BR112020026929A2 - Tiofenocarboxamidas substituídas e análogos como agentes antibacterianos - Google Patents
Tiofenocarboxamidas substituídas e análogos como agentes antibacterianos Download PDFInfo
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- BR112020026929A2 BR112020026929A2 BR112020026929-8A BR112020026929A BR112020026929A2 BR 112020026929 A2 BR112020026929 A2 BR 112020026929A2 BR 112020026929 A BR112020026929 A BR 112020026929A BR 112020026929 A2 BR112020026929 A2 BR 112020026929A2
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- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
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- 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
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
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Abstract
a presente invenção refere-se a tiofeno carboxamidas substituídas e análogos das mesmas de fórmula (ii) que podem ser usadas para proteger plantas de doenças bacterianas, em particular, de doenças bacterianas causadas por bactérias pertencentes ao gênero xanthomonas.
Description
Relatório Descritivo da Patente de Invenção para "TIOFENOCARBOXAMIDAS SUBSTITUÍDAS E ANÁLOGOS COMO AGENTES ANTIBACTERIANOS".
[001] A presente invenção refere-se a tiofeno carboxamidas substituídas e análogos das mesmas que podem ser usadas para proteger plantas de doenças bacterianas, em particular, causadas por bactérias pertencentes ao gênero Xanthomonas.
[002] Bactérias patogênicas de plantas podem causar graves doenças economicamente prejudiciais em todo o mundo. Bactérias pertencentes ao gênero Xanthomonas estão entre as bactérias fitopatogênicas consideradas as mais devastadoras. Eles são os agentes causais de várias doenças em diferentes plantas hospedeiras de importância agronômica. Exemplos de tais doenças incluem manchas bacterianas (causadas por Xanthomonas campestris pv. Vesicatoria) afetando pimenta e tomate, podridão negra de crucíferas (causada por Xanthomonas campestris pv. Campestris) afetando todas as brássicas cultivadas (por exemplo, couve de Bruxelas, repolho, couve-flor e brócolis), cancro cítrico (causadas por Xanthomonas axonopodis pv. citri) afetando espécies cítricas (lima, laranja, toranja, pummelo), crestamento bacteriano das folhas (causado por Xanthomonas oryzae pv. oryzae) afetando arroz, mancha foliar (causada por Xanthomonas arboricola pv. pruni) afetando espécies de Prunus (por exemplo, damasco, ameixa, pêssego), crestamento bacteriano comum (causado por Xanthomonas phaseoli) afetando feijão, crestamento bacteriano da mandioca (causado por Xanthomonas axonopodis pv. manihotis) afetando a mandioca, e mancha angular da folha/crestamento bacteriano (causado por Xanthomonas campestris pv. malvacearum) afetando o algodão.
[003] As doenças bacterianas das plantas podem ser controladas de diferentes maneiras, incluindo principalmente o uso de variedades de plantas resistentes a doenças e o uso de bactericidas (naturais ou sintéticos). A crise de resistência a antibióticos na medicina e o surgimento de alguns patógenos de plantas resistentes a antibióticos têm desencadeado o desenvolvimento de alternativas aos antibióticos, a fim de preservar sua eficácia e ampliar o escopo de soluções de gerenciamento de doenças. Portanto, foram desenvolvidos produtos que não agem diretamente sobre as bactérias patogênicas, ou seja, que não têm efeito antibiótico direto, mas que estimulam o próprio sistema de defesa das plantas. Esses produtos são conhecidos como ativadores de defesa vegetal. Exemplos de ativadores de defesa de plantas incluem Acibenzolar-S-metila (comercializado como Bion® e Actigard®), ácido 2,6-dicloroisonicotínico, ácido β-aminobutírico, probenazol (Oryzemate®), ácido salicílico, riboflavina, prohexadiona- cálcio, fosfonato de potássio, proteína harpina (Messenger®) e jasmonato de metila.
[004] Embora muitos compostos orgânicos e inorgânicos diferentes tenham demonstrado ativar a resistência induzida em plantas, apenas alguns produtos são atualmente comercializados.
[005] Portanto, permanece a necessidade de fornecer novos produtos químicos e métodos que permitam controlar de forma eficiente doenças bacterianas, em particular doenças causadas por bactérias pertencentes ao gênero Xanthomonas, em dose baixa, sem interagir diretamente com a bactéria de modo a prevenir o desenvolvimento de resistência. Como os produtos químicos não interagem diretamente com as bactérias, é improvável que desenvolvam resistência a esses produtos químicos.
[006] Os inventores evidenciaram que novos produtos químicos pertencentes à classe de derivados de tiofenocarboxamidas substituídas estão oferecendo uma solução para o problema acima.
[007] Alguns derivados de tiofenocarboxamida substituída são conhecidos por serem úteis para combater doenças de plantas. Por exemplo, a US 5.534.541 divulga derivados de ácido halógeno-tiofeno- carboxílico que são úteis para proteger plantas de ataques por microrganismos que danificam as plantas, tais como fungos e bactérias, por meio de uma ação direta ou sistêmica. No entanto, esses compostos foram considerados pelos presentes inventores como sendo pouco eficientes contra Xanthomonas campestris pv. campestris em dose baixa.
[008] Outros exemplos de derivados de ácido halógeno-tiofeno- carboxílico são divulgados no WO2004/024692. Esses derivados são considerados eficazes no controle de doenças fúngicas. Eles exerceriam sua ação por meio de um efeito direto sobre os microrganismos indesejáveis, mas também graças a um efeito indutor de resistência nas plantas. O WO2004/024692 também sugere que esses compostos podem ser úteis no controle de doenças bacterianas, mas não fornece quaisquer evidências de tal atividade.
[009] A presente invenção refere-se a compostos de fórmula (II) conforme divulgado neste documento, bem como a processos e intermediários para sua preparação.
[0010] A presente invenção também se refere a um método para controlar doenças bacterianas conforme divulgado neste documento.
[0011] O termo "C1-C6-alquila" como usado neste documento refere-se a uma cadeia hidrocarboneto saturada, ramificada ou reta tendo 1, 2, 3, 4, 5 ou 6 átomos de carbono. Exemplos de C1-C6-alquila incluem, mas sem limitação, metila, etila, propila (n-propila), 1-metiletila (iso-propila), butila (n-butila), 1-metilpropila (sec-butila), 2-metilpropila
(iso-butila), 1,1-dimetiletila (terc-butila), pentila, 1-metilbutila, 2- metilbutila, 3-metilbutila, 2,2-dimetilpropila, 1-etilpropila, 1,1- dimetilpropila, 1,2-dimetilpropila, hexila, 1-metilpentila, 2-metilpentila, 3- metilpentila, 4-metilpentila, 1,1-dimetilbutila, 1,2-dimetilbutila, 1,3- dimetilbutila, 2,2-dimetilbutila, 2,3-dimetilbutila, 3,3-dimetilbutila, 1- etilbutila, 2-etilbutila, 1,1,2-trimetilpropila, 1,2,2-trimetilpropila, 1-etil-1- metilpropila e 1-etil-2-metilpropila. Particularmente, a referida cadeia hidrocarboneto tem 1, 2, 3 ou 4 átomos de carbono ("C1-C4-alquila"), por exemplo, metila, etila, propila, iso-propila, butila, sec-butila, iso-butila ou terc-butila.
[0012] O termo "haloalquila", como usado neste documento, deve ser entendido como preferencialmente significando alquil ramificado e não ramificado, como definido supra, em que um ou mais dos substituintes de hidrogênio são substituídos da mesma forma ou diferentemente com halogênio. Particularmente preferencialmente, o referido haloalquil é, por exemplo, clorometila, fluoropropila, fluorometila, difluorometila, triclorometila, 2,2,2-trifluoroetila, pentafluoroetila, bromobutila, trifluorometila, iodoetila, e isômeros dos mesmos.
[0013] O termo "cicloalquila", como usado neste documento, refere- se a um anel contendo carbono monocíclico não aromático, tendo 3 a 8 átomos de carbono. Exemplos de cicloalquil saturado incluem, mas sem limitação, grupo ciclopropila, ciclobutila, ciclopentila, ciclohexila, cicloheptila, ciclooctila, ciclononila e ciclodecila.
[0014] O termo "alquenila", como usado neste documento, deve ser entendido como preferencialmente significando alquenil ramificado e não ramificado, por exemplo, um grupo vinila, propen-1-ila, propen-2-ila, but-1-en-1-ila, but-1-en-2-ila, but-2-en-1-ila, but-2-en-2-ila, but-1-en-3- ila, 2-metil-prop-2-en-1-ila, ou 2-metil-prop-1-en-1-ila.
[0015] O termo "alquinila", como usado neste documento, deve ser entendido como preferencialmente significando alquinil ramificado e não ramificado, por exemplo, um grupo etinila, prop-1-in-1-ila, but-1-in-1-ila, but-2-in-1-ila, ou but-3-in-1-ila.
[0016] O termo "arila", como usado neste documento, refere-se a um sistema de anel hidrocarboneto aromático, compreendendo de 6 a 15 átomos de carbono, ou de 6 a 12 átomos de carbono, preferencialmente de 6 a 10 átomos de carbono. O sistema de anel pode ser sistema de anel aromático monocíclico ou policíclico fundido (por exemplo, bicíclico ou tricíclico). Exemplos de aril incluem, mas sem limitação, fenila, azulenila, naftila e fluorenila. Compreende-se ainda que quando o referido grupo arila é substituído com um ou mais substituintes, o(s) referido(s) substituinte(s) pode estar em quaisquer posições no(s) refereido(s) anel(éis) arila. Particularmente, no caso de aril ser um grupo fenila, o(s) referido(s) substituinte(s) pode(m) ocupar uma ou ambas as posições orto, uma ou ambas as posições meta, ou a posição para, ou qualquer combinação dessas posições. Essa definição também se aplica a aril como parte de um substituinte compósito (por exemplo, arilóxi).
[0017] O termo "aralquila", como usado neste documento, refere-se a uma C1-C6-alquila substituída por uma arila como definido neste documento. Exemplo de aralquila inclui o grupo benzila (-CH2-C6H5).
[0018] Descobriu-se que os compostos de fórmula (II), como mostrados abaixo, eficientemente controlam doenças causadas por bactéria do gênero Xanthomonas em baixa dose (isto é, dose tão baixa quanto 31 ppm) enquanto não apresentam ação bactericida direta.
[0019] A presente invenção refere-se a compostos de fórmula (II):
(II) em que R1, R2 e R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6- alquenila, C2-C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6- alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; R7 é um átomo de hidrogênio ou uma C1-C6-alquila.
[0020] Não englobados neste documento são os compostos resultantes de combinações que são contra as leis naturais e que o versado na técnica excluiria, portanto, com base nos seus conhecimentos de perito. Por exemplo, estruturas em anel com três ou mais átomos de oxigênio adjacentes são excluídas.
[0021] Dependendo da natureza dos substituintes, o composto de fórmula (II) pode estar presente na forma de diferentes estereoisômeros. Esses estereoisômeros são, por exemplo, enantiômeros, diastereômeros, atropisômeros ou isômeros geométricos. Por conseguinte, a invenção abrange tanto estereoisômeros puros quanto qualquer mistura desses isômeros. Onde um composto pode estar presente em duas ou mais formas tautoméricas em equilíbrio, a referência ao composto por meio de uma descrição tautomérica deve ser considerada para incluir todas as formas tautoméricas.
[0022] Qualquer um dos compostos da presente invenção também pode existir em uma ou mais formas geométricas de isômeros dependendo do número de ligações duplas no composto. Isômeros geométricos por natureza de substituintes sobre uma ligação dupla ou um anel podem ser presentes na forma cis (= Z-) ou trans (= E-). A invenção, portanto, se refere igualmente a todos os isômeros geométricos e a todas as misturas possíveis, em todas as proporções.
[0023] O composto de fórmula (II) pode estar adequadamente na sua forma livre, forma de sal, forma de N-óxido ou forma de solvato (por exemplo, hidrato).
[0024] Dependendo da natureza dos substituintes, o composto de fórmula (II) pode estar presente na forma de composto livre e/ou um sal do mesmo, tal como um sal agroquimicamente ativo.
[0025] Sais agroquimicamente ativos incluem sais de adição de ácido de ácidos inorgânicos e orgânicos, bem como sais de bases usuais. Exemplos de ácidos inorgânicos são os ácidos hidro-hálicos, tais como fluoreto de hidrogênio, cloreto de hidrogênio, brometo de hidrogênio e iodeto de hidrogênio, ácido sulfúrico, ácido fosfórico e ácido nítrico, e sais ácidos, tais como bissulfato de sódio e bissulfato de potássio. Ácidos orgânicos úteis incluem, por exemplo, ácido fórmico, ácido carbônico e ácidos alcanoicos, tais como ácido acético, ácido trifluoroacético, ácido tricloroacético e ácido propiônico, e também ácido glicólico, ácido tiociânico, ácido láctico, ácido succínico, ácido cítrico, ácido benzoico, ácido cinâmico, ácido oxálico, ácidos graxos saturados ou mono- ou di-insaturados tendo 6 a 20 átomos de carbono, monoésteres alquilsulfúricos, ácidos alquilsulfônicos (ácidos sulfônicos tendo radicais alquil de cadeia linear ou ramificados tendo 1 a 20 átomos de carbono), ácidos arilsulfônicos ou ácidos arildissulfônicos (radicais aromáticos, tais como fenila e naftila, que possuem um ou dois grupos de ácido sulfônico), ácidos alquilfosfônicos (ácidos fosfônicos tendo radicais alquil ramificado ou de cadeia linear tendo 1 a 20 átomos de carbono), ácidos arilfosfônicos ou ácidos arildifosfônicos (radicais aromáticos, tais como fenila e naftila, que carregam um ou dois radicais de ácido fosfônico), em que os radicais alquila e arila podem possuir outros substituintes, por exemplo, ácido p-toluenossulfônico, ácido salicílico, ácido p-aminossalicílico, ácido 2-fenoxibenzoico, ácido 2- acetoxibenzoico etc.
[0026] Os solvatos dos compostos de fórmula (II) ou seus sais são composições estequiométricas dos compostos com solventes.
[0027] Os compostos de fórmula (II) podem existir em múltiplas formas cristalinas e/ou amorfas. As formas cristalinas incluem as formas cristalinas não solvatadas, solvatos e hidratos.
[0028] Em algumas modalidades, na fórmula (I) acima, R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2- metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2- C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio.
[0029] Exemplos não limitantes de grupos R4 adequados incluem qualquer um dos grupos R4 divulgados na coluna "R4" da Tabela II.1.
[0030] Em algumas modalidades, na fórmula (II) acima, R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6- alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2-C6- alquinila, ciclopropila, fenila, benzila, -C1-C6-alquil-Si(C1-C6-alquil)3 e - C1-C6-alquil-ciclopropila;.
[0031] Exemplos não limitantes de grupos R6 adequados incluem qualquer um dos grupos R6 divulgados na coluna "R6" da Tabela II.1.
[0032] Em algumas modalidades, na fórmula (II) acima, R7 é um átomo de hidrogênio ou uma metila.
[0033] As definições especificadas acima de R4, R6 e R7 podem ser combinadas de várias maneiras para prover subclasses de compostos de acordo com a invenção.
[0034] Exemplos não limitantes de subclasses de compostos incluem as subclasses descritas neste documento abaixo.
[0035] Em algumas modalidades, compostos da presente invenção são compostos de fórmula (II): (II) em que R1, R2 e R3 são um átomo de cloro; R4 é um átomo de hidrogênio ou isobutila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é um átomo de hidrogênio ou uma C1-C6-alquila, preferencialmente um átomo de hidrogênio ou uma C1-C4-alquila, mais preferencialmente um átomo de hidrogênio, metila ou etila.
[0036] Os compostos de fórmula (II) podem ser usados para controlar doenças bacterianas, em particular, para controlar doenças causadas por bactérias pertencentes ao gênero Xanthomonas. Processos para a preparação de compostos de fórmula (II)
[0037] A presente invenção refere-se a processos para a preparação de compostos de fórmula (II). Os compostos de fórmula (II) podem ser preparados por várias rotas em analogia a processos conhecidos (ver referências aqui), e por uma ou mais das seguintes rotas sintéticas descritas neste documento abaixo e na parte experimental. Rotas sintéticas gerais para os compostos de fórmula (II)
[0038] Salvo indicação em contrário, a seguir, R1, R2, R3, R4, R5, R6 e R7 têm o mesmo significado que fornecido acima para compostos de fórmula (II). Processo A2
[0039] Os compostos de fórmula (II), como definidos neste documento, podem ser preparados por um processo A2 que compreende a etapa de reagir um composto de fórmula (XIV) ou um de seus sais com um composto de fórmula (XV) ou um de seus sais como ilustrado pelo seguinte esquema de reação: (XIV) (XV) (II) Processo A2 em que U1 é um átomo de halogênio, um grupo hidróxi ou um grupo C1- C6-alcóxi.
[0040] Quando U1 representa um grupo hidróxi, o processo A2 é vantajosamente conduzido na presença de um agente de condensação. Agentes de condensação adequados podem ser selecionados na lista não limitada que consiste em formador de haleto de ácido, tal como fosgênio, tribrometo de fósforo, tricloreto de fósforo, pentacloreto de fósforo, óxido de tricloreto de fósforo, cloreto de oxalila ou cloreto de tionila; formador de anidrido, tal como cloroformiato de etila, cloroformiato de etilacloroformiato de metila, cloroformiato de isopropila, cloroformiato de isobutila ou cloreto de metanossulfonila; carbodiimidas, tais como N,N’-diciclohexilcarbodiimida (DCC), cloridrato de N-(3- Dimetilaminopropil)-N′-etilcarbodiimida (EDC) ou outros agentes de condensação habituais, tais como pentóxido de fósforo, ácido polifosfórico, cloreto de bis(2-oxo-3-oxazolidinil)fosfínico, 3-óxido hexafluorofosfato de 1-[bis(dimetilamino)metileno]-1H-1,2,3- triazolo[4,5-b]piridínio (HATU), tetrafluoroborato de 2-(1H-Benzotriazol- 1-il)-1,1,3,3-tetrametilamínio (TBTU), hexafluorofosfato de (1-ciano-2- etoxi-2-oxoetilidenaminooxi)dimetilamino-morfolino-carbênio, N,N’- carbonil-diimidazol, 2-etoxi-N-etoxicarbonil-1,2-dihidroquinolina (EEDQ), trifenilfosfina/tetracloro-metano, cloreto hidrato de 4-(4,6- dimetoxi[1.3.5]-triazin-2-il)-4-metilmorfolínio, cloreto de bis(2-oxo-3- oxazolidinil)fosfínico (BOP-Cl), bromo-tripirrolidinofosfônio- hexafluorofosfato (PyBroP), cloreto de 2-cloro-1,3-dimetilimidazolínio (DMC) ou anidrido propanofosfônico (T3P).
[0041] Quando U1 representa um átomo de halogênio, o processo A2 é vantajosamente conduzido na presença de um aglutinante ácido. Os aglutinantes ácidos adequados para a realização do processo A2 são, em cada caso, todas as bases inorgânicas e orgânicas usuais para tais reações. É dada preferência a carbonatos de metal alcalino, tais como carbonato de césio, carbonato de sódio, carbonato de potássio, bicarbonato de potássio, bicarbonato de sódio, acetatos de metal alcalino-terroso, tais como acetato de sódio, acetato de potássio, acetato de cálcio e também aminas terciárias, tais como trimetilamina, trietilamina, diisopropiletilamina, tributilamina, N,N-dimetilanilina, N- metilpiperidina, N,N-dimetilpiridin-4-amina, diazabiciclooctano (DABCO), diazabiciclo-noneno (DBN) ou diazabicicloundeceno (DBU), ou bases aromáticas, tais como piridina.
[0042] Quando U1 representa um grupo C1-C6-alcóxi, o processo A2 pode ser conduzido com um excesso do componente amina, opcionalmente na presença de um ácido de Lewis, tal como trimetilalumínio.
[0043] Se apropriado, o processo A2 pode ser realizado na presença de uma base e, se apropriado, na presença de um solvente,
preferencialmente em condições anidras.
[0044] Os solventes adequados para a realização do processo A2 não são particularmente limitados. Podem ser solventes orgânicos inertes habituais, desde que não dissolvam o composto para reagir com eles ou exibam qualquer interação particular com eles. É dada preferência ao uso de hidrocarbonetos opcionalmente halogenados, alifáticos, alicíclicos ou aromáticos, tais como éter de petróleo, pentano, hexano, heptano, ciclohexano, metilciclohexano, benzeno, tolueno, xileno, decalina, ISOPARTM E ou ISOPARTM G, clorobenzeno, diclorobenzeno, diclorometano, clorofórmio, tetracloreto de carbono, 1,2-dicloroetano ou tricloroetano; éteres, tais como dietil éter, diisopropil éter, metil terc-butil éter, metil terc-amil éter, dioxano, tetrahidrofurano, 2-metiltetrahidrofurano, 1,2-dimetoxietano, 1,2-dietoxietano ou anisol; nitrilas, tais como acetonitrila, propionitrila, n- ou iso-butironitrila ou benzonitrila; amidas, tais como N,N-dimetilformamida, N,N- dimetilacetamida, N-metilformanilida, N-metilpirrolidona ou triamida hexametilfosfórica; ureias, tais como 1,3-dimetil-3,4,5,6-tetra-hidro- 2(1H)-pirimidinona; ésteres, tais como acetato de metila ou acetato de etila, sulfóxidos, tais como dimetil sulfóxido, ou sulfonas, tais como sulfolano; e uma mistura dos mesmos.
[0045] O processo A2 pode ser realizado em uma atmosfera inerte, tal como atmosfera de argônio ou nitrogênio. Ao realizar o processo A2, 1 mol ou um excesso de composto de fórmula (XV) e de 1 a 5 moles de base podem ser emplegados por mol de composto de fórmula (XIV). É também possível empregar os componentes de reação em outras proporções. O trabalho é realizado por métodos conhecidos.
[0046] Os compostos de fórmula (XV) são comercialmente disponíveis ou podem ser preparados por processos bem conhecidos.
[0047] Os compostos de fórmula (XIV), em que U1 representa um grupo hidróxi, são comercialmente disponíveis ou podem ser preparados a partir de compostos de fórmula (XIV), em que U1 representa um grupo C1-C6-alcóxi por processos bem conhecidos, tais como hidrólise básica, ou podem ser preparados por processos conhecidos (Beilstein J. Org. Chem. 2007, 3, No. 23)
[0048] Os compostos de fórmula (XIV), em que U1 representa um halogênio são comercialmente disponíveis ou podem ser preparados a partir de compostos de fórmula (XIV), em que U1 representa um grupo hidróxi, por processos bem conhecidos.
[0049] Os compostos de fórmula (XIV), em que U1 representa um grupo C1-C6-alcóxi, podem ser preparados a partir de compostos de fórmula (XIV), em que U1 representa um grupo hidróxi por processos bem conhecidos. Processo B2
[0050] Os compostos de fórmula (II), como definidos neste documento, podem ser preparados por um processo B2 a partir de um composto de fórmula (XVI) ou um de seus sais realizando uma reação de cloração como ilustrado no seguinte esquema de reação: (XVI) (II) Processo B2 em que U10, U11 e U12 são independentemente um átomo de hidrogênio ou um átomo de cloro desde que pelo menos um de U10, U11 ou U12 seja um átomo de hidrogênio.
[0051] O Processo B2 pode ser realizado de acordo com processos conhecidos (WO2007098356).
[0052] O Processo B2 é realizado na presença de um agente de cloração e, se apropriado, na presença de um solvente.
[0053] Agentes de cloração adequados para realizar o processo B2 não são particularmente limitados, desde que sejam usados para cloração. Exemplos de agentes de cloração incluem N- clorossuccinimida, cloreto de sulfurila e 1,3-dicloro-5,5-dimetil-2,4- imidazolidinediona.
[0054] Solventes adequados para realizar o processo B2 não são particularmente limitados. Eles podem ser solventes orgânicos inertes habituais, desde que não dissolvam o composto para reagir com eles ou exibam qualquer interação particular com eles. Solventes adequados podem ser, por exemplo, os solventes divulgados em conexão com o processo A2. Para realizar o processo B2, também pode ser vantajoso utilizar um ácido orgânico, tal como ácido acético como solvente ou cossolvente. Processo C2
[0055] Compostos de fórmula (II), como definidos neste documento, podem ser preparados por um processo C2 compreendendo a etapa de realizar uma diazotação de um composto de fórmula (XVII) ou um de seus sais, seguido por uma substituição aromática para prover um composto de fórmula (II) como ilustrado no seguinte esquema de reação: (XVII) (II) Processo C2 em que U13, U14 e U15 são independentemente um grupo amino ou um átomo de cloro, desde que pelo menos um de U13, U14 ou U15 seja um grupo amino.
[0056] O processo C2 pode ser realizado de acordo com processos conhecidos (The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 e 645-657; Account of Chemical
Research (2018), 51, 496 e referências ali citadas).
[0057] Os compostos de fórmula (XVII) ou um de seus sais, como definidos neste documento, podem ser preparados por um processo compreendendo a etapa de desproteger um composto de fórmula (XVIII) ou um de seus sais, como ilustrado no seguinte esquema de reação: (XVIII) (XVII) em que U13, U14 e U15 são independentemente um grupo amino ou um átomo de cloro, desde que apenas um de U13, U14 ou U15 seja um grupo amino, U16, U17 e U18 são independentemente um grupo amino protegido ou um átomo de cloro, desde que pelo menos um de U16, U17 ou U18 seja um grupo amino protegido.
[0058] Exemplos de grupos de proteção do grupo amino incluem um grupo benzila, um grupo 4-metoxibenzila, um grupo alila, uma C1-C6- alquilsulfonila não substituída ou substituída, uma trifluorometilsulfonila, uma fenilsulfonila não substituída ou substituída, uma C1-C6- alcoxicarbonila não substituída ou substituída, uma benziloxicarbonila não substituída ou substituída, uma aliloxicarbonila, um grupo acetila ou um grupo trifluoroacetila.
[0059] O processo de desproteção pode ser realizado de acordo com processos conhecidos para remover grupos de proteção (Greene’s Protective Groups in Organic Synthesis; Peter G. M. Wuts; Wiley; Quinta Edição; 2014; 895-1194). Por exemplo, grupos de proteção terc- butoxicarbonila e benziloxicarbonila podem ser removidos em um meio ácido (por exemplo, com ácido clorídrico ou ácido trifluoroacético). Grupos de proteção benzílicos podem ser removidos hidrogenoliticamente com hidrogênio na presença de um catalisador (por exemplo, paládio sobre carvão ativado). O grupo trifluoroacetila pode ser removido em um meio básico (por exemplo, com carbonato de potássio ou hidróxido de lítio).
[0060] Os compostos de fórmula (XVII) também podem ser preparados a partir de compostos de fórmula (XIX) e compostos de fórmula (XVIII) podem ser preparados a partir de compostos de fórmula (XX) por reação com um composto de fórmula (XV) nas condições conforme descrito no processo A2: (XIX) (XX) em que U13, U14, U15, U16, U17 e U18 são como descritos neste documento e U1 é um átomo de halogênio, um grupo hidróxi ou a C1-C6-alcóxi grupo.
[0061] Os compostos de fórmula (XIX) e compostos de fórmula (XX) são comercialmente disponíveis ou podem ser preparados por processos bem conhecidos com as condições de reação similares às divulgadas para preparar compostos de fórmula (XIV).
[0062] Os compostos de fórmula (II) ou um de seus sais, em que R6 representa um átomo de hidrogênio, podem ser preparados a partir de compostos de fórmula (II), em que R6 representa C1-C6-alquila, C1-C6- haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2-C6-alquinila, C3-C8- cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6-alquil)3 e -C1-C6- alquil-ciclopropila, por processos bem conhecidos, tais como hidrólise básica.
[0063] Os compostos de fórmula (II), em que R6 representa C1-C6- alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2-C6- alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6- alquil)3 e -C1-C6-alquil-ciclopropila, podem ser preparados a partir de compostos de fórmula (II) ou um de seus sais, em que R6 representa um átomo de hidrogênio por processos bem conhecidos.
[0064] Os compostos de fórmula (II) ou um de seus sais, em que R7 representa C1-C6-alquila, podem ser preparados a partir de compostos de fórmula (II), em que R7 representa um átomo de hidrogênio, por processos bem conhecidos, tais como alquilação usando uma base, tal como hidreto de sódio e um haleto de C1-C6-alquila.
[0065] Os intermediários conforme divulgados neste documento podem ser eficazes no controle de bactérias e/ou fungos. Intermediários para a preparação de compostos de fórmula (II)
[0066] A presente invenção refere-se a intermediários para a preparação de compostos de fórmula (II).
[0067] Salvo indicação em contrário, a seguir, R1, R2, R3, R4, R5, R6 e R7 têm o mesmo significado que fornecido acima para compostos de fórmula (II).
[0068] Compostos de fórmula (XVIa) e (XVIb) são providos: (XVIa) (XVIb) em que R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2- metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2- C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila;
R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1- C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2- C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6- alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila.
[0069] Compostos de fórmula (XVIc): (XVIc) R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2- metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2- C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1- C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2- C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6- alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; desde que o composto de fórmula (XVIc) não represente: - N-[(4,5-dicloro-2-tienil)carbonil]glicina [138326-45-1], - N-[(4,5-dicloro-2-tienil)carbonil]isoleucina [138326-47-3], - N-[(4,5-dicloro-2-tienil)carbonil]leucina [138326-54-2], - N-[(4,5-dicloro-2-tienil)carbonil]leucinato de metila [138326-32-6], - N-[(4,5-dicloro-2-tienil)carbonil]isoleucinato de metila[138326-33-7], - N-[(4,5-dicloro-2-tienil)carbonil]valinato de 2,2,2-trifluoroetila [138326- 35-9], - N-[(4,5-dicloro-2-tienil)carbonil]leucinato de 2,2,2-trifluoroetila
[138326-36-0], e - N-[(4,5-dicloro-2-tienil)carbonil]isoleucinato de 2,2,2-trifluoroetila [138326-37-1].
[0070] Compostos de fórmula (XVIIa), (XVIIb) e (XVIIc) são providos: (XVIIa) (XVIIb) (XVIIc) em que R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2- metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2- C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1- C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2- C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6- alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; em que R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio, quando R6 é átomo de hidrogênio ou C1-C6-alquila.
[0071] Compostos de fórmula (XVIIIa), (XVIIIb) e (XVIIIc) são providos:
(XVIIIa) (XVIIIb) (XVIIIc) em que R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2- metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2- C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1- C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6-alquenila, C2- C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6-alquil-Si(C1-C6- alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; V é um grupo benzila, um grupo 4-metoxibenzila, um grupo alila, uma C1-C6-alcoxicarbonila não substituída ou substituída, uma benziloxicarbonila não substituída ou substituída, uma aliloxicarbonila, um grupo acetila ou um grupo trifluoroacetila; em que R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio, quando R6 é átomo de hidrogênio ou C1-C6-alquila.
[0072] Compostos de fórmula (XIXa), (XIXb) e (XIXc) são providos:
(XIXa) (XIXb) (XIXc) em que R1, R2, R3 são um átomo de cloro; U1a é um grupo hidróxi ou a C1-C6-alcóxi grupo, desde que o composto de fórmula (XIXc) não represente: - 3-amino-4,5-diclorotiofeno-2-carboxilato de metila [1621488-35-4].
[0073] Compostos de fórmula (XXa), (XXb) e (XXc) são providos: (XXa) (XXb) (XXc) em que R1, R2, R3 são um átomo de cloro; V é um grupo benzila, um grupo 4-metoxibenzila, um grupo alila, uma C1-C6-alcoxicarbonila não substituída ou substituída, uma benziloxicarbonila não substituída ou substituída, um aliloxicarbonila, um grupo acetila ou um grupo trifluoroacetila; e U1a é um grupo hidróxi ou a C1-C6-alcóxi grupo, desde que o composto de fórmula (XXc) não represente: - ácido 3-acetamido-4,5-diclorotiofeno-2-carboxílico [2090448-72-7], - 3-acetamido-4,5-diclorotiofeno-2-carboxilato de metila [632356-39-9], e - 4,5-dicloro-3-[(metoxicarbonil)amino]tiofeno-2-carboxilato de metila [35707-28-9].
[0074] Os intermediários divulgados podem ser eficazes no controle de bactérias e/ou fungos. Composições e Formulações
[0075] A presente invenção further refere-se a uma composição, em particular uma composição para controlar doenças de planta causadas por bactéria do gênero Xanthomonas compreendendo um ou mais compostos de fórmula (II) conforme divulgado neste documento acima e quaisquer misturas do mesmo.
[0076] A composição tipicamente compreende pelo menos um composto de fórmula (II) e pelo menos um auxiliar agricolamente adequado, por exemplo, veículo(s) e/ou tensoativo(s).
[0077] Um veículo é uma substância sólida ou líquida, natural ou sintética, orgânica ou inorgânica que é geralmente inerte. O veículo geralmente melhora a aplicação dos compostos, por exemplo, a plantas, partes de plantas ou sementes. Exemplos de veículos sólidos adequados incluem, mas sem limitação, sais de amônio, farinhas de rocha natural, tais como caulins, argilas, talco, calcário, quartzo, atapulgita, montmorilonita e terra diatomácea, e farinhas de rocha sintética, tais como sílica finamente dividida, alumina e silicatos. Exemplos de veículos sólidos tipicamente úteis para preparar grânulos incluem, mas sem limitação, rochas naturais trituradas e fracionadas, tais como calcita, mármore, pedra-pomes, sepiolita e dolomita, grânulos sintéticos de farinhas inorgânicas e orgânicas e grânulos de material orgânico, tal como papel, serragem, cascas de coco, espigas de milho e caules de tabaco. Exemplos de veículos líquidos adequados incluem, mas sem limitação, água, solventes orgânicos e combinações dos mesmos. Exemplos de solventes adequados incluem líquidos químicos orgânicos polares e não polares, por exemplo, das classes de hidrocarbonetos aromáticos e não aromáticos (tais como ciclohexano, parafinas, alquilbenzenos, xileno, tolueno alquilnaftalenos, hidrocarbonetos alifáticos clorados ou aromáticos clorados, tais comoobenzenos, cloroetilenos ou cloreto de metileno), álcoois e polióis (que podem opcionalmente também ser substituídos, eterificados e/ou esterificados, tais como butanol ou glicol), cetonas (tais como acetona, metil etil cetona, metil isobutil cetona ou ciclohexanona), ésteres (incluindo gorduras e óleos) e (poli)éteres, aminas substituídas e não substituídas, amidas (tais como dimetilformamida), lactamas (tais como N-alquilpirrolidonas) e lactonas, sulfonas e sulfóxidos (tais como dimetil sulfóxido). O veículo também pode ser um extensor gasoso liquefeito, isto é, líquido que é gasoso em temperatura padrão e sob pressão padrão, por exemplo, propelentes aerossol, tais como haloidrocarbonetos, butano, propano, nitrogênio e dióxido de carbono. A quantidade de veículo tipicamente varia de 1 a 99,99%, preferencialmente de 5 a 99,9%, mais preferencialmente, de 10 a 99,5%, e mais preferencialmente de 20 a 99% em peso da composição.
[0078] O tensoativo pode ser um tensoativo iônico (catiônico ou aniônico) ou não iônico, tal como emulsificante(s) iônico(s) ou não iônico(s), formador(es) de espuma, dispersante(s), agente(s) umectante(s) e quaisquer misturas do mesmo. Exemplos de tensoativos adequados incluem, mas sem limitação, sais de ácido poliacrílico, sais de ácido lignossulfônico, sais de ácido fenolsulfônico ou ácido naftalenossulfônico, policondensados de etileno e/ou óxido de propileno com álcoois graxos, ácidos graxos ou aminas graxas (ésteres de ácido graxo de polioxietileno, éteres de álcool graxo de polioxietileno, por exemplo, alquilaril poliglicol éteres), fenóis substituídos (preferencialmente alquilfenóis ou arilfenóis), sais de ésteres sulfossuccínicos, derivados de taurina (preferencialmente, alquil tauratos), ésteres fosfóricos de álcoois polietoxilados ou fenóis, ésteres graxos de polióis e derivados de compostos contendo sulfatos, sulfonatos, fosfatos (por exemplo, alquilsulfonatos, alquil sulfatos, arilsulfonatos) e hidrolisados de proteína, licores residuais de lignossulfito e metilcelulose. Um tensoativo é tipicamente utilizado quando os compostos da invenção e/ou o veículo são insolúveis em água e a aplicação é feita com água. Então, a quantidade de tensoativos tipicamente varia de 5 a 40% em peso da composição.
[0079] Outros exemplos de auxiliares adequados incluem repelentes de água, sicativos, aglutinantes (adesivo, agente de pegajosidade, agente de fixação, tal como carboximetilcelulose, polímeros naturais e sintéticos na forma de pós, grânulos ou látex, tais como goma arábica, álcool polivinílico e polivinil acetato, fosfolipídios naturais, tais como cefalinas e lecitinas, e fosfolipídios sintéticos, polivinilpirrolidona e tilose), espessantes, estabilizantes (por exemplo, estabilizantes a frio, conservantes, antioxidantes, estabilizadores de luz, ou outros agentes que melhoram a estabilidade química e/ou física), corantes ou pigmentos (tais como pigmentos inorgânicos, por exemplo, óxido de ferro, óxido de titânio e Azul da Prússia; corantes orgânicos, por exemplo, alizarina, azo e corantes de ftalocianina de metal), antiespumantes (por exemplo, antiespumantes de silicone e estearato de magnésio), conservantes (por exemplo, diclorofeno e álcool benzílico hemiformal), espessantes secundários (derivados de celulose, derivados de ácido acrílico, xantana, argilas modificadas e sílica finamente dividida), adesivos, giberelinas e auxiliares de processamento, óleos minerais e vegetais, perfumes, ceras, nutrientes (incluindo nutrientes de traço, tais como sais de ferro, manganês, boro, cobre, cobalto, molibdênio e zinco), coloides protetores, substâncias tixotrópicas, penetrantes, agentes sequestrantes e formadores de complexo.
[0080] A escolha dos auxiliares está relacionada ao modo de aplicação pretendido do composto da invenção e/ou das propriedades físicas. Além disso, os auxiliares podem ser escolhidos para conferir propriedades particulares (propriedades técnicas, físicas e/ou biológicas) às composições ou formas de uso preparadas a partir delas. A escolha de auxiliares pode permitir customizar as composições para necessidades específicas.
[0081] A composição da invenção pode ser em qualquer forma habitual, tais como soluções (por exemplo, soluções aquosas), emulsões, pós molháveis, suspensões à base de água e óleo, pós, poeira, pastas, pós solúveis, grânulos solúveis, grânulos para difusão, concentrados de suspoemulsão, produtos naturais ou sintéticos impregnados com o(s) composto(s) da invenção, fertilizantes e também microencapsulações em substâncias poliméricas. O(s) composto(s) da invenção pode estar presente na forma suspensa, emulsificada ou dissolvida.
[0082] A composição da invenção pode ser fornecida ao usuário final como formulação pronta para uso, isto é, as composições podem ser aplicadas diretamente às plantas ou sementes por um dispositivo adequado, tal como um dispositivo de pulverização ou aspersão. Alternativamente, as composições podem ser fornecidas ao usuário final na forma de concentrados que devem ser diluídos, preferencialmente com água, antes do uso.
[0083] A composição da invenção pode ser preparada de maneiras convencionais, por exemplo, misturando o(s) composto(s) da invenção com um ou mais auxiliares adequados, tal como divulgado neste documento acima.
[0084] A composição de acordo com a invenção contém geralmente de 0,01 a 99% em peso, de 0,05 a 98% em peso, preferencialmente de 0,1 a 95% em peso, mais preferencialmente de 0,5 a 90% em peso, mais preferencialmente de 1 a 80% em peso do(s) composto(s) da invenção. É possível que uma composição compreenda dois ou mais compostos da invenção. Nesse caso, os intervalos descritos referem-se à quantidade total de compostos da presente invenção. Misturas/Combinações
[0085] O(s) composto(s) e a composição da invenção podem ser misturados com outros ingredientes ativos como fungicidas, bactericidas, acaricidas, nematicidas, inseticidas, herbicidas, fertilizantes, reguladores de crescimento, fitoprotetores e/ou semioquímicos. Isso pode permitir a ampliação do espectro de atividades ou prevenir o desenvolvimento de resistência. Exemplos de fungicidas, inseticidas, acaricidas, nematicidas e bactericidas conhecidos são divulgados no Pesticide Manual, 17ª Edição.
[0086] Exemplos de fungicidas especialmente preferidos que podem ser misturados com o(s) composto(s) e a composição da invenção são:
[0087] 1) Inibidores da biossíntese de ergosterol, por exemplo, (1.001) ciproconazol, (1.002) difenoconazol, (1.003) epoxiconazol, (1.004) fenhexamida, (1.005) fenpropidina, (1.006) fenpropimorfo, (1.007) fenpirazamina, (1.008) fluquinconazol, (1.009) flutriafol, (1.010) imazalila, (1.011) imazalil sulfato, (1.012) ipconazol, (1.013) metconazol, (1.014) miclobutanila, (1.015) paclobutrazol, (1.016) procloraz, (1.017) propiconazol, (1.018) protioconazol, (1.019) pirisoxazol, (1.020) espiroxamina, (1.021) tebuconazol, (1.022) tetraconazol, (1.023) triadimenol, (1.024) tridemorfo, (1.025) triticonazol, (1.026) (1R,2S,5S)- 5-(4-clorobenzil)-2-(clorometil)-2-metil-1-(1H-1,2,4-triazol-1-ilmetil)ciclo- pentanol, (1.027) (1S,2R,5R)-5-(4-clorobenzil)-2-(clorometil)-2-metil-1- (1H-1,2,4-triazol-1-ilmetil)ciclopentanol, (1.028) (2R)-2-(1- clorociclopropil)-4-[(1R)-2,2-diclorociclopropil]-1-(1H-1,2,4-triazol-1- il)butan-2-ol, (1.029) (2R)-2-(1-clorociclopropil)-4-[(1S)-2,2-di- clorociclopropil]-1-(1H-1,2,4-triazol-1-il)butan-2-ol, (1.030) (2R)-2-[4-(4- clorofenoxi)-2-(trifluorometil)fenil]-1-(1H-1,2,4-triazol-1-il)propan-2-ol, (1.031) (2S)-2-(1-clorociclopropil)-4-[(1R)-2,2-diclorociclopropil]-1-(1H- 1,2,4-triazol-1-il)butan-2-ol, (1.032) (2S)-2-(1-clorociclopropil)-4-[(1S)- 2,2-diclorociclopropil]-1-(1H-1,2,4-triazol-1-il)butan-2-ol, (1.033) (2S)-2- [4-(4-clorofenoxi)-2-(trifluorometil)fenil]-1-(1H-1,2,4-triazol-1-il)propan-
2-ol, (1.034) (R)-[3-(4-cloro-2-fluorofenil)-5-(2,4-difluorofenil)-1,2- oxazol-4-il](piridin-3-il)metanol, (1.035) (S)-[3-(4-cloro-2-fluorofenil)-5- (2,4-difluorofenil)-1,2-oxazol-4-il](piridin-3-il)metanol, (1.036) [3-(4- cloro-2-fluorofenil)-5-(2,4-difluorofenil)-1,2-oxazol-4-il](piridin-3- il)metanol, (1.037) 1-({(2R,4S)-2-[2-cloro-4-(4-clorofenoxi)fenil]-4-metil- 1,3-dioxolan-2-il}metil)-1H-1,2,4-triazol, (1.038) 1-({(2S,4S)-2-[2-cloro- 4-(4-clorofenoxi)fenil]-4-metil-1,3-dioxolan-2-il}metil)-1H-1,2,4-triazol, (1.039) 1-{[3-(2-clorofenil)-2-(2,4-difluorofenil)oxiran-2-il]metil}-1H- 1,2,4-triazol-5-il tiocianato, (1.040) 1-{[rel(2R,3R)-3-(2-clorofenil)-2-(2,4- difluorofenil)oxiran-2-il]metil}-1H-1,2,4-triazol-5-il tiocianato, (1.041) 1- {[rel(2R,3S)-3-(2-clorofenil)-2-(2,4-difluorofenil)oxiran-2-il]metil}-1H- 1,2,4-triazol-5-il tiocianato, (1.042) 2-[(2R,4R,5R)-1-(2,4-diclorofenil)-5- hidroxi-2,6,6-trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.043) 2-[(2R,4R,5S)-1-(2,4-diclorofenil)-5-hidroxi-2,6,6-trimetilheptan- 4-il]-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.044) 2-[(2R,4S,5R)-1-(2,4- diclorofenil)-5-hidroxi-2,6,6-trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4- triazol-3-tiona, (1.045) 2-[(2R,4S,5S)-1-(2,4-diclorofenil)-5-hidroxi-2,6,6- trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.046) 2- [(2S,4R,5R)-1-(2,4-diclorofenil)-5-hidroxi-2,6,6-trimetilheptan-4-il]-2,4- dihidro-3H-1,2,4-triazol-3-tiona, (1.047) 2-[(2S,4R,5S)-1-(2,4- diclorofenil)-5-hidroxi-2,6,6-trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4- triazol-3-tiona, (1.048) 2-[(2S,4S,5R)-1-(2,4-diclorofenil)-5-hidroxi-2,6,6- trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.049) 2- [(2S,4S,5S)-1-(2,4-diclorofenil)-5-hidroxi-2,6,6-trimetilheptan-4-il]-2,4- dihidro-3H-1,2,4-triazol-3-tiona, (1.050) 2-[1-(2,4-diclorofenil)-5-hidroxi- 2,6,6-trimetilheptan-4-il]-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.051) 2- [2-cloro-4-(2,4-diclorofenoxi)fenil]-1-(1H-1,2,4-triazol-1-il)propan-2-ol, (1.052) 2-[2-cloro-4-(4-clorofenoxi)fenil]-1-(1H-1,2,4-triazol-1-il)butan-2- ol, (1.053) 2-[4-(4-clorofenoxi)-2-(trifluorometil)fenil]-1-(1H-1,2,4-triazol- 1-il)butan-2-ol, (1.054) 2-[4-(4-clorofenoxi)-2-(trifluorometil)fenil]-1-(1H-
1,2,4-triazol-1-il)pentan-2-ol, (1.055) Mefentrifluconazol, (1.056) 2-{[3- (2-clorofenil)-2-(2,4-difluorofenil)oxiran-2-il]metil}-2,4-dihidro-3H-1,2,4- triazol-3-tiona, (1.057) 2-{[rel(2R,3R)-3-(2-clorofenil)-2-(2,4- difluorofenil)oxiran-2-il]metil}-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.058) 2-{[rel(2R,3S)-3-(2-clorofenil)-2-(2,4-difluorofenil)oxiran-2- il]metil}-2,4-dihidro-3H-1,2,4-triazol-3-tiona, (1.059) 5-(4-clorobenzil)-2- (clorometil)-2-metil-1-(1H-1,2,4-triazol-1-ilmetil)ciclopentanol, (1.060) 5- (alilsulfanil)-1-{[3-(2-clorofenil)-2-(2,4-difluorofenil)oxiran-2-il]metil}-1H- 1,2,4-triazol, (1.061) 5-(alilsulfanil)-1-{[rel(2R,3R)-3-(2-clorofenil)-2-(2,4- difluorofenil)oxiran-2-il]metil}-1H-1,2,4-triazol, (1.062) 5-(alilsulfanil)-1- {[rel(2R,3S)-3-(2-clorofenil)-2-(2,4-difluorofenil)oxiran-2-il]metil}-1H- 1,2,4-triazol, (1.063) N’-(2,5-dimetil-4-{[3-(1,1,2,2- tetrafluoroetoxi)fenil]sulfanil}fenil)-N-etil-N-metilimidoformamida, (1.064) N’-(2,5-dimetil-4-{[3-(2,2,2-trifluoroetoxi)fenil]sulfanil}fenil)-N-etil-N- metilimidoformamida, (1.065) N’-(2,5-dimetil-4-{[3-(2,2,3,3- tetrafluoropropoxi)fenil]sulfanil}fenil)-N-etil-N-metilimidoformamida, (1.066) N’-(2,5-dimetil-4-{[3-(pentafluoroetoxi)fenil]sulfanil}fenil)-N-etil- N-metilimidoformamida, (1.067) N’-(2,5-dimetil-4-{3-[(1,1,2,2- tetrafluoroetil)sulfanil]fenoxi}fenil)-N-etil-N-metilimidoformamida, (1.068) N’-(2,5-dimetil-4-{3-[(2,2,2-trifluoroetil)sulfanil]fenoxi}fenil)-N-etil-N- metilimidoformamida, (1.069) N’-(2,5-dimetil-4-{3-[(2,2,3,3- tetrafluoropropil)sulfanil]fenoxi}fenil)-N-etil-N-metilimidoformamida, (1.070) N’-(2,5-dimetil-4-{3-[(pentafluoroetil)sulfanil]fenoxi}fenil)-N-etil- N-metilimidoformamida, (1.071) N’-(2,5-dimetil-4-fenoxifenil)-N-etil-N- metilimidoformamida, (1.072) N’-(4-{[3-(difluorometoxi)fenil]sulfanil}-2,5- dimetilfenil)-N-etil-N-metilimidoformamida, (1.073) N’-(4-{3-[(difluoro- metil)sulfanil]fenoxi}-2,5-dimetilfenil)-N-etil-N-metilimidoformamida, (1.074) N’-[5-bromo-6-(2,3-dihidro-1H-inden-2-iloxi)-2-metilpiridin-3-il]- N-etil-N-metilimidoformamida, (1.075) N’-{4-[(4,5-dicloro-1,3-tiazol-2- il)oxi]-2,5-dimetilfenil}-N-etil-N-metilimidoformamida, (1.076) N’-{5-
bromo-6-[(1R)-1-(3,5-difluorofenil)etoxi]-2-metilpiridin-3-il}-N-etil-N- metilimidoformamida, (1.077) N’-{5-bromo-6-[(1S)-1-(3,5- difluorofenil)etoxi]-2-metilpiridin-3-il}-N-etil-N-metilimidoformamida, (1.078) N’-{5-bromo-6-[(cis-4-isopropilciclohexil)oxi]-2-metilpiridin-3-il}- N-etil-N-metilimidoformamida, (1.079) N’-{5-bromo-6-[(trans-4- isopropilciclohexil)oxi]-2-metilpiridin-3-il}-N-etil-N-metilimidoformamida, (1.080) N’-{5-bromo-6-[1-(3,5-difluorofenil)etoxi]-2-metilpiridin-3-il}-N- etil-N-metilimidoformamida, (1.081) Ipfentrifluconazol.
[0088] 2) Inibidores da cadeia respiratória no complexo I ou II, por exemplo, (2.001) benzovindiflupir, (2.002) bixafeno, (2.003) boscalida, (2.004) carboxina, (2.005) fluopiram, (2.006) flutolanila, (2.007) fluxapiroxad, (2.008) furametpir, (2.009) Isofetamida, (2.010) isopirazam (enantiômero antiepimérico 1R,4S,9S), (2.011) isopirazam (enantiômero antiepimérico 1S,4R,9R), (2.012) isopirazam (racemato antiepimérico 1RS,4SR,9SR), (2.013) isopirazam (mistura de racemato syn-epimérico 1RS,4SR,9RS e racemato antiepimérico 1RS,4SR,9SR), (2.014) isopirazam (enantiômero syn-epimérico 1R,4S,9R), (2.015) isopirazam (enantiômero syn-epimérico 1S,4R,9S), (2.016) isopirazam (racemato syn-epimérico 1RS,4SR,9RS), (2.017) penflufen, (2.018) pentiopirad, (2.019) pidiflumetofeno, (2.020) piraziflumida, (2.021) sedaxano, (2.022) 1,3-dimetil-N-(1,1,3-trimetil-2,3-dihidro-1H-inden-4- il)-1H-pirazol-4-carboxamida, (2.023) 1,3-dimetil-N-[(3R)-1,1,3-trimetil- 2,3-dihidro-1H-inden-4-il]-1H-pirazol-4-carboxamida, (2.024) 1,3- dimetil-N-[(3S)-1,1,3-trimetil-2,3-dihidro-1H-inden-4-il]-1H-pirazol-4- carboxamida, (2.025) 1-metil-3-(trifluorometil)-N-[2’- (trifluorometil)bifenil-2-il]-1H-pirazol-4-carboxamida, (2.026) 2-fluoro-6- (trifluorometil)-N-(1,1,3-trimetil-2,3-dihidro-1H-inden-4-il)benzamida, (2.027) 3-(difluorometil)-1-metil-N-(1,1,3-trimetil-2,3-dihidro-1H-inden-4- il)-1H-pirazol-4-carboxamida, (2.028) 3-(difluorometil)-1-metil-N-[(3R)- 1,1,3-trimetil-2,3-dihidro-1H-inden-4-il]-1H-pirazol-4-carboxamida,
(2.029) 3-(difluorometil)-1-metil-N-[(3S)-1,1,3-trimetil-2,3-dihidro-1H- inden-4-il]-1H-pirazol-4-carboxamida, (2.030) fluindapir, (2.031) 3- (difluorometil)-N-[(3R)-7-fluoro-1,1,3-trimetil-2,3-dihidro-1H-inden-4-il]- 1-metil-1H-pirazol-4-carboxamida, (2.032) 3-(difluorometil)-N-[(3S)-7- fluoro-1,1,3-trimetil-2,3-dihidro-1H-inden-4-il]-1-metil-1H-pirazol-4- carboxamida, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4- (trifluorometil)piridin-2-il]oxi}fenil)etil]quinazolin-4-amina, (2.034) N-(2- ciclopentil-5-fluorobenzil)-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil- 1H-pirazol-4-carboxamida, (2.035) N-(2-terc-butil-5-metilbenzil)-N- ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (2.036) N-(2-terc-butilbenzil)-N-ciclopropil-3-(difluorometil)-5-fluoro-1- metil-1H-pirazol-4-carboxamida, (2.037) N-(5-cloro-2-etilbenzil)-N- ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (2.038) isoflucipram, (2.039) N-[(1R,4S)-9-(diclorometileno)-1,2,3,4- tetrahidro-1,4-metanonaftalen-5-il]-3-(difluorometil)-1-metil-1H-pirazol- 4-carboxamida, (2.040) N-[(1S,4R)-9-(diclorometileno)-1,2,3,4- tetrahidro-1,4-metanonaftalen-5-il]-3-(difluorometil)-1-metil-1H-pirazol- 4-carboxamida, (2.041) N-[1-(2,4-diclorofenil)-1-metoxipropan-2-il]-3- (difluorometil)-1-metil-1H-pirazol-4-carboxamida, (2.042) N-[2-cloro-6- (trifluorometil)benzil]-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H- pirazol-4-carboxamida, (2.043) N-[3-cloro-2-fluoro-6- (trifluorometil)benzil]-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H- pirazol-4-carboxamida, (2.044) N-[5-cloro-2-(trifluorometil)benzil]-N- ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (2.045) N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-N-[5-metil-2- (trifluorometil)benzil]-1H-pirazol-4-carboxamida, (2.046) N-ciclopropil-3- (difluorometil)-5-fluoro-N-(2-fluoro-6-isopropilbenzil)-1-metil-1H-pirazol- 4-carboxamida, (2.047) N-ciclopropil-3-(difluorometil)-5-fluoro-N-(2- isopropil-5-metilbenzil)-1-metil-1H-pirazol-4-carboxamida, (2.048) N- ciclopropil-3-(difluorometil)-5-fluoro-N-(2-isopropilbenzil)-1-metil-1H-
pirazol-4-carbotioamida, (2.049) N-ciclopropil-3-(difluorometil)-5-fluoro- N-(2-isopropilbenzil)-1-metil-1H-pirazol-4-carboxamida, (2.050) N- ciclopropil-3-(difluorometil)-5-fluoro-N-(5-fluoro-2-isopropilbenzil)-1- metil-1H-pirazol-4-carboxamida, (2.051) N-ciclopropil-3-(difluorometil)- N-(2-etil-4,5-dimetilbenzil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (2.052) N-ciclopropil-3-(difluorometil)-N-(2-etil-5-fluorobenzil)-5-fluoro- 1-metil-1H-pirazol-4-carboxamida, (2.053) N-ciclopropil-3- (difluorometil)-N-(2-etil-5-metilbenzil)-5-fluoro-1-metil-1H-pirazol-4- carboxamida, (2.054) N-ciclopropil-N-(2-ciclopropil-5-fluorobenzil)-3- (difluorometil)-5-fluoro-1-metil-1H-pirazol-4-carboxamida, (2.055) N- ciclopropil-N-(2-ciclopropil-5-metilbenzil)-3-(difluorometil)-5-fluoro-1- metil-1H-pirazol-4-carboxamida, (2.056) N-ciclopropil-N-(2- ciclopropilbenzil)-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol-4- carboxamida, (2.057) pirapropoina.
[0089] 3) Inibidores da cadeia respiratória no complexo III, por exemplo, (3.001) ametoctradina, (3.002) amisulbrom, (3.003) azoxistrobina, (3.004) coumetoxistrobina, (3.005) coumoxistrobina, (3.006) ciazofamida, (3.007) dimoxistrobina, (3.008) enoxastrobina, (3.009) famoxadona, (3.010) fenamidona, (3.011) flufenoxistrobina, (3.012) fluoxastrobina, (3.013) cresoxim-metila, (3.014) metominostrobina, (3.015) orisastrobina, (3.016) picoxistrobina, (3.017) piraclostrobina, (3.018) pirametostrobina, (3.019) piraoxistrobina, (3.020) trifloxistrobina, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2- fenilvinil]oxi}fenil)etilideno]amino}oxi)metil]fenil}-2-(metoxiimino)-N- metilacetamida, (3.022) (2E,3Z)-5-{[1-(4-clorofenil)-1H-pirazol-3-il]oxi}- 2-(metoxiimino)-N,3-dimetilpent-3-enamida, (3.023) (2R)-2-{2-[(2,5- dimetilfenoxi)metil]fenil}-2-metoxi-N-metilacetamida, (3.024) (2S)-2-{2- [(2,5-dimetilfenoxi)metil]fenil}-2-metoxi-N-metilacetamida, (3.025) (3S,6S,7R,8R)-8-benzil-3-[({3-[(isobutiriloxi)metoxi]-4-metoxipiridin-2- il}carbonil)amino]-6-metil-4,9-dioxo-1,5-dioxonan-7-il 2-
metilpropanoato, (3.026) mandestrobina, (3.027) N-(3-etil-3,5,5- trimetilciclohexil)-3-formamido-2-hidroxibenzamida, (3.028) (2E,3Z)-5- {[1-(4-cloro-2-fluorofenil)-1H-pirazol-3-il]oxi}-2-(metoxiimino)-N,3- dimetilpent-3-enamida, (3.029) metil {5-[3-(2,4-dimetilfenil)-1H-pirazol- 1-il]-2-metilbenzil}carbamato, (3.030) metiltetraprol, (3.031) florilpicoxamida.
[0090] 4) Inibidores da mitose e divisão celular, por exemplo, (4.001) carbendazim, (4.002) dietofencarb, (4.003) etaboxam, (4.004) fluopicolida, (4.005) pencicuron, (4.006) tiabendazol, (4.007) tiofanato- metila, (4.008) zoxamida, (4.009) 3-cloro-4-(2,6-difluorofenil)-6-metil-5- fenilpiridazina, (4.010) 3-cloro-5-(4-clorofenil)-4-(2,6-difluorofenil)-6- metilpiridazina, (4.011) 3-cloro-5-(6-cloropiridin-3-il)-6-metil-4-(2,4,6- trifluorofenil)piridazina, (4.012) 4-(2-bromo-4-fluorofenil)-N-(2,6- difluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.013) 4-(2-bromo-4- fluorofenil)-N-(2-bromo-6-fluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.014) 4-(2-bromo-4-fluorofenil)-N-(2-bromofenil)-1,3-dimetil-1H- pirazol-5-amina, (4.015) 4-(2-bromo-4-fluorofenil)-N-(2-cloro-6- fluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.016) 4-(2-bromo-4- fluorofenil)-N-(2-clorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.017) 4-(2- bromo-4-fluorofenil)-N-(2-fluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.018) 4-(2-cloro-4-fluorofenil)-N-(2,6-difluorofenil)-1,3-dimetil-1H- pirazol-5-amina, (4.019) 4-(2-cloro-4-fluorofenil)-N-(2-cloro-6- fluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.020) 4-(2-cloro-4-fluoro- fenil)-N-(2-clorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.021) 4-(2-cloro- 4-fluorofenil)-N-(2-fluorofenil)-1,3-dimetil-1H-pirazol-5-amina, (4.022) 4- (4-clorofenil)-5-(2,6-difluorofenil)-3,6-dimetilpiridazina, (4.023) N-(2- bromo-6-fluorofenil)-4-(2-cloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5- amina, (4.024) N-(2-bromofenil)-4-(2-cloro-4-fluorofenil)-1,3-dimetil-1H- pirazol-5-amina, (4.025) N-(4-cloro-2,6-difluorofenil)-4-(2-cloro-4- fluorofenil)-1,3-dimetil-1H-pirazol-5-amina.
[0091] 5) Compostos tendo uma ação multissítio, por exemplo, (5.001) mistura bordeaux, (5.002) captafol, (5.003) captano, (5.004) clorotalonila, (5.005) hidróxido de cobre, (5.006) naftenato de cobre, (5.007) óxido de cobre, (5.008) oxicloreto de cobre, (5.009) sulfato de cobre(2+), (5.010) ditianona, (5.011) dodina, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinco, (5.017) oxina-cobre, (5.018) propineb, (5.019) enxofre e preparações de enxofre incluindo polissulfeto de cálcio, (5.020) tiram, (5.021) zineb, (5.022) ziram, (5.023) 6-etil-5,7-dioxo-6,7-dihidro-5H- pirrolo[3’,4’:5,6][1,4]ditiino[2,3-c][1,2]tiazol-3-carbonitrila.
[0092] 6) compostos induzindo uma defesa do hospedeiro, por exemplo, (6.001) acibenzolar-S-metila, (6.002) isotianila, (6.003) probenazol, (6.004) tiadinila.
[0093] 7) Inibidores do aminoácido e/ou biossíntese de proteína, por exemplo, (7.001) ciprodinila, (7.002) casugamicina, (7.003) cloridrato hidrato de casugamicina, (7.004) oxitetraciclina, (7.005) pirimetanila, (7.006) 3-(5-fluoro-3,3,4,4-tetrametil-3,4-dihidroisoquinolin-1- il)quinolina.
[0094]
[0095] 8) Inibidores da produção de ATP, por exemplo, (8.001) siltiofam.9) Inibidores da síntese de parede celular, por exemplo, (9.001) bentiavalicarb, (9.002) dimetomorfo, (9.003) flumorfo, (9.004) iprovalicarb, (9.005) mandipropamida, (9.006) pirimorfo, (9.007) valifenalato, (9.008) (2E)-3-(4-terc-butilfenil)-3-(2-cloropiridin-4-il)-1- (morfolin-4-il)prop-2-en-1-ona, (9.009) (2Z)-3-(4-terc-butilfenil)-3-(2- cloropiridin-4-il)-1-(morfolin-4-il)prop-2-en-1-ona.
[0096] 10) Inibidores a síntese de lipídio e membrana, por exemplo, (10.001) propamocarb, (10.002) cloridrato de propamocarb, (10.003) tolclofos-metila.
[0097] 11) Inibidores da biossíntese de melanina, por exemplo,
(11.001) triciclazol, (11.002) {3-metil-1-[(4-metilbenzoil)amino]butan-2- il}carbamato de 2,2,2-trifluoroetila.
[0098] 12) Inibidores da síntese de ácido nucleico, por exemplo, (12.001) benalaxila, (12.002) benalaxil-M (quiralaxila), (12.003) metalaxila, (12.004) metalaxil-M (mefenoxam).
[0099] 13) Inibidores da transdução de sinal, por exemplo, (13.001) fludioxonila, (13.002) iprodiona, (13.003) procimidona, (13.004) proquinazid, (13.005) quinoxifeno, (13.006) vinclozolina.
[00100] 14) Compostos atuando como um desacoplador, por exemplo, (14.001) fluazinam, (14.002) meptildinocap.
[00101] 15) Outros compostos, por exemplo, (15.001) ácido abscísico, (15.002) bentiazol, (15.003) betoxazina, (15.004) capsimicina, (15.005) carvona, (15.006) quinometionat, (15.007) cufraneb, (15.008) ciflufenamida, (15.009) cimoxanila, (15.010) ciprossulfamida, (15.011) flutianila, (15.012) fosetil-alumínio, (15.013) fosetil-cálcio, (15.014) fosetil-sódio, (15.015) metil isotiocianato, (15.016) metrafenona, (15.017) mildiomicina, (15.018) natamicina, (15.019) dimetilditiocarbamato de níquel, (15.020) nitrotal-isopropila, (15.021) oxamocarb, (15.022) oxatiapiprolina, (15.023) oxifentiína, (15.024) pentaclorofenol e sais, (15.025) ácido fosforoso e seus sais, (15.026) propamocarb-fosetilato, (15.027) piriofenona (clazafenona), (15.028) tebufloquina, (15.029) tecloftalam, (15.030) tolnifanida, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorofenil)-4,5-dihidro-1,2-oxazol-3-il]- 1,3-tiazol-2-il}piperidin-1-il)-2-[5-metil-3-(trifluorometil)-1H-pirazol-1- il]etanona, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorofenil)-4,5-dihidro-1,2- oxazol-3-il]-1,3-tiazol-2-il}piperidin-1-il)-2-[5-metil-3-(trifluorometil)-1H- pirazol-1-il]etanona, (15.033) 2-(6-benzilpiridin-2-il)quinazolina, (15.034) dipimetitrona, (15.035) 2-[3,5-bis(difluorometil)-1H-pirazol-1-il]-1-[4-(4- {5-[2-(prop-2-in-1-iloxi)fenil]-4,5-dihidro-1,2-oxazol-3-il}-1,3-tiazol-2-il)- piperidin-1-il]etanona, (15.036) 2-[3,5-bis(difluorometil)-1H-pirazol-1-il]-
1-[4-(4-{5-[2-cloro-6-(prop-2-in-1-iloxi)fenil]-4,5-dihidro-1,2-oxazol-3-il}- 1,3-tiazol-2-il)piperidin-1-il]etanona, (15.037) 2-[3,5-bis(difluorometil)- 1H-pirazol-1-il]-1-[4-(4-{5-[2-fluoro-6-(prop-2-in-1-iloxi)fenil]-4,5-dihidro- 1,2-oxazol-3-il}-1,3-tiazol-2-il)piperidin-1-il]etanona, (15.038) 2-[6-(3- fluoro-4-metoxifenil)-5-metilpiridin-2-il]quinazolina, (15.039) 2-{(5R)-3- [2-(1-{[3,5-bis(difluorometil)-1H-pirazol-1-il]acetil}piperidin-4-il)-1,3- tiazol-4-il]-4,5-dihidro-1,2-oxazol-5-il}-3-clorofenil metanossulfonato, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluorometil)-1H-pirazol-1- il]acetil}piperidin-4-il)-1,3-tiazol-4-il]-4,5-dihidro-1,2-oxazol-5-il}-3- clorofenil metanossulfonato, (15.041) Ipflufenoquina, (15.042) 2-{2- fluoro-6-[(8-fluoro-2-metilquinolin-3-il)oxi]fenil}propan-2-ol, (15.043) metanossulfonato de 2-{3-[2-(1-{[3,5-bis(difluorometil)-1H-pirazol-1- il]acetil}piperidin-4-il)-1,3-tiazol-4-il]-4,5-dihidro-1,2-oxazol-5-il}-3- clorofenila, (15.044) metanossulfonato de 2-{3-[2-(1-{[3,5- bis(difluorometil)-1H-pirazol-1-il]acetil}piperidin-4-il)-1,3-tiazol-4-il]-4,5- dihidro-1,2-oxazol-5-il}fenila, (15.045) 2-fenilfenol e sais, (15.046) 3- (4,4,5-trifluoro-3,3-dimetil-3,4-dihidroisoquinolin-1-il)quinolina, (15.047) quinofumelina, (15.048) 4-amino-5-fluoropirimidin-2-ol (forma tautomérica: 4-amino-5-fluoropirimidin-2(1H)-ona), (15.049) ácido 4- oxo-4-[(2-feniletil)amino]butanoico, (15.050) 5-amino-1,3,4-tiadiazol-2- tiol, (15.051) 5-cloro-N’-fenil-N’-(prop-2-in-1-il)tiofeno-2- sulfonohidrazida, (15.052) 5-fluoro-2-[(4-fluorobenzil)oxi]pirimidin-4- amina, (15.053) 5-fluoro-2-[(4-metilbenzil)oxi]pirimidin-4-amina, (15.054) 9-fluoro-2,2-dimetil-5-(quinolin-3-il)-2,3-dihidro-1,4- benzoxazepina, (15.055) but-3-in-1-il {6-[({[(Z)-(1-metil-1H-tetrazol-5-il)- (fenil)metileno]amino}oxi)metil]piridin-2-il}carbamato, (15.056) etil (2Z)- 3-amino-2-ciano-3-fenilacrilato, (15.057) ácido fenazina-1-carboxílico, (15.058) propil 3,4,5-trihidroxibenzoato, (15.059) quinolin-8-ol, (15.060) sulfato de quinolin-8-ol (2:1), (15.061) terc-butil {6-[({[(1-metil-1H- tetrazol-5-il)(fenil)metileno]amino}oxi)metil]piridin-2-il}carbamato,
(15.062) 5-fluoro-4-imino-3-metil-1-[(4-metilfenil)sulfonyl]-3,4-dihidro- pirimidin-2(1H)-ona, (15.063) aminopirifeno.
[00102] Todos os parceiros de mistura nomeados das classes (1) a (15), conforme descrito acima, podem estar presentes na forma de composto livre e/ou, se seus grupos funcionais permitirem, um sal agricolamente aceitável do mesmo.
[00103] Em algumas modalidades, as combinações de composto compreendem os seguintes componentes: (II.01) + (1.001), (II.01) + (1.002), (II.01) + (1.003), (II.01) + (1.004), (II.01) + (1.005), (II.01) + (1.006), (II.01) + (1.007), (II.01) + (1.008), (II.01) + (1.009), (II.01) + (1.010), (II.01) + (1.011), (II.01) + (1.012), (II.01) + (1.013), (II.01) + (1.014), (II.01) + (1.015), (II.01) + (1.016), (II.01) + (1.017), (II.01) + (1.018), (II.01) + (1.019), (II.01) + (1.020), (II.01) + (1.021), (II.01) + (1.022), (II.01) + (1.023), (II.01) + (1.024), (II.01) + (1.025), (II.01) + (1.026), (II.01) + (1.027), (II.01) + (1.028), (II.01) + (1.029), (II.01) + (1.030), (II.01) + (1.031), (II.01) + (1.032), (II.01) + (1.033), (II.01) + (1.034), (II.01) + (1.035), (II.01) + (1.036), (II.01) + (1.037), (II.01) + (1.038), (II.01) + (1.039), (II.01) + (1.040), (II.01) + (1.041), (II.01) + (1.042), (II.01) + (1.043), (II.01) + (1.044), (II.01) + (1.045), (II.01) + (1.046), (II.01) + (1.047), (II.01) + (1.048), (II.01) + (1.049), (II.01) + (1.050), (II.01) + (1.051), (II.01) + (1.052), (II.01) + (1.053), (II.01) + (1.054), (II.01) + (1.055), (II.01) + (1.056), (II.01) + (1.057), (II.01) + (1.058), (II.01) + (1.059), (II.01) + (1.060), (II.01) + (1.061), (II.01) + (1.062), (II.01) + (1.063), (II.01) + (1.064), (II.01) + (1.065), (II.01) + (1.066), (II.01) + (1.067), (II.01) + (1.068), (II.01) + (1.069), (II.01) + (1.070), (II.01) + (1.071), (II.01) + (1.072), (II.01) + (1.073), (II.01) + (1.074), (II.01) + (1.075), (II.01) + (1.076), (II.01) + (1.077), (II.01) + (1.078), (II.01) + (1.079), (II.01) + (1.080), (II.01) + (1.081), (II.01) + (1.082), (II.01) + (1.083), (II.01) + (1.084), (II.01) + (1.085), (II.01) + (1.086), (II.01) + (2.001), (II.01) + (2.002),
(II.01) + (2.003), (II.01) + (2.004), (II.01) + (2.005), (II.01) + (2.006), (II.01) + (2.007), (II.01) + (2.008), (II.01) + (2.009), (II.01) + (2.010), (II.01) + (2.011), (II.01) + (2.012), (II.01) + (2.013), (II.01) + (2.014), (II.01) + (2.015), (II.01) + (2.016), (II.01) + (2.017), (II.01) + (2.018), (II.01) + (2.019), (II.01) + (2.020), (II.01) + (2.021), (II.01) + (2.022), (II.01) + (2.023), (II.01) + (2.024), (II.01) + (2.025), (II.01) + (2.026), (II.01) + (2.027), (II.01) + (2.028), (II.01) + (2.029), (II.01) + (2.030), (II.01) + (2.031), (II.01) + (2.032), (II.01) + (2.033), (II.01) + (2.034), (II.01) + (2.035), (II.01) + (2.036), (II.01) + (2.037), (II.01) + (2.038), (II.01) + (2.039), (II.01) + (2.040), (II.01) + (2.041), (II.01) + (2.042), (II.01) + (2.043), (II.01) + (2.044), (II.01) + (2.045), (II.01) + (2.046), (II.01) + (2.047), (II.01) + (2.048), (II.01) + (2.049), (II.01) + (2.050), (II.01) + (2.051), (II.01) + (2.052), (II.01) + (2.053), (II.01) + (2.054), (II.01) + (2.055), (II.01) + (2.056), (II.01) + (3.001), (II.01) + (3.002), (II.01) + (3.003), (II.01) + (3.004), (II.01) + (3.005), (II.01) + (3.006), (II.01) + (3.007), (II.01) + (3.008), (II.01) + (3.009), (II.01) + (3.010), (II.01) + (3.011), (II.01) + (3.012), (II.01) + (3.013), (II.01) + (3.014), (II.01) + (3.015), (II.01) + (3.016), (II.01) + (3.017), (II.01) + (3.018), (II.01) + (3.019), (II.01) + (3.020), (II.01) + (3.021), (II.01) + (3.022), (II.01) + (3.023), (II.01) + (3.024), (II.01) + (3.025), (II.01) + (3.026), (II.01) + (3.027), (II.01) + (3.028), (II.01) + (3.029), (II.01) + (3.030), (II.01) + (4.001), (II.01) + (4.002), (II.01) + (4.003), (II.01) + (4.004), (II.01) + (4.005), (II.01) + (4.006), (II.01) + (4.007), (II.01) + (4.008), (II.01) + (4.009), (II.01) + (4.010), (II.01) + (4.011), (II.01) + (4.012), (II.01) + (4.013), (II.01) + (4.014), (II.01) + (4.015), (II.01) + (4.016), (II.01) + (4.017), (II.01) + (4.018), (II.01) + (4.019), (II.01) + (4.020), (II.01) + (4.021), (II.01) + (4.022), (II.01) + (4.023), (II.01) + (4.024), (II.01) + (4.025), (II.01) + (5.001), (II.01) + (5.002), (II.01) + (5.003), (II.01) + (5.004), (II.01) + (5.005), (II.01) + (5.006), (II.01) + (5.007), (II.01) + (5.008), (II.01) + (5.009), (II.01) + (5.010), (II.01) + (5.011),
(II.01) + (5.012), (II.01) + (5.013), (II.01) + (5.014), (II.01) + (5.015), (II.01) + (5.016), (II.01) + (5.017), (II.01) + (5.018), (II.01) + (5.019), (II.01) + (5.020), (II.01) + (5.021), (II.01) + (5.022), (II.01) + (5.023), (II.01) + (6.001), (II.01) + (6.002), (II.01) + (6.003), (II.01) + (6.004), (II.01) + (7.001), (II.01) + (7.002), (II.01) + (7.003), (II.01) + (7.004), (II.01) + (7.005), (II.01) + (7.006), (II.01) + (8.001), (II.01) + (9.001), (II.01) + (9.002), (II.01) + (9.003), (II.01) + (9.004), (II.01) + (9.005), (II.01) + (9.006), (II.01) + (9.007), (II.01) + (9.008), (II.01) + (9.009), (II.01) + (10.001), (II.01) + (10.002), (II.01) + (10.003), (II.01) + (11.001), (II.01) + (11.002), (II.01) + (12.001), (II.01) + (12.002), (II.01) + (12.003), (II.01) + (12.004), (II.01) + (13.001), (II.01) + (13.002), (II.01) + (13.003), (II.01) + (13.004), (II.01) + (13.005), (II.01) + (13.006), (II.01) + (14.001), (II.01) + (14.002), (II.01) + (15.001), (II.01) + (15.002), (II.01) + (15.003), (II.01) + (15.004), (II.01) + (15.005), (II.01) + (15.006), (II.01) + (15.007), (II.01) + (15.008), (II.01) + (15.009), (II.01) + (15.010), (II.01) + (15.011), (II.01) + (15.012), (II.01) + (15.013), (II.01) + (15.014), (II.01) + (15.015), (II.01) + (15.016), (II.01) + (15.017), (II.01) + (15.018), (II.01) + (15.019), (II.01) + (15.020), (II.01) + (15.021), (II.01) + (15.022), (II.01) + (15.023), (II.01) + (15.024), (II.01) + (15.025), (II.01) + (15.026), (II.01) + (15.027), (II.01) + (15.028), (II.01) + (15.029), (II.01) + (15.030), (II.01) + (15.031), (II.01) + (15.032), (II.01) + (15.033), (II.01) + (15.034), (II.01) + (15.035), (II.01) + (15.036), (II.01) + (15.037), (II.01) + (15.038), (II.01) + (15.039), (II.01) + (15.040), (II.01) + (15.041), (II.01) + (15.042), (II.01) + (15.043), (II.01) + (15.044), (II.01) + (15.045), (II.01) + (15.046), (II.01) + (15.047), (II.01) + (15.048), (II.01) + (15.049), (II.01) + (15.050), (II.01) + (15.051), (II.01) + (15.052), (II.01) + (15.053), (II.01) + (15.054), (II.01) + (15.055), (II.01) + (15.056), (II.01) + (15.057), (II.01) + (15.058), (II.01) + (15.059), (II.01) + (15.060), (II.01) + (15.061), (II.01) + (15.062). (II.01) + (15.063). (II.01) + (15.064). (II.01) + (15.065), (II.01) + 15.066), (II.01) + (15.067), (II.01) + (15.068), (II.01) + (15.069), (II.01) + (15.070), (II.01) + (15.071),
(II.01) + (15.072), (II.01) + (15.073), (II.01) + (15.074), (II.01) + (15.075), (II.01) + (15.076), (II.01), (II.01) + (15.077), (II.01) + (15.078), (II.01) + (15.079), (II.01) + (15. 080), (II.01) + (15.081), (II.01) + (15.082), (II.01) + (15.083), (II.01) + (15.084), (II.01) + (15.085), (II.01) + (15.086), (II.01) + (15.087), (II.01) + (15.088), (II.01) + (15.089), (II.01) + (15.090), (II.01) + (15.091), (II.01) + (15.092), (II.01) + (15.093), (II.01) + (15.094), (II.01) + (15.095), (II.01) + (15.096), (II.01) + (15.097), (II.01) + (15.098), (II.01) + (15.099), (II.01) + (15.100), (II.01) + (15.101), (II.01) + (15.102), (II.01) + (15.103), (II.01) + (15.104), (II.01) + (15.105), (II.01) + (15.106), (II.01) + (15.107), (II.01) + (15.108), (II.01) + (15.109), (II.01) + (15.110), (II.01) + (15.111), (II.01) + (15.112). Nessas combinações, o primeiro componente é um composto de fórmula (II) como definido na tabela II.1 (por exemplo, II.01) e o segundo componente é um fungicida escolhido nos grupos 1 a 15 como definido aqui. Por exemplo, a combinação (II.01) + (1.001) corresponde a uma combinação compreendendo composto II.01 na Tabela II.1 e ciproconazol (1.001).
[0089] Em algumas outras modalidades, as combinações de composto correspondem às combinações descritas acima, em que o composto (II.01) é substituído por qualquer um dos compostos citados na Tabela II.1.
[00104] Os compostos de fórmula (II), e o fungicida selecionado dos grupos (1) a (15), podem estar presentes em uma razão em peso variando de 100:1 a 1:100 (composto de fórmula (II) : fungicida selecionado dos grupos (1) a (15)), ou variando de 50:1 a 1:50, ou variando de 20:1 a 1:20. Outros exemplos de intervalos de razão de peso incluem 95:1 to 1:95, 90:1 a 1:90, 85:1 a 1:85, 80:1 a 1:80, 75:1 a 1:75, 70:1 a 1:70, 65:1 a 1:65, 60:1 a 1:60, 55:1 a 1:55, 45:1 a 1:45, 40:1 a 1:40, 35:1 a 1:35, 30:1 a 1:30, 25:1 a 1:25, 15:1 a 1:15, 10:1 a 1:10, 5:1 a 1:5, 4:1 a 1:4, 3:1 a 1:3, 2:1 a 1:2.
[00105] Outro fungicida escolhido nos grupos 1 a 15, como definidos aqui, pode ser adicionado às combinações de compostos.
[00106] O(s) composto(s) e a composição da invenção também podem ser combinados com um ou mais agentes de controle biológico.
[00107] Exemplos de agentes de controle biológico que podem ser combinados com o(s) composto(s) e a composição da invenção são: (A) Agentes antibacterianos selecionados do grupo de: (A1) bactérias, tais como (A1.1) Bacillus subtilis, em particular cepa QST713/AQ713 (disponível como SERENADE OPTI ou SERENADE ASO de Bayer CropScience LP, US, tendo Nº de Acesso NRRL B21661 e descrito na Patente dos EUA Nº. 6.060.051); (A1.2) Bacillus amyloliquefaciens, em particular cepa D747 (disponível como Double Nickel™ de Certis, US, tendo número de acesso FERM BP-8234 e divulgado na Patente dos EUA Nº. 7.094.592); (A1.3) Bacillus pumilus, em particular cepa BU F-33 (tendo Nº de Acesso NRRL 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens cepa FZB24 (disponível como Taegro® de Novozymes, US); (A1.5) a Paenibacillus sp. cepa tendo Nº. de Acesso NRRL B-50972 ou Nº. de Acesso NRRL B-67129 e descrito na Publicação de Patente Internacional Nº. WO 2016/154297; e (A2) fungos, tais como (A2.1) Aureobasidium pullulans, em particular blastosporos de cepa DSM14940; (A2.2) Aureobasidium pullulans blastosporos de cepa DSM 14941; (A2.3) Aureobasidium pullulans, em particular misturas de blastosporos de cepas DSM14940 e DSM14941; (B) Fungicidas selecionados do grupo de: (B1) bactérias, por exemplo, (B1.1) Bacillus subtilis, em particular cepa QST713/AQ713 (disponível como SERENADE OPTI ou SERENADE ASO de Bayer CropScience LP, US, tendo Nº de Acesso NRRL B21661 e descrito na Patente dos EUA Nº. 6.060.051); (B1.2) Bacillus pumilus, em particular cepa QST2808 (disponível como SONATA® de Bayer CropScience LP, US, tendo Nº. de Acesso NRRL B-30087 e descrito na Patente dos EUA Nº. 6.245.551); (B1.3) Bacillus pumilus, em particular cepa GB34 (disponível como Yield Shield® de Bayer AG, DE); (B1.4) Bacillus pumilus, em particular cepa BU F-33 (tendo Nº de Acesso NRRL 50185); (B1.5) Bacillus amyloliquefaciens, em particular cepa D747 (disponível como Double Nickel™ de Certis, US, tendo número de acesso FERM BP-8234 e divulgado na Patente dos EUA Nº. 7.094.592); (B1.6) Bacillus subtilis Y1336 (disponível como BIOBAC® WP de Bion- Tech, Taiwan, registrado como um fungicida biológico em Taiwan sob os Registros Nºs. 4764, 5454, 5096 e 5277); (B1.7) Bacillus amyloliquefaciens cepa MBI 600 (disponível como SUBTILEX from BASF SE); (B1.8) Bacillus subtilis cepa GB03 (disponível como Kodiak® de Bayer AG, DE); (B1.9) Bacillus subtilis var. amyloliquefaciens cepa FZB24 (disponível de Novozymes Biologicals Inc., Salem, Virginia ou Syngenta Crop Protection, LLC, Greensboro, North Carolina como fungicida TAEGRO® ou TAEGRO® ECO (Registro EPA Nº. 70127-5); (B1.10) Bacillus mycoides, isolado J (disponível como BmJ TGAI ou WG de Certis USA); (B1.11) Bacillus licheniformis, em particular cepa SB3086 (disponível como Biofungicida EcoGuard TM e Green Releaf de Novozymes); (B1.12) a Paenibacillus sp. cepa tendo Nº. de Acesso NRRL B-50972 ou Nº. de Acesso NRRL B-67129 e descrito na Publicação de Patente Internacional Nº. WO 2016/154297.
[00108] Em algumas modalidades, o agente de controle biológico é uma cepa de Bacillus subtilis ou Bacillus amyloliquefaciens que produz um composto do tipo fengicina ou plipastatina, um composto do tipo iturina, e/ou um composto do tipo surfactina. Para histórico, ver o seguinte artigo de revisão: Ongena, M., et al., "Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol", Trends in Microbiology, Vol 16, Nº. 3, Março 2008, pp. 115-125. Cepas de Bacillus capazes de produzir lipopeptídeos incluem Bacillus subtilis QST713 (disponível como SERENADE OPTI ou SERENADE ASO de Bayer CropScience LP, US, tendo Nº de Acesso NRRL B21661 e descrito na
Patente dos EUA Nº. 6.060.051), cepa de Bacillus amyloliquefaciens D747 (disponível como Double Nickel™ de Certis, US, tendo número de acesso FERM BP-8234 e divulgado na Patente dos EUA Nº. 7.094.592); Bacillus subtilis MBI600 (disponível como SUBTILEX® de Becker Underwood, US EPA Reg.
Nº. 71840-8); Bacillus subtilis Y1336 (disponível como BIOBAC® WP de Bion-Tech, Taiwan, registrado como um fungicida biológico em Taiwan sob os Registros Nºs. 4764, 5454, 5096 e 5277); Bacillus amyloliquefaciens, em particular cepa FZB42 (disponível como RHIZOVITAL® from ABiTEP, DE); e Bacillus subtilis var. amyloliquefaciens FZB24 (disponível de Novozymes Biologicals Inc., Salem, Virgínia ou Syngenta Crop Protection, LLC, Greensboro, Carolina do Norte como fungicida TAEGRO® ou TAEGRO® ECO (Registro EPA Nº. 70127-5); e (B2) fungos, por exemplo: (B2.1) Coniothyrium minitans, em particular cepa CON/M/91-8 (Nº. de Acesso DSM-9660; por exemplo, Contans ® de Bayer); (B2.2) Metschnikowia fructicola, em particular cepa NRRL Y- 30752 (por exemplo, Shemer®); (B2.3) Microsphaeropsis ochracea (por exemplo, Microx® de Prophyta); (B2.5) Trichoderma spp., incluindo Trichoderma atroviride, cepa SC1 descrito no Pedido Internacional Nº.
PCT/IT2008/000196); (B2.6) Trichoderma harzianum rifai cepa KRL- AG2 (também conhecido como cepa T-22, /ATCC 208479, por exemplo, PLANTSHIELD T-22G, Rootshield®, e TurfShield de BioWorks, US); (B2.14) Gliocladium roseum, cepa 321U de W.F.
Stoneman Company LLC; (B2.35) Talaromyces flavus, cepa V117b; (B2.36) Trichoderma asperellum, cepa ICC 012 de Isagro; (B2.37) Trichoderma asperellum, cepa SKT-1 (por exemplo, ECO-HOPE® de Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, cepa CNCM I-1237 (por exemplo, Esquive® WP de Agrauxine, FR); (B2.39) Trichoderma atroviride, cepa no.
V08/002387; (B2.40) Trichoderma atroviride, cepa NMI nº.
V08/002388; (B2.41) Trichoderma atroviride, cepa NMI no.
V08/002389;
(B2.42) Trichoderma atroviride, cepa NMI nº.
V08/002390; (B2.43) Trichoderma atroviride, cepa LC52 (por exemplo, Tenet de Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, cepa ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, cepa T11 (IMI352941/ CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (por exemplo, Trichodex® de Makhteshim, US); (B2.49) Trichoderma harzianum, em particular, cepa KD (por exemplo, Trichoplus de Biological Control Products, SA (adquirido por Becker Underwood)); (B2.50) Trichoderma harzianum, cepa ITEM 908 (por exemplo, Trianum- P de Koppert); (B2.51) Trichoderma harzianum, cepa TH35 (por exemplo, Root-Pro de Mycontrol); (B2.52) Trichoderma virens (também conhecido como Gliocladium virens), em particular cepa GL-21 (por exemplo, SoilGard 12G de Certis, US); (B2.53) Trichoderma viride, cepa TV1(por exemplo, Trianum-P de Koppert); (B2.54) Ampelomyces quisqualis, em particular cepa AQ 10 (por exemplo, AQ 10® de IntrachemBio Itália); (B2.56) Aureobasidium pullulans, em particular blastosporos de cepa DSM14940; (B2.57) Aureobasidium pullulans, em particular blastosporos de cepa DSM 14941; (B2.58) Aureobasidium pullulans, em particular misturas de blastosporos de cepas DSM14940 e DSM 14941 (por exemplo, Botector® de bio-ferm, CH); (B2.64) Cladosporium cladosporioides, cepa H39 (de Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (Sinônimo: Clonostachys rosea f. catenulate) cepa J1446 (por exemplo, Prestop® de AgBio Inc. e também por exemplo, Primastop® de Kemira Agro Oy); (B2.70) Lecanicillium lecanii (anteriormente conhecido como Verticillium lecanii) conidia de cepa KV01 (por exemplo, Vertalec® de Koppert/Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, cepa WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride, cepa SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride, cepa SKT-2 (FERM P-16511); (B2.77) Trichoderma atroviride, cepa SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride), cepa ICC080 (IMI CC 392151 CABI, por exemplo, BioDerma de AGROBIOSOL DE MEXICO, S.A. DE C.V.); (B2.79) Trichoderma harzianum, cepa DB 103 (por exemplo, T-Gro 7456 de Dagutat Biolab); (B2.80) Trichoderma polysporum, cepa IMI 206039 (por exemplo, Binab TF WP de BINAB Bio-Innovation AB, Suécia); (B2.81) Trichoderma stromaticum (por exemplo, Tricovab de Ceplac, Brazil); (B2.83) Ulocladium oudemansii, em particular cepa HRU3 (por exemplo, Botry-Zen® de Botry-Zen Ltd, NZ); (B2.84) Verticillium albo-atrum (anteriormente V. dahliae), cepa WCS850 (CBS 276.92; por exemplo, Dutch Trig de Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) misturas de Trichoderma asperellum cepa ICC 012 e Trichoderma gamsii cepa ICC 080 (produto conhecido como, por exemplo, BIO-TAMTM de Bayer CropScience LP, US).
[00109] Outros exemplos de agentes de controle biológico que podem ser combinados com o(s) composto(s) e a composição de a invenção são: bactérias selecionadas do grupo que consiste em Bacillus cereus, em particular B. cereus cepa CNCM I-1562 e Bacillus firmus, cepa I-1582 (Nº. de Acesso CNCM I-1582), Bacillus subtilis cepa OST 30002 (Nº. de Acesso NRRL B-50421), Bacillus thuringiensis, em particular B. thuringiensis subespécie israelensis (serótipo H-14), cepa AM65-52 (Nº. de Acesso ATCC 1276), B. thuringiensis subsp. aizawai, em particular cepa ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki cepa HD- 1, B. thuringiensis subsp. tenebrionis cepa NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (nemátodo Rotylenchulus reniformis)-PR3 (Nº. de Acesso ATCC SD-5834), Streptomyces microflavus cepa AQ6121 (= QRD 31.013, NRRL B-50550), e Streptomyces galbus cepa AQ 6047 (Nº. de Acesso NRRL 30232);
fungos e leveduras selecionados do grupo que consiste em Beauveria bassiana, em particular cepa ATCC 74040, Lecanicillium spp., em particular cepa HRO LEC 12, Metarhizium anisopliae, em particular cepa F52 (DSM3884 ou ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), em particular cepa IFPC 200613, ou cepa Apopka 97 (Nº. de Acesso ATCC 20874), e Paecilomyces lilacinus, em particular P. lilacinus cepa 251 (AGAL 89/030550); vírus selecionado do grupo que consiste em vírus de granulose de Adoxophyes orana ("tortrix" de frutas de verão) (GV), vírus de granulose de Cydia pomonella (mariposa-das-maçãs) (GV), vírus de poliedrose nuclear de Helicoverpa armigera (lagarta do algodão) (NPV), mNPV Spodoptera exigua (lagarta-do-cartucho), mNPV de Spodoptera frugiperda (lagarta do cartucho de milho), e NPV de Spodoptera littoralis (curuquerê do algodão africano). bactérias e fungos que pode ser adicionado como "inoculantes" em plantas ou partes de plantas ou órgãos de plantas e que, em virtude de suas propriedades particulares, promovem o crescimento e a saúde das plantas.
Exemplos são: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., em particular Burkholderia cepacia (anteriormente conhecido como Pseudomonas cepacia), Gigaspora spp., ou Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., em particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., e Streptomyces spp. extratos de plantas e produtos formados por microrganismos incluindo proteínas e metabólitos secundários que podem ser utilizados como agentes de controle biológico, tais como Allium sativum, Artemisia absinthium, azadiraquitina, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, quiitina, Armour-Zen,
Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (extrato de saponina de Chenopodium quinoa), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Inseticida Requiem™", rotenona, riania/rianodina, Symphytum officinale, Tanacetum vulgare, timol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, extrato de Brassicaceae, em particular colza em pó ou mostarda em pó.
[00110] Exemplos de inseticidas, acaricidas e nematicidas, respectivamente, que podem ser misturados com o(s) composto(s) e a composição da invenção são:
[00111] (1) inibidores da acetilcolinesterase (AChE), tais como, por exemplo, carbamatos, por exemplo, alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxicarboxim, carbarila, carbofurano, carbossulfano, etiofencarb, fenobucarb, formetanato, furatiocarb, isoprocarb, metiocarb, metomila, metolcarb, oxamila, pirimicarb, propoxur, tiodicarb, tiofanox, triazamato, trimetacarb, XMC e xililcarb; ou organofosfatos, por exemplo, acefato, azametifos, azinfos-etila, azinfos- metila, cadusafos, cloretoxifos, clorfenvinfos, clormefos, clorpirifos- metila, coumafos, cianofos, demeton-S-metila, diazinon, diclorvos/DDVP, dicrotofos, dimetoato, dimetilvinfos, dissulfotona, EPN, etion, etoprofos, famfur, fenamifos, fenitrotion, fention, fostiazato, heptenofos, imiciafos, isofenfos, isopropil O-(metoxiaminotiofosforil) salicilato, isoxation, malation, mecarbam, metamidofos, metidation, mevinfos, monocrotofos, naled, ometoato, oxidemeton-metila, paration- metila, fentoato, forato, fosalona, fosmet, fosfamidon, foxim, pirimifos- metila, profenofos, propetamfos, protiofos, piraclofos, piridafention, quinalfos, sulfotep, tebupirimfos, temefos, terbufos, tetraclorvinfos, tiometon, triazofos, triclorfon e vamidotion.
[00112] (2) Bloqueadores dos canais de cloreto controlados por GABA, tais como, por exemplo, ciclodieno-organoclorinas, por exemplo,
clordano e endossulfano ou fenilpirazóis (fipróis), por exemplo, etiprol e fipronila.
[00113] (3) Moduladores de canal de sódio, tais como, por exemplo, piretroides, por exemplo, acrinatrina, aletrina, d-cis-trans aletrina, d- trans aletrina, bifentrina, bioaletrina, isômero de bioaletrina s- ciclopentenila, bioresmetrina, cicloprotrina, ciflutrina, beta-ciflutrina, cihalotrina, lambda-cihalotrina, gama-cihalotrina, cipermetrina, alfa- cipermetrina, beta-cipermetrina, teta-cipermetrina, zeta-cipermetrina, cifenotrina [(1R)-trans-isômero], deltametrina, empentrina [(EZ)-(1R)- isômero], esfenvalerato, etofenprox, fenpropatrina, fenvalerato, flucitrinato, flumetrina, tau-fluvalinato, halfenprox, imiprotrina, cadetrina, momfluorotrina, permetrina, fenotrina [(1R)-trans-isômero], praletrina, piretrinas (piretro), resmetrina, silafluofeno, teflutrina, tetrametrina, tetrametrina [(1R)-isômero)], tralometrina e transflutrina ou DDT ou metoxiclor.
[00114] (4) Moduladores competitivos do receptor de acetilcolina nicotínico (nAChR), tais como, por exemplo, neonicotinoides, por exemplo, acetamiprida, clotianidina, dinotefurano, imidacloprida, nitenpiram, tiacloprida e tiametoxam ou nicotina ou sulfoxaflor ou flupiradifurona.
[00115] (5) Moduladores alostéricos competitivos do receptor de acetilcolina nicotínico (nAChR), tais como, por exemplo, espinosinas, por exemplo, espinetoram e espinosad.
[00116] (6) Moduladores alostéricos do canal de cloreto controlado por glutamato (GluCl), tais como, por exemplo, avermectinas/milbemicinas, por exemplo, abamectina, benzoato de emamectina, lepimectina e milbemectina.
[00117] (7) Imitadores de hormônio juvenil, tais como, por exemplo, análogos do hormônio juvenil, por exemplo, hidropreno, quinopreno e metopreno ou fenoxicarb ou piriproxifeno.
[00118] (8) Inibidores diversos não específicos (multissítio), tais como, por exemplo, halogenetos de alquila, por exemplo, brometo de metila e outros halogenetos de alquila; ou cloropicrina ou fluoreto de sulfurila ou bórax ou tártaro emético ou geradores de metil isocianato, por exemplo, diazomet e metame.
[00119] (9) Moduladores de órgãos cordotonais, tais como, por exemplo, pimetrozina ou flonicamida.
[00120] (10) Inibidores de crescimento de ácaros, tais como, por exemplo, clofentezina, hexitiazox e diflovidazina ou etoxazol.
[00121] (11) Disruptores microbianos da membrana intestinal de inseto, tais como, por exemplo, Bacillus thuringiensis subespécie israelensis, Bacillus sphaericus, Bacillus thuringiensis subespécie aizawai, Bacillus thuringiensis subespécie kurstaki, Bacillus thuringiensis subespécie tenebrionis, e proteínas de plantas B.t: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.
[00122] (12) Inibidores de ATP sintase mitocondrial, tais como, disruptores de ATP, tais como, por exemplo, compostos de diafentiuron ou organotina, por exemplo, azociclotina, cihexatina e óxido de fenbutatina ou propargita ou tetradifon.
[00123] (13) Desacopladores de fosforilação oxidativa via rompimento do gradiente de prótons, tais como, por exemplo, clorfenapir, DNOC e sulfluramida.
[00124] (14) Bloqueadores dos canais do receptor de acetilcolina nicotínico, tais como, por exemplo, bensultap, cloridrato de cartap, tiocilam, e tiosultap-sódio.
[00125] (15) Inibidores da biossíntese de quitina, tipo 0, tais como, por exemplo, bistriflurona, clorfluazurona, diflubenzurona, flucicloxurona, flufenoxurona, hexaflumurona, lufenurona, novalurona, noviflumurona, teflubenzurona e triflumurona.
[00126] (16) Inibidores da biossíntese de quitina, tipo 1, por exemplo, buprofezina.
[00127] (17) Disruptor de muda (em particular para Diptera, isto é, dipterans), tais como, por exemplo, ciromazina.
[00128] (18) Agonistas do receptor de ecdisona, tais como, por exemplo, cromafenozida, halofenozida, metoxifenozida e tebufenozida.
[00129] (19) Agonistas do receptor de octopamina, tais como, por exemplo, amitraz.
[00130] (20) Inibidores do transporte de elétrons do complexo mitocondrial III, tais como, por exemplo, hidrametilnona ou acequinocila ou fluacripirima.
[00131] (21) Inibidores do transporte de elétrons do complexo mitocondrial I, tais como, por exemplo, do grupo de acaricidas METI, por exemplo, fenazaquina, fenpiroximato, pirimidifeno, piridabeno, tebufenpirad e tolfenpirad ou rotenona (Derris).
[00132] (22) Bloqueadores de canais de sódio dependentes de tensão, tais como, por exemplo, indoxacarb ou metaflumizona.
[00133] (23) Inibidores de acetil CoA carboxilase, tais como, por exemplo, derivados do ácido tetrônico e tetrâmico, por exemplo, espirodiclofeno, espiromesifeno e espirotetramat.
[00134] (24) Inibidores do transporte de elétrons do complexo mitocondrial IV, tais como, por exemplo, fosfinas, por exemplo, fosfeto de alumínio, fosfeto de cálcio, fosfina e fosfeto de zinco ou cianetos, por exemplo, cianeto de cálcio, cianeto de potássio e cianeto de sódio.
[00135] (25) Inibidores do transporte de elétrons do complexo mitocondrial II, tais como, por exemplo, derivados de beta-cetonitrila, por exemplo, cienopirafeno e ciflumetofeno e carboxanilidas, tais como, por exemplo, piflubumida.
[00136] (28) Moduladores do receptor de Rianodina, tais como, por exemplo, diamidas, por exemplo, clorantraniliprol, ciantraniliprol e flubendiamida, outros compostos ativos, tais como, por exemplo, Afidopiropeno, Afoxolaner, Azadiraquitina, Benclotiaz, Benzoximato, Bifenazato, Broflanilida, Bromopropilato, Quinometionat, Cloropraletrina, Criolita, Ciclaniliprol, Cicloxaprida, Cihalodiamida, Dicloromezotiaz, Dicofol, epsílon-Metoflutrina, epsílon-Momflutrina, Flometoquina, Fluazaindolizina, Fluensulfona, Flufenerim, Flufenoxistrobina, Flufiprol, Fluhexafona, Fluopiram, Fluralaner, Fluxametamida, Fufenozida, Guadipir, Heptaflutrina, Imidaclotiz, Iprodiona, kapa-Bifentrina, kapa- Teflutrina, Lotilaner, Meperflutrina, Paichongding, Piridalil, Pirifluquinazona, Piriminostrobina, Espirobudiclofeno, Tetrametilflutrina, Tetraniliprol, Tetraclorantraniliprol, Tigolaner, Tioxazafeno, Tiofluoximato, Triflumezopirim e iodometano; outras preparações baseadas em Bacillus firmus (I-1582, BioNeem, Votivo), e também os seguintes compostos compostos: 1-{2-fluoro-4-metil-5-[(2,2,2- trifluoroetil)sulfinil]fenil}-3-(trifluorometil)-1H-1,2,4-triazol-5-amina (conhecido de WO2006/043635) (CAS 885026-50-6), {1’-[(2E)-3-(4- clorofenil)prop-2-en-1-il]-5-fluorospiro[indol-3,4’-piperidin]-1(2H)-il}(2- cloropiridin-4-il)metanona (conhecido de WO2003/106457) (CAS 637360-23-7), 2-cloro-N-[2-{1-[(2E)-3-(4-clorofenil)prop-2-en-1- il]piperidin-4-il}-4-(trifluorometil)fenil]isonicotinamida (conhecido de WO2006/003494) (CAS 872999-66-1), 3-(4-cloro-2,6-dimetilfenil)-4- hidroxi-8-metoxi-1,8-diazaspiro[4.5]dec-3-en-2-ona (conhecido de WO 2010052161) (CAS 1225292-17-0), 3-(4-cloro-2,6-dimetilfenil)-8- metoxi-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-il etil carbonato (conhecido de EP2647626) (CAS 1440516-42-6), 4-(but-2-in-1-iloxi)-6-(3,5- dimetilpiperidin-1-il)-5-fluoropirimidina (conhecido de WO2004/099160) (CAS 792914-58-0), PF1364 (conhecido de JP2010/018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-cloropiridin-3-il)metil]piridin-2(1H)-ilideno]- 2,2,2-trifluoroacetamida (conhecido de WO2012/029672) (CAS
1363400-41-2), (3E)-3-[1-[(6-cloro-3-piridil)metil]-2-piridilideno]-1,1,1- trifluoro-propan-2-ona (conhecido de WO2013/144213) (CAS 1461743- 15-6),, N-[3-(benzilcarbamoil)-4-clorofenil]-1-metil-3-(pentafluoroetil)-4- (trifluorometil)-1H-pirazol-5-carboxamida (conhecido de WO2010/051926) (CAS 1226889-14-0), 5-bromo-4-cloro-N-[4-cloro-2- metil-6-(metilcarbamoil)fenil]-2-(3-cloro-2-piridil)pirazol-3-carboxamida (conhecido de CN103232431) (CAS 1449220-44-3), 4-[5-(3,5- diclorofenil)-4,5-dihidro-5-(trifluorometil)-3-isoxazolil]-2-metil-N-(cis-1- oxido-3-tietanil)-benzamida, 4-[5-(3,5-diclorofenil)-4,5-dihidro-5- (trifluorometil)-3-isoxazolil]-2-metil-N-(trans-1-oxido-3-tietanil)- benzamida e 4-[(5S)-5-(3,5-diclorofenil)-4,5-dihidro-5-(trifluorometil)-3- isoxazolil]-2-metil-N-(cis-1-oxido-3-tietanil)benzamida (conhecido de WO 2013/050317 A1) (CAS 1332628-83-7), N-[3-cloro-1-(3-piridinil)- 1H-pirazol-4-il]-N-etil-3-[(3,3,3-trifluoropropil)sulfinil]-propanamida, (+)- N-[3-cloro-1-(3-piridinil)-1H-pirazol-4-iyl]-N-etil-3-[(3,3,3- trifluoropropil)sulfinil]-propanamida e (-)-N-[3-cloro-1-(3-piridinil)-1H- pirazol-4-il]-N-etil-3-[(3,3,3-trifluoropropil)sulfinil]-propanamida (conhecido de WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-cloro-2-propen- 1-il]amino]-1-[2,6-dicloro-4-(trifluorometil)fenil]-4-[(trifluorometil)sulfinil]- 1H-pirazol-3-carbonitrila (conhecido de CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-cloro-2-metil-6- [(metilamino)tioxometil]fenil]-1-(3-cloro-2-piridinil)-1H-pirazol-5- carboxamida, (Liudaibenjiaxuanan, conhecido de CN 103109816 A) (CAS 1232543-85-9); N-[4-cloro-2-[[(1,1-dimetiletil)amino]carbonil]-6- metilfenil]-1-(3-cloro-2-piridinil)-3-(fluorometoxi)-1H-Pirazol-5- carboxamida (conhecido de WO 2012/034403 A1) (CAS 1268277-22- 0), N-[2-(5-amino-1,3,4-tiadiazol-2-il)-4-cloro-6-metilfenil]-3-bromo-1-(3- cloro-2-piridinil)-1H-pirazol-5-carboxamida (conhecido de WO 2011/085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dicloro-4-[(3,3-dicloro-
2-propen-1-il)oxi]fenoxi]propoxi]-2-metoxi-6-(trifluorometil)-pirimidina (conhecido de CN 101337940 A) (CAS 1108184-52-6); (2E)- e 2(Z)-2- [2-(4-cianofenil)-1-[3-(trifluorometil)fenil]etilideno]-N-[4- (difluorometoxi)fenil]-hidrazinacarboxamida (conhecido de CN 101715774 A) (CAS 1232543-85-9); éster de ácido 3-(2,2- dicloroetenil)-2,2-dimetil-4-(1H-benzimidazol-2-il)fenil- ciclopropanocarboxílico (conhecido de CN 103524422 A) (CAS 1542271-46-4); metil éster de ácido (4aS)-7-cloro-2,5-dihidro-2- [[(metoxicarbonil)[4-[(trifluorometil)tio]fenil]amino]carbonil]-indeno[1,2- e][1,3,4]oxadiazina-4a(3H)-carboxílico (conhecido de CN 102391261 A) (CAS 1370358-69-2); 6-deoxi-3-O-etil-2,4-di-O-metil-, 1-[N-[4-[1-[4- (1,1,2,2,2-pentafluoroetoxi)fenil]-1H-1,2,4-triazol-3-il]fenil]carbamato]-α- L-manopiranose (conhecido de US 2014/0275503 A1) (CAS 1181213- 14-8); 8-(2-ciclopropilmetoxi-4-trifluorometil-fenoxi)-3-(6-trifluorometil- piridazin-3-il)-3-aza-biciclo[3.2.1]octano (CAS 1253850-56-4), (8-anti)- 8-(2-ciclopropilmetoxi-4-trifluorometil-fenoxi)-3-(6-trifluorometil- piridazin-3-il)-3-aza-biciclo[3.2.1]octano (CAS 933798-27-7), (8-syn)-8- (2-ciclopropilmetoxi-4-trifluorometil-fenoxi)-3-(6-trifluorometil-piridazin- 3-il)-3-aza-biciclo[3.2.1]octano (conhecido de WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-cloro-1-(3-piridinil)-1H- pirazol-4-il]-N-etil-3-[(3,3,3-trifluoropropil)tio]-propanamida (conhecido de WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) e N-[4-(aminotioxometil)-2-metil-6-[(metilamino)carbonil]fenil]-3-bromo-1- (3-cloro-2-piridinil)-1H-pirazol-5-carboxamida (conhecido de CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-il)-4-[[4- (trifluorometil)fenil]metoxi]-pirimidina (conhecido de WO 2013/115391 A1) (CAS 1449021-97-9), 3-(4-cloro-2,6-dimetilfenil)-4-hidroxi-8-metoxi- 1-metil-1,8-diazaspiro[4.5]dec-3-en-2-ona (conhecido de WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0), 3-(4- cloro-2,6-dimetilfenil)-8-metoxi-1-metil-1,8-diazaspiro[4.5]decano-2,4-
diona (conhecido de WO 2014/187846 A1) (CAS 1638765-58-8), etil éster de ácido 3-(4-cloro-2,6-dimetilfenil)-8-metoxi-1-metil-2-oxo-1,8- diazaspiro[4.5]dec-3-en-4-il-carbônico (conhecido de WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-cloro-3- piridinil)metil]-2(1H)-piridinilideno]-2,2,2-trifluoro-acetamida (conhecido de DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]- N-[1-[(6-cloro-3-piridinil)metil]-2(1H)-piridinilideno]-2,2,2-trifluoro- acetamida, (conhecido de WO 2016005276 A1) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-cloro-3-piridinil)metil]-2(1H)-piridinilideno]-2,2,2-trifluoro- acetamida, (CAS 1702305-40-5), 3-endo-3-[2-propoxi-4- (trifluorometil)fenoxi]-9-[[5-(trifluorometil)-2-piridinil]oxi]-9- azabiciclo[3.3.1]nonano (conhecido de WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).
[00137] Exemplos de agentes de proteção que podem ser misturados com o(s) composto(s) e a composição da invenção são, por exemplo, benoxacor, cloquintocet (-mexila), ciometrinila, ciprossulfamida, diclormida, fenclorazol (-etila), fenclorim, flurazol, fluxofenim, furilazol, isoxadifeno (-etila), mefenpir (-dietila), anidrido naftálico, oxabetrinila, 2-metoxi-N-({4-[(metilcarbamoil)amino]fenil}- sulfonil)benzamida (CAS 129531-12-0), 4-(dicloroacetil)-1-oxa-4- azaspiro[4.5]decano (CAS 71526-07-3), 2,2,5-trimetil-3-(dicloroacetil)- 1,3-oxazolidina (CAS 52836-31-4).
[00138] Exemplos de herbicidas que podem ser misturados com o(s) composto(s) e a composição da invenção são: Acetoclor, acifluorfeno, acifluorfeno-sódio, aclonifeno, alaclor, alidoclor, aloxidim, aloxidim-sódio, ametrina, amicarbazona, amidoclor, amidossulfurona, ácido 4-amino-3-cloro-6-(4-cloro-2-fluoro-3-metilfenil)- 5-fluoropiridina-2-carboxílico, aminociclopiraclor, aminociclopiraclor- potássio, aminociclopiraclor-metila, aminopiralida, amitrol, amônio- sulfamato, anilofos, asulam, atrazina, azafenidina, azimsulfurona,
beflubutamida, benazolina, benazolina-etila, benfluralina, benfuresato, bensulfurona, bensulfurona-metila, bensulida, bentazona, benzobiciclona, benzofenap, biciclopirona, bifenox, bilanafos, bilanafos- sódio, bispiribac, bispiribac-sódio, bromacila, bromobutida, bromofenoxima, bromoxinila, bromoxinil-butirato, -potássio, - heptanoato, e -octanoato, busoxinona, butaclor, butafenacila, butamifos, butenaclor, butralina, butroxidim, butilato, cafenstrol, carbetamida, carfentrazona, carfentrazona-etila, clorambeno, clorbromurona, clorfenac, clorfenac-sódio, clorfenprop, clorflurenol, clorflurenol-metila, cloridazona, clorimurona, clorimurona-etila, clorofthalim, clorotolurona, clortal-dimetila, clorsulfurona, cinidona, cinidona-etila, cinmetilina, cinossulfurona, clacifos, cletodim, clodinafop, clodinafop-propargila, clomazona, clomeprop, clopiralida, cloransulam, cloransulam-metila, cumiluron, cianamida, cianazina, cicloato, ciclopirimorato, ciclossulfamurona, cicloxidim, cihalofop, cihalofop-butila, ciprazina, 2,4- D, 2,4-D-butotila, -butila, -dimetilamônio, -diolamina, -etila, -2- etilhexila, -isobutila, -isooctila, -isopropilamônio, -potássio, - triisopropanolamônio, e -trolamina, 2,4-DB, 2,4-DB-butila, -dimetil- amônio, -isooctila, -potássio, e -sódio, daimurona (dimron), dalapon, dazomet, n-decanol, desmedifam, detosil-pirazolato (DTP), dicamba, diclobenila, 2-(2,4-diclorobenzil)-4,4-dimetil-1,2-oxazolidin-3-ona, 2- (2,5-diclorobenzil)-4,4-dimetil-1,2-oxazolidin-3-ona, diclorprop, diclorprop-P, diclofop, diclofop-metila, diclofop-P-metila, diclosulam, difenzoquat, diflufenican, diflufenzopir, diflufenzopir-sódio, dimefurona, dimepiperato, dimetaclor, dimetametrina, dimetenamida, dimetenamida- P, dimetrasulfurona, dinitramina, dinoterb, difenamida, diquat, diquat- dibromida, ditiopir, diurona, DNOC, endotal, EPTC, esprocarb, etalfluralina, etametsulfurona, etametsulfurona-metila, etiozina, etofumesato, etoxifeno, etoxifeno-etila, etoxissulfurona, etobenzanida, F-9600, F-5231, isto é, N-{2-cloro-4-fluoro-5-[4-(3-fluoropropil)-5-oxo-
4,5-dihidro-1H-tetrazol-1-il]fenil}etanossulfonamida, F-7967, isto é, 3-[7- cloro-5-fluoro-2-(trifluorometil)-1H-benzimidazol-4-il]-1-metil-6- (trifluorometil)pirimidina-2,4(1H,3H)-diona, fenoxaprop, fenoxaprop-P, fenoxaprop-etila, fenoxaprop-P-etila, fenoxassulfona, fenquinotriona, fentrazamida, flamprop, flamprop-M-isopropila, flamprop-M-metila, flazassulfurona, florasulam, fluazifop, fluazifop-P, fluazifop-butila, fluazifop-P-butila, flucarbazona, flucarbazona-sódio, flucetossulfurona, flucloralina, flufenacet, flufenpir, flufenpir-etila, flumetsulam, flumiclorac, flumiclorac-pentila, flumioxazina, fluometuron, flurenol, flurenol-butila, - dimetilamônio e -metila, fluoroglicofeno, fluoroglicofeno-etila, flupropanato, flupirsulfurona, flupirsulfurona-metil-sódio, fluridona, flurocloridona, fluroxipir, fluroxipir-meptila, flurtamona, flutiacet, flutiacet- metila, fomesafeno, fomesafeno-sódio, foramsulfurona, fosamina, glufosinato, glufosinato-amônio, glufosinato-P-sódio, glufosinato-P- amônio, glufosinato-P-sódio, glifosato, glifosato-amônio, -isopropil- amônio, -diamônio, -dimetilamônio, -potássio, -sódio, e -trimésio, H- 9201, isto é, O-(2,4-dimetil-6-nitrofenil) O-etil isopropilfosforamidotioato, halauxifeno, halauxifeno-metila, halosafeno, halossulfurona, halossulfurona-metila, haloxifop, haloxifop-P, haloxifop-etoxietila, haloxifop-P-etoxietila, haloxifop-metila, haloxifop-P-metila, hexazinona, HW-02, isto é, 1-(dimetoxifosforil) etil-(2,4-diclorofenoxi)acetato, imazametabenz, imazametabenz-metila, imazamox, imazamox-amônio, imazapic, imazapic-amônio, imazapir, imazapir-isopropilamônio, imazaquina, imazaquina-amônio, imazetapir, imazetapyr-imônio, imazossulfurona, indanofano, indaziflam, iodossulfurona, iodossulfurona-metil-sódio, ioxinila, ioxinil-octanoato, -potássio e -sódio, ipfencarbazona, isoproturona, isourona, isoxabeno, isoxaflutol, carbutilato, KUH-043, isto é, 3-({[5-(difluorometil)-1-metil-3- (trifluorometil)-1H-pirazol-4-il]metil}sulfonil)-5,5-dimetil-4,5-dihidro-1,2- oxazol, cetospiradox, lactofeno, lenacila, linuron, MCPA, MCPA-butotila,
-dimetilamônio, -2-etilhexila, -isopropilamônio, -potássio, e -sódio, MCPB, MCPB-metila, -etila e -sódio, mecoprop, mecoprop-sódio, e - butotila, mecoprop-P, mecoprop-P-butotila, -dimetilamônio, -2-etilhexila, e -potássio, mefenacet, mefluidida, mesossulfurona, mesossulfurona- metila, mesotriona, metabenztiazurona, metam, metamifop, metamitron, metazaclor, metazossulfurona, metabenztiazurona, metiopirsulfurona, metiozolina, metil isotiocianato, metobromurona, metolaclor, S-metola- clor, metosulam, metoxuron, metribuzina, metsulfurona, metsulfuron- metila, molinat, monolinurona, monossulfurona, monossulfurona-éster, MT-5950, isto é, N-(3-cloro-4-isopropilfenil)-2-metilpentanamida, NGGC-011, napropamida, NC-310, isto é, [5-(benziloxi)-1-metil-1H- pirazol-4-il](2,4-diclorofenil)metanona, neburona, nicosulfurona, ácido nonanoico (ácido pelargônico), norflurazona, ácido oleico (ácidos graxos), orbencarb, ortossulfamurona, orizalina, oxadiargila, oxadiazona, oxassulfurona, oxaziclomefona, oxifluorfeno, paraquat, dicloreto de paraquat, pebulato, pendimetalins, penoxsulam, pentaclorofenol, pentoxazona, petoxamida, óleos de petróleo, fenmedifam, picloram, picolinafeno, pinoxadeno, piperofos, pretilaclor, primissulfurona, primissulfurona-metila, prodiamina, profoxidim, prometon, prometrina, propaclor, propanila, propaquizafop, propazina, profam, propisoclor, propóxicarbazona, propoxicarbazona-sódio, propirissulfurona, propizamida, prosulfocarb, prossulfurona, piraclonila, piraflufeno, piraflufeno-etila, pirasulfotol, pirazolinato (pirazolato), pirazossulfurona, pirazossulfurona-etila, pirazoxifeno, piribambenz, piribambenz-isopropila, piribambenz-propila, piribenzoxim, piributicarb, piridafol, piridato, piriftalid, piriminobac, piriminobac-metila, pirimissulfano, pyritiobac, piritiobac-sódio, piroxassulfona, ipiroxsulam, quinclorac, quinmerac, quinoclamina, quizalofop, quizalofop-etila, quizalofop-P, quizalofop-P-etila, quizalofop-P-tefurila, rimsulfurona, saflufenacila, setoxidim, siduron, simazina, simetrina, SL-261,
sulcotriona, sulfentrazona, sulfometurona, sulfometurona-metila, sulfossulfurona, SYN-523, SYP-249, isto é, 1-etoxi-3-metil-1-oxobut-3- en-2-il 5-[2-cloro-4-(trifluorometil)fenoxi]-2-nitrobenzoato, SYP-300, isto é, 1-[7-fluoro-3-oxo-4-(prop-2-in-1-il)-3,4-dihidro-2H-1,4-benzoxazin-6- il]-3-propil-2-tioxoimidazolidina-4,5-diona, 2,3,6-TBA, TCA (ácido tricloroacético), TCA-sódio, tebutiurona, tefuriltriona, tembotriona, tepraloxidim, terbacila, terbucarb, terbumetona, terbutilazina, terbutrina, tenilclor, tiazopir, tiencarbazona, tiencarbazona-metila, tifensulfurona, tifensulfurona-metila, tiobencarb, tiafenacila, tolpiralato, topramezona, tralcoxidim, triafamona, tri-alato, triasulfurona, triaziflam, tribenurona, tribenurona-metila, triclopir, trietazina, trifloxissulfurona, trifloxissulfurona-sódio, trifludimoxazina, trifluralina, triflussulfurona, triflussulfurona-metila, tritossulfurona, sulfato de ureia, vernolato, XDE- 848, ZJ-0862, isto é, 3,4-dicloro-N-{2-[(4,6-dimetoxipirimidin-2- il)oxi]benzil}anilina, e os seguintes compostos:
[00139] Exemplos reguladores de crescimento de plantas são: Acibenzolar, acibenzolar-S-metila, ácido 5-aminolevulínico, ancimidol, 6-benzilaminopurina, Brassinolida, catequina, cloreto de clormequat, cloprop, ciclanilida, ácido3-(cicloprop-1-enil) propiônico, daminozida,
dazomet, n-decanol, dikegulac, dikegulac-sódio, endotal, endotal- dipotássio, -dissódio, e -mono(N,N-dimetilalquilamônio), etefona, flumetralina, flurenol, flurenol-butila, flurprimidol, forclorfenurona, ácido giberélico, inabenfida, ácido indol-3-acético (IAA), ácido 4-indol-3-il- butírico, isoprotiolano, probenazol, ácido jasmônico, hidrazida maleica, cloreto de mepiquat, 1-metilciclopropeno, jasmonato de metila, 2-(1- naftil)acetamida, ácido1-naftilacético, ácido 2-naftiloxiacético, nitrofenolato-mistura, paclobutrazol, N-(2-feniletil)-beta-alanina, ácido N-fenilftalâmico, prohexadiona, prohexadiona-cálcio, prohidrojasmona, ácido salicílico, estrigolactona, tecnazeno, tidiazurona, triacontanol, trinexapac, trinexapac-etila, tsitodef, uniconazol, uniconazol-P. Métodos e Usos
[00140] O(s) composto (s) e a composição da invenção têm um potente potencial de modulação da defesa das plantas. Podem ser usados para controlar bactérias indesejadas, em particular, bactérias do gênero Xanthomonas. O(s) composto(s) e a composição da invenção podem ser usados para proteger sementes, sementes em germinação, mudas emergidas, plantas, partes de plantas, frutas, produtos de colheita e/ou o solo em que as plantas crescem.
[00141] Controle ou controlar, como usado neste documento, engloba o tratamento preventivo, protetor, curativo e erradicante de microrganismos indesejados.
[00142] Assim, a presente invenção refere-se a um método para controlar doenças bacterianas causadas por bactérias do gênero Xanthomonas compreendendo uma etapa de aplicar pelo menos um composto da invenção ou pelo menos uma composição da invenção às plantas, partes de plantas, sementes, frutos ou ao solo em que as plantas crescem.
[00143] Tipicamente, quando o(s) composto(s) e a composição da invenção são usados em métodos curativos ou de proteção para controlar doenças bacterianas, uma quantidade eficaz e compatível com as plantas é aplicada às plantas, partes de plantas, frutos, sementes ou solo ou substratos em que as plantas crescem. Os substratos adequados que podem ser usados para o cultivo de plantas incluem substratos de base inorgânica, tais como lã mineral, em particular, lã de pedra, perlite, areia ou cascalho; substratos orgânicos, tais como turfa, casca de pinheiro ou serradura; e substratos à base de petróleo, tais como espumas poliméricas ou esferas de plástico. Por quantidade eficaz e compatível com as plantas, entende-se uma quantidade que é suficiente para controlar as bactérias presentes ou passíveis de aparecer na área de cultivo e que não acarrete nenhum sintoma apreciável de fitotoxicidade para as referidas culturas. Tal quantidade pode variar dentro de uma ampla faixa dependendo dos patógenos a serem controlados, o tipo de cultura, o estágio de crescimento da cultura, as condições climáticas e o(s) respectivo(s) composto(s) ou composição da invenção utilizada. Essa quantidade pode ser determinada por testes de campo sistemáticos que estão dentro das capacidades de uma pessoa versada na técnica. Doenças causadas por patógenos bacterianos, por exemplo, espécies de Xanthomonas (por exemplo, Xanthomonas campestris pv. Oryzae), espécies de Pseudomonas (por exemplo, Pseudomonas syringae pv. Lachrymans), espécies de Erwinia (por exemplo, Erwinia amylovora) podem ser controladas pelos compostos da presente invenção. Os compostos de fórmula (II) também podem ser eficientes para controlar fungos fitopatogênicos em plantas. Plantas e Partes de Plantas
[00144] O(s) composto(s) e a composição da invenção podem ser aplicados a quaisquer plantas ou partes de plantas.
[00145] Plantas significam todas as plantas e populações de plantas, tais como plantas silvestres indesejadas ou plantas cultivadas (incluindo plantas cultivadas de ocorrência natural). As plantas cultivadas podem ser plantas que podem ser obtidas por métodos convencionais de melhoramento e otimização ou por métodos biotecnológicos e de engenharia genética ou combinações desses métodos, incluindo as plantas geneticamente modificadas (GMO ou plantas transgênicas) e as cultivares de plantas que são protegíveis e não protegíveis pelos direitos dos melhoradores de plantas. Plantas Geneticamente Modificadas (OGM)
[00146] Plantas geneticamente modificadas (GMO ou plantas transgênicas) são plantas em que um gene heterólogo foi integrado de forma estável ao genoma. A expressão "gene heterólogo" significa essencialmente um gene que é fornecido ou montado fora da planta e quando introduzido no genoma nuclear, cloroplástico ou mitocondrial. Esse gene dá à planta transformada novas ou melhoradas propriedades agronômicas ou outras propriedades ao expressar uma proteína ou polipeptídeo de interesse ou por regulação negativa ou silenciamento de outro(s) gene(s) que está(ão) presente(s) na planta (usando, por exemplo, tecnologia antissentido, tecnologia de cossupressão, tecnologia de interferência de RNA - RNAi - ou tecnologia de microRNA - miRNA). Um gene heterólogo que está localizado no genoma é também chamado de transgene. Um transgene que é definido por sua localização particular no genoma da planta é chamado de evento transgênico ou de transformação.
[00147] Por cultivares de plantas, entende-se plantas que apresentam novas propriedades ("traços") e foram obtidas por melhoramento convencional, por mutagênese ou por técnicas de DNA recombinante. Elas podem ser cultivares, variedades, bio- ou genótipos.
[00148] Por partes da planta, entende-se todas as partes e órgãos das plantas acima e abaixo do solo, tais como brotos, folhas, agulhas, talos, caules, flores, corpos frutíferos, frutos, sementes, raízes,
tubérculos e rizomas. As partes da planta também incluem material colhido e material de propagação vegetativa e generativa, por exemplo, estacas, tubérculos, rizomas, mudas e sementes.
[00149] As plantas que podem ser tratadas de acordo com os métodos da invenção incluem as seguintes: algodão, linho, videira, frutas, vegetais, tais como Rosaceae sp. (por exemplo, frutas pome, tais como maçãs e peras, mas também frutas de caroço, tais como damascos, cerejas, amêndoas e pêssegos, e frutas macias, tais como morangos), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (por exemplo, plantações e árvores de banana), Rubiaceae sp. (por exemplo, café), Theaceae sp., Sterculiceae sp., Rutaceae sp. (por exemplo, limões, laranjas e torajas); Solanaceae sp. (por exemplo, tomates), Liliaceae sp., Asteraceae sp. (por exemplo, alface), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (por exemplo, pepino), Alliaceae sp. (por exemplo, alho- poró cebola), Papilionaceae sp. (por exemplo, ervilhas); plantas de cultura maiores, tais como Gramineae sp. (por exemplo, milho, turfa, cereais como trigo, centeio, arroz, cevada, aveia, painço e triticale), Asteraceae sp. (por exemplo, girassol), Brassicaceae sp. (por exemplo, repolho branco, repolho roxo, brócolis, couve-flor, couve de Bruxelas, pak choi, couve- rábano, rabanetes, colza, mostarda, raiz-forte e agrião), Fabacae sp. (por exemplo, feijão, amendoim), Papilionaceae sp. (por exemplo, soja), Solanaceae sp. (por exemplo, batatas), Chenopodiaceae sp. (por exemplo, beterraba sacarina, beterraba forrageira, acelga suíça, beterraba); plantas úteis e ornamentais para jardins e bosques; e variedades geneticamente modificadas de cada uma dessas plantas.
[00150] Plantas e cultivares de plantas que podem ser tratados pelos métodos divulgados acima incluem plantas e cultivares de plantas que são resistentes a um ou mais estresses bióticos, isto é, as referidas plantas apresentam uma melhor defesa contra pragas animais e microbianas, tais como contra nematoides, insetos, ácaros, fungos fitopatogênicos, bactérias, vírus e/ou viroides.
[00151] Plantas e cultivares de plantas que podem ser tratadas pelos métodos divulgados acima incluem aquelas plantas que são resistentes a um ou mais estresses abióticos. As condições de estresse abiótico podem incluir, por exemplo, seca, exposição à temperatura fria, exposição ao calor, estresse osmótico, inundações, aumento da salinidade do solo, aumento da exposição a minerais, exposição ao ozônio, alta exposição à luz, disponibilidade limitada de nutrientes de nitrogênio, disponibilidade limitada de nutrientes de fósforo, evasão de sombra.
[00152] Plantas e cultivares de plantas que podem ser tratadas pelos métodos divulgados acima incluem aquelas plantas caracterizadas por características de rendimento melhoradas. O aumento do rendimento nas referidas plantas pode ser o resultado de, por exemplo, melhor fisiologia, crescimento e desenvolvimento da planta, tal como eficiência de uso de água, eficiência de retenção de água, melhor uso de nitrogênio, melhor assimilação de carbono, melhor fotossíntese, maior eficiência de germinação e maturação acelerada. A produção pode, além disso, ser afetada pela arquitetura de planta melhorada (sob condições de estresse e sem estresse), incluindo, mas sem limitação, floração precoce, controle de floração para produção de sementes híbridas, vigor de mudas, tamanho da planta, número de entrenós e distância, crescimento da raiz, tamanho da semente, tamanho do fruto, tamanho da vagem, número de vagem ou espiga, número de semente por vagem ou espiga, massa da semente, enchimento melhorado de semente, dispersão reduzida de sementes, redução da deiscência da vagem e resistência ao alojamento. Outros traços de rendimento incluem composição da semente, tal como teor de carboidrato e composição, por exemplo, algodão ou amido, teor de proteína, teor e composição de óleo, valor nutricional, redução de compostos antinutricionais, processabilidade aprimorada e melhor estabilidade de armazenamento.
[00153] Plantas e cultivares de plantas que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas que são plantas híbridas que já expressam a característica de heterose ou vigor híbrido que resulta geralmente em maior rendimento, vigor, saúde e resistência a estresses bióticos e abióticos.
[00154] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima, incluem plantas e cultivares de plantas que são plantas tolerantes a herbicidas, isto é, plantas tornadas tolerantes a um ou mais dados herbicidas. Essas plantas podem ser obtidas por transformação genética ou por seleção de plantas contendo uma mutação que confere tal tolerância ao herbicida.
[00155] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tal como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas que são plantas transgênicas resistentes a insetos, isto é, plantas tornadas resistentes ao ataque de certos insetos alvo. Essas plantas podem ser obtidas por transformação genética ou pela seleção de plantas contendo uma mutação que confere resistência a insetos.
[00156] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas que são plantas transgênicas resistentes a doenças, isto é, plantas tornadas resistentes ao ataque de certos insetos alvo. Essas plantas podem ser obtidas por transformação genética, ou pela seleção de plantas contendo uma mutação que confere resistência a insetos.
[00157] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas que são tolerantes a estresses abióticos. Essas plantas podem ser obtidas por transformação genética, ou pela seleção de plantas contendo uma mutação que confere resistência ao estresse.
[00158] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima, incluem plantas e cultivares de plantas que apresentam quantidade, qualidade e/ou estabilidade de armazenamento alteradas do produto colhido e/ou propriedades alteradas de ingredientes específicos do produto colhido.
[00159] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tal como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas, tais como algodoeiro, com características de fibra alteradas. Essas plantas podem ser obtidas por transformação genética ou por seleção de plantas que contenham uma mutação que confira essas características de fibra alteradas.
[00160] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima, incluem plantas e cultivares de plantas, tal como colza ou plantas Brassica relacionadas, com características de perfil de óleo alteradas. Essas plantas podem ser obtidas por transformação genética ou por seleção de plantas que contêm uma mutação que confere tais características alteradas do perfil de óleo.
[00161] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas, tais como colza ou plantas Brassica relacionadas, com características alteradas de quebra de sementes. Essas plantas podem ser obtidas por transformação genética, ou por seleção de plantas que contenham uma mutação que confira tais características alteradas de quebra de sementes, incluindo plantas como a colza, com quebra de sementes retardada ou reduzida.
[00162] Plantas e cultivares de plantas (obtidas por métodos de biotecnologia vegetal, tais como engenharia genética) que podem ser tratadas pelos métodos divulgados acima incluem plantas e cultivares de plantas, tais como plantas de tabaco, com padrões de modificação de proteína pós-translacional alterados.
[00163] Os aspectos do presente ensinamento podem ser mais bem compreendidos à luz dos exemplos que seguem, que não devem ser interpretados como limitantes ao âmbito do presente ensinamento de forma alguma.
EXEMPLOS Síntese de compostos de fórmula (II) Exemplo de preparação 1: Preparação de N-[(3,4,5-tricloro-2- tienil)carbonil]glicinato de metila (composto II.01)
[00164] A uma solução de 250 mg (1,08 mmol) de ácido 3,4,5- triclorotiofeno-2-carboxílico e 210 mg (1,67 mmol) de cloridrato de etil glicinato (1:1) dissolvido em 4,2 ml de tetrahidrofuran, foi adicionado 0,23 ml (1,62 mmol) de trietilamina seguido por 1,0 ml (1,68 mmol) de uma solução de anidrido propanofosfônico a 50% (p/p) em etil acetato. A mistura de reação foi agitada à temperatura ambiente durante 20 horas. A mistura de reação foi resfriada bruscamente com água e extraída com etil acetato. As camadas orgânicas combinadas foram secas sobre sulfato de magnésio, filtradas e concentradas sob pressão reduzida. O resíduo foi purificado por cromatografia de coluna em sílica gel (gradiente n-heptano/etil acetato) para produzir 178 mg (93% de pureza, 51% de rendimento) de N-[(3,4,5-tricloro-2- tienil)carbonil]glicinato de metilacomo um sólido branco. LogP = 2,8. (M+H) = 302. Exemplo de preparação 2: Preparação de N-[(3,4,5-tricloro-2- tienil)carbonil]glicina (composto II.05)
[00165] A uma solução de 178 mg (0,59 mmol) de N-[(3,4,5-tricloro- 2-tienil)carbonil]glicinato de metiladissolvido em 3 ml de tetrahidrofurano, foi adicionado gota a gota 1,3 ml de uma solução aquosa de hidróxido de lítio 1M (1,3 mmol). A reação foi agitada à temperatura ambiente durante 4 horas. A mistura de reação foi diluída com etil acetato, água e uma solução aquosa saturada de bicarbonato de sódio. A camada orgânica foi lavada duas vezes com uma solução aquosa saturada de bicarbonato de sódio. As camadas aquosas combinadas foram cuidadosamente acidificadas com solução aquosa de ácido clorídrico a 37% (p/p) a 0ºC e extraídas com etil acetato. As camadas orgânicas combinadas foram secas sobre sulfato de magnésio, filtradas e concentradas sob pressão reduzida para produzir 159 mg (98% de pureza, 92% de rendimento) de N-[(3,4,5-tricloro-2- tienil)carbonil]glicina como um sólido branco. LogP = 2,14. (M-H) = 286. Exemplo de preparação 3: Preparação de 1-{[(3,4,5-tricloro-2- tienil)carbonil]amino}ciclopropanocarboxilato de etila (composto II.02) Etapa 1: Preparação de 1-{[(3-amino-4,5-dicloro-2- tienil)carbonil]amino}ciclopropanocarboxilato de etila (composto XVIIc.01)
[00166] A uma solução de 150 mg (0,60 mmol) de cloridrato de ácido 3-amino-4,5-diclorotiofeno-2-carboxílico (1:1) (composto XIXc.01) e 255 mg (1,50 mmol) de cloridrato de etil 1-aminociclopropanocarboxilato (1:1) dissolvido em 4,0 ml de diclorometano, foi adicionado 0,45 ml (2,59 mmoles) de N,N-diisopropiletilamina seguido por uma solução de 255 mg (1,50 mmol) de cloreto de 2-cloro-1,3-dimetilimidazolínio em 2,0 ml de diclorometano. A mistura de reação foi agitada à temperatura ambiente durante 16 horas. A mistura de reação foi resfriada bruscamente com água e extraída com diclorometano. As camadas orgânicas combinadas foram secas sobre sulfato de magnésio, filtradas e concentradas sob pressão reduzida. O resíduo foi purificado por cromatografia líquida de alto desempenho preparativa (gradiente de acetonitrila/solução aquosa de ácido fórmico (1%)) para produzir 69 mg (100% de pureza, 35% de rendimento) de 1-{[(3-amino-4,5-dicloro-2- tienil)carbonil]amino}ciclopropanocarboxilato de etila como um sólido branco. LogP = 2.77. (M+H) = 323. Etapa 2: Preparação de 1-{[(3,4,5-tricloro-2- tienil)carbonil]amino}ciclopropanocarboxilato de etila (composto II.02)
[00167] A uma solução de cloreto de cobre (I) (9,8 mg, 0,10 mmol) em 0,5 ml de acetonitrila anidra, foi adicionado gota a gota nitrito de terc- butil (13 µL, 0,10 mmol) a 0ºC. A mistura de reação foi deixada aquecer até a temperatura ambiente antes da adição gota a gota de uma solução de 25 mg (0,06 mmol) de 1-{[(3-amino-4,5-dicloro-2- tienil)carbonil]amino} ciclopropanocarboxilato de etila em 0,5 ml de acetonitrila anidro. A mistura de reação foi agitada à temperatura ambiente durante 3 horas. A mistura de reação foi diluída com diclorometano e cuidadosamente acidificada com uma solução aquosa de ácido clorídrico 1M. A camada aquosa foi extraída duas vezes com diclorometano. As camadas orgânicas combinadas foram secas sobre sulfato de magnésio, filtradas e concentradas sob pressão reduzida. O resíduo foi purificado por cromatografia líquida de alto desempenho preparativa (gradiente de acetonitrila/solução aquosa de ácido fórmico (1%)) para produzir 12 mg (93% de pureza, 48% de rendimento) de 1- {[(3,4,5-tricloro-2-tienil)carbonil]amino}ciclopropanocarboxilato de etila como um sólido bege. LogP = 3,40. (M) = 341. Compostos Exemplificativos
[00168] Compostos de acordo com a invenção, como mostrado nas tabelas II.1, II.2, II.3, II.4 e II.5, foram preparados em analogia com os exemplos providos acima e/ou de acordo com a descrição geral dos processos aqui divulgados. Os compostos exemplificativos são racêmicos salvo especificado de forma diferente.
[00169] A tabela II.1 a seguir ilustra de maneira não limitante exemplos de compostos de acordo com a fórmula (II).
Tabela II.1: Ex.
N° R1 R2 R3 R4 R5 R6 R7 LogP Enantiômero Rotação Óptica*
II.01 Cl Cl Cl H H Me H 2,83[a] II.02 Cl Cl Cl -CH2-CH2- Et H 3.41[a] II.03 Cl Cl Cl -CH2-CH2- H H 2.06[a] II.04 Cl Cl Cl 2-metilpropila H Et H 5,22[a] II.05 Cl Cl Cl H H H H 2,16[a] II.06 Cl Cl Cl ciclopropila H Me H 3,81[a] II.07 Cl Cl Cl H H 2,2,2-trifluoroetila H 3,60[a]
69/93 II.08 Cl Cl Cl H H fenila H 3,87[a] II.09 Cl Cl Cl H H isopropila H 3,67[a] II.10 Cl Cl Cl H H propila H 3,70[a] II.11 Cl Cl Cl H H butila H 4,18[a] II.12 Cl Cl Cl H H ciclopropila H 3,33[a] II.13 Cl Cl Cl H H benzila H 4,11[a] II.14 Cl Cl Cl butan-2-ila H Me H 4,82[a] (2S,3S) II.15 Cl Cl Cl (4-hidroxifenil)metila H Et H 3,63[a] II.16 Cl Cl Cl H H ciclobutila H 3,87[a] (Z)-hex-3-en-1- II.17 Cl Cl Cl H H H 4,69[a] ila
Ex.
N° R1 R2 R3 R4 R5 R6 R7 LogP Enantiômero Rotação Óptica*
II.18 Cl Cl Cl H H ciclopropilmetila H 3,81[a] II.19 Cl Cl Cl H H 2-metilpropila H 4,13[a] II.20 Cl Cl Cl H H prop-2-in-1-ila H 3,13[a] II.21 Cl Cl Cl H H cianometila H 2,84[a] II.22 Cl Cl Cl H H alila H 3,64[a] II.23 Cl Cl Cl H H trimetilsililmetila H 4,81[a] II.24 Cl Cl Cl H H terc-butila H 4,27[b] +50.5° (c=1,03, II.25 Cl Cl Cl benzila H Et H 5,00[a] (S)
70/93 CDCl3, 25°C) II.26 Cl Cl Cl benzila H Et H 5,04[a] -32° (c=1,13, II.27 Cl Cl Cl 2-metilpropila H Et H 5,20[a] (R) CDCl3, 25°C) +13.8° (c=1,3, II.28 Cl Cl Cl 2-metilpropila H Et H 5,16[a] (S) CDCl3, 25°C) II.29 Cl Cl Cl -CH2-CH2- Me H 3,04[a] II.30 Cl Cl Cl butan-2-ila H H H 3,69[a] (2S,3S) II.31 Cl Cl Cl 2-metilpropila H H H 3,62[a] II.32 Cl Cl Cl benzila H H H 3,56[a] II.33 Cl Cl Cl ciclopropila H H H 2,83[a]
Ex.
N° R1 R2 R3 R4 R5 R6 R7 LogP Enantiômero Rotação Óptica*
II.34 Cl Cl Cl ciclopropila H Et H 4,30[a] II.35 Cl Cl Cl H H Et Me 3,21[a] II.36** Cl Cl Cl -CH2-CH(CH=CH2)- Me H 3,68[a] * -39.6° (c=1,62, II.37 Cl Cl Cl benzila H Et H 5,00[a] (R) CDCl3, 25°C) Nota: Me: metila; Et: etila *Rotação óptica: concentração c é expressa em g/100 ml; ** Mistura de estereoisômeros
71/93
[00170] Intermediários exemplificativos de acordo com a invenção, como mostrado nas tabelas a seguir, foram preparados em analogia com os exemplos providos acima e/ou de acordo com a descrição geral dos processos aqui divulgados.
[00171] A tabela II.2 a seguir ilustra de maneira não limitante um exemplo de intermediários de acordo com a fórmula (XVIa) e (XVIb).
(XVIa) (XVIb) Tabela II.2: Ex N° R1 R2 R3 R4 R5 R6 LogP XVIa.01 - Cl Cl H H Et 2,40[a] XVIa.02 - Cl Cl benzila H Et 3,99[a] XVIa.03 - Cl Cl -CH2-CH2- Et 2,59[a] XVIb.01 Cl - Cl H H Et 2,37[a] XVIb.02 Cl - Cl benzila H Et 3,99[a] XVIb.03 Cl - Cl -CH2-CH2- Et 2,55[a] Nota: Et: etila
[00172] A tabela II.3 a seguir ilustra de maneira não limitante um exemplo de intermediários de acordo com a fórmula (XVIc).
[00173] (XVIc)
Tabela II.3: Ex N° R1 R2 R4 R5 R6 LogP XVIc.01 Cl Cl -CH2-CH2- Me 2,49[a] XVIc.02* Cl Cl -CH2-CH(CH=CH2)- Me 3,06[a] XVIc.03 Cl Cl ciclopropila H Me 2,98[a] XVIc.04 Cl Cl -CH2-CH2- Et 2,77[a] XVIc.05 Cl Cl ciclopropila H H 2,33[a] XVIc.06 Cl Cl -CH2-CH2- H 2,01[a] Nota: Me: metila; Et: etila * Mistura de estereoisômeros
[00174] A tabela II.4 a seguir ilustra de maneira não limitante um exemplo de intermediários de acordo com a fórmula (XVIIc).
(XVIIc)(XVIIIc) Tabela II.4: Ex N° R1 R2 R4 R5 R6 V LogP XVIIc.01 Cl Cl -CH2-CH2- Et 2,77[a] XVIIIc.01 Cl Cl -CH2-CH2- Et terc-butoxicarbonila 3,34[a] Nota: Et: etila
[00175] A tabela II.5 a seguir ilustra de maneira não limitante um exemplo de intermediários de acordo com a fórmula (XIXc).
(XIXc)
Tabela II.5: Ex N° R1 R2 U1a LogP XIXc.01 Cl Cl OH 2,05[a]
[00176] Nas tabelas acima, a medição dos valores de LogP foi realizada de acordo com a diretiva de EEC 79/831 Anexo V.A8 por HPLC (Cromatografia Líquida de Alta Eficiência) em colunas de fase reversa com os seguintes métodos: [a] Valor de LogP é determinado por medição de LC-UV, em uma faixa ácida, com 0,1% de ácido fórmico em água e acetonitrila como eluente (gradiente linear de 10% de acetonitrila a 95% de acetonitrila). [b] Valor de LogP é determinado por medição de LC-UV, em uma faixa neutra, com 0,001 molar de solução de acetato de amônio em água e acetonitrila como eluente (gradiente linear de 10% de acetonitrila a 95% de acetonitrila). [c] Valor de LogP é determinado por medição de LC-UV, em uma faixa ácida, com 0,1% de ácido fosfórico e acetonitrila como eluente (gradiente linear de 10% de acetonitrila a 95% de acetonitrila).
[00177] Se mais de um Valor de LogP estiver disponível dentro do mesmo método, todos os valores são dados e separados por "+".
[00178] A calibração foi feita com alcan2-onas de cadeia linear (com 3 a 16 átomos de carbono) com valores de LogP conhecidos (medição de valores de LogP usando tempos de retenção com interpolação linear entre sucessivas alcanonas). Os valores de lambda-max foram determinados usando espectros de UV de 200 nm a 400 nm e os valores de pico dos sinais cromatográficos. Listas de Pico de RMN
[00179] A Tabela A fornece os dados de RMN (1H) de alguns compostos divulgados nas tabelas acima. 1
[00180] Os dados de H-RMN de exemplos selecionados são escritos na forma de listas de picos de 1H-RMN. Para cada pico de sinal,
são listados o valor δ em ppm e a intensidade do sinal entre parênteses. Entre os pares de valor δ - intensidade de sinal estão pontos e vírgulas como delimitadores.
[00181] A lista de picos de um exemplo tem, portanto, a forma: δ1 (intensidade1); δ2 (intensidade2); ……..; δi (intensidadei); ……; δn (intensidaden)
[00182] A intensidade dos sinais agudos se correlaciona com a altura dos sinais em um exemplo impresso de um espectro de RMN em cm e mostra as relações reais de intensidades de sinal. A partir de sinais amplos, podem ser mostrados vários picos no meio do sinal e sua intensidade relativa em comparação ao sinal mais intenso do espectro.
[00183] Para calibração do deslocamento químico para espectros de 1 H, utilizou-se tetrametilsilano e/ou o deslocamento químico do solvente utilizado, principalmente no caso de espectros medidos em DMSO. Portanto, nas listas de pico de RMN, pico de tetrametilsilano pode ocorrer, mas não necessariamente.
[00184] As listas de pico de 1H-RMN são semelhantes às impressões clássicas de 1H-RMN e contêm, portanto, geralmente todos os picos, que são listados na interpretação clássica de RMN.
[00185] Além disso, eles podem mostrar como os 1H-RMN clássico imprime sinais de solventes, estereoisômeros dos compostos alvo, que são também objeto da invenção, e/ou picos de impurezas.
[00186] Para mostrar sinais de compostos na faixa delta de solventes e/ou água, os picos usuais de solventes, por exemplo, picos de DMSO em DMSO-D6 e o pico de água são mostrados em nossas listas de pico de 1H-RMN e geralmente têm, em média, uma alta intensidade.
[00187] Os picos de estereoisômeros dos compostos alvo e/ou picos de impurezas têm normalmente uma intensidade média inferior aos picos dos compostos alvo (por exemplo, com uma pureza> 90%).
[00188] Esses estereoisômeros e/ou impurezas podem ser típicos para o processo de preparação específico. Portanto, seus picos podem ajudar a reconhecer a reprodução de processo de preparação da presente invenção via "subprodutos-impressões digitais".
[00189] Um especialista, que calcula os picos dos compostos alvo com métodos conhecidos (MestreC, simulação ACD, mas também com valores de expectativa avaliados empiricamente) pode isolar os picos dos compostos alvo conforme necessário, opcionalmente usando filtros de intensidade adicionais. Esse isolamento seria semelhante ao pico relevante na interpretação clássica de +H-RMN.
[00190] Mais detalhes de descrição de dados de RMN com listas de picos podem ser encontrados na publicação "Citation of NMR Peaklist Data within Patent Applications" do Research Disclosure Database Número 564025. Tabela A: Listas de Picos de RMN II.01: 1H-RMN(499,9 MHz, d6-DMSO): δ= 8,6002 (0,7); 8,5890 (1,4); 8,5779 (0,8); 4,0685 (4,7); 4,0569 (4,8); 3,6736 (16,0); 2,5043 (0,4); 2,5011 (0,3) II.02: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4036 (1,8); 7,2986 (3,0); 4,2389 (2,4); 4,2151 (7,5); 4,1914 (7,6); 4,1676 (2,5); 1,7275 (2,1); 1,7106 (6,0); 1,6998 (6,1); 1,6845 (2,7); 1,6388 (3,0); 1,3739 (2,8); 1,3586 (6,2); 1,3477 (6,2); 1,3308 (2,2); 1,2923 (8,0); 1,2685 (16,0); 1,2447 (7,7); 0,0325 (3,7) II.03: 1H-RMN(499,9 MHz, d6-DMSO): δ= 12,5814 (2,4); 8,7865 (14,0); 3,6061 (0,4); 3,5976 (0,5); 3,5930 (1,0); 3,5885 (0,5); 3,5799 (0,4); 2,5065 (1,2); 2,5031 (1,5); 2,4997 (1,1); 1,7630 (0,5); 1,7567 (0,6); 1,7499 (1,2); 1,7432 (0,6); 1,7369 (0,5); 1,4652 (0,8); 1,4348 (6,7); 1,4252 (15,1); 1,4187 (16,0); 1,4100 (6,6); 1,3784 (0,6); 1,2628 (0,3); 1,2495 (0,4); 1,2313 (0,4); 1,2175 (0,5); 1,1965 (1,0); 1,1648 (7,6); 1,1560 (15,8); 1,1495 (15,3); 1,1400 (5,6); 1,1095 (0,4)
II.04: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4464 (1,1); 7,4208 (1,1); 7,2982 (1,2); 4,8273 (0,8); 4,8112 (0,4); 4,8004 (2,0); 4,7823 (0,9); 4,7739 (1,3); 4,7639 (0,3); 4,7561 (0,6); 4,2982 (2,0); 4,2744 (6,4); 4,2506 (6,7); 4,2269 (2,3); 1,8300 (0,9); 1,8117 (1,3); 1,8062 (0,8); 1,7932 (1,0); 1,7806 (2,5); 1,7735 (1,8); 1,7646 (2,0); 1,7581 (1,7); 1,7430 (2,4); 1,7284 (1,1); 1,7167 (1,5); 1,7113 (0,9); 1,6889 (0,9); 1,4536 (0,9); 1,3552 (7,9); 1,3449 (0,4); 1,3314 (16,0); 1,3076 (7,8); 1,2843 (0,5); 1,2780 (0,5); 1,0372 (0,6); 1,0189 (9,3); 1,0134 (11,5); 1,0060 (7,5); 0,9983 (10,7); 0,9930 (8,4); 0,9613 (0,3); 0,9022 (0,4); 0,0213 (1,0) II.05: 1H-RMN(499,9 MHz, d6-DMSO): δ= 12,7883 (1,2); 8,4631 (6,8); 3,9636 (16,0); 3,9550 (15,4); 3,3294 (6,5); 2,4988 (5,9) II.06: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,7679 (0,8); 8,7508 (0,8); 3,8014 (1,0); 3,7842 (1,0); 3,7783 (1,0); 3,7610 (1,0); 3,6813 (16,0); 3,3322 (31,0); 2,5125 (5,0); 2,5080 (10,4); 2,5033 (13,8); 2,4987 (10,0); 2,4942 (4,8); 1,2741 (0,6); 1,2627 (0,6); 1,2511 (0,6); 1,2392 (0,6); 1,2311 (0,4); 0,6263 (0,5); 0,6174 (0,6); 0,6125 (0,5); 0,6054 (0,4); 0,6026 (0,6); 0,5974 (0,3); 0,5915 (0,4); 0,5816 (0,4); 0,5519 (0,4); 0,5481 (0,4); 0,5387 (0,5); 0,5318 (0,4); 0,5280 (0,5); 0,5182 (0,6); 0,4967 (0,5); 0,4829 (0,4); 0,4735 (0,7); 0,4613 (0,8); 0,4502 (0,6); 0,4065 (0,4); 0,3950 (0,5); 0,3831 (0,6); 0,3705 (0,6); 0,3611 (0,3) II.07: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4814 (1,6); 7,2987 (4,9); 4,6610 (3,8); 4,6335 (11,5); 4,6060 (11,6); 4,5785 (3,9); 4,4125 (16,0); 4,3949 (15,8); 1,6310 (2,7); 1,2890 (0,6); 0,0339 (5,1) II.08: 1H-RMN(300,2 MHz, CDCl3): δ= 7,6120 (2,6); 7,4669 (4,1); 7,4611 (2,1); 7,4418 (9,8); 7,4151 (7,4); 7,3289 (3,8); 7,3040 (5,5); 7,2990 (4,0); 7,2796 (1,9); 7,1915 (8,5); 7,1878 (10,6); 7,1623 (8,3); 4,5518 (16,0); 4,5350 (15,8); 1,6992 (0,4); 1,2954 (0,6); 0,0401 (1,6)
II.09: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5673 (0,6); 7,2989 (0,8); 5,1972 (0,4); 5,1763 (1,0); 5,1554 (1,4); 5,1345 (1,0); 5,1136 (0,4); 4,2375 (5,2); 4,2214 (5,2); 1,3391 (16,0); 1,3182 (15,9); 0,0264 (0,8) II.10: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5607 (1,0); 7,2988 (3,5); 4,2879 (10,1); 4,2716 (10,0); 4,2343 (4,8); 4,2119 (9,9); 4,1896 (5,0); 1,8025 (0,6); 1,7781 (2,3); 1,7549 (4,7); 1,7308 (4,9); 1,7075 (2,7); 1,6835 (0,8); 1,6555 (0,7); 1,2876 (0,4); 1,0257 (8,2); 1,0010 (16,0); 0,9762 (7,2); 0,1125 (0,7); 0,1061 (0,7); 0,0326 (3,1) II.11: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5588 (1,2); 7,2988 (3,0); 4,2786 (11,2); 4,2626 (10,6); 4,2524 (10,2); 4,2302 (5,0); 1,7443 (1,0); 1,7211 (3,0); 1,7124 (1,1); 1,6984 (3,7); 1,6720 (3,2); 1,6498 (1,4); 1,4942 (0,7); 1,4696 (2,2); 1,4440 (3,3); 1,4186 (3,4); 1,4017 (0,6); 1,3945 (2,1); 1,3705 (0,7); 1,2863 (0,4); 1,0040 (8,2); 0,9796 (16,0); 0,9551 (6,5); 0,0313 (2,0) II.12: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5454 (0,7); 7,2990 (2,2); 4,3171 (0,4); 4,3063 (0,5); 4,3013 (0,9); 4,2964 (0,6); 4,2854 (1,4); 4,2759 (0,8); 4,2708 (0,8); 4,2685 (0,7); 4,2647 (0,6); 4,2479 (7,5); 4,2315 (7,4); 0,8276 (0,9); 0,8159 (5,2); 0,8134 (5,4); 0,8056 (2,1); 0,7989 (16,0); 0,0312 (1,9) II.13: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5492 (1,1); 7,4393 (0,6); 7,4293 (1,6); 7,4157 (24,7); 7,3935 (0,7); 7,3871 (0,7); 7,2990 (4,9); 5,2796 (16,0); 4,3335 (8,8); 4,3170 (8,8); 1,2936 (0,6); 0,0388 (4,6)
II.14: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,4879 (0,8); 8,4686 (0,8); 4,3850 (1,0); 4,3689 (1,2); 4,3660 (1,2); 4,3499 (1,0); 3,6820 (16,0); 3,3261 (19,3); 2,5254 (0,5); 2,5206 (0,7); 2,5119 (8,8); 2,5075 (18,2); 2,5029 (24,0); 2,4983 (17,6); 2,4938 (8,6); 1,9663 (0,4); 1,9613 (0,3); 1,9553 (0,4); 1,9499 (0,5); 1,9446 (0,4); 1,9387 (0,3); 1,9333 (0,4); 1,4838 (0,4); 1,4724 (0,4); 1,4686 (0,5); 1,4574 (0,4); 1,4499 (0,4); 1,4387 (0,4); 1,2882 (0,4); 1,2698 (0,6); 1,2665 (0,5); 1,2538 (0,5); 1,2478 (0,6); 1,2362 (0,7); 1,2138 (0,3); 0,9135 (5,9); 0,8962 (6,6); 0,8752 (6,2); 0,8566 (2,5); -0,0002 (3,4) II.15: 1H-RMN(400,2 MHz, d6-DMSO): δ= 9,2545 (6,6); 8,4347 (2,1); 8,4161 (2,1); 7,9525 (0,6); 7,0523 (5,7); 7,0313 (6,5); 6,6853 (0,9); 6,6785 (7,0); 6,6574 (6,6); 4,5849 (0,7); 4,5710 (1,0); 4,5635 (1,4); 4,5513 (1,2); 4,5446 (1,1); 4,5307 (0,8); 4,1422 (1,5); 4,1366 (0,5); 4,1246 (4,6); 4,1072 (4,6); 4,0973 (0,4); 4,0900 (1,6); 3,3310 (27,2); 3,0779 (0,9); 3,0644 (1,0); 3,0432 (2,0); 3,0297 (1,9); 2,9974 (2,0); 2,9752 (1,9); 2,9628 (1,0); 2,9405 (0,9); 2,8908 (4,3); 2,7317 (3,9); 2,5115 (16,6); 2,5074 (32,8); 2,5029 (43,1); 2,4984 (32,1); 2,4941 (16,2); 1,2383 (1,0); 1,1901 (7,7); 1,1724 (16,0); 1,1546 (7,4); -0,0002 (5,1) II.16: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5444 (1,9); 7,2988 (3,2); 5,1740 (0,6); 5,1498 (2,4); 5,1244 (3,5); 5,0998 (2,4); 5,0757 (0,6); 4,2524 (16,0); 4,2362 (15,8); 2,4686 (1,0); 2,4595 (1,5); 2,4498 (1,3); 2,4421 (1,9); 2,4356 (2,8); 2,4333 (2,8); 2,4270 (3,1); 2,4183 (2,9); 2,4093 (3,2); 2,4006 (3,6); 2,3941 (2,6); 2,3866 (1,8); 2,3766 (2,0); 2,3680 (1,6); 2,2298 (0,8); 2,2274 (0,8); 2,2199 (0,6); 2,2014 (1,6); 2,1953 (3,4); 2,1860 (2,2); 2,1753 (1,3); 2,1691 (3,4); 2,1624 (3,6); 2,1607 (3,6); 2,1536 (2,9); 2,1366 (2,5); 2,1275 (2,9); 2,1224 (1,6); 2,1037 (0,9); 2,0957 (0,8); 2,0932 (0,8); 2,0400 (1,0); 1,9302 (0,5); 1,9238 (0,8); 1,9215 (0,8); 1,9152 (0,5); 1,8876 (2,0); 1,8616 (1,2); 1,8542 (2,0); 1,8441 (1,0); 1,8300 (0,5); 1,8272 (0,5); 1,8210 (0,8); 1,8183 (0,8); 1,8121 (0,5); 1,7628 (0,9); 1,7360 (1,6); 1,7302 (1,4); 1,7277 (1,5); 1,7089 (1,1); 1,7021 (2,8); 1,6955 (1,5); 1,6723 (1,4); 1,6658 (2,1); 1,6589 (0,7); 1,6397 (1,0); 1,6318 (0,9); 1,6048 (0,4); 1,2842 (1,0); 0,0293 (2,6)
II.17: 1H-RMN(499,9 MHz, CDCl3): δ= 7,5067 (1,1); 7,2620 (7,1); 5,5609 (0,4); 5,5580 (0,6); 5,5551 (0,4); 5,5463 (0,8); 5,5434 (1,3); 5,5401 (1,0); 5,5365 (0,9); 5,5329 (0,7); 5,5288 (0,8); 5,5251 (1,0); 5,5219 (1,4); 5,5189 (0,8); 5,5102 (0,4); 5,5073 (0,7); 5,5044 (0,4); 5,3328 (0,5); 5,3298 (0,8); 5,3267 (0,5); 5,3182 (0,9); 5,3152 (1,5); 5,3119 (1,1); 5,3083 (0,8); 5,3042 (0,7); 5,3005 (0,9); 5,2970 (1,0); 5,2936 (1,2); 5,2905 (0,7); 5,2821 (0,4); 5,2790 (0,6); 4,2414 (9,9); 4,2316 (9,9); 4,2255 (4,8); 4,2117 (9,0); 4,1978 (4,4); 2,4521 (1,3); 2,4507 (1,3); 2,4493 (1,3); 2,4370 (3,3); 2,4355 (3,3); 2,4237 (3,2); 2,4225 (3,2); 2,4099 (1,1); 2,4086 (1,0); 2,4072 (1,0); 2,0901 (0,6); 2,0885 (0,6); 2,0872 (0,7); 2,0751 (2,2); 2,0736 (2,1); 2,0723 (2,2); 2,0602 (3,2); 2,0588 (3,1); 2,0574 (3,1); 2,0453 (2,2); 2,0440 (2,1); 2,0424 (2,1); 2,0303 (0,6); 2,0290 (0,6); 2,0275 (0,6); 1,5675 (3,2); 0,9888 (8,3); 0,9737 (16,0); 0,9586 (7,6); 0,0063 (0,6); -0,0002 (8,5) II.18: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5667 (1,5); 7,2986 (22,3); 4,3113 (16,0); 4,2951 (15,8); 4,0974 (14,1); 4,0728 (14,4); 2,9949 (1,6); 2,9225 (1,3); 1,5968 (10,9); 1,2905 (1,3); 1,2728 (0,4); 1,2568 (0,6); 1,2478 (0,8); 1,2411 (0,5); 1,2318 (1,5); 1,2212 (1,2); 1,2162 (1,0); 1,2054 (2,4); 1,1949 (1,0); 1,1893 (1,3); 1,1791 (1,6); 1,1700 (0,4); 1,1632 (0,9); 1,1541 (0,6); 1,1382 (0,4); 0,6817 (1,7); 0,6657 (4,8); 0,6611 (5,8); 0,6575 (3,7); 0,6454 (2,5); 0,6384 (5,6); 0,6345 (4,6); 0,6188 (2,1); 0,5961 (0,3); 0,3781 (2,2); 0,3624 (6,8); 0,3464 (5,2); 0,3424 (6,7); 0,3266 (1,4); 0,0470 (0,8); 0,0438 (0,4); 0,0362 (26,0); 0,0269 (0,7); 0,0253 (1,0) II.19: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5566 (0,5); 7,2983 (1,3); 4,2964 (4,6); 4,2802 (4,5); 4,0449 (4,7); 4,0227 (4,8); 2,0606 (0,4); 2,0383 (0,9); 2,0158 (1,1); 1,9935 (0,9); 1,9712 (0,5); 1,6501 (0,8); 0,9991 (16,0); 0,9767 (15,3); 0,0313 (1,3) II.20: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5248 (1,4); 7,2990 (4,9); 4,8486 (15,7); 4,8403 (16,0); 4,3487 (14,6); 4,3318 (14,5); 2,5835 (4,1); 2,5753 (8,3); 2,5671 (4,1); 2,0438 (1,8); 1,6279 (2,6); 1,2872 (0,8); 0,0332 (5,7)
II.21: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4736 (0,8); 7,2988 (2,6); 4,8793 (16,0); 4,4081 (0,4); 4,3978 (7,5); 4,3798 (7,4); 3,8555 (0,5); 3,8286 (0,5); 1,2882 (0,3); 0,0335 (1,7) II.22: 1H-RMN(499,9 MHz, CDCl3): δ= 7,5155 (1,8); 7,2702 (2,2); 5,9745 (1,1); 5,9628 (2,1); 5,9536 (1,3); 5,9512 (1,2); 5,9419 (2,4); 5,9285 (2,5); 5,9193 (1,3); 5,9168 (1,3); 5,9076 (2,3); 5,8959 (1,2); 5,3894 (1,8); 5,3866 (3,9); 5,3838 (4,0); 5,3811 (1,7); 5,3550 (1,6); 5,3522 (3,5); 5,3495 (3,5); 5,3467 (1,5); 5,3100 (4,2); 5,3077 (4,1); 5,2891 (3,9); 5,2868 (3,8); 4,7179 (6,0); 4,7155 (9,0); 4,7131 (5,8); 4,7062 (5,7); 4,7038 (8,6); 4,7014 (5,2); 4,2788 (16,0); 4,2688 (15,7); - 0,0002 (2,5) II.23: 1H-RMN(300,2 MHz, CDCl3): δ= 7,5591 (0,9); 7,2984 (13,3); 4,2872 (8,2); 4,2709 (8,2); 3,9517 (16,0); 1,5936 (7,3); 1,2912 (0,4); 0,3334 (0,4); 0,1551 (0,4); 0,1537 (0,4); 0,1521 (0,6); 0,1468 (3,1); 0,1452 (2,0); 0,1358 (91,8); 0,1264 (2,5); 0,1247 (3,2); 0,1193 (0,7); 0,1179 (0,5); 0,1163 (0,4); 0,1149 (0,4); 0,1134 (0,3); 0,0690 (0,4); 0,0471 (0,5); 0,0439 (0,4); 0,0362 (15,4); 0,0285 (0,5); 0,0269 (0,5); 0,0254 (0,6); -0,0648 (0,4) II.24: 1H-RMN(300,2 MHz, CDCl3): δ= 7,2986 (0,4); 4,1782 (1,9); 4,1625 (1,9); 2,0393 (0,4); 1,5423 (16,0); 0,0299 (0,4) II.25: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,5555 (1,7); 8,5367 (1,8); 7,3179 (0,8); 7,3152 (1,2); 7,3115 (0,5); 7,2970 (3,8); 7,2947 (3,3); 7,2862 (1,1); 7,2785 (7,6); 7,2714 (7,8); 7,2553 (2,2); 7,2436 (1,4); 7,2394 (1,4); 7,2332 (0,8); 7,2288 (0,9); 7,2223 (2,2); 7,2146 (0,6); 7,2110 (0,5); 7,2056 (0,8); 7,2009 (0,4); 4,6751 (0,7); 4,6615 (1,0); 4,6559 (1,0); 4,6523 (1,2); 4,6424 (1,1); 4,6387 (1,1); 4,6333 (1,1); 4,6196 (0,8); 4,1502 (1,6); 4,1429 (0,3); 4,1327 (5,2); 4,1152 (5,5); 4,0975 (1,9); 3,3267 (21,0); 3,2077 (1,0); 3,1941 (1,0); 3,1732 (2,0); 3,1597 (1,8); 3,1181 (2,0); 3,0950 (2,0); 3,0838 (1,1); 3,0606 (1,0); 2,8912 (0,6); 2,7324 (0,6); 2,5255 (0,4); 2,5120 (10,2); 2,5076 (20,6); 2,5031 (27,0); 2,4985 (19,3); 2,4941 (9,2); 1,2382 (0,5); 1,1855 (7,7); 1,1678 (16,0); 1,1500 (7,4); 0,0080 (0,5); -0,0002 (13,7); -0,0084 (0,5)
II.26: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,5551 (1,7); 8,5364 (1,7); 7,3178 (0,8); 7,3152 (1,2); 7,3115 (0,6); 7,2969 (3,9); 7,2946 (3,4); 7,2861 (1,2); 7,2783 (7,6); 7,2712 (8,0); 7,2551 (2,3); 7,2436 (1,4); 7,2395 (1,4); 7,2332 (0,9); 7,2287 (0,9); 7,2223 (2,2); 7,2147 (0,6); 7,2111 (0,5); 7,2056 (0,8); 7,2011 (0,4); 4,6747 (0,7); 4,6610 (0,9); 4,6556 (1,0); 4,6520 (1,2); 4,6420 (1,0); 4,6383 (1,0); 4,6331 (1,0); 4,6194 (0,7); 4,1500 (1,7); 4,1428 (0,4); 4,1325 (5,3); 4,1150 (5,5); 4,1051 (0,4); 4,0973 (1,9); 3,3270 (32,9); 3,2074 (1,0); 3,1938 (1,0); 3,1730 (2,0); 3,1594 (1,9); 3,1179 (2,0); 3,0948 (2,0); 3,0835 (1,1); 3,0604 (1,0); 2,8914 (0,4); 2,7323 (0,4); 2,5254 (0,5); 2,5120 (11,4); 2,5076 (23,2); 2,5031 (30,6); 2,4985 (22,3); 2,4942 (11,0); 1,2385 (0,5); 1,1855 (7,7); 1,1678 (16,0); 1,1500 (7,4); 0,0079 (0,5); -0,0002 (14,6); -0,0085 (0,6) II.27: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,6591 (1,7); 8,6400 (1,7); 4,4383 (0,7); 4,4267 (0,9); 4,4191 (0,8); 4,4133 (1,0); 4,4077 (1,0); 4,4011 (0,9); 4,3942 (0,8); 4,3821 (0,8); 4,1660 (0,5); 4,1568 (1,0); 4,1476 (1,4); 4,1390 (3,1); 4,1296 (3,4); 4,1212 (3,4); 4,1119 (3,2); 4,1031 (1,5); 4,0942 (1,0); 4,0849 (0,6); 3,3257 (31,0); 2,5259 (0,5); 2,5210 (0,8); 2,5124 (10,9); 2,5080 (21,9); 2,5034 (28,5); 2,4988 (20,2); 2,4943 (9,6); 1,7964 (0,5); 1,7845 (0,8); 1,7707 (0,6); 1,7640 (0,8); 1,7587 (1,0); 1,7524 (1,1); 1,7385 (0,6); 1,7270 (1,1); 1,7070 (0,7); 1,7025 (0,6); 1,6902 (0,8); 1,6861 (0,8); 1,6735 (0,8); 1,6700 (0,6); 1,6577 (0,5); 1,6245 (1,2); 1,6121 (1,0); 1,6029 (0,7); 1,5918 (1,4); 1,5804 (0,8); 1,5707 (0,6); 1,5596 (0,4); 1,2387 (1,1); 1,2147 (7,6); 1,1970 (16,0); 1,1792 (7,4); 0,9283 (9,9); 0,9123 (9,5); 0,8951 (9,3); 0,8792 (9,4); 0,8530 (0,3); 0,0080 (0,5); -0,0002 (15,0); -0,0085 (0,5)
II.28: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,6568 (1,6); 8,6377 (1,6); 4,4395 (0,7); 4,4279 (0,9); 4,4203 (0,8); 4,4145 (1,0); 4,4088 (1,1); 4,4023 (0,9); 4,3954 (0,8); 4,3831 (0,8); 4,1667 (0,6); 4,1575 (1,0); 4,1483 (1,5); 4,1397 (3,2); 4,1303 (3,4); 4,1218 (3,4); 4,1126 (3,2); 4,1038 (1,5); 4,0949 (1,0); 4,0856 (0,6); 3,3256 (21,7); 2,5264 (0,4); 2,5216 (0,7); 2,5130 (8,3); 2,5085 (16,7); 2,5040 (21,9); 2,4994 (15,6); 2,4949 (7,4); 1,7971 (0,5); 1,7853 (0,8); 1,7714 (0,6); 1,7648 (0,8); 1,7595 (1,0); 1,7532 (1,1); 1,7394 (0,6); 1,7279 (1,1); 1,7078 (0,7); 1,7035 (0,6); 1,6911 (0,8); 1,6870 (0,8); 1,6746 (0,8); 1,6709 (0,6); 1,6585 (0,5); 1,6253 (1,2); 1,6128 (1,0); 1,6037 (0,7); 1,5926 (1,4); 1,5812 (0,8); 1,5715 (0,6); 1,5603 (0,4); 1,2382 (1,0); 1,2155 (7,8); 1,1978 (16,0); 1,1800 (7,4); 0,9288 (10,0); 0,9128 (9,5); 0,8957 (9,4); 0,8798 (9,4); 0,8529 (0,3); 0,0080 (0,4); - 0,0002 (11,8); -0,0085 (0,4) II.29: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4224 (1,0); 7,2991 (0,5); 3,7387 (16,0); 1,7312 (1,4); 1,7144 (3,1); 1,7035 (3,2); 1,6881 (1,4); 1,3670 (1,4); 1,3514 (3,2); 1,3407 (3,2); 1,3237 (1,1); 0,0225 (0,7) II.30: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,1199 (2,3); 8,0990 (2,3); 7,9549 (0,9); 4,5040 (2,5); 4,4930 (2,6); 4,4830 (2,6); 4,4720 (2,5); 2,8939 (6,6); 2,7351 (5,4); 2,7339 (5,4); 2,5487 (2,3); 2,5277 (0,5); 2,5229 (0,8); 2,5143 (11,6); 2,5098 (24,0); 2,5053 (31,7); 2,5007 (22,7); 2,4961 (10,8); 2,0302 (0,6); 2,0185 (0,7); 2,0129 (1,2); 2,0013 (1,3); 1,9954 (1,4); 1,9839 (1,3); 1,9781 (0,8); 1,9667 (0,7); 1,4409 (0,8); 1,4237 (1,3); 1,4063 (1,9); 1,3887 (1,8); 1,3714 (1,2); 1,3533 (0,4); 1,2692 (0,4); 1,2656 (0,5); 1,2467 (1,4); 1,2383 (0,9); 1,2282 (2,2); 1,2099 (1,6); 1,1938 (1,5); 1,1754 (1,0); 0,9615 (0,5); 0,9444 (0,7); 0,9267 (15,5); 0,9162 (9,2); 0,9095 (15,8); 0,8979 (16,0); 0,8794 (6,4); 0,8532 (0,5); 0,8359 (0,3); 0,0080 (0,6); -0,0002 (20,8); -0,0085 (0,8)
II.31: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,4776 (3,5); 8,4582 (3,3); 7,9558 (0,6); 4,4027 (1,3); 4,3918 (1,9); 4,3783 (2,0); 4,3724 (2,2); 4,3478 (1,2); 2,8941 (3,3); 2,7349 (3,2); 2,5503 (1,6); 2,5092 (36,0); 2,5056 (38,6); 1,7820 (0,9); 1,7708 (1,3); 1,7442 (2,5); 1,7409 (2,5); 1,7157 (2,6); 1,6949 (2,0); 1,6788 (1,8); 1,6638 (1,4); 1,6425 (2,4); 1,6301 (1,7); 1,6222 (1,6); 1,6115 (2,4); 1,6004 (1,4); 1,5909 (1,0); 1,5817 (0,6); 1,2397 (0,9); 0,9257 (16,0); 0,9103 (15,9); 0,8956 (15,6); 0,8802 (14,1); 0,8551 (0,8); 0,0011 (14,0); -0,0002 (15,2) II.32: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,3405 (2,5); 8,3213 (2,6); 7,9541 (0,8); 7,3064 (1,6); 7,3027 (0,8); 7,2916 (2,6); 7,2880 (5,5); 7,2860 (5,0); 7,2708 (16,0); 7,2654 (12,2); 7,2531 (2,3); 7,2496 (3,1); 7,2324 (2,0); 7,2279 (2,0); 7,2209 (1,3); 7,2177 (1,5); 7,2109 (3,0); 7,2030 (1,0); 7,2007 (1,0); 7,1946 (1,2); 7,1896 (0,7); 4,6455 (1,0); 4,6337 (1,3); 4,6230 (1,8); 4,6140 (1,7); 4,6115 (1,6); 4,6035 (1,4); 4,5916 (1,1); 3,2373 (1,6); 3,2254 (1,8); 3,2027 (2,7); 3,1909 (2,4); 3,1094 (2,5); 3,0865 (2,5); 3,0750 (1,7); 3,0521 (1,6); 2,8916 (6,1); 2,7340 (5,0); 2,7330 (5,1); 2,5499 (1,4); 2,5416 (0,4); 2,5268 (0,6); 2,5135 (12,5); 2,5090 (25,2); 2,5045 (32,8); 2,4999 (23,5); 2,4954 (11,2); 2,0523 (0,4); 1,2510 (0,4); 1,2374 (0,9); 0,0079 (0,8); -0,0002 (20,3); -0,0085 (0,7) II.33: 1H-RMN(300,2 MHz, d6-DMSO): δ= 12,8679 (3,8); 8,5539 (15,3); 8,5302 (15,5); 7,9706 (0,7); 3,8137 (13,3); 3,7898 (15,1); 3,7843 (16,0); 3,7603 (13,6); 3,6989 (0,6); 3,3653 (2,7); 3,1866 (2,6); 2,9091 (5,1); 2,7488 (4,2); 2,5339 (6,2); 2,5280 (13,7); 2,5220 (19,2); 2,5160 (14,1); 2,5101 (6,7); 1,3266 (1,3); 1,3103 (3,2); 1,2987 (4,2); 1,2830 (7,4); 1,2679 (6,5); 1,2547 (8,0); 1,2387 (4,8); 1,2275 (3,8); 1,2111 (1,9); 0,6798 (0,5); 0,6511 (3,5); 0,6448 (3,5); 0,6339 (6,0); 0,6233 (5,3); 0,6161 (7,7); 0,6058 (10,2); 0,5881 (5,2); 0,5836 (4,2); 0,5773 (5,0); 0,5652 (4,1); 0,5539 (5,0); 0,5486 (6,0); 0,5364 (8,9); 0,5277 (5,0); 0,5204 (8,9); 0,5157 (10,0); 0,5098 (13,1); 0,4935 (10,9); 0,4877 (14,0); 0,4744 (8,8); 0,4704 (10,3); 0,4588 (9,0); 0,4424 (4,2); 0,4237 (6,1); 0,4127 (5,9); 0,4083 (6,4); 0,3967 (10,7); 0,3792 (7,8); 0,3611 (3,9); 0,3365 (0,8); 0,0263 (0,4); 0,0155 (13,4); 0,0046 (0,5)
II.34: 1H-RMN(400,1 MHz, d6-DMSO): δ= 8,7678 (2,1); 8,7510 (2,1); 4,1866 (0,9); 4,1773 (1,0); 4,1688 (1,0); 4,1593 (3,7); 4,1512 (0,6); 4,1413 (5,6); 4,1315 (0,6); 4,1233 (3,8); 4,1139 (1,0); 4,1054 (1,0); 4,0961 (0,9); 3,7652 (2,0); 3,7480 (2,1); 3,7423 (2,2); 3,7251 (2,0); 3,3320 (104,7); 2,5067 (14,8); 2,5023 (19,6); 2,4979 (14,3); 1,2789 (0,6); 1,2677 (0,8); 1,2583 (1,4); 1,2471 (1,4); 1,2359 (1,6); 1,2233 (8,4); 1,2055 (16,0); 1,1878 (7,4); 0,6429 (0,4); 0,6334 (0,5); 0,6299 (0,6); 0,6214 (1,1); 0,6127 (1,2); 0,6080 (1,2); 0,5981 (1,3); 0,5869 (0,8); 0,5770 (0,7); 0,5604 (0,7); 0,5470 (1,0); 0,5379 (1,2); 0,5270 (1,2); 0,5171 (1,4); 0,5049 (0,6); 0,4961 (1,2); 0,4827 (1,0); 0,4735 (1,4); 0,4611 (1,7); 0,4500 (1,3); 0,4375 (0,6); 0,4100 (0,8); 0,3982 (1,2); 0,3867 (1,4); 0,3743 (1,3); 0,3646 (0,8); 0,3524 (0,3); 0,0078 (0,6); -0,0002 (12,2) II.35: 1H-RMN(300,2 MHz, CDCl3): δ= 7,2986 (1,0); 4,2923 (1,4); 4,2686 (4,1); 4,2447 (4,7); 4,2211 (2,5); 3,1655 (16,0); 2,0305 (2,0); 1,7399 (0,5); 1,3459 (4,6); 1,3221 (9,1); 1,2983 (4,5); 0,0193 (0,8) II.36: 1H-RMN(400,2 MHz, d6-DMSO): δ= 9,0925 (2,4); 5,7253 (0,5); 5,6998 (0,7); 5,6823 (0,7); 5,6775 (0,7); 5,6597 (0,8); 5,6570 (0,9); 5,6344 (0,7); 5,3539 (1,3); 5,3499 (1,4); 5,3112 (1,0); 5,3069 (1,1); 5,1553 (1,4); 5,1508 (1,3); 5,1296 (1,2); 5,1251 (1,2); 3,6272 (16,0); 3,3613 (37,5); 3,3534 (49,9); 2,5285 (0,4); 2,5148 (7,3); 2,5107 (14,5); 2,5063 (18,8); 2,5019 (14,0); 2,3765 (0,4); 2,3544 (1,2); 2,3326 (1,3); 2,3104 (0,5); 1,7474 (1,1); 1,7340 (1,3); 1,7273 (1,2); 1,7139 (1,2); 1,4966 (1,2); 1,4832 (1,2); 1,4728 (1,2); 1,4596 (1,0); -0,0002 (0,4)
II.37: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,5560 (1,7); 8,5371 (1,8); 7,3181 (0,7); 7,3153 (1,2); 7,3115 (0,5); 7,3003 (1,9); 7,2971 (3,7); 7,2946 (3,2); 7,2865 (1,0); 7,2785 (7,1); 7,2713 (7,4); 7,2552 (2,2); 7,2505 (1,0); 7,2438 (1,4); 7,2396 (1,4); 7,2332 (0,8); 7,2289 (0,9); 7,2223 (2,2); 7,2147 (0,5); 7,2109 (0,5); 7,2057 (0,8); 7,2010 (0,4); 4,6747 (0,7); 4,6610 (0,9); 4,6555 (0,9); 4,6519 (1,1); 4,6420 (1,0); 4,6384 (1,0); 4,6329 (1,0); 4,6192 (0,7); 4,1499 (1,6); 4,1322 (4,9); 4,1151 (5,1); 4,0973 (1,8); 3,3264 (26,3); 3,2073 (0,9); 3,1938 (1,0); 3,1730 (1,9); 3,1595 (1,7); 3,1178 (1,8); 3,0947 (1,8); 3,0834 (1,0); 3,0603 (0,9); 2,8912 (0,9); 2,7330 (0,7); 2,7320 (0,7); 2,5254 (0,5); 2,5207 (0,8); 2,5120 (10,9); 2,5076 (22,3); 2,5030 (29,4); 2,4984 (21,1); 2,4939 (10,0); 1,2383 (0,6); 1,1854 (7,6); 1,1676 (16,0); 1,1498 (7,3); 0,0080 (0,6); -0,0002 (15,9); - 0,0085 (0,5) XVIa.01: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,5905 (1,3); 8,5766 (2,4); 8,5627 (1,3); 8,0808 (11,2); 4,1587 (2,5); 4,1409 (7,5); 4,1232 (7,6); 4,1054 (2,6); 4,0334 (8,7); 4,0188 (8,7); 3,3611 (31,7); 3,3532 (84,8); 3,3511 (80,8); 2,8943 (0,4); 2,7353 (0,4); 2,5101 (24,1); 2,5060 (30,3); 2,5019 (23,8); 1,2596 (0,3); 1,2306 (8,4); 1,2128 (16,0); 1,1950 (7,8); -0,0002 (0,4) XVIa.02: 1H-RMN(400,2 MHz, d6-DMSO): δ= 8,5114 (2,4); 8,4927 (2,4); 8,0322 (9,2); 7,9527 (0,4); 7,3139 (1,2); 7,2949 (5,0); 7,2783 (15,4); 7,2606 (3,1); 7,2431 (2,0); 7,2384 (2,0); 7,2292 (1,8); 7,2219 (2,5); 7,2133 (1,2); 7,2060 (1,0); 4,6722 (1,0); 4,6582 (1,4); 4,6499 (1,8); 4,6391 (1,7); 4,6364 (1,7); 4,6309 (1,6); 4,6170 (1,1); 4,1493 (2,0); 4,1319 (6,1); 4,1143 (6,4); 4,0967 (2,3); 3,3611 (133,1); 3,2025 (1,1); 3,1889 (1,3); 3,1681 (2,6); 3,1545 (2,5); 3,1222 (2,6); 3,0993 (2,5); 3,0879 (1,4); 3,0648 (1,2); 2,8937 (2,2); 2,7358 (2,0); 2,5102 (30,4); 2,5062 (37,7); 1,2599 (0,4); 1,2389 (1,5); 1,1881 (7,9); 1,1703 (16,0); 1,1526 (7,7); -0,0002 (0,6)
XVIa.03: 1H-RMN(300,2 MHz, CDCl3): δ= 7,4800 (10,7); 7,4607 (1,7); 7,2990 (20,9); 4,2466 (2,4); 4,2229 (7,4); 4,1991 (7,5); 4,1754 (2,5); 1,7396 (2,1); 1,7228 (6,0); 1,7120 (6,1); 1,6967 (2,7); 1,6435 (0,4); 1,5945 (4,6); 1,3841 (2,8); 1,3688 (6,2); 1,3580 (6,1); 1,3412 (2,3); 1,2987 (8,4); 1,2749 (16,0); 1,2512 (7,7); 0,0477 (1,1); 0,0370 (26,5); 0,0261 (1,0) XVIb.01: 1H-RMN(600,1 MHz, d6-DMSO): δ= 7,3701 (2,1); 4,1442 (0,4); 4,1324 (1,3); 4,1205 (1,3); 4,1087 (0,4); 3,9635 (1,4); 3,9537 (1,4); 3,3515 (3,3); 3,3467 (10,2); 3,3448 (16,0); 2,5148 (1,2); 2,5119 (2,6); 2,5088 (3,6); 2,5058 (2,6); 2,5028 (1,2); 1,2244 (1,5); 1,2125 (3,1); 1,2007 (1,4) XVIb.02: 1H-RMN(600,1 MHz, d6-DMSO): δ= 8,7305 (0,8); 8,7177 (0,8); 7,3044 (0,5); 7,2915 (1,9); 7,2797 (4,0); 7,2758 (3,2); 7,2652 (0,8); 7,2607 (4,4); 7,2297 (0,4); 7,2266 (0,6); 7,2153 (0,8); 7,2042 (0,3); 4,5937 (0,4); 4,5843 (0,4); 4,5809 (0,4); 4,5775 (0,5); 4,5715 (0,4); 4,5681 (0,4); 4,5647 (0,4); 4,5553 (0,4); 4,1073 (0,6); 4,0954 (1,9); 4,0836 (2,0); 4,0717 (0,7); 3,3321 (4,6); 3,3263 (15,2); 3,3250 (16,0); 3,3247 (16,0); 3,1399 (0,5); 3,1306 (0,5); 3,1169 (0,8); 3,1076 (0,7); 3,0345 (0,8); 3,0181 (0,8); 3,0115 (0,5); 2,9951 (0,5); 2,5079 (3,2); 2,5050 (6,7); 2,5021 (9,1); 2,4991 (6,4); 2,4962 (2,9); 1,2392 (0,3); 1,1501 (2,9); 1,1382 (6,1); 1,1264 (2,9) XVIb.03: 1H-RMN(600,1 MHz, d6-DMSO): δ= 8,9132 (1,4); 8,3126 (2,4); 7,3320 (4,3); 4,0805 (1,0); 4,0687 (3,2); 4,0569 (3,2); 4,0450 (1,0); 3,3322 (5,3); 3,3237 (16,0); 3,3000 (0,9); 2,5083 (2,8); 2,5054 (6,1); 2,5023 (8,6); 2,4993 (6,4); 2,4964 (3,1); 1,4308 (0,9); 1,4230 (2,4); 1,4175 (2,7); 1,4101 (1,0); 1,1667 (3,4); 1,1549 (7,0); 1,1431 (3,3); 1,1303 (1,0); 1,1229 (2,4); 1,1174 (2,4); 1,1095 (0,9) XVIc.01: 1H-RMN(300,2 MHz, d6-DMSO): δ= 9,3043 (2,1); 7,8355 (6,1); 3,6265 (16,0); 3,3513 (2,6); 2,5338 (0,5); 2,5280 (1,1); 2,5220 (1,4); 2,5160 (1,0); 2,5102 (0,5); 1,5032 (1,1); 1,4868 (2,8); 1,4758 (3,0); 1,4614 (1,3); 1,2090 (1,4); 1,1945 (3,0); 1,1835 (2,8); 1,1671 (1,0); 0,0164 (0,9)
XVIc.02: 1H-RMN(400,2 MHz, d6-DMSO): δ= 9,4344 (2,4); 7,9531 (0,5); 7,8277 (6,2); 5,7160 (0,5); 5,6907 (0,7); 5,6731 (0,7); 5,6679 (0,7); 5,6502 (0,8); 5,6478 (0,9); 5,6249 (0,7); 5,3627 (1,3); 5,3586 (1,4); 5,3199 (1,0); 5,3157 (1,1); 5,1644 (1,4); 5,1599 (1,3); 5,1387 (1,2); 5,1342 (1,2); 3,6188 (16,0); 3,3472 (21,9); 3,3420 (29,0); 2,8947 (3,7); 2,7358 (3,2); 2,5279 (0,4); 2,5145 (6,8); 2,5102 (13,7); 2,5058 (18,0); 2,5013 (13,4); 2,4971 (7,0); 2,3289 (0,5); 2,3066 (1,1); 2,2853 (1,2); 2,2629 (0,5); 1,7569 (1,1); 1,7437 (1,2); 1,7371 (1,2); 1,7238 (1,1); 1,4771 (1,2); 1,4639 (1,2); 1,4534 (1,2); 1,4402 (1,0); 1,2398 (0,5); -0,0002 (0,3) XVIc.03: 1H-RMN(400,2 MHz, d6-DMSO): δ= 9,2095 (1,0); 9,1929 (1,0); 8,0335 (6,6); 3,7135 (1,1); 3,6968 (1,1); 3,6897 (1,3); 3,6825 (0,5); 3,6728 (1,4); 3,6640 (16,0); 3,3333 (28,8); 2,8928 (0,7); 2,7340 (0,6); 2,7328 (0,5); 2,5218 (0,3); 2,5132 (4,8); 2,5087 (9,7); 2,5041 (12,8); 2,4995 (9,2); 2,4950 (4,4); 1,2167 (0,3); 1,2131 (0,4); 1,2048 (0,6); 1,2014 (0,5); 1,1929 (0,7); 1,1811 (0,6); 1,1732 (0,4); 1,1692 (0,4); 1,1609 (0,3); 0,6365 (0,5); 0,6265 (0,6); 0,6237 (0,6); 0,6154 (0,6); 0,6132 (0,6); 0,6062 (0,4); 0,6018 (0,4); 0,5916 (0,5); 0,5795 (0,4); 0,5762 (0,5); 0,5662 (0,6); 0,5564 (0,6); 0,5461 (0,6); 0,4799 (0,5); 0,4682 (0,7); 0,4560 (0,9); 0,4455 (0,7); 0,3902 (0,4); 0,3782 (0,6); 0,3673 (0,8); 0,3552 (0,7); 0,3428 (0,4) XVIc.04: 1H-RMN(300,2 MHz, CDCl3): δ= 7,3126 (10,3); 7,2989 (6,2); 6,7720 (1,8); 5,3370 (0,8); 4,2375 (2,4); 4,2137 (7,4); 4,1899 (7,5); 4,1662 (2,4); 1,7013 (1,9); 1,6845 (5,2); 1,6738 (5,4); 1,6584 (2,3); 1,6307 (5,4); 1,3234 (2,6); 1,3080 (5,9); 1,2938 (10,0); 1,2805 (2,6); 1,2700 (16,0); 1,2462 (7,6); 0,0350 (7,0)
XVIc.05: 1H-RMN(300,2 MHz, d6-DMSO): δ= 9,0979 (3,5); 9,0743 (3,6); 8,0601 (16,0); 3,6943 (2,8); 3,6707 (3,0); 3,6633 (3,2); 3,6397 (2,8); 2,5334 (0,8); 2,5278 (1,8); 2,5218 (2,5); 2,5159 (1,8); 2,0931 (0,9); 1,2461 (0,7); 1,2313 (0,9); 1,2187 (1,5); 1,2039 (1,5); 1,1887 (1,5); 1,1733 (0,9); 1,1618 (0,8); 1,1457 (0,4); 0,6745 (0,5); 0,6651 (0,6); 0,6594 (0,7); 0,6477 (1,4); 0,6394 (1,3); 0,6307 (1,6); 0,6187 (2,0); 0,6025 (1,0); 0,5905 (1,3); 0,5855 (1,1); 0,5676 (1,3); 0,5551 (1,8); 0,5404 (1,6); 0,5287 (2,3); 0,5188 (1,3); 0,5055 (1,8); 0,5005 (1,7); 0,4921 (2,0); 0,4753 (2,3); 0,4621 (1,7); 0,4456 (0,7); 0,3967 (0,9); 0,3811 (1,6); 0,3672 (2,0); 0,3507 (1,9); 0,3388 (1,1); 0,0114 (1,3) XVIc.06: 1H-RMN(300,2 MHz, d6-DMSO): δ= 12,6058 (0,4); 9,2124 (7,5); 7,8263 (16,0); 3,3584 (1,5); 2,5282 (4,5); 2,5223 (6,0); 2,5164 (4,5); 2,0945 (0,8); 1,4547 (2,9); 1,4388 (7,3); 1,4281 (8,1); 1,4141 (3,6); 1,3612 (0,3); 1,1423 (3,6); 1,1282 (7,8); 1,1174 (7,5); 1,1015 (2,8); 0,0173 (2,2) XVIIc.01: 1H-RMN(300,2 MHz, CDCl3): δ= 7,2985 (0,9); 6,2968 (2,9); 5,8790 (3,7); 4,2235 (2,2); 4,1997 (6,7); 4,1760 (6,8); 4,1523 (2,2); 2,0305 (0,4); 1,6536 (1,9); 1,6373 (5,4); 1,6265 (5,6); 1,6115 (2,3); 1,2774 (7,2); 1,2538 (16,0); 1,2401 (6,2); 1,2298 (12,0); 1,2129 (2,1); 0,0202 (0,8) XVIIIc.01: 1H-RMN(300,2 MHz, CDCl3): δ= 7,3430 (0,4); 7,2989 (4,6); 6,7348 (0,4); 4,2303 (0,5); 4,2066 (1,5); 4,1828 (1,6); 4,1591 (0,5); 1,6856 (0,4); 1,6690 (1,2); 1,6582 (1,2); 1,6430 (0,6); 1,6095 (2,7); 1,5410 (16,0); 1,2930 (2,2); 1,2790 (1,3); 1,2691 (4,4); 1,2514 (0,6); 1,2454 (1,6); 0,0368 (5,5)
XIXc.01: 1H-RMN(300,2 MHz, d6-DMSO): δ= 13,4605 (1,6); 13,3786 (1,6); 13,2747 (2,0); 13,2607 (2,1); 13,2418 (2,4); 13,1976 (2,6); 13,1780 (2,4); 13,1651 (2,6); 13,0998 (2,9); 13,0936 (2,9); 13,0821 (3,0); 13,0381 (3,2); 12,9902 (3,5); 12,9696 (3,4); 12,9563 (3,4); 12,9261 (3,3); 12,9166 (3,1); 12,9040 (3,3); 12,8582 (3,1); 12,8359 (3,4); 12,8242 (3,0); 12,7876 (2,7); 12,6640 (2,0); 12,5368 (1,6); 12,5068 (1,6); 12,4811 (1,6); 7,1025 (1,6); 7,0457 (2,2); 7,0074 (2,0); 6,9258 (3,4); 6,8352 (5,3); 6,6472 (16,0); 6,5167 (6,9); 6,4124 (2,9); 6,3341 (1,8); 6,1823 (1,6); 3,9925 (1,7); 3,8936 (1,8); 3,7735 (1,8); 3,7667 (1,6); 3,6496 (2,9); 3,3680 (566,0); 3,2044 (4,4); 3,0765 (1,6); 3,0065 (1,9); 2,9799 (1,6); 2,7531 (2,5); 2,5392 (262,9); 2,5339 (326,0); 2,3041 (2,0); 1,2671 (1,7); 0,2259 (1,9); 0,0305 (246,1); -0,0116 (1,7); -1,0984 (1,8)
DADOS BIOLÓGICOS Exemplo A: teste celular in vitro de Xanthomonas campestris pv. campestris Solvente: DMSO Meio de cultura: Meio de caldo LB (Luria Broth Miller) Sigma Inóculo: suspensão de bactéria
[00191] Os compostos a serem testados foram solubilizados em DMSO e a solução utilizada para preparar a faixa de concentração necessária. A concentração final de DMSO usada no ensaio foi de ≤ 1%.
[00192] O inóculo foi preparado a partir de uma pré-cultura de bactérias cultivadas em meio líquido e diluídas até a densidade óptica (DO) desejada.
[00193] Os compostos foram avaliados quanto à sua capacidade de inibir o crescimento de bactérias em ensaio de cultura líquida. Os compostos foram adicionados nas concentrações desejadas ao meio de cultura contendo a suspensão de bactérias. Após 24h de incubação, a eficácia dos compostos foi determinada por medição espectrométrica de crescimento bacteriano. A inibição foi determinada comparando os valores de absorbância em cavidades contendo os compostos com a absorbância em cavidades de controle sem compostos.
[00194] Nesse teste, os seguintes compostos de acordo com a invenção não mostraram atividade direta a uma concentração de 20 ppm do composto testado: II.01; II.02; II.03; II.04; II.06; II.07; II.08; II.09; II.10; II.11; II.12; II.13; II.14; II.15; II.16; II.17; II.18; II.19; II.20; II.21; II.22; II.23; II.24; II.35; II.36. Exemplo B: Teste preventivo in vivo em Xanthomonas campestris pv. campestris (podridão negra no repolho)
[00195] Os compostos testados foram preparados por homogeneização em uma mistura de acetona/dimetil sulfóxido/tween® e, em seguida, diluídos com água para obter a concentração desejada.
[00196] As mudas de repolho foram tratadas por pulverização do composto preparado conforme descrito acima. Plantas de controle foram tratadas apenas com solução aquosa de acetona/dimetil sulfóxido/tween®.
[00197] Após 72 horas, as plantas foram contaminadas por pulverização das folhas com uma suspensão aquosa de bactéria de Xanthomonas campestris pv. campestris. As plantas de repolho contaminadas foram incubadas por 8 ou 10 dias a 27ºC e 95% de umidade relativa.
[00198] O teste foi avaliado 8 ou 10 dias após a inoculação. 0% significa uma eficácia que corresponde à das plantas de controle, enquanto uma eficácia de 100% significa que nenhuma doença foi observada.
[00199] Nesse teste, os seguintes compostos de acordo com a invenção mostraram eficácia entre 70% e 79% a uma concentração de 31 ppm do composto testado: II.02; II.31; II.35.
[00200] Nesse teste, os seguintes compostos de acordo com a invenção mostraram eficácia entre 80% e 89% a uma concentração de
31 ppm do composto testado: II.03; II.04; II.15.
[00201] Nesse teste, os seguintes compostos de acordo com a invenção mostraram eficácia entre 90% e 100% a uma concentração de 31 ppm do composto testado: II.01; II.06; II.14; II.36. Exemplo C: exemplos comparativos
[00202] Os compostos CMP1 e CMP2 foram testados em um teste preventivo in vivo em Xanthomonas campestris pv. campestris (podridão negra em repolho) nas mesmas condições descritas no Exemplo B.
[00203] Os compostos CMP1 e CMP2 foram preparados de acordo com os ensinamentos da US 5.534.541.
[00204] Os resultados são conforme mostrados na tabela abaixo.
Eficácia Ex. R1 R2 R3 R4 R5 R6 (%) CMP1 Br Br Br H H Me 27 II.01 Cl Cl Cl H H Me >90 CMP2* Cl Cl Cl isopropila H Me 0 II.01 Cl Cl Cl H H Me >90 ciclopropil II.06 Cl Cl Cl H Me >90 a II.14 Cl Cl Cl butan-2-ila H Me >90 II.36 Cl Cl Cl -CH2-CH(CH=CH2)- Me >90 * (S) enantiômero Exemplo D: Indução de expressão gênica de defesa em Arabidopsis thaliana
[00205] Plantas repórter de Arabidopsis thaliana contendo a sequência de codificação de uma proteína fluorescente verde (GFP)
ligada à sequência promotora responsiva a salicilato do gene PR1 (proteína relacionada à patogênese I) (AT2G14610) foram cultivadas por cinco dias e, em seguida, pulverizadas com compostos. No terceiro dia após a pulverização, a fluorescência da planta foi avaliada com um instrumento MacroFluo da Leica Microsystems (Wetzlar, Alemanha). As fluorescências foram quantificadas com o software Meta-Morph Microscopy Automation & Image Analysis (Molecular Devices, Sunnyvale, Califórnia, Estados Unidos).
[00206] A fluorescência de fundo em folhas falsamente tratadas foi definida como 1,00. O tratamento com ácido salicílico (300ppm) resultou em um valor relativo de fluorescência de 2,70, comprovando a validade do sistema de teste.
[00207] Nesse teste, os seguintes compostos de acordo com a invenção apresentaram um valor de fluorescência relativa pelo menos superior a 2 a uma concentração de 300 ppm do composto: II.01; II.02; II.03; II.04; II.05; II.07; II.08; II.09; II.10; II.11; II.12; II.13; II.14; II.15; II.17; II.18; II.19; II.20; II.22; II.23; II.24; II.25; II.26; II.30; II.31; II.32; II.33; II.35; II.36; II.37.
[00208] Nesse teste, os seguintes compostos de acordo com a invenção apresentaram um valor de fluorescência relativa pelo menos superior a 2 a uma concentração de 75 ppm do composto: II.16; II.28.
[00209] O salicilato é um dos principais hormônios de defesa contra patógenos de plantas. Todos os compostos descritos acima estimulam a via do ácido salicílico e, portanto, podem proteger as plantas contra uma ampla gama de patógenos.
Claims (17)
1. Composto, caracterizado pelo fato de que que apresenta a Fórmula (II): (II) em que R1, R2 e R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6- alquenila, C2-C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6- alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; R7 é um átomo de hidrogênio ou uma C1-C6-alquila.
2. Composto de Fórmula (II), de acordo com a reivindicação 1, caracterizado pelo fato de que R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1- C6-cianoalquila, C2-C6-alquenila, C2-C6-alquinila, ciclopropila, fenila, benzila, -C1-C6-alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil-ciclopropila.
3. Composto de Fórmula (II), de acordo com a reivindicação 1 ou 2, caracterizado pelo fato de que R7 é um átomo de hidrogênio ou uma metila.
4. Composto de Fórmula (II), de acordo com qualquer uma das reivindicações 1 a 3, caracterizado pelo fato de que R4 é um átomo de hidrogênio ou isobutila.
5. Composto de Fórmula (II), de acordo com qualquer uma das reivindicações 1 a 3, caracterizado pelo fato de que R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila.
6. Composição, caracterizada pelo fato de que compreende pelo menos um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, e pelo menos um auxiliar agricolamente adequado.
7. Método para controlar doenças bacterianas, caracterizado pelo fato de que compreende a etapa de aplicar pelo menos um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, ou uma composição, como definida na reivindicação 6, às plantas, partes de plantas, sementes, frutos ou ao solo em que as plantas crescem.
8. Processo para preparar um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, caracterizado pelo fato de que compreende a etapa de reagir um composto de Fórmula (XIV) ou um sal do mesmo com um composto de Fórmula (XV) ou um sal do mesmo: (XIV) (XV) (II) em que R1, R2, R3, R4, R5, R6 e R7 são como definidos em qualquer uma das reivindicações 1 a 5; U1 é um átomo de halogênio, um grupo hidróxi ou um grupo C1-C6-alcóxi.
9. Processo para preparar um composto de Fórmula (II),
como definido em qualquer uma das reivindicações 1 a 5, caracterizado pelo fato de que compreende a etapa de realizar uma reação de cloração em um composto de Fórmula (XVI) (XVI) (II) em que R1, R2, R3, R4, R5, R6 e R7 são como citados nas reivindicações 1 a 5; U10, U11 e U12 são independentemente um átomo de hidrogênio ou um átomo de cloro; desde que pelo menos um de U10, U11 ou U12 seja um átomo de hidrogênio.
10. Processo para preparar um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, caracterizado pelo fato de que compreende a etapa de realizar uma diazotação de um composto de Fórmula (XVII) ou um sal do mesmo seguido por uma substituição aromática: (XVII) (II) em que R1, R2, R3, R4, R5, R6 e R7 são como citados nas reivindicações 1 a 5; U13, U14 e U15 são independentemente um grupo amino ou um átomo de cloro; desde que pelo menos um de U13, U14 ou U15 seja um grupo amino.
11. Composto, caracterizado pelo fato de que apresenta a Fórmula (XVIa) ou (XVIb): (XVIa) (XVIb) em que R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6- alquenila, C2-C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6- alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila.
12. Composto, caracterizado pelo fato de que apresenta a Fórmula (XVIc): (XVIc) em que R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6- alquenila, C2-C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6- alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; desde que o composto de Fórmula (XVIc) exclua: - N-[(4,5-dicloro-2-tienil)carbonil]glicina [138326-45-1], - N-[(4,5-dicloro-2-tienil)carbonil]isoleucina [138326-47-3], - N-[(4,5-dicloro-2-tienil)carbonil]leucina [138326-54-2], - N-[(4,5-dicloro-2-tienil)carbonil]leucinato de metila [138326- 32-6], - N-[(4,5-dicloro-2-tienil)carbonil]isoleucinato de metila [138326-33-7], - N-[(4,5-dicloro-2-tienil)carbonil]valinato de 2,2,2- trifluoroetila [138326-35-9], - N-[(4,5-dicloro-2-tienil)carbonil]leucinato de 2,2,2- trifluoroetila [138326-36-0], e - N-[(4,5-dicloro-2-tienil)carbonil]isoleucinato de 2,2,2- trifluoroetila [138326-37-1].
13. Composto, caracterizado pelo fato de que apresenta a Fórmula (XVIIa), (XVIIb) ou (XVIIc): (XVIIa) (XVIIb) (XVIIc) em que
R1, R2, R3 são um átomo de cloro; R4 é selecionado do grupo que consiste em átomo de hidrogênio, 2-metilpropila, 1-metilpropila, ciclopropila, ciclopropila substituída por C2-C6-alquenila, aralquila e aralquila substituída por hidroxila, e R5 é um átomo de hidrogênio; ou R4 e R5 formam, juntamente com o átomo de carbono ao qual estão ligados, uma ciclopropila; R6 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, C1-C6-haloalquila, C1-C6-cianoalquila, C2-C6- alquenila, C2-C6-alquinila, C3-C8-cicloalquila, arila, aralquila, -C1-C6- alquil-Si(C1-C6-alquil)3 e -C1-C6-alquil- C3-C8-cicloalquila; R4 é selecionado do grupo que consiste em átomo de hidrogênio, C1-C6-alquila, aralquila, aralquila substituída por hidroxila, C1-C6-alquila substituída por C1-C6-alquilsulfanila e R5 é um átomo de hidrogênio quando R6 é átomo de hidrogênio ou C1-C6-alquila.
14. Uso de um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, ou de uma composição, como definida na reivindicação 6, caracterizado pelo fato de que é para controlar doenças bacterianas em plantas, partes de plantas, sementes, frutos ou no solo em que as plantas crescem.
15. Uso de um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, caracterizado pelo fato de que é para preparar uma composição para controlar doenças bacterianas em plantas, partes de plantas, sementes, frutos ou no solo em que as plantas crescem.
16. Plantas, partes de plantas, frutos e/ou sementes resistentes a bactérias, caracterizadas de que compreendem plantas, partes de plantas, frutos e/ou sementes revestidas com um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, ou com uma composição, como definida na reivindicação 6.
17. Combinação, caracterizada pelo fato de que compreende um composto de Fórmula (II), como definido em qualquer uma das reivindicações 1 a 5, ou com uma composição, como definida na reivindicação 6, com outros ingredientes ativos selecionados entre fungicidas, bactericidas, acaricidas, nematicidas, inseticidas, herbicidas, fertilizantes, reguladores de crescimento, protetores e/ou semiquímicos.
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