3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides

US5250532A · kind A · utility

Assignee

• Dowelanco · US

Inventors

• Kevin L. McLaren · Carmel, US
• Mark B. Hertlein · Pleasant Hill, US
• James T. Pechacek · Clayton, US
• Michael J. Ricks · Concord, US
• Yulan C. Tong · Walnut Creek, US
• Laura L. Karr · Lebanon, US

Key dates

• Filing date: Feb 27, 1992
• Grant date: Oct 5, 1993
• Expiry date: Feb 27, 2012

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D403/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds having an aryl moiety in the 4-position that is an optionally substituted pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moiety and aryl moieties in the 3-position and the N-position that are optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moieties, such as N-(4-chlorophenyl)-4,5- -dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2- -pyridinyl)-1H-pyrazole-1-carboxamide, were prepared and found to possess insecticidal utility. 1,2-Diarylethanone compounds were converted to 1,2-diaryl-2-propen-1-one compounds by treatment with bis(dimethylamino)methane, the 1,2-diaryl-2-propen-1-one compounds were converted to 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds by treatment with hydrazine, and the 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds were converted to the insecticidal subject compounds by treatment with an aryl isocyanate.