BRPI0307730B1 - Fungicidal mixture, process for combating harmful fungi, and fungicidal agent - Google Patents
Fungicidal mixture, process for combating harmful fungi, and fungicidal agent Download PDFInfo
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- BRPI0307730B1 BRPI0307730B1 BRPI0307730B1 BR PI0307730 B1 BRPI0307730 B1 BR PI0307730B1 BR PI0307730 B1 BRPI0307730 B1 BR PI0307730B1
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- 241000233866 Fungi Species 0.000 title claims description 13
- 230000000855 fungicidal Effects 0.000 title claims description 11
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- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Description
“MISTURA FUNGICIDA, PROCESSO PARA COMBATER FUNGOS NOCIVOS, E, AGENTE FUNGICIDA”. A presente invenção refere-se a misturas fungicidas, contendo (1) 2-[2-(l-clorociclopropil)-3-(2-clorofenil)-2-hidróxipropil]-2,4-diidro-[l,2,4]-triazol-3-tiona (protioconazol) da fórmula I ou um sal ou aduto do mesmo, d) e pelo menos um outro triazol ou um sal ou aduto do mesmo, selecionado a partir do grupo que consiste de, (2) epoxiconazol da fórmula II (II) ou (3) metconazol da fórmula III (III) ou (4) propiconazol da fórmula IV (IV) ou (5) fluquinconazol da fórmula V (V) ou (6) penconazol da fórmula VI, (VI) ou (7) difenconazol da fórmula VII (VII) ou (8) hexaconazol da fórmula VIII (VIII) ou (9) ciproconazol da fórmula IX (IX) ou (10) flusilazol da fórmula X (X) ou (11) tetraconazol da fórmula XI (XI) ou (12) fenbuconazol da fórmula XII (XII) ou (13) miclobutanil da fórmula XIII (XIII) ou (14) simeconazol da fórmula XIV (XIV) ou (15) ipconazol da fórmula XV ou (16) triticonazol da fórmula XVI (XVI) em uma quantidade sinergicamente eficaz."FUNGICIDE MIX, PROCESS TO COMBAT HARMFUL FUNGI, AND, FUNGICIDE AGENT". The present invention relates to fungicidal mixtures containing (1) 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro [1,2,4 ] -triazole-3-thione (protioconazole) of formula I or a salt or adduct thereof, d) and at least one other triazole or salt or adduct thereof selected from the group consisting of, (2) epoxyconazole of formula II (II) or (3) metconazole of formula III (III) or (4) propiconazole of formula IV (IV) or (5) fluquinconazole of formula V (V) or (6) penconazole of formula VI, (VI ) or (7) diphenconazole of formula VII (VII) or (8) hexaconazole of formula VIII (VIII) or (9) cyproconazole of formula IX (IX) or (10) flusilazole of formula X (X) or (11) tetraconazole of formula XI (XI) or (12) fenbuconazole of formula XII (XII) or (13) myclobutanyl of formula XIII (XIII) or (14) simeconazole of formula XIV (XIV) or (15) ipconazole of formula XV or (16 ) triticonazole of formula XVI (XVI) in a synergistically effective amount.
Além disso, a invenção refere-se a um processo para o combate de fungos nocivos com misturas do composto I com pelo menos um dos compostos II a XVI e o uso do composto I com pelo menos um dos compostos II a XVI para a preparação das referidas misturas, assim como composições, que contêm estas misturas.Further, the invention relates to a process for combating harmful fungi with mixtures of compound I with at least one of compounds II to XVI and the use of compound I with at least one of compounds II to XVI for the preparation of the compounds. said mixtures as well as compositions containing such mixtures.
Protioconazol da fórmula I, isto é 2-[2-(l-clorociclopropil)-3-(2-clorofenil)-2-hidróxipropil]-2,4-diidro-[l ,2,4]-triazol-3-tiona, já é conhecido a partir da WO 96/16048. A WO 98/47367 descreve uma quantidade de combinações de compostos ativos de protioconazol com vários outros compostos fungicidas.Protioconazole of formula I, ie 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro [1,2,4] triazol-3-thione , is already known from WO 96/16048. WO 98/47367 describes a number of combinations of protioconazole active compounds with various other fungicidal compounds.
Epoxiconazol da fórmula II e o seu uso como agente de proteção de plantas são expostos na EP-B 0 196 038.Epoxiconazole of formula II and its use as a plant protection agent are set forth in EP-B 0 196 038.
Metconazol da fórmula III, também, já é conhecido e é descrito na EP-B 0 267 778.Metconazole of formula III, too, is already known and is described in EP-B 0 267 778.
Propiconazol da fórmula IV, também, já é conhecido e é descrito na DE-A 2551560.Propiconazole of formula IV, too, is already known and is described in DE-A 2551560.
Fluquinconazol da fórmula V é descrito no Pesticide Manual, 12a Ed. (2000), página 449.Fluquinconazole of formula V is described in Pesticide Manual, 12th Ed. (2000), page 449.
Penconazol da fórmula VI é descrito no Pesticide Manual, 12a Ed. (2000), página 712.Penconazole of formula VI is described in Pesticide Manual, 12th Ed. (2000), page 712.
Difenconazol da fórmula VII é conhecido a partir da EP-A-0 112 284.Diphenconazole of formula VII is known from EP-A-0 112 284.
Hexaconazol da fórmula VIII é descrito na DE-A-30 42 303.Hexaconazole of formula VIII is described in DE-A-30 42 303.
Ciproconazol da fórmula IX é descrito na DE-A-34 06 993.Cyproconazole of formula IX is described in DE-A-34 06 993.
Flusilazol da fórmula X é conhecido a partir da EP-A-0 068 813.Flusilazole of formula X is known from EP-A-0686813.
Tetraconazol da fórmula XI é conhecido a partir da EP-A-0 234 242.Tetraconazole of formula XI is known from EP-A-0 234 242.
Fenbuconazol da fórmula XII é descrito na DE-A-37 21 786.Fenbuconazole of formula XII is described in DE-A-37 21 786.
Miclobutanil da fórmula XIII é descrito na EP-A-0 145 294.Miclobutanil of formula XIII is described in EP-A-0 145 294.
Simeconazol da fórmula XIV é descrito na BCPC Conference - Pests and Diseases 2000, pp. 557-562.Simeconazole of the formula XIV is described in the BCPC Conference - Pests and Diseases 2000, pp. 557-562.
Ipconazol da fórmula XV é descrito na EP-A-0 267 778.Ipconazole of formula XV is described in EP-A-0 267 778.
Triticonazol da fórmula XVI é descrito na EP-A-0 378 953.Triticonazole of formula XVI is described in EP-A-0 378 953.
Tendo em vista uma redução das taxas de aplicação e uma melhora do espectro de atividade dos compostos I e XVI conhecidos, as misturas de acordo com a presente invenção têm como objetivo apresentar uma atividade melhorada contra fungos nocivos mediante a aplicação de quantidades totais reduzidas de compostos ativos (misturas sinérgicas).With a view to reducing application rates and improving the activity spectrum of known compounds I and XVI, the mixtures according to the present invention aim to show improved activity against harmful fungi by applying reduced total amounts of compounds. active (synergistic mixtures).
Deste modo, a mistura precedentemente definida de protioconazol com pelo menos um triazol adicional foi encontrada. Foi além disso verificado que, quando do uso simultâneo, seja de modo conjunto ou de modo separado, do composto I com pelo menos um dos compostos II a XVI ou quando do uso do composto I com pelo menos um dos compostos II a XVI de modo sucessivo, os fungos nocivos podem ser melhor combatidos do que com compostos isolados. 2-[2-(l-Clorociclopropil)-3-(2-clorofenil)-2-hidróxipropil]-2,4-diidro-[l,2,4]-triazol-3-tiona (protioconazol) da fórmula I é também conhecido a partir da WO 96-16 048. O composto pode estar presente na forma “tiono” da fórmula, (I) ou na forma “mercapto” tautomérica da fórmula, (Ia) Devido a razões de simplicidade, apenas a forma “tiono” é apresentada em cada caso.Thus, the previously defined mixture of protioconazole with at least one additional triazole was found. It has furthermore been found that when used together or separately of compound I with at least one of compounds II to XVI or when using compound I with at least one of compounds II to XVI successive fungi can be better combated than with isolated compounds. 2- [2- (1-Chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro [1,2,4] triazol-3-thione (protioconazole) of formula I is also known from WO 96-16 048. The compound may be present in the thiono form of the formula (I) or the tautomeric mercapto form of the formula (Ia). For reasons of simplicity, only the form tiono ”is presented in each case.
Epoxiconazol da fórmula II (II) é conhecido a partir da EP-B 0 196 038.Epoxyconazole of formula II (II) is known from EP-B 0 196 038.
Metconazol da fórmula III (III) é conhecido a partir da EP-B 0 267 778.Metconazole of formula III (III) is known from EP-B 0 267 778.
Proniconazol da fórmula IV (IV) é conhecido a partir da DE-A 25 51 560.Proniconazole of formula IV (IV) is known from DE-A 25 51 560.
Fluquinconazol da fórmula V (V) é descrito no Pesticide Manual, 12a Ed. (2000), página 449. Penconazol da fórmula VI (VI) é descrito no Pesticide Manual, 12a Ed. (2000), página 712. Difenconazol da fórmula VII (VII) é conhecido a partir da EP-A-0 112 284.Fluquinconazole of formula V (V) is described in Pesticide Manual, 12th Ed. (2000), page 449. Penconazole of formula VI (VI) is described in Pesticide Manual, 12th Ed. (2000), page 712. Diphenconazole of formula VII (VII) is known from EP-A-0 112 284.
Hexaconazol da fórmula VIII (VIII) é descrito na DE-A-30 42 303.Hexaconazole of formula VIII (VIII) is described in DE-A-30 42 303.
Ciproconazol da fórmula IX (ix) é descrito na DE-A-34 06 993.Cyproconazole of formula IX (ix) is described in DE-A-34 06 993.
Flusilazol da fórmula X " (X) é conhecido a partir da EP-A-0 068 813. Tetraconazol da fórmula XI (XI) é conhecido a partir da EP-A-0 234 242. Fenbuconazol da fórmula XII (XII) é descrito na DE-A-37 21 786.Flusilazole of formula X "(X) is known from EP-A-0 068 813. Tetraconazole of formula XI (XI) is known from EP-A-0 234 242. Fenbuconazole of formula XII (XII) is described. DE-A-37 21 786.
Miclobutanil da fórmula XIII (XIII) é descrito na EP-A-0 145 294.Miclobutanil of formula XIII (XIII) is described in EP-A-0 145 294.
Simeconazol da fórmula XIV (XIV) é conhecido a partir da BCPC Conference - Pests and Diseases 2000, págs. 557-562.Simeconazole of formula XIV (XIV) is known from the BCPC Conference - Pests and Diseases 2000, p. 557-562.
Ipconazol da fórmula XV é descrito na EP-A-0 267 778.Ipconazole of formula XV is described in EP-A-0 267 778.
Triticonazol da fórmula XVI (XVI) é descrito na EP-A-0 378 953.Triticonazole of formula XVI (XVI) is described in EP-A-0 378 953.
Devido ao caráter básico de seus átomos de nitrogênio, os compostos I a XVI são capazes de formar sais ou produtos de adição com ácidos orgânicos ou inorgânicos ou com íons metálicos.Due to the basic character of their nitrogen atoms, compounds I to XVI are capable of forming salts or addition products with organic or inorganic acids or metal ions.
Exemplos de ácidos inorgânicos são halogenetos de hidrogênio, tais como fluoreto de hidrogênio, cloreto de hidrogênio, brometo de hidrogênio e iodeto de hidrogênio, ácido sulfurico, ácido fosfórico e ácido nítrico.Examples of inorganic acids are hydrogen halides such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid.
Como ácidos orgânicos podem ser citados, por exemplo, ácido fórmico, ácido carbônico e ácidos alcanóicos, tais como ácido acético, ácido trifluoroacético, ácido tricloroacético e ácido propiônico, assim como ácido glicólico, ácido tiociânico, ácido láctico, ácido succínico, ácido cítrico, ácido benzóico, ácido cinâmico, ácido oxálico, ácidos alquil sulfônicos (ácido sulfônicos com radicais alquila de cadeia linear ou ramificada com de 1 a 20 átomos de carbono), ácidos aril sulfônicos ou ácidos dissulfônicos (radicais aromáticos, tais como fenila e naftila, que podem portar um ou dois grupos de ácido sulfônico), ácidos alquil fosfônicos (ácidos fosfônicos com radicais alquila de cadeia linear ou ramificada com de 1 a 20 átomos de carbono) ácidos aril fosfônicos ou ácidos aril difosfônicos (radicais aromáticos, tais como fenila e naftila, que podem portar um ou dois radicais de ácido fosfórico), em que os radicais alquila ou os radicais arila podem portar outros substituintes, por exemplo ácido p-tolueno sulfônico, ácido salicílico, ácido p-amino salicílico, ácido 2-fenóxi benzóico, ácido 2-acetóxi benzóico, etc.Organic acids may include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkyl sulfonic acids (sulfonic acids with straight or branched chain alkyl radicals of 1 to 20 carbon atoms), aryl sulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl which may carry one or two groups of sulfonic acid), alkyl phosphonic acids (straight chain or branched chain alkyl phosphonic acids of 1 to 20 carbon atoms) aryl phosphonic acids or diphosphonic aryl acids (aromatic radicals such as phenyl and naphthyl , which may carry one or two phosphoric acid radicals), wherein the alkyl radicals or the Other aryl moieties may carry other substituents, for example p-toluene sulfonic acid, salicylic acid, p-amino salicylic acid, 2-phenoxy benzoic acid, 2-acetoxy benzoic acid, etc.
Como íons metálicos podem ser citados, em especial, os íons dos elementos do segundo grupo principal, em especial cálcio e magnésio, do terceiro e quarto grupo principal, em especial alumínio, estanho e chumbo, assim como do primeiro a oitavo grupos de transição, em especial cromo, manganês, ferro, cobalto, níquel, cobre, zinco e outros. São preferidos os íons metálicos dos elementos dos grupos de transição do quarto período. Os metais podem, neste caso, estar presentes em várias das valências que eles possam assumir. São preferidas misturas de protioconazol com epoxiconazol.Metal ions may be cited in particular by the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, as well as the first to eighth transition groups, especially chrome, manganese, iron, cobalt, nickel, copper, zinc and others. The metal ions of the fourth period transition group elements are preferred. Metals may in this case be present in many of the valences they may assume. Mixtures of protioconazole with epoxiconazole are preferred.
Além disso, são também preferidas misturas de protioconazol com metconazol. São também preferidas misturas de protioconazol com propiconazol. São ainda preferidas misturas de protioconazol com fluquinazol. São ainda preferidas misturas de protioconazol com penconazol. São além disso preferidas misturas de protioconazol com difenconazol. São ainda preferidas misturas de protioconazol com hexaconazol. São ainda preferidas misturas de protioconazol com ciproconazol. São também preferidas misturas de protioconazol com flusilazol. São ainda preferidas misturas de protioconazol com tetraconazol. São além disso preferidas misturas de protioconazol com fenbuconazol. São ainda preferidas misturas de protioconazol com miclobutanil. São também preferidas misturas de protioconazol com simeconazol. São ainda preferidas misturas de of protioconazol com ipconazol. São ainda preferidas misturas de protioconazol com triticonazol. São, além disso, preferidas misturas temárias de protioconazol com dois outros dos triazóis acima descritos.In addition, mixtures of protioconazole with metconazole are also preferred. Mixtures of protioconazole with propiconazole are also preferred. Further preferred are mixtures of protioconazole with fluquinazole. Mixtures of protioconazole with penconazole are further preferred. Further preferred are mixtures of protioconazole with difenconazole. Further preferred are mixtures of protioconazole with hexaconazole. Further preferred are mixtures of protioconazole with cyproconazole. Mixtures of protioconazole with flusilazole are also preferred. Further preferred are mixtures of protioconazole with tetraconazole. Mixtures of protioconazole with fenbuconazole are further preferred. Further preferred are mixtures of protioconazole with miclobutanil. Mixtures of protioconazole with simeconazole are also preferred. Mixtures of protioconazole with ipconazole are further preferred. Further preferred are mixtures of protioconazole with triticonazole. Further preferred are temporary mixtures of protioconazole with two others of the above described triazoles.
Quando da preparação das misturas, é preferido empregar os compostos ativos I a XVI puros, aos quais podem ser adicionados posteriormente outros compostos ativos contra fungos nocivos ou contra outras pestes, tais que insetos, aracnídeos ou nematodos ou ainda herbicidas ou outros compostos ativos para a regulação do crescimento ou fertilizantes.When preparing the mixtures, it is preferred to employ pure active compounds I to XVI, to which other active compounds against harmful fungi or other pests such as insects, arachnids or nematodes or herbicides or other active compounds may be added thereafter. growth regulation or fertilizers.
As misturas do composto I com pelo menos um dos compostos II a XVI ou do composto I com pelo menos um dos compostos II a XVI podem ser aplicadas de modo simultâneo ou de modo separado, sendo caracterizadas por uma notável atividade contra um amplo espectro de fungos fitopatogênicos, em especial da classe dos ascomicetas, basidiomicetas, ficomicetas e deuteromicetas. Estes são em parte sistemicamente ativos e podem, portanto, ser também usados como fungicidas que atuam sobre as folhas ou sobre o solo.Mixtures of compound I with at least one of compounds II to XVI or compound I with at least one of compounds II to XVI may be applied simultaneously or separately and are characterized by remarkable activity against a broad spectrum of fungi. plant pathogens, in particular of the class of ascomycetes, basidiomycetes, phycomycetes and deuteromycetes. These are in part systemically active and can therefore also be used as leaf or soil fungicides.
Eles são especialmente importantes para o combate de uma variedade de fungos em diversas plantas de cultura, tais como algodão, verduras (por exemplo, pepinos, feijões, tomates, batatas, e cucurbitáceos), cevada, relva, aveia, banana, café, milho, frutas, arroz, centeio, soja, videiras, trigo, plantas ornamentais, cana-de-açúcar e uma variedade de sementes.They are especially important for combating a variety of fungi in a variety of crop plants, such as cotton, vegetables (eg cucumbers, beans, tomatoes, potatoes, and cucurbits), barley, grass, oats, bananas, coffee, corn. , fruits, rice, rye, soybeans, vines, wheat, ornamentals, sugar cane and a variety of seeds.
Eles são, em especial, apropriados para o combate dos seguintes fungos fitopatogênicos: Blumeria graminis (míldeo pulvurulento) em cereais, Erysiphe cichoracearum e Sphaerotheca fuliginea em cucurbitáceos, Podosphaera leucotricha em maçãs, Uncinula necator em videiras, espécies Puccinia em cereais, espécies Rhizoctonia em algodão, arroz e relvados, espécie Ustilago em cereais e cana-de-açúcar, Venturia inaequalis (sama) em maçãs, espécie Helminthosporium em cereais, Septoria nodorum em trigo, Botrytis cinera (mofo cinza) em morangos, vegetais, plantas ornamentais e videiras, Cercospora arachidicola em amendoins, Pseudocercosporella herpotrichoides em trigo e cevada, Pyricularia oryzae em arroz, Phytophthora infestans em batatas e tomates, Plasmopara viticola em videiras, espécies Pseudoperonospora em lúpulos e pepinos, espécies Alternaria em vegetais e frutas, espécies Mycosphaerella em bananas e especies Fusarium e Verticillium.They are, in particular, suitable for combating the following phytopathogenic fungi: Blumeria graminis (pulvurulent mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in vines, Puccinia species cotton, rice and lawns, Ustilago species in cereals and sugarcane, Venturia inaequalis (sama) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis cinera (gray mold) in strawberries, vegetables, ornamentals and vines , Cercospora arachidicola in peanuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in vines, Pseudoperonospora species in hops and cucumbers, Alternaria species in vegetables and fruits, Mycos species in bananas and fruits, Fusarium and Verticillium.
Eles podem, além disso, ser empregados em proteção de material (por exemplo, na proteção de madeira), por exemplo, contra Paecilomyces variotii. O composto I e pelo menos um dos compostos II a XVI podem ser aplicados simultaneamente, seja de modo conjunto ou de modo separado, ou de modo sucessivo, em cujo caso a seqüência, no caso de aplicação separada, não possui, de modo geral, nenhum efeito sobre um resultado bem sucedido do combate.They may furthermore be employed in material protection (eg in wood protection), for example against Paecilomyces variotii. Compound I and at least one of compounds II to XVI may be applied simultaneously, either together or separately, or successively, in which case the sequence, in the case of separate application, generally has no effect. no effect on a successful combat outcome.
Os compostos I e II são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and II are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e III são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and III are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e IV são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and IV are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e V são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and V are usually employed in a weight ratio of 20: 1 to 1:20, in particular 10: 1 to 1:10, preferably 5: 1 to 1: 5.
Os compostos I e VI são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and VI are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e VII são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10,de modo preferido de 5:1 a 1:5.Compounds I and VII are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1: 10, preferably from 5: 1 to 1: 5.
Os compostos I e VIII são empregados, de modo usual, em uma razão em peso 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and VIII are usually employed in a weight ratio 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e IX são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and IX are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e X são empregados, de modo preferido, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and X are preferably employed in a weight ratio of 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XI são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XI are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XII são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XII are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XIII são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XIII are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XIV são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XIV are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XV são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XV are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
Os compostos I e XVI são empregados, de modo usual, em uma razão em peso de 20:1 a 1:20, em particular de 10:1 a 1:10, de modo preferido de 5:1 a 1:5.Compounds I and XVI are usually employed in a weight ratio of from 20: 1 to 1:20, in particular from 10: 1 to 1:10, preferably from 5: 1 to 1: 5.
As taxas de aplicação das misturas de acordo com a invenção são, sobretudo no caso de áreas de cultura agrícola, de acordo com o efeito desejado, de 0,01 a 8 kg/ ha, de modo preferido de 0,1 a 5 kg/ ha, em especial de 0,1 a 3,0 kg/ha.The application rates of the mixtures according to the invention are, especially in the case of agricultural crop areas, according to the desired effect, from 0.01 to 8 kg / ha, preferably from 0.1 to 5 kg / ha. ha, in particular from 0.1 to 3.0 kg / ha.
As taxas de aplicação para o composto I são de 0,01 a 1 kg/ha, de modo preferido de 0,05 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ha.Application rates for compound I are from 0.01 to 1 kg / ha, preferably from 0.05 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha.
De modo correspondente, as taxas de aplicação para o composto II são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ha, em especial de 0,05 a 0,3 kg/ha.Correspondingly, application rates for compound II are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto III são de 0,01 a 1 kg/ ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound III are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto IV são de 0,01 a 1 kg/ ha, de modo preferido de 0,02 a 0,5 kg/ ha, em particular de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound IV are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto V são de 0,01 a 1 kg/ ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, the application rates for compound V are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto VI são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound VI are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto V são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, the application rates for compound V are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto VII são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound VII are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto VIII são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound VIII are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto IX são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, the application rates for compound IX are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto X são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound X are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XI são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XI are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XII são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XII are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XIII são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XIII are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XIV são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XIV are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XV são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XV are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
De modo correspondente, as taxas de aplicação para o composto XVI são de 0,01 a 1 kg/ha, de modo preferido de 0,02 a 0,5 kg/ ha, em especial de 0,05 a 0,3 kg/ ha.Correspondingly, application rates for compound XVI are from 0.01 to 1 kg / ha, preferably from 0.02 to 0.5 kg / ha, in particular from 0.05 to 0.3 kg / ha. there is.
Para o tratamento da semente são usadas, de modo geral, taxas de aplicação na mistura de 0,001 a 250 g/ kg de semente, de modo preferido de 0,01 a 100 g/ kg, em especial de 0,01 a 50 g/ kg.For seed treatment application rates are generally used in the mixture from 0.001 to 250 g / kg of seed, preferably from 0.01 to 100 g / kg, in particular from 0.01 to 50 g / kg. kg
Se for desejado o combate de fungos fitopatogênicos, a aplicação do composto I ocorre de modo separado ou conjunto, com pelo menos um dos compostos II a XVI ou de misturas do composto I com pelo menos um dos compostos II a XVI através da pulverização ou do polvilhamento das sementes, das plantas ou do solo antes ou após a semeadura das plantas ou após a emergência das plantas.If combating phytopathogenic fungi is desired, the application of compound I occurs separately or together with at least one of compounds II to XVI or mixtures of compound I with at least one of compounds II to XVI by spraying or spraying. sprinkling of seeds, plants or soil before or after sowing or after plant emergence.
As misturas sinérgicas fungicidas de acordo com a invenção ou respectivamente do composto I e de pelo menos um dos compostos II a XVI podem, por exemplo, ser apresentadas diretamente sob a forma de soluções pulverizáveis, pós ou suspensões, ou sob a forma de suspensões, aquosas, oleosas ou outras altamente concentradas, dispersões, emulsões, dispersões oleosas, pastas, polvilhos, materiais para o espalhamento ou grânulos e podem ser aplicadas através de pulverização, nebulização, polvilhamento, espalhamento ou rega. A forma de aplicação depende da finalidade de uso; ela deve, em cada caso, permitir uma distribuição o mais fina e uniforme possível da mistura de acordo com a invenção.Synergistic fungicidal mixtures according to the invention or respectively of compound I and at least one of compounds II to XVI may, for example, be presented directly as sprayable solutions, powders or suspensions, or as suspensions, aqueous, oily or other highly concentrated, dispersions, emulsions, oily dispersions, pastes, dustings, spreading materials or granules and may be applied by spraying, misting, dusting, spreading or watering. The form of application depends on the intended use; It must in each case permit the finest and most uniform distribution of the mixture according to the invention.
As formulações são preparadas de modo em si conhecido, por exemplo, através da adição de solventes e/ou de veículos. As formulações são, de modo usual, misturadas com aditivos inertes, tais como agentes de emulsificação ou agentes de dispersão.The formulations are prepared in a manner known per se, for example by the addition of solvents and / or vehicles. The formulations are usually mixed with inert additives such as emulsifying agents or dispersing agents.
Como tensoativos, podem ser citados os sais de metal alcalino, alcalino terrosos e de amônio de ácidos sulfônicos aromáticos, por exemplo, ácidos lignino, fenol, naftaleno e dibutilnaftaleno sulfônicos, assim como os ácidos graxos, alquil e alquilaril sulfonatos, alquil sulfatos, lauril éter sulfatos e sulfatos de álcool graxo, e sais de hexa-, hepta- e octadecanóis sulfatados e de éteres glicólicos de álcool graxo, produtos de condensação de naftaleno sulfonado e dos ácidos naftaleno sulfônicos com fenol e formaldeído, éteres de polioxietileno octilfenol, isooctil, octil ou nonilenol etoxilados, alquilfenol poliglicol éteres, tributilfenil poliglicol éteres, álcoois de alquilaril poliéter, álcool isotridecílico, condensados de álcool graxo/ óxido de etileno, óleo de rícino etoxilado, polioxietileno alquil éteres ou polioxipropileno alquil éteres, acetato de éter poliglicólico de álcool laurílico, ésteres de sorbitol, lixívia de sulfito de lignina ou de metil celulose. Pós, materiais para o espalhamento e polvilhos podem ser preparados através da mistura ou moagem conjunta do composto I e de pelo menos um dos compostos II a XVI ou da mistura dos compostos I com pelo menos um composto II a XVI com um veículo sólido.As surfactants, mention may be made of alkali metal, alkaline earth and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalene sulfonic acids, as well as fatty acids, alkyl and alkylaryl sulfonates, alkyl sulfates, lauryl fatty alcohol ether sulphates and sulphates, sulphated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers, sulphonated naphthalene and naphthalene sulphonic acid condensations with phenol and formaldehyde, polyoxyethylene octylphenol, isooctyl ethers, ethoxylated octyl or nonylenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, ethoxylated fatty alcohol / oxide condensates, polyoxyethylene alkyl ethers or polyoxypropyl ethyl ether alkylether polyethylene ethers , sorbitol esters, lignin sulfite bleach or u of methyl cellulose. Powders, spreading materials and dust can be prepared by mixing or grinding together compound I and at least one of compounds II to XVI or mixing compounds I with at least one compound II to XVI with a solid carrier.
Grânulos (por exemplo, grânulos revestidos, grânulos impregnados ou grânulos homogêneos) são preparados, de modo usual, através da ligação do composto ativo ou dos compostos ativos a um veículo sólido.Granules (e.g., coated granules, impregnated granules or homogeneous granules) are usually prepared by binding the active compound or active compounds to a solid carrier.
Como cargas ou veículos sólidos podem ser usados, por exemplo, terras minerais, tais como sílica gel, sílicas, silicatos, talco, caulim, pedra calcárea, cal, giz, argila ferruginosa ou aluminosa, limo argiloso-calcário, argila, dolomita, terras diatomáceas, sulfato de cálcio ou de magnésio, óxido de magnésio, materiais plásticos moídos, assim como fertilizantes, tais como sulfato de amônio, fosfato de amônio, nitrato de amônio, uréias e produtos vegetais, tais como farinha de grãos, farinha de cascas de árvores, serragem e farinha de cascas de nozes, pós celulósicos e outros veículos sólidos.Solid fillers or carriers may be used, for example, mineral earth such as silica gel, silica, silicate, talc, kaolin, limestone, lime, chalk, rust and clay, limestone, clay, dolomite, earth diatoms, calcium or magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as grain flour, trees, sawdust and flour from nut shells, cellulosic powders and other solid vehicles.
As formulações compreendem, de modo geral, de 0,1 a 95%, em peso, de modo preferido de 0,5 a 90%, em peso, do composto I e de pelo menos um dos compostos II a XVI ou da mistura do composto I com pelo menos um dos compostos II a XVI. Os compostos são, neste caso, usados em uma pureza de 90% a 100%, de modo preferido de 95% a 100% (de acordo com o espectro RMN ou HPLC). A aplicação dos compostos I a XVI ou de misturas ou das formulações correspondentes é executada de tal modo que os fungos nocivos, o seu habitat ou as plantas, sementes, solos, superfícies, materiais ou espaços a serem liberados dos mesmos são tratados com uma quantidade fungicidamente eficaz da mistura, ou respectivamente do composto I e pelo menos um dos compostos II a XVI, no caso de aplicação separada. A aplicação pode ser efetuada antes ou após a infecção pelos fungos nocivos.The formulations generally comprise from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of compound I and at least one of compounds II to XVI or the mixture of compound I with at least one of compounds II to XVI. The compounds in this case are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum). The application of compounds I to XVI or mixtures or their corresponding formulations is such that the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be released from them are treated with an amount fungicidally effective mixture, or respectively of compound I and at least one of compounds II to XVI, in the case of separate application. Application can be done before or after infection by harmful fungi.
Exemplo de uso A atividade sinérgica das misturas de acordo com a invenção pode ser demonstrada através dos seguintes experimentos: Os compostos ativos foram preparados, de modo conjunto ou de modo separado, como uma emulsão a 10% de concentração em uma mistura de 63%, em peso, de cicloexanona e 27 %, em peso, de agente de emusificação e diluídos respectivamente à concentração desejada com água. A avaliação foi executada através da verificação das superfícies foliares infectadas, em percentual. Estes valores percentuais foram convertidos em eficácias. A eficácia (W) foi determinada de acordo com a fórmula de Abbot, como se segue: α corresponde à infeção fungica das plantas tratadas em % e β corresponde à infecção fungica das plantas não- tratadas (controle) em % Uma eficácia de 0 corresponde a um nível de infestação das plantas tratadas correspondente ao das plantas não-tratadas; no caso de uma eficácia de 100, as plantas tratadas não apresentam nenhum sinal de infestação. A eficácia a ser esperada das misturas de composto ativo foram determiandas de acordo com a fórmula de Colby [R.S. Colby, Weeds 15,20-22 ( 1967)] e comparadas com as eficácias observadas. Fórmula de Colby: E eficácia esperada, expressa em % do controle não- tratado, quando do uso da mistura dos compostos ativos A e B nas concentrações a e b x eficácia, expressa em % do controle não-tratado, quando do uso do composto atiwo A na concentração a y eficácia, expressa em % do controle não- tratado, quando do uso do composto ativo B na concentração b.Usage example The synergistic activity of the mixtures according to the invention can be demonstrated by the following experiments: The active compounds were prepared, either together or separately, as an emulsion at 10% concentration in a 63% mixture. cyclohexanone and 27% by weight of emulsifier and diluted to the desired concentration with water respectively. The evaluation was performed by checking the infected leaf surfaces as a percentage. These percentage values were converted to efficiencies. Efficacy (W) was determined according to Abbot's formula as follows: α corresponds to fungal infection of treated plants in% and β corresponds to fungal infection of untreated plants (control) in% An efficacy of 0 corresponds to at a level of infestation of treated plants corresponding to that of untreated plants; At 100, the treated plants show no sign of infestation. The expected efficacy of the active compound mixtures was determined according to Colby's formula [R.S. Colby, Weeds 15,20-22 (1967)] and compared with the observed efficiencies. Colby's formula: Expected efficacy, expressed as% of untreated control, when using active compound A and B mixture at concentrations a and bx efficacy, expressed as% of untreated control, when using atiwo A compound at concentration ay efficacy, expressed as% of untreated control, when using active compound B at concentration b.
Exemplo de Uso 1: Atividade contra o míldeo do trigo causada por Erysiphe [syn. Blumeria] graminis forma especial triíici Folhas de mudas de trigo da espécie Kanzler, desenvolvidas em vasos, foram pulverizadas com da preparação de composto ativo aquosa,abaixo indicada, até o escorrimento. A suspensão ou emulsão foi preparada a partir de uma solução base com 10% de composto ativo em uma mistura composta de hexanona, 20% de agente de umectação e 10% de agente de emulsificação. 24 horas após a secagem da solução de cobertura, as mesmas foram pulverizadas com esporos de míldeo do trigo (Erysiphe [sin. Blumeria] graminis forma especial íriticis). As plantas de teste foram a seguir secadas em uma estufa, regulada em uma temperatura de 20 a 24° C e em uma umidade relativa de 60 a 90%. Após 7 dias, a extensão do desenvolvimento do míldeo de trigo foi avaliada visualmente como um % da área foliar total infectada.Usage Example 1: Activity against wheat mildew caused by Erysiphe [syn. Blumeria] graminis special form triíici Kanzler leaves of seedlings of wheat, developed in pots, were sprayed with the preparation of aqueous active compound, shown below, until draining. The suspension or emulsion was prepared from a base solution containing 10% active compound in a hexane compound mixture, 20% wetting agent and 10% emulsifying agent. 24 hours after drying of the cover solution, they were sprayed with wheat mildew spores (Erysiphe [sin. Blumeria] graminis forma especial riticis). The test plants were then dried in a greenhouse set at a temperature of 20 to 24 ° C and a relative humidity of 60 to 90%. After 7 days, the extent of wheat mildew development was visually assessed as a% of the total infected leaf area.
Os valores determinados visualmente para o percentual de áreas foliares infectadas foram convertidos em eficácias como um % do controle não- tratado. Uma eficácia de 0 significa o mesmo nível de doença que no controle não- tratado, uma eficácia de 100 correspoonde a 0% de infestação. As eficácias esperadas para as combinações de composto ativo foram determinadas de acordo com a fórmula de Colby acima e comparadas com as eficácias observadas.Visually determined values for the percentage of infected leaf areas were converted to efficacies as a% of untreated control. An efficacy of 0 means the same level of disease as in untreated control, an effectiveness of 100 corresponds to 0% infestation. Expected efficacies for the active compound combinations were determined according to the Colby formula above and compared with the observed efficiencies.
Tabela 1 Tabela 2 *)eficácia calculada de acordo com a fórmula de Colby. A partir dos resultados de teste, pode ser observado que a eficácia é mais elevada em todas as razões de mistura do que o grau de eficácia previamente calculado usando a fórmula de Colby. (de Synerg 173. XLS).Table 1 Table 2 *) Efficacy calculated according to Colby's formula. From the test results, it can be seen that efficacy is higher in all mixing ratios than the degree of efficacy previously calculated using Colby's formula. (from Synerg 173. XLS).
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