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US 2008/0269059 A1Published application
Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their prepartion and their use
OwnerFrank Ziemer, Lothar Willms +4inventors
InventorsFrank Ziemer, Lothar Willms, Christopher Rosinger, Thomas Auler, Erwin Hacker, Udo Bickers
Life of this patent
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Abstract
Compounds of the formula (I), or salts thereof, in which R1 to R4 are as defined in formula (I) of claim 1 are suitable as useful-plant-protecting agents for reducing or preventing harmful effects of agrochemicals on the useful plants and their method of preparation are described.
Claims17
A method for protecting useful plants against phytotoxic side effects of agrochemicals, which comprises applying an effective amount of one or more of the formula (I) or salts thereof,
- in which
- R1 is a (C1-C6)-haloalkyl radical and
- R2 is hydrogen or halogen and
- R3 is hydrogen, (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
- where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
- where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- and
- R4 is (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
- where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
- where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- or
- R3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy
- and
- R4 is hydrogen or (C1-C4)-alkyl
- or
- R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio,
- or
- R3 and R4 together with the directly attached nitrogen atom are the group —N═CR 5-NR6R7 in which
- R5 is hydrogen or (C1-C6)-alkyl, and
- R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, or
- R6 and R7 together with the directly attached nitrogen atom form a five- to seven-membered heterocyclic ring,
- or
- R1 is a (C1-C6)-haloalkyl radical,
- R2 is halogen,
- R3 is hydrogen and
- R4 is hydrogen
- or
- R1 is a radical of the formula CF2C1, CF2H, CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3, or C(CH3)2F,
- R2 is hydrogen,
- R3 is hydrogen and
- R4 is hydrogen,
- before, after or simultaneously with the agrochemicals to the plants, parts of the plants, the plant seeds or seed of the plants.
31 more elements
A compound of the formula (I) or a salt thereof,
- in which
- R1 is a (C1-C6)-haloalkyl radical and
- R2 is hydrogen or halogen and
- R3 is hydrogen, (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
- where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl and [(C1-C4)-haloalkoxy]-carbonyl
- or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
- where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- and
- R4 is (C1-C16)-alkyl, (C2-C16)-alkenyl or (C2-C16)-alkynyl,
- where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl and [(C1-C4)-haloalkoxy]-carbonyl,
- or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
- where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]-amino, [(C1-C4)-alkoxy]-carbonyl, [(C1-C4)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted,
- or
- R3 is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy and
- R4 is hydrogen or (C1-C4)-alkyl
- or
- R3 and R4 together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio,
- or
- R3 and R4 together with the directly attached nitrogen atom are the group —N═CR5—NR6R7 in which
- R5 is hydrogen or (C1-C6)-alkyl, and
- R6, R7 independently of one another are hydrogen or (C1-C4)-alkyl, or
- R6 and R7 together with the directly attached nitrogen atom form a five- to seven-membered heterocyclic ring,
- or
- R1 is a (C1-C6)-haloalkyl radical,
- R2 is halogen,
- R3 is hydrogen and
- R4 is hydrogen
- or
- R1 is a radical of the formula CF2CF3, CF2CF2H, CF2CF2Cl, CFClCF3, CFHCF3, CF(CF3)2, CH(CF3)2, CF2CF2CF3, or C(CH3)2F,
- R2 is hydrogen,
- R3 is hydrogen and
- R4 is hydrogen.
29 more elements
Dependencies are inferred from the claim text.