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Basic Information
CAS No.: 161050-58-4
Name: METHOXYFENOZIDE
Molecular Structure:
Molecular Structure of 161050-58-4 (METHOXYFENOZIDE)
Formula: C22H28N2O3
Molecular Weight: 368.476
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;
EINECS: 815-184-5
Density: 1.099 g/cm3
Melting Point: 204-205oC
Appearance: white crystal powder
Hazard Symbols: N
Risk Codes: 51/53
Safety: 60
PSA: 58.64000
LogP: 4.59700
Synthetic route
24487-91-0

3-methoxy-2-methylbenzoyl chloride

162752-59-2

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

161050-58-4

methoxyfenoside

Conditions
ConditionsYield
With triethylamine for 4h; Acylation;61.6%
In 1,2-dichloro-ethane at 20℃; for 15h;
163336-50-3

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

6613-44-1

3,5-dimethylbenzoyl chloride

161050-58-4

methoxyfenoside

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane
55289-06-0

3-methoxy-2-methylbenzoic acid

162752-59-2

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

161050-58-4

methoxyfenoside

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

tert-butylhydrazine

24487-91-0

3-methoxy-2-methylbenzoyl chloride

6613-44-1

3,5-dimethylbenzoyl chloride

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;
499-06-9

3,5-dimethylbenzoic acid

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
75-44-5

phosgene

161050-58-4

methoxyfenoside

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%
463-71-8

thiophosgene

161050-58-4

methoxyfenoside

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%
81363-09-9

α-chlorobenzyl chloroformate

161050-58-4

methoxyfenoside

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℃;
161050-58-4

methoxyfenoside

400848-58-0

C9H8Cl2O2

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℃;
161050-58-4

methoxyfenoside

400848-56-8

C9H8Cl2O2

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;
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Chemistry

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.
 

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.

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.

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.

Safety Profile

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