112225-87-3

Basic information

• Product Name: 1,2-DIBENZOYL-1-(T-BUTYL)HYDRAZINE
• Synonyms: RH5849;benzoicacid,2-benzoyl-1-(1,1-dimethylethyl)hydrazide;1,2-DIBENZOYL-1-(T-BUTYL)HYDRAZINE;1,2-DIBENZOYL-1-TERT-BUTYLHYDRAZINE W.P.;1,2-dibenzoyl-tert-butylhydrazine;2BENZOYL1TERTBUTYLBENZOYLHYDRAZINE;1,2-Dibenzoyl-1-tert-butylhydrazine;Benzoic acid 2-benzoyl-1-tert-butyl hydrazide
• CAS NO: 112225-87-3
• Molecular Formula: C₁₈H₂₀N₂O₂
• Molecular Weight: 296.36
• Mol File: 112225-87-3.mol

Chemical Properties

• Melting Point: 178.5 °C
• Appearance: /
• Density: 1.128 g/cm³
• Refractive Index: 1.577
• PKA: 10.97±0.46(Predicted)
• CAS DataBase Reference: 1,2-DIBENZOYL-1-(T-BUTYL)HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIBENZOYL-1-(T-BUTYL)HYDRAZINE(112225-87-3)
• EPA Substance Registry System: 1,2-DIBENZOYL-1-(T-BUTYL)HYDRAZINE(112225-87-3)

Safety Data

• Hazardous Substances Data: 112225-87-3(Hazardous Substances Data)

Usage

Uses

Used in Pest Control Applications:
1,2-Dibenzoyl-1-(tert-butyl)hydrazine is used as an ecdysone agonist for pest control purposes. It targets the larval development of pests such as the tobacco hornworm, Manduca sexta, by causing premature initiation of molting at all stages of larval development. This disrupts the pest's life cycle and growth, making it an effective tool in managing and controlling pest populations in agricultural settings.

InChI:InChI=1/C18H20N2O2/c1-18(2,3)20(17(22)15-12-8-5-9-13-15)19-16(21)14-10-6-4-7-11-14/h4-13H,1-3H3,(H,19,21)

Upstream product

• 7400-27-3 tertbutylhydrazine hydrochloride 
• 98-88-4 benzoyl chloride 
• 17473-79-9 1-benzoyl-2-tert-butylhydrazine 
• 99981-48-3 N'-t-butyl-N'-benzoylhydrazine 
• 32154-73-7 tert-butylhydrazine oxalate 

Downstream Products

• 5894-65-5 N-t-butylbenzamide 
• 57064-92-3 3-benzoyl-5-phenyl-3H-[1,3,4]-oxadiazol-2-one 
• 857505-17-0 C₁₈H₁₉ClN₂O₂S 
• 115154-96-6 N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine 
• 115154-97-7 N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine 
• 115154-99-9 N-methylthiomethyl-N'-t-butyl-N,N'-dibenzoylhydrazine 
• 115154-98-8 N-methoxymethyl-N'-t-butyl-N-N'-dibenzoylhydrazine 
• 65715-09-5 2-phenyl-3-benzoyl-1,3,4-oxadiazole-2-(3H)-thione 

Relevant articles and documents

Synthesis and insecticidal evaluation of novel N-(S-amino)sulfenylated derivatives of diacylhydrazines

A series of new N-(S-amino)sulfenylated derivatives of diacylhydrazines were synthesized by the reaction of S-aminosulfenyl chlorides with N-tert-butyl-N′-benzoyl-N-substituted benzoylhydrazines in the presence of sodium hydride, and evaluated for moulting hormone mimicking activity. In the course of syntheses, N - N bond cleavage in diacylhydrazines was found and the reaction was studied in some detail. The results of bioassay showed that the title compounds exhibit excellent larvicidal activity. Toxicity assays indicated that these compounds can induce a premature, abnormal and lethal larval mount.

A novel convenient synthesis of 1,3,4-oxadiazol-2-ones and -thiones from N-tert-butyldiacylhydrazines

An attractive, novel, convenient process for the preparation of 3,5-disubstituted-3H-[1,3,4]-oxadiazol-2-ones and -thiones from the reaction of various equivalent and non-equivalent N-tertbutyldiacylhydrazines with potassium tert-butoxide followed by treatment with phosgene or thiophosgene, respectively, has been discovered. The 3,5-disubstituted-3H-[1,3,4]-oxadiazol-2-ones and -thiones are confirmed both analytically and chemically. Various equivalent and non-equivalent N-tert-butyldiacylhydrazines are conveniently synthesized from the reaction of tert-butylhydrazine hydrochloride in the presence of i-Pr2NEt, with acid chloride #1 followed by subsequent treatment with acid chloride #2. Both the syntheses of 3,5-disubstituted-3H-[1,3,4]-oxadiazol-2-ones and -thiones, as well as N-tert-butyldiacylhydrazines, are easily performed on multigram scales.

N′-tert-butyl-N′-aroyl-N-(alkoxycarbonylmethyl)-N- aroylhydrazines, a novel nonsteroidal ecdysone agonist: Syntheses, insecticidal activity, conformational, and crystal structure analysis

Seventeen N′-tert-butyl-N′-aroyl-N-(alkoxycarbonylmethyl)-N-aroylhydrazines were synthesized, and their insecticidal activities against armyworm (Leucania separata (Walker)) were tested. The conformation and structure of compound 1b was studied by 1H NMR spectroscopy and X-ray crystallography. The crystal structure belongs to the orthorhombic system and the N-N bond adopts a gauche conformation, which was assumed to be the active conformation, with a dihedral angle of 69.9°.

Synthesis and biological activity of novel N-sulfenylated derivatives of diacylhydrazines

A series of new N-sulfenylated derivatives of diacylhydrazines were synthesised and evaluated for moulting hormone mimicking activity, and the results of bioassay showed that the title compounds exhibit excellent larvicidal activities, and toxicity assays

Insecticidal N'-substituted-N,N'-disubstitutedhydrazines

This invention relates to N'-substituted-N,N'-disubstitutedhydrazines of formula I wherein X and X' are independently O, S, or NR; A' and B' are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is alkyl, alkenyl, or aralkyl; and wherein E is a tertiary carbon containing organic radical having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen which are useful as insecticides, compositions containing those compounds, methods of producing the compounds, and methods of their use. More particularly, the invention relates to insect growth regulating compounds and compositions, and methods of using such compounds and compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.

Preparation of 1,2-diacyl-2-(t-alkyl)hydrazines

The present invention provides a process for preparing 1,2-diacyl-2-(t-alkyl)hydrazines. More particularly, the present invention a process for preparing the aforesaid diacylhydrazines utilizing a solvent comprising an ester or a mixture of an ester and water in a process wherein an aromatic acid chloride is reacted in a first step with a t-alkylhydrazine or a corresponding acid addition salt of a t-alkylhydrazine such as the hydrochloride salt in the presence of a base to afford a 1-acyl-2-t-alkylhydrazine followed by a second step wherein an aromatic acid chloride is reacted with the aforesaid monoacylhydrazine in the presence of a base to afford the desired 1,2-diacyl-2-(t-alkyl)hydrazine. Such compounds are known to have excellent insecticidal activity against insects of the orders Lepidoptera and Coleoptera.

Turfgrass insecticides

This invention relates to a method of controlling insects in turfgrass, ornamental plants or food crops using an insecticidally effective amount of certain N'- substituted-N,N'-diacylhydrazines having the formula STR1 wherein X is phenyl, 2-fluorophenyl, or phenyl or 2-fluorophenyl substituted at the 4-position with chloro, fluoro, iodo, methyl or ethyl and Y is phenyl, 4-fluorophenyl, 2-chloro-4-fluorophenyl or phenyl substituted at the 2-position with chloro, bromo or iodo.

Insecticidal N'-substituted-N,N'-diacylhydrazines

This invention relates to insecticidal compositions containing N'-substituted-N,N'-diacylhydrazines, methods of using such compositions and certain novel insecticidal N'-substituted-N,N'-diacylhydrazines.

The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine, a nonsteroidal ecdysone agonist, and its effects on spruce budworm (Choristoneura fumiferana)

The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine (1), a nonsteroidal ecdysone agonist, has been established by direct methods and refined to a final R value of 0.038 for 2502 observed reflections.The crystals belong to the monoclinic system, a