Plant growth regulation

A method of regulating growth in crop plants, comprising:

• (a) applying an effective amount of a compound of formula (I) to plants, seeds or a loci in which said plants or seeds grow, wherein said compound has the following structure:
• or an agriculturally acceptable salt thereof,
• wherein:
• E is (C1-C6)alkyl, (C2-C6)alkenyl, (C3-C6)alkynyl, (C1-C6)alkoxy-(C1-C6)alkyl, [(C1-C6)alkoxy]carbonyl-(C1-C6)alkyl, [(C1-C6)alkyl]carbonyloxy-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, furfuryl, tetrahydrofurfuryl or isoxazolyl which last mentioned group is unsubstituted or substituted with one or two (C1-C6)alkyl radicals;
• or is a group of formula (A):
• in which X, Y, Z and V are each independently C or N, with the proviso that at least two of X, Y, Z and V are C;
• the linking bond of (A) is attached to a ring carbon atom;
• (R1)u are u substituents of R1 which may be same or different, each R1 is linked to a ring carbon atom and is H, R2, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, [(C3-C8)cycloalkyl]carbonyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl-S(O)m, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl where each of the last 3 mentioned radicals is unsubstituted or substituted by one or more R2 radicals;
• or aryl, heterocyclyl, aryl-(C1-C6)alkyl, heterocyclyl-(C1-C6)alkyl, aryl-(C1-C6)alkoxy, heterocyclyl-(C1-C6)alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, heterocyclyloxy, aryl-S(O)n or heterocyclyl-S(O)p, where the aryl or heterocyclyl portion of the last 12 mentioned radicals is unsubstituted or substituted by one to three radicals selected from the group consisting of R2, (C1-C6)alkyl, (C2-C6)alkenyl and (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or (A) is fused to a 1,3-dioxolanyl or 1,4-dioxanyl ring where each of the last two mentioned rings is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy and OH;
• each R2 independently from other R2 radicals is hydroxy, halogen, cyano, nitro, NR3R4, CONR3R4, OCONR3R4, OCH2CONR3R4, (C1-C6)alkoxy, (C1-C6)haloalkoxy, CO2R3, COR3, NHCOR3, NHCO2R3, S(O)qR5, SO2NH2 or R6;
• R3 is hydrogen, (C1-C6)-alkyl or CH2R6;
• R4 is hydrogen or (C1-C6)-alkyl;
• or R3 and R4 together with the nitrogen atom to which they are attached form a 3 to 8 membered cyclic ring optionally containing one or two further hetero atoms selected from oxygen, sulfur and nitrogen;
• R5 is (C1-C6)alkyl or (C1-C6)haloalkyl;
• W is O or N—OR7;
• R6 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)haloalkyl and (C1-C6)alkoxy;
• R7 is hydrogen, (C1-C6)alkyl or aryl-(C1-C6)alkyl;
• Q is (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, where the last 2 mentioned radicals are unsubstituted or substituted in the cycloalkyl by (C1-C4)alkyl, (C1-C4)alkoxy and halogen, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or
• aryl, heterocyclyl, aryl-(C1-C6)alkyl or heterocyclyl-(C1-C6)alkyl, where the aryl or heterocyclyl portion of the last 4 mentioned radicals is unsubstituted or substituted by:
• i) one to three radicals selected from the group consisting of R2, (C1-C6)alkyl, (C2-C6)alkenyl and (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or
• ii) (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, [(C3-C8)cycloalkyl]carbonyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl-S(O)r, aryl, heterocyclyl, aryl-(C1-C6)alkyl, heterocyclyl-(C1-C6)alkyl, aryl-(C1-C6)alkoxy, heterocyclyl-(C1-C6)alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, (C3-C8)-heterocyclyloxy, aryl-S(O)s or heterocyclyl-S(O)t, which last 12 mentioned radicals is unsubstituted or substituted by one or two radicals selected from the group consisting of (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl and R2;
• m, n, p, q, r, s and t are each independently 0, 1 or 2;
• u is the number of ring carbon atoms in formula (A) minus 1;
• and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A composition for plant growth regulation, which comprises one or more compounds of formula (I) having the following structure:

• or an agriculturally acceptable salt thereof,
• wherein:
• E is (C1-C6)alkyl, (C2-C6)alkenyl, (C3-C6)alkynyl, (C1-C6)alkoxy-(C1-C6)alkyl, [(C1-C6)alkoxy]carbonyl-(C1-C6)alkyl, [(C1-C6)alkyl]carbonyloxy-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, furfuryl, tetrahydrofurfuryl or isoxazolyl which last mentioned group is unsubstituted or substituted with one or two (C1-C6)alkyl radicals;
• or is a group of formula (A):
• in which X, Y, Z and V are each independently C or N, with the proviso that at least two of X, Y, Z and V are C;
• the linking bond of (A) is attached to a ring carbon atom;
• (R1)u are u substituents of R1 which may be same or different, each R1 is linked to a ring carbon atom and is H, R2, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, [(C3-C8)cycloalkyl]carbonyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl-S(O)m, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl where each of the last 3 mentioned radicals is unsubstituted or substituted by one or more R2 radicals;
• or aryl, heterocyclyl, aryl-(C1-C6)alkyl, heterocyclyl-(C1-C6)alkyl, aryl-(C1-C6)alkoxy, heterocyclyl-(C1-C6)alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, heterocyclyloxy, aryl-S(O)n or heterocyclyl-S(O)p, where the aryl or heterocyclyl portion of the last 12 mentioned radicals is unsubstituted or substituted by one to three radicals selected from the group consisting of R2, (C1-C6)alkyl, (C2-C6)alkenyl and (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or (A) is fused to a 1,3-dioxolanyl or 1,4-dioxanyl ring where each of the last two mentioned rings is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy and OH;
• each R2 independently from other R2 radicals is hydroxy, halogen, cyano, nitro, NR3R4, CONR3R4, OCONR3R4, OCH2CONR3R4, (C1-C6)alkoxy, (C1-C6)haloalkoxy, CO2R3, COR3, NHCOR3, NHCO2R3, S(O)qR5, SO2NH2 or R6;
• R3 is hydrogen, (C1-C6)-alkyl or CH2R6;
• R4 is hydrogen or (C1-C6)-alkyl;
• or R3 and R4 together with the nitrogen atom to which they are attached form a 3 to 8 membered cyclic ring optionally containing one or two further hetero atoms selected from oxygen, sulfur and nitrogen;
• R5 is (C1-C6)alkyl or (C1-C6)haloalkyl;
• W is O or N—OR7;
• R6 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)haloalkyl and (C1-C6)alkoxy;
• R7 is hydrogen, (C1-C6)alkyl or aryl-(C1-C6)alkyl;
• Q is (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, where the last 2 mentioned radicals are unsubstituted or substituted in the cycloalkyl by (C1-C4)alkyl, (C1-C4)alkoxy and halogen, (C1-C6)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or
• aryl, heterocyclyl, aryl-(C1-C6)alkyl or heterocyclyl-(C1-C6)alkyl, where the aryl or heterocyclyl portion of the last 4 mentioned radicals is unsubstituted or substituted by:
• i) one to three radicals selected from the group consisting of R2, (C1-C6)alkyl, (C2-C6)alkenyl and (C2-C6)alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R2 radicals;
• or
• ii) (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C1-C6)alkoxy, [(C3-C8)cycloalkyl]carbonyl, (C3-C8)cycloalkyloxy, (C3-C8)cycloalkyl-S(O)r, aryl, heterocyclyl, aryl-(C1-C6)alkyl, heterocyclyl-(C1-C6)alkyl, aryl-(C1-C6)alkoxy, heterocyclyl-(C1-C6)alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, (C3-C8)-heterocyclyloxy, aryl-S(O)s or heterocyclyl-S(O)t, which last 12 mentioned radicals is unsubstituted or substituted by one or two radicals selected from the group consisting of (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl and R2;
• m, n, p, q, r, s and t are each independently 0, 1 or 2;
• u is the number of ring carbon atoms in formula (A) minus 1;
• and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S;
• and
• carriers, surfactants and mixtures thereof useful for plant protection formulations.