Plant growth regulation
The present invention relates to a new class of plant growth regulators. In particular, the invention relates to 2,4-diamino-5-substituted-thiazole derivatives of general formula (I); and a method for treatment of plants with such compounds in order to induce growth-regulating responses.
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12 . 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 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )alkynyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkoxy]carbonyl-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkyl]carbonyloxy-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, furfuryl, tetrahydrofurfuryl or isoxazolyl which last mentioned group is unsubstituted or substituted with one or two (C 1 -C 6 )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;
(R 1 ) u are u substituents of R 1 which may be same or different, each R 1 is linked to a ring carbon atom and is H, R 2 , (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkoxy, [(C 3 -C 8 )cycloalkyl]carbonyl, (C 3 -C 8 )cycloalkyloxy, (C 3 -C 8 )cycloalkyl-S(O) m , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl where each of the last 3 mentioned radicals is unsubstituted or substituted by one or more R 2 radicals;
or aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl, heterocyclyl-(C 1 -C 6 )alkyl, aryl-(C 1 -C 6 )alkoxy, heterocyclyl-(C 1 -C 6 )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 R 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 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, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and OH;
each R 2 independently from other R 2 radicals is hydroxy, halogen, cyano, nitro, NR 3 R 4 , CONR 3 R 4 , OCONR 3 R 4 , OCH 2 CONR 3 R 4 , (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, CO 2 R 3 , COR 3 , NHCOR 3 , NHCO 2 R 3 , S(O) q R 5 , SO 2 NH 2 or R 6 ;
R 3 is hydrogen, (C 1 -C 6 )-alkyl or CH 2 R 6 ;
R 4 is hydrogen or (C 1 -C 6 )-alkyl; or R 3 and R 4 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;
R 5 is (C 1 -C 6 )alkyl or (C 1 -C 6 )haloalkyl;
W is O or N—OR 7 ;
R 6 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl and (C 1 -C 6 )alkoxy;
R 7 is hydrogen, (C 1 -C 6 )alkyl or aryl-(C 1 -C 6 )alkyl;
Q is (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, where the last 2 mentioned radicals are unsubstituted or substituted in the cycloalkyl by (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy and halogen, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 radicals; or
aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl or heterocyclyl-(C 1 -C 6 )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 R 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 radicals; or
ii) (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkoxy, [(C 3 -C 8 )cycloalkyl]carbonyl, (C 3 -C 8 )cycloalkyloxy, (C 3 -C 8 )cycloalkyl-S(O) r , aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl, heterocyclyl-(C 1 -C 6 )alkyl, aryl-(C 1 -C 6 )alkoxy, heterocyclyl-(C 1 -C 6 )alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, (C 3 -C 8 )-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 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl and R 2 ;
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.
13 . The method of claim 12 , wherein said (A) of formula (I) is a formula (A1), (A2), (A3), (A4) or (A5):
wherein R 1 and u are as defined in claim 12 .
14 . The method of claim 12 , wherein:
E is (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkoxy]carbonyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl or a group (A):
X, Y, Z and V are each C;
each R 1 which may be the same or different is H, hydroxy, halogen, cyano, nitro, NR 3 R 4 , CONR 3 R 4 , (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, CO 2 R 3 , COR 3 , NHCOR 3 , S(O) q R 5 , SO 2 NH 2 , (C 1 -C 3 )alkyl or (C 1 -C 3 )haloalkyl, wherein R 3 and R 4 are each independently hydrogen or (C 1 -C 3 )-alkyl, and R 5 is (C 1 -C 3 )alkyl or (C 1 -C 3 )haloalkyl;
or phenyl or pyridyl, which last 2 mentioned radicals are unsubstituted or substituted by one to three radicals selected from the group consisting of halogen, (C 1 -C 6 )alkyl and (C 1 -C 3 )haloalkyl; and
u is 5.
15 . The method of claim 12 , wherein:
E is (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy-(C 1 -C 3 )alkyl, [(C 1 -C 3 )alkoxy]carbonyl-(C 1 -C 3 )alkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 3 )alkyl or a group of formula (A):
X, Y and Z are all C; V is C or N; R 1 is H or halogen; and
u is 4 or 5.
16 . The method of claim 12 , wherein:
E is (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy-(C 1 -C 3 )alkyl, [(C 1 -C 3 )alkoxy]carbonyl-(C 1 -C 3 )alkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 3 )alkyl or a group (A):
X, Y, Z and V are all C;
W is O;
R 1 is H or halogen;
Q is cyclopropyl, (C 1 -C 3 )alkyl, phenyl, naphthyl, pyridinyl, tetrahydropyridinyl, thienyl or benzo[b]thienyl, which last 6 mentioned radicals are unsubstituted or substituted by one to three radicals selected from the group consisting of halogen, (C 1 -C 3 )alkyl, OH, NO 2 , (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, phenyl and benzyloxy; and
u is 5.
17 . The method of claim 12 that results into a yield increase of at least 10% concerning the plants to which it is applied.
18 . 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 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )alkynyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkoxy]carbonyl-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkyl]carbonyloxy-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, furfuryl, tetrahydrofurfuryl or isoxazolyl which last mentioned group is unsubstituted or substituted with one or two (C 1 -C 6 )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;
(R 1 ) u are u substituents of R 1 which may be same or different, each R 1 is linked to a ring carbon atom and is H, R 2 , (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkoxy, [(C 3 -C 8 )cycloalkyl]carbonyl, (C 3 -C 8 )cycloalkyloxy, (C 3 -C 8 )cycloalkyl-S(O) m , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl where each of the last 3 mentioned radicals is unsubstituted or substituted by one or more R 2 radicals;
or aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl, heterocyclyl-(C 1 -C 6 )alkyl, aryl-(C 1 -C 6 )alkoxy, heterocyclyl-(C 1 -C 6 )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 R 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 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, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and OH;
each R 2 independently from other R 2 radicals is hydroxy, halogen, cyano, nitro, NR 3 R 4 , CONR 3 R 4 , OCONR 3 R 4 , OCH 2 CONR 3 R 4 , (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, CO 2 R 3 , COR 3 , NHCOR 3 , NHCO 2 R 3 , S(O) q R 5 , SO 2 NH 2 or R 6 ;
R 3 is hydrogen, (C 1 -C 6 )-alkyl or CH 2 R 6 ;
R 4 is hydrogen or (C 1 -C 6 )-alkyl; or R 3 and R 4 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;
R 5 is (C 1 -C 6 )alkyl or (C 1 -C 6 )haloalkyl;
W is O or N—OR 7 ;
R 6 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl and (C 1 -C 6 )alkoxy;
R 7 is hydrogen, (C 1 -C 6 )alkyl or aryl-(C 1 -C 6 )alkyl;
Q is (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, where the last 2 mentioned radicals are unsubstituted or substituted in the cycloalkyl by (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy and halogen, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 radicals; or
aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl or heterocyclyl-(C 1 -C 6 )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 R 2 , (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl and (C 2 -C 6 )alkynyl, where each of the last 3 mentioned radicals is unsubstituted or substituted by one or two R 2 radicals; or
ii) (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkoxy, [(C 3 -C 8 )cycloalkyl]carbonyl, (C 3 -C 8 )cycloalkyloxy, (C 3 -C 8 )cycloalkyl-S(O) r , aryl, heterocyclyl, aryl-(C 1 -C 6 )alkyl, heterocyclyl-(C 1 -C 6 )alkyl, aryl-(C 1 -C 6 )alkoxy, heterocyclyl-(C 1 -C 6 )alkoxy, aryl-carbonyl, heterocyclyl-carbonyl, aryloxy, (C 3 -C 8 )-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 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl and R 2 ;
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.
19 . The composition as claimed in claim 18 , further comprising a compound selected from the group consisting of acaricides, fungicides, herbicides, insecticides, nematicides or plant growth regulating substances not identical to compounds defined by formula (I).
20 . The composition of claim 18 , wherein said (A) of formula (I) is a formula (A1), (A2), (A3), (A4) or (A5):
wherein R 1 and u are as defined in claim 18 .
21 . The composition of claim 18 , wherein:
E is (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, [(C 1 -C 6 )alkoxy]carbonyl-(C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 )alkyl or a group (A):
X, Y, Z and V are each C;
each R 1 which may be the same or different is H, hydroxy, halogen, cyano, nitro, NR 3 R 4 , CONR 3 R 4 , (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, CO 2 R 3 , COR 3 , NHCOR 3 , S(O) q R 5 , SO 2 NH 2 , (C 1 -C 3 )alkyl or (C 1 -C 3 )haloalkyl, wherein R 3 and R 4 are each independently hydrogen or (C 1 -C 3 )-alkyl, and R 5 is (C 1 -C 3 )alkyl or (C 1 -C 3 )haloalkyl;
or phenyl or pyridyl, which last 2 mentioned radicals are unsubstituted or substituted by one to three radicals selected from the group consisting of halogen, (C 1 -C 6 )alkyl and (C 1 -C 3 )haloalkyl; and
u is 5.
22 . The composition of claim 18 , wherein:
E is (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy-(C 1 -C 3 )alkyl, [(C 1 -C 3 )alkoxy]carbonyl-(C 1 -C 3 )alkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 3 )alkyl or a group of formula (A):
X, Y and Z are all C; V is C or N; R 1 is H or halogen; and
u is 4 or 5.
23 . The composition of claim 18 , wherein:
E is (C 1 -C 3 )alkyl, (C 1 -C 3 )alkoxy-(C 1 -C 3 )alkyl, [(C 1 -C 3 )alkoxy]carbonyl-(C 1 -C 3 )alkyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 3 )alkyl or a group (A):
X, Y, Z and V are all C;
W is O;
R 1 is H or halogen;
Q is cyclopropyl, (C 1 -C 3 )alkyl, phenyl, naphthyl, pyridinyl, tetrahydropyridinyl, thienyl or benzo[b]thienyl, which last 6 mentioned radicals are unsubstituted or substituted by one to three radicals selected from the group consisting of halogen, (C 1 -C 3 )alkyl, OH, NO 2 , (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy, phenyl and benzyloxy; and
u is 5.
24 . A method of regulating growth in crop plants, comprising
(a) applying an effective amount of a composition of claim 18 to a monocotyledoneous or dicotyledoneous crop plant.
25 . The method of claim 24 , wherein the plant is selected from the group consisting of wheat, barley, rye, triticale, rice, maize, sugar beet, cotton and soybeans.