Michael B Ricks

US Patent:

54182476, May 23, 1995

Filed:

Oct 14, 1993

Appl. No.:

8/137312

Inventors:

Michael J. Ricks - Concord CA
Yulan C. Tong - Walnut Creek CA

Assignee:

DowElanco - Indianapolis IN

International Classification:

C07D41302
C07D41702
A01N 4372
A01N 4374

US Classification:

514365

Abstract:

3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-posit ion and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl is ocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.

US Patent:

41637879, Aug 7, 1979

Filed:

Dec 12, 1977

Appl. No.:

5/859908

Inventors:

Sudarshan K. Malhotra - Walnut Creek CA
Michael J. Ricks - Oakland CA

Assignee:

The Dow Chemical Company - Midland MI

International Classification:

A61K 3144
C07D21370
C07D21364

US Classification:

424263

Abstract:

Substituted pyridine methyl esters of cyclopropane carboxylic acids and the geometric and optical isomers thereof are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo. These compounds have been found to exhibit a high degree of insecticidal activity and compositions containing said compounds are so employed.

US Patent:

52505324, Oct 5, 1993

Filed:

Feb 27, 1992

Appl. No.:

7/842834

Inventors:

Kevin L. McLaren - Concord CA
Mark B. Hertlein - Pleasant Hill CA
James T. Pechacek - Clayton CA
Michael J. Ricks - Concord CA
Yulan C. Tong - Walnut Creek CA
Laura L. Karr - Pittsburg CA

Assignee:

DowElanco - Indianapolis IN

International Classification:

C07D40104
C07D40304
A01N 4356

US Classification:

514256

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.

US Patent:

54930243, Feb 20, 1996

Filed:

Jun 2, 1993

Appl. No.:

8/071870

Inventors:

Kevin L. McLaren - Concord CA
Mark B. Hertlein - Pleasant Hill CA
James T. Pechacek - Clayton CA
Michael J. Ricks - Concord CA
Yulan C. Tong - Walnut Creek CA

Assignee:

DowElanco - Indianapolis IN

International Classification:

C07D23704
C07D23924
C07D21512
C07D21172

US Classification:

544259

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-p yridinyl)-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.

US Patent:

53388569, Aug 16, 1994

Filed:

Aug 17, 1992

Appl. No.:

7/931098

Inventors:

Michael J. Ricks - Concord CA
Yulan C. Tong - Walnut Creek CA

Assignee:

DowElanco - Indianapolis IN

International Classification:

C07D27724
C07D26332

US Classification:

548204

Abstract:

3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamide compounds wherein the substituent in the 4-position is a 5-membered heterocyclic ring moiety containing one ring oxygen or sulfur atom and one or two ring nitrogen atoms and the substituents in the 3-position and the N-position are optionally substituted phenyl moieties, such as 4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethylphenyl)-4-(2-trifluorom ethyl-5-thiazolyl)-1H-pyrazole-1-carboxamide were prepared from appropriate 3,4-disubstituted-4,5-dihydro-1H-pyrazole compounds, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazo le and phenyl isocyanates and isothiocyanates, such as 4-(trifluoromethyl)phenyl isocyanate. The compounds are insecticidal.

US Patent:

42811333, Jul 28, 1981

Filed:

Nov 29, 1979

Appl. No.:

6/098464

Inventors:

Sudarshan K. Malhotra - Walnut Creek CA
Michael J. Ricks - Martinez CA

Assignee:

The Dow Chemical Company - Midland MI

International Classification:

C07D21348

US Classification:

546298

Abstract:

Substituted phenoxy and phenylthio picolinaldehydes are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2 and Y represents oxygen or sulfur. These compounds are employed as intermediates in the preparation of compounds which have a high degree of insecticidal activity.

US Patent:

42568935, Mar 17, 1981

Filed:

Mar 5, 1979

Appl. No.:

6/017752

Inventors:

Sudarshan K. Malhotra - Walnut Creek CA
Michael J. Ricks - Martinez CA

Assignee:

The Dow Chemical Company - Midland MI

International Classification:

C07D21364
C07D21370

US Classification:

546301

Abstract:

Substituted phenoxy and phenylthio pyridine methanols and substituted methanols are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur and R represents hydrogen, cyano or ethynyl. These compounds are employed as intermediates in the preparation of compounds which have a high degree of insecticidal activity.