JP3339956B2 - Pesticide efficacy enhancer and pesticide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel agricultural chemical potency enhancer, an agricultural chemical potency enhancer composition, and an agricultural chemical composition containing the same.

[0002]

BACKGROUND OF THE INVENTION Insecticides, fungicides, herbicides,
Pesticides such as acaricides and plant growth regulators are used in dosage forms such as emulsions, wettable powders, granules, powders, and flowables. At this time, in order to sufficiently bring out the effects of the pesticidal drug substance, various measures are taken in terms of the physical properties of the formulation, but it is difficult to further enhance the effect of the pesticide by means of the formulation. Also, since the development of new pesticides is more difficult, it is of great industrial significance to further enhance the activity of existing pesticides.

Hitherto, surfactants comprising various nitrogen-containing compounds such as quaternary ammonium salts, betaines and amine oxides have been known as having an effect of enhancing the activity of pesticides (Japanese Patent Application Laid-Open (JP-A) No. 2002-157572). 1963-145205
issue). Among them, quaternized or further polyoxyethylenated long-chain amines are known to be particularly effective. However, the effect of the above compounds having the effect of enhancing the activity of pesticides has not yet been satisfactory.

[0004]

Means for Solving the Problems The present inventors have conducted further intensive studies in order to find an effect enhancer for agrochemicals that enhances the efficacy of agrochemicals by combining with a pesticide drug substance. It has been found that a fluorinated fatty acid alkanolamide or a specific fatty acid amide polyoxyalkyleneacetic acid or a salt thereof has an effect of enhancing potency particularly for various pesticides, and thus completed the present invention.

That is, the present invention provides an agrochemical efficacy enhancer containing a compound represented by the general formula (I) as an active ingredient.

[0006]

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Wherein R ^{1 is} a straight-chain or branched alkyl or alkenyl group having 5 to 29 carbon atoms R ² and R ^{3 are the} same or different and are hydrogen or methyl, or a mixture of hydrogen and methyl n: average Number of 1 to 30 m: Number of 1 to 30 on average

[0008]

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R ⁶ represents a linear or branched alkyl or alkenyl group having 1 to 29 carbon atoms. The present invention also provides an agrochemical efficacy enhancer comprising a compound represented by the general formula (II) as an active ingredient.

[0010]

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Wherein R ⁷ : a linear or branched alkyl or alkenyl group having 5 to 29 carbon atoms R ⁸ : hydrogen or methyl group or a mixture of hydrogen and methyl groups p: an integer of 1 to 30 on average X : Represents hydrogen, Na, K, NH ₄ or an organic ammonium cation. ].

The compound of the general formula (I) according to the present invention can be obtained, for example, as follows. First, a fatty acid monoethanolamide is obtained from a fatty acid and monoethanolamine, and then an alkylene oxide is added by a conventional method, whereby an alkylene oxide adduct of the fatty acid monoethanolamide is obtained. Further, a fatty acid is added to the obtained alkylene oxide adduct of fatty acid monoalkanolamide and esterified to obtain a target fatty acid monoethanolamide esterified compound.

[0013] By using diethanolamine instead of monoethanolamine in the same manner as described above, the fatty acid diethanolamide type end-esterified fatty acid diethanolamide can be obtained via fatty acid diethanolamide and its alkylene oxide adduct. Can be The compound of the general formula (I) can also be obtained by using isopropanolamine instead of the above ethanolamines.

The compound of the fatty acid amide polyoxyalkyleneacetic acid type represented by the general formula (II) is obtained, for example, by obtaining a fatty acid monoethanolamide from a fatty acid and monoethanolamine, and further adding an alkylene oxide to the compound. It is obtained by reacting with monochloroacetic acid sodium salt in the presence of an alkali, adding hydrochloric acid and desalting. Further, in the case of a salt form, it can be neutralized with an alkali such as sodium hydroxide.

Of course, the method for producing the compounds of the general formulas (I) and (II) according to the present invention is not limited to these.

The compound of the general formula (I) according to the present invention is preferably such that n is an average number of 1 to 20, m is an average number of 1 to 20, and more preferably n is an average number. 1-10
And m is a number of 1 to 10 on average. In particular, in the present invention, m and n are in this range, and m + n is an average of 2 ≦ 2.
It is preferred to use compounds with a number in the range m + n <25. R ¹ is preferably a linear or branched alkyl group or alkenyl group having 7 to 21 carbon atoms, and coconut oil-based fatty acid, palm oil-based fatty acid, tallow-based fatty acid, lauric acid, myristic acid, palmitic acid, stearin Those using an acid or oleic acid are more preferably used. Further, as the alkylene oxide, ethylene oxide in which R ² and R ³ are hydrogen is preferable, and a mixed adduct of ethylene oxide and propylene oxide in which R ² and R ³ are a mixture of hydrogen and a methyl group is also preferably used. Also, R ⁶
Is preferably a linear or branched alkyl group or alkenyl group having 1 to 21 carbon atoms.

In the compound of the general formula (II) according to the present invention, p is a positive number on average of 1 to 20, more preferably n
Are preferably compounds having a positive number of 1 to 10 on average. Further, R ⁷ is preferably the same as R ¹ in the general formula (I). General formula (II)
In the formula, X is hydrogen, Na, K, NH ₄ or an organic ammonium cation, and examples of the organic ammonium cation include primary, secondary, and tertiary amines such as monoethanolamine, diethanolamine, triethanolamine, isopropylamine, and diisopropylamine. Secondary amine salts.

The pesticidal efficacy enhancer of the present invention comprising the compound of the above general formula (I) or (II) has no phytotoxicity when used in combination with the pesticidal drug substance, and increases the potency of the pesticidal drug substance by 2-3 times. I can do it.

Fatty acid alkanolamides are known substances and are used as foam stabilizers for shampoos and the like. In the field of pesticides, Japanese Patent Application Laid-Open No. 58-128301 discloses an aqueous suspension pesticide comprising a water-insoluble to insoluble pesticide active ingredient, a polyhydric alcohol-type nonionic surfactant, a thickener, and the like. However, this is intended to stabilize the aqueous suspension pesticide. JP-A-4-41406 discloses an example in which a pyrethroid insecticide is used, and JP-A-2-142708 discloses an example in which a fatty acid alkanolamide is used as a stabilizer for a pyrethroid compound and / or an organic phosphorus compound. Furthermore, Japanese Patent Publication No. 63-41884 describes that alkanolamides are effective for killing ectoparasites and / or killing eggs, but only for "shirasu". That is, it has never been known that an esterified fatty acid alkanolamide or a fatty acid amide polyoxyalkyleneacetic acid or a salt thereof has the effect of enhancing the efficacy of a pesticide,
It was first discovered by the present invention.

The present invention relates to a method for determining whether an agrochemical potency enhancer containing a compound represented by the general formula (I) or (II) according to the present invention as an active ingredient has a remarkable potency-enhancing action irrespective of the type of the pesticide structure. Although the mechanism is not always clear, one of the possible reasons is that the potentiator of the present invention has a very strong solubilizing power for pesticides, and it is thought that the pesticides are finely divided to promote penetration into the plant body, insects, and fungi. Can be

The compound represented by the general formula (I) or (II) can be obtained by using at least one compound represented by the general formula (I) or (II) according to the present invention together with a surfactant other than these. The amount of the compound represented by the general formula (I) or (II) can be reduced while maintaining the effect of the compound to enhance the efficacy of the pesticide. As the surfactant, a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, or a mixture thereof can be used.

Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl aryl ether formaldehyde condensate, polyoxyalkylene aryl ether, polyoxyalkylene alkyl ester, and polyoxyalkylene alkyl. Sorbitol ester, polyoxyalkylene sorbitan ester, polyoxyalkylene alkyl glycerol ester, polyoxyalkylene block copolymer, polyoxyalkylene block copolymer alkyl glycerol ester, polyoxyalkylene alkyl sulfonamide, polyoxyalkylene rosin ester, polyoxy Propylene block copolymer, polyoxyethylene oleyl ether, polio Sialic sharp emission alkylphenols, and the like a mixture of two or more of these.

Examples of the cationic surfactant include an alkylamine ethylene oxide adduct, an alkylamine propylene oxide adduct such as tallowamine ethylene oxide adduct, oleylamine ethylene oxide adduct, soyamine ethylene oxide adduct, cocoamine There are ethylene oxide adducts, synthetic alkylamine ethylene oxide adducts, octylamine ethylene oxide adducts, and the like, and mixtures thereof.

Typical anionic surfactants are available in aqueous or solid form, such as sodium mono- and di-alkylnaphthalene sulfonates, sodium alpha-olefin sulfonates, Sodium alkane sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyalkylene alkyl ether sulfate, polyoxyalkylene alkyl aryl ether sulfate, polyoxyalkylene styryl phenyl ether sulfate, mono- and di-alkylbenzene sulfonate, Alkyl naphthalene sulfonate,
Formaldehyde condensate of alkyl naphthalene sulfonate, alkyl diphenyl ether sulfonate, olefinic sulfonate, mono and dialkyl phosphate, polyoxyalkylene mono and dialkyl phosphate, polyoxyalkylene mono and diphenyl ether phosphate, polyoxyalkylene Mono and dialkyl phenyl ether phosphates, polycarboxylates, fatty acid salts, linear and branched alkyl polyoxyalkylene ether acetic acids or salts thereof, alkenyl polyoxyalkylene ether acetic acids or salts thereof, stearic acid and salts thereof, oleic acid and Its salt, N-methyl fatty acid tauride (tauride)
s), mixtures of two or more of these, including sodium, potassium, ammonium and amine salts.

Examples of suitable amphoteric surfactants include lauryl dimethylamine oxide and alumox.
(Armox) C / 12, amine oxide, monaterics (Mon
aterics), Milanols, betaine, Lonzaines, other amine oxides, mixtures thereof and the like.

Among these surfactants, non-ionic surfactants or anionic surfactants, in particular, polyoxyalkylene alkylglycerol esters are preferred in combination with the compound of the general formula (I). A nonionic surfactant or a cationic surfactant is preferably used in combination with the compound of the above (2).

An agrochemical efficacy enhancer containing the compound represented by the general formula (I) or (II) and a surfactant other than the above as an active ingredient is represented by the general formula (I) or (II). The preferable combined ratio of the compound to be used and the surfactant is [the total amount of the compound represented by the general formula (I) or (II)] / [the surfactant other than the compound] = 1/10 to 50 / 1 (weight ratio), more preferably 1/1 to 10/1.

The pesticidal composition of the present invention comprises the above-described pesticide efficacy enhancer or the pesticide efficacy enhancer composition, and a pesticidal drug substance. Here, the pesticide drug substance refers to an active ingredient of the pesticide. In the pesticidal composition of the present invention, the pesticide efficacy enhancer is a compound represented by the general formula (I) or (II) in the pesticide efficacy enhancer or the pesticide efficacy enhancer composition and the weight of the pesticide active ingredient The ratio is [compound represented by general formula (I) or (II)] / [pesticide drug substance] = 0.03 to 50, preferably 0.04 to 20,
More preferably, it is necessary to use 0.1 to 10. If this ratio is less than 0.03, the desired effect of enhancing the efficacy of the pesticide cannot be achieved. On the other hand, if this ratio exceeds 50, no further increase in the effect can be expected.

The formulation of the agricultural chemical composition of the present invention may be any of emulsions, wettable powders, granules, powders, flowable formulations and the like, and the formulation is not limited. Therefore, it may contain other additives according to the formulation type, for example, emulsifier, dispersant, carrier and the like. The method of using the pesticide potency enhancer according to the present invention includes a method of using the pesticide composition of the above-mentioned various dosage forms containing the pesticide potency enhancer, and a method of diluting the pesticide (one not containing the potency enhancer of the present invention). There is a method of using a pesticide efficacy enhancer attached separately at the time of use, and both methods can obtain the efficacy enhancing effect of the present invention.

If necessary, a chelating agent, a pH regulator, an inorganic salt, and a thickener may be added to the formulation of the agricultural chemical composition of the present invention.

The chelating agents usable in the present invention include:
Aminopolycarboxylic acid-based chelating agent, aromatic and aliphatic carboxylic acid-based chelating agent, amino acid-based chelating agent, ether polycarboxylic acid-based chelating agent, phosphonic acid-based chelating agent (for example, iminodimethylphosphonic acid (IDP), alkyldiphosphone) Acid (ADPA) or the like) or dimethylglyoxime (DG) or the like, which may be in the form of an acid or in the form of a salt such as sodium, potassium or ammonium. In the present invention, the chelating agent is used in an amount of 0.01 to 30 times, preferably 0.05 to 20 times, more preferably 0.1 to 15 times, 1 mole of the compound represented by the general formula (I) or (II). Is done.

Examples of the aminopolycarboxylic acid chelating agent include: a) RNX ₂ type compound b) NX ₃ type compound c) R-NX-CH ₂ CH ₂ -NX-R type compound d) R-NX-CH ₂ CH _2- NX type ₂ compounds and e) X ₂ N—R′-NX type ₂ compounds and all compounds of this type containing 4 or more X can be used. The formula X represents -CH ₂ COOH or -CH ₂ CH ₂ COOH, R represents a hydrogen atom, an alkyl group, a hydroxyl group, the substituents represent a hydroxyalkyl group or a known chelating compounds of this type, R 'is It represents an alkylene group, a cycloalkylene group and a group representing this type of known chelate compound. Representative examples thereof include ethylenediaminetetraacetic acid (EDTA), cyclohexanediaminetetraacetic acid (CDTA), nitrilotriacetic acid (NTA),
Iminodiacetic acid (IDA), N- (2-hydroxyethyl) iminodiacetic acid (HIMDA), diethylenetriaminepentaacetic acid (DTPA), N- (2-hydroxyethyl) ethylenediaminetriacetic acid (EDTA-OH) and glycol etherdiaminetetraacetic acid ( GEDTA) and salts thereof.

The aromatic and aliphatic carboxylic acid-based chelating agents usable in the present invention include citric acid, oxalic acid, glycolic acid, pyruvic acid or anthranilic acid and salts thereof. Further, the amino acid chelating agent that can be used in the present invention is glycine, serine, alanine, lysine, cystine,
Cysteine, ethionine, tyrosine or methionine, and salts and derivatives thereof. Furthermore, examples of the ether polycarboxylic acid-based chelating agent that can be used in the present invention include a compound represented by the following formula, a similar compound thereof, and a salt thereof (particularly, a Na salt).

[0034]

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Examples of the pH adjuster usable in the present invention include citric acid, phosphoric acid (pyrophosphate), gluconic acid and the like, and salts thereof.

Examples of the inorganic salts that can be used in the present invention include inorganic mineral salts such as clay, talc, bentonite, zeolite, calcium carbonate, diatomaceous earth, and white carbon, and inorganic ammonium salts such as ammonium sulfate and ammonium nitrate. , Ammonium phosphate, ammonium thiocyanate, ammonium chloride, ammonium sulfamate and the like.

The thickeners usable in the present invention include:
Any of natural, semi-synthetic and synthetic water-soluble thickeners can be used.Natural mucilage includes microorganism-derived xanthan gum, xanflow, plant-derived pectin, gum arabic, guar gum, and the like. Methylated, carboxyalkylated, hydroxyalkylated (including methylcellulose, carboxymethylcellulose, hydroxymethylcellulose, etc.), sorbitol and the like of starch derivatives, and polyacrylate, polymaleate, polyvinylpyrrolidone, pentaerythritol for synthetic mucilage Specific examples include ethylene oxide adducts.

Next, examples of the pesticidal drug substance used in the pesticidal composition of the present invention will be described, but the present invention is not limited thereto. Further, the efficacy enhancer for agrochemicals according to the present invention can be used safely without harm to various crops.

As fungicides, dasen (zinc ethylenebisdithiocarbamate), maneb (manganese ethylenebisdithiocarbamate), thiuram (bis (dimethylthiocarbamoyl) disulfide), manzeb (zinc ion coordinated manganese ethylenebisdithiocarbamate) , Bisdaisen (bisdimethyldithiocarbamoyl zinc ethylenebisdithiocarbamate), propineb (zinc propylene bisdithiocarbamate), and benzimidazole based on benomyl (methyl-1- (butylcarbamoyl) -2-benzimidazole carbamate), thiophanate methyl (1, 2-bis (3-methoxycarbonyl-2-thioureido) benzene) and vinclozolin (3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxa) Lysine 2,4 - dione), iprodione (3- (3,5-dichlorophenyl) -
N-isopropyl-2,4-dioxoimidazolidin-1
-Carboxamide), procymidone (N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide), triazine (2,4-dichloro-6-
(2-chloroanilino) -1,3,5-triazine), trifumizole ((E) -4-chloro-α, α, α-trifluoro-N- (1-imidazol-1-yl-2-propoxyethylidan) ) -O-toluidine), metalaxyl (methyl-N- (2-methoxyacetyl) -N- (2,6-
Xylyl) -D, L-alaninate), bitertanol (all-lac-1- (biphenyl-4-yloxy))
-3,3-Dimethyl-1- (1H-1,2,4-triazole-
1-yl) -2-butan-2-ol), pyrifenox (2,4-dichloro-2- (3-pyridyl) acetophenone- (EZ) -O-methyloxime), phenarimol (2,4
-Dichloro-α- (pyridin-5yl) benzhydryl = alcohol), triforine (1,4-bis- (2,2,2-trichloro-1-formamidoethyl) piperazine), iminoctadine acetate (1,1-iminiodi) (Octamethylene) diguanidium triacetate), organic copper (Oxine-c
opper), antibiotic fungicides (streptomycin, tetracycline, polyoxy, blasticidin S, kasugamycin, validamycin), triadimefon (1- (4-chlorophenoxy) -3,3-dimethyl-1- ( 1,2,4-triazol-1-yl) -2-butanone), isoprothiolane (diisopropyl-1,3-dithiolan-2-ylidenemalonate), daconyl (tetrachloroisophthalonitrile), pansoyl (5-ethoxy) -3-trichloromethyl-1,2,4-thiadiazole), fusalide (4,5,6,7-tetrachlorophthalolide)
, Chitazine P (O, O-diisopropyl-S-benzylthiophosphate), hinozane (O-ethyl-S, S-diphenyldithiophosphate), probenazole (3-allyloxy-1,2-benzisothiazole-1,1-) Dioxide), captan (N-trichloromethylthio-tetrahydrophthalimide), fosetyl (aluminum = tris (ethyl = phosphonate)) and the like.

In the case of insecticides, pyrethroid insecticides include fenvalereate (α-cyano-3-phenoxybenzyl-2- (4-chlorophenyl) -3-methylbutanoate), viceloid (cyano (4 -Fluoro-3-phenoxyphenylmethyl-3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate), and DDVP (dimethyl
2,2-dichlorovinyl phosphate), sumithion (ME
P) (O, O-dimethyl-O- (3-methyl-4-nitrophenyl) thiophosphate), marathon (S- [1,2, -bis (ethoxycarbonyl) ethyl] dimethylphosphorothiolthionate), Dimethoate (dimethyl S- (N-
Methylcarbamoylmethyl) dithiophosphate), ersan (S- [α- (ethoxycarbonyl) benzyl]
Dimethyl phosphorothiol thionate), visit
(O, O-dimethyl-O- (3-methyl-4-methylthiophenylthiophosphate)) and carbamate-based insecticides include Bassa (O-sec-butylphenylmethylcarbamate) and MTMC (m-tolylmethylcarbamate) , Meopal (3,4-dimethylphenyl-N-methylcarbamate), NAC (1-naphthyl-N-methylcarbamate),
Mesomyl (S methyl-N [(methylcarbamoyl)
Oxy] thioacetimide) and cartap (1,3-bis (carbamoylthio) -2- (N, N-dimethylamino) propane hydrochloride).

Examples of the natural insecticides include pyrethrins, piperonyl butoxides derived from pyrethrum, rotenones derived from legume shrubs, and nicotines (3- (1
-Methyl-2-pyrrolidinyl) pyridine sulfate) and the like. As an insect growth regulator (IGR agent), diflubenzuron (1- (4-chlorophenyl)-
3- (2,6-difluorobenzoyl) urea), teflubenzuron (1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea), chlorofluazuron ( 1- [3,5-dichloro-4
-(3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) urea, buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-3) , 4,5,6 −
Tetrahydro-2H-1,3,5-thiadiazin-4-one), phenoxycarb (ethyl-2- (4-phenoxyphenoxy) ethyl carbamate) and the like.

Of these insecticides, natural insecticides, particularly IGR agents, are preferred for use with the compounds of the general formula (I), and pyrethroids are preferred for use with the compounds of the general formula (II). Organophosphorus pesticides are preferred.

As acaricides, Smite (2-te)
rt-butyl-5- (4-tert-butylbenzylthio)-
4-chloropyridazin-3 (2H) -one), acid (2,4-dinitro-6-secondary-butylphenyldimethyl acrylate), chlormite (isopropyl-4,4-dichlorobenzylate), acal (ethyl −4,4-dichlorobenzylate), Kelsen (1,1−
Bis (p-chlorophenyl) -2,2,2-trichloroethanol), citrazone (ethyl-O-benzoyl-3-chloro-2,6-dimethoxybenzohydroxymate),
Omite (2- (p-tert-butylphenoxy) -cyclohexyl-2-propynylsulfite), osadan (hexakis (β, β-dimethylphenylethyl) distannoxane), hexthiazox (trans-5-
(4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide), amitraz (3-methyl-1,5-bis (2,4-xylyl) -1,3,5-triazapentane) 1,4-diene) and the like.

As the herbicide, acid amide herbicides such as stam (3,4-dichloropropionanilide,
DCPA), alachlor (2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) acetanilide) and the like. As urea herbicides, for example, DCMU (3- (3,4-
Dichlorophenyl) -1,1-dimethylurea), linuron (3- (3,4-dichlorophenyl) -1-methoxy-
1-methylurea) and the like. As dipyridyl herbicides, for example, paraquat (1,1′-dimethyl-4,4′-
Bipyridium dichloride), diquat (6,7-dihydrodipyrido [1,2-a: 2 ', 1'c] pyrazindium dibromide) and the like. Examples of the diazine herbicide include bromacil (5-bromo-3-sec-butyl-6-methyluracil) and the like. Examples of S-triazine herbicides include simazine (2-chloro-4,6-bis (ethylamino) -1,3,5-triazine) and simethrin (2,4-
Bis (ethylamino) -6-methylthio-1,3,5-triazine) and the like. Examples of nitrile herbicides include DBN (2,6-dichlorobenzonitrile) and the like. As dinitroaniline herbicides, for example, trifluralin (α, α, α-trifluoro-2,6-dinitro-
N, N-dipropyl-p-toluidine) and the like.
Examples of carbamate herbicides include benthiocarb (Saturn) (S-p-chlorobenzyl-N, N-diethylthiocarbamate), MCC (methyl-3,4-dichlorocarbanylate) and the like. As diphenyl ether herbicides, for example, NIP (2,4-dichlorophenyl-p-
Nitrophenyl ether) and the like. Examples of the benzoic acid-based herbicide include MDBA (dimethylamine-3,6-dichloro-o-anisate). Examples of the phenoxy herbicides include 2,4-D sodium salt (sodium 2,4-dichlorophenoxyacetate), mapica ([(4-chloro-o-toluyl) oxy] aceto-o-chloroanilide) and the like. Can be Examples of the organic phosphorus herbicide include glyphosate (N- (phosphonomethyl) glycine or a salt thereof), bialaphos (sodium salt of L-2-amino-4-[(hydroxy) (methyl) =
Phosphinoyl] butyryl-L-alanyl-L-alanine) and glyphosinate (ammonium-DL-homoalanine-4-yl (methyl) phosphinate). Examples of the aliphatic herbicide include TCA sodium salt (sodium trichloroacetate).

Among these herbicides, acid amide herbicides, diazine herbicides, nitrile herbicides, dinitroaniline herbicides, benzoic acid herbicides, and organophosphorus herbicides are preferred, and especially organophosphorus herbicides. Herbicides, especially bialaphos (sodium salt of L-2-amino-4)
-[(Hydroxy) (methyl) = phosphinoyl] butyryl-L-alanyl-L-alanine), glyphosinate (ammonium-DL-homoalanine-4-yl (methyl) phosphinate) or glyphosate (N- (phosphonomethyl) glycine or a salt thereof) Is preferred.

Further, examples of plant growth regulators include MH (maleic acid hydrazide), esrel (2-chloroethylphosphonic acid), UASTA, bialaphos and the like.

Further, the pesticidal composition of the present invention may be used by mixing one or more kinds of plant growth regulators, fertilizers, preservatives and the like other than those described above.

In the present invention, the pesticidal potency enhancer according to the present invention is contained for the purpose of sterilization, insecticidal, acaricidal, weeding or plant growth control.
~ 50 times, preferably 0.04 to 20 times, more preferably still
An agrochemical composition containing 0.1 to 10 times is used.

The agrochemical formulation using the agrochemical efficacy enhancer of the present invention includes: (a) a package of at least one kind of the compound represented by the general formula (I) or (II); (B) A composition comprising at least one compound represented by the general formula (I) or (II) and at least one surfactant other than the compound A packaged package of a pesticide composition comprising a packaged package of an agrochemical composition (c) one or more packaged packages of the compound represented by the general formula (I) or (II); Agrochemical formulation comprising at least one package of surfactants other than the compound and a package of agricultural chemical composition (d) 1 of the compound represented by the above general formula (I) or (II) A pesticide formulation comprising a divided package of a composition comprising at least one species and a chelating agent, and a divided package of an agrochemical composition (e) 1 of the compound represented by the general formula (I) or (II) More than species and sharp A packaged package of a composition comprising a composition, a packaged package of at least one surfactant other than the compound, and a packaged package of a pesticide composition; A package for a composition comprising at least one compound represented by the formula (I) or (II), at least one surfactant other than the compound, and a chelating agent, and a package for an agrochemical composition. An agricultural chemical formulation comprising a package. Here, the pesticidal composition to be a divided package includes a pesticidal drug substance and an optional component in an arbitrary ratio, means an emulsion, a form of a wettable powder and the like, and is used for the pesticide of the present invention. A pesticide composition comprising an efficacy enhancer and a pesticide drug substance is different. The form in each divided package is not limited, and is prepared according to the use and purpose.

[0050]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 Various pesticide efficacy enhancer compositions shown in Tables 3 and 4 were prepared using the compounds shown in Tables 1 and 2 and, if necessary, the surfactants and chelating agents shown in Tables 3 and 4. Hereinafter, abbreviated as active ingredient)
Was prepared.

[0052]

[Table 1]

[0053]

[Table 2]

[0054]

[Table 3]

[0055]

[Table 4]

[0056]

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Each of the above active ingredients was dissolved in ion-exchanged water so as to obtain a diluent of 0.2% by weight. Got
Using a 0.2% by weight diluent, a commercially available herbicide, a round-up solution (41% by weight effective as glyphosate isopropylamine salt), a Bambell-D solution (50.0% by weight effective as MDBA dimethylamine salt), Herbiace About each of water solvent (effective amount as bialaphos 20% by weight)
By performing a 300-fold dilution, three types of pesticidal compositions were obtained for one active ingredient.

For the greenhouse test, seeds of mehishiba were sowed and germinated in a pot having an inner diameter of 12 cm into which a soil obtained by mixing fertilized soil, river sand and commercially available culture soil at a ratio of 7: 2: 1 (weight ratio) collected from a paddy field was used. Let it. Pots with abnormal growth are discarded in order to increase the uniformity of individuals between the pots. A pot in which the height of the crabgrass grew to about 18 cm was used for the test. The pesticide composition was sprayed uniformly over the whole crabgrass in the pot at a rate equivalent to 10 liters / are using a spray gun (RG type, manufactured by Iwata Coating Machine Industry Co., Ltd.) to reduce the herbicidal effect. evaluated.

The evaluation of the herbicidal efficacy was carried out by weighing the above-ground fresh weight on the 10th day after the spraying treatment, and expressed as a percentage of weed-killing based on the above-ground fresh weight of the untreated plot (see the following formula).

[0060]

(Equation 1)

Tables 5 and 6 show the herbicidal rates of each pesticidal composition.

[0062]

[Table 5]

[0063]

[Table 6]

Example 2 An adult of Kanzawa spider mite female was placed on a leaf disk of bean 30 animals per group in three repetitions, and then cultured at 24 hours at 25 ° C. Thereafter, the entire leaf disk was immersed in the test solution for 5 seconds, taken out of the test solution, and allowed to stand at 25 ° C. for 48 hours, observed, and the acaricidal rate was determined based on the case of no treatment (see the following formula). Nissolan wettable powder (effective as hexithiazox 10% by weight), Osadan wettable powder 25 (effective as fenbutatin oxide 25% by weight)
In each case, a 2000-fold diluted solution was used, and the same pesticide efficacy enhancer as that used in Example 1 was used. 0.1% by weight of active ingredient of pesticide efficacy enhancer in diluent
Was prepared. The same procedure was carried out when no potency enhancer was used. The results are shown in Tables 7 and 8.

[0065]

(Equation 2)

[0066]

[Table 7]

[0067]

[Table 8]

Example 3 (1) A third-instar larva of a planthopper was cultured, and the efficacy of the insecticide was tested by a dipping method in a group of 10 animals per group, three in a row.
The insecticidal rate was determined in the same manner as the miticide rate. Sumithion emulsion, a commercially available insecticide (effective as MEP, 50% by weight), Agrosulin wettable powder (effective as dipermethrin, 6% by weight)
2,000 times diluted solution for each of the above, and the effect enhancer for agrochemicals used in Example 1 had a concentration of 0.1 in the diluted solution.
It was used so that it might become the weight%.

(2) Further, the test solution was immersed in the whole leaf disk of the beans for 5 seconds, taken out from the test solution, air-dried, and then cultivated in advance, and ten third-instar larvae of the planthopper were placed on the leaf disk. After culturing at 25 ° C. for 10 days, the number of dead planthoppers was visually examined, and the efficacy of the insecticide was tested. The test was repeated three times, and the insecticidal rate was determined in the same manner as the acaricidal rate. As the insecticide, a 2000-fold diluted solution of a commercially available demiline wettable powder (effective component: 23.5% as diflubenzuron) was used. The pesticide efficacy enhancer used in Example 1 had a concentration of 0.1% by weight in the diluted solution. %. The above results are shown in Tables 9 to 10.

[0070]

[Table 9]

[0071]

[Table 10]

Example 4 A fungicide-resistant bacterium, Botrytis gray mold
cinerea) (10 ⁷ cells / ml) was sprayed on cucumber seedlings (developing three true leaves) at a rate of 10 ml per pot.
C. and 90% relative humidity for 1 day.

Thereafter, a commercially available fungicide, benlate wettable powder (effective amount as benomyl, 50% by weight) was diluted 2000-fold with the 2500-fold diluted solution of the active ingredient used in Example 1, and then 5 ml per pot was diluted. Sprayed one by one. Then, it was allowed to stand at 25 ° C. and 85% relative humidity, the number of lesions was counted, and the control value for the untreated plot was calculated by the following formula. The results are shown in Tables 11 and 12.

[0074]

(Equation 3)

[0075]

[Table 11]

[0076]

[Table 12]

In Examples 1 to 4, the efficacy of the pesticide efficacy enhancer of the present invention was compared with the case where a general tertiary amine or a cationic surfactant was used as the pesticide efficacy enhancer (comparative product). The test is shown. As is clear from Tables 5 to 12, the pesticidal efficacy enhancer of the present invention exhibited a remarkable effect and was at a practical level, but the comparative product showed a slight increase in pesticide efficacy, but was at a practical level. There was no effect up to that point.
Therefore, it is understood that the pesticide efficacy enhancer of the present invention specifically enhances the pesticide efficacy as compared with general tertiary amines or cationic surfactants.

Example 5 A round-up herbicide (active ingredient 41% by weight)
The same test as in Example 1 was carried out using the active ingredients 13, 21 and 28 of Example 1 as the potency enhancers in the amounts shown in Table 13. Was. Table 13 shows the results. In Table 13, “pesticide drug substance” means an active ingredient of a herbicide.

[0079]

[Table 13]

Example 6 Sumithion emulsion [50% by weight of active ingredient (MEP)
)] As the potency enhancer, using the active ingredient 13 and the active ingredient 30 of Example 1 in the amounts shown in Table 14 to obtain the same as (1) of Example 3. The test was performed. Table 14 shows the results. In Table 14, "pesticide drug substance" means an active ingredient of an insecticide.

[0081]

[Table 14]

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification code FI A01N 53/08 A01N 55/04 F 55/04 57/14 E 57/14 57/20 G 57/20 L 53/00 508C ( 56) References JP-A-61-277603 (JP, A) JP-A-4-41406 (JP, A) JP-A-2-142708 (JP, A) JP-A-62-198649 (JP, A) European Patent Application Publication 46336 (EP, A1) US Patent 3,660,183 (US, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A01N 25/30 A01N 37/40 A01N 43/78 A01N 47/34 A01N 47 / 38 A01N 53/08 A01N 55/04 A01N 57/14 A01N 57/20 CA (STN) REGISTRY (STN)

Claims (15)

(57) [Claims] An agricultural chemical efficacy enhancer comprising a compound represented by the general formula (I) as an active ingredient. Embedded image [Wherein, R ¹ : a linear or branched alkyl group or alkenyl group having 5 to 29 carbon atoms R ² , R ³ : the same or different, a hydrogen or a methyl group, or a mixture of a hydrogen and a methyl group, m: 1 to 1 on average Number of 30 n: Number of 1 to 30 on average R ⁶ : represents a linear or branched alkyl group or alkenyl group having 1 to 29 carbon atoms. ] 2. A agricultural chemical enhancer of claim 1 Symbol placement R ^2, R ³ are both hydrogen compound represented by the general formula (I). Wherein R ^2, R ³ are agricultural chemical enhancer according to claim 1 or 2, wherein a mixture of hydrogen and methyl group of the compound represented by the general formula (I). 4. The compound represented by the general formula (I) wherein m + n is an average number in the range of 2 ≦ m + n <25.
4. The potency enhancer for pesticides according to any one of 3 ). 5. An agricultural chemical efficacy enhancer comprising a compound represented by the general formula (II) as an active ingredient. Embedded image [Wherein, R ⁷ : a linear or branched alkyl group or alkenyl group having 5 to 29 carbon atoms R ⁸ : hydrogen or a methyl group or a mixture of hydrogen and a methyl group p: a positive number of 1 to 30 on average X: hydrogen, It represents Na, K, and NH ₄ or an organic ammonium cation. ] 6. The method according to claim 5, wherein R ^{8 of the} compound represented by the general formula (II) is hydrogen. 7. A pesticide efficacy enhancer comprising at least one compound according to any one of claims 1 to 6 and a chelating agent in an amount of 0.01 to 30 moles per 1 mole of the compound. Composition. 8. An agricultural chemical efficacy enhancer composition comprising at least one compound according to any one of claims 1 to 4 and at least one surfactant other than the compound. 9. One or more of the compounds according to any one of claims 1 to 4 , and one or more of a surfactant other than the compound, and 0.01 to 30 moles per 1 mole of the compound. An agricultural chemical efficacy enhancer composition comprising a chelating agent. 10. A surfactant nonionic surfactant or anionic surfactant in a claim 8 or 9 agricultural chemical enhancer composition. 11. The method of claim 5 or with one or more 6 compounds described, agricultural chemical enhancer composition comprising a one or more surfactants other than the compounds. 12. A compound comprising at least one compound according to claim 5 or 6 , at least one surfactant other than the compound, and a chelating agent in an amount of 0.01 to 30 moles per 1 mole of the compound. An agricultural chemical efficacy enhancer composition comprising: 13. surfactant nonionic surfactant or claim 11 or 12 agricultural chemical enhancer composition wherein the cationic surfactant. 14. An agrochemical potency enhancer or an agrochemical potency, comprising the agrochemical potency enhancer or the agrochemical potency enhancer composition according to any one of claims 1 to 13 and an agrochemical drug substance. In the enhancer composition, the weight ratio of the compound represented by the general formula (I) or (II) and the pesticide active ingredient is [compound represented by the general formula (I) or (II)] / [pesticide active substance ] = 0.03 to 50. 15. The pesticidal composition according to claim 14 , wherein the pesticidal active ingredient is selected from active ingredients of fungicides, insecticides, acaricides, herbicides and plant growth regulators.