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That Are N O Ttuurito THAT AREN O US009802899B2TTUURITO ( 12) United States Patent (10 ) Patent No. : US 9 ,802 , 899 B2 Heilmann et al. ( 45 ) Date of Patent: Oct . 31, 2017 ( 54 ) HETEROCYCLIC COMPOUNDS AS CO7D 401/ 12 ( 2006 .01 ) PESTICIDES C07D 403 /04 (2006 .01 ) CO7D 405 / 12 (2006 . 01) (71 ) Applicant : BAYER CROPSCIENCE AG , C07D 409 / 12 ( 2006 .01 ) Monheim (DE ) C070 417 / 12 (2006 . 01) (72 ) Inventors: Eike Kevin Heilmann , Duesseldorf AOIN 43 /60 ( 2006 .01 ) (DE ) ; Joerg Greul , Leverkusen (DE ) ; AOIN 43 /653 (2006 . 01 ) Axel Trautwein , Duesseldorf (DE ) ; C07D 249 /06 ( 2006 . 01 ) Hans- Georg Schwarz , Dorsten (DE ) ; (52 ) U . S . CI. Isabelle Adelt , Haan (DE ) ; Roland CPC . .. C07D 231/ 40 (2013 . 01 ) ; AOIN 43 / 56 Andree , Langenfeld (DE ) ; Peter ( 2013 .01 ) ; A01N 43 /58 ( 2013 . 01 ) ; AOIN Luemmen , Idstein (DE ) ; Maike Hink , 43 /60 (2013 .01 ) ; AOIN 43 /647 ( 2013 .01 ) ; Markgroeningen (DE ); Martin AOIN 43 /653 ( 2013 .01 ) ; AOIN 43 / 76 Adamczewski , Cologne (DE ) ; Mark ( 2013 .01 ) ; A01N 43 / 78 ( 2013 .01 ) ; A01N Drewes, Langenfeld ( DE ) ; Angela 43/ 82 ( 2013 .01 ) ; C07D 231/ 06 (2013 . 01 ) ; Becker , Duesseldorf (DE ) ; Arnd C07D 231 /22 ( 2013 .01 ) ; C07D 231/ 52 Voerste , Cologne (DE ) ; Ulrich ( 2013 .01 ) ; C07D 231/ 56 (2013 .01 ) ; C07D Goergens, Ratingen (DE ) ; Kerstin Ilg , 249 /06 (2013 . 01 ) ; C07D 401 /04 ( 2013 .01 ) ; Cologne (DE ) ; Johannes -Rudolf CO7D 401/ 12 ( 2013 . 01) ; C07D 403 / 04 Jansen , Monheim (DE ) ; Daniela Portz , (2013 . 01 ) ; C07D 403 / 12 ( 2013 . 01) ; C07D Vettweiss (DE ) 405 / 12 ( 2013 .01 ) ; C07D 409 / 12 ( 2013 .01 ) ; C07D 417 / 12 ( 2013 .01 ) ( 73 ) Assignee : BAYER CROPSCIENCE AG , (58 ) Field of Classification Search Monheim ( DE ) ??? . .. .. C07D 231/ 40 USPC . .. .. .. .. .. .. .. 548 / 371 . 7 , 372 . 5 ; 514 /407 ( * ) Notice : Subject to any disclaimer , the term of this See application file for complete search history . patent is extended or adjusted under 35 U . S .C . 154 (b ) by 0 days . ( 56 ) References Cited (21 ) Appl. No. : 14 /432 , 501 U . S . PATENT DOCUMENTS 4 ,435 ,503 A 3 / 1984 Mihayashi et al. ( 22 ) PCT Filed : Sep . 30, 2013 4 ,663 ,272 A 5 / 1987 Nakamura et al . 5 , 518 , 891 A 5 / 1996 Gibboni et al. ( 86 ) PCT No10 .: PCT/ EP2013 / 070371 5 ,624 , 941 A 4 / 1997 Barth et al. 6 , 124 , 334 A 9 / 2000 Hutchinson $ 371 ( c )( 1 ) , 8 ,791 , 139 B2 7 /2014 Fischer et al. ( 2 ) Date : Mar. 31, 2015 ( Continued ) ( 87 ) PCT Pub . No. : WO2014 / 053450 FOREIGN PATENT DOCUMENTS PCT Pub . Date : Apr. 10 , 2014 DE 3226163 A1 1 / 1983 (65 ) Prior Publication Data DE 159875 Al 4 / 1983 US 2015 /0239847 A1 Aug. 27 , 2015 (Continued ) (30 ) Foreign Application Priority Data OTHER PUBLICATIONS Opposition of Costa Rica Patent No . 2015 -0182 , filed Aug. 12 , Oct. 2 , 2012 (EP ) . .. .. 12186946 Jun . 5 , 2013 (EP ) 2015 , and English translation thereof. .. .. .. .. .. .. 13170565 (Continued ) (51 ) Int. Cl. CO7D 231/ 40 ( 2006 .01 ) Primary Examiner — Patricia L Morris AOIN 43 /56 ( 2006 .01 ) ( 74 ) Attorney , Agent, or Firm — McBee Moore AOIN 43 /58 ( 2006 .01 ) Woodward & Vanik IP, LLC ; Susan McBee ; David A01N 43 /647 ( 2006 . 01 ) Woodward AOIN 43 / 76 ( 2006 . 01 ) AOIN 43 / 78 ( 2006 .01 ) (57 ) ABSTRACT AOIN 43 /82 ( 2006 . 01) The present application relates to the use of heterocyclic C07D 231 /52 ( 2006 .01 ) compounds for controlling animal pests including arthro C07D 231/ 56 (2006 .01 ) pods , insects and nematodes , to novel heterocyclic com C07D 403 / 12 ( 2006 . 01 ) pounds , to processes for their preparation and to intermedi C07D 231 /06 ( 2006 . 01 ) ates for preparing the heterocyclic compounds. CO7D 231 / 22 ( 2006 .01 ) CO7D 401/ 04 ( 2006 .01 ) 27 Claims, No Drawings US 9 ,802 , 899 B2 Page 2 References Cited WO 2007030567 A2 3 / 2007 ( 56 ) WO 2007037543 A1 4 / 2007 U . S . PATENT DOCUMENTS WO 2007039146 Al 4 / 2007 WO 2007073297 A1 6 / 2007 8 , 809 ,547 B2 8 / 2014 Bretschneider et al. WO 2007093829 Al 8 / 2007 2002 /0042501 A1 4 / 2002 Zhang et al . WO 2008126899 Al 10 / 2008 2004 /0006047 AL 1 / 2004 Schaper et al . Wo 2009011850 A2 1 / 2009 2004 / 0039037 A1 wo 2009077766 A1 6 / 2009 2 / 2004 Zhang et al . wo 2009099670 A2 8 / 2009 2004 /0220170 A1 11/ 2004 Atkinson et al . WO 2990100438 A2 8 / 2009 2005 /0020564 A1 1 / 2005 Atkinson et al . WO 2010005692 A2 1 / 2010 2008 /0090810 AL 4 / 2008 Shia et al. WO 2010006713 A2 1 / 2010 2011/ 0152332 A1 6 / 2011 Murata et al. WO 2011020883 A9 2 / 2011 2013 /0261141 A1 10 / 2013 Bretschneider et al. WO 2011051455 Al 5 / 2011 2013 / 0338367 AL 12 / 2013 Numata et al . WO 2011157654 Al 12 / 2011 2015/ 0239847 AL 8 / 2015 Heilmann et al . WO 2012052412 A1 4 / 2012 WO 2012061290 A2 5 / 2012 FOREIGN PATENT DOCUMENTS WO 2012071519 A1 5 / 2012 WO 2012078593 A2 6 / 2012 DE 4343454 A 6 / 1995 wo 2012108511 A1 8 / 2012 DE 102008041216 A1 2 / 2010 WO 2013082324 Al 6 / 2013 EP 0022578 A1 1 / 1981 WO 2013173218 A1 11 / 2013 ?? 0420803 A2 4 / 1991 wo 2014053450 A14 /2014 EP 0591103 A1 9 / 1992 WO 2014064229 Al 5 / 2014 EP 0576357 B1 3 / 1997 WO 2015105129 Al 7 / 2015 0974337 B1 3 / 2001 wo 2015144652 A2 10 / 2015 S5810738 A 1 / 1983 WO 2015144683 A 10 / 2015 60218646 A 11 / 1985 WO 2015150252 Al 10 /2015 S60218646 A 11 / 1985 S -6142652 A 3 / 1986 52090657 A2 4 / 1987 OTHER PUBLICATIONS 7188269 A 7 / 1995 International Search Report from corresponding PCT/ EP2013 / Seeeeeee 11302177 A 11 / 1999 2003221535 A 8 / 2003 070371 , dated Nov . 18 , 2013 . 2005504105 A 2 / 2005 European Search Report from corresponding EP 12 18 6946 , dated 200745752 A 2 / 2007 Mar . 13 , 2013 . 2010202648 A 9 /2010 Research Disclosure , dated May 1980 , pp . 165 - 167 . 2010202648 A2 9 /2010 XP - 002692791, 1 / 1 — ( c ) File Registry, STN GEN Caesar accession JP 2010202649 A2 9 / 2010 No . 1392 , Feb . 26 , 2013 , pp . 1 - 4 . WO 199803475 A1 1 / 1998 XP - 002692793 , 1 / 1 — ( c ) File Regitry, STN GEN Caesar accession WO 9828269 A1 7 / 1998 No . 1394 , Feb . 26 , 2013 , pp . 1 - 6 . WO 9857937 A2 12 / 1998 XP -002692749 , 1 / 1 ( C ) File Registry STN GEN Caesar accession WO 9932454 A1 7 / 1999 No. 1396 , Feb . 26 , 2013 , pp . 1 - 4 . WO 01062737 A2 8 / 2001 XP -002692801 , 1 / 1 ( C ) File Registry STN GEN Caesar accession wo 03074550 A2 9 /2003 No. 1393 , Feb . 26 , 2013, pp . 1 - 4 . WO 2004089303 A2 10 / 2004 Matysiak et al ., “ Synthesis and Antimycotic Activity of N - azolyl- 2 , WO 2004089306 A2 10 / 2004 4 - dihydroxythiobenzamides” , Science Direct , Bioorganic & WO 2005092863 A1 10 / 2005 WO 2006033005 A2 3 / 2006 Medicinal Chemistry 11 (2003 ) pp . 2285 - 2291, XP -055054430 . WO 2008026965 A1 3 / 2006 XP - 55054696 , Ambinter - Chemical compounds , Amb10178766 , 1 WO 2006056433 A2 6 / 2006 page . WO 2006102758 Al 10 / 2006 Database Registry [online ] Chemical Abstract Service, US; Jul . 29 , WO 2006130403 Al 12 /2006 2009 (Jul . 29 , 2009 ) , Retrieved from STNODatabase accession No . WO 2007002248 A2 1 / 2007 RN 1170047 - 96 - 7 ; N - [ 1 - ( 2 , 4 -difluorophenyl ) - 5 -methyl - 1H WO 2007017125 A1 2 / 2007 pyrazol- 3 - yl )- 2 , 4 - dimethoxybenzamide . (cited in ISR ). US 9 , 802, 899 B2 HETEROCYCLIC COMPOUNDS AS PESTICIDES CROSS REFERENCE TO RELATED W - 1 ethyl 2 - (trifluoromethyl ) phenyl a5 APPLICATIONS W - 2 ethyl 2 -bromophenyl This application is a $ 371 National Stage Application of W - 3 ethyl 2 - fluorophenyl PCT/ EP2013 /070371 , filed 30 Sep . 2013 , which claims W - 4 ethyl 3 -methyl - 2 -thienyl priority to EP 12186946 . 5 , filed 2 Oct . 2012 and EP W - 5 ethyl 2 ,5 -dimethyl - 3 - furanyl 13170565 . 9 , filed 5 Jun . 2013 . 10 W - 6 H 2 , 4 -dimethoxyphenyl W - 7 2 - (trifluoromethyl ) phenyl BACKGROUND W - 8 2 ,4 - difluorophenyl W - 9 methyl 2 - bromophenyl Field of the Invention 15 W - 10 ethyl 2 ,4 -difluorophenyl The present application relates to the use of heterocyclic W - 11 ? 2 ,5 - dimethyl - 3 - furanyl compounds for controlling animal pests including arthro W - 12 methyl 2 ,4 - dimethoxyphenyl pods , insects and nematodes , to novel heterocyclic com pounds, to processes for their preparation and to intermedi- 20 ates for preparing the heterocyclic compounds. (W2 ) Description of Related Art H E The heterocyclic compounds of the formulae ( W ) and 25 (W2 ) are known ( cf . for the compounds of the formula ( W ) Registry Numbers 1189645 -25 - 7 , 1189474 - 83 - 6 , 1193202 69 - 5 , 1172407 -07 - 6 , 1185158 - 40 - 0 , 1185036 - 12 - 7 , 1170986 -74 - 9 , 1193179 - 17 - 7 , 1189458 -68 - 1 , 1189956 - 23 - 20 Aryl 7 , 1189915 - 26 - 1 , 1170047 - 96 - 7 ) . A use of these compounds has not been described . No . CAS- No. Reference Z E aryl W2- 1 74202 - 18 - 9 Research 0 2 -nitrophenyl 3 , 4 -dichloro - 2 ,5 Disclosure 1980 , dimethoxyphenyl 193011, 165 .) W2- 2 612092- 81 - 6 Bioorg. Med . S 2 , 4 -dihydroxyphenyl 2 , 4 ,6 -trichlorophenyl Chem . 2003, 2285 . W2- 3 111243 - 44 - 8 JP 62 -090657 O 2 - chloro - 4 - aminophenyl 2 , 4 , 6 - trichlorophenyl W2 - 4 101750 - 33 - 8 JP 60 - 218646 2 - chloro - 5 2 , 4 , 6 - trichlorophenyl ( acryloylamino ) phenyl W2- 5 87756 - 39 - 6 DE 3226163 2 - chloro - 5 -aminophenyl 2 , 4 , 6 -trichlorophenyl W2- 6 87756 - 30 - 7 DD 159875 0 2 - chloro - 5 - nitrophenyl 2 , 4 , 6 - trichlorophenyl W2- 7 86025 - 05 - 0 DE 3226163 2 -chloro - 5 2 ,4 ,6 - trichlorophenyl ????? (methacryloylamino ) phenyl 50 Derivatives of pyrazole - 4 - carboxamides are known from JP 2010 - 202649 . The compounds described therein have bactericidal action against plant - damaging bacteria . Inter mediates for their preparation are described in JP 2010 202648 .
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