AR077066A1 - Derivados de tiazolilpiperidina como fungicidas, procedimientos para su preparacion e intermediarios de sintesis utilizados en los mismos. - Google Patents
Derivados de tiazolilpiperidina como fungicidas, procedimientos para su preparacion e intermediarios de sintesis utilizados en los mismos.Info
- Publication number
- AR077066A1 AR077066A1 ARP100102067A ARP100102067A AR077066A1 AR 077066 A1 AR077066 A1 AR 077066A1 AR P100102067 A ARP100102067 A AR P100102067A AR P100102067 A ARP100102067 A AR P100102067A AR 077066 A1 AR077066 A1 AR 077066A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- haloalkyl
- substituents
- carbonyl
- alkoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000000417 fungicide Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- -1 carbonylthio Chemical group 0.000 abstract 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 13
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 13
- 125000001424 substituent group Chemical group 0.000 abstract 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 11
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 10
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 10
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 150000002367 halogens Chemical class 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 9
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 8
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 7
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 6
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 abstract 6
- 125000004414 alkyl thio group Chemical group 0.000 abstract 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 4
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical group [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 abstract 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 abstract 1
- 125000006769 halocycloalkoxy group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 abstract 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 abstract 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 abstract 1
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 abstract 1
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 abstract 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 abstract 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 abstract 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 abstract 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 230000003032 phytopathogenic effect Effects 0.000 abstract 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 abstract 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 abstract 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 abstract 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 abstract 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 abstract 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 abstract 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
Su uso para controlar hongos fitopatogenos daninos, y también procedimientos para preparar compuestos de la formula (1). Reivindicacion 1: Los compuestos de la formula (1), en la que los símbolos tienen los siguientes significados: A representa fenilo que puede contener hasta tres sustituyentes, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-4, haloalcoxi C1-4, OCH2OCH3, SH, alquiltio C1-4, haloalquiltio C1-6, CHO, COOH, (alcoxi C1-4)carbonilo, CONR3R4, CR3=NOR4, (alquil C1-4)carbonilo, (haloalquil C1-4)carbonilo, (alquil C1-4)carboniloxi, (alquil C1-4)carboniltio, alquilsulfinilo C1-4, haloalquilsulfinilo C1-4, alquilsulfonilo C1-4, haloalquilsulfonilo C1-4, NR3R4, NR3COR4, SF5, SO2NR3R4, alcoxialquilo C2-4 o 1- metoxiciclopropilo, o A representa un radical heteroaromático seleccionado entre el siguiente grupo: furan-2-ilo, furan-3-ilo, tiofen-2-ilo, tiofen-3-ilo, isoxazol-3-ilo, isoxazol-4-ilo, isoxazol-5-ilo, pirrol-1-ilo, pirrol-2-ilo, pirrol-3-ilo, oxazol-2-ilo, oxazol-4-ilo, oxazol-5-ilo, tiazol-2-ilo, tiazol-4-ilo, tiazol-5-ilo, isotiazol-3-ilo, isotiazol-4-ilo, isotiazol-5-ilo, pirazol-1-ilo, pirazol-3-ilo, pirazol-4-ilo, imidazol-1-ilo, imidazol-2-ilo, imidazol-4-ilo, piridin-2-ilo, piridin-3-ilo, piridin-4-ilo, piridazin-3-ilo, piridazin-4-ilo, pirimidin-2-ilo, pirimidin-4-ilo o pirimidin-5-ilo, que puede contener hasta tres sustituyentes, seleccionándose los sustituyentes independientemente entre sí entre la siguiente lista: sustituyentes en el carbono: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-C6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-4, haloalcoxi C1-4, OCH2OCH3, SH, alquiltio C1-4, haloalquiltio C1-6, CHO, COOH, (alcoxi C1-4)carbonilo, CONR3R4, CR3=NOR4, (alquil C1-4)carbonilo, (haloalquil C1-4)carbonilo, (alquil C1-4)carboniloxi, (alquil C1-4)carboniltio, alquilsulfinilo C1-4, haloalquilsulfinilo C1-4, alquilsulfonilo C1-4, haloalquilsulfonilo C1-4, NR3R4, NR3COR4, SF5, SO2NR3R6, alcoxialquilo C2-4 o 1- metoxiciclopropilo, sustituyentes en el nitrogeno: hidroxilo, ciano, NR3R4, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-6, halocicloalquilo C3-6, alquilcicloalquilo C4-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6 o haloalquinilo C2-6, G representa (C(R5)2)p en la que p = 1 o 2, o G representa NH, con la condicion de que G esté unido a un átomo de carbono de A, Y representa azufre u oxígeno, R1 representa hidrogeno, alquilo C1-2, haloalquilo C1-2 o halogeno, n= 0 a 2, R2 representa alquilo C1-8, haloalquilo C1-4, alquenilo C2-6, alquinilo C2-6, adamantan-1-ilo o adamantan2-ilo, o R2 representa cicloalquilo C3-10 sin sustituir o sustituido, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: ciano, halogeno, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, fenilo, hidroxilo, oxo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, alquiniloxi C2-6, alquiltio C1-6 o haloalquiltio C1-6, o R2 representa cicloalquenilo C5-10 sin sustituir o sustituido, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: ciano, halogeno, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, fenilo, hidroxilo, oxo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, alquiniloxi C2-6, alquiltio C1-6 o haloalquiltio C1-6, o R2 representa fenilo sin sustituir o sustituido, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, halocicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, cicloalcoxialquilo C4-10, alquenilo C2-6, haloalquenilo C2-6, cicloalquenilo C3-8, halocicloalquenilo C3-8, alquinilo C2-6, haloalquinilo C2-6, alcoxialquilo C2-6, haloalcoxialquilo C2-6, alcoxialcoxialquilo C3-8, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-6, alcoxialcoxi C2-6, haloalcoxi C1-6, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C2-6, haloalquiniloxi C2-6, cicloalcoxi C3-6, cicloalquiloxi C3-6, halocicloalcoxi C3-6, cicloalquilalquiloxi C4-10, NR3R4, SH, SF5, alquiltio C1-6, haloalquiltio C1-6, cicloalquiltio C3-6, CHO, COOH, (alcoxi C1-6)carbonilo, CONR3R4, CR3=NOR4, (alquil C1-6)carbonilo, (haloalquil C1-6)carbonilo, (alquil C1-6)carboniloxi, (haloalquil C1-6)carboniloxi, (alquil C1-6)carboniltio, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, NR3COR4 o SO2NR3R4, o R2 representa naftilo o indenilo sin sustituir o sustituido, saturado o parcial o completamente insaturado, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-6, haloalcoxi C1-6, alqueniloxi C2-6, alquiniloxi C2-6, alquiltio C1-6 o haloalquiltio C1-6, o R2 representa un radical heteroarilo de 5 o 6 miembros sin sustituir o sustituido, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: sustituyentes en el carbono. ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-4, haloalcoxi C1-4, OCH2OCH3, SH, alquiltio C1-4, haloalquiltio C1-6, COOH, (alcoxi C1-4)carbonilo, CONR3R4, (alquil C1-4)carbonilo, (haloalquil C1-4)carbonilo, (alquil C1-4)carboniloxi, (alquil C1-4)carboniltio, alquilsulfinilo C1-4, haloalquilsulfinilo C1-4, alquilsulfonilo C1-4, haloalquilsulfonilo C1-4, NR3R4, NR3COR4, SF5, SO2NR3R4, alcoxialquilo C2-4 o 1- metoxiciclopropilo, sustituyentes en el nitrogeno: ciano, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, alquilcicloalquilo C4-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6 o fenilo, o R2 representa heteroarilo de 5 o 6 miembros, benzocondensado, sin sustituir o sustituido, en el que los sustituyentes se seleccionan independientemente entre sí entre la siguiente lista: sustituyentes en el carbono: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-4, haloalcoxi C1-4, OCH2OCH3, SH, alquiltio C1-4, haloalquiltio C1-6, COOH, (alcoxi C1-4)carbonilo, CONR3R4, (alquil C1-4)carbonilo, (haloalquil C1-4)carbonilo. (alquil C1-4)carboniloxi, (alquil C1-4)carboniltio, alquilsulfinilo C1-4, haloalquilsulfinilo C1-4, alquilsulfonilo C1-4, haloalquilsulfonilo C1-4, NR3R4, NR3COR4, SF5, SO2NR3R4, alcoxialquilo C2-4 o 1-metoxiciclopropilo, sustituyentes en el nitrogeno: ciano, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, alquilcicloalquilo C4-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6 o fenilo, o R2 representa heterociclilo C5-15 sin sustituir o sustituido, en el que los sustituyentes posibles se seleccionan independientemente entre sí entre la siguiente lista: sustituyentes en el carbono: ciano, nitro, halogeno, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, cicloalquilalquilo C4-10, alquilcicloalquilo C4-10, alquilcicloalquilalquilo C5-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, tri(alquil C1-4)sililo, bencilo, fenilo, hidroxilo, alcoxi C1-4, haloalcoxi C1-4, OCH2OCH3, SH, alquiltio C1-4, haloalquiltio C1-6, COOH, (alcoxi C1-4)carbonilo, CONR3R4, (alquil C1-4)carbonilo, (haloalquil C1-4)carbonilo, (alquil C1-4)carboniloxi, (alquil C1-4)carboniltio, alquilsulfinilo C1- 4, haloalquilsulfinilo C1-4, alquilsulfonilo C1-4, haloalquilsulfonilo C1-4, NR3R4, NR3COR4, SF5, SO2NR3R4, alcoxialquilo C2-4 o 1- metoxiciclopropilo, sustituyentes en el nitrogeno: ciano, alquilo C1-6, haloalquilo C1-3, cicloalquilo C3-6, halocicloalquilo C3-6, alquilcicloalquilo C4-10, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6 o fenilo, R3, R4 independientemente entre sí representan hidrogeno, alquilo C1-4, haloalquilo C1-3, cicloalquilo C3-6, bencilo o fenilo, R5 son iguales o diferentes y representan independientemente entre si hidrogeno, alquilo C1-2 o haloalquilo C1-2, y también sales agroquímicamente activas de los mismos. Reivindicacion 9: Los compuestos de la formula (6) en la que PG representa acetilo, alcoxicarbonilo C1-4, bencilo o benciloxicarbonilo, Wa representa bromo o yodo, R1 tiene los significados dados en la reivindicacion 1, y también sales de los mismos. Reivindicacion 10: Los compuestos de la formula (4) en la que PG representa acetilo, alcoxicarbonilo C1-4, bencilo o benciloxicarbonilo, R1 y R2 tienen los significados dados en la reivindicacion 1, y también sales de los mismos, excepto para el compuesto 4-[4-({[4-metilsulfonil)feni
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EP09163473A EP2272846A1 (de) | 2009-06-23 | 2009-06-23 | Thiazolylpiperidin Derivate als Fungizide |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011076699A1 (de) | 2009-12-21 | 2011-06-30 | Bayer Cropscience Ag | Bis(difluormethyl)pyrazole als fungizide |
KR20130100903A (ko) | 2010-04-28 | 2013-09-12 | 바이엘 크롭사이언스 아게 | 살진균제로서의 케토헤테로아릴피페리딘 및 케토헤테로아릴피페라진 유도체 |
EP2576539B1 (de) | 2010-05-27 | 2017-12-13 | Bayer CropScience AG | Pyridinylcarbonsäure derivate als fungizide |
CA2815716C (en) | 2010-10-27 | 2019-06-11 | Bayer Intellectual Property Gmbh | Heteroaryl piperidine and heteroaryl piperazine derivatives as fungicides |
MX352307B (es) | 2011-02-01 | 2017-11-17 | Bayer Ip Gmbh | Derivados de heteroarilpiperidina y -piperazina como fungicidas. |
BR112014005989B1 (pt) | 2011-09-15 | 2019-11-05 | Bayer Ip Gmbh | compostos fungicidas piperidina-pirazoles, seus usos, método e composição para controlar fungos fitopatogênicos prejudiciais, e método para produzir composições |
US9266876B2 (en) | 2012-02-02 | 2016-02-23 | Actelion Pharmaceuticals Ltd. | 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives |
MX355542B (es) | 2012-08-30 | 2018-04-20 | Bayer Cropscience Ag | Procedimiento de descarboxilacion de derivados de acido 3,5-bis(haloalquil)-pirazol-4-carboxilico. |
TWI630205B (zh) | 2013-07-22 | 2018-07-21 | 瑞士商愛杜西亞製藥有限公司 | 1-(哌-1-基)-2-([1,2,4]三唑-1-基)-乙酮衍生物 |
AR099789A1 (es) | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
WO2016024350A1 (ja) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | 縮合11員環化合物及びそれらを含有する農園芸用殺菌剤 |
AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
AU2016207988B2 (en) | 2015-01-15 | 2019-08-15 | Idorsia Pharmaceuticals Ltd | Hydroxyalkyl-piperazine derivatives as CXCR3 receptor modulators |
WO2017138068A1 (ja) | 2016-02-08 | 2017-08-17 | 株式会社エス・ディー・エス バイオテック | 1,2-ベンゼンジメタノール化合物の製造方法 |
KR102605762B1 (ko) | 2016-02-08 | 2023-11-27 | 고완 크롭 프로텍션 리미티드 | 살균성 조성물 |
CN106083707B (zh) * | 2016-06-01 | 2018-10-26 | 温州大学 | 一种非对称杂芳基硫醚的合成方法 |
CN107646855B (zh) * | 2017-08-02 | 2020-07-07 | 浙江工业大学 | 一种含哌啶噻唑类化合物在制备杀菌剂中的应用及其制备方法 |
WO2021085550A1 (ja) | 2019-11-01 | 2021-05-06 | ユニマテック株式会社 | 含フッ素ピリミジン化合物およびその製造方法 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4272417A (en) | 1979-05-22 | 1981-06-09 | Cargill, Incorporated | Stable protective seed coating |
US4245432A (en) | 1979-07-25 | 1981-01-20 | Eastman Kodak Company | Seed coatings |
WO1987005296A1 (en) | 1986-03-07 | 1987-09-11 | Pfizer Inc. | 2-[(2-pyridyl)methylsulfinyl]thienoimidazoles and related compounds as antiulcer agents |
US4808430A (en) | 1987-02-27 | 1989-02-28 | Yazaki Corporation | Method of applying gel coating to plant seeds |
GB8810120D0 (en) | 1988-04-28 | 1988-06-02 | Plant Genetic Systems Nv | Transgenic nuclear male sterile plants |
DE69636637T2 (de) | 1995-04-20 | 2007-08-23 | Basf Ag | Auf basis ihrer struktur entworfene herbizid-resistente produkte |
US5876739A (en) | 1996-06-13 | 1999-03-02 | Novartis Ag | Insecticidal seed coating |
US6503904B2 (en) | 1998-11-16 | 2003-01-07 | Syngenta Crop Protection, Inc. | Pesticidal composition for seed treatment |
US6660690B2 (en) | 2000-10-06 | 2003-12-09 | Monsanto Technology, L.L.C. | Seed treatment with combinations of insecticides |
US20020134012A1 (en) | 2001-03-21 | 2002-09-26 | Monsanto Technology, L.L.C. | Method of controlling the release of agricultural active ingredients from treated plant seeds |
EP1521747B1 (en) * | 2002-07-15 | 2018-09-05 | Symphony Evolution, Inc. | Receptor-type kinase modulators and methods of use |
FR2856685B1 (fr) * | 2003-06-25 | 2005-09-23 | Merck Sante Sas | Derives de thiazolylpiperidine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
PE20060426A1 (es) | 2004-06-02 | 2006-06-28 | Schering Corp | DERIVADOS DE ACIDO TARTARICO COMO INHIBIDORES DE MMPs, ADAMs, TACE Y TNF-alfa |
DE102005031583A1 (de) * | 2005-07-06 | 2007-01-25 | Bayer Cropscience Gmbh | Verfahren zur Herstellung von von 3-Arylmethylthio- und 3-Heteroarylmethylthio-4,5-dihydro-isoxazolin-Derivaten |
TW200738701A (en) | 2005-07-26 | 2007-10-16 | Du Pont | Fungicidal carboxamides |
ATE430744T1 (de) * | 2005-08-18 | 2009-05-15 | Hoffmann La Roche | Thiazolylpiperidin-derivate nützlich als h3 rezeptor modulatoren |
WO2007024782A2 (en) | 2005-08-24 | 2007-03-01 | Pioneer Hi-Bred International, Inc. | Compositions providing tolerance to multiple herbicides and methods of use thereof |
CN102766652B (zh) | 2005-08-31 | 2015-07-29 | 孟山都技术有限公司 | 编码杀虫蛋白的核苷酸序列 |
CN101443330B (zh) | 2006-06-13 | 2012-12-19 | 上海海和药物研究开发有限公司 | 杂环非核苷类化合物及其制备方法、药物组合物和作为抗病毒抑制剂的用途 |
DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
US7638541B2 (en) * | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
WO2008091594A2 (en) | 2007-01-24 | 2008-07-31 | E. I. Du Pont De Nemours And Company | Fungicidal mixtures |
JP5337711B2 (ja) * | 2007-01-25 | 2013-11-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性アミド |
TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
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PE20121047A1 (es) | 2012-08-02 |
EA201270059A1 (ru) | 2012-08-30 |
ZA201109365B (en) | 2013-02-27 |
CA2766199A1 (en) | 2010-12-29 |
CL2011003180A1 (es) | 2012-06-15 |
WO2010149275A1 (de) | 2010-12-29 |
KR20120050434A (ko) | 2012-05-18 |
CN102459254A (zh) | 2012-05-16 |
TW201111377A (en) | 2011-04-01 |
CN104059059A (zh) | 2014-09-24 |
CO6480909A2 (es) | 2012-07-16 |
EP2272846A1 (de) | 2011-01-12 |
IL216344A0 (en) | 2012-01-31 |
EP2445907A1 (de) | 2012-05-02 |
US20110046178A1 (en) | 2011-02-24 |
US20130090476A1 (en) | 2013-04-11 |
US20130090477A1 (en) | 2013-04-11 |
MX2011013706A (es) | 2012-02-22 |
BRPI1014077A8 (pt) | 2016-05-24 |
JP2012530734A (ja) | 2012-12-06 |
BRPI1014077A2 (pt) | 2015-08-25 |
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