Patent Application
20240268388
The present invention relates to an agricultural/horticultural fungicidal composition. The present invention relates more specifically to an agricultural/horticultural fungicidal composition with excellent fungicidal activity and superior safety. The present application claims the priority of Japanese Patent Application No. 2021-080430, filed on May 11, 2021, the content of which is herein incorporated by reference.
For the cultivation of agricultural or horticultural crops, various compounds have been proposed that have disease control activity against crop diseases. To practically implement such compounds as agricultural/horticultural fungicides, the following is required including not only sufficiently high efficacy, but also hardly occurring drug resistance, occurrence of neither chemical damage to plants nor soil contamination, and low toxicity to livestock, fish, and other organisms.
WO 2019/022061 A describes an oxadiazol compound and an oxadiazol compound-containing fungicide for agricultural and horticultural use.
The present invention addresses the problem of providing an agricultural/horticultural fungicidal composition with better fungicidal activity and without any concern about chemical damage to useful plants.
As a result of intensive research to solve the above problem, the present invention, which encompasses the following items, has been completed.
Specifically, the present invention is as follows.
and a salt thereof, wherein
An agricultural/horticultural fungicidal composition of the present invention has excellent disease control effects, causes no chemical damage to plant bodies, exerts less toxicity to humans, livestock, or fish, and less affects environment.
An agricultural/horticultural fungicidal composition of the present invention is a composition comprising component (I) and component (II).
The agricultural/horticultural fungicidal composition of the present invention, of course, may be applied as a mixture of the component (I) and component (II). An aspect, in which component (I) and component (II) are not mixed, but each component is applied separately, is included.
The component (I) in the present invention is at least one compound selected from the group consisting of a compound of formula (I) and a salt thereof. This compound may be used as an agricultural/horticultural fungicide.
Here, each term used herein will be described.
The term “C1-6 alkyl group” means a linear or branched C1-6 saturated hydrocarbon group.
Specifically a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, or an n-hexyl group or the like may be exemplified.
The term “C2-6 chained unsaturated hydrocarbon group” means a linear or branched C2-6 hydrocarbon group containing at least one double or triple bond. Examples include, in addition to a “C2-6 alkenyl group” or a “C2-6 alkynyl group”, those having two or more double or triple bonds, such as a butadienyl group, a butadiynyl group, a pentadienyl group, or a pentadiynyl group.
The term “C2-6 alkenyl group” means a linear or branched C2-6 hydrocarbon group containing one double bond.
Specifically, a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, or a 2-methyl-2-propenyl group or the like may be exemplified.
The term “C2-6 alkynyl group” means a linear or branched C2-6 hydrocarbon group containing one triple bond.
Specifically, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, or a 1-methyl-2-propynyl group or the like may be exemplified.
The term “C3-6 cycloalkyl group” means a C3-6 saturated monocyclic hydrocarbon group (also called monocyclic carbon ring group) with carbon atoms arranged in a ring.
Specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group or the like may be exemplified.
The term “C6-10 aryl group” means a C6-10 monocyclic or bicyclic hydrocarbon group having carbon atoms arranged in a ring and at least one aromatic ring. The term is also called an aromatic group.
Specifically, a phenyl group or a naphthyl group or the like may be exemplified.
The term “5- to 6-membered heterocyclyl group” means a cyclic group consisting of 5 to 6 ring atoms and a saturated or partially unsaturated 5- to 6-membered heterocyclyl group in which 1 to 4 of the ring atoms have heteroatoms each independently selected from nitrogen, oxygen, or sulfur, or a cyclic group consisting of 5 to 6 ring atoms and a 5- to 6-membered heteroaryl group in which 1 to 4 of the ring atoms have heteroatoms each independently selected from nitrogen, oxygen, or sulfur.
Specifically, as the 5-membered saturated heterocyclyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, or a thiazolidinyl group or the like may be exemplified.
As the 6-membered saturated heterocyclyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a tetrahydropyranyl group, a dioxolanyl group, or a dioxanyl group or the like may be exemplified.
As the 5-membered heteroaryl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group or the like may be exemplified.
As the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group or the like may be exemplified.
As the 5-membered partially unsaturated heterocyclic group, a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, or an isoxazolinyl group or the like may be exemplified.
As the 6-membered partially unsaturated heterocyclic group, a dihydropyranyl group or the like may be exemplified.
The term “halogeno group” means a fluoro group, a chloro group, a bromo group, or an iodo group.
The term “C1-6 alkoxy group” means a group formed by bonding a C1-6 alkyl group and a hydroxyl group.
Specifically, a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group or the like may be exemplified.
The term “C1-6 alkylthio group” means a group formed by bonding a C1-6 alkyl group and a thiol group.
Specifically, a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group or the like may be exemplified.
The term “C1-6 alkylsulfinyl group” means a group formed by bonding a C1-6 alkyl group and a sulfinyl group.
Specifically, a methyl sulfinyl group, an ethyl sulfinyl group, or a t-butyl sulfinyl group or the like may be exemplified.
The term “C1-6 alkylsulfonyl group” means a group formed by bonding a C1-6 alkyl group and a sulfonyl group.
Specifically, a methyl sulfonyl group, an ethyl sulfonyl group, or a t-butyl sulfonyl group or the like may be exemplified.
The term “C1-6 haloalkyl group” means a halogeno-substituted C1-6 alkyl group.
Specifically, a chloromethyl group, a chloroethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 1-fluoro-n-butyl group, or a perfluoro-n-pentyl group or the like may be exemplified.
The term “C1-6 haloalkoxy group” means a halogeno-substituted C1-6 alkoxy group.
Specifically, a trifluoromethoxy group, a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, or a 2,2,2-trifluoroethoxy group or the like may be exemplified.
The term “C1-2 alkylene group” means a divalent C1-2 alkyl group.
Specifically, a methylene group, a dimethylene group or the like may be exemplified.
The term “C1-6 alkylene group” means a divalent C1-6 alkyl group.
Specifically, in addition to the above methylene or dimethylene group, a trimethylene group or a tetramethylene group or the like may be exemplified.
A salt of a compound of formula (I) is not particularly limited as long as the salt is agriculturally or horticulturally acceptable. For example, a salt of an inorganic acid (e.g., hydrochloric acid, sulfuric acid); a salt of an organic acid (e.g., acetic acid, lactic acid); a salt of an alkali metal (e.g., lithium, sodium, potassium); a salt of an alkali earth metal (e.g., calcium, magnesium); a salt of a transition metal (e.g., iron, copper); a salt of an organic base (e.g., triethylamine, tributylamine, pyridine, hydrazine); or ammonium.
Specific examples of the compound of formula (I) or the salt thereof include those listed in WO2019/022061, and they may be produced by known methods, such as the method described in the above publication.
The compounds listed in Table 1 below are particularly preferable examples.
The component (II) used in combination with the component (I) in the present invention is, for instance, a compound (fungicide) that has fungicidal activity and is other than formula (I). The component (II) may also be any of a compound with insecticidal activity (insecticide), a compound with acaricidal activity (acaricide), a compound with herbicidal activity (herbicide), a compound with plant growth regulating activity (plant growth regulator), a fertilizer, or a compound with chemical damage reducing activity (chemical damage reducer) The component (II) may be at least one compound, and two or more compounds may be selected and used in combination.
The fungicide that may be used as the component (II) and the amount thereof are not particularly limited as long as its fungicidal effects can be exerted.
As the fungicide that may be used as the component (II), each compound listed on the FRAC (Fungicide Resistance Action Committee) website (https://www.frac.info/), or an agriculturally acceptable salt or derivative thereof may be exemplified.
Specific examples may include each compound selected from the following groups.
The component (II) may be an insecticide or acaricide. As preferable the insecticide or acaricide that may be used as the component (II),
Specific examples may include each compound selected from the following groups.
(11) Microbially derived insect enteric membrane disruptors:
The component (II) may be a herbicide. As the herbicide that may be used as the component (II),
Specific examples may include each compound selected from the following groups.
The component (II) may also be a plant growth regulator.
Specifically, as the plant growth regulator that may be used as the component (II), each compound selected from the following group may be exemplified.
The component (II) may be a fertilizer.
Specifically, as the fertilizer that may be used as the component (II), each compound selected from the following group may be exemplified.
The component (II) may be a chemical damage reducer (safener).
Specifically, as the chemical damage reducer that may be used as the component (II), each compound selected from the following group may be exemplified.
In the agricultural/horticultural fungicidal composition of the present invention, the ratio between component (I) and component (II) may be optionally selected. The weight ratio between component (I) and component (II) is usually from 1:1,000,000 to 1,000,000:1, preferably from 1:100,000 to 100,000:1, more preferably from 1:10,000 to 10,000:1, still more preferably from 1:1,000 to 1,000:1, and still more preferably from 300:1 to 1:300, and particularly preferably from 1:100 to 100:1.
The agricultural/horticultural fungicidal composition of the present invention may be used for the control of plant diseases caused by a wide range of filamentous fungi, such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, or Zygomycetes.
Examples of the plant disease (pathogen), which is subject to control, are listed below.
The agricultural/horticultural fungicidal composition of the present invention may be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, seedlings, and/or cuttings. In addition, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMOs) of these plants are also applicable.
The agricultural/horticultural fungicidal composition of the present invention may be used for seed treatment, foliar spray, soil application, and water application to control various diseases occurring on agricultural/horticultural crops including flowers, turf, or pasture grasses.
The agricultural/horticultural fungicidal composition of the present invention may be used as a seed treatment agent, and any form of seed treatment known to those skilled in the art may be used, including soaking seeds in the composition, submerging them, or coating them with the composition. The seed treatment should be conducted prior to seeding.
Applying to seeds this composition in the form of a coating is a preferred form, and seeds coated with a layer containing an agricultural/horticultural fungicidal composition of the present invention may also be used.
Regarding the coating, seeds may be coated using a variety of processes known in the art. For example, the coating process may include spraying a seed treatment composition onto the surfaces of seeds while agitating the seeds in suitable equipment such as a tumbler or pan-type granulator.
The agricultural/horticultural fungicidal composition of the present invention may contain an additional component(s) other than the component (I) and component (II). As the additional component(s), known ingredients used for formulation may be exemplified.
As the dosage form of the agricultural/horticultural fungicidal composition of the present invention, a common agrochemical form, that is, as the dosage form, dustable powder (DP), wattable powder (WP), emulsifiable concentrate (EC), flowable (FL), suspension concentrate (SC), water soluble powder (SP), water dispersible granules (WG), tablets, granules (GR), suspo emulsion (SE), oil dispersion (OD), or emulsion-oil-in-water (EW) may be exemplified. Formulation is not limited by any particular technique or procedure, but may be performed by any known technique or procedure.
In an aspect of the present invention, auxiliary preparation materials used in the formulation such as various carriers, solvents, or additives are not particularly limited. One aspect of the present invention is a fungicidal composition containing an agrochemically acceptable solid and/or liquid carrier.
In the case of using a solid dosage form, the solid carrier may be used, including plant powder (e.g., soybean flour, wheat flour), mineral fine powder (e.g., diatomaceous earth, phospholite, gypsum, talc, bentonite, pyrophyllite, clay), or an organic/inorganic compound (e.g., sodium benzoate, urea, mirabilite).
In the case of using a liquid dosage form, the liquid carrier may be used, including petroleum distillate (e.g., kerosene, xylene, solvent naphtha), cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, or water.
For the formulation, a surfactant may be optionally added. As the surfactant, a nonionic surfactant (e.g., a polyoxyethylene adduct of alkyl phenyl ether, a polyoxyethylene adduct of alkyl ether, a polyoxyethylene adduct of higher fatty acid ester, a polyoxyethylene adduct of sorbitan higher fatty acid ester, a polyoxyethylene adduct of tristyrylphenyl ether), polyoxyethylene-added alkyl phenyl ether sulfate, or a formaldehyde condensate of alkylbenzenesulfonate, higher alcohol sulfate, alkyl naphthalene sulfonate, polycarboxylate, lignin sulfonate, or alkylnaphthalene sulfonate, or an isobutylene-maleic anhydride copolymer may be exemplified.
The concentration of active ingredients in the fungicidal composition of the present invention may be set, if appropriate, according to the dosage form. For example, the concentration of active ingredients in a wattable powder is preferably from 5 to 90 wt % and more preferably from 10 to 85 wt %. The concentration of active ingredients in an emulsion is preferably from 3 to 70 wt % and more preferably from 5 to 60 wt %. The concentration of active ingredients in granules is preferably from 0.01 to 50 wt % and more preferably from 0.05 to 40 wt %.
The method of preparing a preparation is not particularly limited, and any known preparation method may be employed depending on the dosage form.
The following shows some Preparation Examples. Note that the preparation formulation shown below is merely examples and may be modified without departing from the main purpose of the present invention. The present invention is not limited in any way by the following Preparation Examples. Unless otherwise specified, the “parts” means “parts by weight.”
40 parts of compounds of components (I) and (II), 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are homogenously mixed and finely pulverized to give wattable powder with 40% active ingredients.
30 parts of compounds of components (I) and (II), 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to give an emulsifiable concentrate with 30% active ingredients.
5 parts of compounds of components (I) and (II), 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are homogenously mixed, finely pulverized, and then granulated to a particle diameter of 0.5 to 1.0 mm to give granules with 5% active ingredients.
5 parts of compounds of components (I) and (II), 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sodium sulfosuccinate, and 1 part of potassium phosphate were homogenously mixed and pulverized. Water is added and the mixture is kneaded well, then granulated and dried to give granules with 5% active ingredients.
10 parts of compounds of components (I) and (II), 4 parts of polyoxyethylene alkylallyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size is 3 microns or less to give a suspension concentrate with 10% active ingredients.
40 parts of compounds of components (I) and (II), 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkyl benzene sulfonate, 8 parts of sodium lignin sulfonate, and 5 parts of formaldehyde condensate of sodium alkyl benzene sulfonate are homogenously mixed and finely pulverized. Next, an appropriate amount of water is added, and the mixture is kneaded to form a clay. The clay-like material is granulated and then dried to give water dispersible granules with 40% active ingredients.
The fungicidal effects exerted by each agricultural/horticultural fungicidal composition of the present invention are demonstrated in the following Test Examples.
The compounds with compound Nos. 1 to 12 in component (I) of the tables are the same as the compounds with compound Nos. 1 to 12 in Table 1 above.
Compounds of component (I) and component (II) were dissolved in dimethyl sulfoxide at 10,000 ppm and diluted with water to the prescribed concentration to prepare a chemical agent solution. A mixture of the prescribed concentration of the chemical agent solution, wheat leaf blight pathogen (Septoria tritici) conidia, and malt extract was prepared on a microplate and incubated at 20° C. in the dark for 3 days. The turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth of wheat leaf blight pathogen was compared with that of no treatment control to determine the growth inhibition rate. The results are shown in Tables 2 to 7, along with the expected values calculated as below.
Each expected value was calculated from the fungicidal efficacy of a single application of the compound of component (I) and the fungicidal efficacy of a single application of compound of component (II) by using Colby's equation (S. R. Colby, Calculating synergistic and antagonistic responses of herbicide combinations, Weeds, 15, 20-22 pp (1967)).
In Tables 2 to 7, some favorable synergistic effects were observed for all combinations of components (I) and (II).
Compounds of component (I) and component (II) were dissolved in dimethyl sulfoxide and diluted with water to the prescribed concentration to prepare a chemical agent solution. A mixture of the prescribed concentration of the chemical agent solution and sterile water was prepared on a microplate, and leaf discs cut from soybean leaves were floated on the microplate. Uredospores of soybean rust pathogen (Phakopsora pachyrhizi) were inoculated and incubated at 25° C. for 9 days. The area percentage of lesions was determined by observing uredospore-forming lesions on the leaf discs, and the control value was calculated. The control value was calculated by the following formula:
Control value (%)=100−{Area percentage of lesions in treatment plot/Area percentage of lesions in untreatment plot}×100.
The results are shown in Tables 8 to 18, along with the expected values calculated as below. Each expected values was calculated from the fungicidal efficacy of a single application of compound of component (I) and the fungicidal efficacy of a single application of compound of component (II) by using Colby's equation:
In Tables 8 to 18, some favorable synergistic effect was observed for all combinations of component (I) and component (II).
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The compounds were dissolved in dimethyl sulfoxide to prepare a chemical agent solution.
A mixture of the prescribed concentration of the chemical agent solution, cucumber anthracnose pathogen (Colletotrichum lagenarium) conidia, and Vogel medium was prepared on a microplate and incubated at 20° C. in the dark for 7 days.
The turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth of cucumber anthracnose pathogen was compared with that of no treatment control to determine the growth inhibition rate. The results are shown in Tables 19 to 24, along with the expected values calculated as below.
Each expected value was calculated using Colby's equation:
In Tables 19 to 24, some favorable synergistic effect was observed for all combinations of components (I) and (II)
The component (I) and component (II) may be used in combination to produce an agricultural/horticultural fungicidal composition with excellent plant disease control effects, which cannot be obtained using each single component alone.
When the component (I) is one of the above-mentioned compounds 1 to 12, for example, metarylpicoxamid other than the above-mentioned compounds may be used as the compound of component (II) to produce substantially the same effects.
Any of those selected randomly from the compositions of the present invention can exert the above effects. From the above, it should be understood that any of the compositions of the present invention, including relevant compositions not shown in the Examples, is effective in controlling plant diseases while chemical damage is low and fungicidal effects are high, and is useful as an agricultural/horticultural fungicidal composition.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2021-080430 | May 2021 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2022/019639 | 5/9/2022 | WO |
