US 12,152,020 B2
Pesticidally active azole-amide compounds
Amandine Kolleth Krieger, Stein (CH); Andrew Edmunds, Stein (CH); Daniel Emery, Stein (CH); Julien Daniel Henri Gagnepain, Stein (CH); Jürgen Harry Schaetzer, Stein (CH); Thomas Pitterna, Stein (CH); and Sebastian Rendler, Stein (CH)
Assigned to SYNGENTA CROP PROTECTION AG, Basel (CH)
Appl. No. 17/290,556
Filed by SYNGENTA PARTICIPATIONS AG, Basel (CH)
PCT Filed Oct. 17, 2019, PCT No. PCT/EP2019/078302
§ 371(c)(1), (2) Date Apr. 30, 2021,
PCT Pub. No. WO2020/094363, PCT Pub. Date May 14, 2020.
Claims priority of application No. 18204422 (EP), filed on Nov. 5, 2018; and application No. 19156711 (EP), filed on Feb. 12, 2019.
Prior Publication US 2021/0403462 A1, Dec. 30, 2021
Int. Cl. C07D 413/14 (2006.01); A01N 43/653 (2006.01); A01N 43/82 (2006.01); C07D 403/04 (2006.01)
CPC C07D 413/14 (2013.01) [A01N 43/653 (2013.01); A01N 43/82 (2013.01); C07D 403/04 (2013.01)] 14 Claims
 
1. A compound of the formula I

OG Complex Work Unit Chemistry
wherein:
R1 is hydrogen, C1-C6alkyl, C1-C6cyanoalkyl, aminocarbonylC1-C6alkyl, hydroxycarbonylC1-C6alkyl, C1-C6nitroalkyl, trimethylsilaneC1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl; C3-C4cycloalkylC1-C2alkyl- wherein the C3-C4cycloalkyl is optionally substituted with 1 or 2 halo atoms; oxetan-3-yl-CH2—; or benzyl optionally substituted with halo or C1-C6haloalkyl;
R2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon C═O is attached, and each substituent is independently selected from: C1-C3alkyl, C1-C3haloalkyl, C1-C3thiohaloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, NO2, SF5, CN, CONH2, COOH and C(S)NH2;
R3 is C1-C3alkyl or C1-C3haloalkyl;
R4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one substituent selected from C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C4cycloalkyl, halogen or hydroxy;
Z1 is halogen, CN, NH2C(O), amino, (C1-C3alkyl)amino, di(C1-C3alkyl)amino, hydroxy, C3-C4halocycloalkyl, C3-C4cyanocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylsulfanyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy-C1-C3alkoxy, (C1-C3alkyl)sulfonylamino, (C1-C3alkyl)sulfonyl(C1-C3alkyl)amino, (C1-C3alkyl)NHC(O), (C1-C3alkyl)2NC(O), (C1-C3cycloalkyl)NHC(O), (C1-C3cycloalkyl)(C1-C3alkyl)NC(O), (C1-C3alkyl)C(O)(C1-C3alkyl)N, (C1-C3alkyl)C(O)NH, (C1-C3alkyl)C(O), HC(O), diphenylmethanimine, C1-C3haloalkoxy, phenyl or a 5-membered heteroaromatic ring wherein the phenyl or the 5-membered heteroaromatic ring is optionally substituted with one to three substituents selected from C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C4cycloalkyl, halogen, CN or hydroxy; or a stereoisomer, an enantiomer, a tautomer, an N-oxide, or an agrochemically acceptable salt thereof.