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112410-23-8

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112410-23-8 Usage

General Description

Tebufenozide is an ecdysone insecticide, which causes the premature molting of insects by interfering with the normal development of insects. It has high insecticidal activity and high selectivity, being effective in treatment of all lepidopteran larvae, caterpillar, diamondback moth and beet armyworm. It has a strong ovicidal activity, being safe to non-target organisms. Tebfenozide has no irritating effect on the eyes and skin without any teratogenic, carcinogenic and mutagenic effects on higher animals, being of high safety to mammals, birds and natural enemies. It is an ideal insecticide during integrated control.

Chemical Properties

Pure white powder, melting point 191 ℃. Slightly soluble in water and organic solvents; stable to light. It is stable at 5 ° C in pH 7 aqueous solution upon light emission.

Toxicity (to higher animals)

Low toxicity

Mechanism of Action

Tebufenozide is a pro-skinning compound that selectively controls lepidopteran larvae by acting in close association with the descorticophilin receptor protein. During its effect, tebufenozide mimics the action of natural insect pest hormone 20-hydroxy-descorticoid, leading to its premature, deadly peeling.

Control object and using method

It can be used to control a variety of lettuce larvae such as cabbage, apples and other crops. It is effective in the treatment of all instar larvae at drug interval of 14d. Control Spodoptera exigua, Spodoptera litura, Spodoptera frugiperda, melon field borer and cabbage budworm; apply in the early larvae emergence, spray 1 500 ~ 2 000 times 20% SC. Control apple leaf roller and peach moth worm, Spray 1000 ~ 2000 times 20% suspension. Control corn borer and bean curl moth; spray 1000 ~ 2000 times 20% suspension.

Attention

This product is toxic to silkworms, should pay attention to be away from the silkworm area. This product is generally effective against Plutella xylostella and can be mixed with avermectin. Spray uniformly; ensure that the contact of liquid with parasites. It is best to apply pesticide in the evening when controlling beet armyworm.

Uses

Different sources of media describe the Uses of 112410-23-8 differently. You can refer to the following data:
1. Tebufenozide is used to control lepidopterous larvae on rice, fruit, row crops, nut crops, vegetables and vines and in forestry.
2. Synthetic nonsteroidal ecdysone agonist causing premature molting; novel insect growth regulator specific to lepidopteran species. Insecticide.

Definition

ChEBI: A carbohydrazide that is hydrazine in which the amino hydrogens have been replaced by tert-butyl, 3,5-dimethylbenzoyl and 4-ethylbenzoyl groups respectively. It is an insecticide used widely against caterpillars.

Hazard

Low toxicity by ingestion, inhalation, and skin contact.

Agricultural Uses

Insecticide, Insect growth regulator: Tebufenozide is an insect growth regulator that interferes with molting of Lepidopteran larvae. It is used on fruitworm, fireworms, false armyworm, gypsy moth, and spanworms, and is applied pre-harvest. Registered for use in EU countries. Registered for use in the U.S.

Trade name

CONFIRM?; MIMIC?; RH-5992?

Metabolic pathway

Oxidation of ethyl and methyl substituents of the phenyl rings of tebufenozide occurs in soils and plants, to give carboxylic acids, alcohols and a ketone.

Degradation

Tebufenozide was stable at 94 °C for 7 days, stable to light in pH 7 aqueous solution (25 °C) and stable in dark sterile water for 30 days (25 °C). The DT50 in natural pond water, in light, was 30 days (25 °C) (PM). It was stable in acidic and neutral buffer solutions. Hydrolysis was marked in alkaline conditions (DT50 203 days, pH 10, 20°C). Tebufenozide was stable in sterilised stream water in the dark but degraded in non-sterile water (DT50 181 days). The insecticide was photodegraded by sunlight (DT50 83 hours, summer 46°N). The results suggest that microbial degradation and photolysis will be the main routes of tebufenozide dissipation in natural aquatic conditions (Sundaram, 1994).

Check Digit Verification of cas no

The CAS Registry Mumber 112410-23-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,4,1 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 112410-23:
(8*1)+(7*1)+(6*2)+(5*4)+(4*1)+(3*0)+(2*2)+(1*3)=58
58 % 10 = 8
So 112410-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H28N2O2/c1-7-17-8-10-18(11-9-17)20(25)23-24(22(4,5)6)21(26)19-13-15(2)12-16(3)14-19/h8-14H,7H2,1-6H3,(H,23,25)

112410-23-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name tebufenozide

1.2 Other means of identification

Product number -
Other names RoMdan

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:112410-23-8 SDS

112410-23-8Synthetic route

3,5-dimethylbenzoyl chloride
6613-44-1

3,5-dimethylbenzoyl chloride

1-(4-ethylbenzoyl)-2-t-butyl hydrazine
139303-74-5

1-(4-ethylbenzoyl)-2-t-butyl hydrazine

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether for 48h; Ambient temperature;
p-ethylbenzoyl chloride
16331-45-6

p-ethylbenzoyl chloride

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

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

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 20℃;
3,5-dimethylbenzoic acid
499-06-9

3,5-dimethylbenzoic acid

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.2 percent / SOCl2 / 5 h / 80 °C
2: 1N aq. NaOH / diethyl ether / 48 h / Ambient temperature
View Scheme
p-ethylbenzoic acid
619-64-7

p-ethylbenzoic acid

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 5 h / 80 °C
2: aq. NaOH / dioxane / 48 h / Ambient temperature
3: 1N aq. NaOH / diethyl ether / 48 h / Ambient temperature
View Scheme
p-ethylbenzoyl chloride
16331-45-6

p-ethylbenzoyl chloride

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / dioxane / 48 h / Ambient temperature
2: 1N aq. NaOH / diethyl ether / 48 h / Ambient temperature
View Scheme
p-ethylbenzoyl chloride
16331-45-6

p-ethylbenzoyl chloride

tertbutylhydrazine hydrochloride
7400-27-3

tertbutylhydrazine hydrochloride

3,5-dimethylbenzoyl chloride
6613-44-1

3,5-dimethylbenzoyl chloride

tebufenozide
112410-23-8

tebufenozide

Conditions
ConditionsYield
With sodium hydroxide In toluene
phosgene
75-44-5

phosgene

tebufenozide
112410-23-8

tebufenozide

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

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

Conditions
ConditionsYield
Stage #1: tebufenozide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: phosgene In tetrahydrofuran; ethyl acetate at -78℃; for 0.5h;
95%
thiophosgene
463-71-8

thiophosgene

tebufenozide
112410-23-8

tebufenozide

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

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

Conditions
ConditionsYield
Stage #1: tebufenozide With potassium tert-butylate In tetrahydrofuran at 20℃;
Stage #2: thiophosgene In tetrahydrofuran; ethyl acetate at -78℃;
80%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

tebufenozide
112410-23-8

tebufenozide

[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-acetic acid ethyl ester

[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-acetic acid ethyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 35 - 40℃; for 10h;
62%
tebufenozide
112410-23-8

tebufenozide

2-(3,5-dimethyl)-phenyl-5-(4-ethylphenyl)-1,3,4-oxadiazole

2-(3,5-dimethyl)-phenyl-5-(4-ethylphenyl)-1,3,4-oxadiazole

Conditions
ConditionsYield
With pyridine; oxalyl dichloride In 1,2-dichloro-ethane at 20℃; for 6h;60.8%
With pyridine; oxalyl dichloride In dichloromethane at 20℃;
chlorosulfenyl[O-(1-methylthioethylimino)-N-methylcarbamate]
1051431-26-5

chlorosulfenyl[O-(1-methylthioethylimino)-N-methylcarbamate]

tebufenozide
112410-23-8

tebufenozide

C27H36N4O4S2

C27H36N4O4S2

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In xylene for 2h; Heating;
Stage #2: chlorosulfenyl[O-(1-methylthioethylimino)-N-methylcarbamate] In xylene at 20℃; for 6h; Further stages.;
52%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

tebufenozide
112410-23-8

tebufenozide

[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-acetic acid methyl ester

[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: bromoacetic acid methyl ester In N,N-dimethyl-formamide at 35 - 40℃; for 10h;
50%
oxalyl dichloride
79-37-8

oxalyl dichloride

tebufenozide
112410-23-8

tebufenozide

A

4-tert-butyl-2-(4-ethylphenyl)-4H-1,3,4-oxadiazine-5,6-dione

4-tert-butyl-2-(4-ethylphenyl)-4H-1,3,4-oxadiazine-5,6-dione

B

2-(3,5-dimethyl)-phenyl-5-(4-ethylphenyl)-1,3,4-oxadiazole

2-(3,5-dimethyl)-phenyl-5-(4-ethylphenyl)-1,3,4-oxadiazole

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 8h; Heating;A 45.3%
B 32%
In 1,2-dichloro-ethane Heating;
chlorooxalyl-methyl-carbamic acid m-tolyl ester

chlorooxalyl-methyl-carbamic acid m-tolyl ester

tebufenozide
112410-23-8

tebufenozide

{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetyl}-methyl-carbamic acid m-tolyl ester

{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetyl}-methyl-carbamic acid m-tolyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: chlorooxalyl-methyl-carbamic acid m-tolyl ester In tetrahydrofuran at 20℃; for 4h;
42.8%
chlorooxalyl-methyl-carbamic acid 2-isopropyl-phenyl ester

chlorooxalyl-methyl-carbamic acid 2-isopropyl-phenyl ester

tebufenozide
112410-23-8

tebufenozide

{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetyl}-methyl-carbamic acid 2-isopropyl-phenyl ester

{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetyl}-methyl-carbamic acid 2-isopropyl-phenyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: chlorooxalyl-methyl-carbamic acid 2-isopropyl-phenyl ester In tetrahydrofuran at 20℃; for 4h;
40.5%
phenyl oxalyl chloride
51719-70-1

phenyl oxalyl chloride

tebufenozide
112410-23-8

tebufenozide

N'-tert-butyl-N'-3,5-dimethylbenzoyl-N-phenyloxyoxalyl-N-4-ethylbenzoylhydrazine

N'-tert-butyl-N'-3,5-dimethylbenzoyl-N-phenyloxyoxalyl-N-4-ethylbenzoylhydrazine

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: phenyl oxalyl chloride In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

4-chlorooxalyloxy-benzoic acid methyl ester

4-chlorooxalyloxy-benzoic acid methyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 4-chlorooxalyloxy-benzoic acid methyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

2-chlorooxalyloxy-benzoic acid methyl ester

2-chlorooxalyloxy-benzoic acid methyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 2-chlorooxalyloxy-benzoic acid methyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

3-chlorooxalyloxy-benzoic acid methyl ester

3-chlorooxalyloxy-benzoic acid methyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 3-chlorooxalyloxy-benzoic acid methyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

4-chlorooxalyloxy-benzoic acid isopropyl ester

4-chlorooxalyloxy-benzoic acid isopropyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 4-chlorooxalyloxy-benzoic acid isopropyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

2-chlorooxalyloxy-benzoic acid isopropyl ester

2-chlorooxalyloxy-benzoic acid isopropyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 2-chlorooxalyloxy-benzoic acid isopropyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

3-chlorooxalyloxy-benzoic acid isopropyl ester

3-chlorooxalyloxy-benzoic acid isopropyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 3-chlorooxalyloxy-benzoic acid isopropyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

4-chlorooxalyloxy-benzoic acid butyl ester

4-chlorooxalyloxy-benzoic acid butyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 4-chlorooxalyloxy-benzoic acid butyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

2-chlorooxalyloxy-benzoic acid butyl ester

2-chlorooxalyloxy-benzoic acid butyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 2-chlorooxalyloxy-benzoic acid butyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

3-chlorooxalyloxy-benzoic acid butyl ester

3-chlorooxalyloxy-benzoic acid butyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid butyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 3-chlorooxalyloxy-benzoic acid butyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

4-chlorooxalyloxy-benzoic acid benzyl ester
869878-47-7

4-chlorooxalyloxy-benzoic acid benzyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester

4-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 4-chlorooxalyloxy-benzoic acid benzyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

2-chlorooxalyloxy-benzoic acid benzyl ester
869879-62-9

2-chlorooxalyloxy-benzoic acid benzyl ester

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester
784186-29-4

2-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 2-chlorooxalyloxy-benzoic acid benzyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

3-chlorooxalyloxy-benzoic acid benzyl ester
869881-36-7

3-chlorooxalyloxy-benzoic acid benzyl ester

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester
784186-37-4

3-{[N'-tert-butyl-N'-(3,5-dimethyl-benzoyl)-N-(4-ethyl-benzoyl)-hydrazino]-oxo-acetoxy}-benzoic acid benzyl ester

Conditions
ConditionsYield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: 3-chlorooxalyloxy-benzoic acid benzyl ester In tetrahydrofuran at 20℃; for 5h;
tebufenozide
112410-23-8

tebufenozide

C22H27ClN2O2S
1037075-79-8

C22H27ClN2O2S

Conditions
ConditionsYield
With pyridine; sulfur dichloride In dichloromethane at 20℃; for 4h;
tebufenozide
112410-23-8

tebufenozide

ethyl 2-(N'-tert-butyl-4-ethylbenzoylamido)-2-oxoacetate

ethyl 2-(N'-tert-butyl-4-ethylbenzoylamido)-2-oxoacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45.3 percent / 1,2-dichloro-ethane / 8 h / Heating
2: 92.7 percent / 2 h / Heating
View Scheme
tebufenozide
112410-23-8

tebufenozide

4-ethyl-N-phenyl benzamide
84270-05-3

4-ethyl-N-phenyl benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tBuOK / tetrahydrofuran / 1 h / 20 °C
1.2: 95 percent / tetrahydrofuran; ethyl acetate / 0.5 h / -78 °C
2.1: 300 mg / tetrahydrofuran / 4 h
View Scheme
tebufenozide
112410-23-8

tebufenozide

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tBuOK / tetrahydrofuran / 1 h / 20 °C
1.2: 95 percent / tetrahydrofuran; ethyl acetate / 0.5 h / -78 °C
2.1: 250 mg / tetrahydrofuran / 4 h
View Scheme

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Adult development and production of up to 400 eggs within the pupal case of female silkmoths are both dependent on 20-hydroxyecdysone (20E), the steroid hormone of insects. When adult development was initiated with tebufenozide, the non-steroidal ecdysteroid agonist, instead of 20E, full develop...detailed

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The novel nonsteroidal ecdysone agonist tebufenozide is capable of controlling a wide range of lepidopteran pests. However its intensive use in vegetables has raised concerns towards the safety of food and environment. Here, we developed an easy and reliable method to analyze tebufenozide in cab...detailed

Tebufenozide (cas 112410-23-8) induces G1/S cell cycle arrest and apoptosis in human cells07/23/2019

Tebufenozide is a non-steroidal insect growth regulator and is extensively used to control pests, although it is considered to be safe for mammals and environmentally friendly. However, previous studies have found that tebufenozide is cytotoxic to man, although the exact mechanism remains elusiv...detailed

Residue analysis and dietary exposure risk assessment of Tebufenozide (cas 112410-23-8) in stem lettuce (Lactuca sativa L. var. angustana Irish)07/22/2019

Tebufenozide, a newly-developed nonsteroidal ecdysone agonist, is in pre-regulation phase (before approval for use) on stem lettuce in China. Aiming at the safe application of tebufenozide, the dissipation and terminal residue trials on stem lettuce were performed under good agricultural practic...detailed

Cytotoxic effects of Tebufenozide (cas 112410-23-8) in vitro bioassays07/20/2019

Tebufenozide is considered an environmentally friendly pesticide due to its specificity on target insects, but the effects on human are well studied. Studies on the toxicity of tebufenozide at molecular and cellular level is poorly understood. The present study reveals non-selective cytotoxic ef...detailed

Toxicological and morphological effects of Tebufenozide (cas 112410-23-8) on Anticarsia gemmatalis (Lepidoptera: Noctuidae) larvae07/21/2019

The velvetbean caterpillar, Anticarsia gemmatalis Hübner (Lepidoptera: Noctuidae), is an important soybean pest in the Americas. Tebufenozide, a novel nonsteroidal ecdysone agonist is used to control this pest. Bioassays were conducted to assess tebufenozide toxicity and their ultrastructural e...detailed

Molecular mechanisms conferring asymmetrical cross-resistance between Tebufenozide (cas 112410-23-8) and abamectin in Plutella xylostella07/19/2019

Based on the confirmation of asymmetrical cross-resistance between abamectin and tebufenozide in Plutella xylostella, the present work proved that the cytochrome P450 monooxygenase plays a decisive role in cross-resistance, and the expression of various cytochrome P450 (CYP450) genes in differen...detailed

112410-23-8Relevant articles and documents

Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides

Shimizu, Bun-Ichi,Nakagawa, Yoshiaki,Hattori, Kazunari,Nishimura, Keiichiro,Kurihara, Norio,Ueno, Tamio

, p. 638 - 642 (1997)

Dibenzoylhydrazines are the nonsteroidal ecdysone agonists. Using comparative molecular field analysis, we previously found that the alkyl side chain of 20-hydroxyecdysone (20E) is three-dimensionally superposable with one of their two aryl moieties. To identify the aryl moiety that is better superposable on the alkyl chain, we synthesized compounds in which one of the two aryl groups of tebufenozide (N-t-butyl-N-3,5-dimethylbenzoyl-N'-4- ethylbenzoylhydrazine) is replaced by alkyl groups such as C4H9, C5H11, and C6H13. The molting hormonal activity of these compounds was measured using cultured integuments prepared from rice stem borers, Chilo suppressalis Walker, in terms of stimulation of incorporation of N:acetyl- [14C]glucosamine. N-t-Butyl-N-3,5-dimethylbenzoyl-N'-acylhydrazines with a hexanoyl or heptanoyl group were about 20-fold higher than that of 20E, whereas N-acyl-N-t-butyl-N'-4-ethylbenzoylhydrazines with a hexanoyl or heptanoyl group were much weaker than 20E. Their larvicidal activity was also measured against rice stem borers. The former series of compounds were much more active than the other series as well as 20E. Thus, the benzoyl moiety of dibenzoylhydrazines, which is bound to the secondary nitrogen atom (-NH-), is replaceable by aliphatic acyl groups without, greatly, affecting the biological activities.

Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

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Page/Page column 5, (2008/06/13)

The present invention relates to non-steroidal ligands for use in nuclear receptor-based inducible gene expression system, and a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene.

Insecticidal combination to control mammal fleas, in particular fleas on cats and dogs

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, (2008/06/13)

Process and composition, in particular for controlling fleas on small mammals, characterized in that the composition includes, on the one hand, at least one insecticide of 1-N-arylpyrazole type, in particular fipronil, and, on the other hand, at least one compound of IGR (insect growth regulator) type, in doses and proportions which are parasiticidally effective on fleas, in a fluid vehicle which is acceptable for the animal and convenient for local application to the skin, preferably localized over a small surface area.

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