PT108561A - HERBICIDE MIXTURE - Google Patents

HERBICIDE MIXTURE Download PDF

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Publication number
PT108561A
PT108561A PT108561A PT10856115A PT108561A PT 108561 A PT108561 A PT 108561A PT 108561 A PT108561 A PT 108561A PT 10856115 A PT10856115 A PT 10856115A PT 108561 A PT108561 A PT 108561A
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Prior art keywords
iodosulfuron
salts
diflufenican
florasulam
methyl
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PT108561A
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Portuguese (pt)
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PT108561B (en
Inventor
Manuel Vasconcelos Duarte António
Fernando Trindade Dos Santos Neves José
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Sapec Agro S A
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Priority to PT108561A priority Critical patent/PT108561B/en
Priority to GR20160100245A priority patent/GR1009105B/en
Priority to DE102016007154.0A priority patent/DE102016007154A1/en
Priority to FR1655469A priority patent/FR3037480B1/en
Priority to ITUA2016A004343A priority patent/ITUA20164343A1/en
Priority to ES201630807A priority patent/ES2594177B2/en
Publication of PT108561A publication Critical patent/PT108561A/en
Publication of PT108561B publication Critical patent/PT108561B/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/661,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A PRESENTE INVENÇÃO PROPORCIONA UMA COMPOSIÇÃO HERBICIDA SINÉRGICA COMPREENDENDO UMA MISTURA DE IODOSSULFURÃO-METILO (COMPOSTO I) OU OS SEUS SAIS, FLORASULAME (COMPOSTO II) OU OS SEUS SAIS E DIFLUFENICÃO. A PRESENTE INVENÇÃO TAMBÉM SE REFERE A UM PROCESSO PARA CONTROLAR INFESTANTES DAS CULTURAS DE CEREAIS DE INVERNO E PRIMAVERA POR APLICAÇÃO DA REFERIDA COMPOSIÇÃO.The present invention provides a synergistic herbicidal composition comprising a mixture of methyl isodiphosphorus (Compound I) or its salts, fluorosulfame (Compound II) or its salts and diflulufenium. The present invention also relates to a process for controlling infestation of winter and spring cranberry crops by the application of said composition.

Description

DESCRIÇÃO "MISTURA HERBICIDA"DESCRIPTION "HERBICIDE MIXTURE"

ÁREA DA INVENÇÃOAREA OF THE INVENTION

Esta invenção insere-se na área da proteção das culturas e refere-se especificamente a uma combinação herbicida sinérgica compreendendo iodossulfurão-metilo ou os seus sais, florasulame ou os seus sais e diflufenicão, e à preparação e utilização da referida composição para o controlo de infestantes de culturas de cereais de inverno e primavera.This invention is in the field of crop protection and specifically relates to a synergistic herbicidal combination comprising iodosulfuron-methyl or its salts, florasulam or its salts and diflufenican, and the preparation and use of said composition for the control of weeds from winter and spring cereal crops.

ANTECEDENTES DA INVENÇÃOBACKGROUND OF THE INVENTION

Na área da proteção de culturas, a utilização de uma substância ativa para o controlo de infestantes pode tornar-se cada vez mais dificil ao longo do tempo, resultante do aparecimento de resistências em relação aos herbicidas utilizados. Isto conduz à perda de eficácia no controlo das infestantes e, consequentemente, perda na produção de colheitas e rendibilidade da cultura.In the field of crop protection, the use of an active substance for the control of weeds may become increasingly difficult over time as a result of the emergence of resistance to the herbicides used. This leads to loss of efficacy in controlling weeds and, consequently, loss of crop yield and crop yield.

Uma forma muito desenvolvida de abordagem deste problema consiste na utilização de uma combinação de diferentes substâncias ativas apresentando diferentes mecanismos bioquímicos de ação.A highly developed approach to this problem is the use of a combination of different active substances presenting different biochemical mechanisms of action.

No entanto, a combinação de uma pluralidade de substâncias ativas causa frequentemente problemas de incompatibilidade física ou biológica, que se podem manifestar, por exemplo, na falta de estabilidade física da formulação, degradação de uma ou mais substâncias ativas ao longo do tempo, antagonismo em termos de eficácia biológica ou efeitos de fitotoxicidade na cultura. 0 composto (I), iodossulfurão-metilo (IUPAC: 4-iodo-2-[3-(4-metoxi-6-metil-l,3,5-triazin-2-il)ureidossulfonil]benzoato de metilo), cuja fórmula estrutural é:However, the combination of a plurality of active substances often causes problems of physical or biological incompatibility, which may be manifested, for example, in the lack of physical stability of the formulation, degradation of one or more active substances over time, antagonism in terms of biological effectiveness or phytotoxicity effects on the crop. The compound (I), iodosulfuron-methyl (IUPAC: methyl 4-iodo-2- [3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] benzoate), formula is:

(I) é uma substância herbicida descrita na Patente Europeia EP 0574418.(I) is a herbicidal substance described in EP 0574418.

Utiliza-se preferencialmente o sal de sódio do iodossulfurão-metilo (iodossulfurão-metil-sódio) , que tem a fórmula estrutural (Ia) :The iodosulfuron-methyl sodium salt (iodosulfuron-methyl-sodium), which has the structural formula (Ia), is preferably used:

(Ia) O Iodossulfurão-metil-sódio é uma sulfonilureia que atua inibindo a biossíntese dos aminoácidos essenciais de plantas suscetíveis, através a inibição da enzima acetolactato sintase (ALS). É conhecida a sua utilização em pós-emergência inicial (tanto no que respeita à cultura como às infestantes) em trigo. As ervas daninhas controladas são o azevém (Lolium rigidium), o balanço (Avena spp), Phalaris anual (Phalaris paradoxa) e várias ervas daninhas de folha larga. 0 composto (II), florasulame (IUPAC: 2', 6', 8-trifluoro-5-metoxi[1,2,4]triazolo[1,5-c]pirimidin-2-sulfonanilide) , descrito na Patente Europeia EP 0343752, tem a seguinte fórmula estrutural:(Ia) Iodosulfuron-methyl-sodium is a sulfonylurea that acts by inhibiting the biosynthesis of essential amino acids from susceptible plants by inhibiting the enzyme acetolactate synthase (ALS). Its initial post-emergence (both as far as crops and weeds) use in wheat is known. The controlled weeds are ryegrass (Lolium rigidium), balance (Avena spp), annual Phalaris (Phalaris paradoxa) and various broadleaf weeds. The compound (II), florasulam (IUPAC: 2 ', 6', 8-trifluoro-5-methoxy [1,2,4] triazolo [1,5-c] pyrimidin-2-sulfonanilide), described in EP 0343752, has the following structural formula:

(II) O florasulame é uma triazolopirimidina-sulfonanilida utilizada em pós-emergência em cereais, para controlo de infestantes de folha larga, que atua por inibição da acetolactato sintase (ALS). O composto (III), diflufenicão, (IUPAC: 2r,4r-difluoro-2-(a, a,a-trifluoro-m-toliloxi)nicotinanilide), descrito na Patente Europeia EP 053011, tem a seguinte fórmula estrutural:(II) Florasulam is a triazolopyrimidine sulfonanilide used in post-emergence cereals for the control of broad leaf weeds, which acts by inhibiting acetolactate synthase (ALS). The compound (III), diflufenican (IUPAC: 2R, 4R-difluoro-2- (α, α, α-trifluoro-m-tolyloxy) nicotinanilide) described in European Patent EP 053011 has the following structural formula:

(III) 0 diflufenicão é uma piridina-carboxamida que pode ser utilizada em pré ou pós-emergência em cereais para controlar infestantes de folha larga e que atua inibindo a fitoeno-desidrogenase, uma enzima chave da biossintese de carotenóides, pigmentos que são responsáveis pela absorção da luz para a fotossintese.(III) Diflufenican is a pyridine carboxamide which may be used in pre or post emergence in cereals to control broad leaf weeds and which acts to inhibit phytoene dehydrogenase, a key enzyme of carotenoid biosynthesis, pigments which are responsible for absorption of light for photosynthesis.

Existem documentos de patente que fazem referência à utilização dos ingredientes ativos acima mencionados na composição de misturas herbicidas: A Patente Europeia EP 0831707 BI refere-se a combinações dos ésteres do ácido 4-iodo-2-[(4-metoxi-6-metil-l,3,5-triazin-2-il)carbamoilsulfamoil]benzóico, em particular do iodossulfurão-metilo e dos seus sais, com uma outra substância ativa selecionada de um conjunto que inclui o diflufenicão. A patente apresenta um exemplo de sinergia no combate a Lolium multíflorum, em que a adição de 13 g/ha de diflufenicão (que até uma dose de 25 g/ha não revelou qualquer atividade herbicida) a 10 g/ha de iodossulfurão metilo permitiu obter um aumento de eficácia no controlo da referida infestante de 60 0 pedido de patente EP2095712 AI refere-se a combinações de diflufenicão com florasulame. 0 pedido de patente apresenta um exemplo de sinergia no combate a Lolium multiflorum, em que nem a utilização de 9 g/ha de diflufenicão nem a utilização de 0,5 g/ha de florasulame mostraram qualquer atividade herbicida, mas a combinação de 9 g/ha de diflufenicão com 0,5 g/ha de florasulame permitiu obter uma eficácia de 30 6, 3There are patent documents which refer to the use of the above-mentioned active ingredients in the composition of herbicidal mixtures: European Patent EP 0831707 BI relates to combinations of 4-iodo-2 - [(4-methoxy-6-methyl triazin-2-yl) carbamoylsulfamoyl] benzoic acid, in particular iodosulfuron-methyl and its salts, with another active substance selected from the group consisting of diflufenican. The patent provides an example of synergy in combating Lolium multiflorum in which the addition of 13 g / ha of diflufenican (which up to a dose of 25 g / ha did not show any herbicidal activity) at 10 g / ha of iodosulfuron methyl an increase in effectiveness in controlling said weed of 60 000 patent application EP2095712 AI relates to combinations of diflufenican with florasulam. The patent application provides an example of synergy in combating Lolium multiflorum in which neither the use of 9 g / ha of diflufenican nor the use of 0.5 g / ha of florasulam showed any herbicidal activity, but the combination of 9 g / ha of diflufenican with 0.5 g / ha of florasulam allowed an efficacy of 30.6,

Num aspeto da invenção, o processo é caracterizado por se aplicar 7,5 g/ha a 10 g/ha de iodossulfurão; 3 g/ha a 4 g/ha de florasulame e 60 g/ha a 80 g/ha de diflufenicão.In one aspect of the invention, the process is characterized by applying 7.5 g / ha to 10 g / ha of iodosulfuron; 3 g / ha to 4 g / ha florasulam and 60 g / ha to 80 g / ha diflufenican.

DESCRIÇÃO PORMENORIZADA DA INVENÇÃO O objetivo da presente invenção é proporcionar uma mistura de substâncias ativas herbicidas apresentando elevada eficácia no controlo de infestantes das culturas de cereais de inverno e primavera (trigo duro e mole, cevada, triticale aveia e centeio) selecionadas do grupo compreendendo Anagallis arvensis, Anthemis spp., Galium aparine, Lolium multiflorum, Lolium rigidum, Matricaria chamomilla, Papaver rhoeas, Picris echioides, Poa annua, Rumex crispus, Sinapis arvensis, Stellar ia media e Veronica spp.DETAILED DESCRIPTION OF THE INVENTION The object of the present invention is to provide a mixture of active herbicidal substances exhibiting high effectiveness in weed control of winter and spring cereal crops (durum and soft wheat, barley, triticale oats and rye) selected from the group comprising Anagallis Arvensis, Anthemis spp., Galium aparine, Lolium multiflorum, Lolium rigidum, Matricaria chamomilla, Papaver rhoeas, Picris echioides, Poa annua, Rumex crispus, Sinapis arvensis, Stellar media and Veronica spp.

Constatou-se, de forma surpreendente, que combinando iodossulfurão-metilo (composto I) ou o seu sal de sódio (composto Ia) com florasulame (composto II) e diflufenicão (composto III), se observa um efeito sinérgico na eficácia biológica, que se traduz num acréscimo inesperado de eficácia, quando comparada com a eficácia de cada um dos ingredientes ativos.It has surprisingly been found that combining iodosulfuron-methyl (compound I) or its sodium salt (compound Ia) with florasulam (compound II) and diflufenican (compound III), a synergistic effect on biological efficacy is observed results in an unexpected increase in efficacy when compared to the efficacy of each of the active ingredients.

Este efeito sinergético permite doses de aplicação mais reduzidas ou uma ação herbicida mais potente com as mesmas doses de aplicação, o que se traduz num processo economicamente mais vantajoso para o utilizador e, também, mais favorável do ponto de vista ecológico.This synergistic effect allows for lower application rates or a more potent herbicidal action with the same application rates, which translates into an economically more advantageous to the user and also more environmentally friendly process.

Todas as concentrações das substâncias ativas referidas no presente pedido são expressas como percentagem mássicas ( A formulação pode ser apresentada na forma de pó molhável (WP) , grânulos dispersíveis em água (WG), suspensão aquosa (SC), ou suspensão oleosa (OD).The formulations may be in the form of wettable powder (WP), water dispersible granules (WG), aqueous suspension (SC), or oily suspension (OD) .

As formulações são preparadas de um modo conhecido, por exemplo, por mistura dos compostos ativos com outros formulantes selecionados de entre dispersantes, molhantes, desintegrantes, estabilizantes, corretores de pH e de viscosidade, inertes e suas combinações.The formulations are prepared in a known manner, for example, by blending the active compounds with other inert formulations selected from inert dispersants, wetting, disintegrating, stabilizing agents, pH and viscosity correctors and combinations thereof.

Exemplos de dispersantes preferidos são os lignossulfonatos de sódio ou cálcio (Borresperse pH (por exemplo ácido cítrico) e inertes (por exemplo, sílica ou caulino).Examples of preferred dispersants are sodium or calcium lignosulfonates (Borresperse pH (for example citric acid) and inert (e.g., silica or kaolin).

As doses de aplicação da mistura de acordo com a invenção situam-se na gama de 7,5 g/ha a 10 g/ha de iodossulfurão; 3 g/ha a 4 g/ha de florasulame e 60 g/ha a 80 g/ha de diflufenicão.The application rates of the blend according to the invention are in the range of 7.5 g / ha to 10 g / ha iodosulfuron; 3 g / ha to 4 g / ha florasulam and 60 g / ha to 80 g / ha diflufenican.

Exemplo de formulação A título de exemplo, uma formulação na forma de grânulos dispersíveis em água (WG) é realizada utilizando a seguinte composição e procedimento:FORMULATION EXAMPLE By way of example, a formulation in the form of water dispersible granules (WG) is carried out using the following composition and procedure:

ComponenteComponent

Os compostos Ia, II e III e o cloquintocete-mexilo, são misturados e subsequentemente moídos num moinho de jato de ar, até se obter um tamanho de partícula suficientemente fino (pelo menos 95The compounds Ia, II and III and the cloquintocete-mexil are mixed and subsequently milled in an air jet mill until a sufficiently fine particle size is reached (at least 95% by weight).

Efeito sinérgicoSynergistic effect

Para quantificar o efeito sinérgico resultante da associação das substâncias ativas foi utilizada a metodologia descrita por Colby (Colby, S.R., "Calculating synergistic and antagonistic response of herbicide compositions", Weeds 15, pp 20-22, 1967), de acordo a qual se compara a eficácia esperada (EE) para a mistura dos ingredientes ativos determinada utilizando a fórmula de Colby: EE = x + y - (xy)/100 em que: -EE é a eficácia esperada, em %, utilizando a mistura de compostos ativos A e B nas concentrações a e b. -x é a eficácia, em %, utilizando o composto ativo A na concentração a; -y é a eficácia, em %, utilizando o composto ativo B na concentração b; com a eficácia observada experimentalmente.To quantify the synergistic effect resulting from the association of the active substances, the methodology described by Colby (Colby, SR, "Calculating synergistic and antagonistic response of herbicide compositions", Weeds 15, pp. 20-22, 1967) was used according to which compares the expected efficacy (EE) for the active ingredient mixture determined using the Colby formula: EE = x + y - (xy) / 100 where: -EE is the expected efficacy, in%, using the active compound mixture A and B at concentrations a and b. -x is the efficacy, in%, using the active compound A in concentration a; -y is the efficacy, in%, using the active compound B in concentration b; with the efficacy observed experimentally.

Para uma mistura de três substâncias ativas A, B e C, a referência supracitada apresenta uma modificação da fórmula de Colby segundo a qual a eficácia esperada (EE) é determinada por: EE=x+y+z- (xy+xz+yz)/100 + (xyz)/10000 em que: - x e y são definidos como na fórmula anterior; -z é a eficácia, em %, utilizando o composto ativo C na concentração c. -EE é a eficácia esperada, emFor a mixture of three active substances A, B and C, the abovementioned reference presents a modification of Colby's formula according to which the expected efficacy (EE) is determined by: EE = x + y + z- (xy + xz + yz ) / 100 + (xyz) / 10000 where: - x and y are as defined in the above formula; -z is the efficacy, in%, using the active compound C in concentration c. -EE is the expected efficacy, in

TABELA ATABLE A

efeito sinérgico que se traduz num aumento inesperado de eficácia no combate às infestantes das culturas de cereais de inverno e primavera.synergistic effect resulting in an unexpected increase in effectiveness in combating weeds from winter and spring cereal crops.

Claims (4)

REIVINDICAÇÕES 1. Composição herbicida sinérgica caracterizada por compreender iodossulfurão-metilo ou os seus sais, florasulame ou os seus sais e diflufenicão.A synergistic herbicidal composition comprising iodosulfuron-methyl or its salts, florasulam or its salts and diflufenican. 2. Composição herbicida de acordo com a reivindicação 1, caracterizada por: - a gama de concentração de iodossulfurão se situar entre 4,0 multiflorum, Lolium rigidum, Matricaria chamomilla, Papaver rhoeas, Picris echioides, Poa annua, Rumex crispus, Sinapis arvensis, Stellaria media e Veronica spp.The herbicidal composition according to claim 1, characterized in that: - the concentration range of iodosulfuron is between 4.0 multiflorum, Lolium rigidum, Matricaria chamomilla, Papaver rhoeas, Picris echioides, Poa annua, Rumex crispus, Sinapis arvensis, Stellaria media and Veronica spp. 7. Processo para combater infestantes das culturas de cereais de inverno e primavera (trigo duro e mole, cevada, triticale aveia e centeio), caracterizado por se aplicar sobre estas ou sobre o solo uma mistura de iodossulfurão-metilo ou os seus sais, florasulame ou os seus sais e diflufenicão.Process for combating weeds from winter and spring cereals (durum and soft wheat, barley, triticale oats and rye), characterized in that a mixture of iodosulfuron-methyl or its salts, florasulam or their salts and diflufenican. 8. Processo de acordo com a reivindicação 7, caracterizado por se aplicar 7,5 g/ha a 10 g/ha de iodossulfurão; 3 g/ha a 4 g/ha de florasulame e 60 g/ha a 80 g/ha de diflufenicão.A process according to claim 7, characterized in that 7.5 g / ha is applied to 10 g / ha iodosulfuron; 3 g / ha to 4 g / ha florasulam and 60 g / ha to 80 g / ha diflufenican.
PT108561A 2015-06-16 2015-06-16 HERBICIDE MIXTURE PT108561B (en)

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PT108561A PT108561B (en) 2015-06-16 2015-06-16 HERBICIDE MIXTURE
GR20160100245A GR1009105B (en) 2015-06-16 2016-05-18 Herbicidal mixture
DE102016007154.0A DE102016007154A1 (en) 2015-06-16 2016-06-13 herbicide mixture
FR1655469A FR3037480B1 (en) 2015-06-16 2016-06-14 HERBICIDE MIXTURE
ITUA2016A004343A ITUA20164343A1 (en) 2015-06-16 2016-06-14 HERBICIDE MIXTURE
ES201630807A ES2594177B2 (en) 2015-06-16 2016-06-14 Herbicidal mixture

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