Fungicidal halomethyl ketones and hydrates

A compound selected from Formula 1, tautomers, A-oxides, and salts thereof,

• wherein
• T is selected from the group consisting of:
• wherein the bond extending to the left is attached to A;
• R1 is CF3, CHF2, CCl3, CHCl2, CF2Cl, CFCl2 or CHFCl;
• W is O, S or NR3;
• R3 is H, cyano, nitro, C(═O)OH, benzyl, C3-C4 alkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, OR3a or NR3bR3c;
• R3a is H, benzyl, C3-C4 alkyl, C2-C4 alkylcarbonyl or C2-C4 haloalkylcarbonyl;
• R3b is H, C3-C4 alkyl, C2-C4 alkylcarbonyl or C2-C4 haloalkylcarbonyl;
• R3c is H or C3-C4 alkyl;
• or
• R3b and R3c are taken together to form a 4- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 methyl groups;
• X is O, S or NR5a;
• Y is O, S or NR5b;
• R5a and R5b are each independently H, hydroxy or C1-C4 alkyl;
• R2a and R2b are each independently H, C1-C4 alkyl, C2-C4 alkenyl, (CR4aR4b)p—OH, (CR4aR4b)p—SH, (CR4aR4b)p—Cl or (CR4aR4b)p—Br;
• or
• R2a and R2b are taken together with the atoms X and Y to which they are attached to form a 5- to 7-membered saturated ring containing ring members, in addition to the atoms X and Y, selected from carbon atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl, alkoxy and C1-C2 haloalkoxy on carbon atom ring members;
• R2c is C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl or C2-C4 haloalkynyl, each optionally substituted with up 2 substituents independently selected from cyano, hydroxy, SC≡N and C1-C2 alkoxy;
• R2d is H, cyano, halogen or C1-C4 alkyl;
• each R4a and R4b is independently H or C1-C4 alkyl;
• p is 2 or 3;
• when T is T-1 or T-2, then A is A1-A2-CR6aR6b, wherein A1 is connected to J, and CR6aR6b is connected to T;
• when T is T-3, then A is A1-A2, wherein A1 is connected to J, and A2 is connected to T;
• A1 is CR6cR6d, N(R7a), O or S;
• A2 is a direct bond, CR6eR6f, N(R7b), O or S;
• R6a, R6b, R6c, R6d, R6e and R6f are each independently H, cyano, hydroxy, halogen or C1-C4 alkyl;
• R7a and R7b are each independently H, C(═O)H, C1-C4 alkyl or C2-C4 alkyl carbonyl;
• J is selected from the group consisting of:
• wherein the bond extending to the left is attached to L, and the bond extending to the right is attached to A;
• each R8 is independently F, Cl, methyl or methoxy;
• q is 0, 1 or 2;
• L is (CR9aR9b)n;
• each R9a and R9b is independently H, halogen, cyano, hydroxy, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;
• n is 0, 1, 2 or 3;
• E is E1 or E2;
• E1 is amino, cyano, hydroxy, nitro, CH(═O), C(═O)OH, C(═O)NH2, C(═S)NH2, OC(═O)NH2, OC(═S)NH2, NHC(═O)NH2, NHC(═S)NH2, SCAN, —CH═NNHC(═O)OC1-C6 alkyl or —N(OCH3)C(═O)C1-C6 alkyl;
• or
• E1 is C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C6 alkylthio, C2-C6 alkenylthio, C2-C6 alkynylthio, C1-C6 alkylsulfinyl, C2-C6 alkenylsulfinyl, C2-C6 alkynylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenylsulfonyl, C2-C6 alkynylsulfonyl, C1-C6 alkylsulfonylamino, C2-C6 alkenylsulfonylamino, C2-C6 alkynylsulfonylamino, C1-C6 alkylaminosulfonyl, C2-C6 dialkylaminosulfonyl, C2-C6 alkenylaminosulfonyl, C2-C6 alkynylaminosulfonyl, C1-C6 alkylaminosulfonylamino, C2-C6 alkenylaminosulfonylamino, C2-C6 alkynylaminosulfonylamino, C2-C6 alkylcarbonyl, C3-C6 alkenylcarbonyl, C3-C6 alkynylcarbonyl, C2-C6 alkylaminocarbonyl, C3-C6 alkenylaminocarbonyl, C3-C6 alkynylaminocarbonyl, C2-C6 alkylcarbonylamino, C3-C6 alkenylcarbonylamino, C3-C6 alkynylcarbonylamino, C2-C6 alkylaminocarbonylamino, C3-C6 alkenylaminocarbonylamino, C3-C6 alkynylaminocarbonylamino, C2-C6 alkylcarbonyloxy, C3-C6 alkenylcarbonyloxy, C3-C6 alkynylcarbonyloxy, C2-C6 alkoxycarbonyl, C3-C6 alkenyloxycarbonyl, C3-C6 alkynyloxycarbonyl, C2-C6 alkylaminocarbonyloxy, C3-C6 alkenylaminocarbonyloxy, C3-C6 alkynylaminocarbonyloxy, C2-C6 alkoxycarbonylamino, C3-C6 alkenyloxycarbonylamino, C3-C6 alkynyloxycarbonylamino, C2-C6 alkylamino(thiocarbonyl)oxy, C3-C6 alkenylamino(thiocarbonyl)oxy, C3-C6 alkynylamino(thiocarbonyl)oxy, C2-C6 alkoxy(thiocarbonyl)amino, C3-C6 alkenyloxy(thiocarbonyl)amino, C3-C6 alkynyloxy(thiocarbonyl)amino, C2-C6 alkyl(thiocarbonyl), C2-C6 (alkylthio)carbonyl, C3-C6 alkenyl(thiocarbonyl), C3-C6 (alkenylthio)carbonyl, C3-C6 alkynyl(thiocarbonyl), C3-C6 (alkynylthio)carbonyl, C2-C6 alkylamino(thiocarbonyl), C3-C6 alkenylamino(thiocarbonyl), C3-C6 alkynylamino(thiocarbonyl), C2-C6 alkyl(thiocarbonyl)amino, C2-C6 (alkylthio)carbonylamino, C3-C6 alkenyl(thiocarbonyl)amino, C3-C6 (alkenylthio)carbonylamino, C3-C6 alkynyl(thiocarbonyl)amino, C3-C6 (alkynylthio)carbonylamino, C2-C6 alkylamino(thiocarbonyl)amino, C3-C6 alkenylamino(thiocarbonyl)amino or C3-C6 alkynylamino(thiocarbonyl)amino, wherein each carbon atom is optionally substituted with up to 1 substituent selected from R10a and up to 3 substituents independently selected from R10b;
• R10a is phenyl optionally substituted with up to 3 substituents independently selected from R11a;
• or a 5- to 6-membered heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S), and sulfur atom ring members are independently S(═O)u(═NR12)v, each ring optionally substituted with up to 3 substituents independently selected from R11a on carbon atom ring members and R11b on nitrogen atom ring members;
• each R10b is independently amino, cyano, halogen, hydroxy, nitro, SC≡N, —SH, C1-C4 alkyl, C3-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C4 alkoxy, C3-C4 haloalkoxy, C3-C4 alkylthio, C3-C4 alkylsulfinyl, C3-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C4 dialkylamino, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C5 haloalkoxycarbonyl, C2-C5 alkylaminocarbonyl or C3-C5 dialkylaminocarbonyl;
• each R11a is independently halogen, hydroxy, cyano, amino, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 hydroxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C2-C4 alkoxyalkyl, C2-C6 alkylcarbonyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C2-C6 alkylcarbonylthio, alkylsulfinyl, Q-Q haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylsulfonyloxy, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C4 alkylcarbonyl, C3-C5 alkenylcarbonyl, C3-C5 alkynylcarbonyl, C4-C7 cycloalkylcarbonyl, C5-C8 cycloalkylalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 alkenyloxycarbonyl, C3-C7 alkynyloxycarbonyl, C4-C7 cycloalkoxylcarbonyl, C5-C8 cycloalkylalkoxylcarbonyl, C2-C6 alkylaminocarbonyl, C3-C6 alkenylaminocarbonyl, C3-C6 alkynylaminocarbonyl, C4-C7 cycloalkylaminocarbonyl, C5-C8 cycloalkylalkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl;
• each R11b is independently C(═O)H, C1-C3 alkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl;
• each R12 is independently H, cyano, C1-C3 alkyl or C1-C3 haloalkyl;
• each u and v are independently 0, 1 or 2, provided that the sum of u and v are 0, 1 or 2;
• E2 is G-Z, wherein Z is attached to L;
• G is phenyl optionally substituted with up to 3 substituents independently selected from R13;
• or
• G is a 5- to 6-membered heteroaromatic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R13;
• or
• G is a 3- to 7-membered nonaromatic ring or an 8- to 11-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and optionally up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O)2, each ring or ring system optionally substituted with up to 3 substituents independently selected from R13;
• each R13 is independently cyano, halogen, hydroxy, nitro, —SH, SF5, CH(═O), C(═O)OH, NR14aR14b, C(═O)NR14aR14b, C(═O)C(═O)NR14aR14b, C(═S)NR14aR14b, C(R15)═NR16, N═CR17NR18aR18b or —U—V-Q;
• or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 cycloalkenyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C7 cycloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylaminosulfinyl, C2-C6 dialkylaminosulfinyl, C1-C6 alkylsulfonyloxy, C1-C6 alkylsulfonylamino, C2-C6 alkyl carbonyl, C4-C7 cycloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C6 alkenyloxycarbonyl, C3-C6 alkynyloxycarbonyl, C4-C7 cycloalkoxycarbonyl, C3-C6 alkoxycarbonylcarbonyl, C2-C6 alkylcarbonyloxy, C4-C7 cycloalkylcarbonyloxy, C2-C6 alkoxycarbonyloxy, C4-C7 cycloalkoxycarbonyloxy, C2-C6 alkylaminocarbonyloxy, C4-C7 cycloalkylaminocarbonyloxy, C2-C6 alkylcarbonylamino, C4-C7 cycloalkylcarbonylamino, C2-C6 alkoxycarbonylamino, C4-C7 cycloalkoxycarbonylamino, C2-C6 alkylaminocarbonylamino, C4-C7 cycloalkylaminocarbonylamino or C2-C6 dialkoxyphosphinyl, each optionally substituted with up to 3 substituents independently selected from R19;
• each R14a is independently H, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C5 alkoxy, C2-C4 alkoxyalkyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkylthioalkyl, C2-C4 alkylsulfinylalkyl, C2-C4 alkylsulfonylalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C4-C7 cycloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl or C3-C5 dialkylaminocarbonyl;
• each R14b is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl, C2-C6 cyanoalkyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C6 alkylthioalkyl, C2-C6 alkylsulfinylalkyl, C2-C6 alkylsulfonylalkyl, C2-C6 alkylaminoalkyl, C2-C6 haloalkylaminoalkyl, C3-C8 dialkylaminoalkyl or C4-C10 cycloalkylaminoalkyl, each optionally substituted with up to 1 substituent selected from cyano, hydroxy, nitro, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C3-C15 trialkylsilyl and C3-C15 halotrialkylsilyl;
• or
• R14a and R14b are taken together to form a 4- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 3 substituents independently selected from halogen and C1-C3 alkyl;
• each R15 is independently H, cyano, halogen, methyl, methoxy, methylthio or methoxy carbonyl;
• each R16 is independently hydroxy or NR20aR20b;
• or C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C2-C4 alkylcarbonyloxy, C2-C5 alkoxycarbonyloxy, C2-C5 alkylaminocarbonyloxy or C3-C5 dialkylaminocarbonyloxy, each optionally substituted with up to 1 substituent selected from cyano, halogen, hydroxy and C(═O)OH;
• each R17 is independently H, methyl, methoxy or methylthio;
• each R18a and R18b is independently H or C1-C4 alkyl;
• or
• R18a and R18b are taken together to form a 5- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 methyl groups;
• each R19 is independently amino, cyano, halogen, hydroxy, nitro, —SH, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl, C1-C6 alkylamino, C2-C6 dialkylamino, C2-C5 alkylaminocarbonyl, C3-C5 dialkylaminocarbonyl, C3-C5 alkylthioalkylcarbonyl, C3-C15 trialkylsily, C3-C15 halotrialkylsilyl, C(R21)═NOR22 or C(R23)═NR24;
• each U is independently a direct bond, C(═O)O, C(═O)N(R25) or C(═S)N(R26), wherein the atom to the left is connected to G, and the atom to the right is connected to V;
• each V is independently a direct bond;
• or C1-C6 alkylene, C2-C6 alkenylene, C3-C6 alkynylene, C3-C6 cycloalkylene or C3-C6 cycloalkenylene, wherein up to 1 carbon atom is C(═O), each optionally substituted with up to 3 substituents independently selected from halogen, cyano, nitro, hydroxy, alkyl, C1-C2 haloalkyl, alkoxy and C1-C2 haloalkoxy;
• each Q is independently phenyl or phenoxy, each optionally substituted with up to 2 substituents independently selected from R27;
• or
• each Q is independently a 5- to 6-membered heteroaromatic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 2 substituents independently selected from R27;
• or
• each Q is independently a 3- to 7-membered nonaromatic heterocyclic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O)2, each ring optionally substituted with up to 2 substituents independently selected from R27;
• each R20a is independently H, C1-C4 alkyl or C2-C4 alkylcarbonyl;
• each R20b is independently H, cyano, C3-C5 alkyl, C2-C5 alkylcarbonyl, C2-C5 haloalkylcarbonyl, C4-C7 cycloalkylcarbonyl, C2-C5 alkoxycarbonyl, C3-C5 alkoxycarbonylalkyl, C2-C5 alkylaminocarbonyl or C3-C5 dialkylaminocarbonyl;
• or
• R20a and R20b are taken together to form a 5- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 methyl groups;
• each R21 and R23 is independently H, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl or C1-C3 alkoxy;
• or phenyl optionally substituted with up to 2 substituents independently selected from halogen and C1-C3 alkyl;
• each R22 is independently H, C3-C5 alkyl, C3-C5 haloalkyl, C2-C5 alkenyl, C2-C5 haloalkenyl, C2-C5 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C5 alkylcarbonyl or C2-C5 alkoxycarbonyl;
• or
• each R22 is phenyl optionally substituted with up to 2 substituents independently selected halogen and C1-C3 alkyl;
• or a 5- to 6-membered fully saturated heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 substituents independently selected from halogen and C1-C3 alkyl;
• each R24 is independently H, cyano, C1-C3 alkyl, C1-C3 haloalkyl, alkoxy, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• each R25 and R26 is independently H, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkoxycarbonyl or C2-C4 haloalkoxycarbonyl;
• each R27 is independently halogen, cyano, hydroxy, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C1-C4 alkoxy, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
• Z is a direct bond, O, S(═O)m, N(R28), C(═O), C(═O)N(R28), NR28C(═O), N(R28)C(═O)N(R28), N(R28)C(═S)N(R28), OC(═O)N(R28), N(R28)C(═O)O, S(O)2N(R28), N(R28)S(═O)2 or N(R28)S(O)2N(R28), wherein the atom to the right is connected to L;
• each R28 is independently H, C1-C3 alkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl;
• and
• m is 0, 1 or 2;
• provided that:
• (c) when A1 is N(R7a), O or S, then A2 is a direct bond or CR6eR6f;
• and
• when A2 is N(R7b), O or S;
• then A1 is CR6cR6d.