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AR076430A1 - DERIVATIVES OF TRIAZOL AS FUNGICIDES IN AGRICULTURAL COMPOSITIONS AND THEIR USE AS ANTIVIRALS AND IN THE TREATMENT OF CANCER AND INTERMEDIARIES TO PRODUCE THEM - Google Patents

DERIVATIVES OF TRIAZOL AS FUNGICIDES IN AGRICULTURAL COMPOSITIONS AND THEIR USE AS ANTIVIRALS AND IN THE TREATMENT OF CANCER AND INTERMEDIARIES TO PRODUCE THEM

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Publication number
AR076430A1
AR076430A1 ARP100101400A ARP100101400A AR076430A1 AR 076430 A1 AR076430 A1 AR 076430A1 AR P100101400 A ARP100101400 A AR P100101400A AR P100101400 A ARP100101400 A AR P100101400A AR 076430 A1 AR076430 A1 AR 076430A1
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Argentina
Prior art keywords
hydrogen
het
alkyl
phenyl
chloropyridin
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ARP100101400A
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Spanish (es)
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Basf Se
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Publication of AR076430A1 publication Critical patent/AR076430A1/en

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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
    • C07D403/08—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 carbon chain containing alicyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D401/08—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 carbon chain containing alicyclic 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
    • C07D417/08—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 carbon chain containing alicyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Composiciones agrícolas que los contienen, a su uso como fungicidas y a compuestos intermediarios utilizados en los métodos para producirlos. Reivindicacion 1: Compuestos de triazol caracterizados porque tienen las formulas (1) y (2) en donde Het es un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o aromático que contiene 1, 2 o 3 heteroátomos seleccionados de N, O y S como miembros del anillo, en donde el anillo heterocíclico puede llevar 1, 2, 3 o 4 sustituyentes L1; cada L1 se selecciona en forma independiente de halogeno, C1-10-alquilo, C1-10-haloalquilo, C1-10-alcoxi y C1-10-haloalcoxi; R1 y R2, independientemente uno del otro, se seleccionan de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C1-10-alcoxi y C1-10-haloalcoxi; R3 se selecciona de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C1-10-alcoxi y C1-10-haloalcoxi; R4 se selecciona de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C2-10-alquenilo, C2-10-haloalquenilo, C2-10-alquinilo, C2-10-haloalquinilo, C3-10-cicloalquilo, C3-10-halocicloalquilo, fenilo, fenil-C1-4-alquilo, donde la porcion de fenilo en los 2 ultimos radicales mencionados puede llevar 1, 2, 3, 4 o 5 sustituyentes R8, y un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o aromático que contiene 1, 2 o 3 heteroátomos seleccionados de N, O y S como miembros del anillo, en donde el anillo heterocíclico puede llevar 1, 2 o 3 sustituyentes R8, o, en el caso de que n sea 0, también se puede seleccionar de -C(=O)R5, -C(=S)R5, -S(O)2R5, -CN, -P(=Q)R6R7, M y un grupo de la formula (3) en donde Het, R1, R2 y R3 son como se definen en las formulas 1 y 2; y es el punto de union con el resto de la molécula; R4a se selecciona de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C2-10-alquenilo, C2-10-haloalquenilo, C2-10-alquinilo, C2-10-haloalquinilo, C3-10-cicloalquilo, C3-10-halocicloalquilo, fenilo, fenil-C1-4-alquilo, donde la porcion de fenilo en los 2 ultimos radicales mencionados puede llevar 1, 2, 3, 4 o 5 sustituyentes R8, un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o aromático que contiene 1, 2 o 3 heteroátomos seleccionados de N, O y S como miembros del anillo, en donde el anillo heterocíclico puede llevar 1, 2 o 3 sustituyentes R8, -C(O)R5, -C(=S)R5, -S(O)2R5, -CN, -P(=Q)R6R7 y M; R5 se selecciona de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C1-10-alcoxi, C1-10-haloalcoxi, C1-10-aminoalquilo, C3-10-cicloalquilo, C3-10- halocicloalquilo, fenilo, fenil-C1-4-alquilo, fenoxi, donde la porcion de fenilo en los 3 ultimos radicales mencionados puede llevar 1, 2, 3, 4 o 5 sustituyentes R8, un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o aromático que contiene 1, 2 o 3 heteroátomos seleccionados de N, O y S como miembros del anillo, en donde el anillo heterocíclico puede llevar 1, 2 o 3 sustituyentes R8, y NR9R10; R6 y R7, independientemente uno del otro, se seleccionan de C1-10-alquilo, C1-10-haloalquilo, C2-10-alquenilo, C2-10-haloalquenilo, C2-10-alquinilo, C2-10- haloalquinilo, C3-10-cicloalquilo, C3-10-halocicloalquilo, C1-10-alcoxi, C1-10-haloalcoxi, C1-4-alcoxi-C1-10-alquilo, C1-4-alcoxi-C1-10-alcoxi, C1-10-alquiltio, C1-10-haloalquiltio, C2-10-alqueniloxi, C2-10-alqueniltio, C2-10-alquiniloxi, C2-10-alquiniltio, C3-10-cicloalcoxi, C3-10-cicloalquiltio, fenilo, fenil-C1-4-alquilo, fenoxi, feniltio, fenil-C1-4-alcoxi, y NR11 R12; cada R8 se selecciona independientemente de halogeno, CN, nitro, C1-4-alquilo, C1-4-haloalquilo, C1-4-alcoxi, C1-4-haloalcoxi y NR13R14; R9 se selecciona de hidrogeno y C1-8-alquilo; R10 se selecciona de hidrogeno, C1-8-alquilo, fenilo, y fenil-C1-4-alquilo; o R9 y R10 en forma conjunta, forman un puente lineal de C4- o C5-alquileno o un grupo -CH2CH2OCH2CH2- o -CH2CH2NR15CH2CH2-; R11 se selecciona de hidrogeno y C1-8-alquilo; R12 se selecciona de hidrogeno, C1-8-alquilo, fenilo, y fenil-C1-4-alquilo; o R11 y R12 en forma conjunta, forman un puente lineal de C4- o C5-alquileno o un grupo -CH2CH2OCH2CH2- o-CH2CH2NR15CH2CH2-; R13 independientemente de cada acontecimiento, se selecciona de hidrogeno y C1-8-alquilo; R14 independientemente de cada acontecimiento, se selecciona de hidrogeno, C1-8-alquilo, fenilo, y fenil-C1-4-alquilo; o R13 y R14 en forma conjunta, forman un puente lineal de C4- o C5-alquileno o un grupo -CH2CH2OCH2CH2- o-CH2CH2NR15CH2CH2-; R15 independientemente de cada acontecimiento, se selecciona de hidrogeno y C1-4-alquilo; Q es O o S; M es un equivalente del cation metálico o un cation amonio de la formula (NRaRbRcRd)+, en donde Ra, Rb, Rc y Rd, independientemente uno del otro, se seleccionan de hidrogeno, C1-10-alquilo, fenilo y bencilo, en donde la porcion de fenilo en los 2 ultimos radicales mencionados puede llevar 1, 2 o 3 sustituyentes independientemente seleccionados de halogeno, CN, nitro, C1-4-alquilo, C1-4-haloalquilo, C1-4-alcoxi, C1-4-haloalcoxi y NR13R14; n es 0, 1, 2 o 3; y ---- es un enlace simple o doble; y sus sales aceptables en la agricultura. Reivindicacion 15: Compuestos caracterizados porque tienen la formula (4) en donde R1, R2, R3, y Het son como se definen en cualquiera de las reivindicaciones 1 a 7; a excepcion de los compuestos, en donde R1, R2 y R3 son hidrogeno, Het es 4-cloropiridin-3-ilo y ---- es un enlace simple; R1 y R2 son metilo, R3 es hidrogeno, Het es 4-cloropiridin-3-ilo, 2-clorotiazol-2-ilo, 2-clorotien-2-ilo, 3,5-dicloropiridin-4-ilo, 2-clorofuran-5-ilo, 2-bromo-tien-5-ilo, 3-bromo-tien-5-ilo, 4-cloropiridin-2-ilo o furan-2-ilo y es un enlace simple; R1 es isopropilo, R2 y R3 son hidrogeno, Het es 4-cloropiridin-3-ilo o 3,5-dicloropiridin-4-ilo y ---- es un enlace simple; R1 es etilo, R2 y R3 son hidrogeno, Het es 4-cloropiridin-2-ilo, 4-cloropiridin-3-ilo, 4-trifluoropiridin-2-ilo, 4-trifluoropiridin-3-ilo, 4-fluoropiridin-3-ilo o 3-cloropiridazin-6-ilo y ---- es un enlace simple; R1 es metilo, R2 y R3 son hidrogeno, Het es 4-cloropiridin-3-ilo y ---- es un enlace simple; R1 es propilo, R2 y R3 son hidrogeno, Het es 4-cloropiridin-3-ilo y ---- es un enlace simple; R1 es isobutilo, R2 y R3 son hidrogeno, Het es 4-cloropiridin-3-ilo y ---- es un enlace simple; R1, R2 y R3 son hidrogeno, Het es 4-tetrahidropiranilo, 2-piridilo, 3-piridilo, 4-piridilo, 2-furilo, 2-tienilo, 3-tienilo o 5-imidazolilo y ---- es un enlace doble; R1 y R2 son metilo, R3 es hidrogeno, Het es 2-furilo y ---- es un enlace doble. Reivindicacion 16: Compuestos caracterizados porque tienen la formula (5) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7; a excepcion de los compuestos, en donde R1, R2 y R3 son hidrogeno, y Het es 4-cloropiridin-3-ilo; R1 y R2 son metilo, R3 es hidrogeno y Het es 4-cloropiridin-3-ilo, 2-clorotiazol-2-ilo, 2-clorotien-2-ilo, 3,5-dicloropiridin-4-ilo, 2-clorofuran-5-ilo, 2-bromo-tien-5-ilo, 3- bromo-tien-5-ilo, 4-cloropiridin-2-ilo o furan-2-ilo; R1 es isopropilo, R2 y R3 son hidrogeno y Het es 4-cloropiridin-3-ilo o 3,5-dicloropiridin-4-ilo; R1 es etilo, R2 y R3 son hidrogeno y Het es 4-cloropiridin-2-ilo, 4-cloropiridin-3-ilo, 4-trifluoropiridin-2-ilo, 4-trifluoropiridin-3-ilo, 4-fluoropiridin-3-ilo o 3-cloropiridazin-6-ilo; R1 es metilo, R2 y R3 son hidrogeno y Het es 4-cloropiridin-3-ilo; R1 es propilo, R2 y R3 son hidrogeno y Het es 4-cloropiridin-3-ilo; R1 es isobutilo, R2 y R3 son hidrogeno y Het es 4-cloropiridin-3-ilo. Reivindicacion 17: Compuestos caracterizados porque tienen la formula (6) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7; a excepcion de los compuestos, en donde R1, R2 y R3 son hidrogeno, Het es 3-piridilo, 2-furilo o 3-tienilo y ---- es un enlace doble. Reivindicacion 18: Compuestos caracterizados porque tienen la formula (7) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7. Reivindicacion 19: Compuestos caracterizados porque tienen la formula (8) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7. Reivindicacion 20: Compuestos caracterizados porque tienen la formula (9) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7; y R14 es H o C(O)OR15, en donde R15 se selecciona de hidrogeno, C1-10-alquilo, C1-10-haloalquilo, C3-10-cicloalquilo, C3-10-halocicloalquilo, fenilo, fenil-C1-4-alquilo, donde la porcion de fenilo en los 2 ultimos radicales mencionados puede llevar 1, 2, 3, 4 o 5 sustituyentes R8, y un anillo heterocíclico de 5 o 6 miembros saturado, parcialmente insaturado o aromático que contiene 1, 2 o 3 heteroátomos seleccionados de N, O y S como miembros del anillo, en donde el anillo heterocíclico puede llevar 1, 2 o 3 sustituyentes R8, en donde R8 es como se define en la reivindicacion 1. Reivindicacion 21: Compuestos caracterizados porque tienen la formula (10) en donde R1, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7 y R14 es como se define en la reivindicacion 18. Reivindicacion 22: Compuestos caracterizados porque tienen la formula (11) en donde R1, R2, R3 y Het son como se definen en cualquiera de las reivindicaciones 1 a 7.Agricultural compositions that contain them, for use as fungicides and intermediate compounds used in the methods to produce them. Claim 1: Triazole compounds characterized in that they have formulas (1) and (2) wherein Het is a saturated, partially unsaturated or aromatic 5 or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as members of the ring, wherein the heterocyclic ring may carry 1, 2, 3 or 4 substituents L1; each L1 is independently selected from halogen, C1-10-alkyl, C1-10-haloalkyl, C1-10-alkoxy and C1-10-haloalkoxy; R1 and R2, independently of each other, are selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C1-10-alkoxy and C1-10-haloalkoxy; R3 is selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C1-10-alkoxy and C1-10-haloalkoxy; R4 is selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C2-10-alkenyl, C2-10-haloalkenyl, C2-10-alkynyl, C2-10-haloalkynyl, C3-10-cycloalkyl, C3- 10-halocycloalkyl, phenyl, phenyl-C1-4-alkyl, where the portion of phenyl in the last 2 radicals mentioned may carry 1, 2, 3, 4 or 5 R8 substituents, and a saturated 5- or 6-membered heterocyclic ring, partially unsaturated or aromatic containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the heterocyclic ring may carry 1, 2 or 3 R8 substituents, or, where n is 0, You can also select from -C (= O) R5, -C (= S) R5, -S (O) 2R5, -CN, -P (= Q) R6R7, M and a group of the formula (3) in where Het, R1, R2 and R3 are as defined in formulas 1 and 2; and is the point of union with the rest of the molecule; R4a is selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C2-10-alkenyl, C2-10-haloalkenyl, C2-10-alkynyl, C2-10-haloalkynyl, C3-10-cycloalkyl, C3- 10-halocycloalkyl, phenyl, phenyl-C1-4-alkyl, where the portion of phenyl in the last 2 radicals mentioned may carry 1, 2, 3, 4 or 5 R8 substituents, a partially or saturated 6 or 6-membered heterocyclic ring unsaturated or aromatic containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the heterocyclic ring can carry 1, 2 or 3 substituents R8, -C (O) R5, -C (= S ) R5, -S (O) 2R5, -CN, -P (= Q) R6R7 and M; R5 is selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C1-10-alkoxy, C1-10-haloalkoxy, C1-10-aminoalkyl, C3-10-cycloalkyl, C3-10-halocycloalkyl, phenyl, phenyl-C1-4-alkyl, phenoxy, where the portion of phenyl in the last 3 radicals mentioned may carry 1, 2, 3, 4 or 5 R8 substituents, a saturated, partially unsaturated or aromatic 5 or 6 membered heterocyclic ring that it contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the heterocyclic ring can carry 1, 2 or 3 R8 substituents, and NR9R10; R6 and R7, independently of each other, are selected from C1-10-alkyl, C1-10-haloalkyl, C2-10-alkenyl, C2-10-haloalkenyl, C2-10-alkynyl, C2-10-haloalkynyl, C3- 10-cycloalkyl, C3-10-halocycloalkyl, C1-10-alkoxy, C1-10-haloalkoxy, C1-4-alkoxy-C1-10-alkyl, C1-4-alkoxy-C1-10-alkoxy, C1-10- alkylthio, C1-10-haloalkylthio, C2-10-alkenyloxy, C2-10-alkenylthio, C2-10-alkynyloxy, C2-10-alkynylthio, C3-10-cycloalkoxy, C3-10-cycloalkylthio, phenyl, phenyl-C1- 4-alkyl, phenoxy, phenylthio, phenyl-C1-4-alkoxy, and NR11 R12; each R8 is independently selected from halogen, CN, nitro, C1-4-alkyl, C1-4-haloalkyl, C1-4-alkoxy, C1-4-haloalkoxy and NR13R14; R9 is selected from hydrogen and C1-8-alkyl; R10 is selected from hydrogen, C1-8-alkyl, phenyl, and phenyl-C1-4-alkyl; or R9 and R10 together, form a linear bridge of C4- or C5-alkylene or a group -CH2CH2OCH2CH2- or -CH2CH2NR15CH2CH2-; R11 is selected from hydrogen and C1-8-alkyl; R12 is selected from hydrogen, C1-8-alkyl, phenyl, and phenyl-C1-4-alkyl; or R11 and R12 together, form a linear bridge of C4- or C5-alkylene or a group -CH2CH2OCH2CH2- or -CH2CH2NR15CH2CH2-; R13 independently of each event, is selected from hydrogen and C1-8-alkyl; R14 independently of each event, is selected from hydrogen, C1-8-alkyl, phenyl, and phenyl-C1-4-alkyl; or R13 and R14 together, form a linear bridge of C4- or C5-alkylene or a group -CH2CH2OCH2CH2- or -CH2CH2NR15CH2CH2-; R15 regardless of each event, is selected from hydrogen and C1-4-alkyl; Q is O or S; M is an equivalent of the metal cation or an ammonium cation of the formula (NRaRbRcRd) +, wherein Ra, Rb, Rc and Rd, independently of each other, are selected from hydrogen, C1-10-alkyl, phenyl and benzyl, in where the portion of phenyl in the last 2 radicals mentioned may carry 1, 2 or 3 substituents independently selected from halogen, CN, nitro, C1-4-alkyl, C1-4-haloalkyl, C1-4-alkoxy, C1-4- haloalkoxy and NR13R14; n is 0, 1, 2 or 3; and ---- is a single or double bond; and its acceptable salts in agriculture. Claim 15: Compounds characterized in that they have the formula (4) wherein R1, R2, R3, and Het are as defined in any one of claims 1 to 7; with the exception of the compounds, wherein R1, R2 and R3 are hydrogen, Het is 4-chloropyridin-3-yl and ---- is a single bond; R1 and R2 are methyl, R3 is hydrogen, Het is 4-chloropyridin-3-yl, 2-chlorothiazol-2-yl, 2-chlorothien-2-yl, 3,5-dichloropyridin-4-yl, 2-chlorofuran- 5-yl, 2-bromo-thien-5-yl, 3-bromo-thien-5-yl, 4-chloropyridin-2-yl or furan-2-yl and is a single bond; R1 is isopropyl, R2 and R3 are hydrogen, Het is 4-chloropyridin-3-yl or 3,5-dichloropyridin-4-yl and ---- is a single bond; R1 is ethyl, R2 and R3 are hydrogen, Het is 4-chloropyridin-2-yl, 4-chloropyridin-3-yl, 4-trifluoropyridin-2-yl, 4-trifluoropyridin-3-yl, 4-fluoropyridin-3- ilo or 3-chloropyridazin-6-yl and ---- is a single bond; R1 is methyl, R2 and R3 are hydrogen, Het is 4-chloropyridin-3-yl and ---- is a single bond; R1 is propyl, R2 and R3 are hydrogen, Het is 4-chloropyridin-3-yl and ---- is a single bond; R1 is isobutyl, R2 and R3 are hydrogen, Het is 4-chloropyridin-3-yl and ---- is a single bond; R1, R2 and R3 are hydrogen, Het is 4-tetrahydropyranyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 2-thienyl, 3-thienyl or 5-imidazolyl and ---- is a double bond ; R1 and R2 are methyl, R3 is hydrogen, Het is 2-furyl and ---- is a double bond. Claim 16: Compounds characterized in that they have the formula (5) wherein R1, R2, R3 and Het are as defined in any one of claims 1 to 7; except for the compounds, wherein R1, R2 and R3 are hydrogen, and Het is 4-chloropyridin-3-yl; R1 and R2 are methyl, R3 is hydrogen and Het is 4-chloropyridin-3-yl, 2-chlorothiazol-2-yl, 2-chlorothien-2-yl, 3,5-dichloropyridin-4-yl, 2-chlorofuran- 5-yl, 2-bromo-thien-5-yl, 3- bromo-thien-5-yl, 4-chloropyridin-2-yl or furan-2-yl; R1 is isopropyl, R2 and R3 are hydrogen and Het is 4-chloropyridin-3-yl or 3,5-dichloropyridin-4-yl; R1 is ethyl, R2 and R3 are hydrogen and Het is 4-chloropyridin-2-yl, 4-chloropyridin-3-yl, 4-trifluoropyridin-2-yl, 4-trifluoropyridin-3-yl, 4-fluoropyridin-3- yl or 3-chloropyridazin-6-yl; R1 is methyl, R2 and R3 are hydrogen and Het is 4-chloropyridin-3-yl; R1 is propyl, R2 and R3 are hydrogen and Het is 4-chloropyridin-3-yl; R1 is isobutyl, R2 and R3 are hydrogen and Het is 4-chloropyridin-3-yl. Claim 17: Compounds characterized in that they have the formula (6) wherein R1, R2, R3 and Het are as defined in any one of claims 1 to 7; With the exception of the compounds, wherein R1, R2 and R3 are hydrogen, Het is 3-pyridyl, 2-furyl or 3-thienyl and ---- is a double bond. Claim 18: Compounds characterized in that they have the formula (7) wherein R1, R2, R3 and Het are as defined in any of claims 1 to 7. Claim 19: Compounds characterized in that they have the formula (8) wherein R1, R2, R3 and Het are as defined in any of claims 1 to 7. Claim 20: Compounds characterized in that they have the formula (9) wherein R1, R2, R3 and Het are as defined in any of claims 1 to 7; and R14 is H or C (O) OR15, wherein R15 is selected from hydrogen, C1-10-alkyl, C1-10-haloalkyl, C3-10-cycloalkyl, C3-10-halocycloalkyl, phenyl, phenyl-C1-4 -alkyl, where the portion of phenyl in the last 2 radicals mentioned may carry 1, 2, 3, 4 or 5 R8 substituents, and a saturated, partially unsaturated or aromatic 5 or 6 membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members, wherein the heterocyclic ring may carry 1, 2 or 3 substituents R8, wherein R8 is as defined in claim 1. Claim 21: Compounds characterized in that they have the formula ( 10) wherein R1, R3 and Het are as defined in any of claims 1 to 7 and R14 is as defined in claim 18. Claim 22: Compounds characterized in that they have the formula (11) wherein R1, R2, R3 and Het are as defined in any of claims 1 to 7.

ARP100101400A 2009-04-24 2010-04-26 DERIVATIVES OF TRIAZOL AS FUNGICIDES IN AGRICULTURAL COMPOSITIONS AND THEIR USE AS ANTIVIRALS AND IN THE TREATMENT OF CANCER AND INTERMEDIARIES TO PRODUCE THEM AR076430A1 (en)

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