AR082828A1 - N-(tetrazol-5-il)- y n-(triazol-5-il)arilcarboxamidas utiles como herbicidas, composiciones herbicidas que las contienen y un procedimiento para controlar el crecimiento de plantas indeseadas - Google Patents
N-(tetrazol-5-il)- y n-(triazol-5-il)arilcarboxamidas utiles como herbicidas, composiciones herbicidas que las contienen y un procedimiento para controlar el crecimiento de plantas indeseadasInfo
- Publication number
- AR082828A1 AR082828A1 ARP110103184A ARP110103184A AR082828A1 AR 082828 A1 AR082828 A1 AR 082828A1 AR P110103184 A ARP110103184 A AR P110103184A AR P110103184 A ARP110103184 A AR P110103184A AR 082828 A1 AR082828 A1 AR 082828A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- halo
- heterocyclyl
- cycloalkyl
- heteroaryl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title 2
- 230000002363 herbicidal effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 25
- -1 tetrazol-4-yl Chemical group 0.000 abstract 15
- 125000000623 heterocyclic group Chemical group 0.000 abstract 11
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 150000002367 halogens Chemical group 0.000 abstract 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 7
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 5
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000004043 oxo group Chemical group O=* 0.000 abstract 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 abstract 3
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 abstract 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract 3
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 abstract 3
- 101150111293 cor-1 gene Proteins 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 abstract 2
- RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- NWBNORAVIXIZTL-UHFFFAOYSA-N nitro thiocyanate Chemical compound [O-][N+](=O)SC#N NWBNORAVIXIZTL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- HCUOEKSZWPGJIM-YBRHCDHNSA-N (e,2e)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N/O)\C(N)=O HCUOEKSZWPGJIM-YBRHCDHNSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 101001109689 Homo sapiens Nuclear receptor subfamily 4 group A member 3 Proteins 0.000 abstract 1
- 101000598778 Homo sapiens Protein OSCP1 Proteins 0.000 abstract 1
- 101001067395 Mus musculus Phospholipid scramblase 1 Proteins 0.000 abstract 1
- 102100022673 Nuclear receptor subfamily 4 group A member 3 Human genes 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Chemical group SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 abstract 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
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- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
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- Environmental Sciences (AREA)
- Molecular Biology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Reivindicación 1: Una N-(tetrazol-4-il)- o N-(triazol-3-il)arilcarboxamida de la fórmula (1) o una sal de la misma en la que A representa N o CY; B representa N o CH; X representa nitro, halógeno, ciano, formilo, tiocianato, alquilo C1-6, halo-alquilo C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, halo-alquinilo C3-6, cicloalquilo C3-6, halo-cicloalquilo C3-6, cicloalquil C3-6-alquilo C1-6, halo-cicloalquil C3-6-alquilo C1-6, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, alquil C1-6-S(O)nR2, alquil C1-6-OR1, alquil C1-6-OCOR1, alquil C1-6-OSO2R2, alquil C1-6-CO2R1, alquil C1-6-SO2OR1, alquil C1-6-CON(R1)2, alquil C1-6-SO2N(R1)2, alquil C1-6-NR1COR1, alquil C1-6-NR1SO2R2, NR1R2, P(O)(OR5)2, CH2P(O)(OR5)2, alquil C1-6-heteroarilo, alquil C1-6-heterociclilo, en los que cada uno de los dos últimos radicales mencionados está sustituido con s radicales halógeno, alquilo C1-6, halo-alquilo C1-6, S(O)n-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, y en los que el heterociclilo tiene de 0 a 2 grupos oxo; Y representa hidrógeno, nitro, halógeno, ciano, tiocianato, alquilo C1-6, halo-alquilo C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, halo-alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, halocicloalquilo C3-6, cicloalquil C3-6-alquilo C1-6, halo-cicloalquil C3-6-alquilo C1-6, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, CO(NOR1)R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, alquil C1-6-S(O)nR2, alquil C1-6-OR1, alquil C1-6-OCOR1, alquil C1-6-OSO2R2, alquil C1-6-CO2R1, alquil C1-6-CN, alquil C1-6-SO2OR1, alquil C1-6-CON(R1)2, alquil C1-6-SO2N(R1)2, alquil C1-6-NR1COR1, alquil C1-6-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, alquil C1-6-fenilo, alquil C1-6-heteroarilo, alquil C1-6-heteroarilo, alquil C1-6-heterociclilo, fenilo, heteroarilo o heterociclilo, en los que cada uno de los 6 últimos radicales mencionados está sustituido con s radicales del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, cicloalquilo C3-6, S(O)n-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, alcoxi C1-6-alquilo C1-4 y cianometilo, y en los que el heterociclilo tiene de 0 a 2 grupos oxo; Z representa halógeno, ciano, tiocianato, halo-alquilo C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, halo-alquinilo C2-6, cicloalquilo C3-6, halo-cicloalquilo C3-6, cicloalquil C3-6-alquilo C1-6, halo-cicloalquil C3-6-alquilo C1-6, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, alquil C1-6-S(O)nR2, alquil C1-6-OR1, alquil C1-6-OCOR1, alquil C1-6-OSO2R2, alquil C1-6-CO2R1, alquil C1-6-SO2OR1, alquil C1-6-CON(R1)2, alquil C1-6-SO2N(R1)2, alquil C1-6-NR1COR1, alquil C1-6-NR1SO2R2, N(R1)2, P(O)(OR5)2, heteroarilo, heterociclilo o fenilo, en los que cada uno de los tres últimos radicales mencionados está sustituido con s radicales del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, cicloalquilo C3-6, S(O)n-alquilo C1-6, alcoxi C1-6 y halo-alcoxi C1-6, y en los que el heterociclilo tiene de 0 a 2 grupos oxo, o Z también puede representar hidrógeno, alquilo C1-6 o alcoxi C1-6 si Y representa el radical S(O)nR2; R representa alquilo C1-6, cicloalquilo C3-7, halo-alquilo C1-6, alquenilo C2-6, halo-alquenilo C2-6, alquinilo C2-6, halo-alquinilo C2-6, CH2R6, heteroarilo, heterociclilo o fenilo, en los que cada uno de los tres últimos radicales mencionados está sustituido con s radicales del grupo que consiste en halógeno, nitro, ciano, alquilo C1-6, halo-alquilo C1-6, cicloalquilo C3-6, S(O)n-alquilo C1-6, alcoxi C1-6, halo-alcoxi C1-6, alcoxi C1-6-alquilo C1-4; R1 representa hidrógeno, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, halocicloalquilo C3-6, alquil C1-6-O-alquilo C1-6, cicloalquil C3-6-alquilo C1-6, fenilo, fenil-alquilo C1-6, heteroarilo, alquil C1-6-heteroarilo, heterociclilo, alquil C1-6-heterociclilo, alquil C1-6-O-heteroarilo, alquil C1-6-O-heterociclilo, alquil C1-6-NR3-heteroarilo, alquil C1-6-NR3-heterociclilo, en los que cada uno de los 21 últimos radicales mencionados está sustituido con s radicales del grupo que consiste en ciano, halógeno, nitro, tiocianato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4; CO2R3, COSR4, CON(R3)2 y alcoxi C1-4-alcoxicarbonilo C2-6, y en los que el heterociclilo tiene de 0 a 2 grupos oxo; R2 representa alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C3-6, halocicloalquilo C3-6, alquil C1-6-O-alquilo C1-6, cicloalquil C3-6-alquilo C1-6, fenilo, fenil-alquilo C1-6, heteroarilo, alquil C1-6-heteroarilo, heterociclilo, alquil C1-6-heterociclilo, alquil C1-6-O-heteroarilo, alquil C1-6-O-heterociclilo, alquil C1-6-NR3-heteroarilo, alquil C1-6-NR3-heterociclilo, en los que cada uno de los 21 últimos radicales mencionados está sustituido con s radicales del grupo que consiste en ciano, halógeno, nitro, tiocianato, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 y alcoxi C1-4-alcoxicarbonilo C2-6, y en los que el heterociclilo tiene de 0 a 2 grupos oxo; R3 representa hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6 o cicloalquil C3-6-alquilo C1-6; R4 representa alquilo C1-6, alquenilo C2-6 o alquinilo C2-6; R5 representa metilo o etilo; R6 representa acetoxi, acetamido, N-metilacetamido, benzoíloxi, benzamido, N-metilbenzamido, metoxicarbonilo, etoxicarbonilo, benzoílo, metilcarbonilo, piperidinilcarbonilo, morfolinilcarbonilo, trifluorometilcarbonilo, aminocarbonilo, metilaminocarbonilo, dimetilaminocarbonilo, alcoxi C1-6, cicloalquilo C3-6 o representa heteroarilo, heterociclilo o fenilo, cada uno de los cuales está sustituido con s radicales del grupo que consiste en metilo, etilo, metoxi, trifluorometilo y halógeno; n representa 0, 1 ó 2; s representa 0, 1, 2 ó 3; con la condición de que ninguno de X y Z represente cloro y B no represente nitrógeno si R representa n-propilo.
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