JP2003513989A - Non-aqueous concentrated spreading oil composition - Google Patents

Abstract

SUMMARY OF THE INVENTION The present invention relates to non-aqueous, stable, single-phase, thick spreading oil (SO) formulations. This SO formulation contains as active ingredients a compound of formula (I) below, one or more vegetable oils, and a polar aprotic organic solvent. Optionally, the SO formulation may contain one or more methylated vegetable oils. This SO formulation is useful as a rice fungicide in an aqueous environment.

Description

Detailed Description of the Invention

BACKGROUND OF THE INVENTION The present invention relates to a storage-stable, non-aqueous, concentrated spreading oil (SO) formulation for crop protection active compounds, and its use for controlling pests, especially in an aqueous environment. Pesticide application to

To date, pesticides have usually been in the form of soluble, dispersible or absorbable granules that release the active ingredient into water, or an emulsifiable concentrate that disperses the active ingredient on the surface of a spraying liquid, especially water. It has been applied to paddy fields as a formulation (eg EP 0 206 987).

European patent application EP 0 415 569 proposes the application of a fungicidal composition to an aqueous environment, the fungicidal composition comprising a solid carrier, the fungicide azoxyst as the active ingredient. It contains a robin (eg EP 0 382 375) and an oil with which the active ingredient is miscible or dispersible.

The efficacy of plant protection agents is that when the active ingredient is applied in dissolved form rather than in particulate form,
It is well known that it will be higher. One of the environmentally friendly methods of applying the active ingredient in dissolved form is to dissolve it in vegetable oil. Unfortunately, however, most plant protection agents do not show high solubility in vegetable oils.

In view of the easy and safe handling of plant protection agents and the need to improve efficacy,
Suitable for application in paddy fields, containing relatively high concentration of plant protection agent in spreading oil
It is desirable to develop SO formulations.

SUMMARY OF THE INVENTION The present invention provides the following components (a) to (d): (a) 15 to 400 g / L of one or more crop protective active compounds, (b) 300 to 700 g / L of 1 One or more vegetable oils, (c) 30 to 200 g / L of one or more polar aprotic organic solvents, and, optionally, (d) one or more methylated vegetable oils ( However, the total of all components in the formulation is 1 liter), a single-phase, non-aqueous concentrated spreadable oil formulation for crop protection active compounds.

[0007]   Another aspect of the invention is a method of making such SO formulations.

Further, the present invention is a method for controlling diseases and / or pests in an aqueous environment, wherein water is treated with the SO formulation of the present invention, so that an oily film spreads on the surface of water, , The oily film is pre-grown in this aqueous environment,
Alternatively, it relates to the above method comprising contacting a subsequently planted plant with the active ingredient contained in the SO formulation.

Another aspect of the invention is a method of enhancing the efficacy of fungicidal triazolopyrimidine compounds (eg EP 0 550 113) against rice diseases in paddy fields, especially compounds of formula I below. Yes,

[Chemical 3] This method essentially comprises the following components (i) to (iii): (i) one or more vegetable oils, (ii) one or more polar aprotic organic solvents, and, optionally, (iii) applying to the aqueous environment of rice an effective amount of one or more compounds of formula I dissolved in a mixture consisting of one or more methylated vegetable oils.

The above and other objects and features of the present invention will become more apparent from the detailed description given below.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Now, surprisingly, the following components (a) to (d): (a) 15 to 400 g / L of one or more crop protective active compounds, (b) ) 300-700 g / L of one or more vegetable oils, (c) 30-200 g / L of one or more polar aprotic organic solvents, and, if necessary, (d) one or more methylated A stable, single-phase, non-aqueous spreading oil for application of the crop protection active compound in an aqueous environment, comprising a vegetable oil (but not more than 1 liter of all ingredients in the formulation) (S
O) It was found that a formulation could be obtained.

By using the SO formulations of the present invention, the biological activity of the active ingredient against pests can be increased compared to conventional types of formulations.

As used herein, the term “single phase” means that the crop active compound (a) is (a), (b), (c) and optionally without any phase separation. Accordingly, it means that it is completely dissolved in the homogeneous mixed state of (d).

The term “pest” as used herein includes, but is not limited to, plant pathogens, insects and weeds.

In principle, all crop protection active compounds can be used in the non-aqueous concentrated spreadable oil formulations according to the invention, but lipophilic crop protection active compounds are preferred.

In general, crop protection active compounds are used which are essentially insoluble in water and have a very low solubility in pure vegetable oil (b). 100 g / based on solvent (b)
Solubility below L, especially below 50 g / L is preferred.

The composition of the invention can be applied to plants in an aqueous environment together with various active substances. These active substances can be used as fertilizers, reagents for trace elements, other products that affect the growth of plants, or beneficial microorganisms used to improve plant nutrition (
For example, any of Azetobacter, Rhizobia, Azolla, etc.) may be used.
However, preferably the active substance is selective herbicide, insecticide, fungicide, fungicide, nematicide, algaecide, molluscicide, rodenticide, virucidal agent, resistant to plants. Inducible compounds and biocontrol agents such as viruses, bacteria, nematodes, fungi and other microorganisms, bird and animal repellents, and plant growth regulators, or mixtures of several of these substances.

The chemical crop protection compound is preferably one which is solid at room temperature, especially having a melting point of 50 ° C.
Those above are preferable.

Mixtures of different bioactive compounds can exhibit a broader spectrum of activity than a single compound. Moreover, they may show a synergistic effect compared to the single active ingredient. In a preferred embodiment, the formulations according to the invention can be used in mixtures of active ingredients. In the case of the mixture, all of the active ingredient (a) is dissolved in the solvent mixture of the spreadable oil (SO) formulation of the present invention.

Preferred fungicides for use in the compositions of the present invention are commercially available compounds selected from the following group: That is, AC 382042, anilazine, azoxystrobin, benalaxyl, benomyl, binapacrylic, bitertanol, blasticidin S, bromconazole, bupilimate, captafol, captan, carbendazim, carboxin, carpropazamide, chlorbenzthiazone, chlorothalonil. , Clozolinate, Cycloheximide, Cimoxanil, Cipofuram, Cyproconazole, Cyprodinil, Diclofluanid, Dicron, Dichlorane, Diclobutrazol, Diclocimet, Diclomedine, Dietofencarb, Difenoconazole, Diflumetrim, Dimethymol, Dimethomorph, Diniconazole.
Dinocap, ditalimphos, dithianon, dodemorph, dodine, edifenphos, epoxyconazole, etaconazole, etirimol, etridiazole, famoxadone, phenapanyl, phenamidone, phenalimol, fenbuconazole, fenfram, fenhexamide, fenpiclonyl, fenpropidin, fenpropimorph, Fentin, fentin acetate, ferimzone, fluazinam, fludioxonil, flumethobar, fluquinconazole, flucylazole, fursulfamide, flutolanil, flutriafor, folpet, fuveridazole, furaraxil, furametopir, guazatine, hexaconazole, IKF-916
, Imazalil, iminoctadine, ipconazole, iprodione, isoprothiolane, iprovaricarb, kasugamycin, KH-7281, kitadine P, kresoxime
-Methyl, Mepanipyrim, Mepronil, Metalaxyl, Methoconazole, Metofloxam, MON65500, Microbutanil, Neoasodine, Nickel Dimethyldithiocarbamate, Nuarimol, Offlace, Organic Mercury Compound, Oxadixyl,
Oxycarboxin, penconazole, pencyclone, phenazine oxide, phthalide, polyoxine D, polyram, probenazole, prochloraz, procymidione, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyrokilone, pyroxyflu, quinomethionate, quinoxyphene, quintoxene, quintoxene, quintoxene Spiroxamine, SSF-126, SSF-129, streptomycin, tebuconazole, teclophthalam, technazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, tiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclazole. , Tridemorph, trifloxystrobin, triflumizole, Rihorin, triticonazole, validamycin A,
Examples include vinclozolin, XRD-563, and zalilamide.

Further, the formulations of the present invention may include at least one of the following types of biological control agents: For example, viruses, bacteria, nematodes, fungi, and other microorganisms suitable for controlling insect, weed or plant diseases, or for inducing host resistance in plants. Examples of such biological control agents include:
Bacillus thuringiensis, Verticillium lecanii, Autographica californica NPV (Autogr
aphica californica NPV), white bacillus (Beauvaria bassiana), Amperomyces quisqualis, Bacillus subtilis, Pseudomonas fluorescens, Streptomyces
Examples include Streptomyces griseoviridis and Trichoderma harzianum.

Furthermore, the formulation of the present invention comprises at least 1 that induces systemic acquired resistance in plants.
Two chemical reagents, such as isonicotinic acid or its derivatives, 2,2-dichloro-3,3-
Dimethylcyclopropylcarboxylic acid, or BION may be included.

The SO formulation of the invention may be obtained, for example, from European patent application EP 0 550 113 or international patent application.
Derivatives of the azlopyrimidines disclosed in WO98 / 46608, especially formula I:

[Chemical 4] (In the formula, R ¹ and R ² each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclic group, Alternatively, R ¹ and R ² together with an adjacent nitrogen atom represent an optionally substituted heterocycle, R ³ represents a halogen atom or an alkyl or alkoxy group, and n represents 0 to 5 Represents an integer, and Hal represents a halogen atom).

More preferred compounds are those of formula I in which R ¹ and R ² together with the intervening nitrogen atom represent a 4-methylpiperidine ring; or R ¹ is a C _1-6 alkyl group (especially , Isopropyl group), C _1-6 haloalkyl group (particularly 2,2,2-trifluoroethyl group or 1,1,1-trifluoroprop-2-yl group), or C _3-8 cycloalkyl group ( A cyclopentyl group or a cyclohexyl group), R ² represents a hydrogen atom, and / or n is 2 or 3, R ³ is bonded to the 2-position, 4-position, 6-position, and Represents a fluorine or chlorine atom or a C _1-6 alkoxy group.

A particularly preferred compound is the following azolopyrimidine: 5-chloro-6- (2-chloro-6-fluorophenyl) -7- (4-methylpiperid-1-yl)-[1,2,4 ] Triazolo [1,5
-a] Pyrimidine (generic name Azlopyrimidine A), 5-chloro-6- (2-chloro-6-fluorophenyl) -7- (2,2,2-trifluoroethylamino)-[1,2,4 ] Triazolo [1,5-a
] Pyrimidine (generic name Azlopyrimidine B), and 5-chloro-6- (2,4,6-trifluorophenyl) -7- (1,1,1-trifluoroprop-2-ylamino)-[1, 2,4] Triazolo [1,5-a] pyrimidine (generic name Azolopyrimidine C).

Due to the chiral nature of its 1,1,1-trifluoroprop-2-yl group, azolopyrimidine C is in the form of racemic mixtures or enantiomerically enriched compounds, especially the (S) -enantiomer (generic name (S It can be applied as) -azolopyrimidine C).

The most preferred compounds are at least one compound of formula I and at least one fungicidal active ingredient which acts as an inhibitor of melanin biosynthesis (eg AC 382).
042).

Preferred herbicides include commercially available compounds selected from the following group: That is, 2,4-D, 2,4-DB, 2,4-DP, acetochlor, acifluorfen, alachlor, aloxidim, ametridione, amidesulfuron, ashram, atrazine, azimsulfuron, benfresat, bensulfuron, bentazone. , Bifenox, bromobutide, bromoxynil, butachlor, cafenstrol, carfentrazone, chloridazone, chlorimurone, chlorpropham, chlorsulfuron, chlortoluron, cinmethyline, cinosulfuron, clomazone, clopyralid, cyanadine, cycloate, cyclosulfamuron, cycloxidim, dymuron , Desmedifam, dimethasone, dicamba, diclovenil,
Diclofop, diflufenican, dimethenamide, dithiopyr, diuron, eptam, esprocarb, ethizine, phenoxaprop, flamprop-M-
Isopropyl, Flamprop-M-Methylfluazifop, Fluometuron, Fluoroglycophene, Fluridone, Fluroxypyr, Fultamon, Fluthiamid, Fomesafen, Glufosinate, Glyphosate, Halosafen, Haloxifop, Hexazinone, Imazametabenz, Imazamethapir, Imazamox, Imazapyr, Imazapyr, Imazapyr, Imazapyr, Imazapyr, Imazapyr, Imazapil Isoproturon, isoxaben, isoxaflutol, lactofen, MCPA, MCPP, mefenacet, metabenzthiazulone, metamitron, metazachlor, methyl daimuron, metolachlor, metribuzin, metsulfuron, molinate, nicosulfuron, norflurazone, oryzalin, oxadiaargyl, oxas. Luflon, oxyfluorfen, pendimethali , Picloram, pretilachlor, prop crawl,
Propanyl, prosulfocarb, pyrazosulfuron, pyridate, quinmelac, quinclorac, quizalhopetil, setoxydim, cimetrin, sulcotrione, sulfentrazone, sulfosate, terbutrin, terbutyrazine, thiamethuron, thifensulfuron, thiobencarb, tralkoxydim, trialate, trias. Examples include luflon, tribenuron, triclopyr, trifluralin and the like.

Further preferred are the derivatives of aryloxypicolinamides disclosed for example in European patent application EP-A-0 447 004, in particular having the generic name picolinaphene.
N- (4-fluorophenyl) 6- (3-trifluoromethylphenoxy) pyrid-2-ylcarboxamide.

Examples of insecticide compounds include alpha cypermethrin, benfuracarb, BPMC
, Buprofezin, carbosulfan, cartap, chlorfenvinphos, chlorpyrifos-methyl, cycloprotoline, cypermethrin, esfenvalerate, etofenprox, fenpropatrine, flucitrinate, flufenoxuron, hydramethylnon, imidacloprid , Isoxathion, MEP
, MPP, nitenpyram, PAP, permethrin, propaphos, pymetrozine, silafluofen, tebufenozide, teflubenzuron, temephos, terbufos, tetrachlorbinphos and triazamate.

In general, the non-aqueous SO formulations according to the invention comprise 15 to 400 g / L, preferably 20 to 200 g / L, particularly preferably 25 to 100 g / L of one or more crop protective active compounds.

The vegetable oil (b) above is preferably selected from the group consisting of olive oil, soybean oil, orange oil and sunflower oil, and the vegetable oil (b) is especially the following fatty acids: palmitic acid, palmoleic acid. ), Stearic acid, oleic acid, linoleic acid, linolenic acid are preferred triglycerides or mixtures of triglycerides.

Suitable vegetable oils are those having a density at 25 ° C. of less than 1 g / mL, preferably 0.90 g / mL to 0.95 g / mL.

Most preferred is a vegetable oil having the following properties ^*:

In general, the non-aqueous SO of the invention comprises 300 to 700 g / L, preferably 350 to 600 g / L, particularly preferably 400 to 500 g / L of one or more vegetable oils (b).

The polar aprotic solvent (c) used as a co-solvent is necessary to increase the amount of active ingredient. Without these co-solvents, smaller amounts of the active ingredient could be dissolved in SO, and the resulting formulation would be phytotoxic because of the increased amount of solvent applied to the plant. is there. The preferred polar solvent is 2.
It is a compound that has a dielectric constant of 5 or more, particularly 2.7 to 4.0 at 25 ° C, and low solubility in water. Preferred solvents include ketones such as cyclohexanone, lactones such as γ-butyrolactone, and amides such as cyclic _amides.For example, NC _1-18 alkylpyrrolidone, preferably NC _2-16 alkylpyrrolidone or NC _{5-. 8} cycloalkylpyrrolidone. The most preferred solvents are N-octylpyrrolidone and N-dodecylpyrrolidone. In another preferred embodiment of the present invention, the auxiliary solvent is essentially the following _{formula: H 3 CO-CO- (CH} 2) m -CO-OCH 3 ( where, m is 2, 3 or 4) Or more, preferably 2 or 3
It consists of the seed dimethyl dicarboxylate.

A particularly preferred solvent is a mixed solvent consisting of glutaric acid dimethyl ester, succinic acid dimethyl ester and adipic acid dimethyl ester, and the most preferred solvent is DBE. DBE is Lemro Chemieprodukte Michael Mrozyk KG (Grevenbroich
, Germany).

Generally, the non-aqueous SO of the present invention comprises 30 to 200 g / L, preferably 50 to 150 g / L, especially 75 to
It contains 125 g / L of one or more polar aprotic solvents (c).

Methylated vegetable oils (used as the non-polar, water-immiscible co-solvent (d) of the present invention) are generally esters of medium chain fatty acids with methanol, preferably in the presence of lipase. Or corresponding esterification of vegetable oils
) Is a methyl ester. The preferred fatty acids of these vegetable oils have 5 to 20, especially 6 to 15 carbon atoms. In general, the vegetable oils according to the invention are mixtures of fatty acids of different chain lengths, with the major constituents in the mixture (ie 50% or more of the mixture) having 10 carbon atoms being particularly preferred. In a preferred embodiment, the methylated vegetable oil used is caprylic acid / capric acid or the methyl ester of capric acid with less than 5% fatty acids with chain lengths other than 10. Particularly preferred methylated vegetable oils are Witconol® 1095 and Witconol® 2309 (available from Witco Corporation, Houston, Texas, USA), or Edenor® ME C 6-10 and Edenor ( (Registered trademark) ME C 12 7
0 (available from Henkel KGaA, Dusseldorf, Germany). Generally, the non-aqueous SO of the present invention comprises at least 100 g / L, preferably 150-450 g / L, especially 250-400 g / L of one or more methylated vegetable oils (d).

The relative amounts of active ingredient (a) and vegetable oil (b) in the present invention are 1:50 to 1: 1, preferably 1:30 to 1: 5, particularly preferably 1:20 to 1: 1. 10 is appropriate.

Recommended doses are known for various uses of the phytoprotective active compound (a) whose efficacy may be increased according to the invention. By using in the SO formulation of the invention, the amount of active ingredient required per hectare (depending on the active ingredient, solvent and cosolvent and their amounts) can be reduced by half or more, It becomes possible to control more diseases with a moderate dose.

An important advantage of the present invention is the rapid onset of activity and high persistence due to the use of this new SO formulation. As a result, the pesticide application period is extended, and the pesticide can be used with greater flexibility.

[0043]   The pesticide SO formulation of the present invention can be used for protection and healing.

In a particularly preferred embodiment of the invention, the non-aqueous SO consists essentially of the following (a)-(
d) consists of: (a) 15-400 g / L, preferably 20-200 g / L of one or more crop protection active compounds (especially compounds of formula I); (b) 300-700 g / L, Preferably 350 to 600 g / L of one or more vegetable oils selected from the group consisting of olive oil and sunflower oil; (c) 30 to 200 g / L, preferably 50 to 150 g / L of one or more polar aprotic. Solvent (particularly N-octylpyrrolidone or N-dodecylpyrrolidone); (d) If necessary, 450 g / L or less, preferably 200 to 400 g / L of one or more methylated vegetable oils (especially caprylic acid). And / or methyl ester of capric acid)
.

Treatment of the solvents (b), (c) and (d) and the pesticidally active compound (a) by well established procedures gives the SO formulations of the invention. For example, a solution is formed by dissolving (a) in a suitable mixture of (b), (c) and (d), optionally in the presence of a volatile solvent to facilitate dissolution. sell.

The SO formulation of the present invention usually comprises 1.5-40% w / v active ingredient, 30-70% w / v vegetable oil, 3
~ 20% w / v polar aprotic solvent, 0-45% w / v methylated vegetable oil, and 0-10% w / v other additives (e.g. defoamers, corrosion inhibitors) , Stabilizers, penetrants and adhesives), and anionic and / or nonionic dispersants to obtain stable liquid products.

The completed non-aqueous SO formulation of the present invention is stable even for storage over a relatively long period of time. The SO of the present invention provides a formulation of a crop protection active compound, which has the advantage of being optimized and easy to use since it contains a large amount of one or more agrochemical active ingredients contained in the formulation.

The solubility of the active ingredient (a) in the formulation according to the invention depends not only on the structure of the active ingredient but also on the amount of cosolvent (c). When 10 to 15% of the co-solvent (c) is added to the formulation,
The relative amount of active ingredient (a) is increased by about 40-60%.

The SO formulation of the present invention is preferably sprayed or sprinkled onto the surface of the paddy field, which is an aqueous environment, particularly using the so-called shaker bottle application method.

This formulation spreads well as a monolayer on the surface of the water and adheres to the surface of the leaf of rice, which is lipophilic.

Also included within the scope of the invention are solid granules in which the SO formulations of the invention are adsorbed on a solid carrier, for example as disclosed in EP 0 415 569.

SO formulations described herein which contain a fungicide as the active ingredient (a) preferably have a fungicidal effect against one or more of the following diseases: Leaf blight (Xanthomonas)
campestris pv. oryzae), blast (Pyricularia oryzae), and brown spot (Cochliobol)
us miyabeanus), stupa seedling disease and stock rot (Gibberella fujikuroi), and blight (Rhizo)
ctonia solani), as well as seedling blight (Corticium rolfsii). The term “fungicidal effect” as used herein means that the active ingredient is active against fungal disease.

For a clearer understanding of the invention, specific examples are described below. These examples are merely illustrative and should not be understood in any way as limiting the scope and underlying principles of the invention. Various modifications of the invention in addition to those shown and described herein will be apparent to those skilled in the art from the following examples and the description above. Such modifications are also intended to fall within the scope of the claims herein.

Examples Examples of non-aqueous SO formulations of the present invention are shown in Examples 1-4 below. Substance names of materials used in the examples

Example 1 The following SO formulations of the invention are prepared by dissolving the active ingredient in a mixture of solvents (b), (c) and (d). The following formulation is obtained: The SO formulation exhibits the following properties: Density = 0.912 g / mL, flash temperature> 83 ° C., no crystals formed when stored at 0 ° C. for 1 week.

Example 2 The following SO formulations of the present invention are prepared by dissolving the active ingredient in a mixture of solvents (b), (c) and (d). The following formulation is obtained:

Example 3 The following SO formulations of the present invention are prepared by dissolving the active ingredient in a mixture of solvents (b), (c) and (d). The following formulation is obtained:

Example 4 The following SO formulations of the invention are prepared by dissolving the active ingredient in a mixture of solvents (b), (c) and (d). The following formulation is obtained:

Control of rice blast fungus “Koshihikari” variety of Gramineae plants was grown in a nursery box and transplanted into a 457 cm ² section in a greenhouse (4 plants / plant pot). Three days after implantation, various (S) -azolopyrimidine C formulations were added to water. 45 days after the treatment with the active ingredient of the present invention, the plants were inoculated with a spore solution of rice blast fungus. Untreated compartments were included in the study.

A At 52 days after the treatment of rice leaf blast , 63% of the leaf area of untreated rice (control) was infected with rice blast. Furthermore, the disease level (% infected leaf area) was evaluated in the treated plants,
The efficacy of treatment (%) was measured. Table 1 shows the effects of the SO preparation and the granule preparation of the present invention.

[0061]

[Table 1]

B At the 126th day after the rice blast treatment, 60% of the area of the untreated rice (control) ears was infected with the rice blast. Furthermore, the disease level (% infected ear area) was evaluated in the treated plants to determine the efficacy (%) of the treatment. Table 2 shows the effects of the SO preparation and the granule preparation of the present invention.

[0063]

[Table 2]

According to the above test, it is possible to reduce the dose by about 50% in order to obtain the same level of disease control effect when using the SO preparation of the present invention as compared with the conventional granular preparation. There was found.

[0065]   Furthermore, phytotoxicity was negligible at the application rates tested.

Moreover, the SO formulations of the present invention are more environmentally friendly than conventional formulations and have an improved toxicity profile, which makes the formulations safer to handle.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) A01N 43/824 A01N 43/82 101B (81) Designated country EP (AT, BE, CH, CY, DE, DK) , ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR), OA (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML) , MR, NE, SN, TD, TG), AP (GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW), EA (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN CR, CU, CZ, DE, DK, DM, DZ, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP , KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, PL, PT, R O, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG, UZ, VN, YU, ZA, ZW F terms (reference) 4H011 AA01 AB01 AC01 BA01 BA02 BA06 BB09 BB10 BC06 BC09 DA12 DD02 DG15

Claims (12)

[Claims] 1. The following components (a) to (d): (a) 15 to 400 g / L of one or more crop protection active compounds, (b) 300 to 700 g / L of one or more vegetable oils, (c) 30 to 200 g / L of one or more polar aprotic organic solvent, and, if necessary, (d) one or more methylated vegetable oil, A total of 1 liter of all ingredients), a single-phase, non-aqueous concentrated spreadable oil formulation for crop protection active compounds. 2. The spreadable oil formulation according to claim 1, which contains 100 to 450 g / L of one or more methylated vegetable oils (d). 3. A crop protection active compound (a) comprising one or more compounds of formula I: (In the formula, R ¹ and R ² each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclic group. , Or
R ¹ and R ² together with the adjacent nitrogen atom represent an optionally substituted heterocycle, R ³ represents a halogen atom or an alkyl or alkoxy group, n represents an integer of 0 to 5. Wherein Hal represents a halogen atom) and the triazolopyrimidine is represented by the formula. 4. The spreadable oil formulation according to claim 1, wherein the vegetable oil (b) is selected from the group consisting of olive oil, soybean oil, orange oil and sunflower oil. 5. The vegetable oil (b) is a triglyceride or mixture of triglycerides consisting essentially of the following fatty acids: palmitic acid, palmoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid. The spreadable oil preparation according to claim 1. 6. The ratio of the crop protection active compound (a) to the vegetable oil (b) is 1:50 to 1: 1.
The spreadable oil formulation according to claim 1, which is preferably from 1:30 to 1: 5. 7. The polar aprotic organic solvent (c) is selected from the group consisting of NC _1-14 alkylpyrrolidone, NC _5-8 cycloalkylpyrrolidone, γ-butyrolactone, and cyclohexanone. Spreadable oil formulation. 8. The spreadable oil preparation according to claim 7, wherein the polar aprotic organic solvent (c) is N-octylpyrrolidone or N-dodecylpyrrolidone. 9. The spreadable oil formulation according to claim 2, wherein the methylated vegetable oil (d) is a C ₁₀ methylated fatty acid. 10. The spreadable oil formulation according to claim 2, wherein the methylated vegetable oil (d) is a methyl ester obtained from palm kernel oil. 11. A method for controlling diseases and / or pests in an aqueous environment, wherein water is treated with the spreading oil formulation of claim 1 so that an oily film spreads on the surface of the water, The above method, wherein the oily film subsequently comprises contacting the plant with the active ingredient contained in the spreadable oil formulation. 12. The following formula I: embedded image (Wherein R ¹ , R ² , R ³ , Hal, and n have the meanings defined in claim 2), which is a method for enhancing the efficacy of rice compounds against rice diseases in paddy fields. In essence, the following components (i) to (iii): (i) one or more vegetable oils, (ii) one or more polar aprotic organic solvents, and optionally (iii) A method as described above comprising applying to the aqueous environment of rice an effective amount of one or more compounds of formula I dissolved in a mixture consisting of one or more methylated vegetable oils.