US 7,531,559 B2
Fungicidal 1,2,3 triazole derivatives
Josef Ehrenfreund, Basel (Switzerland); Hans Tobler, Basel (Switzerland); and Harald Walter, Basel (Switzerland)
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Appl. No. 10/524,721
PCT Filed Aug. 18, 2003, PCT No. PCT/EP03/09111
§ 371(c)(1), (2), (4) Date Feb. 16, 2005,
PCT Pub. No. WO2004/018438, PCT Pub. Date Mar. 04, 2004.
Claims priority of application No. 0219612.9 (GB), filed on Aug. 22, 2002; and application No. 0310464.3 (GB), filed on May 07, 2003.
Prior Publication US 2006/0154967 A1, Jul. 13, 2006
Int. Cl. A61K 31/41 (2006.01); C07D 249/00 (2006.01)
U.S. Cl. 514—359  [548/255] 7 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Drawing
where A is an ortho-substituted ring selected from formulae (A1) to (A22);

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
Q is a single or a double bond; X is O, N(R18), S or CR19R20)(CR21R22)m(CR23R24)n; R1 is halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy or optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl or optionally substituted SO2(C1-4)alkyl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C1-4alkoxy); R2 is C1-4alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl or C1-4 alkylthio(C1-4)alkyl or optionally substituted aryl (C1-4)alkyl- or [optionally substituted aryl]oxy(C1-4)alkyl- (where the optionally substituted aryl moieties may each have up to 3 substituents, each independently selected from halogen and C1-4 alkoxy); R3 is hydrogen, CH2C≡CR4, CH2CR4═C(H)R4, CH═C═CH2 or COR5 or optionally substituted C1-4alkyl, optionally substituted C1-4 alkoxy or optionally substituted (C1-4)alkylC(═O)O (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen, C1-4alkoxy, C1-4 alkyl, C1-2 haloalkoxy, hydroxy, cyano, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and ethylsulfonyl); each R4 is, independently, hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 alkoxy(C1-4)alkyl; R5 is hydrogen or optionally substituted C1-6 alkyl, optionally substituted C1-4 alkoxy, optionally substituted C1-4 alkoxy(C1-4)alkyl, optionally substituted C1-4 alkylthio(C1-4)alkyl or optionally substituted aryl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen, C1-6 alkoxy, C1-6 haloalkoxy, cyano, hydroxy, methoxycarbonyl and ethoxycarbonyl); R6 is
i) phenyl optionally substituted by up to 3 substituents, each independently selected from halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 haloalkylthio, C(H)═N—OH, C(H)═N—O(C1-6 alkyl), C(C1-6 alkyl)═N—OH, C(C1-6 alkyl)═N—O—(C1-6 alkyl), (Z)pC≡CR25 and (Z)pCR28═CR26R27;
ii) a 5-6 membered heterocyclic ring in which the ring contains 1 to 3 heteroatoms (each independently chosen from oxygen, sulphur and nitrogen) and the ring is optionally substituted by up to 3 substituents, each independently selected from halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C(H)═N—O—(C1-6 alkyl) and C(C1-6 alkyl)cyano, C1-4 alkoxy, C1-4 thioalkyl, COO—C1-4 alkyl, ═N—OH, ═N—O—(C1-4 alkyl), C3-8 cycloalkyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy) and C4-8 cycloalkenyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy);
iii) C2-12 alkenyl optionally substituted by up to 6 substituents, each independently selected from halogen, cyano, C1-4 alkoxy, C1-4 thioalkyl, COO—(C1-4 alkyl), ═N—OH, ═N—O—(C1-4 alkyl), C3-8 cycloalkyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4alkoxy and C1-4 haloalkoxy) and C4-8 cycloalkenyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy);
iv) C2-12 alkynyl optionally substituted by up to 6 substituents, each independently selected from halogen, cyano, C1-4 alkoxy, C1-4 thioalkyl, COO—C1-4 alkyl, ═N—OH, ═H—O—(C1-4 alkyl), C3-8 cycloalkyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy), Si(CH3)3 and C4-8 cycloalkenyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy);
v) C3-8 cycloalkyl optionally substituted by up to 3 substituents, each independently selected from halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 thioalkyl, C3-6 cycloalkyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4 alkoxy and C1-4 haloalkoxy) and phenyl (itself optionally substituted by up to five independently selected halogen atoms);
vi) C4-8 cycloalkenyl optionally substituted by up to 3 substituents, each independently selected from halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 thioalkyl, C3-6 cycloalkyl (itself optionally substituted by up to 3 substituents, each independently selected from C1-4 alkyl, halogen, C1-4alkoxy and C1-4 haloalkoxy) and phenyl (itself optionally substituted by up to five independently selected halogen atoms);
vii) C6-12 bicycloalkyl optionally substituted by up to 3 substituents, each independently selected from halogen, C1-4 alkyl and C1-4 haloalkyl; or
viii) an aliphatic, saturated or unsaturated group in which the group contains three to thirteen carbon atoms and at least one silicon atom and, optionally, one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, and the group is optionally substituted by up to four independently selected halogen atoms;
R7, R8, R9, R10, R11 and R12 are each, independently, hydrogen, halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 thioalkyl or C1-4 thiohaloalkyl; R13, R14, R15, R16 and R17 are each, independently, hydrogen, halogen, C1-4 alkyl, C(O)CH3, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 thioalkyl, C1-4 thiohaloalkyl, hydroxymethyl or C1- alkoxymethyl; R18 is hydrogen, C1-4 alkyl, C1-4 alkoxy(C1-4)alkyl, formyl, C(═O)C1-4alkyl (optionally substituted by halogen or C1-4 alkoxy) or C(═O)O—C1-6 alkyl (optionally substituted by halogen, C1-4 alkoxy or CN); R19, R20, R21, R22, R23 and R24 are each, independently, C1-6 alkyl, C1-6 alkenyl both optionally substituted by halogen, hydroxy, ═O, C1-4 alkoxy, O—C(O)—C1-4 alkyl, aryl or a 3-7 membered carbocyclic ring (itself optionally substituted by up to three methyl groups), a 3-7 membered carbocyclic ring (optionally substituted by up to three methyl groups and optionally containing one heteroatom selected from nitrogen and oxygen), hydrogen, halogen, hydroxy or C1-4 alkoxy; or R19R20 together with the carbon atom to which they are attached form a carbonyl-group, a 3-5 membered carbocyclic ring (optionally substituted by up to three methyl groups), C1-6 alkylidene (optionally substituted by up to three methyl groups) or C3-6 cycloalkylidene (optionally substituted by up to three methyl groups); R25 is hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4 haloalkoxy(C1-4)alkyl or Si(C1-4 alkyl)3; R26 and R27 are each, independently, hydrogen, halogen, C1-4 alkyl or C1-4 haloalkyl; R28 is hydrogen, C1-4 alkyl or C1-4 haloalkyl; m is 0 or 1; n is 0 or 1; p is 0 or 1; and Z is C1-4 alkylene.