AR064563A1 - DERIVATIVES OF N-ALQUINILBENZAMIDA, A PROCEDURE FOR ITS PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS IT AND ITS USE IN A METHOD TO COMBAT FITOPATOGEN FUNGI. - Google Patents

DERIVATIVES OF N-ALQUINILBENZAMIDA, A PROCEDURE FOR ITS PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS IT AND ITS USE IN A METHOD TO COMBAT FITOPATOGEN FUNGI.

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Publication number
AR064563A1
AR064563A1 ARP070105932A ARP070105932A AR064563A1 AR 064563 A1 AR064563 A1 AR 064563A1 AR P070105932 A ARP070105932 A AR P070105932A AR P070105932 A ARP070105932 A AR P070105932A AR 064563 A1 AR064563 A1 AR 064563A1
Authority
AR
Argentina
Prior art keywords
alkyl
halogen atoms
halogen
sulfanyl
alkenyl
Prior art date
Application number
ARP070105932A
Other languages
Spanish (es)
Original Assignee
Bayer Cropscience Ag
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.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of AR064563A1 publication Critical patent/AR064563A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/64Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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: n es 1, 2, 3 o 4; 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, n es 1, 2, 3 o 4; X es un átomo de hidrogeno, un átomo de halogeno, un grupo nitro, ciano, sulfanilo, pentafluoro-gamma6-sulfanilo, formilo, formiloxi, formilamino, carboxi, un alquilo C1-8, halogenoalquilo C1-8 con 1 a 5 átomos de halogeno, un alcoxi C1-8-alquenilo C2-8, un alquil C1-8-sulfanilo, un halogenoalquil C1-8-sulfanilo de 1 a 5 átomos de halogeno, un halogenoalcoxi C1-8-carbonilo de 1 a 5 átomos de halogeno, un alquil C1-8-carboniloxi, un halogenoalquil C1-8-carboniloxi de 1 a 5 átomos de halogeno, un alquil C1-8-sulfenilo, un halogenoalquil C1-8-sulfenilo de 1 a 5 átomos de halogeno, un alquil C1-8-sulfinilo, un halogenoalquil C1-8-sulfinilo de 1 a 5 átomos de halogeno, un alquil C1- 8-sulfonilo, un halogenoalquil C1-8-sulfonilo de 1 a 5 átomos de halogeno o una alquil C1-8-sulfonamida; y Xa es un átomo de halogeno, un grupo nitro, ciano, sulfanilo, pentafluoro-gamma6-sulfanilo, formilo, formiloxi, formilamino, carboxi, un alquilo C1-8, un halogenoalquilo C1-8 con 1 a 5 átomos de halogeno, un alquenilo C2-8, un alquinilo C2-8, un alcoxi C1-8, un halogenoalcoxi C1-8 con 1 a 5 átomos de halogeno, un alcoxi C1-8- alquenilo C2-8, un alquil C1-8-sulfanilo, un halogenoalquil C1-8-sulfanilo con 1 a 5 átomos de halogeno, un alcoxi C1-8-carbonilo, un halogenoalcoxi C1-8-carbonilo con 1 a 5 átomos de halogeno, un alquil C1-8-carboniloxi, un halogenoalquil C1-8-carboniloxi con 1 a 5 átomos de halogeno, un alquil C1-8-sulfenilo, un halogenoalquil C1-8-sulfenilo con 1 a 5 átomos de halogeno, un alquil C1-8-sulfinilo; un halogenoalquil C1-8-sulfinilo con 1 a 5 átomos de halogeno, un alquil C1-8-sulfonilo, un halogenoalquil C1-8-sulfonilo con 1 a 5 átomos de halogeno o una alquil C1-8-sulfonamida; así como sus sales, N-oxidos, complejos metálicos, complejos metaloides e isomeros opticamente activos; con la condicion de que el compuesto de formula (1) es diferente de: ácido 2-(but-3-in-1- ilcarbamoil)benzoico; N-but-3-in-1-il-2-formamidobenzamida; y 2-amino-N-but-3-in-1-ilbenzamida. Reivindicacion 9: Un procedimiento para la preparacion de un compuesto de formula general (1) como se ha definido en la reivindicacion 1, que comprende hacer reaccionar un derivado de la alquiniletilamina 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: X, Xa y n son como se definen 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, 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 of treating plants by applying a compound of general formula (1) or a composition comprising it Claim 1: A compound of general formula (1), wherein: n is 1, 2, 3 or 4; R1 is 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- halogenocycloalkyl 6 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, n is 1, 2, 3 or 4; X is a hydrogen atom, a halogen atom, a nitro, cyano, sulfanyl, pentafluoro-gamma6-sulfanyl, formyl, formyloxy, formylamino, carboxy, a C1-8 alkyl, C1-8 halogenoalkyl group with 1 to 5 atoms of halogen, a C1-8 alkoxy-C2-8 alkenyl, a C1-8 alkyl sulfanyl, a halogeno C1-8 alkyl sulfanyl of 1 to 5 halogen atoms, a halogenoalkoxy C1-8-carbonyl of 1 to 5 halogen atoms , a C1-8 alkylcarbonyloxy, a halogeno C1-8 alkylcarbonyloxy of 1 to 5 halogen atoms, a C1-8 alkyl sulfenyl, a halogeno C1-8 alkyl sulfulfyl of 1 to 5 halogen atoms, a C1 alkyl -8-sulfinyl, a halogenC 1-8 alkyl sulfinyl of 1 to 5 halogen atoms, a C 1-8 alkyl sulfonyl, a halogen C 1-8 alkyl sulfonyl of 1 to 5 halogen atoms or a C 1-8 alkyl sulfonamide ; and Xa is a halogen atom, a nitro, cyano, sulfanyl, pentafluoro-gamma6-sulfanyl, formyl, formyloxy, formylamino, carboxy group, a C1-8 alkyl, a C1-8 halogenoalkyl with 1 to 5 halogen atoms, a C2-8 alkenyl, a C2-8 alkynyl, a C1-8 alkoxy, a C1-8 halogenoalkoxy with 1 to 5 halogen atoms, a C1-8 alkoxyC2-8 alkenyl, a C1-8 alkyl sulfanyl, a C 1-8 halogenoalkyl sulfanyl with 1 to 5 halogen atoms, a C 1-8 alkoxycarbonyl, a C 1-8 halogenoalkoxycarbonyl with 1 to 5 halogen atoms, a C 1-8 alkylcarbonyloxy, a C 1-8 alkyl halogen -carbonyloxy with 1 to 5 halogen atoms, a C1-8-sulfenyl alkyl, a halogen C1-8-alkylphenyl with 1 to 5 halogen atoms, a C1-8-sulfinyl alkyl; a halogeno C1-8 alkyl sulfinyl with 1 to 5 halogen atoms, a C1-8 alkyl sulfonyl, a halogeno C1-8 alkyl sulfonyl with 1 to 5 halogen atoms or a C1-8 alkyl sulfonamide; as well as its salts, N-oxides, metal complexes, metalloid complexes and optically active isomers; with the proviso that the compound of formula (1) is different from: 2- (but-3-in-1- ylcarbamoyl) benzoic acid; N-but-3-in-1-yl-2-formamidobenzamide; and 2-amino-N-but-3-in-1-ylbenzamide. Claim 9: A process for the preparation of a compound of general formula (1) as defined in claim 1, comprising reacting an alkynylethylamine derivative of general formula (2) or a salt thereof: wherein R1, R2, R3, R4, R5 and R6 are as defined in claim 1; with a carboxylic acid derivative of the general formula (3) wherein: X, Xa and n are 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, 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.

ARP070105932A 2007-01-03 2007-12-27 DERIVATIVES OF N-ALQUINILBENZAMIDA, A PROCEDURE FOR ITS PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS IT AND ITS USE IN A METHOD TO COMBAT FITOPATOGEN FUNGI. AR064563A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP07100059 2007-01-03

Publications (1)

Publication Number Publication Date
AR064563A1 true AR064563A1 (en) 2009-04-08

Family

ID=38171095

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070105932A AR064563A1 (en) 2007-01-03 2007-12-27 DERIVATIVES OF N-ALQUINILBENZAMIDA, A PROCEDURE FOR ITS PREPARATION, A FUNGITIVE COMPOSITION THAT UNDERSTANDS IT AND ITS USE IN A METHOD TO COMBAT FITOPATOGEN FUNGI.

Country Status (3)

Country Link
AR (1) AR064563A1 (en)
CL (1) CL2008000006A1 (en)
WO (1) WO2008081016A1 (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE787381A (en) * 1971-08-12 1973-02-09 Basf Ag AMID SUBSTITUTES FOR BENZOIC ACID
DE10354607A1 (en) * 2003-11-21 2005-06-16 Bayer Cropscience Ag Siylated carboxamides
GB0413605D0 (en) * 2004-06-17 2004-07-21 Addex Pharmaceuticals Sa Novel compounds

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Publication number Publication date
CL2008000006A1 (en) 2008-07-11
WO2008081016A1 (en) 2008-07-10
WO2008081016A8 (en) 2008-08-21

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