- Efficient synthesis of bifenazate
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The synthesis of bifenazate using a two-step procedure has been accomplished with an overall yield of 26%. The procedure involved the Lewis acid-catalyzed electrophilic aromatic substitution of 4-methoxybiphenyl with diisopropyl azodicarcoxylate (DIAD) to give a hydrazinedicarboxylate intermediate that was then subjected to a decarboxylation reaction to give bifenazate. Copyright Taylor & Francis Group, LLC.
- Chee, Gaik-Lean
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- The discovery of bifenazate, a novel carbazate acaricide
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A history of the discovery of the novel carbazate acaricide, bifenazate, is outlined. When a novel ortho-biphenyl substituted hydrazide compound showed acaricidal activity in the pesticide discovery screen, a small number of analogs were made to confirm and explore acaricidal effects. An ortho-biphenylcarbazate analog gave significantly greater acaricidal activity. Thereafter, several hundred structurally-diverse biphenylsubstituted carbazate analogs were synthesized and evaluated in a bioassay with the two-spotted spider mite (Tetranychus urticae Koch) in order to optimize the acaricidal activity. As a result of the optimization process, bifenazate, the analog with a methoxybiphenyl substituent to the terminal nitrogen atom of isopropyl carbazate, was selected for development and registration.
- Dekeyser, Mark A.,McDonald, Paul T.,Angle Jr., Gilbert W.
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- Efficient and practical cross-coupling of arenediazonium tetrafluoroborate salts with boronic acids catalyzed by palladium(0)/barium carbonate
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The cross-coupling reaction of arenediazonium tetrafluoroborate salts with boronic acids catalyzed by the unusual palladium(0)/barium carbonate catalyst is described as an extremely practical and highly efficient alternative to classical homogeneous conditions. Reactions are conducted under mild conditions at room temperature without any base and ligand. The opportunity of preparing unsymmetrical terphenyls in a one-pot process is also demonstrated. Finally, the power of this methodology is highlighted by the synthesis of Bifenazate.
- Felpin, Francois-Xavier,Fouquet, Eric
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- Synthetic method for bifenazate
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The invention relates to a synthetic method for bifenazate. The method comprises the following specific synthetic sections: step 1, performing nitration: mixing a 4-hydroxybiphenyl solution and a toluene solution under stirring for a reaction, and adding a HNO3 solution dropwise for a reaction to obtain a nitration reaction solution; step 2, performing methylation: mixing the nitration reaction solution and anhydrous sodium carbonate powder for a reaction, and adding a dimethyl carbonate solution dropwise for a reaction to obtain a methylation reaction solution; step 3, performing hydrogenation: throwing the methylation reaction solution, hydrogen gas, and Raney nickel into a reaction kettle for a reaction to obtain a hydrogenation reaction liquid; step 4, performing hydrazination: performing a primary hydrazination reaction, performing a secondary hydrazination reaction, performing filter pressing, performing a tertiary hydrazination reaction, and performing secondary filter pressingto obtain a condensation reaction liquid; step 5, performing condensation: mixing a third hydrazine compound, an ethyl acetate solution and an isopropyl chloroformate solution for a reaction to obtaina bifenazate mixed liquid; and step 6, performing purification: performing desolvation, performing crystallization, performing centrifugation, performing washing, performing secondary centrifugation,and performing drying to obtain the finished bifenazate. The method provided by the invention has the effect of improving purity of the bifenazate product.
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- ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES
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The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.
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- Heterogeneous Pd/C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters
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Heterogeneous Pd/C-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl boronic esters with aryl bromides was successfully carried out in aqueous media at room temperature without the use of a ligand such as phosphine derivatives.
- Kitamura, Yoshiaki,Sakurai, Ai,Udzu, Takahiro,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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p. 10596 - 10602
(2008/02/12)
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- 4-methoxybiphenyl hydrazone derivatives
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Disclosed herein is a compound having the formula: wherein R1is alkyl and R2and R3are independently selected aryl groups. Also disclosed is a method of making bifenazate using the compound as an intermediate.
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Page column 9
(2010/02/05)
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- Active agent combinations
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The novel active compound combinations of extracts from seeds of the neem tree and the active compounds of groups (B) to (F) listed in the description have very good insecticidal and acaricidal properties.
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- 4-hydroxybiphenyl hydrazide derivatives
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Compounds having the formula: wherein R is hydrogen or CO2CH(CH3)2, useful as intermediates in the preparation of the miticide bifenazate, methods for their preparation, and methods for the preparation of bifenazate.
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