WO2007123531A1 - Fongicide/BACTÉRICIDE À base de cuivre - Google Patents

Fongicide/BACTÉRICIDE À base de cuivre Download PDF

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Publication number
WO2007123531A1
WO2007123531A1 PCT/US2006/015394 US2006015394W WO2007123531A1 WO 2007123531 A1 WO2007123531 A1 WO 2007123531A1 US 2006015394 W US2006015394 W US 2006015394W WO 2007123531 A1 WO2007123531 A1 WO 2007123531A1
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WO
WIPO (PCT)
Prior art keywords
weight
copper
dispersant
combinations
composition according
Prior art date
Application number
PCT/US2006/015394
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English (en)
Inventor
Alfonso Gutierrez Martinez
Laura Elizabeth Bailon Cisneros
Pablo Diaz Toledo
Raul Salazar Franco
Original Assignee
Albaugh, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Albaugh, Inc. filed Critical Albaugh, Inc.
Priority to PCT/US2006/015394 priority Critical patent/WO2007123531A1/fr
Priority to AU2006342524A priority patent/AU2006342524A1/en
Priority to EP06751193A priority patent/EP2012590A1/fr
Publication of WO2007123531A1 publication Critical patent/WO2007123531A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper

Definitions

  • the present invention relates generally to fungi cides/bactericides. More specifically, the present invention relates to a fungicide/bactericide composition which is based upon a complex of copper and a carboxylic acid derivative, and a method of making and using the fungicide/bactericide composition.
  • Fungi are a large group of nongreen plants dependent upon the organic food made by photosynthesizing green plants. They represent a constant and ever present threat to many agricultural crops ranging from tropical and semi-tropical vegetation to temperate climate crops. Thus the control of phytopathogenic fungi is of great economic importance since fungal growth on plants or on parts of plants inhibits production of foliage, fruit or seed, and the overall quality of a cultivated crop. In addition, certain groups of fungi produce mycotoxins in infected crops, directly posing a health hazard to humans and animals. Fungicides are known in the art as either chemical or biological agents used to mitigate, inhibit or destroy fungi. To be economical, the cost of controlling plant diseases must be offset by increased crop yield and quality.
  • Dry flowable products are generally dustless, free-flowing, granular products. They are popular among users because the products can be formulated with a higher percentage of active ingredient, are easy to use and have improved shelf life compared to the aqueous fungicides/bactericides. Dry bactericides/fungicides can be stored for a long period of time, over wide extremes of temperature, without destroying the stability of the formulation. Dry bactericides/fungicides formulations also result in lower shipping cost.
  • Biological activity of the copper-based fungicides/bactericides is measured by the free Cu 2+ ions available for consumption by the fungi or bacteria.
  • the biological activity of a fungicide/bactericide increases with an increase in the amount of free Cu 2+ ions released. Therefore, the fungicides/bactericides formulated based on water insoluble copper compounds are normally applied in relatively large amounts to effectively control the phytopathogenic fungi. As a result, the relatively high level of copper detracts from cost effectiveness, contributes to soil residue contamination and raises the potential for phytotoxicity.
  • the water insoluble copper compounds can be milled to fine particle size to increase the surface area of the compounds.
  • the finer the copper compound the more surface area it can cover with relatively small amounts of copper compounds.
  • the methods employed to reduce the particle size of the copper compounds are not always cost effective.
  • it is difficult to disperse the finely milled copper compounds because of the tendency of fine particles to agglomerate.
  • U.S. Patent No. 6,139,879 describes an aqueous bactericide/fungicide containing a complex of copper and ethylenediamine-di-o-hydroxyphenylacetic acid (EDDHA).
  • EDDHA ethylenediamine-di-o-hydroxyphenylacetic acid
  • U.S. Patent No. 6,471,976 describes an aqueous bactericide/fungicide containing a complex of copper and a partially neutralized polycarboxylic acid. While the bactericides/fungicides reduce the usage of copper compounds, the bioavailable copper from the complexes based on copper hydroxide ranges only from 217 ppm to 3530 ppm (see Table 1 and Table 2).
  • U.S. Patent 6,562,757 describes a plant-protection composition comprising a copper source in non-chelated form and sparingly soluble calcium, zinc or manganese chelate. Upon application of the composition, copper chelates are formed in situ and gradually released to extend the application interval.
  • U.S. Patent 6,562,757 also describes a process of making the claimed composition by mixing and milling all the dry and powdery ingredients. While the gradual release of Cu 2+ ions may be advantageous, it is desirable for a fungicide/bactericide to have an effective initial Cu 2+ ion concentration to provide immediate antifungal/antibacterial effect. It is also desirable to have a process of making a fungicide/bactericide substantially dust-free.
  • the present invention is directed to an improved copper-based fungicide/bactericide composition.
  • the improved composition offers higher biological activity over typical copper-based products, while requiring significantly less copper in the composition.
  • the improved copper-based fungicide/bactericide composition of present invention comprises: (a) between about 30.0% to about 90.0% by weight (based on the total weight of all dry ingredients) of a copper compound; (b) between about 0.2% and about 10.0% by weight of a water soluble carboxylic acid derivative; (c) up to about 15.0% by weight of a first dispersant, wherein said first dispersant is selected from the group consisting of a block copolymer non-ionic surfactant having an average molecular weight of between about 1,000 and 15,000, a polycarboxylic acid derivative having a pH of between about 5 and about 10 and an average molecular weight of between about 1,000 and about 37,000, and combinations thereof; (d) between about 0.5% and about 60.0% by weight of a filler; (e) up to about 10.0% by weight of a second dispersant, wherein said second dispersant is selected from the group consisting of lignin sulfonate, naphthalenesulfonate
  • the present invention is also directed to a method of making the improved copper-based fungicide/bactericide composition.
  • the method comprises: (a) combining between about 30.0% to about 90.0% by weight (based on the total weight of all dry ingredients) of a copper compound wet cake having about 40 to about 60 % solid content with, (i) between about 0.2% and about 10.0% by weight of a water soluble carboxylic acid derivative, (ii) up to about 15.0% by weight of a first dispersant, wherein said first dispersant is selected from the group consisting of a block copolymer non-ionic surfactant having an average molecular weight of between about 1,000 and about 15,000, a polycarboxylic acid derivative having a pH of between about 5 and about 10 and an average molecular weight of between about 1,000 and about 37,000, and combinations thereof, (iii) between about 0.5% and about 60.0% by weight of a filler, (iv) up to about 10.0% by weight of a second dispersant, wherein said second
  • the present invention is further directed to a method of using the improved copper-based fungicide/bactericide composition.
  • the method comprises applying to the plants an effective amount of fungicide/bactericide composition of the invention.
  • the present invention relates to an improved copper-based fungicide/bactericide composition and a method of making and using the same.
  • the improved composition offers higher biological activity over typical copper-based products, while requiring significantly less copper in the composition.
  • the decreased copper content reduces the residual fungicide in the soil, and thus reduces the potential for phytotoxicity.
  • the fungicide/bactericide composition of present invention contains a copper complex that is substantially less phytotoxic and more effective against fungi in comparison to typical copper compounds.
  • the improved composition releases and disperses free Cu 2+ ions up to 10 times more than that of typical copper-based formulations.
  • the present invention releases about 25,000 ppm (parts per million) of Cu 2+ ions from a copper hydroxide based fungicide/bactericide, compared to about 2,500 ppm of Cu 2+ ions from typical copper hydroxide based fungicides/bactericides.
  • a fungicide/bactericide formulation may be produced in accordance with the present invention by mixing between 30.0% to 90.0% by weight (based on the total weight of all dry ingredients) of a copper compound wet cake with, (i) between 0.2% and 10.0% by weight of a water soluble carboxylic acid derivative, (ii) up to about 15.0% by weight of a first dispersant, wherein said first dispersant is selected from the group consisting of a block copolymer non-ionic surfactant having an average molecular weight of between about 1,000 and about 15,000, a polycarboxylic acid derivative having a pH of between about 5 and about 10 and an average molecular weight of between about 1,000 and about 37,000, and the combinations thereof, (iii) between 0.5% and 60.0% by weight of a filler, (iv) up to about 10.0% by weight of a second dispersant, wherein said second dispersant is selected from the group consisting of lignin sulfonate, naphthalenes
  • the copper compounds useful in the present invention include copper hydroxide, copper oxychloride, tribasic copper sulfate, basic copper carbonate and copper oxide.
  • the preferred copper compounds are copper hydroxide, copper oxychloride and tribasic copper sulfate.
  • the copper oxychloride wet cake may be produced by mixing metallic copper with hydrochloric acid and water to form copper oxychloride; passing the reaction mixture through a rotary filter to dewater and obtain the copper oxychloride wet cake having about 40-60% solid content, more preferably having about 45-55% solid content, most preferably having about 50% solid content.
  • the copper hydroxide wet cake may be produced by mixing copper oxychloride with caustic soda to form copper hydroxide; and passing the reaction mixture through a rotary filter to dewater and obtain the copper hydroxide wet cake having about 40-60% solid content, more preferably having about 45-55% solid content, most preferably having about 50% solid content.
  • the tribasic copper sulfate wet cake may be produced by mixing copper hydroxide with sulfuric acid to form tribasic copper sulfate; and passing the reaction mixture through a rotary filter to dewater and obtain the tribasic copper sulfate wet cake having about 40-60% solid content, more preferably having about 45-55% solid content, most preferably having about 50% solid content.
  • the water soluble carboxylic acid derivatives useful in the present invention include water soluble metal and ammonium salts of citric acid, malic acid, fumaric acid, succinic acid, glutaric acid, adipic acid, and the like.
  • the preferred water soluble carboxylic acid derivatives are alkali metal salts of citric acid, malic acid, fumaric acid, succinic acid, glutaric acid and adipic acid, and the like.
  • the most preferred water soluble carboxylic acid derivative is sodium citrate available from Jungbunzlauer Austria AG in Pemhofen, Austria.
  • the block copolymer non-ionic surfactants useful in the present invention include non-ionic surfactants used in emulsifiable and suspension concentrates.
  • Suitable block copolymers are polyalkylene oxide block copolymers having a molecular weight of between about 1,000 to about 15,000.
  • the preferred block copolymer non-ionic surfactant is Toximul ® 8323 available from Stephan Company, Illinois, U.S.A.
  • the polycarboxylic acid derivatives useful in the present invention include polyacrylic acid derivatives.
  • the polyacrylic acid derivatives can be prepared by neutralizing polyacrylic acids having a molecular weight of between about 1,000 and 37,000, preferably between about 5,000 and about 37,000.
  • the polyacrylic acid is neutralized to a pH of between about 5 and about 10 by adding to the polyacrylic acid a neutralizing agent.
  • Suitable neutralizing agents include sodium hydroxide, potassium hydroxide, NaHCO 3 , Na 2 CO 3 and the like.
  • the preferred polyacrylic acid derivative is Orotan ® 850, available from Rohm and Haas Company, Pennsylvania, U.S.A.
  • Orotan ® 850 is a sodium salt of polyacrylic acid.
  • Suitable polycarboxylic acids useful in the present invention include polymethacrylic acids; copolymers of acrylic acid and acrylamide, methacrylamide, acrylate esters (methyl, ethyl and butyl), methacrylic acid, methacrylate esters (methyl and ethyl) and maleic anhydride; carboxymethylcellulose; and maleic acid polymers and copolymers with butadiene and maleic anhydride.
  • block copolymer non-ionic surfactants and polycarboxylic acid derivatives may be used alone or in combination to achieve the optimal results.
  • Fillers for granules, wettable powders, dry flowables of copper-based fungicide/bactericide are known in the art. Suitable fillers include diatomaceous earth, calcium carbonate, calcium bentonite clay and sodium bentonite clay.
  • Lignin sulfonates and naphthalenesulfonates useful as dispersants are known in the art.
  • the preferred lignin sulfonate is available under the trade name Wanin ® DP 734 FI, a sodium salt of lignin polymer. It is available from Borregaard Lignotech, Finland.
  • the preferred naphthalenesulfonate is available under the trade name Morwet ® D-425, a sodium salt of naphthalene sulfonate condensate. It is available from Akzo Nobel Surface Chemistry LLC, Texas, U.S.A. Lignin sulfonates and naphthalenesulfonates may be used alone or in combination to achieve the optimal results.
  • the copper based fungicide/bactericide compositions can optionally include other formulation additives, such as wetting agents, antifoam agents and stabilizers.
  • the wetting agents, antifoaming agents and stabilizers are known in the art.
  • the preferred wetting agent is Genapol ® X060, a fatty alcohol polyglycol ether non-ionic surfactant, available from Clariant Corporation of Charlotte, North Carolina, U.S.A.
  • the preferred antifoam agent is AF ® 365 Antifoam, a polydimethysiloxane antifoam emulsion, available from General Electric of Greenwich, Connecticut, U.S.A.
  • the preferred stabilizer is glycerol.
  • the wetting agents, antifoam agents and stabilizers can each be incorporated into the compositions in amounts between about 0.01% and about 1.50% by weight (based on the total weight of all dry ingredients). They may be used alone or in combination to achieve the optimal results.
  • the slurry can be air dried, oven dried or spray dried.
  • the slurry is spray dried to form a dry flowable granular product by using a spray dryer equipped with an atomizer.
  • the spray drying chamber has an inlet temperature of about 300 0 C, and an outlet temperature of about 90 0 C.
  • the resulting granular product has moisture content of less than about 4.0%, preferably less than about 2.0%.
  • the resulting granular product has an average particle size of less than about 8 microns, preferably less than about 6 microns, more preferably less than about 4 microns.
  • the fungicide/bactericide compositions of the present invention can be prepared in other forms, such as flakes, powders, tablets, pellets and solutions.
  • the fungicide/bactericide compositions are tested for biocopper.
  • biocopper means free Cu 2+ ions available for consumption by the fungi or bacteria.
  • the “biocopper” value can be measured by Atomic Absorption Spectropliotometric methods as described below:
  • Centrifuge about 50 ml of the suspension at 3000 rpm for 20 minutes; filter about 35 ml of the supernatant liquid on a 13 mm Millipore filter; transfer 25 ml of the filtrate to a 50 ml volumetric flask; add 1 ml of concentrated nitric acid and make up to the mark with de-ionized water; mix and measure the absorbance; and read off the concentration of q ( ⁇ g/ml) of copper from the calibration curve.
  • Biocopper [q /(50 x W)] %, wherein W is the sample weight (gram).
  • the fungicide/bactericide compositions of the present invention may be applied directly to the leaves of a plant at a rate of preferably between about 0.5 and about 12.0 pounds per acre depending on the specific plants to be protected or treated.
  • the fungicide/bactericide compositions of the present invention may also be mixed with water and then sprayed onto the plants using conventional agricultural sprayers and spraying techniques known in the art.
  • the mixing ratio of granulates and water is between about 2:10,000 (w/w) and 5:1,000, more preferably between about 3:10,000 and about 2:1,000, and most preferably 5:10,000.
  • the rate of spray application is preferably between about 10 to 165 gallons per acre depending on the specific plants to be protected or treated.
  • the fungicide ⁇ actericide compositions of the present invention is useful for treating bacterial and fungal diseases on various plants including citrus, such as grapefruit, lemon, lime, orange, tangelo and tangerine; field crops, such as alfalfa, oats, peanuts, potatoes, sugar beets, wheat, and barley; small fruits, such as blackberry, blueberry, cranberry, currant, gooseberry, raspberry and strawberry; tree crops, such as almond, apple, apricot, avocado, banana, cacao, cherry, coffee, filberts, litchi, mango, nectarine, olive, peach, pear, pecan, plum, pistachio, prune, sugar apple and walnut; vegetables, such as bean, broccoli, brussel sprout, cabbage, cantaloupe, carrot, cauliflower, celery, collards, cucumber, eggplant, honeydew, lettuce, muskmelon, onion, pea, pepper, pumpkin, squash, spinach, tomato, watercress and watermelon; vines, such as
  • the fungicide/bactericide composition of the present invention is useful for treating plants with fungal or bacterial diseases, such as melanose, scab, pink pitting, greasy spot, brown rot, phytophthora, citrus canker, xanthomonas and cerospora leaf spots, black leaf spot (alternaria), alternaria blight, blossom blight, botrytis blight, powdery mildew, xanthomonas leaf spot, leaf and cane spot, anthracnose, pseudomonas leaf spot, septoria leaf spot, entomosporium leaf spot, volutella leaf blight, phomopsis stem blight, bacterial leaf spot, fire blight, black spot, leaf curl, coryneum blight (shot hole), blossom blight, pseudomonas blight (blossom blast), shuck and kernel rot (Phytophthora cactorum), zonate leafspot (Cristulariella pyramidalis), walnut b
  • Wt % is based on the total weight of all dry ingredients.
  • Wt % is based on the total weight of all dry ingredients.
  • Wt % is based on the total weight of all dry ingredients.
  • the fungicide/bactericide compositions containing water soluble carboxylic acid derivatives, such as sodium citrate have significantly higher biocopper content (comparing formulation A to B, or comparing formulation C to D).
  • the carboxylic acid derivative and the first dispersants exhibit a synergistic effect on the biocopper content (comparing formulation B to D).
  • a carboxylic acid derivative such as sodium citrate
  • a first dispersant such as a combination of block copolymer non-ionic surfactant and a polyacrylic acid derivative
  • the fungicide/bactericide composition exhibits significantly higher biocopper content (30,000 ppm vs. 19,000 ppm) while requiring much less copper (37.28% vs. 84.55%).
  • the granules A, B, C, D, E, F, G, H, I, J, K, L, M, N and N are made as in Example 1 and are measured for biocopper:
  • the granules Al, Bl, Cl, Dl, El, Fl, Gl, Hl, Il and Jl are made as in Example 1 and are measured for biocopper:
  • the granules Kl, Ll, Ml 5 Nl, Nl, O, P, Q, R and S are made as in Example 1 and are measured for biocopper:
  • Carboxylic acid derivates 5.00% 5. 00% 4.50% 4.50% 6.00% 6.00% 6. 00% 6. 00% 4. 50% 4. 50%
  • Glycerol 1.00% 1. 00% 1.00% 1.00% 1.00% 1.00% 1. 00% 1. 00% 1. 00% 1. 00%

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Inorganic Chemistry (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

la présente invention concerne une composition améliorée de fongicide/bactéricide à base de cuivre. La composition améliorée offre une activité biologique supérieure par rapport à des produits à base de cuivre typiques, tout en nécessitant de manière significative moins de cuivre dans la composition. La présente invention concerne également des procédés de fabrication de la composition améliorée de fongicide/bactéricide à base de cuivre. La présente invention concerne aussi des procédés d'utilisation de la composition de fongicide/bactéricide améliorée à base de cuivre.
PCT/US2006/015394 2006-04-25 2006-04-25 Fongicide/BACTÉRICIDE À base de cuivre WO2007123531A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/US2006/015394 WO2007123531A1 (fr) 2006-04-25 2006-04-25 Fongicide/BACTÉRICIDE À base de cuivre
AU2006342524A AU2006342524A1 (en) 2006-04-25 2006-04-25 Copper-based fungicide/bactericide
EP06751193A EP2012590A1 (fr) 2006-04-25 2006-04-25 Fongicide/BACTÉRICIDE À base de cuivre

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2006/015394 WO2007123531A1 (fr) 2006-04-25 2006-04-25 Fongicide/BACTÉRICIDE À base de cuivre

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20081906A1 (it) * 2008-10-29 2010-04-29 Chem Project Srl Fungicidi granulari a base di composti di rame caratterizzati da alta dispersivita' in acqua
US8221796B2 (en) 2006-04-25 2012-07-17 Albaugh, Inc. Copper-based fungicide/bactericide
JP2013231001A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用殺菌剤
JP2013230999A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用水和性殺菌剤及び植物病害防除方法
JP2013230995A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用水和性殺菌剤及び植物病害防除方法
CN103609299A (zh) * 2013-11-25 2014-03-05 昆明钢铁集团有限责任公司 一种高发芽率的火棘种子繁殖方法
CN104782436A (zh) * 2015-03-30 2015-07-22 牟定县大丰农业开发有限责任公司 红心猕猴桃溃疡病防治方法
CN104909893A (zh) * 2015-06-03 2015-09-16 广西大学 一种防治食用百合炭疽病的专用复混肥
CN108077258A (zh) * 2017-12-28 2018-05-29 四川省农业科学院生物技术核技术研究所 一种防治芒果细菌性病害的颗粒剂及其制备方法
CN112400879A (zh) * 2019-08-23 2021-02-26 中国农业大学 多羧酸类化合物对真菌和卵菌附着胞的抑制活性及其在防治植物病害中的用途

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DE102009026539A1 (de) 2009-05-28 2010-12-02 Chemische Fabrik Budenheim Kg Antimikrobiell ausgerüstete Materialien
CN105850537A (zh) * 2016-04-06 2016-08-17 江苏省农业科学院 一种小麦赤霉病扩展抗性的鉴定评价方法

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EP0480614A1 (fr) * 1990-10-01 1992-04-15 Griffin Corporation Bactéricide/fongicide d'hydroxyde de cuivre, sèche et coulable, et procédé de sa préparation et utilisation
FR2668031A1 (fr) * 1990-10-19 1992-04-24 Nippon Oils & Fats Co Ltd Bouillies bordelaises et leur procede de preparation.
US20020136781A1 (en) * 2001-03-20 2002-09-26 Julio Huato Method for making colloidal cupric compounds and their uses
US6471976B1 (en) * 1990-10-01 2002-10-29 Evelyn J. Taylor Copper complex bactericide/fungicide and method of making same
WO2003028455A1 (fr) * 2001-10-04 2003-04-10 Bioacumen Pty Limited Compositions destinees au traitement et a la prevention de pathogenes de plantes

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0480614A1 (fr) * 1990-10-01 1992-04-15 Griffin Corporation Bactéricide/fongicide d'hydroxyde de cuivre, sèche et coulable, et procédé de sa préparation et utilisation
US6471976B1 (en) * 1990-10-01 2002-10-29 Evelyn J. Taylor Copper complex bactericide/fungicide and method of making same
FR2668031A1 (fr) * 1990-10-19 1992-04-24 Nippon Oils & Fats Co Ltd Bouillies bordelaises et leur procede de preparation.
US20020136781A1 (en) * 2001-03-20 2002-09-26 Julio Huato Method for making colloidal cupric compounds and their uses
WO2003028455A1 (fr) * 2001-10-04 2003-04-10 Bioacumen Pty Limited Compositions destinees au traitement et a la prevention de pathogenes de plantes

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8221796B2 (en) 2006-04-25 2012-07-17 Albaugh, Inc. Copper-based fungicide/bactericide
ITMI20081906A1 (it) * 2008-10-29 2010-04-29 Chem Project Srl Fungicidi granulari a base di composti di rame caratterizzati da alta dispersivita' in acqua
JP2013231001A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用殺菌剤
JP2013230999A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用水和性殺菌剤及び植物病害防除方法
JP2013230995A (ja) * 2012-04-27 2013-11-14 Kumiai Chemical Industry Co Ltd 農園芸用水和性殺菌剤及び植物病害防除方法
CN103609299A (zh) * 2013-11-25 2014-03-05 昆明钢铁集团有限责任公司 一种高发芽率的火棘种子繁殖方法
CN104782436A (zh) * 2015-03-30 2015-07-22 牟定县大丰农业开发有限责任公司 红心猕猴桃溃疡病防治方法
CN104909893A (zh) * 2015-06-03 2015-09-16 广西大学 一种防治食用百合炭疽病的专用复混肥
CN108077258A (zh) * 2017-12-28 2018-05-29 四川省农业科学院生物技术核技术研究所 一种防治芒果细菌性病害的颗粒剂及其制备方法
CN112400879A (zh) * 2019-08-23 2021-02-26 中国农业大学 多羧酸类化合物对真菌和卵菌附着胞的抑制活性及其在防治植物病害中的用途
WO2021036008A1 (fr) * 2019-08-23 2021-03-04 China Agricultural University Activité inhibitrice de composés d'acide polycarboxylique sur la formation d'appressorium de champignons et d'oomycètes et leur utilisation dans la lutte contre les maladies des plantes

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