JP5352337B2 - Agricultural / horticultural fungicide composition and method for controlling plant diseases - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an agricultural and horticultural bactericide composition having more excellent plant disease control effect, especially markedly improved effect of preventing and treating plant diseases and to provide a plant disease control method using the composition. <P>SOLUTION: Provided is an agricultural and horticultural bactericide composition comprising (a) an imidazole compound represented by formula (I) (wherein R is a 1C-6C alkyl group or a 1C-6C alkoxyl group; and n is an integer of 1-5) and (b) a synergistically effective amount of flutolanil. <P>COPYRIGHT: (C)2010,JPO&amp;INPIT

Description

  The present invention relates to a fungicide composition for agricultural and horticultural use having a plant disease control effect, particularly an effect of preventing and / or treating a plant disease, and a method for controlling a plant disease using the composition.

  Patent Document 1 describes that an imidazole compound represented by the following formula (I), which is an active ingredient of the agricultural and horticultural fungicide composition of the present invention, is useful as a pest control agent. There is a description that it can be used in combination with other fungicides. Patent Document 2 describes that the effect is improved when an imidazole compound different from the compound represented by the following formula (I) and flutolanil are mixed and used together. However, it is not known that when the compound represented by the formula (I) is combined with a synergistically effective amount of flutolanil, it has a remarkably excellent bactericidal effect.

European Patent Publication No. 298196 European Patent Publication No. 337103

  Each of the imidazole compounds represented by the formula (I) to be described later has a plant disease control effect that is not sufficient for a specific plant disease or has a relatively short residual effect. Then, it may show only an insufficient control effect practically against plant diseases.

  As a result of researches to solve the above-mentioned problems, the present inventors have found that when each drug is used alone by mixing and using flutolanil to the imidazole compound represented by the following formula (I). The present invention was completed by obtaining the knowledge that an even more excellent plant disease control effect could be obtained that could not be expected.

  That is, the present invention provides (a) formula (I):

(Wherein R is a C _1-6 alkyl group or C _1-6 alkoxy group, n is an integer of 1 to 5), and (b) a synergistically effective amount of flutolanil The present invention relates to an agricultural and horticultural fungicide composition characterized by containing. The present invention also relates to a method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicide composition to plants.

In the imidazole compound of the formula (I), the C _1-6 alkyl group defined as R or the alkyl portion of the C _1-6 alkoxy group includes alkyl having 1 to 6 carbon atoms such as methyl, ethyl, propyl, butyl. , Pentyl, hexyl, which may be linear or branched. When n is 2 or more, R may be the same or different.

Examples of the imidazole compound of the formula (I) include the following compounds.
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole (Compound No. 1)
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methoxyphenyl) imidazole (Compound No. 2)
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-ethylphenyl) imidazole (Compound No. 3)
4-chloro-2-cyano-1-dimethylsulfamoyl-5- (3-methyl-4-methoxyphenyl) imidazole (Compound No. 4)
The imidazole compound of the general formula (I) can be produced by the methods described in Patent Document 1, European Patent Publication No. 705823, and the like. Compound No. 1 is a compound known as the general name Cyazofamid.

  The flutolanil used as the active ingredient (b) in the present invention is a compound known as IUPAC name α, α, α-trifluoro-3′-isopropoxy-o-toluanilide.

  The fungicide composition for agricultural and horticultural use characterized by containing a synergistically effective amount of (a) at least one imidazole compound of the formula (I) and (b) flutolanil is infected with harmful diseases. Or cultivated crops such as cucumbers, tomatoes, eggplants, etc .; cereals such as rice and barley; fruit trees such as beans, apples, pears, grapes, citrus; and potatoes. For example, powdery mildew, downy mildew, anthracnose, gray mold, green mold, black star disease, spotted leaf disease, spot bacterial disease, black spot, black spot, late rot It is suitable for controlling diseases such as plague, ring rot, rice blast, blight, seedling blight, white silk disease, and Fusarium, Rhizoctonia, Verticillium, Plasmodiophora By plant pathogens such as fungi, Psium It shows an excellent control effect on soil diseases caused come. The agricultural and horticultural fungicide composition of the present invention has a long residual effect, excellent osmotic transferability, and has a preventive effect and / or a therapeutic effect, and is particularly excellent in a preventive effect.

  The agricultural and horticultural fungicide composition of the present invention specifically includes rice blast disease; rice sheath blight; rice seedling blight; cucumber anthracnose; cucumber, melon, cabbage, cabbage, onion, pumpkin, grape Downy mildew; wheat, barley, cucumber powdery mildew; potato, pepper, pepper, watermelon, pumpkin, tobacco, tomato plague; wheat septoria disease; tomato ringspot; citrus sunspot; citrus green mold; Pear scab; apple spotted leaf blight; onion white plague; brown rot of watermelon; various gray molds, mycorrhizal disease, rust, spotted bacterial diseases; Fusarium, Psium, Rhizoctonia, Verti Excellent control effect against various soil diseases caused by plant pathogens such as silicium. Moreover, the control effect which was excellent also with respect to the disease by Plasmodiohora sp. More specifically, the composition comprises: potato, pepper, pepper, watermelon, pumpkin, tobacco, tomato plague; cucumber, melon, cabbage, Chinese cabbage, onion, pumpkin, grape downy mildew; turf picium disease, red It shows a particularly excellent control effect against diseases caused by burning disease, leaf rot (brown patch, large patch) and the like.

  The active ingredient constituting the agricultural and horticultural fungicide composition according to the present invention is blended with various adjuvants as in the case of conventional agricultural chemical preparations, and emulsions, powders, wettable powders, liquids, granules, suspension preparations, etc. Can be formulated into various forms. At that time, the compound of the formula (I) and flutolanil may be mixed and formulated together, or may be separately formulated and mixed. In actual use of these preparations, they can be used as they are or after diluting to a predetermined concentration with a diluent such as water. Examples of the auxiliary agent include carriers, emulsifiers, suspending agents, thickeners, stabilizers, dispersants, spreading agents, wetting agents, penetrating agents, antifreezing agents, antifoaming agents, and the like. What is necessary is just to add suitably. Examples of the carrier include a solid carrier and a liquid carrier. Examples of the solid carrier include starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat flour, rice bran powder, wood powder, fish powder, and milk powder. Talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, sulfur powder, mineral powder such as slaked lime, etc., liquid carrier Examples include: water; vegetable oils such as soybean oil and cottonseed oil; animal oils such as beef tallow and whale oil; alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and isophorone; ethers such as dioxane and tetrahydrofuran Class: Kerosene, light Aliphatic hydrocarbons such as liquid paraffin; aromatic hydrocarbons such as toluene, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha; halogenated hydrocarbons such as chloroform and chlorobenzene; acids such as dimethylformamide Amides; Esters such as ethyl acetate and glycerin esters of fatty acids; Nitriles such as acetonitrile; Sulfur-containing compounds such as dimethyl sulfoxide or N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N- Examples include dimethylacetamide. Examples of the spreading agent include sodium alkyl sulfate, sodium alkylbenzene sulfonate, sodium lignin sulfonate, polyoxyethylene glycol alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan fatty acid ester, and the like. .

  In the method of the present invention, other agricultural chemicals such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, herbicides, plant growth preparations, etc. are mixed. In this case, a better effect may be exhibited.

In the above-mentioned other agricultural chemicals, as an active ingredient compound (generic name; including some pending applications), anilinopyrimidine such as mepanipyrim, pyrimethanil, cyprodinil Naminic compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole, ipconazole ), Azole compounds such as imibenconazole;
Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Phenylamide compounds such as furalaxyl, cyprofuram;
Sulfenic acid compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl-aluminum (fosetyl-Al), Turkish phosmethyl (tolcofos-Methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, edifenphos, Organophosphorus compounds such as iprobenfos;
N-halogenothioalkyl compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as mepronil, zoxamide, tiadinil;
Anilide compounds such as carboxin, oxycarboxin, thifluzamide, penthiopyrad, boscalid, bixafen, fluopyram, isothianil;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol, flutriafol;
Piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph, spiroxamine, and triridemorph;
Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin;
Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as silthiopham;
Amino acid amide carbamate compounds such as iprovalicarb, benthiavalicarb-isopropyl, valiphenal;
Imidazolidine compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamid;
Oxime ether compounds such as cyflufenamid;
Phenoxyamide compounds such as fenoxanil;
Atraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine;
Other compounds include pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, and sodium metam Metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), Syngenta 446510 (mandipropamid, dipromandamid, Examples include fluopicolide, carpropamid, BCF051, BCM061, BCM062, and AF-0201.

In the above-mentioned other pesticides, as an insecticide, acaricide, or nematicide, that is, an active ingredient compound of a pesticide (generic name; including some pending applications), for example, profenofos, dichlorvos ( dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos-methyl, acephate, prothiofos, fothhiazate, phosphocarb, phosphocarb, cadusafos), disulfoton, chlorpyrifos, demeton-S-methyl, dimethoate, metamidophos, imicyafos, isoxathion, isoxathion, isofenphos , Etion, etrim Etrimfos, quinalphos, dimethylvinphos, sulprofos, thiometon, bamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, propiphos-methyl (propaphos), hosalon (phosalone), formothion, malathion, tetrachlovinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, Phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, monocrotophos, parathion-methyl, terbufos (Terbufos), Phospha Dong (phospamidon), phosmet (phosmet), organic phosphoric acid ester compounds such as folate (phorate);
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocab, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicophor, tetradifon, endosulfan, dienochlor, dieldrin;
Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, fenpropatrin ( fenpropathrin), bifenthrin, imidate, cyfluthrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin ( pyrethrins), esfenvalerate, tetramethrin, resmethrin, protrifenbute, zeta-cypermethrin, acrinathrin, alpha sipe Lumetrin (alpha-cypermethrin), allethrin, gamma-cyhalothrin (gamma-cyhalothrin), theta-cypermethrin (theta-cypermethrin), tau-fluvalinate, tralomethrin, profluthrin, Pyrethroid compounds such as beta-cypermethrin, beta-cyfluthrin, metofluthrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, hexaflumuron Benzoylurea compounds such as (bistrifluron), nobifluuron, fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Imidacloprid, nitenpyram, acetamiprid, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuranoid, dinotefuranoid
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as Pyridaryl, flonicamid and the like;
Tetronic acid compounds such as spirodiclofen;
Strobilurin compounds such as fluacrypyrin;
Pyridinamine compounds such as flufenerim;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, flufenerim, pyridalyl, spirodiclofen, bifenazate (b ifenazate, spirotetramat, propargite, verbutin, spiromesifen, thiazolylcinnanonitrile, amidoflumet, flubendiamide, clofente Clofentezine metaflumizone, chlorantraniliprole, HGW-86, cyflumetofen, cyenopyrafen, pyrifluquinazone, fenazaquin, fluazaquin, pyridaben, pyrid And compounds such as chlorobenzoate, sulfluramid, metaldehyde, ryanodine; AKD-1022, IKA-2000 and the like. Furthermore, Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis or crystalline protein toxins produced by Bacillus thuringienses, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides, such as avermectin, milbemectin, milbemycin, spinosad, emamectin benzoate, ivermectin, lepimectin, spinetorum, spinetoram, It can also be used in combination with antibiotics such as abamectin and emamectin; natural products such as azadirachtin and rotenone; and repellents such as deet.

  In the agricultural and horticultural fungicide composition of the present invention, a suitable mixing weight ratio of at least one compound of formula (I) and flutolanil is generally 1: 10000 to 10,000: 1, preferably 1: 1000. 1000: 1.

  A method for controlling plant diseases in which the agricultural and horticultural fungicide composition of the present invention is applied to plants is also included in the present invention. The concentration of the active ingredient used in the agricultural and horticultural fungicide composition of the present invention varies depending on the conditions such as the target crop, method of use, formulation form, application rate, application time, type of harmful fungus, etc. In the case of foliage treatment or soil irrigation treatment, the compound represented by the general formula (I) is usually 0.01 to 1,000 ppm, preferably 0.3 to 500 ppm in terms of active ingredient concentration, and flutolanil is 0.1. -10,000 ppm, desirably 0.5-5000 ppm.

  The agricultural and horticultural fungicide composition of the present invention has a stable and high control effect on cultivated crops infected with plant diseases, and plant diseases can be controlled using this composition.

Next, some desirable embodiments of the agricultural and horticultural fungicide composition of the present invention will be exemplified, but these do not limit the present invention.
(1) An agricultural and horticultural fungicide composition comprising (a) at least one compound of formula (I) and (b) a synergistically effective amount of flutolanil.
(2) The agricultural / horticultural fungicide composition according to (1), wherein the weight ratio of (a) at least one compound of formula (I) to (b) flutolanil is 1: 10000 to 10,000: 1.
(3) The agricultural / horticultural fungicide composition according to (1), wherein the weight ratio of (a) at least one compound of formula (I) to (b) flutolanil is 1: 1000 to 1000: 1.
(4) The agricultural and horticultural fungicide composition of (1), wherein the compound of formula (I) is cyazofamid.

Next, although the test example concerning this invention is described, these do not limit this invention.
Test example 1
The strain used for the Rizoctonia solani hyphal elongation inhibition test test was pre-cultured at 20 ° C for 2 days in a PSA plate medium, and the peripheral part of the grown mycelia was punched out with a cork borer with a diameter of 4 mm, and the active ingredient compound was at a predetermined concentration It was placed on PDA plate medium prepared by diluting to contain. After the plate medium was cultured at 20 ° C. for 2 days, the mycelial elongation was measured, the inhibition rate was examined, and the results are shown in Table 1. The average mycelial elongation of the untreated group was 23.5 mm. Moreover, the theoretical value of the inhibition rate was calculated according to Colby's formula and listed in parentheses in Table 1. When the experimental value is higher than the theoretical value according to the Colby equation, the agricultural and horticultural fungicide composition of the present invention has a synergistic effect on the control of plant diseases.

Test example 2
Rhisoctonia (Rizoctonia solani) hyphal elongation inhibition effect test In the same manner as in Test Example 1, mycelial elongation was measured, the inhibition rate was examined, and the results are shown in Table 2. The average mycelial elongation of the untreated group was 66 mm.

Test example 3
Pythium graminicola hyphal elongation inhibitory effect test In the same manner as in Test Example 1, hyphal elongation was measured, the inhibition rate was examined, and the results are shown in Table 3. The average mycelial elongation of the untreated group was 46 mm.

  Next, although the formulation example of the composition for pest control of this invention is described, this invention is not limited to these.

Formulation Example 1 (I) Siazofamide 2 parts by weight, (B) Flutolanil 10 parts by weight, (C) Sodium naphthalenesulfonate formalin condensate 5 parts by weight, (D) Sodium alkylbenzenesulfonate 5 parts by weight, (E) Clay 78 parts by weight Part of the above ingredients are mixed to obtain a wettable powder.

Formulation Example 2 (b) Siazofamide 0.5 parts by weight, (b) Flutolanil 2.5 parts by weight, (c) Calcium carbonate 20 parts by weight, (d) Clay 77 parts by weight can get.

Claims (3)

An agricultural and horticultural fungicide composition comprising a synergistically effective amount of (a) cyazofamid and (b) flutolanil. The agricultural and horticultural fungicide composition according to claim 1, wherein the mixing weight ratio of (a) cyazofamide and (b) flutolanil is 1: 100000 to 10000: 1. A plant disease control method comprising applying the agricultural and horticultural fungicide composition according to claim 1 or 2 to a plant.