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161050-58-4

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161050-58-4 Usage

Description

Methoxyfenozide, a substituted dibenzoylhydrazine, is an insecticide that functions by accelerating the moulting process. It acts as an ecdysone agonist or ecdysonoid, substituting for the natural insect moulting hormone, 20-hydroxyecdysone. Methoxyfenozide is active on all feeding larval stages of the target Lepidoptera. It is used to control pests including codling moth, lesser apple worm, oriental fruit moth, leafrollers, cabbage looper, cotton bollworm, armyworm, and bud moths. It could be applied to leafy vegetables, fresh herbs, lettuce, salads, herbs, brassicas, cotton, pome fruit, grapes, sweetcorn, maize, peppers, and aubergines.

References

[1] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/461.htm [2] http://www.fao.org

Chemical Properties

White crystalline solid or powder.

Uses

Insecticide.

Definition

ChEBI: A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by 3-methoxy-2-methylbenzoyl, 3,5-dimethylbenzoyl, and tert-butyl groups respectively.

Hazard

Low toxicity by ingestion, inhalation, and skin contact.

Agricultural Uses

Insecticide: Methoxyfenozide prevents insects from molting, or shedding their exoskeleton in order to grow, e. g., caterpillars and lychee webworms.

Trade name

INTREPID?; PRODIGY?

Potential Exposure

Methoxyfenozide is a diacylhydrazine insecticide used to prevent insects from molting, or shedding their exoskeleton in order to grow, e.g., caterpillars and lychee webworms

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 161050-58-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,1,0,5 and 0 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 161050-58:
(8*1)+(7*6)+(6*1)+(5*0)+(4*5)+(3*0)+(2*5)+(1*8)=94
94 % 10 = 4
So 161050-58-4 is a valid CAS Registry Number.
InChI:InChI=1/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25)

161050-58-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name methoxyfenozide

1.2 Other means of identification

Product number -
Other names N-tert-butyl-N’-(3-methoxy-o-toluoyl)-3,5-xylohydrazide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:161050-58-4 SDS

161050-58-4Synthetic 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;
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;

161050-58-4Relevant articles and documents

Relationships between structure and molting hormonal activity of tebufenozide, methoxyfenozide, and their analogs in cultured integument system of Chilo suppressalis Walker

Nakagawa, Yoshiaki,Hattori, Kazunari,Minakuchi, Chieka,Kugimiya, Soichi,Ueno, Tamio

, p. 117 - 123 (2000)

The molting hormonal activity of methoxyfenozide (RH-2485), tebufenozide (RH-5992), five analogs with various alkyl groups, and 18 acyl analogs was measured by using cultured integument of rice stem borers, Chilo suppressalis Walker. The hormonal activity of methoxyfenozide was remarkably high (EC50 = 1.1 x 10-9 M), being equivalent to that of tebufenozide (RH-5992). The hormonal activity of several tebufenozide analogs with varying alkyl groups such as CH3, n-C3H7, i-C3H7, n-C4H9 and n-C5H11 at the para-position of the benzene ring furthest from the tert-butyl group was lower than that of tebufenozide (alkyl group is C2H5). The activity decreased to varying degrees as a result of replacement of the 3,5-dimethylphenyl moiety of tebufenozide with either a phenyl, naphthyl, or cyclohexyl group. Both 1- and 2-naphthyl derivatives were very active (EC50 = 4.3 x 10-8 M and 3.2 x 10-8 M, respectively) without any significant difference between them. The activity of the 1-cyclohexenyl analog (EC50 = 1.0 x 10-7 M) was about 40x that of the corresponding 3-cyclohexenyl analog (EC50 = 4.4 x 10-6 M), but 1/100 that of tebufenozide. The activity varied parabolically with respect to the molecular hydrophobicity, and decreased with longer acyl moieties. Copyright (C) 2000 Elsevier Science Inc.

Green preparation process of 2-methyl-3-methoxybenzoyl chloride

-

, (2021/07/14)

The invention discloses a green preparation process of 2-methyl-3-methoxybenzoyl chloride. The green preparation process comprises the following steps: heating and hydrolyzing methyl 2-methyl-3-methoxybenzoate in an alkaline aqueous solution, and distilling off generated methanol while a hydrolysis reaction is carried out; adding an organic solvent into hydrolyzed reaction liquid under the condition of heat preservation for dissolving, and adding an acidic aqueous solution for neutralizing; conducting neutralizing, then preserving heat and conducting layering to obtain a water layer and an organic layer, and washing the organic layer with water; heating the washed organic layer for azeotropic water removal; and adding a catalyst into the organic layer after azeotropic dehydration, carrying out heating, dropwise adding an acylating chlorination reagent, and carrying out a heat-preserved reaction to obtain the 2-methyl-3-methoxybenzoyl chloride. In a neutralization process after hydrolysis is completed, the organic solvent is added, and the product 2-methyl-3-methoxybenzoic acid is transferred into the organic solvent and is transferred to a subsequent reaction in a solution state, so water consumption for post-treatment is reduced, and meanwhile, harm to a working environment and the health of workers in the solid dust drying and feeding process is avoided.

Preparation method of methoxyfenozide

-

Paragraph 0010, (2018/07/30)

The invention discloses a preparation method of methoxyfenozide and relates to the field of insecticide, and particularly relates to the preparation method of methoxyfenozide. The preparation method includes steps of preparation of 3, 5-dimethylbenzoyl chloride: adding 3, 5-mesitylenic acid and methylbenzene in a reaction bottle; raising temperature to 60 DEG C, and dropwise adding thionyl chloride within 2 hours; preserving temperature for 3 hours, depressurizing and removing solvent to obtain 3, 5-dimethylbenzoyl chloride; synthesis of midbody: adding tert-butylhydrazine, sodium hydroxide and methylbenzene in the reaction bottle, and cooling to 0 DEG C; adding di-tert-butyl dicarbonate ester and reacting for 10 hours at 0-5 DEG C; removing a water layer, adding 3, 5-dimethylbenzoyl chloride and sodium hydroxide solution in an organic layer; reacting for 4 hours at 0-5 DEG C, filtering a product and adding the filter cake in methanol; adding hydrochloric acid in the reaction mixture;reacting for 20 hours at 35 DEG C; filtering the product, washing and drying to obtain the midbody. The preparation method is simple in operation, safe and reliable in reaction; the production efficiency is greatly improved, and the production cost is reduced; moreover, the product is high-efficient, low-toxic and environment-friendly.

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