfenozide Toxicity Data With Reference

1.    

orl-mus LD50:5000 mg/kg

     FEREAC    Federal Register. 66 (2001),15449.
2.    

orl-rat LD50:5000 mg/kg

     FEREAC    Federal Register. 66 (2001),15449.
3.    

ihl-rat LC50:4.3 g/m3

     FEREAC    Federal Register. 66 (2001),15449.
4.    

skn-rat LD50:2000 mg/kg

     FEREAC    Federal Register. 66 (2001),15455.

Methoxyfenozide Safety Profile

Low toxicity by ingestion, inhalation, and skin contact. When heated to decomposition it emits toxic vapors of NOx.

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