(19)
(11)EP 2 965 628 B1

(12)EUROPEAN PATENT SPECIFICATION

(45)Mention of the grant of the patent:
26.06.2019 Bulletin 2019/26

(21)Application number: 14760550.5

(22)Date of filing:  24.02.2014
(51)International Patent Classification (IPC): 
A01N 47/18(2006.01)
A01N 43/713(2006.01)
A01P 3/00(2006.01)
(86)International application number:
PCT/JP2014/054355
(87)International publication number:
WO 2014/136603 (12.09.2014 Gazette  2014/37)

(54)

METHOD FOR CONTROLLING RHIZOPUS GENUS FUNGUS IN RICE

VERFAHREN ZUR BEKÄMPFUNG VON FUNGUS DES GENUS RHIZOPUS IN REIS

PROCÉDÉ POUR LUTTER CONTRE CHAMPIGNONS DE GENRE RHIZOPUS DANS RIZ


(84)Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

(30)Priority: 05.03.2013 JP 2013042625

(43)Date of publication of application:
13.01.2016 Bulletin 2016/02

(73)Proprietor: Nippon Soda Co., Ltd.
Tokyo 100-8165 (JP)

(72)Inventors:
  • SAIGA Tomoyuki
    Makinohara-shi Shizuoka 421-0412 (JP)
  • KATO Kazushige
    Makinohara-shi Shizuoka 421-0412 (JP)
  • WATANABE Shinya
    Makinohara-shi Shizuoka 421-0412 (JP)
  • FUKUYO Akie
    Makinohara-shi Shizuoka 421-0412 (JP)

(74)Representative: Mewburn Ellis LLP 
City Tower 40 Basinghall Street
London EC2V 5DE
London EC2V 5DE (GB)


(56)References cited: : 
EP-A1- 1 426 371
WO-A1-2012/045798
JP-A- 2010 248 273
JP-A- 2011 520 778
US-A1- 2011 201 613
WO-A1-03/016303
WO-A1-2012/128135
JP-A- 2011 515 368
US-A1- 2011 105 566
US-A1- 2013 005 672
  
      
    Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).


    Description

    TECHNICAL FIELD



    [0001] The present invention relates to a method for controlling phytopathogenic filamentous fungi other than oomycete microorganisms. More specifically, the present invention relates to a method for controlling Rhizopus genus Fungus in rice with superior efficacy using a low concentration of an active ingredient.

    [0002] Priority is claimed on Japanese Patent Application No. 2013-042625, filed March 5, 2013.

    BACKGROUND ART



    [0003] Patent Document 1 discloses that a tetrazoyloxime derivative and agricultural chemicals containing the tetrazoyloxime derivative as an active ingredient exhibit a particularly powerful effect in the prevention and treatment of plant diseases caused by fungi of the genus Pythium including Pythium ultimum, the genus Aphanomyces, or oomycetes belonging to closely related genera.

    [0004] Further, Patent Document 2 discloses that a tetrazoyloxime derivative and agricultural chemicals containing the tetrazoyloxime derivative as an active ingredient exhibit effectiveness against plant diseases caused by various filamentous fungi including oomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. The publication specifically mentions powerful effects upon the oomycetes Plasmopara viticola and Phytophthora infestans.

    [0005] Patent Document 3 discloses a fungicidal aqueous suspension composition for agriculture and horticulture. The composition comprises an oxime compound together with other specified components. The test examples show use of a composition to control Phytophthora infestans on tomato plants and Pythium graminicola on rice plants.

    [0006] Patent Document 4 discloses fungicides which contain oxime compounds or salts thereof. In a test example, a fungicide is used to control Phytophthora infestans sprayed on to tomato plants. In a further example, the fungicide is used to control growth of Pythium aphanidermatum on agar plates.

    [0007] Patent Document 5 discloses a plant disease control agent containing a tetrazolyl oxime derivatives and salts thereof. In a worked example, a plant disease control agent is used to control the growth of Pythium graminicola on agar plates.

    [0008] Patent Document 6 discloses a pesticide composition intended for protecting plants, crops or seeds against fungal diseases or insect damages. The composition comprises a tetrazolyloxime derivative and a thiazolylpiperidine derivative. In the test examples, compositions are used to control a Phytophthora infestans infection of tomato plants and a Venturia inaequalis infection of apple plants.

    PRIOR ART LITERATURE


    Patent Documents



    [0009] 

    Patent Document 1: JP 2009-269913 A

    Patent Document 2: WO 03/016303

    Patent Document 3: EP 2687088

    Patent Document 4: JP 2010-248273

    Patent Document 5: US 2013/005672

    Patent Document 6: WO 2012/045798


    DISCLOSURE OF INVENTION


    Problems to be Solved by the Invention



    [0010] Incidentally, symptoms similar to the damage caused to rice plants by damping-off fungi can also be caused by phytopathogenic filamentous fungi belonging to the genus Rhizopus. However, minimal investigation has been conducted relating to effective methods for controlling these types of phytopathogenic filamentous fungi other than oomycete microorganisms.

    [0011] A problem of the present invention is to provide a method for controlling phytopathogenic filamentous fungi other than oomycete microorganisms with superior efficacy using a low concentration of an active ingredient.

    Means for Solving the Problems



    [0012]  As a result of investigations aimed at solving the above problem, the inventors of the present invention discovered that a tetrazoyloxime derivative of formula (II) in a formulation with an auxiliary material exhibited a superior control effect against Rhizopus genus Fungus in rice. The present invention was completed on the basis of this finding.

    [0013] In other words, the present invention includes the aspects described below. [1]. A method for controlling Rhizopus genus Fungus in rice using a formulation consisting of
    1. (i) at least one compound selected from the group consisting of the compound represented by formula (II) and salts thereof, and
    2. (ii) an auxiliary material
      wherein the amount of the compound represented by formula (II) or the salts thereof incorporated within the formulation is within a range from 2 to 70% by mass:


    Effects of the Invention



    [0014] The control method according to the present invention can, with a low concentration of the active ingredient in a formulation, effectively control fungi of the genus Rhizopus in rice, which can cause symptoms known as damping-off.

    DESCRIPTION OF THE EMBODIMENTS



    [0015] Preferred examples of the present invention are described below, but the present invention is in no way limited by these examples. The control method according to the present invention uses a formulation incorporating a compound of formula (II) or a salt thereof and an auxiliary material.

    [0016] The salt used in the present invention is a salt of the compound represented by formula (II). There are no particular limitations on this salt, provided it is permissible for use in agriculture and horticulture. Specific examples of the salt include salts of inorganic acids such as a hydrochloride, a nitrate, a sulfate or a phosphate, and salts of organic acids such as an acetate, a lactate, a propionate or a benzoate.

    [0017] The compound represented by formula (II) (hereafter referred to as "compound II") is below.



    [0018] (II) The nitrogen-containing heterocyclic compounds represented by formula (II) and the salts thereof can be produced using known methods such as the methods disclosed in Patent Document 1 and Patent Document 2.

    [0019] (II) In the control method according to the present invention, the nitrogen-containing heterocyclic compound represented by formula (II) or the salt thereof is used within a formulation. There are no particular limitations on the form of this formulation, and any of the forms that can be adopted in typical agricultural and horticultural chemicals can be adopted, including dustable powders, wettable powders, water soluble powders, emulsifiable concentrates, flowable agents, pellets and granules and the like. The formulation also includes an auxiliary material.

    [0020] There are no particular limitations on the types of auxiliary materials that can be used in preparing the above formulations. Examples of these auxiliary materials include solid carriers, solvents, surfactants, and other additives.

    [0021] Specific examples of the solid carriers include plant-based powders such as soy flour or wheat flour, and mineral-based fine powders such as silica dioxide, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay and joint soil.

    [0022] Specific examples of the solvents include kerosene, xylene, petroleum distillates such as solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oils, plant oils and water.

    [0023] Specific examples of the surfactants include nonionic surfactants such as polyoxyethylene adducts of alkyl phenyl ethers, polyoxyethylene adducts of alkyl ethers, polyoxyethylene adducts of higher fatty acid esters, polyoxyethylene adducts of sorbitan higher fatty acid esters and polyoxyethylene adducts of tristyryl phenyl ether, as well as sulfate ester salts of polyoxyethylene adducts of alkyl phenyl ethers, alkylbenzene sulfonates, sulfate ester salts of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensation products of alkylnaphthalene sulfonates, and isobutylene-maleic anhydride copolymers.

    [0024] Specific examples of the additives include organic and inorganic compounds such as sodium benzoate, urea and salt cake, oils such as rapeseed oil, soybean oil, sunflower oil, castor oil, pine oil and cottonseed oil, and derivatives and concentrates of these oils.

    [0025] The amount of the nitrogen-containing heterocyclic compound represented by formula (I) or the salt thereof incorporated within the formulation is from 2 to 70% by mass. For example, in the case of a water-dispersible powder, the amount is preferably from 5 to 90% by weight, and more preferably from 10 to 85% by weight, in the case of an emulsion, the amount is preferably from 3 to 70% by weight, and more preferably from 5 to 60% by weight.

    [0026] Further, conventional germicides, insecticides, miticides, and may be mixed with the formulation incorporating compound (II) or the salt thereof. In the control method according to the present invention, the compound represented by formula (II) or the salt thereof can be used within a variety of application methods, including foliage application, soil application, water surface application and seed treatment. The amount applied varies depending on the plant being treated and the plant disease being targeted, but in the case of foliage application, a solution having an active ingredient concentration within a range from 1 to 10,000 ppm, and preferably 10 to 1,000 ppm is preferably applied at a rate of 50 to 300 L per 10 are, in the case of soil application or water surface application, the application of 0.1 to 1,000 g, and particularly 10 to 100 g, of the active ingredient per 10 are is preferable, and in the case of a seed treatment, the application of 0.001 to 50 g of the active ingredient per 1 kg of seeds is preferable. The control method according to the present invention is used against fungi of the genus Rhizopus.

    [0027] There are no particular limitations on the fungi belonging to the genus Rhizopus, and examples include phytopathogens that cause rice seedling damping-off (Rhizopus oryzae, Rhizopus chinensis, Rhizopus javanicus, Rhizopus arrhizus), satsumaimo fuhaibyo (Rhizopus nodosus, Rhizopus oryzae), togarashi hetagusare-byo (Rhizopus stolonifer), melon black mold (Rhizopus stolonifer), strawberry soft rot (Rhizopus nigricans) and lily bulb rot (Rhizopus oryzae).

    [0028] The control method according to the present invention can be performed by targeting any of the various regions of rice. Examples of the various regions of plants that may be targeted include the leaves, stems, stalks, flowers, buds, fruit, seeds, sprouts, roots, tubers, tuberous roots, shoots and cuttings. Further, the control method according to the present invention can also be applied to improved or altered varieties, cultivars, mutants, hybrids and genetically modified organisms (GMO) of these plant types.

    EXAMPLES



    [0029] The control method according to the present invention is described below in further detail using a series of examples. However, the present invention is in no way limited by these examples.

    Formulation Example 1



    [0030] Ten parts by mass of the compound II, 2 parts by mass of polyoxyethylene aryl phenyl ether, 0,5 parts by mass of sodium dialkylsulfosuccinate, 5 parts by mass of glycerol, 0.3 parts by mass of xanthan gum, and 82.2 parts by mass of water were mixed together. The resulting mixture was subjected to wet grinding until the particle size was not more than 3 µm, thus obtaining a flowable agent containing 10% of the active ingredient.

    <<Control of Rice Seedling Damping-off (Fusarium genus Fungus)>> Reference Example 1



    [0031] A fungus culture of Fusarium roseum cultivated in a soil bran medium was mixed with a test soil to prepare a contaminated soil.

    [0032] Small seedling boxes (8.5 cm × 8,5 cm × 3 cm) filled with this contaminated soil as the bed soil were irrigated by diluting the flowable agent obtained in Formulation Example 1 with water, and applying about 40 ml of the diluted agent uniformly to each seedling box. The active ingredient treatment amount was 2 mg/box.

    [0033] Rice seeds (of the koshihikari variety) in the so-called hatomune state (in which a bud with a length of about 1 mm was protruding from each rice seed), prepared by subjecting the rice seeds to presoaking and forced germination treatments, were sowed across the entire surface of each seedling box, and an additional amount of the contaminated soil was then used to cover the seeds. The seedling boxes were then placed in a nursery cabinet at 30°C for 3 days to allow the seeds to germinate. Subsequently, a low-temperature treatment at 4°C was performed for 3 days. Following this low-temperature treatment, the seedlings were raised inside a glass greenhouse. Twenty eight days after sowing, the number of healthy seedlings (A), the number of withered seedlings (B), the number of stunted seedlings (having a height less than 1/2 of that of the healthy seedlings) (C), the number of above ground diseased seedlings (D) and the number of root diseased seedlings (E) within each seedling box were counted, and when the disease severity was calculated using the following formula, the result was 15.1.




    Comparative Example 1



    [0034] A hydroxyisoxazole-metalaxyl liquid reagent was diluted with water to obtain a chemical solution containing 0.03% of hydroxyisoxazole and 0.004% of metalaxyl.

    [0035] With the exception of using this chemical solution instead of the aforementioned water-diluted flowable agent, the disease severity was calculated using the same method as that described for Example 1. Although the active ingredient treatment amount was 13.6 mg/box, the disease severity was 22.3.

    Comparative Example 2



    [0036] With the exception of not performing the application of the water-diluted flowable agent, the disease severity was calculated using the same method as that described for Example 1. The disease severity was 30.3.

    <<Control of Rice Seedling Damping-off (Rhizopus genus Fungus)>>


    Example 2



    [0037] A fungus culture of Rhizopus chinensis cultivated in a soil bran medium was mixed with a test soil to prepare a contaminated soil.

    [0038] Small seedling boxes (8.5 cm × 8.5 cm × 3 cm) filled with this contaminated soil as the bed soil were irrigated by diluting the flowable agent obtained in Formulation Example 1 with water, and applying about 40 ml of the diluted agent uniformly to each seedling box. The active ingredient treatment amount was 2 mg/box.

    [0039] Rice seeds (of the koshihikari variety) in the so-called hatomune state (in which a bud with a length of about 1 mm was protruding from each rice seed), prepared by subjecting the rice seeds to presoaking and forced germination treatments, were sowed across the entire surface of each seedling box, and an additional amount of the contaminated soil was then used to cover the seeds. The seedling boxes were then placed in a nursery cabinet at 34°C for 3 days to allow the seeds to germinate. Subsequently, a low-temperature treatment at 4°C was performed for 3 days. Following this low-temperature treatment, the seedlings were raised inside a glass greenhouse. Twenty two days after sowing, the number of healthy seedlings (A), the number of withered seedlings (B), the number of severely diseased seedlings (having a height less than 1/2 of that of the healthy seedlings) (C), and the number of lightly diseased seedlings (having a height of at least 1/2 but less than 3/4 of that of the healthy seedlings) (D) within each seedling box were counted, and when the disease severity was calculated using the following formula, the result was 9.7.




    Comparative Example 3



    [0040] A chlorothalonil water-dispersible powder was diluted with water to obtain a chemical liquid having an active ingredient concentration of 0.08%.

    [0041] With the exception of using this chemical liquid instead of the aforementioned water-diluted flowable agent, the disease severity was calculated using the same method as that described for Example 2. Although the active ingredient treatment amount was 16 mg/box, the disease severity was 11.4.

    Comparative Example 4



    [0042] With the exception of not performing the application of the water-diluted flowable agent, the disease severity was calculated using the same method as that described for Example 2. The disease severity was 20.2.

    [0043] The above results indicate that the control method of the present invention exhibits a superior control effect against fungi of the genus Rhizopus compared with conventional chemical reagents.

    INDUSTRIAL APPLICABILITY



    [0044] The present invention can provide a method for controlling Rhizopus genus Fungus in rice using a formulation having a compound of Formula (II) or a salt thereof and an auxiliary material.


    Claims

    1. A method for controlling Rhizopus genus Fungus in rice using a formulation consisting of

    (i) at least one compound selected from the group consisting of the compound represented by formula (II) and salts thereof, and

    (ii) an auxiliary material
    wherein the amount of the compound represented by formula (II) or the salts thereof incorporated within the formulation is within a range from 2 to 70% by mass:


     


    Ansprüche

    1. Verfahren zur Bekämpfung des Rhizopus-Pilzes in Reis unter Verwendung einer aus Folgendem bestehenden Formulierung:

    (i) zumindest einer Verbindung, die aus der Gruppe ausgewählt ist, die aus der in Formel (II) dargestellten Verbindung und Salzen davon besteht, und

    (ii) einem Hilfsstoff,
    wobei die Menge der durch Formel (II) dargestellten Verbindung oder der Salze davon, die in der Formulierung aufgenommen ist/sind, im Bereich von 2 bis 70 Massen-% liegt:


     


    Revendications

    1. Procédé pour lutter contre un champignon du genre Rhizopus dans le riz, utilisant une formulation consistant en

    (i) au moins un composé choisi dans le groupe constitué par le composé représenté par la formule (II) et ses sels, et

    (ii) un matériau auxiliaire,
    dans lequel la quantité du composé représenté par la formule (II) ou de ses sels, incorporée dans la formulation, est située dans la plage allant de 2 à 70 % en masse :


     






    Cited references

    REFERENCES CITED IN THE DESCRIPTION



    This list of references cited by the applicant is for the reader's convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

    Patent documents cited in the description