AR064564A1 - DERIVATIVES OF N-ALQUINYL CARBOXAMIDE, A PROCEDURE FOR THEIR PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS THEM AND A METHOD TO COMBAT PHYTO-PATHOGEN FUNGI THAT USES THEM. - Google Patents

DERIVATIVES OF N-ALQUINYL CARBOXAMIDE, A PROCEDURE FOR THEIR PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS THEM AND A METHOD TO COMBAT PHYTO-PATHOGEN FUNGI THAT USES THEM.

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Publication number
AR064564A1
AR064564A1 ARP070105933A AR064564A1 AR 064564 A1 AR064564 A1 AR 064564A1 AR P070105933 A ARP070105933 A AR P070105933A AR 064564 A1 AR064564 A1 AR 064564A1
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AR
Argentina
Prior art keywords
alkyl
sulfanyl
halogen atoms
alkenyl
halogen
Prior art date
Application number
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Spanish (es)
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Bayer Cropscience Ag
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Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of AR064564A1 publication Critical patent/AR064564A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un procedimiento para preparar este compuesto. Una composicion fungicida que comprende un compuesto de formula general (1). Un método para tratar plantas mediante la aplicacion de un compuesto de formula general (1) o una composicion que lo comprende. Reivindicacion 1: Un compuesto de formula general (1), en la que, R1 es un átomo de hidrogeno, un átomo de halogeno, un alquilo C1-6, un alquenilo C2-6, un alquinilo C2-6, un tri(alquilo C1-8)sililo, un cicloalquilo C3-6, un halogenocicloalquilo C3-6 que tiene 1 a 5 átomos de halogeno; R2 y R3 se seleccionan independientemente uno de otro para que sean un átomo de hidrogeno, un átomo de halogeno, un alquilo C1-6 , un alquenilo C2-6, un alquinilo C2-6, un tri(alquilo C1- 8)sililo, un cicloalquilo C3-6, un halogenocicloalquilo C3-6 que tiene 1 a 5 átomos de halogeno; R4 y R5 se seleccionan independientemente uno de otro para que sean un átomo de hidrogeno, un átomo de halogeno, un alquilo C1-6, un alquenilo C2-6, un alquinilo C2-6, un tri(alquilo C1-8)sililo, un cicloalquilo C3-6 un halogenocicloalquilo C3-6 que tiene 1 a 5 átomos de halogeno; o R2 o R3 pueden formar junto con R4 o R5 un cicloalquilo C3-7; R6 es un átomo de hidrogeno, un alquilo C1-6, o un cicloalquilo C3-7, y Het representa un heterociclo no condensado de 5, 6 o 7 elementos, opcionalmente sustituido con uno, dos o tres heteroátomos que pueden ser iguales o diferentes, estando Het unido por un átomo de C; estando sustituido Het en la porcion orto por un sustituyente seleccionado para que sea un átomo de halogeno, un grupo nitro, ciano, sulfanilo, pentafluoro-gamma6-sulfanilo, alquilo C1-8- halogenoalquilo C1-8 que tiene 1 a 5 átomos de halogeno, alquenilo C2-8, alquinilo C2-8, alcoxi C1-8, halogenoalcoxi C1-8 que tiene 1 a 5 átomos de halogeno, alcoxi C1-8-alquenilo C2-8, un alquil C1-8-sulfanilo, o un halogenoalquil C1-8-sulfanilo que tiene 1 a 5 átomos de halogeno, y opcionalmente sustituidos en cualquier otra posicion por uno o más sustituyentes seleccionados independientemente uno de otro de un átomo de halogeno, un grupo nitro, ciano, sulfanilo, pentafluoro-gamma6-sulfanilo, formilo, formiloxi, formilamino, carboxi, alquilo C1-8, halogenoalquilo C1-8 que tiene 1 a 5 átomos de halogeno, alquenilo C2-8, alquinilo C2-8, alcoxi C1-8, halogenoalcoxi C1-8 que tiene 1 a 5 átomos de halogeno, alcoxi C1-8alquenilo C2-8, alquil C1-8-sulfanilo o un halogenoalquil C1-8-sulfanilo con 1 a 5 átomos de halogeno; así como sus sales, N-oxidos, complejos metálicos, complejos metaloides e isomeros opticamente activos. Reivindicacion 10: Un procedimiento para la preparacion de un compuesto de formula general (1) como se define en la reivindicacion 1, que comprende hacer reaccionar un derivado de la N-alquinilcarboxamida de formula general (2) o una de sus sales: en la que R1, R2, R3, R4, R5 y R6 son como se definio en la reivindicacion 1; con un derivado de ácido carboxílico de formula general (3), en la que: Het es como se definio en la reivindicacion 1; y - L1 es un grupo saliente seleccionado para que sea un átomo de halogeno, un grupo hidroxilo, -ORa, -OCORa, siendo Ra un alquilo C1-6, un haloalquilo C1-6, un bencilo, 4-metoxibencilo, pentafluorofenilo o un grupo de formula (4) en presencia de un catalizador y, si L1 es un grupo hidroxilo, en presencia de un agente de condensacion.A procedure to prepare this compound. A fungicidal composition comprising a compound of general formula (1). A method for treating plants by applying a compound of general formula (1) or a composition comprising it. Claim 1: A compound of general formula (1), wherein, R1 is a hydrogen atom, a halogen atom, a C1-6 alkyl, a C2-6 alkenyl, a C2-6 alkynyl, a tri (alkyl C1-8) silyl, a C3-6 cycloalkyl, a C3-6 halogenocycloalkyl having 1 to 5 halogen atoms; R2 and R3 are independently selected from each other to be a hydrogen atom, a halogen atom, a C1-6 alkyl, a C2-6 alkenyl, a C2-6 alkynyl, a tri (C1-8 alkyl) silyl, a C3-6 cycloalkyl, a C3-6 halocyclocycloalkyl having 1 to 5 halogen atoms; R4 and R5 are independently selected from each other to be a hydrogen atom, a halogen atom, a C1-6 alkyl, a C2-6 alkenyl, a C2-6 alkynyl, a tri (C1-8 alkyl) silyl, a C3-6 cycloalkyl a C3-6 halocyclocycloalkyl having 1 to 5 halogen atoms; or R2 or R3 may together with R4 or R5 form a C3-7 cycloalkyl; R6 is a hydrogen atom, a C1-6 alkyl, or a C3-7 cycloalkyl, and Het represents an uncondensed heterocycle of 5, 6 or 7 elements, optionally substituted with one, two or three heteroatoms that may be the same or different. , Het being bound by a C atom; Het being substituted in the ortho portion by a substituent selected to be a halogen atom, a nitro, cyano, sulfanyl, pentafluoro-gamma6-sulfanyl, C1-8 alkyl-C1-8 halogenoalkyl group having 1 to 5 halogen atoms , C2-8 alkenyl, C2-8 alkynyl, C1-8 alkoxy, C1-8 halogenoalkoxy having 1 to 5 halogen atoms, C1-8 alkoxy-C2-8 alkenyl, a C1-8 alkyl sulfanyl, or a halogenoalkyl C1-8-sulfanyl having 1 to 5 halogen atoms, and optionally substituted in any other position by one or more substituents independently selected from one another from a halogen atom, a nitro, cyano, sulfanyl, pentafluoro-gamma6-sulfanyl group , formyl, formyloxy, formylamino, carboxy, C1-8 alkyl, C1-8 halogenoalkyl having 1 to 5 halogen atoms, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkoxy, C1-8 halogenoalkoxy having 1 to 5 halogen atoms, C 1-8 alkoxy C 2-8 alkenyl, C 1-8 alkyl sulfanyl or a C 1-8 halogen alkyl sulfanyl with 1 at 5 halogen atoms; as well as its salts, N-oxides, metal complexes, metalloid complexes and optically active isomers. Claim 10: A process for the preparation of a compound of general formula (1) as defined in claim 1, which comprises reacting a N-alkynylcarboxamide derivative of general formula (2) or a salt thereof: in the that R1, R2, R3, R4, R5 and R6 are as defined in claim 1; with a carboxylic acid derivative of the general formula (3), wherein: Het is as defined in claim 1; and - L1 is a leaving group selected to be a halogen atom, a hydroxyl group, -ORa, -OCORa, where Ra is a C1-6 alkyl, a C1-6 haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl or a group of formula (4) in the presence of a catalyst and, if L1 is a hydroxyl group, in the presence of a condensing agent.

ARP070105933 2007-01-03 2007-12-27 DERIVATIVES OF N-ALQUINYL CARBOXAMIDE, A PROCEDURE FOR THEIR PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS THEM AND A METHOD TO COMBAT PHYTO-PATHOGEN FUNGI THAT USES THEM. AR064564A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP07100063 2007-01-03

Publications (1)

Publication Number Publication Date
AR064564A1 true AR064564A1 (en) 2009-04-08

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ARP070105933 AR064564A1 (en) 2007-01-03 2007-12-27 DERIVATIVES OF N-ALQUINYL CARBOXAMIDE, A PROCEDURE FOR THEIR PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS THEM AND A METHOD TO COMBAT PHYTO-PATHOGEN FUNGI THAT USES THEM.

Country Status (3)

Country Link
AR (1) AR064564A1 (en)
CL (1) CL2008000005A1 (en)
WO (1) WO2008081017A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2532971T3 (en) 2010-06-03 2015-04-06 Bayer Intellectual Property Gmbh N - [(het) arylalkyl)] pyrazole (thio) carboxamides and their hetero substituted analogs
US8653003B2 (en) 2011-01-05 2014-02-18 Syngenta Participations Ag Pyrazol-4-yl carboxamide derivatives as microbiocides
WO2020244970A1 (en) * 2019-06-06 2020-12-10 Basf Se New carbocyclic pyridine carboxamides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4064135A (en) * 1976-07-19 1977-12-20 Syntex (U.S.A.) Inc. Certain thiazole-5-carboxamide compounds
DE4029654A1 (en) * 1990-09-19 1992-04-02 Hoechst Ag 2-PHENYL-PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF, AGENTS CONTAINING IT AND THEIR USE AS FUNGICIDES
DE10136065A1 (en) * 2001-07-25 2003-02-13 Bayer Cropscience Ag pyrazolylcarboxanilides
WO2004037787A1 (en) * 2002-10-18 2004-05-06 Basf Aktiengesellschaft 1-phenylpyrrolidine-2-one-3-carboxamides
DE102004059725A1 (en) * 2004-12-11 2006-06-22 Bayer Cropscience Ag 2-alkyl-cycloalk (en) yl-carboxamide
PT1885712E (en) * 2005-05-18 2011-04-29 Bayer Cropscience Ag New 2-pyridinylcycloalkylcarboxamide derivatives as fungicides.

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WO2008081017A1 (en) 2008-07-10

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