EP0067511A2
Expired / Lapsed
EP
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Method of inducing tillering using pyridine derivatives, and some of the pyridines themselves, process for preparing them and agricultural compositions containing them
Assignee: Imperial Chemical Industries Ltd
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Filing: 1982-04-29
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Granted: —
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Expires: 2002-04-29
Abstract
Abstract A method for inducing tillering in monocotyledonous (e.g. cereals) using compounds having the formula : wherein R 1 is hydrogen, halogen, alkyl, hydroxy, amino, phenyl or alkoxy carbonyl, R 2 is cyano or carboxy or a derivative thereof, R 3 is optionally substituted phenyl, and n is 0 or 1.
Inventors
- 👤 Gilbert Joseph Stacey
- 👤 Alan Francis Hawkins
- 👤 David Philip John Pearson
- 👤 Raymond Leo Sunley
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 14:21
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; A; A01; A01N; A01N43/00; A01N43/34; A01N43/40; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/673; C07D213/79; C07D213/80; C07D213/81; C07D213/82; C07D213/84; C07D213/85; C07D213/86; C07D213/87; C07D213/89
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
488 words
1 . A method of inducing tiller formation in a monocotyledonous plant, characterised by applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of general formula (I) : wherein R 1 is hydrogen, halogen, optionally halo- or acetoxy- substituted C l-4 alkyl, hydroxy, amino, phenyl or (C 1-5 alkoxy) carbonyl; R 2 is cyano, or a group of general formula -CO R 4 wherein R 4 is -O- l/m M m+ , -OR 5 , -SR 6 , -NR 7 R 8 or -NR 9 -NR 10 R 11 wherein M is an m-valent cation; R 5 is C 1-8 alkyl optionally substituted with halogen, hydroxy, cyano, C 1-4 alkoxy, C 1-4 alkylthio, carboxy, (C 1-4 alkoxy)carbonyl, C 3-6 cycloalkyl, amino, mono- or di- C 1-4 alkylamino, a 5- or 6-membered heterocyclic ring or optionally halo- or C 1-4 alkylsubstituted phenyl; C 3-6 cycloalkyl; optionally halo- substituted C 2-6 alkenyl; C 3-6 alkynyl; or phenyl optionally substituted with halogen, C 1-4 alkyl, C l-4 alkoxy, C l-4 alkylthio, cyano or nitro; R 6 is C 1-8 alkyl optionally substituted with C 3-6 cycloalkyl, (C l-4 alkoxy)carbonyl, halogen, cyano, a 5- or 6-membered heterocyclic ring or optionally halo- or C 1-4 alkyl- substituted phenyl; C 3-6 cycloalkyl; C 3-6 alkenyl; or phenyl optionally substituted with halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, cyano or nitro; each of R 7 and R 8 , which may be the same or different, is hydrogen; C 1-6 alkyl optionally substituted with hydroxy, halogen, cyano, (C 1-4 alkoxy)carbonyl, C 1-4 alkox y or C 3-6 cycloalkyl; Cl-4 alkox y ; C 3-6 alkenyl; C 3-6 alkynyl; C 3-6 cycloalkyl; (C 1-6 alkane)sulphonyl;hydroxy; or phenyl or benzyl optionally ring-substituted by halogen, C 1-4 alkyl, C 1-4 alkox y, C 1-4 alk y lthio, (C 1-4 alkoxy)carbonyl, cyano or nitro; or R 7 or R 8 together with the nitrogen atom to which they are bound form a 5- or 6-membered heterocyclic ring optionally containing a further hetero atom; R 9 is hydrogen, C 1-4 alkyl, phenyl or benzyl; each of R 10 and R 11 , which may be the same or different, is hydrogen; C 1-4 alkyl; (C l-4 alkoxy) (C l-4 alkyl); C 2-6 alkanoyl; or benzoyl or phenyl optionally substituted with halogen, C 1-4 alkyl or C 1-4 alkoxy, or R 10 and R 11 together with the nitrogen atom to which they are bound for a 5- or 6-membered heterocyclic ring optionally containing a further hetero atom; R 3 is optionally halo-, haloalkyl- haloalkoxy- nitro-, cyano-, hydroxy-, amino-, acylamino- mono- or di- alkylamino-, C l-4 alkyl-, C l-4 alk oxy-, C 1-4 alkylthio-, C 1-4 alkylsulphinyl-, C 1-4 alkylsulphonyl-, C 2-6 alkenyl-, carboxy-, C l-4 alkoxycarbonyl- or carboxamido- substituted phenyl; and n is 0 or 1; or, when n is O, an acid addition salt thereof.
Claim 2
Dependent Claim
488 words
1 . A method of inducing tiller formation in a monocotyledonous plant, characterised by applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of general formula (I) : wherein R 1 is hydrogen, halogen, optionally halo- or acetoxy- substituted C l-4 alkyl, hydroxy, amino, phenyl or (C 1-5 alkoxy) carbonyl; R 2 is cyano, or a group of general formula -CO R 4 wherein R 4 is -O- l/m M m+ , -OR 5 , -SR 6 , -NR 7 R 8 or -NR 9 -NR 10 R 11 wherein M is an m-valent cation; R 5 is C 1-8 alkyl optionally substituted with halogen, hydroxy, cyano, C 1-4 alkoxy, C 1-4 alkylthio, carboxy, (C 1-4 alkoxy)carbonyl, C 3-6 cycloalkyl, amino, mono- or di- C 1-4 alkylamino, a 5- or 6-membered heterocyclic ring or optionally halo- or C 1-4 alkylsubstituted phenyl; C 3-6 cycloalkyl; optionally halo- substituted C 2-6 alkenyl; C 3-6 alkynyl; or phenyl optionally substituted with halogen, C 1-4 alkyl, C l-4 alkoxy, C l-4 alkylthio, cyano or nitro; R 6 is C 1-8 alkyl optionally substituted with C 3-6 cycloalkyl, (C l-4 alkoxy)carbonyl, halogen, cyano, a 5- or 6-membered heterocyclic ring or optionally halo- or C 1-4 alkyl- substituted phenyl; C 3-6 cycloalkyl; C 3-6 alkenyl; or phenyl optionally substituted with halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, cyano or nitro; each of R 7 and R 8 , which may be the same or different, is hydrogen; C 1-6 alkyl optionally substituted with hydroxy, halogen, cyano, (C 1-4 alkoxy)carbonyl, C 1-4 alkox y or C 3-6 cycloalkyl; Cl-4 alkox y ; C 3-6 alkenyl; C 3-6 alkynyl; C 3-6 cycloalkyl; (C 1-6 alkane)sulphonyl;hydroxy; or phenyl or benzyl optionally ring-substituted by halogen, C 1-4 alkyl, C 1-4 alkox y, C 1-4 alk y lthio, (C 1-4 alkoxy)carbonyl, cyano or nitro; or R 7 or R 8 together with the nitrogen atom to which they are bound form a 5- or 6-membered heterocyclic ring optionally containing a further hetero atom; R 9 is hydrogen, C 1-4 alkyl, phenyl or benzyl; each of R 10 and R 11 , which may be the same or different, is hydrogen; C 1-4 alkyl; (C l-4 alkoxy) (C l-4 alkyl); C 2-6 alkanoyl; or benzoyl or phenyl optionally substituted with halogen, C 1-4 alkyl or C 1-4 alkoxy, or R 10 and R 11 together with the nitrogen atom to which they are bound for a 5- or 6-membered heterocyclic ring optionally containing a further hetero atom; R 3 is optionally halo-, haloalkyl- haloalkoxy- nitro-, cyano-, hydroxy-, amino-, acylamino- mono- or di- alkylamino-, C l-4 alkyl-, C l-4 alk oxy-, C 1-4 alkylthio-, C 1-4 alkylsulphinyl-, C 1-4 alkylsulphonyl-, C 2-6 alkenyl-, carboxy-, C l-4 alkoxycarbonyl- or carboxamido- substituted phenyl; and n is 0 or 1; or, when n is O, an acid addition salt thereof.
Claim 3
Dependent Claim
20 words
A method according to claim 1 characterised in that, in the compound of general formula (I), R 1 is methyl.
Claim 4
Dependent Claim
42 words
A method according to claim 1 or 2 characterised in that, in the compound of general formula (I), R 3 is phenyl, o-, m- or p- fluoro-, chloro-, bromo-, cyano-, acetylamino-, amino-, nitro-, methyl-, trifluoromethyl- or methoxy-phenyl, 2,4-dichlorophenyl, 3,5-dibromophenyl, 3-bromo-4-aminophenyl or 3,5-dibromo-4-aminophenyl.
Claim 5
Dependent Claim
24 words
A method according to claim 1, 2 or 3 characterised in that, in the compound of general formula (I), R 2 group is alkoxycarbonyl.
Claim 6
Dependent Claim
22 words
A method according to claim 4 characterised in that, in the compound of general formula (I), R 2 is ethoxy- or n-propoxy-carbonyl.
Claim 7
Dependent Claim
23 words
A method according to claim 1 characterised in that the plant is a cereal plant, a forage or amenity grass or sugar cane.
Claim 8
Dependent Claim
29 words
A compound of general formula (I) wherein R l , R and R 3 are as defined in any one of claims 1 to 5 and n is 1.
Claim 9
Dependent Claim
86 words
A compound of general formula (I) wherein R 1 is as defined in claim 1 or 2 other than halogen or amino, R 2 is as defined in claim 1, 4 or 5, R 3 is halo-, haloalkyl-, haloalkoxy-, nitro-, cyano-, hydroxy-, amino-, acylamino-, mono- or di- alkylamino, C 1-4 alkyl-, C 1-4 alkoxy-, C 1-4 alkylthio-, C l-4 alkylsulphinyl-, C l - 4 alkylsulphonyl-, C 2-6 alkenyl-, carboxy-, C l-4 alkoxycarbonyl- or carboxamido- substituted phenyl, and n is O; or an acid addition salt thereof.
Claim 10
Dependent Claim
162 words
A process for preparing a compound according to claim 7 or 8, characterised by reacting a compound of general formula (II) wherein R 3 is as defined in claim 1 and X is halogen, with a compound of general formula (III) wherein R1 and R 2 are as defined in claim 1, or a salt thereof, to give a compound of general formula (I) wherein R 1 , R 2 and R 3 are as defined in claim 1 and n is O, and then if desired oxidising said compound to give a compound of general formula (I) wherein R 1 , R and R 3 are as defined in claim 1 and n is 1, and then if desired where the group R 2 in said reaction or oxidation product is not the group R 2 required, reacting in known manner said reaction or oxidation product to give a compound of general formula (I) wherein R 2 is the required group.
Claim 11
Dependent Claim
23 words
An agricultural composition characterised by comprising a compound of general formula (I) according to claim 7 or 8, and a diluent or carrier.
References Cited (Backward Citations)
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