AR080262A1 - TRIAZOL COMPOUNDS, ITS USE, AS WELL AS PRODUCTS THAT CONTAIN USEFUL AS ANTIMICOTICS - Google Patents

TRIAZOL COMPOUNDS, ITS USE, AS WELL AS PRODUCTS THAT CONTAIN USEFUL AS ANTIMICOTICS

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Publication number
AR080262A1
AR080262A1 ARP090103455A ARP090103455A AR080262A1 AR 080262 A1 AR080262 A1 AR 080262A1 AR P090103455 A ARP090103455 A AR P090103455A AR P090103455 A ARP090103455 A AR P090103455A AR 080262 A1 AR080262 A1 AR 080262A1
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AR
Argentina
Prior art keywords
alkyl
alkynyl
alkenyl
oxy
phenyl
Prior art date
Application number
ARP090103455A
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Spanish (es)
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Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
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Publication of AR080262A1 publication Critical patent/AR080262A1/en

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Classifications

    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicacion 1: Compuestos caracterizados porque tienen la formula (1): en donde las variables presentan los siguientes significados: p es 5 o 6; R1 es alquilo C1-10, haloalquilo C1-10, alquenilo C2-10, halogenalquenilo C2-10, alquinilo C2-10, halogenalquinilo C3-10, cicloalquilo C3-8, halogencicloalquilo C3-8, cicloalquenilo C3-10, halogencicloalquenilo C3-10, en donde los grupos previamente mencionados no están sustituidos o pueden contener uno, dos, tres, cuatro o cinco sustituyentes seleccionados, de modo independiente, de halogeno, hidroxi, alquilo C1-8, halogenalquilo C1-8, alquenilo C2-8, halogenalquenilo C2-8, alquinilo C2-8, halogenalquinilo C3-8 y fenilo, en donde el fenilo no está, a su vez, sustituido o está sustituido con uno, dos, tres, cuatro o cinco sustituyentes L seleccionados de modo independiente; o arilo de 6 a 10 miembros, que no está sustituido o está sustituido con uno, dos, tres, cuatro o cinco sustituyentes L seleccionados de modo independiente, en donde L es: L es halogeno, ciano, nitro, hidroxi, cianato (OCN), alquilo C1-8, halogenalquilo C1-8, alquenilo C2-8, halogenalquenilo C2-8, alquinilo C2-8, halogenalquinilo C3-8, alcadienilo C4-10, halogenalcadienilo C4-10, alcoxi C1-8, halogenalcoxi C1-8, alquil C1-8-carboniloxi, alquil C1-8-sulfoniloxi, alquenil C2-8-oxi, halogenalquenil C2-8-oxi, alquinil C2-8-oxi, halogenalquinil C3-8-oxi, cicloalquilo C3-8, halogencicloalquilo C3-8, cicloalquenilo C3-8, halogencicloalquenilo C3-8, cicloalcoxi C3-8, cicloalquenil C3-6-oxi, hidroxiimino-alquilo C1-8, alquileno C1-6, oxi-alquileno C2-4, oxi-alquilen C1-3-oxi, alcoximino C1-8-alquilo C1-8, alquenil C2-8-oximino-alquilo C1-8, alquinil C2-8-oximino-alquilo C1-8, S(=O)nA1, C(=O)A2, C(=S)A2, NA3A4, fenoxi, fenilo, heteroariloxi, heterocicliloxi, heteroarilo, heterociclilo, en donde en los grupos previamente mencionados el heteroarilo es un heterociclo aromático de cinco, seis o siete miembros y el heterociclilo es un heterociclo saturado o parcialmente insaturado de cinco, seis o siete miembros, que contienen, en cada caso, uno, dos, tres o cuatro heteroátomos del grupo O, N y S; en donde n, A1, A2, A3, A4 son: n es 0, 1 o 2; A1 es hidrogeno, hidroxi, alquilo C1-8, halogenalquilo C1-8, amino, alquil C1-8-amino, di-alquil C1-8-amino, fenilo, fenilamino o fenil-alquil C1-8-amino; A2 es uno de los grupos mencionados en A1 o es alquenilo C2-8, halogenalquenilo C2-8, alquinilo C2-8, halogenalquinilo C3-8, alcoxi C1-8, halogenalcoxi C1-8, alquenil C2-8-oxi, halogenalquenil C2-8-oxi, alquinil C2-8-oxi, halogenalquinil C3-8-oxi, cicloalquilo C3-8, halogencicloalquilo C3-8, cicloalcoxi C3-8 o halogencicloalcoxi C3-8; A3, A4 son, de modo independiente entre sí, hidrogeno, alquilo C1-8, halogenalquilo C1-8, alquenilo C2-8, halogenalquenilo C2-8, alquinilo C2-8, halogenalquinilo C3-8, cicloalquilo C3-8, halogencicloalquilo C3-8, cicloalquenilo C3-8 o halogencicloalquenilo C3-8, fenilo o heteroarilo de 5 o 6 miembros con uno, dos, tres o cuatro heteroátomos del grupo O, N y S en el heterociclo; los grupos alifáticos y/o alicíclicos y/o aromáticos de las definiciones de los radicales de L pueden llevar, a su vez, uno, dos, tres o cuatro grupos RL iguales o diferentes: RL es halogeno, hidroxi, ciano, nitro, alquilo C1-8, halogenalquilo C1-8, alcoxi C1-8, halogenalcoxi C1-8, cicloalquilo C3-8, halogencicloalquilo C3-8, cicloalquenilo C3-8, cicloalcoxi C3-8, halogencicloalcoxi C3-8, alquileno C1-6, oxi-alquileno C2-4, oxi-alquilen C1-3-oxi, alquil C1-8-carbonilo, alquil C1-8-carboniloxi, alcoxi C1-8-carbonilo, amino, alquil C1-8-amino, di-alquil C1-8-amino; R2 es hidrogeno, alquilo C1-10, halogenalquilo C1-10, alquenilo C2-10, halogenalquenilo C2-10, alquinilo C2-10, halogenalquinilo C3-10, alcadienilo C4-10, halogenalcadienilo C4-10, cicloalquilo C3-10, halogencicloalquilo C3-10, cicloalquenilo C3-10, halogencicloalquenilo C3-10; R3 es hidrogeno, alquilo C1-10, halogenalquilo C1-10, alquenilo C2-10, halogenalquenilo C2-10, alquinilo C2-10, halogenalquinilo C3-10, alcadienilo C4-10, halogenalcadienilo C4-10, cicloalquilo C3-10, halogencicloalquilo C3-10, cicloalquenilo C3-10, halogencicloalquenilo C3-10, carboxilo, formilo, Si(A5A6A7), C(O)Rpi, C(O)ORpi, C(S)ORpi, C(O)SRpi, C(S)SRpi, C(NRA)SRpi, C(S)Rpi, C(NRpi)N-NA3A4, C(NRpi)RA, C(NRpi)ORA, C(O)NA3A4, C(S)NA3A4 o S(=O)nA1; en donde Rpi es alquilo C1-8, alquenilo C3-8, alquinilo C3-8, cicloalquilo C3-6, cicloalquenilo C3-6 o fenilo; RA es alquilo C1-8, alquenilo C3-8, alquinilo C3-8, cicloalquilo C3-6, cicloalquenilo C3-6 o fenilo; A5, A6, A7 son, de modo independiente entre sí, alquilo C1-10, alquenilo C3-8, alquinilo C3-8, cicloalquilo C3-6, cicloalquenilo C3-6 o fenilo; en donde Rpi, RA, A5, A6 y A7, siempre que no se indique otra cosa, de modo independiente entre si, no están sustituidos o están sustituidos con uno, dos, tres, cuatro o cinco L, tal como se definio con anterioridad; R4 es hidrogeno, alquilo C1-10, halogenalquilo C1-10, alquenilo C2-10, halogenalquenilo C2-10, alquinilo C2-10, halogenalquinilo C3-10, alcadienilo C4-10, halogenalcadienilo C4-10, cicloalquilo C3-10, halogencicloalquilo C3-10, cicloalquenilo C3-10, halogencicloalquenilo C3-10; R2, R3 y R4 siempre que no se indique otra cosa, de modo independiente entre sí, no están sustituidos o están sustituidos con uno, dos, tres, cuatro o cinco L, tal como se definio con anterioridad; con la condicion de que R1 no sea fenilo no sustituido cuando p = 5 y R2, R3 y R4 son hidrogeno, y R1 no sea fenilo no sustituido cuando p = 5 y R2 = hidrogeno, R3 = metilo o 3-propen-1-ilo y R4 = son hidrogeno; y sus sales de tolerancia en agricultura.Claim 1: Compounds characterized in that they have the formula (1): wherein the variables have the following meanings: p is 5 or 6; R1 is C1-10 alkyl, C1-10 haloalkyl, C2-10 alkenyl, C2-10 halogenalkenyl, C2-10 alkynyl, C3-10 halogenalkynyl, C3-8 cycloalkyl, C3-8 halogencycloalkyl, C3-10 haloalkyl, C3- halogencycloalkenyl 10, wherein the aforementioned groups are not substituted or may contain one, two, three, four or five substituents independently selected from halogen, hydroxy, C1-8 alkyl, halogenalkyl C1-8, C2-8 alkenyl, C2-8 halogenalkenyl, C2-8 alkynyl, C3-8 halogenalkynyl and phenyl, wherein the phenyl is not, in turn, substituted or substituted with one, two, three, four or five independently selected L substituents; or 6 to 10 membered aryl, which is unsubstituted or substituted with one, two, three, four or five independently selected L substituents, wherein L is: L is halogen, cyano, nitro, hydroxy, cyanate (OCN ), C1-8 alkyl, halogenalkyl C1-8, alkenyl C2-8, halogenalkenyl C2-8, alkynyl C2-8, halogenalkynyl C3-8, alkydienyl C4-10, halogenalcadienyl C4-10, alkoxy C1-8, halogenalkoxy C1- 8, C1-8 alkylcarbonyloxy, C1-8 alkyl sulfonyloxy, C2-8-oxy alkenyl, C2-8-oxy halogenalkenyl, C2-8-oxy alkynyl, C3-8-halogenalkynyl, halogencycloalkyl C3-8, C3-8 cycloalkenyl, C3-8 halogencycloalkenyl, C3-8 cycloalkoxy, C3-6-oxycycloalkenyl, C1-8 hydroxyimino-alkyl, C1-6 alkylene, C2-4 oxy-alkylene, C1-oxy-alkylene 3-oxy, C 1-8 alkoxy-C 1-8 alkyl, C 2-8 alkenyl-C 1-8 alkyl, C 2-8 alkynyl-C 1-8 alkynyl, S (= O) nA1, C (= O) A2, C (= S) A2, NA3A4, phenoxy, phenyl, heteroaryloxy, heterocyclyloxy, heteroaryl, heterocyclyl, where e in the previously mentioned groups the heteroaryl is a five, six or seven membered aromatic heterocycle and the heterocyclyl is a saturated, or partially unsaturated, five, six or seven membered heterocycle, containing, in each case, one, two, three or four heteroatoms of the group O, N and S; where n, A1, A2, A3, A4 are: n is 0, 1 or 2; A1 is hydrogen, hydroxy, C 1-8 alkyl, C 1-8 halogenalkyl, amino, C 1-8 alkyl, di C 1-8 alkyl, amino, phenyl, phenylamino or phenyl C 1-8 alkyl; A2 is one of the groups mentioned in A1 or is C2-8 alkenyl, C2-8 halogenalkenyl, C2-8 alkynyl, C3-8 halogenalkynyl, C1-8 alkoxy, C1-8 halogenalkoxy, C2-8-oxy alkenyl, C2 halogenalkenyl -8-oxy, C2-8-oxy alkynyl, C3-8-oxy halogenalkynyl, C3-8 cycloalkyl, C3-8 halogencycloalkyl, C3-8 cycloalkoxy or C3-8 halogencycloalkoxy; A3, A4 are, independently of one another, hydrogen, C1-8 alkyl, C1-8 halogenalkyl, C2-8 alkenyl, C2-8 halogenalkenyl, C2-8 alkynyl, C3-8 halogenalkynyl, C3-8 cycloalkyl, C3 halogencycloalkyl -8, C3-8 cycloalkenyl or C3-8 halogencycloalkenyl, 5 or 6 membered phenyl or heteroaryl with one, two, three or four heteroatoms of the group O, N and S in the heterocycle; the aliphatic and / or alicyclic and / or aromatic groups of the definitions of the radicals of L may, in turn, carry one, two, three or four same or different RL groups: RL is halogen, hydroxy, cyano, nitro, alkyl C1-8, halogenalkyl C1-8, alkoxy C1-8, halogenalkoxy C1-8, cycloalkyl C3-8, halogencycloalkyl C3-8, cycloalkenyl C3-8, cycloalkoxy C3-8, halogencycloalkoxy C3-8, alkylene C1-6, oxy -C2-4 alkylene, oxy-C 1-3 alkylene-oxy, C 1-8 alkylcarbonyl, C 1-8 alkylcarbonyloxy, C 1-8 alkoxycarbonyl, amino, C 1-8 alkyl amino, C 1-8 alkyl 8-amino; R2 is hydrogen, C1-10 alkyl, C1-10 halogenalkyl, C2-10 alkenyl, C2-10 halogenalkenyl, C2-10 alkynyl, C3-10 halogenalkynyl, C4-10 alkydienyl, C4-10 halogenalcadienyl, C3-10 cycloalkyl, halogencycloalkyl C3-10, C3-10 cycloalkenyl, C3-10 halogencycloalkenyl; R3 is hydrogen, C1-10 alkyl, C1-10 halogenalkyl, C2-10 alkenyl, C2-10 halogenalkenyl, C2-10 alkynyl, C3-10 halogenalkynyl, C4-10 alkydienyl, C4-10 halogenalcadienyl, C3-10 cycloalkyl, halogencycloalkyl C3-10, C3-10 cycloalkenyl, C3-10 halogencycloalkenyl, carboxyl, formyl, Si (A5A6A7), C (O) Rpi, C (O) ORpi, C (S) ORpi, C (O) SRpi, C (S ) SRpi, C (NRA) SRpi, C (S) Rpi, C (NRpi) N-NA3A4, C (NRpi) RA, C (NRpi) ORA, C (O) NA3A4, C (S) NA3A4 or S (= O) nA1; wherein Rpi is C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkenyl or phenyl; RA is C 1-8 alkyl, C 3-8 alkenyl, C 3-8 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkenyl or phenyl; A5, A6, A7 are, independently of each other, C1-10 alkyl, C3-8 alkenyl, C3-8 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkenyl or phenyl; wherein Rpi, RA, A5, A6 and A7, provided that nothing else is indicated, independently of each other, are not substituted or substituted with one, two, three, four or five L, as defined above. ; R4 is hydrogen, C1-10 alkyl, C1-10 halogenalkyl, C2-10 alkenyl, C2-10 halogenalkenyl, C2-10 alkynyl, C3-10 halogenalkynyl, C4-10 alkydienyl, C4-10 halogenalcadienyl, C3-10 cycloalkyl, halogencycloalkyl C3-10, C3-10 cycloalkenyl, C3-10 halogencycloalkenyl; R2, R3 and R4 as long as it is not indicated otherwise, independently of each other, they are not substituted or substituted with one, two, three, four or five L, as defined above; with the proviso that R1 is not unsubstituted phenyl when p = 5 and R2, R3 and R4 are hydrogen, and R1 is not unsubstituted phenyl when p = 5 and R2 = hydrogen, R3 = methyl or 3-propen-1- ilo and R4 = are hydrogen; and its tolerance salts in agriculture.

ARP090103455A 2008-09-09 2009-09-09 TRIAZOL COMPOUNDS, ITS USE, AS WELL AS PRODUCTS THAT CONTAIN USEFUL AS ANTIMICOTICS AR080262A1 (en)

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EP08163966 2008-09-09

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AR080262A1 true AR080262A1 (en) 2012-03-28

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AR (1) AR080262A1 (en)
UY (1) UY32103A (en)
WO (1) WO2010029003A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013514299A (en) 2009-12-18 2013-04-25 ビーエーエスエフ ソシエタス・ヨーロピア Method for producing triazolinethione derivative and intermediate thereof
JP2013056832A (en) * 2010-01-12 2013-03-28 Univ Of Tokyo Strigolactone biosynthesis inhibitor
WO2011110583A2 (en) 2010-03-10 2011-09-15 Basf Se Fungicidal mixtures comprising triazole derivatives
US8729272B2 (en) 2010-03-16 2014-05-20 Basf Se Process using grignard reagents
CN103228650A (en) 2010-09-30 2013-07-31 巴斯夫欧洲公司 A process for the synthesis of thio-riazolo-group containing compounds
WO2012130823A1 (en) 2011-03-30 2012-10-04 Basf Se Suspension concentrates

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3019049A1 (en) * 1980-05-19 1981-12-03 Basf Ag, 6700 Ludwigshafen NEW AZOLES
DE3151440A1 (en) * 1981-12-24 1983-07-07 Bayer Ag, 5090 Leverkusen ANTIMYCOTIC AGENTS
DE3416444A1 (en) * 1984-05-04 1985-11-07 Basf Ag, 6700 Ludwigshafen METHOD FOR DIASTEREOSELECTIVE REDUCTION OF (ALPHA) -TRIAZOLYLKETONES TO SS-TRIAZOLYLCARBINOLS
DE3437919A1 (en) * 1984-10-17 1986-04-17 Basf Ag, 6700 Ludwigshafen BENZYLOXYALKYLAZOLES AND FUNGICIDES CONTAINING THEM
DE3601430A1 (en) * 1986-01-20 1987-07-23 Basf Ag HALOGENED AZOL COMPOUNDS AND FUNGICIDES CONTAINING THEM
DE3724645A1 (en) * 1987-07-25 1989-02-02 Basf Ag HYDROXYETHYL AZOL DERIVATIVES AND THEIR USE AS FUNGICIDES

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