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AR055103A1 - COMPOUNDS OF 7-AMINO-6-HETEROARIL-1,2,4-TRIAZOLO [1,5-A] PYRIMIDINE AND ITS EMPLOYMENT TO COMBAT DANGINE FUNGES - Google Patents

COMPOUNDS OF 7-AMINO-6-HETEROARIL-1,2,4-TRIAZOLO [1,5-A] PYRIMIDINE AND ITS EMPLOYMENT TO COMBAT DANGINE FUNGES

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Publication number
AR055103A1
AR055103A1 ARP060103299A ARP060103299A AR055103A1 AR 055103 A1 AR055103 A1 AR 055103A1 AR P060103299 A ARP060103299 A AR P060103299A AR P060103299 A ARP060103299 A AR P060103299A AR 055103 A1 AR055103 A1 AR 055103A1
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Argentina
Prior art keywords
alkyl
amino
halogenoalkyl
alkoxy
alkynyl
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ARP060103299A
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Spanish (es)
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Basf Ag
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Publication of AR055103A1 publication Critical patent/AR055103A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Los compuestos de la presente son utiles en agricultura. Reivindicacion 1: 7-Amino-6-heteroaril-1,2,4-triazolo[1,5-a]pirimidinas caracterizado porque tiene la formula (1) en la cual los sustituyentes Het, R1, R2, X e Y tienen los siguientes significados: Het representa un grupo heteroarilo de cinco eslabones que contiene dos átomos de nitrogeno como eslabones del anillo, que está seleccionado de 1,2,3-tiadiazolilo, 1,2,4-tiadiazolilo, 1,3,4-tiadiazolilo, 1,2,5-tiadiazolilo, 1,2,4- oxadiazolilo, 1,3,4-oxadiazolilo y 1,2,5-oxadiazolilo, pudiendo estar Het sin sustituir, o bien estar sustituido con uno o dos L; L halogeno, ciano, nitro, hidroxi, cianato (OCN), alquiloC1-8, halogenoalquilo C1-6, alquenilo C2-8, halogenoalquenilo C2-8, alquinilo C2-8, halogenoalquinilo C2-8, alcadienilo C2-8, halogenalcadienilo C4-10, alcoxi C1-8, halogenoalcoxi C1-8, alqueniloxi C2-8, halogenoalqueniloxi C2-8, alquiniIoxi C2-8, halogenoalquiniloxi C2-8, cicloalquilo C3-8, halogenociclo- alquilo C3-8, cicloalquenilo C3-8, halogenocicloalquenilo C3-8, cicloalcoxi C3-8, alcoximino C1-8-alquilo C1-8, alqueniloximino C2-8-alquilo C1-8, alquiniloximino C2-8-alquilo C1-8, alquil C1-8)-tio, S(=O)nA1, C(=O)A2, C(=S) A2, NR5R6, NR5-(C=O)-R6; en donde n representa 0, 1 o 2; A1 significa hidrogeno, hidroxi, alquilo C1-8, halogenoalquilo C1-8, amino, alquil C1-8-amino o dialquil C1-8-amino, A2 significa uno de los grupos mencionados en A1, o bien alquenilo C 2-8, halogenoalquenilo C2-8, alquinilo C2-8, halogenoalquinilo C2-8, alcoxi C1-8, halogenoalcoxi C1-8, alqueniloxi C2-8, halogenoalqueniloxi C2-8, alquiniloxi C2-8, halogenoaIquiniloxi C2-8, cicloalcoxi C3-8, halogenocicIoaIcoxi C3-8; R5, R6, de manera independiente entre si, significan hidrogeno, alquilo C1-8, halogenoalquilo C1-8, alquenilo C2-8, halogenoalquenilo C2-8, alquinilo C2-8, halogenoalquiniIo C2-8, cicloalquilo C3-8, halogenocicIoalquilo C3-8, cicloalquenilo C3-8 o halogenocicloalquenilo C3-8 en donde los grupos alifáticos de las definiciones de radicales L pueden portar, por su parte, de uno a cuatro grupos RL, Iguales o diferentes: RL halogeno, ciano, alcoxi C1-8, alqueniloxi C2-8, alquiniloxi C2-8, cicloalquilo C3-8, cicloalquenilo C3-8, cicloalquiloxi C3-8, cicloalqueniloxi C3-8, alcoxi C1-8-imino-alquilo C1-8, alqueniloxi C2-8-imino-alquilo C1-8, alquiniloxi C2-8-imino-alquilo C1-8, S(=O)nA1, C(=O)A2, C(=S)A2, NR5R6, NR5-(C=O)-R6; R1, R2, de manera independiente entre si, hidrogeno, alquilo C1-8, halogenoalquilo C1-8, alquenilo C2-8, halogenoalquenilo C2-8, alquinilo C2-8, halogenoalquiniIo C2-8, alcadienilo C4-10, halogenalcadienilo C4-10, alcoxi C1-8, halogenoalcoxi C1-8, alqueniloxi C2-8, halogenoalqueniloxi C2-8, alquiniIoxi C2-8, halogenoalquiniloxi C2-8, cicloalquilo C3-8, halogenocicloalquilo C3-8, cicloalquenilo C3-8, halogenocicloalquenilo C3-8, cicloalcoxi C3-8, halogenocicloalcoxi C3-8, bicicloalquilo C5-10, amino, alquil C1-8-amino, di-alquil C1-8- amino, fenilo, naftilo o un heterociclo de cinco o seis eslabones, saturado, parcialmente insaturado, o aromático, que contiene uno, dos, tres o cuatro heteroátomos del grupo de O, N y S; y R1 R2 pueden formar también, junto con el átomo de nitrogeno al cual están unidos, un heterociclo de cinco o seis eslabones, saturado, parcialmente insaturado, o aromático, que puede contener uno, dos o tres heteroátomos adicionales del grupo de O, N y S como eslabones del anillo, en donde R1 y/o R2, o un heterociclo formado a partir de R1 y R2, pueden portar uno, dos, tres o cuatro grupos Ra, iguales o diferentes, y/o dos sustituyentes unidos a átomos del anillo vecinos pueden representar alquileno C1-6, oxialquileno C2-4 u oxialquilen C1-3- oxi; en donde Ra significa: halogeno, ciano, nitro, hidroxi, carboxilo, amino, alquilo C1-8, halogenoalquilo C1-8, alquenilo C2-8, halogenoalquenilo C2-8, alquinilo C2-8, halogenoalquiniIo C2-8, alcadienilo C4-10, alcoxi C1-8, halogenoalcoxi C1-8, alqueniloxi C2-8, halogenoalqueniloxi C2-8, alquiniIoxi C2-8, halogenoalquiniloxi C2-8, cicloalquilo C3-8, halogenocicloalquilo C3-8, cicloalquenilo C3-8, cicloalcoxi C3-8, halogenocicloalcoxi C3-8, cicloalqueniloxi C3-8, bicicloalquilo C5-10, alquil C1-8- carbonilo, alcoxi C1-8-carbonilo, alquil C1-8-carboniloxi, alquil C1-8-amino, di-alquil C1-8-amino, alquil C1-8-aminocarbonilo, di-alquil C1-8- aminocarbonilo, alquil C1-8-aminotiocarbonilo, di-alquil C1-8-aminotiocarbonilo, oxi- alquilenoxi C1-6, alquil C1-8-tio, alquil C1-8-sulfinilo, alquil C1-8-sulfonilo, alquil C1-8-sulfoxilo, fenilo, naftilo, heterociclo de cinco a diez eslabones saturado, parcialmente insaturado o aromático, que contiene uno, dos, tres o cuatro heteroátomos del grupo de O, N y S; pudiendo portar los grupos alifáticos, alicíclicos o aromáticos de Ra, por su parte, uno, dos o tres grupos Rb, iguales o diferentes: Rb halogeno, ciano, nitro, hidroxi, carboxilo, mercapto, amino, formilo, aminocarbonilo, aminotiocarbonilo, alquilo C1-8, halogenoalquilo C1-8, alquenilo C2-8, halogenoalquenilo C2-8, alcadienilo C4-10, alquinilo C2-8, halogenoalquiniIo C2-8, alcoxi C1-8, halogenoalcoxi C1-8, alqueniloxi C2-8, alquiniIoxi C2-8, cicloalquilo C3-8, cicloalquenilo C3-8, cicloalcoxi C3-8, cicloalqueniloxi C3-8, bicicloalquilo C5-10, amino, alquil C1-8-amino, di-alquil C1-8-amino, alquil C1-8-carbonilo, alcoxi C1-8-carbonilo, alquil C1-8-carboniloxi, alquil C1-8-aminocarbonilo, di-alquil C1-8-aminocarbonilo, alquil C1-8-aminotiocarbonilo, di-alquil C1-8- aminotiocarbonilo, alquil C1-8-tio, alquil C1-8-sulfinilo, alquil C1-8-sulfonilo, alquil C1-8-sulfoxilo, arilo C6-14, halogenoarilo C6-14, ariloxi C6-14, ariI C6-14-tio, aril C6-14-alcoxi C1-6, ariI C6-14-alquilo-C1-6, heterociclo de cinco a diez eslabones saturado, parcialmente insaturado o aromático, que contiene uno, dos, tres o cuatro heteroátomos del grupo de O, N y S, heterocicliloxi, heteroariloxi, heteroariltio, pudiendo estar los sistemas cíclicos parcial o totalmente halogenados y/o sustituidos con grupos alquilo C1-8 y/o halogenoalquilo C1-8; X hidrogeno, halogeno, hidroxi, ciano, NR3R4, alcoxi C,1-8, halogenoalcoxi C1-8, alquil C1-8-tio, alquil C1-8-sulfinilo, alquil C1-8-sulfonilo, poseyendo R3 y R4, de manera independiente, los significados indicados para R1 o R2; Y hidrogeno, halogeno, ciano, alquilo C1-8, halogenoalquilo C1-8, alquenilo C2-8, halogenoalquenilo C2-8, alquinilo C2- 8, halogenoalquiniIo C2-8, alcoxi C1-8, halogenoalcoxi C1-8, cicloalquilo C3-8, halogenocicloalquilo C3-8, alquil C1-8-tio, alquil C1-8-sulfinilo o alquil C1-8-sulfonilo, y sus sales aceptables en agricultura.The compounds of the present are useful in agriculture. Claim 1: 7-Amino-6-heteroaryl-1,2,4-triazolo [1,5-a] pyrimidines characterized in that it has the formula (1) in which the substituents Het, R1, R2, X and Y have the following meanings: Het represents a five-link heteroaryl group containing two nitrogen atoms as ring links, which is selected from 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl and 1,2,5-oxadiazolyl, and Het may be unsubstituted or substituted with one or two L; L halogen, cyano, nitro, hydroxy, cyanate (OCN), C1-8 alkyl, C1-6 halogenoalkyl, C2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkynyl C4-8 alkynyl, C4 halogenalkyl -10, C1-8 alkoxy, C1-8 halogenoalkoxy, C2-8 alkenyloxy, C2-8 halogenoalkenyloxy, C2-8 alkyloxyC2-8, C2-8 halogenoalkyloxy, C3-8 cycloalkyl, C3-8 halocycloalkyl, C3-8 cycloalkenyl, C3-8 halogenocycloalkenyl, C3-8 cycloalkoxy, C1-8 alkoxythino-C1-8 alkyl, C2-8 alkenyloximino-C1-8 alkyl, C2-8 alkyloximino-C1-8 alkyl, C1-8 alkyl) -thio, S ( = O) nA1, C (= O) A2, C (= S) A2, NR5R6, NR5- (C = O) -R6; where n represents 0, 1 or 2; A1 means hydrogen, hydroxy, C1-8 alkyl, C1-8 halogenoalkyl, amino, C1-8-amino alkyl or C1-8-dialkyl amino, A2 means one of the groups mentioned in A1, or C 2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkynyl, C1-8 alkoxy, C1-8 halogenoalkoxy, C2-8 alkenyloxy, C2-8 halogenoalkenyloxy, C2-8 alkyloxy, C3-8 halogenoa, C3-8 cycloalkoxy C3-8 halogenocyclic or C3-8; R5, R6, independently of each other, mean hydrogen, C1-8 alkyl, C1-8 halogenoalkyl, C2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkyl, C3-8 cycloalkyl, C3 halogen -8, C3-8 cycloalkenyl or C3-8 halogenocycloalkenyl wherein the aliphatic groups of the definitions of radicals L can, for their part, carry from one to four RL groups, the same or different: RL halogen, cyano, C1-8 alkoxy , C2-8 alkenyloxy, C2-8 alkynyloxy, C3-8 cycloalkyl, C3-8 cycloalkenyl, C3-8 cycloalkyloxy, C3-8 cycloalkenyloxy, C1-8-imino-C1-8 alkoxy, C2-8-imino-alkenyloxy C1-8 alkyl, C2-8 alkynyloxy-C1-8 alkyl, S (= O) nA1, C (= O) A2, C (= S) A2, NR5R6, NR5- (C = O) -R6; R1, R2, independently of one another, hydrogen, C1-8 alkyl, C1-8 halogenoalkyl, C2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkyl, C4-10 alkydienyl, C4- halogenalkylienyl 10, C1-8 alkoxy, C1-8 halogenoalkoxy, C2-8 alkenyloxy, C2-8 halogenoalkenyloxy, C2-8 alkyloxy, C2-8 halogenoalkyloxy, C3-8 cycloalkyl, C3-8 halogenocycloalkyl, C3-8 halocycloalkenyl 8, C3-8 cycloalkoxy, C3-8 halogenocycloalkoxy, C5-10 bicycloalkyl, amino, C1-8-amino alkyl, di- C1-8-amino-alkyl, phenyl, naphthyl or a five- or six-link heterocycle, partially saturated unsaturated, or aromatic, containing one, two, three or four heteroatoms of the group of O, N and S; and R1 R2 may also form, together with the nitrogen atom to which they are attached, a five or six link heterocycle, saturated, partially unsaturated, or aromatic, which may contain one, two or three additional heteroatoms of the group of O, N and S as ring links, wherein R1 and / or R2, or a heterocycle formed from R1 and R2, can carry one, two, three or four Ra groups, the same or different, and / or two substituents attached to atoms of the neighboring ring may represent C1-6 alkylene, C2-4 oxyalkylene or C1-3-oxi alkylene; wherein Ra means: halogen, cyano, nitro, hydroxy, carboxyl, amino, C1-8 alkyl, C1-8 halogenoalkyl, C2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkyl, C4- alkydienyl 10, C1-8 alkoxy, C1-8 halogenoalkoxy, C2-8 alkenyloxy, C2-8 halogenoalkenyloxy, C2-8 alkyloxy, C2-8 halogenoalkyloxy, C3-8 cycloalkyl, C3-8 halogenocycloalkyl, C3-8 cycloalkenyl 8, C3-8 halogenocycloalkoxy, C3-8 cycloalkenyloxy, C5-10 cycloalkyl, C1-8 alkylcarbonyl, C1-8 alkoxycarbonyl, C1-8 alkylcarbonyloxy, C1-8-amino alkyl, di-C1- alkyl alkyl 8-amino, C 1-8 alkyl aminocarbonyl, di C 1-8 alkyl aminocarbonyl, C 1-8 alkyl aminothiocarbonyl, di C 1-8 alkyl aminothiocarbonyl, C 1-6 oxy alkyleneoxy, C 1-8 thio alkyl, C1-8-sulfinyl alkyl, C1-8-sulfonyl alkyl, C1-8-sulfoxyl alkyl, phenyl, naphthyl, five to ten saturated, partially unsaturated or aromatic heterocycle, containing one, two, three or four heteroatoms of the group from O, N and S; being able to carry the aliphatic, alicyclic or aromatic groups of Ra, meanwhile, one, two or three Rb groups, the same or different: Rb halogen, cyano, nitro, hydroxy, carboxyl, mercapto, amino, formyl, aminocarbonyl, aminothiocarbonyl, alkyl C1-8, halogenalkyl C1-8, alkenyl C2-8, halogenoalkenyl C2-8, alkydienyl C4-10, alkynyl C2-8, halogenoalkyne C2-8, alkoxy C1-8, halogenoalkoxy C1-8, alkenyloxy C2-8, alkyloxy C2-8, C3-8 cycloalkyl, C3-8 cycloalkenyl, C3-8 cycloalkoxy, C3-8 cycloalkenyloxy, C5-10 bicycloalkyl, amino, C1-8-alkyl, di-C1-8-alkyl, C1- alkyl 8-carbonyl, C 1-8 alkoxycarbonyl, C 1-8 alkylcarbonyloxy, C 1-8 alkylcarbonyl, diC 1-8 alkyl aminocarbonyl, C 1-8 alkyl aminothiocarbonyl, C 1-8 alkyl aminothiocarbonyl, C1-8-thio alkyl, C1-8-sulfinyl alkyl, C1-8-sulfonyl alkyl, C1-8-sulfoxyl alkyl, C6-14 aryl, C6-14 halogenoaryl, C6-14 aryloxy, C6-14-thio aryl, C6-14 aryl-C1-6 alkoxy, C6-14 ari-C1-6 alkyl, het Erocycle five to ten links saturated, partially unsaturated or aromatic, containing one, two, three or four heteroatoms of the group of O, N and S, heterocyclyloxy, heteroaryloxy, heteroaryl, being able to be partially or totally halogenated cyclic systems and / or substituted with C1-8 alkyl and / or C1-8 halogenoalkyl groups; X hydrogen, halogen, hydroxy, cyano, NR3R4, C 1-8 alkoxy, C1-8 halogenoalkoxy, C1-8-thio alkyl, C1-8-sulfinyl alkyl, C1-8-sulfonyl alkyl, having R3 and R4, of independently, the meanings indicated for R1 or R2; And hydrogen, halogen, cyano, C1-8 alkyl, C1-8 halogenoalkyl, C2-8 alkenyl, C2-8 halogenoalkenyl, C2-8 alkynyl, C2-8 halogenoalkyl, C1-8 alkoxy, C1-8 halogenoalkoxy, C3- cycloalkyl 8, C3-8 halogenocycloalkyl, C1-8-thio alkyl, C1-8-sulfinyl alkyl or C1-8-sulfonyl alkyl, and their agriculturally acceptable salts.

ARP060103299A 2005-07-29 2006-07-28 COMPOUNDS OF 7-AMINO-6-HETEROARIL-1,2,4-TRIAZOLO [1,5-A] PYRIMIDINE AND ITS EMPLOYMENT TO COMBAT DANGINE FUNGES AR055103A1 (en)

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AR (1) AR055103A1 (en)
GT (1) GT200600344A (en)
PE (1) PE20070229A1 (en)
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WO (1) WO2007012642A1 (en)

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* Cited by examiner, † Cited by third party
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WO2007101870A1 (en) * 2006-03-08 2007-09-13 Basf Se Substituted triazolopyrimidines, methods for the production thereof and use thereof for controlling parasitic fungi and agents containing the latter
US9133123B2 (en) 2010-04-23 2015-09-15 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
AR081331A1 (en) 2010-04-23 2012-08-08 Cytokinetics Inc AMINO- PYRIMIDINES COMPOSITIONS OF THE SAME AND METHODS FOR THE USE OF THE SAME
AR081626A1 (en) 2010-04-23 2012-10-10 Cytokinetics Inc AMINO-PYRIDAZINIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USE OF THE SAME TO TREAT CARDIAC AND SKELETIC MUSCULAR DISORDERS
US8759380B2 (en) 2011-04-22 2014-06-24 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use

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IL108731A (en) * 1993-03-04 1997-03-18 Shell Int Research 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES
DE10063115A1 (en) * 2000-12-18 2002-06-27 Bayer Ag triazolopyrimidines
DE10328481A1 (en) * 2003-06-25 2005-01-13 Bayer Ag triazolopyrimidines

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