Tebufenozide supplier | CasNO.112410-23-8

Name
Tebufenozide
EINECS 412-850-3
CAS No. 112410-23-8
Article Data8
CAS DataBase
Density 1.074 g/cm³
Solubility 0.83 mg l-1 (20 °C)
Melting Point 191oC
Formula C₂₂H₂₈N₂O₂
Boiling Point
Molecular Weight 352.477
Flash Point
Transport Information
Appearance
Safety 61
Risk Codes 51/53
Molecular Structure
Hazard Symbols N
Synonyms Mimic;Mimic 240LV;Mimic 700WP;RH 5992;Romdan;
PSA 49.41000
LogP 4.84240

Synthetic route

: 6613-44-1
3,5-dimethylbenzoyl chloride

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

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
With sodium hydroxide In diethyl ether for 48h; Ambient temperature;

: 16331-45-6
p-ethylbenzoyl chloride

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

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃;

: 499-06-9
3,5-dimethylbenzoic acid

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
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

: 619-64-7
p-ethylbenzoic acid

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
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

: 16331-45-6
p-ethylbenzoyl chloride

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
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

: 16331-45-6
p-ethylbenzoyl chloride

: 7400-27-3
tertbutylhydrazine hydrochloride

: 6613-44-1
3,5-dimethylbenzoyl chloride

: 112410-23-8
tebufenozide

Conditions

Conditions	Yield
With sodium hydroxide In toluene

...Expand

: 75-44-5
phosgene

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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%

: 463-71-8
thiophosgene

: 112410-23-8
tebufenozide

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

Conditions

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

: 105-36-2
ethyl bromoacetate

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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%

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
With pyridine; oxalyl dichloride In 1,2-dichloro-ethane at 20℃; for 6h;	60.8%
With pyridine; oxalyl dichloride In dichloromethane at 20℃;

: 1051431-26-5
chlorosulfenyl[O-(1-methylthioethylimino)-N-methylcarbamate]

: 112410-23-8
tebufenozide

: C27H36N4O4S2

Conditions

Conditions	Yield
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%

: 96-32-2
bromoacetic acid methyl ester

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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%

: 79-37-8
oxalyl dichloride

: 112410-23-8
tebufenozide

A: 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

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 8h; Heating;	A 45.3% B 32%
In 1,2-dichloro-ethane Heating;

...Expand

: chlorooxalyl-methyl-carbamic acid m-tolyl ester

: 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

Conditions

Conditions	Yield
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

: 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

Conditions

Conditions	Yield
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%

: 51719-70-1
phenyl oxalyl chloride

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
Stage #1: tebufenozide With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: phenyl oxalyl chloride In tetrahydrofuran at 20℃; for 5h;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 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

Conditions

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 869879-62-9
2-chlorooxalyloxy-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

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 869881-36-7
3-chlorooxalyloxy-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

Conditions	Yield
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;

: 112410-23-8
tebufenozide

: 1037075-79-8
C22H27ClN2O2S

Conditions

Conditions	Yield
With pyridine; sulfur dichloride In dichloromethane at 20℃; for 4h;

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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

: 112410-23-8
tebufenozide

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

Conditions

Conditions	Yield
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

Tebufenozide Specification

The Tebufenozide technical is an organic compound with the formula C₂₂H₂₈N₂O₂. The IUPAC name of this chemical is N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide. With the CAS registry number 112410-23-8, it is also named as 1-(1,1-Dimethylethyl)-2-(4-ethylbenzoyl)hydrazide 3,5-dimethylbenzoate. The product's categories are Growth regulatorsPesticides & Metabolites; Alpha sort; Insecticides; Pesticides; Q-ZAlphabetic; TA - TE. Besides, it should be stored in a closed cool and dry place. It have the stomach poison function, it is a ecdysone agonist and can induce lepidopterous larvae molt in advance before its stage of molting. It is used to control most of the lepidopteron insects such as beet armyworm, cabbage armyworm, tortricid, pine cater pillar etc.

Physical properties about Tebufenozide technical are: (1)ACD/LogP: 4.24; (2)ACD/LogD (pH 5.5): 4.24; (3)ACD/LogD (pH 7.4): 4.24; (4)ACD/BCF (pH 5.5): 985.37; (5)ACD/BCF (pH 7.4): 985; (6)ACD/KOC (pH 5.5): 4835.24; (7)ACD/KOC (pH 7.4): 4833.41; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 40.62 Å²; (12)Index of Refraction: 1.561; (13)Molar Refractivity: 106.25 cm³; (14)Molar Volume: 327.8 cm³; (15)Polarizability: 42.12×10^-24cm³; (16)Surface Tension: 41.6 dyne/cm; (17)Density: 1.074 g/cm³.

Preparation: this chemical can be prepared by Oxadiazole ring. Reaction equation is as follows:

Uses of Tebufenozide technical: it can be used to produce [5-(3,5-dimethyl-phenyl)-2-thioxo-[1,3,4]oxadiazol-3-yl]-(4-ethyl-phenyl)-methanone at temperature of 200 °C. It will need reagent tBuOK and solvent tetrahydrofuran, tetrahydrofuran, ethyl acetate. The yield is about 80%.

When you are using this chemical, please be cautious about it as the following:
It is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. When you are using it, avoid release to the environment. Refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1cc(cc(c1)C)C)N(NC(=O)c2ccc(cc2)CC)C(C)(C)C
(2)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)
(3)InChIKey: QYPNKSZPJQQLRK-UHFFFAOYAS
(4)Std. InChI: InChI=1S/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)
(5)Std. InChIKey: QYPNKSZPJQQLRK-UHFFFAOYSA-N

Product Name

Tebufenozide

Synthetic route

Tebufenozide Specification

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