BRPI1011796B1 - composição fungicida agrícola ou hortícola compreendendo ciazofamida e folpet como ingredientes ativos, e, método para o controle de um patógeno de planta com a dita composição - Google Patents
composição fungicida agrícola ou hortícola compreendendo ciazofamida e folpet como ingredientes ativos, e, método para o controle de um patógeno de planta com a dita composição Download PDFInfo
- Publication number
- BRPI1011796B1 BRPI1011796B1 BRPI1011796A BRPI1011796A BRPI1011796B1 BR PI1011796 B1 BRPI1011796 B1 BR PI1011796B1 BR PI1011796 A BRPI1011796 A BR PI1011796A BR PI1011796 A BRPI1011796 A BR PI1011796A BR PI1011796 B1 BRPI1011796 B1 BR PI1011796B1
- Authority
- BR
- Brazil
- Prior art keywords
- compounds
- composition
- folpet
- methyl
- agricultural
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 43
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000005789 Folpet Substances 0.000 title claims abstract description 23
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 18
- 239000004480 active ingredient Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 10
- 244000000003 plant pathogen Species 0.000 title claims abstract description 5
- 239000002689 soil Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 abstract description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 2
- -1 imidazole compound Chemical class 0.000 description 62
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 230000001276 controlling effect Effects 0.000 description 11
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 10
- 239000005740 Boscalid Substances 0.000 description 9
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 9
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 241000233679 Peronosporaceae Species 0.000 description 2
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- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 2
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- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 2
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 2
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- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 2
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 description 2
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- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
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- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
composição fungicida agrícola ou hortícola compreendendo ciazofamida e folpet como ingredientes ativos, e, método para o controle de um patógeno de planta com a dita composição. a presente invenção provê uma composição na qual o efeito fungicida contra culturas infectadas por um fitopatógeno é altamente estável e efetiva. uma excelente composição fungicida agrícola ou hortícola para o controle de um fitopatógeno é provida pelo uso de (a) ao menos um composto imidazólico representado pela fórmula (1): em que r representa um grupo alquila c1-6 ou um grupo alcóxi c1-6; e n representa um número inteiro entre 1 a 5, e (b) o folpet, como ingredientes ativos; por combinação em comparação com o uso isolado de cada composto, e um fitopatógeno é assim controlado.
Description
Relatório Descritivo da Patente de Invenção para: “COMPOSIÇÃO FUNGICIDA AGRÍCOLA OU HORTÍCOLA COMPREENDENDO CIAZOFAMIDA E FOLPET COMO INGREDIENTES ATIVOS, E, MÉTODO PARA O CONTROLE DE UM PATÓGENO DE PLANTA COM A DITA COMPOSIÇÃO”.
ÁREA TÉCNICA [001] A presente invenção se refere a uma composição fungicida agrícola ou hortícola em que o controle efetivo contra um patógeno, especialmente a prevenção e/ou efeito terapêutico contra um fitopatógeno (ou patógeno de planta), é aumentado de forma acentuada; e a um método para o controle de um fitopatógeno.
ANTECEDENTES DA INVENÇÃO [002] A literatura de patente 1 descreve que os compostos imidazólicos, um dos ingredientes ativos de composições fungicidas agrícolas e hortícolas da presente invenção, são empregados como agentes de controle de organismos biológicos nocivos. Além disso, também é descrito que quando necessário, a composição pode ser misturada com ou usada de forma combinada com outros fungicidas, como por exemplo, a N-(tricloro-metil-sulfenil) ftalimida. Entretanto, a literatura de patente 1 não descreve em nenhum documento específico o uso de compostos imidazólicos misturados com o composto acima descrito.
[003] A literatura de patente 2 descreve o folpet como fungicida agrícola ou hortícola.
[004] Lista de citações.
[005] Literatura de Patente.
[006] Literatura de patente 1: Pedido de patente japonês não examinado n°
1989-131163.
[007] Literatura de patente 2: patente norte-americana US 2 553 770.
SUMÁRIO DA INVENÇÃO
Problema técnico [008] Como os compostos imidazólicos representados pela fórmula (I), a seguir, são ligeiramente ineficazes no controle efetivo de certos fitopatógenos específicos ou apresentam eficácia relativamente baixa, eles
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2/16 praticamente não exibem um efeito controlador eficaz contra fitopatógeno em certas condições de aplicação.
Solução do problema [009] Como resultado das pesquisas visando a solucionar o problema acima descrito, a presente invenção observa que o uso de um composto imidazólico representado pela formula (I), a seguir, em combinação com o folpet apresenta um efeito não previsível e um excelente controle contra fitopatógenos quando comparada com o uso de cada um destes componentes isoladamente, completando assim a invenção. DESCRIÇÃO DETALHADA DA INVENÇÃO [010] A presente invenção descreve uma composição fungicida agrícola e hortícola compreendendo:
[011] (a) pelo menos um composto imidazólico representado pela fórmula (I):
SOiN(CH3)2 φ [012] em que R representa um grupo alquila C1-6 ou um grupo alcóxi
C1-6; e n representa um número inteiro entre 1 a 5, e [013] (b) o folpet, como ingredientes ativos.
[014] A presente invenção descreve ainda um método de controle de um fitopatógeno, compreendendo a aplicação da composição acima descrita na planta ou no solo. Além disso, a presente invenção descreve um método de controle de um fitopatógeno, que compreende a aplicação de uma quantidade efetiva de (a) pelo menos um composto imidazólico representado
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3/16 pela formula (I) e uma quantidade efetiva do (b) folpet a uma planta ou ao solo.
[015] Na formula (I), o grupo alquila C1-6 ou a fração alquila do grupo alcóxi C1-6 como representado em R incluem um grupo alquila contendo de 1 a 6 átomos de carbono, tal como metila, etila, propila, butila, pentila ou hexila, que tanto pode conter cadeia aberta ou cadeia fechada. Quando n é 2 ou maior que 2, os grupos R plurais podem ser iguais ou diferentes.
[016] Exemplos de compostos imidazólicos representados pela formula (I) incluem os seguintes compostos:
[017] 4 -cloro-2-ciano-1 -dimetil-sulfamoil-5-(4-metil-fenil) imidazol (composto N° 1);
[018] 4-cloro-2-ciano-1 -dimetil-sulfamoil-5-(4-metóxi-fenil) imidazol (composto N° 2);
[019] 4-cloro-2-ciano-1-dimetil-sulfamoil-5-(4-etil-fenil) imidazol (composto N° 3);
[020] 4-cloro-2-ciano-1-dimetil-sulfamoil-5-(3-metil-4-metóxi-fenil) imidazol (composto N° 4);
[021] Além disso, o composto n° 1 é conhecido como ciazofamida, em se tratando de nome comum.
[022] O folpet que é usado como o ingrediente ativo (b) da presente invenção é o N-tricloro-metano-sulfenil-ftalimida.
[023] Como a composição fungicida agrícola ou hortícola compreendendo (a) pelo menos um composto selecionado dentre os compostos imidazólicos, representados pela fórmula (I), e (b) pelo folpet, como ingredientes ativos (doravante chamada de composição da presente invenção) exibe uma excelente atividade fungicida pela aplicação em uma plantas cultivadas, como, por exemplo, vegetais, tais como pepinos, tomates, e berinjelas; cereais, tais como, arroz e trigo; ervilhas; árvores frutíferas, tais como, de maçãs, peras, uvas, e citrinos; e batatas, as quais estão infectadas ou têm a possibilidade de serem infectadas por um
Petição 870170014049, de 03/03/2017, pág. 14/70
4/16 patógeno prejudicial, é desejável para controlar doenças como o oídio, míldio, antracnose, mofo cinzento, fungo verde comum, sarna, doença da mancha, crestamento bacteriano, mancha negra, doença da mancha preta, podridão noturna, ferrugem ou requeima, mancha do anel, ferrugem, queima da bainha, tombamento de mudas e murcha de esclerócio. Além disso, a composição da presente invenção exibe um excelente efeito controlador contra doenças de solo causadas por fitopatógenos, tais como, Fusarium, Rhizoctonia, Verticillium, Purazumodiohora, Pythium. A composição da presente invenção apresenta um efeito residual longo e efetivo, e, especialmente, um excelente efeito preventivo.
[024] A composição da presente invenção apresenta efeito controlador contra doenças, tais como, brusone, queima das bainhas do arroz, antracnose do pepino, míldio em pepinos, melões, repolho, repolho chinês, cebolas, abóboras, uvas, oídio do trigo, cevada, pepino, ferrugens da batata, pimenta vermelha, pimentões, melancias, abóboras, tabaco, tomates; septoriose do trigo; mancha do anel no tomate; melanose cítrica; fungo verde comum de cítricos; sarna da pera; mancha púrpura na maçã; ponteira branca da cebola, míldio da melancia; diversos fungos cinza; diversas ferrugens da folha; diversas ferrugens; diversas manchas bacterianas, e diversas doenças transmitidas pelo solo e causadas por fungos fitopatogênicos, tais como, Fusarium, Pythium, Rhizoctonia e Verticillium. Além disso, a composição da presente invenção apresenta um excelente efeito controlador contra doenças causadas por Plasmodiophora. Mais especificamente, a composição desta invenção exibe um efeito controlador especialmente eficaz contra doenças, tais como, ferrugens da batata, pimenta vermelha, pimentões, melancias, abóboras, tabaco, tomates; míldio de pepino, melão, repolho, repolho chinês, cebola, abóboras, uvas e doenças causadas por Pythium, queima provocada por bactéria e queima da folha (manchas marrons e manchas largas) da grama.
[025] Os ingredientes ativos que constituem a composição da presente invenção podem ser formulados de diversas formas, tais como,
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5/16 concentrados emulsificáveis, pós polvilháveis, pós molháveis, concentrados solúveis, grânulos, suspensões concentradas, etc., em conjunto com diversos adjuvantes, como em preparações agrícolas convencionais. Os ingredientes ativos (a) são selecionados de compostos imidazólicos contendo a formula (I), e (b) folpet, e outros compostos específicos podem ser misturados e formulados, e cada um deles pode ser preparado separadamente e posteriormente misturado. Conforme a utilização, a preparação pode ser usada conforme obtida ou diluída com diluentes apropriados, como, por exemplo, água, até uma concentração predeterminada. Os exemplos de adjuvantes que podem ser empregados incluem veículos, agentes emulsificantes, agentes de suspensão, espessantes, estabilizantes, dispersantes, agentes de espalhamento, agentes umectantes, agentes penetrantes, agentes anticongelantes, agentes antiespumantes, e semelhantes. Estes adjuvantes são adicionados apropriadamente, caso necessário. Os veículos podem ser veículos sólidos e veículos líquidos. Os veículos sólidos podem incluir pós de origem animal e vegetal (por exemplo, amido, açúcar, celulose em pó, serragem, farinha de peixe, leite em pó, etc.); pós minerais (por exemplo, talco, caulim, bentonita, bentonita orgânica, carbonato de cálcio, sulfato de cálcio, hidrogenato de sódio, zeolita, terras diatomáceas, carbono branco, argila, alumina, sílica, enxofre em pó, cal apagada, etc.); e semelhantes. Os exemplos de veículos líquidos incluem água, óleos vegetais (por exemplo, óleo de soja, óleo de semente de algodão), óleos animais (por exemplo, sebo bovino, óleo de baleia, etc.), álcoois (por exemplo, álcool etílico, etileno glicol, etc.), cetonas (por exemplo, acetona, metil-etil-cetona, metil-isobutil-cetona, isoforona, etc.), éteres (por exemplo, dioxano, tetra-hidrofurano, etc.), hidrocarbonetos alifáticos (por exemplo, querosene, óleo de querosene, parafina líquida, etc.), hidrocarbonetos aromáticos (por exemplo, tolueno, xileno, trimetilbenzeno, tetrametil-benzeno, ciclo-hexano, nafta solvente, etc.), hidrocarbonetos halogenados (por exemplo, clorofórmio, cloro-benzeno, etc.), amidas ácidas (por exemplo, N-metil-2-pirolidona, N,N
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6/16 dimetilformamida, Ν,Ν-dimetil-acetamida, etc.), ésteres (por exemplo, acetato de etila, ácidos graxos de ésteres de glicerina, etc.), nitrilas (por exemplo, acetonitrila, etc.), compostos contendo enxofre (por exemplo, dimetil-sulfóxido, etc.), e semelhantes. Os exemplos de dispersantes incluem alquil-sulfato de sódio, alquil-benzeno sulfato de sódio, sulfonato de lignina sódica, polioxietileno alquil-glicol-éter, polioxietileno lauril-éter, polioxietileno alquil-aril-éter, éster de sorbitano polioxietileno de ácido graxo, e semelhantes.
[026] Além disso, a composição da presente invenção pode ser misturada a outros agroquímicos, tais como, um fungicida, um inseticida, um acaricida, um nematocida, um pesticida para insetos de solo, um agente antivírus, um agente de atração, um herbicida, um agente regulador do crescimento vegetal, e neste caso, excelentes resultados posteriores são apresentados em certas ocasiões.
[027] Quando o composto do ingrediente ativo do fungicida é o outro agroquímico acima mencionado, podem ser incluídos, por exemplo, (por nomes comuns e alguns deles estão ainda em fase de análise, ou teste pela Associação Japonesa para proteção a Vegetais):
[028] compostos anilino-pirimidínicos, tais como, mepanipirim, pirimetanil, e ciprodinil; um composto triazoropirimidinico, tal como, 5-cloro-7(4-metil-piperidin-1-il)- 6-(2,4,6-triflúor-fenil) [1,2,4] triazol [1,5-a] pirimidina;
[029] compostos piridinaminicos , tal como, fluazinam;
[030] azo compostos, tais como, triadimefona, bitertanol, triflumizol, etaconazol, propiconazol, penconazol, flusilazol, miclobutanil, ciproconazol, tebuconazol, hexaconazol, cis-furconazol, proclorazol, metconazol, epoxiconazol, tetraconazol, fumarato de oxpoconazol, sipconazol, protioconazol, triadimenol, flutriafol, difenoconazol, fluquinconazol, fenbuconazol, bromuconazol, diniconazol, triciclazol, probenazol, simeconazol, pefurazoato, ipconazol e imibenconazol;
[031] compostos quinoxalinícos, tal como, quinometionato;
[032] compostos de ditiocarbamato, tais como, maneb, zineb,
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7/16 mancozeb, polycarbamato, metiram, propineb e tiram;
[033] compostos orgânicos de cloro, tais como, ftalida, clorotalonila e quintozeno;
[034] compostos imidazólicos, tais como, benomil, metil-tiofanato, carbendazim, tiabendazol e fuberiazol;
[035] compostos cianoacetamidicos, tal como, cimoxanil;
[036] compostos de anilida, tais como, metalaxila, M-metalaxila, mefenoxam, oxadixil, ofurace, benalaxil, M- benalaxl (outros nomes: quiralaxil, ciralaxil), furalaxil, ciprofuram, carboxina, oxicarboxina, tifluzamida, boscalid, bixafen, isotianil, tiadinil e sedaxane;
[037] compostos de sulfamida, tal como, diclofluanida;
[038] compostos de cobre, tais como, hidróxido de cobre e cobre oxina;
[039] compostos isoxazolicos, tal como himexazol;
[040] compostos organofosforados, tais como fosetil-AI, metiltolclofos, S-benzil-0,0-di-isopropil-fosforo-tioato, O-etil-S,S-difenil-fosforoditioato, alumínio etil-hidrogênio fosfonato, edifenfos.e iprobenfos;
[041] compostos ftalimídicos, tais como, captan e captafol;
[042] compostos de dicarboximida, tais como, procimidona, iprodiona e vinclozolina;
[043] compostos de benzanitida, tais como flutolanil e mepronil;
[044] compostos de amida, tais como pentiopirad, uma mistura de 3(diflúor-metil)-1-metil-N[(1 RS,4SR,9SR)-1,2,3,4-tetra-hidro-9-isopropil-1,4metano-naftalen-5-il]pirazol-4-carboxamida e 3-(d ifl úor-meti l)-1 -metil-N[(1 RS,4SR,9SR)-1,2,3,4-tetra-hidro-9-isopropil-1,4-metano-naftalen-5-il] pirazol-4-carboxainida (isopirazam), siltiofam e fenoxanil;
[045] compostos de benzamida, tais como, fluopiram e zoxamida;
[046] compostos piperazínicos, tal como, triforina;
[047] compostos de piridina, tal como, pirifenox;
[048] compostos de carbinol, tal como fenarimol;
[049] compostos de piperidina, tal como fenpropidina;
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8/16 [050] compostos morfolínicos, tais como fenpropimorfe e tridemorfe;
[051] compostos de organotina, tais como, hidróxido de fentina e acetato de fentina;
[052] compostos de ureia, tal como, pencicuron;
[053] compostos do ácido cinâmico, tais como, dimetomorfe e flumorfe;
[054] compostos de fenil-carbamato, tal como, dietofencarb;
[055] compostos de cianopirrol, tal como, fludioxonila e fenpiclonil;
[056] compostos de estrobilurina, tais como, azoxistrobina, metilcresoxima, metomino-estrobina, trifloxistrobina, picoxistrobina, orizastrobina, dimoxistrobina, piraclostrobina, e fluoxastrobina;
[057] compostos de oxazolidinona, tal como, famoxadona;
[058] compostos de tiazol-carboxamida, tal como, etaboxame;
[059] compostos de valinamida, tais como, iprovalicarb e isopropilbentiavalicarb;
[060] compostos de ácido acilamino, tais como, metil N(isopropoxicarbonil)-L-valil-(3RS)-3‘(4-clorofenil)-p-alaninato (valifenalato);
[061] compostos de imidazolinona, tais como, fenamidona;
[062] compostos de hidroxianilida, tais como fen-hexamida;
[063] compostos de benzeno-sulfonamida, tal como, flusulfamida;
[064] compostos de éter de oxima, tal como, ciflufenamida;
[065] compostos de antraquinona;
[066] compostos crotônicos; antibióticos, tais como, validamicina, casugamicina e polioxinas;
[067] compostos de guanidina, tais como, iminoctadina e dodina;
[068] compostos de quinolina, tais como, acetato de 6-tert-butil-Sfluoro-2,3-dimetil-quinolin-4il (tebufloquina);
[069] compostos de tiazolidina, tais como, (z)-2-(2-flúr-5-(triflúormetil) feniltio)-2-(3-(2-metóxi-fenil) tiazolidin-2-ilideno) acetonitrila (flutianil); e [070] outros compostos tais como, piribencarb, isoprotiolano, piroquilona, diclomezina, quinoxifen, hidrocloreto de propamocarb,
Petição 870170014049, de 03/03/2017, pág. 19/70
9/16 cloropicrina, dazomet, metam-sódio, nicobifen, metrafenona, UBF-307, diciocimet, proquinazida, amisulbrom (outro nome: amibromdol), 3-(2,3,4trimetóxi-6-metil-benzoil)-5-cloro-2- metóxi-4-metil-piridina, 4-(2,3,4-trimetóxi6-metil-benzoil)-2,5-dicloro-3- triflúor-metil-piridina, 4-(2,3,4-trimetóxi-6-metilbenzoil)-2-cloro-3-triflúor-metil-S-metóxi-piridina, mandipropamida, fluopicolida, carpropamida, meptil-dinocap, N-[(3', 4'-dicoloro-1,1-dimetil) fenacil]-3-triflúor-meti-2-piridina carboxamida, N-[(3', 4'-dicloro-1,1-dimetil) fenacil]-3-metil-2-tiofeno carboxamida, N-[(3', 4-dicloro-1,1-dimetil) fenacil]-1metil-3-triflúor-meti-4- 5 pirazol carboxamida, N-[[2,-metil-4,-(2-propiloxi)-1,1dimetil] fenacil]-3- triflúor-metil-2-piridina carboxamida, N-[[2-metil-4'-(2propilóxi)-1,1 - dimetil] fenacil-3-metil-2-tiofeno carboxamida, N-[[2'-metil-4'(2-propilóxi)-1,1 l-dimetil] fenacil]-1-metil-3-triflúor-metil-4-pirazol carboxamida, N-[[4'-(2-propilóxi)-1,1 -dimetil] fenacil]-3-triflúor-meti-2-piridina carboxamida, N-[[4'-(2-propilóxi)-1,1 -dimetil]f enacil]-3-metil-2-tiofeno carboxamida, N-[[4’-(2-propilóxi)-1,1-dimetil] fenacil]-1 -metil-3-triflúor-metil4-pirazol carboxamida, N-[[2'-metil-4'-(2-pentilóxi)-1,1 -dimetil] fenacil]-3triflúormeti-2-piridina carboxamida, N-[[4'-(2-pentilóxi)-1,1 -dimetil] fenacil]-3triflúor-meti-2-piridina carboxamida, ferimzona, espiroxamina, S-2188, (fenpirazamina), S-2200, ZF-9646, BCF-051, BCM-061 e BCM-062.
[071] Os ingredientes ativos compostos de um agente de controle de pragas de insetos, tais como, o inseticida, o acaricida, o nematicida, ou os pesticidas de insetos do solo dentre os outros agroquímicos acima mencionados, incluem, por exemplo, (por nomes comuns e alguns deles estão ainda em fase de análise, ou teste pela Associação Japonesa para proteção a Vegetais):
[072] compostos de fosfato orgânico, tais como, profenofos, diclorvos, fenamifos, fenitrotiona, EPN, diazinon, clorpirifos, metil-clorpirifos, acefato, protiofos, fostiazato, cadusafos, dislufoton, isoxation, isofenfos, etion, etrimfos, quinalfos, dimetilvinfos, dimetoato, sulprofos, tiometon, vamidotion, piraclofos, piridafention, metil-pirimifos, propafos, fosalona, formotion, malation, tetraclorvinfos, ciorfenvinfos, cianofos, triclorfon,
Petição 870170014049, de 03/03/2017, pág. 20/70
10/16 metidation, fentoato, ESP, metil-azinfos, fention, heptenofos, metoxiclor, paration, fosfocarb, demeton-S-metil, monocrotofos, metamidofos, imiciafos, metil-paration, terbufos, fosfamidon, fosmet e forato;
[073] compostos de carbamato, tais como, carbaril, propoxur, aldicarb, carbofuran, tiodicarb, metomil, oxamil, etiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furatiocarb, isoprocarb, metolcarb, xililcarb, XMC e fenotiocarb;
[074] derivados de nereistoxin, tais como, cartap, tiociclam, bensultap e tiosultap de sódio;
[075] compostos clorados orgânicos, tais como, dicofol, tetradifon, endosulfan, dienoclor e dieldrin;
[076] compostos metalo orgânicos, tais como, óxido de fenbutatin e cihexatin;
[077] compostos piretroídes, tais como, fenvalerato, permetrin, cipermetrin, deltametrin, cihalotrin, teflutrin, etofenprox, flufenprox, ciflutrin, fenpropatrin, flucitrinato, fluvalinato, cicloprotrin, lambda-cihalotrin, piretrinas, esfenvalerato, tetrametrin, resmetrin, protrifenbute, bifentrin, zetacipermetrin, acrinatrin, alfa-cipermetrin, aletrin, gama-cihalotrin, tetacipermetrin, tau-fluvalinato, tralometrin, proflutrin, beta-cipermetrin, betaciflutrin, metoflutrin, fenotrin e flumetrin;
[078] compostos de benzoil-ureia, tais como, diflubenzuron, clorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, noviflumuron, bistrifluron, e fluazuron;
[079] compostos semelhantes ao hormônio juvenil, tais como metopreno, piriproxifen, fenoxicarb e diofenolan;
[080] compostos de piridazinona, tal como, pridaben;
[081] compostos de pirazol, tais como, fenpiroximato, fipronil, tebufenpirad, etiprol, tolfenpirad, acetoprole, pirafluprol e piriprol;
[082] neonicotinoides, tais como, imidacloprid, nitenpiram, acetamiprida, tiacloprida, tiametoxam, clotianidina, nidinotefuran, dinotefuran e nitiazina;
Petição 870170014049, de 03/03/2017, pág. 21/70
11/16 [083] compostos de hidrazina, tais como, tebufenozida, metoxifenozida, cromafenozida e halofenozida;
[084] compostos de piridina, tais como, flonicamida;
[085] compostos de ácido tetronico, tal como espirodiclofen;
[086] compostos de estrobilurina, tal como fiuacripirim;
[087] compostos de pirimidinamina, tal como flufenerim;
[088] compostos dinitro;
[089] compostos sulfuro orgânicos;
[090] compostos de ureia;
[091] compostos triazina;
[092] compostos de hidrazona;
[093] outros compostos, tais como buprofezin, hexitiazox, amitraz, clordimeform, silafluofen, triazamate, pimetrozina, pirimidifen, clorfenapir, indoxacarb, acequinocil, etoxazol, ciromazina, 1,3-dicloropropeno, diafentiuron, benclotiaz, bifenazato, espiromesifen, espirotetramat, propargite, clofentezina, metaflumizona, flubendiamida, ciflumetofen, clorantraniliprol, cienopirafen, pirifluquinazona, fenazaquin, amidoflumet, clorobenzoato, sulfluramida, hidrametilnon, metaldehido, HGW-86, AKD1022, rianodina, piridalil e verbutin; e semelhantes.
[094] Podem ainda ser empregados em combinação com ou em conjunto com agroquímicos microbianos, tais como Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, proteínas inseticidas cristalizadas produzidas pelo Bacillus thuringiensis, vírus de insetos, fungos etomopatogênicos, e fungos nematófagos; antibióticos ou antibióticos semi-sintéticos, tais como, avermectina, benzoato de emamectina, milbemectina, milbemicina, spinosad, ivermectina, lepimectina, DE-175, abamectina, emamectina e spinetoram; produtos naturais, tais como azadiractina e rotenona; e repelentes, tal como DEET.
[095] Na composição da presente invenção, uma relação em peso adequada de (a) pelo menos um composto imidazólico e (b) folpet varia
Petição 870170014049, de 03/03/2017, pág. 22/70
12/16 usualmente de 1:10.000 a 10.000:1, e preferentemente de 1:2.000 a 2.000:1. [096] A presente invenção também se refere a um método para controlar um fitopatógeno compreendendo aplicar a composição da presente invenção a uma planta ou ao solo. A concentração do ingrediente ativo a ser utilizado para a composição da presente invenção varia de acordo com o objetivo das diferentes culturas, do método a ser usado, da forma de preparação, da quantidade aplicada, do tempo de aplicação, dos tipos de patógenos nocivos e similares, e pode não necessariamente ser definida. No entanto, no tratamento da folhagem ou tratamento do solo por encharcamento, como uma concentração de ingrediente ativo, o composto imidazol de fórmula (I) acima é normalmente utilizado em uma concentração de 0,01 a 1.000 ppm, e de preferência de 0,3 a 500 ppm, e a concentração do folpet é normalmente empregada em uma concentração de 0,1 a 10.000 ppm, e de preferência de 0,5 a 5.000 ppm.
OS EFEITOS VANTAJOSOS DA INVENÇÃO [097] Na composição da presente invenção, o efeito fungicida contra uma cultura cultivada infectada por um fitopatógeno é estável e altamente ativa para que a composição possa controlar um fitopatógeno. DESCRIÇÃO DAS MODALIDADES DE REALIZAÇÕES [098] A seguir, as modalidades de realizações preferidas de um fungicida para agricultura ou horticultura da composição da presente invenção serão exemplificadas, mas não devem ser interpretadas como a presente invenção sendo limitada a estas realizações.
[099] (1) Uma composição fungicida agrícola ou hortícola compreendendo: (a) pelo menos um composto imidazólico representado pela fórmula (I) e (b) folpet, como ingredientes ativos.
[100] (2) A composição descrita no item (1) acima que compreende uma quantidade sinérgica eficaz de (a) pelo menos um composto imidazólico representado pela fórmula (I) e (b) folpet.
[101] (3) A composição de acordo com o item (1) acima, em que uma relação em peso de (a) pelo menos um composto imidazólico representado
Petição 870170014049, de 03/03/2017, pág. 23/70
13/16 pela fórmula (I) e (b) folpet é de 1:10.000 a 10.000:1.
[102] (4) A composição de acordo com o item (1) acima, em que uma relação em peso de (a) pelo menos um composto imidazólico representado pela fórmula (I) e (b) folpet é de 1:2.000 a 2.000:1.
[103] (5) A composição de acordo com os itens (1) a (4) acima, em que o composto imidazólico de fórmula (I) é a ciazofamida.
[104] (6) O método para controlar um fitopatógeno, compreendendo a aplicação de uma quantidade eficaz de (a) pelo menos um composto imidazólico representado pela formula (I) e uma quantidade eficaz de (b) folpet a uma planta ou ao solo.
EXEMPLOS [105] A seguir, os exemplos de testes no que diz respeito à presente invenção serão descrito abaixo, mas não se deve considerar que a presente esteja limitada a estes exemplos.
EXEMPLO TESTE 1:
[106] Teste de inibição do crescimento do micélio contra o gênero Pythium (Phytium aristoporum) [107] O Phytium aristoporum foi pré-cultivado. As hifas obtidas (4 mm de diâmetro) foram transplantadas em meio agar sacarose de batata (PSA), incluindo um agente em uma concentração predeterminada, e depois cultivadas por dois dias a uma temperatura ambiente de 20°C, seguida da medição do diâmetro do micélio da colônia para obtenção da taxa de inibição do crescimento do micélio.
[108] O resultado está apresentado na Tabela 1.
[109] Além disso, um valor teórico da taxa de inibição foi calculado usando-se a fórmula de Colby. A composição da presente invenção apresentou um efeito sinergético no controle de um fitopatógeno.
Petição 870170014049, de 03/03/2017, pág. 24/70
14/16
TABELA 1
| Taxa de inibição do crescimento do micélio contra Phytium aristoporum (%) (Valores teóricos) | |||||
| ciazofamida | 100 ppm | 10 ppm | 1 ppm | 0,1 ppm | 0 ppm |
| folpet | |||||
| 100 ppm | 100 (94) | 100 (94) | 100 (94) | 100 (91) | 90 |
| 10 ppm | 95 (68) | 100 (66) | 100 (66) | 81 (54) | 45 |
| 1 ppm | 48 (43) | 60 (40) | 72 (40) | 47 (20) | 3 |
| 0,1 ppm | 47 (43) | 50 (40) | 60 (40) | 35 (20) | 3 |
| 0 ppm | 41 | 38 | 38 | 17 |
EXEMPLO TESTE 2:
[110] Teste de inibição do crescimento do micélio contra o gênero Pythium (Phytium aphanidermatum) [111] A taxa de inibição do crescimento do micélio foi obtida pela medição do diâmetro do micélio da colônia da mesma forma que no exemplo Teste 1.
[112] O resultado está apresentado na tabela 2.
[113] Além disso, o valor teórico da taxa de inibição foi calculado usando-se a fórmula de Colby, e está listado entre parênteses da Tabela 2. Se um valor experimental é maior do que o valor teórico obtido pela fórmula de Colby, a composição da presente invenção mostra um efeito sinérgico no controle de um fitopatógeno.
Petição 870170014049, de 03/03/2017, pág. 25/70
15/16
TABELA 2
| Taxa de inibição do crescimento do micélio contra Phytium aphanidermatum (%) (Valores teóricos) | |||||
| '^^Çiazofamida folpet | 100 ppm | 10 ppm | 1 ppm | 0,1 ppm | 0 ppm |
| 100 ppm | 100 (96) | 100 (92) | 100 (90) | 100 (91) | 80 |
| 10 ppm | 100 (92) | 100 (85) | 100 (82) | 100 (83) | 62 |
| 1 ppm | 90 (80) | 88 (60) | 90 (52) | 72 (54) | 0 |
| 0,1 ppm | 82 (80) | 78 (61) | 72 (53) | 74 (55) | 2 |
| 0 ppm | 80 | 60 | 52 | 54 |
[114] A seguir, estão os exemplos da composição da presente invenção descritos abaixo como exemplos de formulação, mas não se deve supor que a presente invenção é limitada a estes exemplos.
[115] EXEMPLO DE FORMULAÇÃO 1 (1) Ciazofamida partes em peso (2) Folpet partes em peso (3) condensado de sódio naftaleno formaldeído sulfonato (4) sulfonato de alquil-benzeno de sódio partes em peso partes em peso (5) argila partes em peso [116] No exposto acima, cada componente é misturado para a obtenção de um pó molhável.
(1) Ciazofamida (2) Folpet (3) carbonato de cálcio
0,5 partes em peso
2,5 partes em peso partes em peso
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16/16 (4) argila 77 partes em peso [117] No exposto acima, cada componente é misturado para a obtenção de um pó polvilhável.
[118] Embora a invenção tenha sido descrita em detalhes e com referência às modalidades de realizações específicas aqui descritas, deve ficar entendido para um especialista na técnica que diversas modificações poderão ser ai realizadas sem fugir do espírito e do escopo da presente invenção.
[119] Esta invenção é baseada no pedido Japonês de patente JP 2009-160257, depositado em 6 de julho de 2009, o conteúdo completo deste é aqui incorporado como referência. Todas as referências são aqui incorporadas integralmente.
[120] APLICAÇÃO INDUSTRIAL [121] Na composição da presente invenção, o efeito fungicida contra uma cultura infestada por um fitopatógeno é estável e intensamente ativo, e, portanto, esta composição pode controlar um fitopatógeno.
Claims (2)
- REIVINDICAÇÕES1. Composição fungicida agrícola e hortícola, caracterizada pelo fato de que compreende:(a) ciazofamida, e (b) folpet, como ingredientes ativos, em que a relação em peso de (a) ciazofamida para (b) folpet é de 1:1.000 a 1.000:1.
- 2. Método para o controle de um patógeno de planta, caracterizado pelo fato de que compreende:- a aplicação da composição conforme definida de acordo com reivindicação 1, a uma planta ou ao solo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009160257 | 2009-07-06 | ||
| PCT/JP2010/061736 WO2011004901A1 (en) | 2009-07-06 | 2010-07-06 | Agricultural or horticultural fungicide composition and its use for controlling plant pathogens |
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| BRPI1011796A2 BRPI1011796A2 (pt) | 2015-10-06 |
| BRPI1011796B1 true BRPI1011796B1 (pt) | 2019-01-22 |
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| BRPI1011796A BRPI1011796B1 (pt) | 2009-07-06 | 2010-07-06 | composição fungicida agrícola ou hortícola compreendendo ciazofamida e folpet como ingredientes ativos, e, método para o controle de um patógeno de planta com a dita composição |
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| RU (1) | RU2523285C2 (pt) |
| SI (2) | SI2451275T2 (pt) |
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| FR3096872A1 (fr) | 2019-06-05 | 2020-12-11 | UPL Corporation Limited | composition fongicide pour lutter contre l'infection zymoseptoria chez la plante |
| PE20230375A1 (es) * | 2020-07-08 | 2023-03-06 | Adama Makhteshim Ltd | Mezclas fungicidas |
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| AT209339B (de) † | 1948-05-18 | Exxon Research Engineering Co | Verfahren zur Herstellung von neuen N-Thiotrichlormethyl-substituierten heterocyclischen Stickstoffverbindungen | |
| CA1339133C (en) † | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| JP2606720B2 (ja) * | 1987-03-13 | 1997-05-07 | 石原産業株式会社 | イミダゾール系化合物及びそれらを含有する有害生物防除剤 |
| JPS6413163A (en) * | 1987-07-06 | 1989-01-18 | Minolta Camera Kk | Control method for electrophotographic copying machine |
| MY129863A (en) * | 1988-03-11 | 2007-05-31 | Ishihara Sangyo Kaisha | Biocidal composition |
| CN100340167C (zh) * | 2002-12-06 | 2007-10-03 | 陶氏农业科学公司 | 增效组合物 |
| ES2424840T3 (es) * | 2003-01-28 | 2013-10-09 | E.I. Du Pont De Nemours And Company | Insecticidas tipo ciano antranilamida |
| DE10310906A1 (de) * | 2003-03-13 | 2004-09-23 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| DE10347090A1 (de) * | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| AR046698A1 (es) * | 2003-11-11 | 2005-12-21 | Ishihara Sangyo Kaisha | Derivado bifenilo o su sal, y pesticida que lo contienen como un ingrediente activo |
| KR20080070676A (ko) † | 2005-11-22 | 2008-07-30 | 이시하라 산교 가부시끼가이샤 | 농원예용 살균제 조성물 및 식물 병해의 방제 방법 |
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2012
- 2012-01-03 CL CL2012000011A patent/CL2012000011A1/es unknown
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