CHA KUNA TA VE US010029986B2KATLAMAT DITUTTON (12 ) United States Patent ( 10 ) Patent No. : US 10 , 029 ,986 B2 Mita et al. (45 ) Date of Patent : Jul . 24 , 2018 ( 54 ) ALKYNYL PYRIDINE - SUBSTITUTED AMIDE FOREIGN PATENT DOCUMENTS COMPOUND AND PESTICIDE EP 2 218 717 AL 8 /2010 JP 2006 - 528613 A 12 / 2006 @( 71 ) Applicant: NISSAN CHEMICAL INDUSTRIES , JP LTD ., Chiyoda - ku ( JP ) (Continued ) @( 72 ) Inventors : Takeshi Mita , Funabashi ( JP ) ; OTHER PUBLICATIONS Motoyoshi Iwasa , Funabashi ( JP ) ; Yusuke Nanjo , Funabashi ( JP ) ; Taichi International Search Report dated Apr . 28 , 2015 in PCT/ JP2015 / Shimomiya , Funabashi ( JP ) ; Hidehito 054439 Filed Feb . 18 , 2015 . Kuwahara , Shiraoka ( JP ) ; Hotaka Primary Examiner - Daniel R Carcanague Imanaka , Shiraoka ( JP ) ( 74 ) Attorney , Agent, or Firm — Oblon , McClelland , @( 73 ) Assignee : Nissan Chemical Industries , Ltd ., Maier & Neustadt, L . L . P . Chiyoda - ku ( JP ) ( 57 ) ABSTRACT @ Subject to any disclaimer, the term of this Provided is a novel pesticide, particularly a fungicide and a ( * ) Notice : nematicide . An alkynyl pyridine - substituted amide com patent is extended or adjusted under 35 pound represented by formula ( I ) , its N -oxide or a salt U . S . C . 154 ( b ) by 0 days . thereof , and a pesticide containing it . [ In the formula , Gl is a structure represented by G ? - 1a , G -3a , G²- 27a , etc . ; Xl is ( 21 ) Appl. No .: 15 /119 ,660 a halogen atom , difluoromethyl, trifluoromethyl , etc . ; Yl is @ a halogen atom , etc .; Y , Yº, R4 and R independently ( 22 ) PCT Filed : Feb . 18 , 2015 represent a hydrogen atom , etc . ; R ' is a hydrogen atom , a halogen atom , methyl, methoxy , etc . ; R2 is a hydrogen atom , PCT / JP2015 / 054439 a halogen atom , etc . , or R and R2 together form an alkylene ( 86 ) PCT No. : chain thereby to form a cyclopropyl group together with the § 371 (c )( 1 ), carbon atom to which R and R2 are bonded , or R and R2 ( 2 ) Date : Aug . 17 , 2016 together form C , -C2 alkylidene or C , -C2 haloalkylidene ; R3 is a hydrogen atom , methyl, etc . , and Rº is C1 - C4 alkyl, (87 ) PCT Pub . No .: W02015 /125824 Cz -Co cycloalkyl, C , -C4 alkoxy (C1 - C4) alkyl, etc . ] PCT Pub . Date : Aug . 27 , 2015 Gl- la (65 ) Prior Publication Data US 2017 /0008847 A1 Jan . 12 , 2017 ( 30 ) Foreign Application Priority Data Feb . 18 , 2014 ( JP ) .. .. .. 2014 -028087 Apr. 11, 2014 ( JP ) .. .. .. .. .. 2014 - 082159 G !- 3a (Continued ) pa (51 ) Int. CI. CO7D 213 /61 ( 2006 .01 ) CO7D 401 / 12 ( 2006 .01 ) G1- 27a ( Continued ) (52 ) U . S . CI. CPC . .. .. .. .. CO7D 213 /61 ( 2013 .01 ) ; A01N 43 / 40 ( 2013 .01 ) ; A01N 43 /56 ( 2013 .01 ) ; A01N 43760 (2013 . 01 ) ; (Continued ) ( 58 ) Field of Classification Search (1) ??? . .. .. CO7D 231/ 14 R6 (Continued ) O R3 R4 Y ERO ( 56 ) References Cited U . S . PATENT DOCUMENTS NXX My R1 R2 2006 /0246102 AL 11/ 2006 Mansfield et al. ogR5 2007 /0167491 A1 7 / 2007 Mansfield et al . ( Continued ) 12 Claims, No Drawings US 10 ,029 , 986 B2 Page 2 ( 30 ) Foreign Application Priority Data 2014 / 0088157 A1 3 / 2014 Kita et al . 2015 /0259322 AL 9 /2015 Kita et al . Apr. 22 , 2014 ( JP ) .. 2014 - 088408 2015 / 0266853 AL 9 /2015 Kita et al . Jun . 25 , 2014 ( JP ) .. .. .. .. 2014 - 130395 FOREIGN PATENT DOCUMENTS Int. CI. (51 ) 2007 -526279 A 9 /2007 CO7D 409 / 12 ( 2006 .01 ) ese 2009 - 539791 A 11 /2009 C07D 411 / 12 ( 2006 . 01 ) 2010 - 529971 A 9 /2010 CO7D 417 / 12 ( 2006 .01 ) 2013 - 528613 A 7 / 2013 AOIN 43 /40 ( 2006 . 01 ) 2017039722 * 2 / 2017 AOIN 43 / 56 WO 2004 /016088 A2 2 / 2004 ( 2006 .01 ) WO 2004 /074280 All 9 / 2004 A01N 43 /60 ( 2006 . 01) WO 2005 / 014545 A2 2 / 2005 AOIN 43 / 78 ( 2006 .01 ) WO 2005 /016876 A2 2 / 2005 A61K 45 / 06 ( 2006 . 01 ) WO 2005 /058828 A1 6 / 2005 C07D 401/ 06 ( 2006 .01 ) wo 2005 /058833 A1 6 / 2005 WO 2005 /085238 Al 9 / 2005 AOIN 43 / 84 ( 2006 . 01 ) WO WO 2006 / 122952 AL 11 / 2006 A01N 55 / 00 ( 2006 .01 ) WO WO 2006 / 122955 AL 11 / 2006 ( 52 ) U . S . CI. WO 2007 / 108483 AL 9 / 2007 ??? . .. .. .. .. AOIN 43 / 78 ( 2013 . 01 ) ; AOIN 43 / 84 WO 2007 / 141009 A1 12 / 2007 WO WO 2007 / 141473 Al 12 / 2007 ( 2013. 01 ) ; A01N 55 / 00 ( 2013 .01 ) ; A61K 45/ 06 WO WO 2008 /093065 AL 8 / 2008 (2013 .01 ) ; C07D 401 / 06 ( 2013 .01 ) ; C07D WO 2008 / 151828 A2 12 / 2008 401/ 12 (2013 .01 ) ; C07D 409 / 12 (2013 .01 ) ; wo 2011 / 151369 Al 12 / 2011 C07D 411/ 12 ( 2013 .01 ) ; C07D 417 / 12 WO WO 2011 / 151370 AL 12 / 2011 WO 2012 / 028676 A1 3 /2012 (2013 .01 ) WO WO 2012 /052489 A1 4 /2012 (58 ) Field of Classification Search WO WO 2012 /052491 A2 4 /2012 USPC . .. .. 546 /275 . 4 WO WO 2012 / 118139 A1 9 / 2012 See application file for complete search history . WO WO 2013 /064460 Al 5 / 2013 WO WO 2013 / 064461 A2 5 / 2013 ( 56 ) References Cited Wo WO 2013 / 120940 A2 8 / 2013 WO 2014 /010737 A1 1 /2014 U . S . PATENT DOCUMENTS WO WO 2014 /034750 A13 /2014 WO WO 2014 / 034751 A13 / 2014 2010 / 0222389 AL 9 /2010 Walter et al . WO 2014 / 173921 A1 10 / 2014 2011/ 0136831 A1 6 / 2011 Oda et al . WO W O 2018003924 * 1 /2018 2011/ 0207771 AL 8 /2011 Stierli et al . 2013/ 0131119 Al 5 / 2013 Benting et al. * cited by examiner US 10 ,029 , 986 B2 ALKYNYL PYRIDINE - SUBSTITUTED AMIDE Patent Document 6 : WO2005 /014545 COMPOUND AND PESTICIDE Patent Document 7 : WO2005 /058828 Patent Document 8 : WO2005 /058833 TECHNICAL FIELD Patent Document 9 : WO2005 /085238 5 Patent Document 10 : WO2007 / 108483 The present invention relates to a novel alkynyl pyridine Patent Document 11 : EP2218717 substituted amide compound, its N - oxide or a salt thereof, Patent Document 12 : WO2011/ 151369 and a pesticide containing it as an active ingredient. DISCLOSURE OF INVENTION BACKGROUND ART 10 Technical Problem Heretofore, with respect to alkynyl pyridine -substituted amide compounds, for example , N - [ [ 1 - [ 3 -chloro - 5 - ( 3 , 3 , 3 Infection or parasitism of pests such as pathogens and trifluoro - 1 -propynyl ) pyridin - 2 - yl] cyclopropyl] methyl ] - 3 - parasites causes, in a case where the hosts are plants such as fluoropyridine- 2 - carboxamide , N - [[ 1 - [ 3 -chloro - 5 - ( 3 , 3 , 3 - tri- 15 grain , fruits , vegetables or ornamental plants , a decrease in fluoro - 1 -propynyl ) pyridin - 2 - yl] cyclopropyl ]methyl ] - 3 the quality of agricultural crops and a remarkable decrease chloropyridine - 2 - carboxamide , N - [ [ 1 - [ 3 - chloro - 5 - ( 3 , 3 , 3 - in the yield , and in some cases , serious damages such as trifluoro - 1 -propynyl ) pyridin - 2 - yl ] cyclopropyl ]methyl ] - 3 - death of the plants , and inflicts heavy economic losses not methylpyridine - 2 - carboxamide and N - [ [ 1 - [ 3 - chloro - 5 - ( 3 , 3 , only on the producers but also on the consumers . Thus, to 3 - trifluoro - 1 -propynyl ) pyridin - 2 -yl ] cyclopropyl ] methyl ] - 3 - 20 effectively control such pests is a very important object to ( trifluoromethyl) pyridine - 2 - carboxamide are known to achieve efficient and stable production of agricultural crops . show nematicidal activities (see Patent Document 1 ) ; N - [ 2 - Further , in a case where the hosts are animals such as [ 5 - (4 - ethoxyphenylethynyl) pyridin - 2 - yl ] ethyl ] acetamide is companion creatures /pets or livestock /poultry , to effectively known to have an acetyl COA carboxylase inhibitory activity control such pests is an important object also for the purpose ( see Patent Document 2 ) ; and as an intermediate for pro - 25 ofmaintaining health of the target animals and further , in a ducing BACE - 1 inhibitors , N - [ 1 - ( S ) - [ ( 3 , 5 - difluorophenyl) case where the target animals are livestock or poultry , for the methyl] - 2 - [ 5 - ( 3 - fluorophenylethynyl) pyridin - 2 -yl ) - 2 - (hy - purpose of stably producing safe food or high quality droxylethyl ) - 3 - ( N , N - di ( normal propyl ) carbamoyl) - 5 - general merchandise such as wool, feathers or leathers . methylbenzamide is known (see Patent Document 3 ) . From such a viewpoint , heretofore , development of pesti Further with respect to pyridine - substituted amide com - 30 cides targeted at pathogens or parasites has advanced , and pounds, for example , N - [ 2 - [ 3 - chloro - 5 - ( trifluoromethyl) various effective pesticides have been put into practical use . pyridin - 2 - yllethyl) - 2 - ( trifluoromethyl) benzamide ( see Pat- However , recently , control of pests with conventional ent Document 4 ), N - [ 2 - [ 3 - chloro - 5 - ( trifluoromethyl) pesticides has become difficult in more and more cases , as pyridin - 2 - yl] ethyl] - 3 - difluoromethyl - 1 -methyl - 1H pathogens or parasites acquire resistance to them over many pyrazole - 4 - carboxamide ( see Patent Document 5 ) , N - [ 2 - ( 3 , 35 years of their use . Problems of the high toxicity of some 5 - dichloropyridin - 2 - yl ) ethyl) - 2 - ( trifluoromethyl) benzamide conventional pesticides and of the disturbance of the eco (see Patent Document 6 ) , N - [ 2 - [ 3 - chloro - 5 - ( trifluorom system by some conventional pesticides which remain in the ethyl )pyridin - 2 -yl ] - 1 -methylethyl ] - 2 - ( trifluoromethyl ) benz - environment for a long period are becoming apparent. Under amide ( see Patent Document 7 ) , N - [ 2 - 13 - chloro - 6 - ( trifluo - these circumstances , development of novel pesticides not romethyl) pyridin - 2 - yl] butyl ] - 3 -difluoromethyl - 1 -methyl - 40 only having excellent pesticidal activity on pathogens and 1H -pyrazole - 4 -carboxamide (see Patent Document 8 ) , N - [ 2 - parasites but also having high