|MO NAMAN ATT VI US009924719B2LO HAMA WA MATAI (12 ) United States Patent ( 10 ) Patent No. : US 9 , 924 ,719 B2 Tanabe et al. ( 45 ) Date of Patent: Mar . 27, 2018 ( 54 ) PYRIDAZINE COMPOUND 200139954 2 / 2001 2003313169 A 11 / 2003 (71 ) Applicant: Sumitomo Chemical Company, ?? 201360420 A 4 / 2013 Limited , Tokyo ( JP ) WO 2013027660 A1 2 / 2013 (72 ) Inventors: Takamasa Tanabe, Takarazuka (JP ) ; OTHER PUBLICATIONS Yoshihiko Nokura , Takarazuka ( JP ) ; Ryota Maehata , Takarazuka ( JP ) ; Vippagunta et al. ( 2001) . * Kohei Orimoto , Takarazuka ( JP ) ; Yuji Int ' l Preliminary Report on Patentability dated Apr . 4 , 2017 in Int 'l Nakajima , Takarazuka (JP ) Application No . PCT / JP2015 / 077420 . Int' l Search Report dated Dec. 22 , 2015 in Int' l Application No . (73 ) Assignee : SUMITOMO CHEMICAL PCT/ JP2015 /077420 . STN International, Benzenesulfonamide , N - ( 1 , 1 - dimethylethyl ) - 2 COMPANY, LIMITED , Tokyo ( JP ) [ 6 - ( 1 -methylethoxy ) - 3 -pyridazinyl ] -, File Registry [ online ] , entered ( * ) Notice : Subject to any disclaimer, the term of this STN : Jun 6 , 2014 , [ retrieved on Dec . 9 , 2015 ], CAS Registry No . patent is extended or adjusted under 35 1609752 - 12 - 6 . U . S . C . 154 (b ) by 0 days . * cited by examiner (21 ) Appl. No. : 15 /515 , 879 ( 22 ) PCT Filed : Sep . 29 , 2015 Primary Examiner — Paul V Ward ( 74 ) Attorney, Agent, or Firm — Panitch Schwarze ( 86 ) PCT No. : PCT/ JP2015 /077420 Belisario & Nadel LLP $ 371 ( c ) ( 1 ) , ( 2 ) Date : Mar. 30 , 2017 (57 ) ABSTRACT (87 ) PCT Pub. No. : WO2016 /052455 A pyridazine compound represented by formula ( 1 ) : PCT Pub . Date : Apr. 7 , 2016 (65 ) Prior Publication Data US 2017 /0295787 A1 Oct . 19 , 2017 ( 30 ) Foreign Application Priority Data 0 . N — N (R ) Oct. 3 , 2014 ( JP ) .. .. .. .. .. .. 2014 - 204515 R - 04 (51 ) Int. CI. CO7D 237/ 14 ( 2006 .01 ) AOIN 43 /58 ( 2006 .01 ) C07D 401 /04 ( 2006 . 01 ) (52 ) U .S . CI. wherein Arepresents a nitrogen atom or a CRO, R ' represents CPC .. AOIN 43/ 58 ( 2013. 01 ) ; CO7D 237/ 14 a C2 - C10 alkyl group having one or more halogen atoms , ( 2013 .01 ) ; C07D 401/ 04 (2013 .01 ) etc . , R2 and R * represent independently of each other a (58 ) Field of Classification Search hydrogen atom , etc ., R4 represents a C1 - C6 chain hydrocar ??? .. .. .. .. .. .. A01N 43 / 58 bon group optionally having one or more halogen atoms, RS See application file for complete search history . represents a C1 - C6 chain hydrocarbon group optionally having one or more halogen atoms, etc ., Rº represents a (56 ) References Cited hydrogen atom , etc . , n represents 0 , 1 , or 2 , and p represents 0 , 1 , or 2 , has an excellent efficacy for controlling harmful FOREIGN PATENT DOCUMENTS arthropods. S591469 A 1 / 1984 JE H1192456 A 4 / 1999 13 Claims, No Drawings US 9 , 924 ,719 B2 PYRIDAZINE COMPOUND more halogen atoms, a C2- C6 alkoxycarbonyl group , a cyano group , or a halogen atom ; CROSS -REFERENCE TO RELATED R4 represents a C1 - C6 chain hydrocarbon group option APPLICATION ally having one or more halogen atoms; 5 R represents a C1 - C6 chain hydrocarbon group option This application is a Section 371 of International Appli - ally having one or more halogen atoms, a phenyl group cation No. PCT/ / JP2015IP2015 /077420 , filedfiled SepSen . 2920 , 20152015 , which optionally having one or more atoms or groups selected from Group A , a 5 -membered aromatic heterocyclic group was published in the Japanese language on Apr. 7 , 2016 , selected from Group B (wherein said 5 -membered aromatic under International Publication No . WO 2016 / 052455herein A1by, 10 heterocyclic group may optionally have one or more atoms and the disclosure of which is incorporated herein by " or groups selected from Group A ), a 6 -membered aromatic reference . heterocyclic group selected from Group C (wherein said TECHNICAL FIELD 6 -membered aromatic heterocyclic group may optionally have one or more atoms or groups selected from Group A ), The present invention relates to a certain class of 15 a 3 to 7 membered nonaromatic heterocyclic group selected pyridazine compound and use of said compound for con from Group D ( wherein the 3 to 7 membered nonaromatic trolling harmful arthropods . heterocyclic group may optionally have one or more atoms or groups selected from the group consisting of a halogen BACKGROUND ART atom and a C1- C6 alkyl group ) , a OR ? , a NR?R " , a NRC 20 ( O )RO , a NR $ C ( O )OR , a NR $ C ( O ) NR12R13 , a To date , some compounds for controlling harmful arthro - N = CHNR ' R , a NGS ( O ) , R R " , a S ( O ) R " , a C ( O ) pods have been developed and come into practical use . OR®, a cyano group , or a halogen atom ; Also , a certain class of heterocyclic compound has been Rº represents a hydrogen atom , or a halogen atom ; R ' represents a hydrogen atom , a C1 -C6 alkyl group , a known ( see Patent Document 1 ) . 25 C3 - C6 alkenyl group , a C3 -C6 alkynyl group , a (C1 - C3 CITATION LIST alkyl) - 0 – ( C1- C3 alkyl) group , a ( C1- C3 alkyl) - S ( O ) , (C1 -C3 alkyl) group , a C3 - C7 cycloalkyl group , a (C3 - C7 Patent Document cycloalkyl) - (C1 - C3 alkyl ) group (wherein said C1 - C6 alkyl group , said C3 - C6 alkenyl group , said C3 - C6 alkynyl group , Patent Document 1 : JP 2003 - 313169 A 30 said (C1 - C3 alkyl) - 0 (C1 - C3 alkyl) group , said (C1 - C3 alkyl ) - S ( O ), — (C1 -C3 alkyl ) group , said C3 - C7 cycloalkyl SUMMARY OF THE INVENTION group , and said (C3 -C7 cycloalkyl) - (C1 - C3 alkyl) group may optionally have one or more halogen atoms) , or a Problems to be Solved By Invention phenyl C1 -C3 alkyl group (wherein the phenyl moiety in 35 saide phenyl C1- C3 alkyl group may optionally have one or An object of the present invention is to provide a com more atoms or groups selected from Group A ) ; pound having an excellent efficacy for controlling harmful R $ represents a hydrogen atom , a C1 - C6 alkyl group arthropods and a method for controlling harmful arthropods optionally having one or more halogen atoms, a C3 - C6 using said compound . alkenyl group optionally having one or more halogen atoms, 40 or a C3 - C6 alkynyl group optionally having one or more Means to Solve Problems halogen atoms; Rº represents a hydrogen atom , a C1 -C6 alkyl group , a [ 1 ] A piridazine compound represented by formula ( 1 ) : C3 - C6 alkenyl group , a C3 - C6 alkynyl group , a (C1 - C3 alkyl ) - 0 (C1 - C3 alkyl) group , a (C1 -C3 alkyl) - S ( O ), — 45 (C1 -C3 alkyl) group , a C3 -C7 cycloalkyl group , a (C3 - C7 ( 1) cycloalkyl) - (C1 - C3 alkyl ) group (wherein said C1- C6 alkyl group , said C3 - C6 alkenyl group , said C3 - C6 alkynyl group , said (C1 - C3 alkyl) - 0 — (C1 - C3 alkyl) group , said (C1 - C3 alkyl ) - S ( O ) , (C1 - C3 alkyl) group , said C3 - C7 cycloalkyl N — N ( Rº , 50 group , and said (C3 - C7 cycloalkyl ) - (C1 - C3 alkyl) group R1 - 04 may optionally have one or more halogen atoms) , a cyano C1 - C6 alkyl group , a phenyl C1- C3 alkyl group (wherein the phenyl moiety R2 R3 in said phenyl C1 -C3 alkyl group may optionally have one 55 or more atoms or groups selected from Group A ) , or wherein , a ( 5 or 6 membered heteroaryl) C1- C3 alkyl group A represents a nitrogen atom or a CR " ; (wherein the 5 or 6 membered heteroaryl moiety in said ( 5 R ! represents a C2 -C10 alkyl group , a C3 -C10 alkenyl or 6 membered heteroaryl) C1 -C3 alkyl group may option group , a C3 -C10 alkynyl group , a (C1 - C5 alkyl) - 0 (C2 - ally have one or more atoms or groups selected from Group C5 alkyl) group , a (C3 - C5 alkenyl) - 0 (C2 - C5 alkyl) 60 A ) ; group , a ( C3 - C5 alkynyl ) - 0 — (C2 -C5 alkyl) group , a (C1 - R1° represents a hydrogen atom , a C1 -C6 alkyl group , a C5 alkyl) - S ( O ) m ( C2 - C5 alkyl) group , a ( C3 - C5 alkenyl) - C3 -C6 alkenyl group , a C3 - C6 alkynyl group , a C3 - C7 S ( O ) m - ( C2 - C5 alkyl) group , a (C3 - C5 alkynyl) - S ( O ) m - cycloalkyl group , a (C3 - C7 cycloalkyl ) - (C1 - C3 alkyl) group ( C2 - C5 alkyl) group , or a (C1 - C5 alkyl) - C ( O ) - (C1 - C5 (wherein said C1 -C6 alkyl group , said C3 - C6 alkenyl group , alkyl ) group (wherein R ' has one or more halogen atoms) ; 65 said C3 -C6 alkynyl group , said C3 -C7 cycloalkyl group , and R2 and R² represent independently of each other a hydro - said (C3 -C7 cycloalkyl) - ( C1- C3 alkyl) group may option gen atom , a C1 - C6 alkyl group optionally having one or ally have one or more halogen atoms) , or a phenyl C1 -C3 US 9 , 924 ,719 B2 alkyl group (wherein the phenyl moiety in said phenyl -continued C1- C3 alkyl group may optionally have one or more atoms B - 8 or substituents selected from Group A ) ; R " represents a C1 - C6 alkyl group optionally having one or more halogen atoms, a C3 - C6 alkenyl group optionally 5 ZA having one or more halogen atoms, a C3 - C6 alkynyl group optionally having one or more halogen atoms, a C3 - C7 B - 9 cycloalkyl group optionally having one or more halogen atoms, a ( C3 -C7 cycloalkyl) - (C1 - C3 alkyl) group optionally having one or more halogen atoms (wherein said (C3 -C7 cycloalkyl) - ( C1- C3 alkyl ) group may optionally have one or 10 B - 10 more halogen atoms ), or a phenyl C1 - C3 alkyl group (wherein the phenyl moiety in said phenyl C1- C3 alkyl group may optionally have one or more atoms or groups selected from Group A ) ; Group C : R12 and R13 represent independently of each other a 15 C1 - C6 alkyl group optionally having one or more halogen C - 1 atomsato ; R14 represents a hydrogen atom , a C1 - C6 alkyl group optionally having