WO2012040804A2 - Combinaisons synergiques de triazoles, strobilurines et de benzimidazoles, leurs utilisations, formulations, leurs procédés de production et leurs applications - Google Patents

Combinaisons synergiques de triazoles, strobilurines et de benzimidazoles, leurs utilisations, formulations, leurs procédés de production et leurs applications Download PDF

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Publication number
WO2012040804A2
WO2012040804A2 PCT/BR2011/000346 BR2011000346W WO2012040804A2 WO 2012040804 A2 WO2012040804 A2 WO 2012040804A2 BR 2011000346 W BR2011000346 W BR 2011000346W WO 2012040804 A2 WO2012040804 A2 WO 2012040804A2
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WIPO (PCT)
Prior art keywords
carbendazim
azoxystrobin
control
flutriafol
tebuconazole
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PCT/BR2011/000346
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English (en)
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WO2012040804A3 (fr
Inventor
Luis Donizete Borges
Leandro Anderlin Garcia
Carlos Eduardo Fabri
Antonio Moreira Lima
Roberta de Fátima DE GODOY
Ricardo Werlang Camara
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Fmc Química Do Brasil Ltda.
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Priority to CA2812427A priority Critical patent/CA2812427C/fr
Priority to US13/876,613 priority patent/US20150051231A1/en
Publication of WO2012040804A2 publication Critical patent/WO2012040804A2/fr
Publication of WO2012040804A3 publication Critical patent/WO2012040804A3/fr

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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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

Definitions

  • the present invention relates to a balanced synergistic combination of active ingredients for controlling diseases in soybean, cotton, corn, beans, wheat, rice, potatoes, tomatoes, citrus and coffee.
  • Fungicide tebuconazole is known by the person skilled in the art for controlling various plant diseases.
  • Patent EP 40 345 provides a description of tebuconazole and some uses. It is a fungicide of the triazole chemical group, and acts by inhibiting the biosynthesis of ergosterol, a substance important for maintaining the integrity of the cell membrane of fungi.
  • Tebuconazole is generally known as (RS)-1-p-chlorophenyl-4,4- dimethyl-3-(1 H-1 ,2,4-triazol-1-ylmethyl)pentan-3-ol and has registration number CAS 107534-96-3. Tebuconazole is described in The Pesticide Manual, page 1072 (entry 808), CDS Thomas, Ed (15 th Ed., 2009).
  • Flutriafol is a fungicide known by the person skilled in the art for controlling various plant diseases.
  • Patent EP 15 756 provides a description of flutriafol and some uses. It is a fungicide of the triazole chemical group, and acts by inhibiting the biosynthesis of ergosterol, a substance important for maintaining the integrity of the cell membrane of fungi.
  • Flutriafol is generally known as (RS)-2,4'-difluoro-a-(1 H-1 ,2,4-triazol-1-ylmethyl)benzhydryl alcohol and has registration number CAS 76674-21-0. Flutriafol is described in The Pesticide Manual, page 560 (entry 422), CDS Thomas, Ed (15 th Ed., 2009).
  • Carbendazim is a fungicide known by the person skilled in the art for controlling various plant diseases. A more detailed description with some uses can be seen in document US 3,010,968. It is a fungicide of the benzimidazole chemical group and acts specifically in cell division by inhibiting the biosynthesis of tubulin, which is a protein that makes up microtubules. Thus, the formation of microtubules is distorted and there is no division of the nucleus and consequent separation.
  • Carbendazim is generally known as 2-methoxybenzimidazol-2-yl)carbamic acid and has registration number CAS 10605-21-7 Carbendazim is described in The Pesticide Manual, page 158 (entry 123), CDS Thomas, Ed (15 th Ed., 2009).
  • Azoxystrobin is a fungicide known by the person skilled in the art for controlling various plant diseases. A more detailed description with some uses can be seen in document EP 382 375. It is a fungicide of the strobilurin chemical group and acts by inhibiting mitochondrial respiration, which blocks the transfer of electrons between cytochrome b and cytochrome c1 , at the Qo site, interfering in the production of ATP.
  • Azoxystrobin is generally known as methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-ethoxyprop- 2-enoate and has registration number CAS 215934-32-0. Azoxystrobin is described in The Pesticide Manual, page 62 (entry 52), CDS Thomas, Ed (15 th Ed., 2009).
  • Kresoxim-methyl is a fungicide known by the person skilled in the art for controlling various plant diseases. A more detailed description with some uses can be seen in document EP 253 213. It is a fungicide of the strobilurin chemical group and acts by inhibiting mitochondrial respiration, which blocks the transfer of electrons between cytochrome b and cytochrome c1 , at the Qo site, interfering in the production of ATP.
  • Kresoxim-methyl is generally known as methyl (E)-methoxyimino[a-(o-tolyloxy)-o-tolyl]acetate and has registration number CAS 143390-89-0. Kresoxim-methyl is described in The Pesticide Manual, page 688 (entry 517), CDS Thomas, Ed (15th Ed., 2009).
  • the present invention can be practiced to control the following diseases, in the following cultures:
  • Soybean crop Cercospora leaf blight (Cercospora kikuchii)
  • Cephalospohoides Cephalospohoides
  • Ramularia Ramulaha areola
  • Alternaria leaf spot Alternaha sp
  • Myrothecium leaf spot Myrothecium rohdum
  • Rust Phakopsora gossypii
  • Corn crop Northern corn leaf blight (Exerohilum turcicum); White spot or phaeosphaeria leaf spot (Phaeosphaeria maydis); Diplodia leaf spot (Diplodia macrospora); Gray leaf spot (Cercospora zea-maydis); Anthracnose (Colletothchum graminicola); Southern rust (Puccinia polysora); Tropical rust (Physopella zeae); Common rust (Puccinia sorghi).
  • Beans crop Blight (Phaeoisariopsis ghseola); Anthracnose
  • Stem rust (Puccinia graminis); Yellow spot (Drechslera tritici-repentis); Helminthosporiosis (Bipolaris sorokiniana); Leaf rust (Puccinia triticina); Blast (Pyricularia grisea); Powdery mildew (Blumeha graminis); Septoria (Septoha tritici).
  • Rice crop Blast (Pyricularia grisea); Brown spot (Bipolaris oryzae).
  • Potato crop Alternaria leaf spot (Alternaha solani).
  • Tomato crop Alternaria leaf spot (Alternaria solani); septoria
  • Citrus crop Anthracnose (Colletothchum gloeosporioides); Alternaria leaf spot (Alternaria citri); Citrus scab (Elsinoe fawcett).
  • Coffee crop Rust (Hemileia vastatrix); Cercosporiosis (Cercospora coffeicola); Anthracnose (Colletothchum coffeanum); Ascochyta (Ascochyta coffeae); Phoma leaf spot (Phoma spp.)
  • Cia & Fuzatto (1999) report about 30 of them occurring in Brazil. Of these, except for seedling pathogens and others of very recent occurrence, about 10 could be considered of primary importance to the cotton culture in the country.
  • the main foliar diseases of cotton in Brazil are: Boll rot (Colletotrichum gossypii van Cephalosporioides); Ramularia (Ramularia areola Atk.) Alternaria leaf spot (Alternaria sp); Myrothecium leaf spot (Myrothecium roridum); Rust (Phakopsora gossypii) (Puccinia cacabata).
  • Corn (Zea mays L.) is also a very important crop in Brazilian agriculture. Its yield can be influenced by such factors as water availability, soil fertility, plant population, crop system, the productive potential of the hybrid and management of weeds, pests and diseases.
  • the stalk rot consist of stem tissue rot evident when plants are close to harvest. Damage is attributed to interruption of the normal grain filling, lodging of plants and premature death of the plant at the end of the cycle.
  • the main leaf spots are the Norhern corn leaf blight caused by the fungus Exerohilum turcicum (Pass.) Leonar & Suggs, the white leaf spot or phaeosphaeria, caused by Phaeosphaeria maydis (P. Henn.) Rae, Payak & Renfro, and diplodia spot, caused by S. macrospora.
  • the gray leaf spot caused by the fungus Cercospora zea-maydis Tenhon & Daniels, stands out, first recorded in the country by Viegas and Krug in 1934, in Campinas, Sao Paulo (Viegas, 1945).
  • Leaf diseases Cercospora leaf blight (Cercospora kikuchii) American rust (Phakopsora meibomiae); Asian soybean rust (Phakopsora pachyrhizi); Alternaria leaf spot (Alternaria sp); Ascochyta blight (Ascochyta sojae); Myrothecium leaf spot ⁇ Myrothecium roridum); Brown spot (Septoria glycines); Frogeye spot (Cercospora sojina); Downy mildew (Peronospora manshurica); Phyllosticta spot (Phyllosticta sojicola); Target spot (Corynespora cassiicola); Soybean blight (Rhizoctonia solani); Powdery mildew (Erysiphe diffusa).
  • Anthracnose Cold-tothchum dematium var. truncata
  • Stem canker Diaporthe phaseolorum f.sp. meridionalis
  • Purple stain Cercospora kikuchii
  • Pod and stem blight Phomopsis spp.
  • Pod blight Fusarium spp.
  • Yeast spot Nematospora corily
  • White stem rot Sclerotinia sclerotiorum
  • other root diseases bacterial diseases, diseases caused by viruses, diseases caused by nematodes and diseases of unknown causes.
  • Asian soybean rust Among the entire complex of soybean diseases, Asian soybean rust deserves special attention due to its high virulence and infection potential, area of occurrence, aggressiveness and high rate of spread.
  • the Asian soybean rust caused by Phakopsora pachyrhizi Sydow has caused significant damage in soybean crops. According to Caldwell & Laing (2005), the inoculum reached the African continent carried by air currents. In South America, it was first described by Morel (2001) in Paraguay, followed by Brazil, Yorinori (2002), Brazil, Argentina and Peru.
  • the damage in the yield has varied between 10 and 85%, mainly in areas where control is not executed or is delayed.
  • Symptoms are particularly evident in the leaves, from isolated uredia to areas with significant coalescence when it causes yellowing and premature leaf abscission. Damages are grouped into brown coloration with two to five uredias and abundant sporulation (B) or the formation of reddish- brown lesions, with zero to two uredias and sparse sporulation (PA) (Bromfield, 984).
  • Fungicides applied preventively have proven to be the most effective strategy in controlling this disease (Azevedo, 2001 ; Hartman et al., 1991). Greater residual period and better performance of the fungicides were obtained by Vitti et al. (2004), due to the preventive application of fungicides. Likewise, Oliveira (2004) found an increase in yield up to 100% when disease control was preventively performed.
  • the classification is usually based on the chemical nature and mode of action of the product.
  • the classification based on the mode of action is: protective with contact action; contact with eradicative action; systemic with systemic and eradicative action; penetrating with depth action and resistance inducers. As for the resistance inducers, there is scant evidence.
  • the protective fungicides prevent the successful penetration of fungi in the host tissue.
  • the class of strobilurin fungicides (azoxystrobin, pyraclostrobin, trifloxystrobin, etc.) has the ability to interrupt spore germination and penetration in the host. However, it has little or no effect after the fungus has penetrated or colonized the host plant tissue.
  • the curative fungicides have the ability to inhibit or stop the development of infections that have already begun. Some fungicides act by inhibiting sporulation which helps to slow down the development of the disease, limiting the reproductive potential of the fungus.
  • Some fungicides act by inhibiting sporulation which helps to slow down the development of the disease, limiting the reproductive potential of the fungus.
  • the triazoles have some curative activity. It is this activity of triazoles that provides limited curative effect in low levels of rust in the field. If one of the strobilurin fungicides is applied after infection, they will continue to develop. It is very important to remember that the triazoles have limited curative action. This is the main reason why fungicides are not effective in controlling soybean rust, in conditions of high or moderate disease pressure in the field.
  • fungicides The mobility of fungicides is differentiated. The main point is that different fungicides, even those in the same chemical class, are not necessarily equal when it comes to mobility within the plant.
  • Systemic fungicides such as triazoles, benzimidazoles and strobilurins, are absorbed by plants and redistributed into the tissues at different levels of mobility.
  • strobilurin fungicides are absorbed and have translaminar translocation, but differences in the systemic circulation have been observed between different strobilurins.
  • pyraclostrobin is a strobilurin that has less mobility than azoxystrobin, which is absorbed by the plant, but it does not move much beyond the absorption point.
  • strobilurin the leaves produced after application are not protected adequately.
  • the triazole fungicides have systemic activity and as a group they tend to be more quickly absorbed and redistributed within the leaf and up (via xylem) for the new developing leaves.
  • a major concern in the association of fungicides is to make use of all the benefits of the molecules employed, such as mode of action of each molecule, differentiated systematicity and stages in which the fungicide provides pathogen control.
  • mode of action of each molecule differentiated systematicity and stages in which the fungicide provides pathogen control.
  • association of fungicides that have different modes of action and that are at different stages of the pathogen has better potential to control plant diseases, which can further result in better residual control.
  • the present invention relates to a synergistic combination of triazoles, strobilurins and benzimidazoles.
  • such combinations include: tebuconazole + carbendazim + azoxystrobin; tebuconazole + carbendazim + kresoxim-methyl; flutriafol + carbendazim + azoxystrobin; flutriafol + carbendazim + kresoxim-methyl.
  • Another object of the invention is to provide a product with the interaction of three fungicides, wherein the combination of fungicide molecules meets the following ratios: tebuconazole (25 to 250g/L); carbendazim (50 to 500g/L), azoxystrobin (5 to 200 g/L), with the possibility of the interaction of fungicide molecules meeting these ratios, which results in products with high efficacy in controlling plant diseases.
  • Another objective of the invention is to reduce the amount of active ingredient per hectare, since the synergism of the molecules of the present invention BF 488 (tebuconazole + carbendazim + azoxystrobin) provides application of smaller amounts of actives per ha of carbendazim and azoxystrobin.
  • Another important factor of the invention is to increase the residual effect of the fungicides in product BF 488, compared with tebuconazole applied alone or with azoxystrobin applied alone, this prolonged effect resulting in greater efficacy in controlling diseases.
  • Another important factor of the invention is to increase the spectrum of disease control in crops with the application of product BF 488 (tebuconazole + carbendazim + azoxystrobin), with no need to mix the products in the spray tank and to have the immediate re-entry in the area with another product.
  • product BF 488 tebuconazole + carbendazim + azoxystrobin
  • This fact is a function of the synergistic association of three modes of action of fungicides, the triazoles - which are highly effective in controlling Ascomycetes and Basidiomycetes, and have some action in Deuteromycetes; the benzimidazoles - which are highly effective in controlling Deuteromycetes and have some action in controlling Ascomycetes and Basidiomycetes; and strobilurins - which are highly effective in controlling Deuteromycetes and have some action in controlling Oomycetes and Basidiomycetes and have little activity in Ascomycetes.
  • product BF 488 tebuconazole + carbendazim + azoxystrobin
  • Another object of the invention is to provide a product with the interaction of three fungicides, coded as "BF 452", wherein the combination of fungicide molecules meets the following ratios: tebuconazole (25 to 250g/L); carbendazim (50 to 500g/L), kresoxim-methyl (50 a 500g/L), with the possibility of the interaction of fungicide molecules meeting these ratios, which results in products with high efficacy in controlling plant diseases.
  • BF 452 is a balanced and synergistic (pre-mix), particularly having the concentration of tebuconazole (100g/L ai) + carbendazim (200 g/L ai) + kresoxim-methyl (125g/L ai), for controlling a broad spectrum of diseases in soybean, cotton, corn, beans, wheat, rice, potato, tomato, citrus and coffee crops.
  • Another objective of the invention is to reduce the amount of active ingredient per hectare, since the synergism of the molecules of the present invention BF 452 (tebuconazole + carbendazim + kresoxim-methyl) provides the application of smaller amounts of actives per ha of carbendazim and kresoxim-methyl.
  • Another important factor of the invention is to increase the residual effect of the fungicides in product BF 452, compared with tebuconazole applied alone or with kresoxim-methyl applied alone, this prolonged effect resulting in greater efficacy in controlling diseases.
  • Another important factor of the invention is to increase the spectrum of disease control in crops with the application of product BF 452 (tebuconazole + carbendazim + kresoxim-methyl), with no need to mix the products in the spray tank and to have the immediate re-entry in the area with another product.
  • product BF 452 tebuconazole + carbendazim + kresoxim-methyl
  • This fact is a function of the synergistic association of three modes of action of fungicides, the triazoles - which are highly effective in controlling Ascomycetes and Basidiomycetes, and have some action in Deuteromycetes; the benzimidazoles - which are highly effective in controlling Deuteromycetes and have some action in controlling Ascomycetes and Basidiomycetes; and strobilurins - which are highly effective in controlling Deuteromycetes and have some action in controlling Oomycetes and Basidiomycetes and have little activity in Ascomycetes.
  • product BF 452 (tebuconazole + carbendazim + kresoxim-methyl) will be an important tool in the management of disease resistance to fungicides, being a mixture of three different active chemical groups and modes of action.
  • Another object of the invention is to provide a product with the interaction of three fungicides, coded as "BF 452", wherein the combination of fungicide molecules meets the following ratios: flutriafol (25 to 250g/L); carbendazim (50 to 500g/L), azoxystrobin (5 to 200 g/L), with the possibility of the interaction of fungicide molecules meeting these ratios, which results in products with high efficacy in controlling plant diseases.
  • BF 489 is a balanced and synergistic (pre-mix), particularly having the concentration of flutriafol (63 g/L ai) + carbendazim (200 g/L ai) + azoxystrobin (30 g/L ai), for controlling a broad spectrum of diseases in soybean, cotton, corn, beans, wheat, rice, potato, tomato, citrus and coffee crops.
  • Another objective of the invention is to reduce the amount of active ingredient per hectare, since the synergism of the molecules of the present invention BF 489 (flutriafol + carbendazim + azoxystrobin) provides application of smaller amounts of actives per ha of carbendazim and azoxystrobin.
  • Another important factor of the invention is to increase the residual effect of the fungicide product BF 489, compared with flutriafol applied alone or with azoxystrobin applied alone, this prolonged effect resulting in greater efficacy in controlling diseases.
  • Another important factor of the invention is to increase the spectrum of disease control in crops with the application of product BF 489 (flutriafol + carbendazim + azoxystrobin), with no need to mix the products in the spray tank and to have immediate re-entry in the area with another product.
  • product BF 489 flutriafol + carbendazim + azoxystrobin
  • This fact is a function of the synergistic association of three modes of action of fungicides, the triazoles - which are highly effective in controlling Ascomycetes and Basidiomycetes, and have some action in Deuteromycetes; the benzimidazoles - which are highly effective in controlling Deuteromycetes and have some action in controlling Ascomycetes and Basidiomycetes; and strobilurins - which are highly effective in controlling Deuteromycetes and have some action in controlling Oomycetes and Basidiomycetes and have little activity in Ascomycetes.
  • Another important factor of the invention referring to product BF 489 flutriafol + carbendazim + azoxystrobin
  • product BF 489 flutriafol + carbendazim + azoxystrobin
  • Another object of the invention is to provide a product with the interaction of three fungicides, coded as "BF 465", wherein the combination of fungicide molecules meets the following ratios: flutriafol (25 to 250g/L); carbendazim (50 to 500g/L), kresoxim-methyl (50 a 500g/L), with the possibility of the interaction of fungicide molecules meeting these ratios, which results in products with high efficacy in controlling plant diseases.
  • BF 465 is a balanced and synergistic (pre-mix), particularly having the concentration of flutriafol (63 g/L ai) + carbendazim (200 g/L ai) + kresoxim-methyl (125g/L ai), for controlling a broad spectrum of diseases in soybean, cotton, corn, beans, wheat, rice, potato, tomato, citrus and coffee crops.
  • Another objective of the invention is to reduce the amount of active ingredient per hectare, since the synergism of the molecules of the present invention BF 465 (flutriafol + carbendazim + kresoxim-methyl) provides application of smaller amounts of actives per ha of carbendazim and kresoxim-methyl.
  • Another important factor of the invention is to increase the residual effect of the fungicide product BF 465, compared with flutriafol applied alone or with kresoxim-methyl applied alone, this prolonged effect resulting in greater efficacy in controlling diseases.
  • Another important factor of the invention is to increase the spectrum of disease control in crops with the application of the product BF 465 (flutriafol + carbendazim + kresoxim-methyl), with no need to mix the products in the spray tank and to have the immediate re-entry in the area with another product.
  • This fact is a function of the synergistic association of three modes of action of fungicides, the triazoles - which are highly effective in controlling Ascomycetes and Basidiomycetes, and have some action in controlling Deuteromycetes; the benzimidazoles - which are highly effective in controlling Deuteromycetes and have some action in controlling Ascomycetes and Basidiomycetes; and strobilurins - which are highly effective in controlling Deuteromycetes and have some action in controlling Oomycetes and Basidiomycetes and have little activity in Ascomycetes.
  • the present invention relates to a solid or liquid formulation, wherein, in the solid form, it is suitable as wettable powder type (WP) and/or water-dispersible granules (WDG) and, in the liquid form, it is suitable as emulsifiable concentrate (EC), suspension concentrate (SC), suspo-emulsion (SE) and/or concentrated emulsion (EW), preferably as SC, but not excluding other types of formulations.
  • WP wettable powder type
  • WDG water-dispersible granules
  • EC emulsifiable concentrate
  • SC suspension concentrate
  • SE suspo-emulsion
  • EW concentrated emulsion
  • the formulations comprise the mixture of chemical groups benzimidazole, triazole and strobilurin.
  • the active ingredients and their proportions are shown below.
  • Tebuconazole and Azoxystrobin is 10 to 30 parts of Carbendazim, 5 to 15 parts of Tebuconazole and 1 to 5 parts of Azoxystrobin, and, in a particularity of the invention, the optimum ratio is 20:10:3, respectively.
  • the ratio of the amount of Carbendazim, Flutriafol and Azoxystrobin is 10 to 30 parts of Carbendazim, 4 to 8 parts of Flutriafol and 1 to 5 parts of Azoxystrobin, and, in a particularity of the invention, the optimum ratio is 20:6.25:3, respectively.
  • the ratio of the amount of Carbendazim, Tebuconazole and Krezoxim-Methyl is 10 to 30 parts of Carbendazim, 5 to 15 parts of Tebuconazole and 6 to 18 parts of Krezoxim-Methyl, and, in a particularity of the invention, the optimum ratio is 20: 0:12.5, respectively.
  • the ratio of the amount of Carbendazim, Flutriafol and Krezoxim-Methyl is 10 to 30 parts of Carbendazim, 4 to 8 parts of Flutriafol and 6 to 18 parts of Krezoxim-Methyl, and, in a particularity of the invention, the optimum ratio is 20:6.55:12.5, respectively.
  • the remainder of the composition up to 1 (one) liter, if liquid, or 1 (one) kilogram, if solid, can be comprised of a suitable carrier and/or excipients, which can be selected from the group consisting of surfactants, defoamers , rheology modifying agents, dispersants, humectants, bactericides or bacteriostatic agents, anti-caking agents, stabilizing agents, antifreezing agents, among others, and the mixture thereof.
  • the vehicle might normally be inert, made of organic or inorganic material, natural or synthetic.
  • the carrier if solid, can be clay, silicates, silica, resins, waxes, cellulose fibers, fertilizers or the like, and might be used alone or in combination.
  • the carrier can be water, C1 to C14 alcohols, glycols, acetates, ketones, glycerids, saturated or unsaturated hydrocarbons, fatty acid esters, vegetable oils, mineral oils, or the like, and might be used alone or in combination.
  • water is used as vehicle.
  • the surfactants can be either of ionic, non-ionic, cationic or polymeric type.
  • Anionic surfactants that can be used in this invention could be: dodecylbenzene sulphonic acid, linear or branched, under the acid or neutralized form, nitrogenous derivates, sulfonated aromatic polymers under the acid or neutralized form, sulphonated naphthalene formaldehydes under the acid or neutralized form, condensed or not, lignosulfonates, alkyl-phenol phosphate under the acid or neutralized form. Being these, preferably, ethoxylated tristyryl-phenol-phosphate or not under the acid or neutralized form and the lignosulfonates.
  • Non-ionic surfactants that can be used in this invention could be:
  • Alkoxylates like alkoxylated sorbitan esters, alkoxylated alcohols, alkoxylated vegetable oils, alkoxylated fatty acids, among others; fatty esters like polyethylene glycol esters, glycerol or polyglycerol esters, sorbitan esters; amides, like fatty acid amide of ethanolamine or ethylene amines, fatty imidazolines, among others.
  • alkoxylated alcohols with capric, caprylic, isodecylic, isotridecylic, decylic, lauric, stearylic, oleic, nonyl phenylic chains, with alkoxylation degree of 1 to 16 moles of ethene oxide and/or propene oxide, are used; alkoxylated vegetable oils like alkoxylated castor bean oil with alkoxylation degree between 5 and 54 moles of ethene oxide or propene oxide; alkoxylated sorbitan esters with alkoxylation degree between 5 and 80 moles of ethene oxide and/or propene oxide.
  • Cationic surfactants that can be used in this invention are alkyl trimethyl ammonium hydrochlorides, dialkyl dimethyl ammonium hydrochloride, alkyl hydroxyethyl dimethyl ammonium hydrochloride, cetyl trimethyl ammonium hydrochloride, distearyl dimethyl ammonium hydrochloride, quaternary esters, among others.
  • Polymeric surfactants that can be used in this invention are ethene oxide and propene oxide block copolymers, mainly those with butylic chain, polyacrylate copolymers, methyl methacrylate copolymers, among others.
  • the present invention also relates to a process for preparing the formulations, such as, for instance, the Concentrated Suspension formulation, which includes the following steps:
  • synergistic agrochemical formulations obtained above are then packed or wrapped in packages commonly used in the art.
  • a further embodiment of the invention is the use of benzimidazole, triazole e strobilurin in the preparation of formulations to control and/or combat pests and diseases in vegetable crops.
  • the invention also comprises the use of the formulations of the invention in controlling and/or combating plagues and diseases in vegetable cultures.
  • Another embodiment of the invention is a method of controlling and/or combating plagues and diseases in vegetable cultures, comprising the application of the formulations of the invention on these plagues, their habitats and/or vegetable cultures.
  • the invention has wide and effective applicability in vegetable cultures of soybean, cotton, com, beans, wheat, rice, potato, tomato, citrus and coffee, among others, in controlling and combating plagues caused by Alternaria citri, Alternaria solani, Alternaria sp, Ascochyta coffeae, Ascochyta sojae, Bipolaris oryzae, Bipolaris sorokiniana, Blumeria graminis, Cercospora coffeicola, Cercospora kikuchii, Cercospora sojina, Cercospora zea-maydis, Colletotrichum coffeanum, Colletotrichum dematium var.
  • formulations of the invention are employed in a single, sequential or simultaneous application.
  • Example 3 Formulation of the invention (BF488): (Components) [concentration (g/100mL mL)]
  • Example 5 Formulation of the invention (BF489): (Components) [concentration (g/100mL mL)]
  • Methyl metacrylate copolymer 1.0 Benzisotiazolin 0.25
  • Example 15 Use of the formulations of the invention in soybean, coffee, rice and cotton crops to control and/or treat diseases/pests:
  • benzimidazole acting on the integrity of tubulin
  • triazole sterol synthesis inhibitor
  • ergosterol is the major lipid component of the plasma membrane of fungi, acting in inhibiting the formation of ergosterol
  • strobilurin which inhibits mitochondrial respiration by blocking the transfer of electrons in the complex cytochrome BC1 Qo site, interfering with the formation of ATP.
  • the fungicides applied alone were not effective in controlling soybean rust, as can be observed by the high area under the disease- progress curve for azoxystrobin even at the dose of 60 g/ha ai or kresoxim- methyl at the dose of 125 g/ha ai. (See Table 1 below), carbendazim even at a dose of 250 g/ha ai, and tebuconazole at the dose of 100g/ha ai. The low control efficacy resulted in lower crop productivity. The association tebuconazole + carbendazim (100 + 200 g/ha ai, respectively) was not effective in controlling soybean rust.
  • azoxystrobin from 6 g/ha ai in the mixture of tebuconazole + carbendazim has already reflected in rust efficacy gain, providing control similar to the efficacy standard of azoxystrobin + cyproconazole (60 + 24 g/ha ai, respectively), and this product is marketed by Syngenta as PrioriXtra®.
  • the addition of azoxystrobin in doses of 18, 24 and 30 g/ha ai together with tebuconazole + carbendazim was effective for obtaining yields higher than the market standard containing 60 g/ha of azoxystrobin.
  • Table 1 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Phakopsora pachyrhizi Sydow. Rondonopolis - MT.
  • azoxystrobin from 6 g/ha ai in the mixture of flutriafol + carbendazim (62.5 + 200 g/ha ai, respectively) has already reflected in rust efficacy gain, providing control similar to the efficacy standard of azoxystrobin + cyproconazole (60 + 24 g/ha ai, respectively), and this product is marketed by Syngenta as PrioriXtra®.
  • the addition of azoxystrobin in doses of 18, 24 and 30 g/ha ai together with flutriafol + carbendazim was effective for obtaining yields higher than the market standard containing 60 g/ha of azoxystrobin.
  • E the expected reduction in disease development (such as the reduction in the percentage of expected control or the reduction in the area under the disease-progress curve)
  • x and y represent the reduction in disease development achieved by treatment with fungicide x and y, respectively.
  • the possible interaction responses are:
  • antagonism which is characterized by joint action of two fungicides showing the response of a test organism in their combination that is lower than the expected response, obtained by appropriate reference models, as proposed by Colby (1967) ;
  • synergism which is the cooperative action of two fungicides showing a response in the test organism on the joint application that is higher than the expected response obtained by appropriate reference models
  • additive which occurs when two fungicides react by presenting a response in the test organism on the joint application that is equal to the expected response obtained by appropriate reference models
  • the association tebuconazole + carbendazim + azoxystrobin (100 + 200 + 30 g/ha ai, respectively) provided a synergistic effect in their interaction in the control of soybean rust, as shown in Table 3 below.
  • This synergistic interaction was effective in controlling the disease, both in the bottom leaves and in the top leaves of the soybean plant.
  • the synergism in disease control in the bottom leaves reflects high control efficacy, since the products used reach the leaves in smaller amounts at this position, and the disease has a better condition for its development.
  • the association tebuconazole + carbendazim + kresoxim-methyl (100 + 200 + 125 g/ha ai, respectively) provided a synergistic effect in its interaction in the control of soybean rust, as shown in Table 3 below.
  • This synergistic interaction was effective in controlling the disease, both in the bottom leaves and in the top leaves of the soybean plant.
  • the synergism in disease control in the bottom leaves reflects high control efficacy, since the products used reach the leaves in smaller amounts at this position and the disease has a better condition for its development.
  • Table 3 - Effective control of Phakopsora pachyrhizi obtained by area under the disease-progress curve (AUDPC) in the lower canopy and upper canopy due to interactions of fungicides and expected control (Colby).
  • the association flutriafol + carbendazim + azoxystrobin (62.5 + 200 + 30 g/ha ai, respectively) provided a synergistic effect in its interaction in the control of soybean rust, as shown in Table 4 below.
  • This synergistic interaction was effective in controlling the disease, both in the bottom leaves and in the top leaves of the soybean plant.
  • the synergism in disease control in the bottom leaves reflects high control efficacy, since the products used reach the leaves in smaller amounts at this position and the disease has a better condition for its development.
  • the association flutriafol + carbendazim + kresoxim-methyl (62.5 + 200 + 125 g/ha ai, respectively) provided a synergistic effect in its interaction in the control of soybean rust, as shown in Table 4 below.
  • This synergistic interaction was effective in controlling the disease, both in the bottom leaves and in the top leaves of the soybean plant.
  • the synergism in disease control in the bottom leaves reflects high control efficacy, since the products used reach the leaves in smaller amounts at this position and the disease has a better condition for its development.
  • association of azoxystrobin with tebuconazole and carbendazim or the association of kresoxim-methyl with tebuconazole and carbendazim provide highly effective control of rust (see Table 1 above) and this interaction has a synergistic effect (see Table 3 above).
  • association of the three fungicides - tebuconazole, carbendazim and azoxystrobin or tebuconazole, carbendazim and kresoxim- methyl provides greater safety regarding protection against the emergence of fungi resistant to fungicides and improved control spectrum.
  • the increase in the control spectrum can be seen in Table 5 below by the highly effective control of target spot (Corynespora cassiicola) and anthracnose (Colletotrichum truncatum).
  • Table 5 Average results of target spot severity (Corynespora cassiicola) and anthracnose (Colletotrichum truncatum) 14 days after the third application in view of fungicide interactions. Rondonopolis - MT.
  • Target spot (Corynespora cassiicola) ** anthracnose (Colletotrichum truncatum)
  • association of azoxystrobin with flutriafol and carbendazim or the association of kresoxim-methyl with flutriafol and carbendazim provide highly effective control of rust (see Table 2 above) and this interaction has a synergistic effect (see Table 4 above).
  • association of the three fungicides - flutriafol, carbendazim and azoxystrobin or flutriafol, carbendazim and kresoxim-methyl provides greater safety regarding protection against the emergence of fungi resistant to fungicides and improved control spectrum.
  • the increase in the control spectrum can be seen in Table 5 above by the highly effective control of target spot (Corynespora cassiicola) and anthracnose (Colletotrichum truncatum).
  • the soybean target spot is caused by fungus Corynespora cassiicola (Berk. & M.A. Curtis) C. T. Wei.
  • This pathogen was first identified in the U.S. in 1945 under the name Helminthosporium vignae. In Brazil, the first records were in 1974 in the states of Mato Grosso and Parana in 1976 (Almeida et al., 1976).
  • the fungus is found in virtually all regions of soybean cultivation in Brazil, and it is considered to be native and infect a large number of plant species. It can survive in crop residues and infected seeds, which is one way of spreading. Conditions of high humidity and warm temperatures are conducive to leaf infections. The most common symptoms are leaf spots with yellow halo and dark spots in the center, causing severe defoliation. Spots also occur on the stem and pod. The fungus can also infect roots, causing root rot and intensive sporulation (Henning et al., 2005).
  • Anthracnose is a major disease in the crop at all stages of development from seedling stage to the early stage of pod filling, which makes it an important problem in the cerrado region. In rainy years, it can cause total loss of production, with significant reduction in the number of pods (Yorinori, 1997).
  • the fungicides applied alone were not effective in controlling target spot and anthracnose in soybean crops, as can be observed by the high severity of the disease for azoxystrobin even at the dose of 60 g/ha ai or kresoxim-methyl at the dose of 125 g/ha ai. (See Table 5 above).
  • azoxystrobin with the flutriafol + carbendazim mixture provided a control efficacy gain and a residual control effect even under high pressure of target spot and anthracnose. This higher control effect is observed by the lower severity of the diseases (see Table 5 above).
  • the addition of azoxystrobin from 6 g/ha ai in the mixture of flutriafol + carbendazim (62.5 + 200 g/ha ai, respectively) has already reflected in the efficacy gain of target spot and anthracnose, providing more control than the efficacy standard of azoxystrobin + cyproconazole (60 + 24 g/ha ai, respectively) (PrioriXtra®).
  • the association of the three fungicides tebuconazole, carbendazim and azoxystrobin provides effective control of target spot (Corynespora cassiicola) and anthracnose (CoHetotrichum truncatum) (see Table 5 above), and contains fungicides with three modes of action - carbendazim (benzimidazole) - acting on the integrity of tubulin; tebuconazole (triazole) - sterol synthesis inhibitors; azoxystrobin (strobilurin) - inhibits mitochondrial respiration.
  • the association of the three fungicides tebuconazole, carbendazim and kresoxim-methyl provides effective control of target spot ⁇ Corynespora cassiicola) and anthracnose (CoHetotrichum truncatum) (see Table 5 above), and contains fungicides with three modes of action - carbendazim (benzimidazole) - acting on the integrity of tubulin; tebuconazole (triazole) - sterol synthesis inhibitors; azoxystrobin (strobilurin) - inhibits mitochondrial respiration.
  • association of azoxystrobin with flutriafol and carbendazim or the association of kresoxim-methyl with flutriafol and carbendazim provide highly effective control of rust (see Table 2 above).
  • the addition of azoxystrobin and kresoxim-methyl to flutriafol and carbendazim provides a synergistic effect in the control of Asian rust.
  • the association of the three fungicides flutriafol, carbendazim and azoxystrobin or flutriafol, carbendazim and kresoxim-methyl provides effective control of target spot (Corynespora cassiicola) and anthracnose (Colletotrichum truncatum) (see Table 5 above), and contains fungicides with three modes of action - carbendazim (benzimidazole) - acting on the integrity of tubulin; flutriafol (triazole) - sterol synthesis inhibitors; azoxystrobin and kresoxim-methyl (strobilurin) - inhibits mitochondrial respiration.
  • product BF 488 (tebuconazole 100 + carbendazim 200 + azoxistrobin 30) is compared with market standard commercial products PrioriXtra® (Syngenta) and Opera® (Basf) (see Tables 7 and 9 below).
  • Product BF 488 is effective in controlling soybean rust, being better than industry standards.
  • BF 488 provided better control of rust on the botton, median and top leaves of the soybean plant, reflected by high efficacy and better residual control.
  • product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125) is compared with market standard commercial products PrioriXtra® (Syngenta) and Opera® (Basf) (see Tables 8 and 9 below).
  • the BF 452 is effective in controlling soybean rust, being better than industry standards.
  • Product BF 452 provided better control of rust on the botton, median and top leaves of the soybean plant, reflected by high efficacy and better residual control.
  • product BF 465 flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125
  • PrioriXtra® Synera
  • Opera® Basf
  • Product BF 465 is effective in controlling soybean rust, being similar to industry standards.
  • the BF 465 provided excellent control of rust on the botton, median and top leaves of the soybean plant, reflected by high efficacy and better residual control.
  • product BF 489 flutriafol 62.5 + carbendazim 200 + azoxystrobin 30
  • PrioriXtra® Synera
  • Opera® Basf
  • Product BF 489 is effective in controlling soybean rust, even under high disease pressure, being better than industry standards.
  • BF 489 provided better control of rust on the botton, median and top leaves of the soybean plant, reflected by high efficacy and better residual control.
  • septoria Septoria glycines
  • gray leaf spot Cercospora kikuchii
  • white mold Sclerotinia sclerotiorum
  • This synergistic interaction provides the increment of the disease control spectrum in crops with the application of products BF 488 (tebuconazole + carbendazim + azoxystrobin), BF 489 (flutriafol + carbendazim + azoxystrobin), BF 452 (tebuconazole + carbendazim + kresoxim-methyl) and BF 465 (flutriafol + carbendazim + kresoxim-methyl), with no need to mix the products in the spray tank, and to have the immediate re-entry into the area with another product.
  • This fact is a function of the synergistic association of three modes of action of fungicides, triazoles - which are highly effective in controlling Ascomycetes and Basidiomycetes, and have some action in controlling Deuteromycete; benzimidazoles - which are highly effective in controlling Deuteromycetes and have some action in controlling Ascomycetes and Basidiomycetes; and strobilurins - which are highly effective in controlling Deuteromycetes and have some action in controlling Oomycetes and Basidiomycetes and little activity in Ascomycetes.
  • cephalosporioides (Tables 32 and 33 below); Ramularia ⁇ Ramularia areola Atk.) (Tables 29, 30 and 31 below); Alternaria spot ⁇ Alternaria sp); Myrothecium ⁇ Myrothecium roridum); Rust ⁇ Phakopsora gossypii) ⁇ Puccinia cacabata).
  • Example 16 Efficacy of BF 488 and BF 489 in the control of Phakopsora pachyrhizi Sydow in soybean crops, Santa Helena de Goias/GO, 2009/2010 crop: This study was conducted to evaluate the efficacy of the products in the control of Asian soybean rust. Preventive applications started in R1 , with the second application occurring 20 days after the first application and the third application 15 days after the second. Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added, and Fox, in which Aureo was added at the dose of 0.4 L/ha.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30) and product BF 489 (flutriafol 62.5 + carbendazim 200 + azoxystrobin 30) are effective in controlling soybean rust (Table 10 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488 and BF 489 is consistent, reducing the disease throughout the soybean plant canopy. Analyzing the AUDPC of the bottom leaves, the best treatments were BF 488, BF 489, Fox and PrioriXtra, demonstrating higher mobility and/or higher residual efficacy of these fungicides.
  • Example 17 Efficacy of BF 452 and BF 465 in the control of Phakopsora pachyrhizi Sydow in soybean crops. Rio Verde/GO, 2008/2009 crop.
  • Product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125) and product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125) are effective in controlling soybean rust (Table 11 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 452 and BF 465 is consistent, reducing the disease throughout the soybean plant canopy. Analyzing the AUDPC of the bottom leaves, the best treatments were BF 452, BF 465 and Opera, demonstrating higher mobility and/or higher residual efficacy of these fungicides.
  • Table 1 1 - Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Phakopsora pachyrhizi, Rio Verde - GO. Treatment AUDPC Productivity
  • Example 18 Efficacy of BF 452, BF 465, BF 488 and BF 489 in the control of Phakopsora pachyrhizi Sydow in soybean crops, Goiania/GO. 2009/2010 crop.
  • Product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125); product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30); product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125) and product BF 489 (flutriafol 62,5 + carbendazim 200 + azoxystrobin 30) are effective in controlling soybean rust (Table 12 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • BF 452, BF 465, BF 488 and BF 489 The efficacy of BF 452, BF 465, BF 488 and BF 489 is consistent, reducing the disease throughout the soybean plant canopy. Analyzing the AUDPC of the bottom leaves, the best treatments were BF 452, BF 488, BF 489 and PrioriXtra, demonstrating higher mobility and/or higher residual efficacy of these fungicides. Analyzing the AUDPC of the top leaves, the best treatments were BF 452, BF 465, BF 488, BF 489, PrioriXtra and Opera, demonstrating the high activity of these fungicides in controlling the disease. The best yields were observed in treatments with BF 452, BF 465, BF 488, BF 489, Opera and PrioriXtra. Tebuconazole applied alone was not effective in controlling soybean rust.
  • Example 19 Efficacy of BF 488 in the control of Phakopsora pachyrhizi Sydow in soybean crops, Goiania/GO, 2009/2010 crop.
  • Analyzing the AUDPC of the bottom leaves the best treatments were BF 488, BF 489, Fox and ApproachPrima, demonstrating higher mobility and/or higher residual efficacy of these fungicides.
  • Analyzing the AUDPC of the top leaves the best treatments were BF 488, BF 489 and AproachPrima, demonstrating the high activity of these fungicides in controlling the disease. The best yields were observed in treatments with BF 488, BF 489, Opera, , PrioriXtra, Opera, AproachPrima and Fox. Tebuconazole applied alone was not effective in controlling soybean rust.
  • Example 20 Efficacy of BF 488 in the control of Phakopsora Septoria glycines in soybean crops, Goiania/GO, 2009/2010 crop.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30) is effective in controlling Septoria glycines (Table 14 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488 is consistent, reducing the disease throughout the soybean plant canopy. Disease severity was high as can be observed in the untreated control with 54% severity 48 days after the second application (DA2A). Analyzing the severity of septoriosis at 17 DA2A, the best treatments were BF 488, and PrioriXtra and PrioriXtra + Portero. However, in the assessment of severity at 58 DA2A, BF 488 maintains better control. The better control efficacy and the maintenance of a residual effect of BF 488 can be observed in the lower AUPDC values.
  • Table 14 Area under the disease-progress curve (AUDPC) and severity in function of the interactions of fungicides for the control of Septoria glycines, Goiania - GO.
  • AUDPC disease-progress curve
  • Example 21 Efficacy of BF 488 in the control of Cercospora kikuchii n soybean crops, Goiania/GO, 2009/2010 crop.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30) is effective in controlling Cercospora kikuchii (Table 15 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488 is consistent, reducing the disease throughout the soybean plant canopy. Disease severity was high as can be observed in the untreated control with 29% severity 48 days after the second application (DA2A). Analyzing the severity of cercosporiosis at 29 DA2A, the best treatments were BF 488, Portero, PrioriXtra and PrioriXtra + Portero. However, in the assessment of severity at 58 DA2A, BF 488 has better control. The better control efficacy and the maintenance of a residual effect of BF 488 can be observed in the lower AUPDC values.
  • Table 15 Area under the disease-progress curve (AUDPC) and severity in function of the interactions of fungicides for the control of Cercospora kikuchii, Goiania - GO.
  • AUDPC disease-progress curve
  • the test was conducted in randomized blocks design, with four replications. This was carried out in Barreiras-BA, in the 2009/2010 crop, in cultivar M-Soy 9144RR.
  • the start of fungicide application occurred 25 days after crop emergence (DAE), with the second application occurring 35 DAE and the third application 15 days afterwards in R2.
  • DAE crop emergence
  • fungicides BF 488 tebuconazole 100 + carbendazim 200 + azoxystrobin 30
  • BF 452 tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125
  • Frowncide and Sumilex were effective in controlling the disease, and do not show any differences (Table 16 below).
  • analyzing the soybean yield it is noted that there is no difference between these fungicides, and that they were effective in controlling Sclerotinia sclerotiorum in soybean crops.
  • Example 23 Efficacy of BF 488 in the control of Puccinia sorghi e Colletotrichum graminicola in corn crops, Sao Desiderio/BA, 2009/2010 crop:
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30) and product BF 489 (flutriafol 62.5 + carbendazim 200 + azoxystrobin 30) are effective in controlling Puccinia sorghi and Colletotrichum graminicola (Tabela 17), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488 and BF 489 is consistent, reducing the disease throughout the corn plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease-progress curve, which resulted in lower productivity.
  • Table 17 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Puccinia sorghi and Colletotrichum graminicola in corn crops, Sao Desiderio - BA.
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 24 Efficacy of BF 488 in the control of Physophella zeae in corn crops, Goiania/GO, 2009/2010 crop.
  • Table 18 Area under the disease-progress curve (AUDPC) in function of the interactions of fungicides for the control of Physopella zeae in corn crops, Goiania - GO.
  • AUDPC disease-progress curve
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 25 Efficacy of BF 488 in the control of Colletotrichum graminicola in corn crops, Goiania/GO, 2009/2010 crop.
  • BF 488 is consistent, reducing the disease throughout the corn plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease- progress curve, which resulted in lower productivity. BF 488 is effective in controlling C. graminicola.
  • Table 19 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Colletotrichum graminicola in corn crops, Goiania - GO.
  • AUDPC disease-progress curve
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 26 Efficacy of BF 488 in the control of Puccinia polysora in corn crops, Goiania/GO, 2009/2010 crop. This study was conducted to evaluate the efficacy of the prodcuts in the control of Southern rust in corn crops. It was installed in corn DKB 390 YG. Preventive fungicide applications started on the 5 th leaf, and the second application was made before corn tasseling. Emulsifiable mineral oil Assist was added at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30) is effective in controlling Puccinia polysora (Table 20 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488 is consistent, reducing the disease throughout the corn plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease-progress curve, which resulted in lower productivity.
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 27 Efficacy of BF 452, BF 465, BF 489 and BF 488 in the control of Cercospora zeae-maydis, Helminthosporium maydis, Puccinia sorghi and Phaeosphaeria maydis in corn crops. Summary of the three studies. Santa Helena de Goias/GO, 2009/2010 crop.
  • Emulsifiable mineral oil Assist was added at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30); product BF 489 (flutriafol 62.5 + carbendazim 200 + azoxystrobin 30); product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125) and product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125) are effective in controlling Cercospora zeae-maydis, Helminthosporium maydis, Puccinia sorghi and Phaeosphaeria maydis (Tables 21 , 22, 23 and 24 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488, BF 489, BF 452 and BF 465 is consistent, reducing the disease throughout the corn plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease-progress curve, which resulted in lower productivity. The efficacy of products BF 488, BF 489, BF 452 and BF 465 is consistent, improving corn productivity.
  • Table 21 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Cercospora zeae-maydis in corn crops, Santa Helena de Goias - GO.
  • AUDPC disease-progress curve
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Table 22 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Helminthosporium maydis in corn crops, Santa Helena de Goias - GO .
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Table 23 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Puccinia sorghi in corn crops, Santa Helena de Goias - GO.
  • AUDPC disease-progress curve
  • Phaeosphaeria maydis in corn crops, Santa Helena de Goias - GO.
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 28 Efficacy of BF 452, BF 465, BF 489 and BF 488 in the control of Colletotrichum graminicola in corn crops, Luis Eduardo Magalhaes/BA, 2009/2010 crop.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30); product BF 489 (flutriafol 62,5 + carbendazim 200 + azoxystrobin 30); product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125); and product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125) are effective in controlling Colletotrichum graminicola (Table 25 below), providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • the efficacy of BF 488, BF 489, BF 452 and BF 465 is consistent, reducing the disease throughout the corn plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease-progress curve, which resulted in lower productivity. The efficacy of products BF 488, BF 489, BF 452 and BF 465 is consistent, improving corn productivity.
  • Emulsifiable mineral oil Assist was added, at the dose of 0.5% v/v in all treatments, except for the PrioriXtra treatments, in which 0.5% v/v Nimbus was added.
  • Example 29 Summary of three tests to assess the efficacy of BF in 488 in the control of spots in irrigated rice crops, Pelotas/RS, 2009/2010 crop.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30); product BF 489 (flutriafol 62.5 + carbendazim 200 + azoxystrobin 30); product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125) and product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim- methyl 125) are effective in controlling leaf spots (Table 26) providing excellent residual control that can be observed by the smaller area under the disease-progress curve.
  • BF 488, BF 489, BF 452 and BF 465 The efficacy of BF 488, BF 489, BF 452 and BF 465 is consistent, reducing the disease throughout the rice plant canopy. Disease severity was high as can be observed in the untreated control by the large area under the disease-progress curve, which resulted in lower productivity.
  • Example 30 Summary of two tests to assess the efficacy of BF 488, BF 489, BF 452 and BF 465 in the control of spots in upland rice crops, Sao Desiderio/BA and Sinop/MT, 2009/2010 crop.
  • Product BF 488 (tebuconazole 100 + carbendazim 200 + azoxystrobin 30); product BF 489 (flutriafol 62.5 + carbendazim 200 + azoxystrobin 30); product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125); and product BF 465 (flutriafol 62.5 + carbendazim 200 + kresoxim- methyl 125) are effective in controlling leaf spots - rice blast (Tables 27 and 28), providing excellent residual control that can be observed by the lower severity of the rice blast.
  • BF 488, BF 489, BF 452 and BF 465 The efficacy of BF 488, BF 489, BF 452 and BF 465 is consistent, reducing the disease throughout the rice plant canopy and improving the health of panicles. Disease severity was high as can be observed in the untreated control by the high severity, which resulted in lower productivity.
  • Products BF 488, BF 489, BF 452 and BF 465 are effective in improving rice productivity.
  • Table 27 Severity of rice blast (Pyricularia grisea) - Study carried out to assess the efficacy of BF 488, BF 489, BF 452 and BF 465 in the control of spots in upland rice crops, Sinop/MT.
  • Example 31 Efficacy of BF 489 and BF 465 in the control of
  • the test was conducted in randomized blocks design, with four replications. This study was carried out in Luis Eduardo Magalhaes-BA, in the 2009/2010 crop, in cultivar Delta Opal.
  • the applications started 45 days after crop emergence (DAE) and the other applications occurred at 60, 75 and 90 DAE.
  • DAE crop emergence
  • the severity of ramularia was high and the productivity of the untreated control was 32% lower than that obtained in the best management practices with fungicides.
  • Product BF 465 flutriafol 62.5 + carbendazim + 200 + kresoxim-methyl 125
  • product BF 489 flutriafol 62.5 + carbendazim 200 + azoxystrobin 30
  • Ramularia areola Table 29
  • Example 32 Efficacy of tebuconazole + carbendazim + azoxystrobin in the control of Ramularia areola in cotton crops.
  • the test was conducted in randomized blocks design, with four replications. This study was carried out in Santa Helena de Goias - GO, in the 2008/2009 crop, in cultivar Delta Opal. The applications started 45 days after crop emergence (DAE) and the other applications occurred at 60, 75 and 90 DAE. The severity of ramularia was high and the productivity of the untreated control was 36.5% lower than that obtained in the best management practices with fungicides.
  • Product BF 452 (tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125) and product tebuconazole 100 + carbendazim 200 + azoxystrobin 18 are effective in controlling Ramularia areola (Table 30), providing excellent residual control that can be seen by the smaller area under the curve of disease progress.
  • the efficacy of the synergistic mixtures BF 452 and tebuconazole + carbendazim + azoxystrobin is consistent, reducing the disease throughout the cotton plant canopy and improving cotton productivity.
  • Table 30 Area under the disease-progress curve (AUDPC) and yield in function of the interactions of fungicides for the control of Ramularea areola in cotton crops, Santa Helena de Goias - GO.
  • AUDPC disease-progress curve
  • Example 33 Efficacy of BF 452 and BF 465 in the control of Ramulaha areola in cotton crops, Luis Eduardo Magalhaes/BA, 2008/2009 crop.
  • the test was conducted in randomized blocks design, with four replications. This study was carried out in Luis Eduardo Magalhaes-BA, in the 2008/2009 crop, in cultivar Delta Opal. The applications started 45 days after crop emergence (DAE) and the other applications occurred at 60, 75 and 90 DAE. The severity of ramularia was high and the productivity of the untreated control was 36% lower than that obtained in the best management practices with fungicides.
  • Product BF 465 flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125
  • BF 452 tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125
  • the efficacy of the synergistic mixtures BF 452 and BF 465 is consistent, reducing the disease throughout the cotton plant canopy and ensuring productivity gain.
  • Example 34 Efficacy of BF 452, BF 465 and tebuconazole + carbendazim + azoxystrobin in the control of Colletotrichum gossypii var. cephalosporioides in cotton crops, Santa Helena de Goias/GO, 2008/2009 crop.
  • the test was conducted in randomized blocks design, with four replications. This study was carried out in Santa Helena de Goias - GO, in the 2008/2009 crop, in cultivar BRS Ipe.
  • the applications started 45 days after crop emergence (DAE) and two days after inoculation with a suspension of spores at the concentration of 105 conidia/mL.
  • the other applications occurred at 60, 75 and 90 DAE.
  • the severity of ramulosis was high and the productivity of the untreated control was 58.2% lower than that obtained in the best management practices with fungicides.
  • Product BF 465 flutriafol 62.5 + carbendazim 200 + kresoxim-methyl 125
  • BF 452 tebuconazole 100 + carbendazim 200 + kresoxim-methyl 125
  • product tebuconazole 100 + carbendazim 200 + azoxystrobin 18 are effective in controlling Colletotrichum gossypii var. cephalosporioides (Table 32), providing excellent residual control that can be seen by the lower disease score observed thoughout the assessment.
  • Example 35 Efficacy of BF 465 and BF 489 in the control of
  • Colletotrichum gossypii var. cephalosporioides in cotton crops Santa Helena de Goias/GO, 2009/2010 crop.
  • the test was conducted in randomized blocks design, with four replications. This study was carried out in Santa Helena de Goias - GO, in the 2009/2010 crop, in cultivar BRS Ipe.
  • the applications started 45 days after crop emergence (DAE) and two days after inoculation with a suspension of spores at the concentration of 105 conidia/mL.
  • the other applications occurred at 60, 75 and 90 DAE.
  • the severity of ramulosis was high in the experiment.
  • Product BF 465 flutriafol 62.5 + carbendazim 200 + kresoxim- methyl 125
  • Product BF 489 flutriafol 62.5 + carbendazim 200 + azoxystrobin 30
  • Table 33 Colletotrichum gossypii var. cephalosporioides
  • Table 32 Severity score (scale of 1 to 5) and productivity in function of the interactions of fungicides in the control of Colletotrichum gossypii var. cephalosporioides in cotton crops, Santa Helena de Goias/GO.
  • Example 36 Summary of two studies - Efficacy of BF 465 and BF 452 in the control of coffee rust (Hemileia vastatrix) in coffee crops, Espirito Santo do Pinhal/SP, 2009/2010 crop.

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Abstract

La présente invention concerne une formulation agrochimique synergique comprenant des triazoles, des strobilurines et des benzimidazoles, dans des proportions spécifiques, et destinée à l'élimination et/ou à la lutte contre les invasions d'acridiens et les maladies qu'ils provoquent dans les cultures. L'invention concerne également un procédé de préparation et l'utilisation de ladite formulation, et un procédé d'utilisation ainsi que l'utilisation des triazoles, des strobilurines et des benzimidazoles dans la préparation de la formulation agrochimique synergique de l'invention.
PCT/BR2011/000346 2010-09-29 2011-09-26 Combinaisons synergiques de triazoles, strobilurines et de benzimidazoles, leurs utilisations, formulations, leurs procédés de production et leurs applications WO2012040804A2 (fr)

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US13/876,613 US20150051231A1 (en) 2010-09-29 2011-09-26 Synergistic combinations of triazoles, strobilurins and benzimidazoles, uses, formulations, production processes and applications using the same

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BRPI1003373 BRPI1003373A2 (pt) 2010-09-29 2010-09-29 combinaÇÕes sinÉrgicas de triazàis, estrobirulinas e benzimidazàis, usos, formulaÇÕes, processos de produÇço e aplicaÇÕes utilizando a mesma
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WO2012162846A1 (fr) 2011-06-03 2012-12-06 Suncor Energy Inc. Émulsions huile paraffinique dans eau utilisables en vue de la lutte contre les infections par des champignons pathogènes chez les plantes cultivées
WO2015062358A1 (fr) * 2013-10-30 2015-05-07 Rotam Agrochem International Company Limited Procédé destiné à augmenter le rendement par traitement avec des compositions fongicides
US9226504B2 (en) 2010-09-09 2016-01-05 Suncor Energy Inc. Synergistic paraffinic oil and boscalid fungicides
US9357768B2 (en) 2006-10-05 2016-06-07 Suncor Energy Inc. Herbicidal composition with increased herbicidal efficacy
US9485988B2 (en) 2008-06-26 2016-11-08 Suncor Energy Inc. Turfgrass fungicide formulation with pigment
US9999219B2 (en) 2004-05-18 2018-06-19 Suncor Energy Inc. Spray oil and method of use therof for controlling turfgrass pests
EP3420819A4 (fr) * 2016-06-26 2019-08-28 Jiangsu Huifeng Bio Agriculture Co., Ltd. Composition bactéricide
US11433070B2 (en) 2019-06-28 2022-09-06 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11701316B2 (en) 2020-12-18 2023-07-18 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11980612B2 (en) 2020-06-26 2024-05-14 The Procter & Gamble Company Synergistic anti-inflammatory compositions

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US9999219B2 (en) 2004-05-18 2018-06-19 Suncor Energy Inc. Spray oil and method of use therof for controlling turfgrass pests
US9801369B2 (en) 2006-10-05 2017-10-31 Suncor Energy Inc. Herbicidal composition with increased herbicidal efficacy
US9357768B2 (en) 2006-10-05 2016-06-07 Suncor Energy Inc. Herbicidal composition with increased herbicidal efficacy
US9826738B2 (en) 2008-06-26 2017-11-28 Suncor Energy Inc. Turfgrass fungicide formulation with pigment
US9485988B2 (en) 2008-06-26 2016-11-08 Suncor Energy Inc. Turfgrass fungicide formulation with pigment
US9226504B2 (en) 2010-09-09 2016-01-05 Suncor Energy Inc. Synergistic paraffinic oil and boscalid fungicides
US9750249B2 (en) 2010-09-09 2017-09-05 Suncor Energy Inc. Synergistic paraffinic oil and boscalid fungicides
US9451773B2 (en) 2011-06-03 2016-09-27 Suncor Energy Inc. Paraffinic oil-in-water emulsions for controlling infection of crop plants by fungal pathogens
WO2012162846A1 (fr) 2011-06-03 2012-12-06 Suncor Energy Inc. Émulsions huile paraffinique dans eau utilisables en vue de la lutte contre les infections par des champignons pathogènes chez les plantes cultivées
EP2713749A1 (fr) * 2011-06-03 2014-04-09 Suncor Energy Inc. Émulsions huile paraffinique dans eau utilisables en vue de la lutte contre les infections par des champignons pathogènes chez les plantes cultivées
EP2713749A4 (fr) * 2011-06-03 2014-11-12 Suncor Energy Inc Émulsions huile paraffinique dans eau utilisables en vue de la lutte contre les infections par des champignons pathogènes chez les plantes cultivées
WO2015062358A1 (fr) * 2013-10-30 2015-05-07 Rotam Agrochem International Company Limited Procédé destiné à augmenter le rendement par traitement avec des compositions fongicides
CN105705019A (zh) * 2013-10-30 2016-06-22 龙灯农业化工国际有限公司 通过用杀真菌组合物处理增加产量的方法
CN105705019B (zh) * 2013-10-30 2021-06-15 龙灯农业化工国际有限公司 通过用杀真菌组合物处理增加产量的方法
US10004231B2 (en) 2013-10-30 2018-06-26 Rotam Agrochem International Company Limited Method of increasing yield by treating with fungicidal compositions
EP3420819A4 (fr) * 2016-06-26 2019-08-28 Jiangsu Huifeng Bio Agriculture Co., Ltd. Composition bactéricide
AU2016413017C1 (en) * 2016-06-26 2020-04-30 Adama Huifeng (Jiangsu) Ltd. Bactericide composition
AU2016413017B2 (en) * 2016-06-26 2020-01-23 Adama Huifeng (Jiangsu) Ltd. Bactericide composition
US11433070B2 (en) 2019-06-28 2022-09-06 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11980612B2 (en) 2020-06-26 2024-05-14 The Procter & Gamble Company Synergistic anti-inflammatory compositions
US11701316B2 (en) 2020-12-18 2023-07-18 The Procter & Gamble Company Synergistic anti-inflammatory compositions

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