JPH06219908A - Potency-increasing agent for agrichemical and agricultural chemical composition - Google Patents

Abstract

PURPOSE:To provide the potency-increasing agent capable of being safely used without giving chemical damages to crops, having excellent potency-increasing actions for various agrichemicals and used for the agrichemicals. CONSTITUTION:The agrichemical potency-increasing agent containing as an active ingredient (A) a compound of formula I [A is H, CH2CH2-CN, CH2 CH2-COOH, group of formula II (R is H, CH3; n is 2-9 ; p is 0-30), etc.; B, C, D are H, CH3, CH2CH3, group of formula III (i is 2-6; j is 1-10), CH2COOH, CH2COO<->, etc.; R<1>-R<2> are 4-30C alkyl or alkenyl; X<-> is counter ion], e.g. a compound of formula IV, (B) a compound of formula V [Y, Z are 6-30C alkyl or alkenyl, C3H6NHCOR<6>, C3H6OR<6> (R<6> is 5-29C alkyl or alkenyl), etc.; R<4> is 1-4C alkyl, group of formula VI (R<5> is H, CH3; q is 1-30)] e.g. a compound of formula VII, or a compound of formula VIII [R<7>, R<8> are 1-4C alkyl, alkenyl, etc.; R<9> is 6-36C alkyl, group of formula IX (R<10> is H, CH3; R<11> is 5-15C alkyl; m is 2-9; p is 0-30), etc.; W is group of formula X, NHCOR<11>, etc.,], e.g. a compound of formula XI, as an active ingredient.

Description

Detailed Description of the Invention

[0001]

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

[0002]

2. Description of the Related Art Insecticides, fungicides, herbicides,
Pesticides such as acaricides and plant growth regulators are used in dosage forms such as emulsions, wettable powders, granules, powders and flowable agents. At that time, various contrivances have been made in terms of the physical properties of the preparation in order to sufficiently bring out the effect of the pesticidal drug substance, but it is currently difficult to further enhance the effect of the pesticide by devising the preparation. Further, since the development of new pesticides is more difficult, it is of great industrial significance to further enhance the activity of existing pesticides.

Up to now, surfactants composed of various nitrogen-containing compounds such as quaternary ammonium salts, betaines and amine oxides have been known as those having an effect of enhancing the activity of agricultural chemicals (Japanese Patent Laid-Open No. 2000-242242). Sho 63-145205
issue). Among them, it is known that a quaternized or further polyoxyethylenated long chain amine is particularly effective. Although the counter ion of the above-mentioned compound having the activity-enhancing effect of a pesticide is halogen, its effect-enhancing effect was not satisfactory.

[0004]

[Means for Solving the Problems] The inventors of the present invention have made further intensive studies from the viewpoint of enhancing the efficacy of pesticides by combining a pesticide raw material and an ammonium salt. The present invention has been completed by discovering that the compound (1) has a potentiating effect on various pesticides.

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

[0006]

[Chemical 8]

[0007]

[Chemical 9]

[0008] R ¹ to R ^3: the same or different alkyl group of 4 to 30 carbon atoms or an alkenyl group X ^-: a counter ion. However, one of B, C and D is -CH ₂
COO ^- or _{-CH 2 CH (OH) CH 2} SO 3 - may represent either, X
^- it does not exist. Represents Further, the present invention provides a compound represented by the general formula (I
The present invention provides an agrochemical potency enhancer containing the compound represented by I) as an active ingredient.

[0009]

[Chemical 10]

[Wherein Y and Z are the same or different and are an alkyl group or an alkenyl group having 6 to 30 carbon atoms,

[0011]

[Chemical 11]

--C ₃ H ₆ OR ⁶ or --CH ₂ CH (OH) CH ₂ OR ⁶ (wherein R ⁵ ; --H, --CH ₃ or a mixture thereof, R ⁶ ; carbon number of 5 to 29
Alkyl group or alkenyl group, n = 2 to 9, m = 2
9, p = 0 to 30), but Y and Z cannot simultaneously be an alkyl group or an alkenyl group having 6 to 30 carbon atoms.

[0013]

[Chemical 12]

R ^{6 is} an alkyl or alkenyl group having 5 to 29 carbon atoms X ⁻ : represents a counter ion. ].

The present invention also provides an agrochemical potency enhancer containing a compound represented by the general formula (III) as an active ingredient.

[0016]

[Chemical 13]

[0017]

[Chemical 14]

The present invention also provides the above general formulas (I) to (III)
The present invention provides an agrochemical efficacy enhancer composition comprising at least one compound represented by and one or more surfactants other than the compound as active ingredients. Furthermore, the present invention comprises any one of the above-mentioned pesticidal potency enhancers and pesticide raw materials, wherein the weight ratio of the pesticidal potency enhancers and pesticide raw materials is pesticide potency enhancer / pesticide raw material = 0.05. A pesticide composition comprising a pesticide composition of 50 to 50 and a packaged package of at least one of the compounds represented by the general formulas (I) to (III), and a packaged package of a pesticide raw material. It is a thing.

In the above general formulas (I) to (III), R ¹ to
R ³ , R ⁶ , R ⁹ and R ¹¹ all preferably have 7 to 22 carbon atoms,
Further, p is preferably 0 to 20 on average, and q is preferably 1 to 20 on average.

Among the compounds represented by the general formula (I), particularly suitable ones are those in which A is -C _n H _2n O-COR ² , -C _m H _2m NH-COR ²
And R ² is an alkyl or alkenyl group having 10 to 30 carbon atoms, and B, C and D are H or —CH ₃ .

The compound of the general formula (I) according to the present invention is obtained by reacting, for example, N, N-dialkylaminoalkylamine with a nitrile compound, and then reacting a triamine obtained by hydrogenation with a fatty acid to give a diamine. It is obtained by producing amidoamine and then quaternizing this diamidoamine with an alkyl chloride or the like. Of course, the method for producing the compound of the general formula (I) according to the present invention is not limited to this.

Among the compounds represented by the general formula (II), R ⁴ is an alkyl group having 1 to ⁴ carbon atoms, Y, Z
One of the groups has an ester group or an amide group, and the other has an alkyl group.

The compound of the general formula (II) according to the present invention is prepared, for example, by reacting the secondary amine with an epoxy compound or a haloalcohol to produce an aminoalcohol and esterifying with a fatty acid or a fatty acid ester. The ester amine of the present invention can be obtained. Alternatively, the amidoamine of the present invention can be obtained by subjecting the secondary amine to an acrylonitrile addition reaction, and then subjecting the amine obtained by the hydrogenation reaction to amidation with a fatty acid or a fatty acid ester. Of course, the method for producing the compound of the general formula (II) according to the present invention is not limited to these.

Suitable compounds among the compounds represented by the general formula (III) are those in which R ⁷ and R ⁸ are the same or different and have 1 to 4 carbon atoms.
Alkyl group, R ⁹ is a group having an ester group or an amide group, W is a group having an ester group or an amide group, and particularly suitable ones are those in which R ⁷ and R ⁸ have the same or different carbon numbers. Examples thereof include those having 1 to 2 alkyl groups, R ⁹ having an ester group, and W having an amide group.

In the compound of the general formula (III) according to the present invention, for example, the tertiary amine obtained by hydrogenation reaction after the cyanoethylation reaction of N-lower alkylalkanolamine is condensed with fatty acid. Then, it is manufactured by quaternization by a usual method. It can also be produced by condensing N, N-dimethylpropanediamine with a fatty acid and then quaternizing with an alkyl halide. Of course, the method for producing the compound of the general formula (III) according to the present invention is not limited to these.

As the counter ion in the general formulas (I) to (III), for example, halogen such as Cl, Br, I, etc., alkyl sulfuric acid ester, alkylbenzene sulfonic acid, alkylnaphthalene sulfonic acid, fatty acid, alkyl phosphoric acid ester. ,
Examples thereof include anionic oligomers and anionic polymers.

The potency enhancer for agricultural chemicals comprising the compounds of the above general formulas (I) to (III) of the present invention has no phytotoxicity when used in combination with the agricultural chemical bulk, and increases the efficacy of the agricultural chemical bulk by 2 to 3 times. You can

The potentiator for agricultural chemicals containing the compound represented by the general formula (I), the general formula (II) or the general formula (III) according to the present invention as an active ingredient is remarkable regardless of the kind of the structure of the agricultural chemical. The mechanism as to whether or not it exhibits a force-enhancing action is not necessarily clear, but one of them is that the efficacy-enhancing agent of the present invention has a very strong solubilizing power for pesticides, so that the pesticides are made into fine particles to form plant surface or insect bodies and fungi. It is thought to promote penetration into the body.

When at least one of the compounds represented by the general formulas (I) to (III) according to the present invention is used in combination with a surfactant other than these, the compounds represented by the general formulas (I) to (III) are represented. The amount of the compound represented by the general formulas (I) to (III) to be used can be reduced while maintaining the effect of the compound for enhancing pesticide efficacy. As the surfactant, a nonionic surfactant, an anionic surfactant, a cationic surfactant and an amphoteric surfactant, or a mixture thereof can be used.

Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylaryl ether formaldehyde condensate, polyoxyalkylene aryl ether, polyoxyalkylene alkyl ester, 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, a mixture of two or more of these, and the like.

Examples of cationic surfactants are alkylamine ethylene oxide adducts, alkylamine propylene oxide adducts such as tallow amine ethylene oxide adducts, oleyl amine ethylene oxide adducts, soy amine ethylene oxide adducts, coco amines. There are ethylene oxide adducts, synthetic alkyl amine ethylene oxide adducts, octyl amine ethylene oxide adducts and the like and mixtures thereof.

Typical anionic surfactants can be obtained in an aqueous solution or a solid state, and examples thereof include 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 alkylnaphthalene sulfonate, alkyl diphenyl ether sulfonate, olephinic sulfonate, mono and dialkyl phosphate, polyoxyalkylene mono and dialkyl phosphate, polyoxyalkylene mono and diphenyl ether phosphate, polyoxyalkylene Mono- and di-alkyl phenyl ether phosphates, polycarboxylic acid salts, fatty acid salts, linear and branched alkyl polyoxyalkylene ether acetic acid and its salts, alkenyl polyoxyalkylene ether acetic acid and its salts, stearic acid and its salts, oleic acid and Its salt, N-methyl fatty acid 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, monatelix (Mon
aterics, Milanols, betaines, Lonzaines, other amine oxides, and mixtures thereof.

Of these surfactants, nonionic surfactants are particularly preferable. Among them, ester type ones such as polyoxyalkylene sorbitan ester and polyoxyalkylene alkyl glycerol ester, polyoxyalkylene alkyl ether and polyoxyalkylene alkyl phenyl ether are preferable.

In the efficacy enhancer for agricultural chemicals, which comprises the compounds represented by the general formulas (I) to (III) and other surfactants as active ingredients, the agrochemical efficacy enhancers represented by the general formulas (I) to (III) The preferred combined ratio of the total amount of the compound and the surfactant is (general formula (I) ~
(Total amount of compound represented by (III)] / [surfactant other than the compound] = 1/10 to 50/1 (weight ratio), and more preferably 1/1 to 10/1.

The agrochemical composition of the present invention comprises the agrochemical potency enhancer as described above and the agrochemical raw material. Here, the pesticide raw material refers to the active ingredient of the pesticide. In the pesticidal composition of the present invention, the pesticidal potency enhancer has a weight ratio of the pesticidal potency enhancer and the pesticide bulk, the pesticidal potency enhancer / pesticide bulk = 0.05 to 50, preferably 0.05 to 20, Preferably 0.
It is necessary to use it so that it becomes 1 to 10. This percentage
If it is less than 0.05, the intended effect of enhancing the efficacy of the pesticide cannot be sufficiently achieved. On the other hand, even 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 formulation is not limited. Therefore, it may contain other additives depending on its formulation type, for example, an emulsifier, a dispersant, a carrier and the like. The method for using the agrochemical potency enhancer according to the present invention includes a method of using the above-mentioned various types of agrochemical compositions containing the agrochemical potency enhancer and dilution of the agrochemical (not containing the potency enhancer of the present invention). There is a method of using a separately added potency enhancer for agricultural chemicals at the time of use, and any of them can obtain the potency enhancing effect of the present invention.

A chelating agent, a pH adjusting agent, an inorganic salt, and a thickening agent may be added to the formulation of the agricultural chemical composition of the present invention, if necessary.

The chelating agent which can be used in the present invention includes
Aminopolycarboxylic acid type chelating agent, aromatic and aliphatic carboxylic acid type chelating agent, amino acid type chelating agent, ether polycarboxylic acid type chelating agent, iminodimethylphosphonic acid (IDP), dimethylglyoxime (DG) or alkyldiphosphon Acids (ADPA) and the like, which may be in the form of the acid as it is or in the form of a salt such as sodium, potassium and ammonium.

Aminopolycarboxylic acid type chelating agents 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 ₂ type compounds and e) X ₂ N—R′-NX ₂ type and all compounds of this type containing 4 or more X can be used. In the above formula, X represents -CH ₂ COOH or -CH ₂ CH ₂ COOH, R represents a hydrogen atom, an alkyl group, a hydroxyl group, a hydroxyalkyl group or a substituent representing a known chelate compound of this type, and R'is It represents an alkylene group, a cycloalkylene group and a group representing a known chelate compound of this type. Typical examples of these are 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.

Aromatic and aliphatic carboxylic acid type chelating agents which can be used in the present invention are citric acid, oxalic acid, glycolic acid, pyruvic acid or anthranilic acid and salts thereof. The amino acid-based chelating agents that can be used in the present invention include glycine, serine, alanine, lysine, cystine,
Examples include cysteine, ethionine, tyrosine or methionine and salts and derivatives thereof. Furthermore, examples of the ether polycarboxylic acid type chelating agent that can be used in the present invention include compounds represented by the following formulas, similar compounds thereof and salts thereof (especially Na salt).

[0042]

[Chemical 15]

The pH adjuster usable in the present invention is citric acid, phosphoric acid (pyrophosphoric acid), gluconic acid or the like or salts thereof.

Examples of the inorganic salts that can be used in the present invention include inorganic mineral salts such as inorganic salt 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 thickening agents that can be used in the present invention include:
Any of natural, semi-synthetic and synthetic water-soluble thickeners can be used, and in natural mucilages, xanthan gum derived from microorganisms, Zanflo, pectin derived from plants, gum arabic, guar gum, etc., semi-synthetic mucilages include cellulose or Methylated products of starch derivatives, carboxyalkylated products, hydroxyalkylated products (including methylcellulose, carboxymethylcellulose, hydroxymethylcellulose, etc.), sorbitol, etc., and synthetic mucilages, polyacrylic acid salts, polymaleic acid salts, polyvinylpyrrolidone, pentaerythritol. Specific examples thereof include ethylene oxide adducts.

Next, examples of the agrochemical raw materials used in the agrochemical composition of the present invention will be given, but the agrochemical raw materials are not limited thereto. Moreover, the efficacy enhancer for agricultural chemicals according to the present invention has no chemical damage to various crops and can be safely used.

As the bactericide, daicene (zinc ethylene bisdithiocarbamate), manneb (manganese ethylene bisdithiocarbamate), thiuram (bis (dimethylthiocarbamoyl) disulfide), manzeb (zinc ion coordinated manganese ethylene bisdithiocarbamate) , Bisdaisene (bisdimethyldithiocarbamoyl zinc ethylene bisdithiocarbamate), propineb (zinc propylene bisdithiocarbamate), benzimidazole-based benomyl (methyl-1- (butylcarbamoyl) -2-benzimidazole carbamate), thiophanate methyl (1, 2-bis (3-methoxycarbonyl-2-thioureido) benzene), 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-dioxoimidazolidine-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-propoxyethylidane) ) -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), triadimefon (1- (4-chlorophenoxy) -3,3-dimethyl-
1- (1,2,4-triazol-1-yl) -2-butanone), isoprothiolane (diisopropyl-1,3-dithiolane-2-ylidenemalonate), daconyl (tetrachloroisophthalonitrile), pansoyl ( 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole), rapside (4,5,6,7-tetrachlorophthalolide), kitadine P (O, O-diisopropyl-S-benzylthiophosphate), Hinozan (O-ethyl-S, S-diphenyldithiophosphate), probenazole (3-allyloxy-1,2-benzisothiazole-1,1-dioxide), captan (N-trichloromethylthio-tetrahydrophthalimide) and the like. To be

In the case of insecticides, pyrethroid insecticides include fenvalereate (α-cyano-3-phenoxybenzyl-2- (4-chlorophenyl) -3-methylbutanoate) and viceloid (cyano (4 -Fluoro-3-phenoxyphenylmethyl-3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate), as an organic phosphorus insecticide, 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] dimethylphosphorothiothionate), Dimethoate (dimethyl S- (N-
Methylcarbamoylmethyl) dithiophosphate), ersan (S- [α- (ethoxycarbonyl) benzyl]
Dimethyl phosphorothiol thionate), Visit
(O, O-dimethyl-O- (3-methyl-4-methylthiophenylthiophosphate)), as a carbamate insecticide, bassa (O-sec-butylphenylmethylcarbamate), MTMC (m-tolylmethylcarbamate) , Meopearl (3,4-dimethylphenyl-N-methylcarbamate), NAC (1-naphthyl-N-methylcarbamate),
In addition, Methomyl (S methyl-N [(methylcarbamoyl)
[Oxy] thioacetimide), cartap (1,3-bis (carbamoylthio) -2- (N, N-dimethylamino) propane hydrochloride) and the like.

As acaricide, smite (2-te
rt-Butyl-5- (4-tert-butylbenzylthio)-
4-chloropyridazin-3 (2H) -one), acriside (2,4-dinitro-6-secondary-butylphenyldimethylacryleate), chlormite (isopropyl-4,4-dichlorobenzileate), akar (ethyl) −4,4-Dichlorobenzilate), 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-propynyl sulfite), osadan (hexakis (β, β-dimethylphenylethyl) distannoxane), hexithiaxox (trans-5-
(4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide), amitrazs (3-methyl-1,5-bis (2,4-xylyl) -1,3,5-triazapenta -1,4-diene) and the like.

The herbicides include acid amide herbicides such as stam (3,4-dichloropropionanilide,
DCPA), alachlor (2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) acetanilide), and the like. As a urea-based herbicide, for example, DCMU (3- (3,4-
Dichlorophenyl) -1,1-dimethylurea), linuron (3- (3,4-dichlorophenyl) -1-methoxy-
1-methylurea) and the like. Examples of dipyridyl herbicides include paraquat (1,1′-dimethyl-4,4′-
Bipyridin dichloride), diquat (6,7-dihydrodipyrido [1,2-a: 2 ', 1'c] pyrazinedium dibromide), and the like. Examples of diazine-based herbicides 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 cimetrin (2,4-
Bis (ethylamino) -6-methylthio-1,3,5-triazine) and the like. Examples of nitrile herbicides include DBN (2,6-dichlorobenzonitrile). Examples of the dinitroaniline herbicides include trifluralin (α, α, α-trifluoro-2,6-dinitro-
N, N-dipropyl-p-toluidine) and the like.
Examples of the carbamate herbicide include benchocarb (saturn) (Sp-chlorobenzyl-N, N-diethylthiocarbamate), MCC (methyl-3,4-dichlorocarbanilate) and the like. Examples of diphenyl ether herbicides include NIP (2,4-dichlorophenyl-p-
Nitrophenyl ether) and the like. Examples of phenolic herbicides include PCP (sodium pentachlorophenoxide) and the like. Examples of the benzoic acid type herbicides include MDBA (dimethylamine-3,6-dichloro-o-anisate) and the like. Examples of phenoxy herbicides include 2,4-D sodium salt (sodium
2,4-dichlorophenoxyacetate), mapica ([(4-
Chloro-o-toluyl) oxy] aceto-o-chloroanilide) and the like. As organophosphorus herbicides,
Glyphosate (N- (phosphonomethyl) glycine),
Bialaphos (sodium salt of L-2-amino-4-[(hydroxy) (methyl) = phosphinoyl]
Butyryl-L-alanyl-L-alanine), glyphosinate (ammonium-DL-homoalanin-4-yl (methyl) phosphinate) and the like. Examples of the aliphatic herbicide include TCA sodium salt (sodium trichloroacetate) and the like.

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

Further, one or more kinds of plant growth regulators, fertilizers, preservatives and the like other than the above may be mixed and used in the agrochemical composition of the present invention.

In the present invention, for the purpose of sterilization, insecticidal, acaricidal, herbicidal or plant growth regulation, the agrochemical potency enhancer according to the present invention is contained, and the agrochemical potency enhancer is added to a pesticide bulk of 0.05.
To 50 times, preferably 0.05 to 20 times, and even more preferably
An agrochemical composition containing 0.1 to 10 times is used.

The agrochemical preparation using the agrochemical potency enhancer of the present invention includes (a) at least one sachet of the compounds represented by the general formulas (I) to (III), and an agrochemical composition. (B) Separate packaging of a composition comprising at least one compound represented by the general formulas (I) to (III) and one or more surfactants other than the compound. Body, an agricultural chemical formulation comprising a packaged package of an agrochemical composition (c) at least one packaged package of the compounds represented by the general formulas (I) to (III), and a surfactant other than the compound Agent 1
An agrochemical preparation comprising a packaged package of at least one kind and a packaged package of an agricultural chemical composition can be mentioned. Here, the pesticide composition to be a divided package means an emulsion, a wettable powder or the like in the form of an emulsion, a wettable powder, etc., which contains a pesticide raw material and an arbitrary component in an arbitrary ratio. It is a separate agrochemical composition comprising a potency enhancer and an agrochemical bulk. The form in each divided package is not limited, and may be prepared according to the use and purpose.

[0055]

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

Production Example 1 (a) 204 g of N, N-dimethylaminopropylamine was placed in a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, and acrylonitrile 106 was added while keeping the liquid temperature at 60 ° C or lower.
g was added dropwise over 1 hour. After the completion of dropping, aging was carried out for 5 hours at the same temperature. After the aging, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge.
Subsequently, Raney Ni 30 g was added and the hydrogen pressure was 20 kg / cm ² ·.
The hydrogenation reaction was carried out for 6 hours while maintaining at G. After completion of the reaction, Raney Ni was filtered and the reaction product was distilled to obtain 180 g of triamine. The boiling point was 86 ° C / 0.2 mmHg.

(B) 78 g of the above triamine and 285 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, and the temperature was raised to 150 ° C. At the same temperature
The amidation reaction was carried out for 12 hours while distilling off the produced water to obtain 350 g of the desired diamidoamine. The following structure of this diamidoamine was confirmed from the NMR spectrum and IR spectrum.

[0058]

[Chemical 16]

(C) Next, the diamidoamine obtained above was quaternized with methyl chloride by a conventional method to obtain the following compound (hereinafter referred to as active ingredient 1).

[0060]

[Chemical 17]

Example 1 The active ingredient 1 obtained in Production Example 1 was dissolved in ion-exchanged water so as to obtain a 0.2% by weight diluted solution. Using the obtained 0.2% by weight diluted solution, a commercially available herbicide, Roundup solution (41% by weight effective as glyphosate isopropylamine salt), Carmex wettable powder (78.5% by weight effective as DCMU), Herbiace water solvent (effective as bialaphos
20% by weight) of each of them was diluted 300 times to obtain 3 kinds of pesticide compositions of the present invention for each active ingredient. Inner diameter 12 cm containing soil mixed with fertile soil, river sand, and commercially available culture soil at a ratio of 7: 2: 1 (weight ratio) collected from paddy fields for greenhouse testing
Sowing seeds of crabgrass are sown in a pot and germinated. Pots with abnormal growth are discarded to increase the uniformity of individuals between pots. A pot in which the plant height of the crabgrass was grown to about 18 cm was used for the test. The pesticide composition was sprayed with a spray gun (RG type, manufactured by Iwata Coating Machine Industry Co., Ltd.) at a rate equivalent to 10 liters / Are so that it would spread evenly over the whole crabgrass and the herbicidal effect. evaluated.

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

[0063]

[Equation 1]

Further, each pesticide composition was obtained in the same manner as above except that the following active ingredients 2 to 24 were used in place of the active ingredient 1, and the herbicidal efficacy of each of them was evaluated. Further, the herbicidal effect was evaluated in the same manner when only the pesticide was used (no addition). The results are shown in Table 1. Active ingredient 2; Active ingredient 1 / Emulgen 909 [POE (9) nonylphenyl ether] = 80/20 Active ingredient 3; Active ingredient 1 / Emulgen 103 [POE (3) C ₁₂ H
₂₅ OH] = 80/20 Active ingredient 4; Active ingredient 1 / Emanone 4110 [POE (10) C ₁₇
H ₃₅ COOH] = 80/20 Active ingredient 5; Active ingredient 1 / Leodol TWL-120 [POE (2
0) C ₁₁ H ₂₃ COO sorbitan ester] = 80/20 Active ingredient 6; A compound represented by the following formula was used.

[0065]

[Chemical 18]

Active ingredient 7; Active ingredient 6 / Emulgen 703
[Mixture of POE (3) C ₁₂ H ₂₅ OH and POE (3) C ₁₃ H ₂₇ OH] = 75/25 Active ingredient 8; Active ingredient 6 / Emanone 1112 [POE (12) C ₁₁
H ₂₃ COOH] = 75/25 Active ingredient 9; Active ingredient 6 / Leodol TWO-120 [POE (2
0) C ₁₇ H ₃₃ COO sorbitan ester] = 75/25 Active ingredient 10; Didecyldimethylammonium chloride Active ingredient 11; Monolauryltrimethylammonium chloride Active ingredient 12; Dilauryldihydroxyethylammonium chloride Active ingredient 13; Trimethylcocoammonium chloride Active ingredient 14: A compound represented by the following formula was used.

[0067]

[Chemical 19]

Active ingredient 15; Active ingredient 14 / Emulgen 909 = 80/20 Active ingredient 16; Active ingredient 14 / Emulgen 103 = 80/20 Active ingredient 17; Active ingredient 14 / Emanone 4110 = 80/20 Active ingredient 18; Effective ingredient Ingredient 14 / Leodol TWO-120 = 80/20 Active ingredient 19; A compound represented by the following formula was used.

[0069]

[Chemical 20]

Active ingredient 20; Active ingredient 19 / Emulgen 703 = 75/25 Active ingredient 21; Active ingredient 19 / Emanone 1112 = 75/25 Active ingredient 22; Active ingredient 19 / Leodol TWO-120 = 75/25 Active ingredient 23 A compound represented by the following formula was used.

[0071]

[Chemical 21]

Active ingredient 24; Active ingredient 23 / Reodol TWO-120 = 80/20 where POE is an abbreviation for polyoxyethylene, and the value in parentheses is the average number of moles of oxyethylene added. Further, a combination system of two kinds of compounds (active ingredients 2 to 5, 7 to 9,
The quantity ratio in 15-18, 20-22, 24) is a weight ratio.

[0073]

[Table 1]

Example 2 Adult female Kanzawa mites were superposed on a leaf disk of kidney beans in a group of 30 animals in 3 replicates, and then cultured at 24 hours and 25 ° C. After that, the entire leaf disk was immersed in the test solution for 5 seconds, taken out from the test solution and allowed to stand at 25 ° C. for 48 hours and then observed, and the acaricidal rate was determined based on the case of no treatment.
(See the formula below). Nissoran V emulsion as an acaricide (effective content 55% by weight, of which 50% by weight as hexithiazox,
For each of 5% by weight as DDVP) and 25% by weight of osadan wettable powder (25% by weight as fenbutatin oxide)
The same diluted solution as used in Example 1 was used as the agricultural chemical potency enhancer. It was prepared so that the concentration of the active ingredient of the agrochemical efficacy enhancer in the diluted solution was 0.1% by weight. The same was done when the efficacy enhancer was not used. The results are shown in Table 2.

[0075]

[Equation 2]

[0076]

[Table 2]

Example 3 A third-instar larva of a planthopper was cultured, and the efficacy of the insecticide was tested by the dipping method with 10 heads in 1 section and 3 systems. The insecticidal rate was calculated in the same manner as the acaricidal rate. 20 for each of the commercially available insecticide Sumithion Emulsion (50 wt% effective as MEP) and Marathon emulsion (50 wt% effective as marathon)
The 00-fold diluted solution was used, and the agrochemical efficacy enhancer used in Example 1 was used so that the concentration in the diluted solution was 0.1% by weight. The results are shown in Table 3.

[0078]

[Table 3]

Examples 1, 2, and 3 are tests in which the efficacy of the agrochemical potency enhancer of the present invention was compared with the case where a general cationic surfactant was used as an agrochemical potency enhancer (comparative product). Show. As is clear from Tables 1 to 3, the efficacy enhancer for agricultural chemicals of the present invention exerted a remarkable effect and was at a practical level, but in the comparative product, although some enhancement of the efficacy of the agricultural chemicals was observed, it was at a practical level. There was no effect to reach. Therefore,
It can be seen that the efficacy enhancer for agricultural chemicals of the present invention specifically enhances the efficacy of agricultural chemicals as compared with general cationic surfactants.

Example 4 A round-up solution was used as a herbicide, and the active ingredients 1 and 14 of Example 1 were used as a potency enhancer, and these were used in the amounts shown in Table 4 to carry out. The same test as in Example 1 was performed. The results are shown in Table 4.

[0081]

[Table 4]

Example 5 A roundup solution was used as a herbicide, and the active ingredients 6 and 19 of Example 1 were used as a potency enhancer, and these were used in the amounts shown in Table 5 to carry out the test. The same test as in Example 1 was performed. The results are shown in Table 5.

[0083]

[Table 5]

Example 6 A roundup solution was used as a herbicide, and the active ingredients 2 and 15 of Example 1 were used as a potency enhancer, and these were used in the amounts shown in Table 6 to carry out the test. The same test as in Example 1 was performed. The results are shown in Table 6.

[0085]

[Table 6]

Example 7 Sumitone emulsion was used as the insecticide, and active ingredient 1 and active ingredient 14 of Example 1 were used as the potency enhancer, and these were used in the amounts shown in Table 7. The same test as 3 was performed. The results are shown in Table 7.

[0087]

[Table 7]

Example 8 Osadan wettable powder was used as an acaricide, and the active ingredients 5 and 18 of Example 1 were used as efficacy enhancers, and these were used in the amounts shown in Table 8, The same test as in Example 2 was performed. The results are shown in Table 8.

[0089]

[Table 8]

Example 9 Using an osadane wettable powder as an acaricide, the active ingredients 7 and 20 of Example 1 were used as the potency enhancers, and these were used in the amounts shown in Table 9, The same test as in Example 2 was performed. The results are shown in Table 9.

[0091]

[Table 9]

Example 10 A roundup solution was used as a herbicide, and the active ingredients 23 and 24 of Example 1 were used as a potency enhancer, and these were used in the amounts shown in Table 10. The same test as in Example 1 was performed. The results are shown in Table 10.

[0093]

[Table 10]

Example 11 Osadan wettable powder was used as an acaricide, and active ingredients 23 and 24 of Example 1 were used as efficacy enhancers, and these were used in the amounts shown in Table 11, The same test as in Example 2 was performed. The results are shown in Table 11.

[0095]

[Table 11]

Production Example 2 250 g of N-methyloctadecylamine was placed in an autoclave equipped with a stirrer, a thermometer, a pressure gauge and a pressure-resistant dropping funnel, and the temperature was raised to 160 ° C. At a pressure of 0 to 6 kg / cm ² G, 45 g of ethylene oxide was added dropwise at any time. It took 3 hours to complete the dropping. Then, it was aged at 160 ° C. for 2 hours and cooled. The reaction product was taken out and distilled. 250 g N
-(2-Hydroxyethyl) -N-methyloctadecylamine was obtained. The boiling point was 185-190 ° C / 0.2 mmHg. 200 g of N- (2-hydroxyethyl) -N-methyloctadecylamine and 174 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube. 18
The temperature was raised to 0 ° C., and heating was performed at that temperature for 12 hours while distilling off the produced water. 350 g of N- (2-octadecanoyloxyethyl) -N-methyloctadecylamine was obtained. The following structure was confirmed from the NMR spectrum and IR spectrum. Hereinafter, this compound is referred to as active ingredient 25.

[0097]

[Chemical formula 22]

Example 12 The active ingredient 25 obtained in Preparation Example 2 was dissolved in deionized water so as to obtain a 0.2% by weight diluted solution. Using the obtained 0.2 wt% diluted solution, a commercially available herbicide, Roundup liquid (41 wt% effective), Carmex wettable powder (78.5 effective)
% By weight) and Herbiace water solvent (effective content 20% by weight) were diluted 300 times to obtain 3 kinds of pesticide compositions of the present invention. Using these pesticide compositions, the herbicidal effect was evaluated in the same manner as in Example 1. In addition, instead of the active ingredient 25, the following active ingredients 26 to 46 were each used in the same manner as above to obtain each pesticide composition, and the herbicidal efficacy was evaluated for each of them. Further, the herbicidal effect was evaluated in the same manner when only the pesticide was used (no addition). Results are in Table 12
It was shown to. Active ingredient 26; Active ingredient 25 / Emulgen 909 [POE (9) nonylphenol ether] = 80/20 Active ingredient 27; Active ingredient 25 / Emulgen 103 [POE (3) C ₁₂ H
₂₅ OH] = 80/20 Active ingredient 28; Active ingredient 25 / Emanone 4110 [POE (10) C
₁₇ H ₃₅ COOH] = 80/20 Active ingredient 29; Active ingredient 25 / Leodol TWL-120 [POE (2
0) C ₁₁ H ₂₃ COO sorbitan ester] = 80/20 active ingredient 30; a compound represented by the following formula was used.

[0099]

[Chemical formula 23]

Active ingredient 31; Active ingredient 30 / Emulgen 703
[Mixture of POE (3) C ₁₂ H ₂₅ OH and POE (3) C ₁₃ H ₂₇ OH] = 75/25 Active ingredient 32; Active ingredient 30 / Emanone 1112 [POE (12) C ₁₁
H ₂₃ COOH] = 75/25 Active ingredient 33; Active ingredient 30 / Leodol TWO-120 [POE (2
0) C ₁₇ H ₃₃ COO sorbitan ester] = 75/25 Active ingredient 34; Didecyldimethylammonium chloride Active ingredient 35; Monolauryltrimethylammonium chloride Active ingredient 36; Dilauryldihydroxyethylammonium chloride Active ingredient 37; Trimethyl coconut ammonium chloride Active ingredient 38: A compound represented by the following formula was used.

[0101]

[Chemical formula 24]

Active ingredient 39; Active ingredient 38 / Emulgen 909 = 80/20 Active ingredient 40; Active ingredient 38 / Emulgen 103 = 80/20 Active ingredient 41; Active ingredient 38 / Emanone 4110 = 80/20 Active ingredient 42; Effective Ingredient 38 / Reodol TWO-120 = 80/20 Active ingredient 43; a compound represented by the following formula was used.

[0103]

[Chemical 25]

Active ingredient 44; Active ingredient 43 / Emulgen 703 = 75/25 Active ingredient 45; Active ingredient 43 / Emanone 1112 = 75/25 Active ingredient 46; Active ingredient 43 / Leodol TWO-120 = 75/25 where: POE is an abbreviation for polyoxyethylene, and the value in () is the average number of moles of oxyethylene added. In addition, a combination system of two kinds of compounds (active ingredients 26 to 29, 31 to 33,
The quantity ratios in 39-42, 44-46) are weight ratios.

[0105]

[Table 12]

Example 13 The acaricidal rate was evaluated in the same manner as in Example 2 except that the one used in Example 12 was used as the agricultural chemical potency enhancer. The results are shown in Table 13.

[0107]

[Table 13]

Example 14 The insecticidal rate was evaluated in the same manner as in Example 3 except that the one used in Example 12 was used as the efficacy enhancer for agricultural chemicals. Show the result
Shown in 14.

[0109]

[Table 14]

Examples 12, 13, and 14 are tests in which the efficacy of the agrochemical potency enhancer of the present invention was compared with the case of using a general cationic surfactant as an agrochemical potency enhancer (comparative product). Show. As is clear from Tables 12 to 14, the efficacy enhancer for agricultural chemicals of the present invention exerted a remarkable effect and was at a practical level, but in the comparative product, although some enhancement of the efficacy of the agricultural chemicals was observed, it was at a practical level. There was no effect to reach. Therefore,
It can be seen that the efficacy enhancer for agricultural chemicals of the present invention specifically enhances the efficacy of agricultural chemicals as compared with general cationic surfactants.

Example 15 A roundup solution was used as a herbicide, and the active ingredients 25 and 38 of Example 12 were used as a potency enhancer, and these were used in the amounts shown in Table 15 to carry out the test. The same test as in Example 12 was conducted. The results are shown in Table 15.

[0112]

[Table 15]

Example 16 A round-up solution was used as a herbicide, and the active ingredients 30 and 43 of Example 12 were used as a potency enhancer, and these were used in the amounts shown in Table 16 to carry out the test. The same test as in Example 12 was conducted. The results are shown in Table 16.

[0114]

[Table 16]

Example 17 A roundup solution was used as a herbicide, and the active ingredients 26 and 39 of Example 12 were used as a potency enhancer, and these were used in the amounts shown in Table 17 to carry out the test. The same test as in Example 12 was conducted. The results are shown in Table 17.

[0116]

[Table 17]

Example 18 Sumition emulsion was used as the insecticide, and active ingredient 25 and active ingredient 38 of Example 12 were used as the efficacy enhancer, and these were used in the amounts shown in Table 18. The same test as 14 was conducted. The results are shown in Table 18.

[0118]

[Table 18]

Example 19 Using active ingredient 29 and active ingredient 42 of Example 12 as a potency enhancer, using osadan wettable powder as an acaricide, and using them in the amounts shown in Table 19, The same test as in Example 13 was performed. The results are shown in Table 19.

[0120]

[Table 19]

Example 20 Using osadan wettable powder as an acaricide, the active ingredients 31 and 44 of Example 12 were used as efficacy enhancers, and these were used in the amounts shown in Table 20. The same test as in Example 13 was performed. The results are shown in Table 20.

[0122]

[Table 20]

Production Example 3 A method known from the adduct of N-methylethanolamine and acrylonitrile [J. Org. Chem., 26 , 3409, (1960)].
66 g of N- (2-hydroxyethyl) -N-methyl-1,3-propylenediamine synthesized in step 284 g of stearic acid
Was charged into a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. It was heated at that temperature for about 10 hours while distilling off the produced water. 300 g of the obtained product was dissolved in 60 g of isopropyl alcohol, charged into an autoclave equipped with a stirrer, a thermometer, and a pressure gauge, and 28 g of methyl chloride was injected under pressure. After reacting at 100 ° C. for about 8 hours, isopropyl alcohol was distilled off under reduced pressure to obtain 320 g of a target compound represented by the following structural formula (1). The following structures were confirmed from NMR and IR spectra. Hereinafter, this compound is referred to as an active ingredient 47.

[0124]

[Chemical formula 26]

Example 21 The active ingredient 47 obtained in Production Example 3 was dissolved in deionized water so as to obtain a 0.2% by weight diluted solution. Using the obtained 0.2 wt% diluted solution, a commercially available herbicide, Roundup liquid (41 wt% effective), Carmex wettable powder (78.5 effective)
% By weight) and Herbiace water solvent (effective content 20% by weight) were diluted 300 times to obtain 3 kinds of pesticide compositions of the present invention. Using these pesticide compositions, the herbicidal effect was evaluated in the same manner as in Example 1. Further, each agrochemical compositions were obtained in the same manner as above except that the following active ingredients 48 to 74 were used instead of the active ingredient 47, and the herbicidal efficacy of these was evaluated. Further, the herbicidal effect was evaluated in the same manner when only the pesticide was used (no addition). Results are in Table 21
It was shown to. Active ingredient 48; Active ingredient 47 / Emulgen 909 [POE (9) nonylphenol ether] = 80/20 Active ingredient 49; Active ingredient 47 / Emulgen 103 [POE (3) C ₁₂ H
₂₅ OH] = 80/20 Active ingredient 50; Active ingredient 47 / Emanone 4110 [POE (10) C ₁₇
H ₃₅ COOH] = 80/20 Active ingredient 51; Active ingredient 47 / Leodol TWL-120 [POE (2
0) C ₁₁ H ₂₃ COO sorbitan ester] = 80/20 active ingredient 52; a compound represented by the following formula was used.

[0126]

[Chemical 27]

Active ingredient 53; Active ingredient 52 / Emulgen 703
[Mixture of POE (3) C ₁₂ H ₂₅ OH and POE (3) C ₁₃ H ₂₇ OH] = 75/25 Active ingredient 54; Active ingredient 52 / Emanone 1112 [POE (12) C ₁₁
H ₂₃ COOH] = 75/25 Active ingredient 55; Active ingredient 52 / Leodol TWO-120 [POE (2
0) C ₁₇ H ₃₃ COO sorbitan ester] = 75/25 Active ingredient 56; Didecyldimethylammonium chloride Active ingredient 57; Monolauryltrimethylammonium chloride Active ingredient 58; Dilauryldihydroxyethylammonium chloride Active ingredient 59; Trimethylcoco ammonium chloride Active ingredient 60: A compound represented by the following formula was used.

[0128]

[Chemical 28]

Active ingredient 61; Active ingredient 60 / Emulgen 909 = 80/20 Active ingredient 62; Active ingredient 60 / Emulgen 103 = 80/20 Active ingredient 63; Active ingredient 60 / Emanone 4110 = 80/20 Active ingredient 64; Effective Ingredient 60 / Leodoll TWO-120 = 80/2
0 active ingredient 65; a compound represented by the following formula was used.

[0130]

[Chemical 29]

Active ingredient 66; Active ingredient 65 / Emulgen 703 = 75/25 Active ingredient 67; Active ingredient 65 / Emanone 1112 = 75/25 Active ingredient 68; Active ingredient 65 / Leodol TWO-120 = 75/25 Active ingredient 69 A compound represented by the following formula was used.

[0132]

[Chemical 30]

Active ingredient 70; Active ingredient 69 / Emulgen 707
[POE (7) secondary C ₁₂ , C ₁₃ ether] = 75/25 Active ingredient 71; Active ingredient 69 / Rheidol TWO-120 = 75/25 Active ingredient 72; The compound represented by the following formula was used.

[0134]

[Chemical 31]

Active Ingredient 73; Active Ingredient 72 / Emulgen 909 = 80/20 Active Ingredient 74; Active Ingredient 72 / Reodol TWO-120 = 80/20 Where POE is an abbreviation for polyoxyethylene, and in () The numerical value is the average number of moles of oxyethylene added. In addition, a combination system of two compounds (active ingredients 48 to 51, 53 to 55,
The quantity ratio in 61-64, 66-68, 70, 71, 73, 74) is a weight ratio.

[0136]

[Table 21]

Example 22 The acaricidal rate was evaluated in the same manner as in Example 2 except that the one used in Example 21 was used as the agrochemical efficacy enhancer. The results are shown in Table 22.

[0138]

[Table 22]

Example 23 The insecticidal rate was evaluated in the same manner as in Example 3 except that the one used in Example 21 was used as the agricultural chemical potency enhancer. The results are shown in Table 23.
Shown in.

[0140]

[Table 23]

Examples 21, 22, and 23 are tests in which the efficacy of the potency-enhancing agent for agricultural chemicals of the present invention was compared with the case where a general cationic surfactant was used as the potency-enhancing agent for agricultural chemicals (comparative product). Show. As is clear from Tables 21 to 23, the pesticidal efficacy enhancer of the present invention exerted a remarkable effect and was at a practical level, but in the comparative product, although a slight enhancement of pesticide efficacy was observed, it was at a practical level. There was no effect to reach. Therefore,
It can be seen that the efficacy enhancer for agricultural chemicals of the present invention specifically enhances the efficacy of agricultural chemicals as compared with general cationic surfactants.

Example 24 A round-up solution was used as a herbicide, and the active ingredients 47 and 60 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 24. The same test as in Example 21 was conducted. The results are shown in Table 24.

[0143]

[Table 24]

Example 25 A round-up solution was used as a herbicide, and the active ingredients 52 and 65 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 25. The same test as in Example 21 was conducted. The results are shown in Table 25.

[0145]

[Table 25]

Example 26 A round-up solution was used as a herbicide, and the active ingredients 48 and 61 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 26. The same test as in Example 21 was conducted. The results are shown in Table 26.

[0147]

[Table 26]

Example 27 Sumition emulsion was used as the insecticide, and active ingredient 47 and active ingredient 60 of Example 21 were used as the efficacy enhancer, and these were used in the amounts shown in Table 27. The same test as 23 was conducted. The results are shown in Table 27.

[0149]

[Table 27]

Example 28 Using active ingredient 51 and active ingredient 64 of Example 21 as an efficacy enhancer using osadan wettable powder as an acaricide, and using these in the amounts shown in Table 28, The same test as in Example 22 was performed. The results are shown in Table 28.

[0151]

[Table 28]

Example 29 Using Osadan wettable powder as an acaricide, the active ingredients 53 and 66 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 29. The same test as in Example 22 was performed. The results are shown in Table 29.

[0153]

[Table 29]

Example 30 A round-up solution was used as a herbicide, and the active ingredient 69 and the active ingredient 70 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 30. The same test as in Example 21 was conducted. The results are shown in Table 30.

[0155]

[Table 30]

Example 31 A round-up solution was used as a herbicide, and the active ingredients 72 and 73 of Example 21 were used as a potency enhancer, and these were used in the amounts shown in Table 31. The same test as in Example 21 was conducted. The results are shown in Table 31.

[0157]

[Table 31]

Example 32 Using Osadan wettable powder as an acaricide, the active ingredient 69 and the active ingredient 70 of Example 21 were used as the efficacy enhancer, and these were used in the amounts shown in Table 32. The same test as in Example 22 was performed. The results are shown in Table 32.

[0159]

[Table 32]

Example 33 Using an osadane wettable powder as an acaricide, the active ingredients 72 and 73 of Example 21 were used as the efficacy enhancer, and these were used in the amounts shown in Table 33. The same test as in Example 32 was performed. The results are shown in Table 33.

[0161]

[Table 33]

Example 34 Sumitone emulsion was used as the insecticide, and the active ingredient 69 and the active ingredient 71 of Example 21 were used as the efficacy enhancer, and these were used in the amounts shown in Table 34. The same test as 23 was conducted. The results are shown in Table 34.

[0163]

[Table 34]

Example 35 Sumition emulsion was used as the insecticide, and active ingredient 72 and active ingredient 73 of Example 21 were used as the efficacy enhancer, and these were used in the amounts shown in Table 35. The same test as 23 was conducted. The results are shown in Table 35.

[0165]

[Table 35]

Example 36 Cucumber Botrytis cinerea (Botrytis), a fungicide-resistant bacterium
cinerea) spore suspension (10 ⁷ / ml) was sprinkled on cucumber seedlings (developing 3 true leaves) 10 ml per pot, 25
It was allowed to stand for 1 day at 90 ° C and 90% relative humidity.

Thereafter, a commercially available fungicide, Benlate wettable powder (50% by weight of active ingredient as benomyl) was added as an active ingredient (Table 36).
After diluting 2000 times with the 2500 times diluted solution of the reference), 5 ml was sprayed per pot. After that, 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 Table 36.

[0168]

[Equation 3]

[0169]

[Table 36]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 25/30 9159-4H // (A01N 37/20 47:30) (A01N 37/20 47: 38) (A01N 37/20 55:04) (A01N 37/20 57:12) (A01N 37/20 57:14) (A01N 37/20 57:20) (72) Inventor Toru Kato 1450 Nishihama, Wakayama ( 72) Inventor, Uichiro Nishimoto, 173-5, Otani, Wakayama City (72) Inventor, Yoshifumi Nishimoto, 1282-4 Hifata, Hainan City, Wakayama Prefecture (72) Inventor, Koshiro Sotoya 446-26, Nakaguro, Iwade-cho, Naga-gun, Wakayama Prefecture

Claims (11)

[Claims] 1. A pesticide efficacy enhancer comprising a compound represented by the general formula (I) as an active ingredient. [Chemical 1] [Chemical 2] R ^{1 to} R ³ : the same or different C ^{4 to} C 30 alkyl or alkenyl group X ⁻ : counter ion. However, one of B, C and D is -CH ₂
COO ^- or _{-CH 2 CH (OH) CH 2} SO 3 - may represent either, X
^- it does not exist. Represents ] 2. A pesticidal efficacy enhancer comprising a compound represented by the general formula (II) as an active ingredient. [Chemical 3] [Wherein Y and Z are the same or different and are an alkyl group or an alkenyl group having 6 to 30 carbon atoms; -C ₃ H ^₆ OR ₆ or _{-CH 2 CH (OH) CH 2} OR 6 ( wherein, R ^5; -H,
-CH _3, or mixtures thereof, R ^6; alkyl or alkenyl group of carbon number 5~29, n = 2~9, m = 2~9, p = 0~3
However, Y and Z cannot be an alkyl group or an alkenyl group having 6 to 30 carbon atoms at the same time. [Chemical 5] X ^-: represents a counter ion. ] 3. A pesticidal efficacy enhancer comprising a compound represented by the general formula (III) as an active ingredient. [Chemical 6] [Chemical 7] 4. At least one of the compounds represented by the general formulas (I) to (III) and one of surfactants other than the compound.
A pesticidal efficacy enhancer composition comprising at least one species as an active ingredient. 5. The agrochemical potency enhancer composition according to claim 4, wherein the surfactant is a nonionic surfactant. 6. The weight ratio of the total amount of the compounds represented by the general formulas (I) to (III) to the surfactant other than the compounds is [general formulas (I) to (III)]. Total amount of compound represented by
/ [Surfactant other than the compound] = 1/10 to 50/1, The pesticidal efficacy enhancer composition according to claim 4 or 5. 7. A pesticidal potency enhancer according to any one of claims 1 to 6 and a pesticidal ingredient, wherein the weight ratio of the pesticidal potency enhancer to the pesticidal ingredient is the pesticidal potency enhancer. Agricultural chemical composition wherein agent / agrochemical active substance = 0.05 to 50. 8. The pesticide composition according to claim 7, wherein the pesticide ingredient is selected from the active ingredients of fungicides, insecticides, acaricides, herbicides and plant growth regulators. 9. An agrochemical formulation comprising a packaged package of at least one of the compounds represented by the general formulas (I) to (III) and a packaged package of an agricultural chemical composition. 10. A packaged package of a composition comprising at least one of the compounds represented by the general formulas (I) to (III) and one or more surfactants other than the compound, and a pesticide composition. A pesticide formulation comprising a package. 11. A packaged package of at least one of the compounds represented by the general formulas (I) to (III), a packaged package of one or more surfactants other than the compound, and an agrochemical composition. Pesticide formulation consisting of a separate package of