WO1995017817A1 - Enhancer composition for agricultural chemicals and agricultural chemical composition - Google Patents
Enhancer composition for agricultural chemicals and agricultural chemical composition Download PDFInfo
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- WO1995017817A1 WO1995017817A1 PCT/JP1994/002263 JP9402263W WO9517817A1 WO 1995017817 A1 WO1995017817 A1 WO 1995017817A1 JP 9402263 W JP9402263 W JP 9402263W WO 9517817 A1 WO9517817 A1 WO 9517817A1
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- agricultural chemical
- agricultural chemicals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/04—Dandruff
Definitions
- the present invention relates to an enhancer composition for agricultural chemicals, an agricultural chemical composition, a method for enhancing the effectiveness of an agricultural chemical, a use of the above-mentioned enhancer composition for agricultural chemicals for the preparation of an agricultural chemical composition, a use of the above-mentioned enhancer composition for agricultural chemicals for enhancing the effectiveness of an agricultural chemical and an agricultural chemical kit.
- Agricultural chemicals including insecticides, fungicides (or bactericides) , herbicides, miticides (or acaricides) and plant growth regulators have been used in the forms of, for example, emulsions, wettable powders, granules, powders and flowables.
- emulsions emulsions
- wettable powders emulsions
- miticides emulsions
- granules e.g., granules, powders and flowables.
- plant growth regulators emulsions, wettable powders, granules, powders and flowables.
- surfactants comprising various nitrogen-containing compounds such as quaternary ammonium salts, betaines and amine oxides have been known (see European Patent Publication-A No. 274369, published on July 13, 1988). It is known that quaternized or further polyoxyethylenated long-chain amines, among the above- mentioned compounds, are effective for this purpose. However, the enhancement effect of the above described compounds capable of enhancing the effectiveness of agricultural chemicals is not always satisfied.
- European Patent Publication-A No. 36106 (published on September 23, 1981) has disclosed a herbicide composition comprising a phosphinothricin derivative, a specific quaternary ammonium salt and a chelating agent.
- a herbicide composition comprising a phosphinothricin derivative, a specific quaternary ammonium salt and a chelating agent.
- particular examples of the quaternary ammonium salts disclosed in this patent include ammonium sulfate, ammonium nitrate, ammonium acetate and the like, and do not include organic quaternary ammonium salts generally used as cationic surfactants.
- the present inventors From a standpoint that the efficacy of an agricultural chemical can be enhanced by using the agricultural chemical together with at least one nitrogen-containing compound selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt, the present inventors have conducted extensive studies. As a result, they have found that the efficacies of various agricultural chemicals can be remarkably enhanced by adding a nitrogen-containing compound together with a chelating agent thereto. The present invention has been completed on the basis of this finding.
- the present invention provides an enhancer composition for agricultural chemicals comprising at least one nitrogen-containing compound selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent, wherein the content of the chelating agent ranges from 0.01 to 30 mol per mol of the nitrogen-containing compound.
- the nitrogen-containing compound is preferably a nitrogen-containing surfactant selected from the group consisting of an organic tertiary amine, an organic tertiary amine salt and an organic quaternary ammonium salt.
- the present invention provides an agricultural chemical composition
- an agricultural chemical composition comprising an agricultural chemical, at least one nitrogen- containing compound selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent, wherein the content of the chelating agent ranges from 0.01 to 30 mol per mol of the nitrogen-containing compound and the weight ratio of the total of the nitrogen-containing compound and the chelating agent to the agricultural chemical ranges from 0.05 to 50.
- the present invention provides a method for enhancing the effectiveness of an agricultural chemical which comprises applying the above-mentioned enhancer composition for agricultural chemicals with an agricultural chemical to a locus which would be benefit from such treatment, a use of the above-mentioned enhancer composition for agricultural chemicals for the preparation of an agricultural chemical composition, and a use of the above-mentioned enhancer composition for agricultural chemicals for enhancing the effectiveness of an agricultural chemical.
- the present invention provides an agricultural chemical kit which comprises a container containing the above-mentioned enhancer composition for agricultural chemicals and a container containing an agricultural chemical composition, an agricultural chemical kit which comprises a container containing the above-mentioned enhancer composition for agricultural chemicals, a container containing a surfactant other than the above nitrogen-containing compounds and a container containing an agricultural chemical composition, an agricultural chemical kit which comprises a container containing the above-mentioned enhancer composition for agricultural chemicals, a container containing an adjuvant for penetration of agricultural chemicals and a container containing an agricultural chemical composition, and an agricultural chemical kit which comprises a container containing the above-mentioned enhancer composition for agricultural chemicals, a container containing a surfactant other than the above nitrogen-containing compounds, a container containing an adjuvant for penetration of agricultural chemicals and a container containing an agricultural chemical composition.
- agricultural chemical means one which is employed as an active or principle ingredient in common agricultural chemical compositions or preparations, and examples thereof include a fungicide (or a bactericide) , an insecticide, a miticide (or an acaricide) , a herbicide, a plant growth regulator and the like.
- R* represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms
- each A represents an alkylene group, preferably an alkylene group having 2 to 4 carbon atoms
- n and m each represents such a number that the sum of n and m, i.e., the average oxyalkylene number per molecule, is 1 to 40, generally an integer
- R 2 and R 3 are the same or different from each other and each represents a hydrogen atom or an acyl group (for example, formyl group, acetyl group, propionyl group or benzoyl group).
- R 1 and R 2 are the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group, preferably an alkyl group having 1 to 4 carbon atoms;
- R 3 and R 4 are the same or different from each other and each represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group;
- each R 5 represents a hydrogen atom or a methyl group;
- each R 6 represents a hydrogen atom or a methyl group;
- m and n are the same or different from each other and each represents a positive number of 1 to 5; and
- p and q which generally each represents an average value, are either the same or different from each other and each represents a number of 0 to 30.
- R 1 represents an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group
- R 2 represents a linear or branched alkyl group having 1 to 36 carbon atoms which may be substituted by a hydroxyl group or a linear or branched alkenyl group having 2 to 36 carbon atoms which may be substituted by a hydroxyl group, preferably a linear or branched alkyl or alkenyl group having 5 to 36 carbon atoms which may be substituted by a hydroxyl group, a group represented by the formula: -C n H 2 seemingly-(G 1 )-R 4 (wherein R 4 represents a linear or branched alkyl or alkenyl group having 5 to 36 carbon atoms which may be substituted by a hydroxyl group; G 1 represents a group represented by the formula: -0C0- or a group represented by the formula: -NHCO-; and n represents a positive number of 2 to 6), a group represented by
- R 0 represents a linear or branched alkyl or alkenyl group having
- each R 6 represents a hydrogen atom or a methyl group
- m is a positive number of
- R 7 represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 8 represents a hydrogen atom or a methyl group; G 2 represents a group represented by the formula:
- R 3 represents a group represented by the formula:
- R 9 represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 10 represents a hydrogen atom or a methyl group; G 3 represents a group represented by the formula: -0C0- or a group represented by the formula: -NHCO-; s represents a positive number of 2 to 6; t represents a positive number of 1 to 5; and h, which generally represents an average value, represents a positive number of 0 to 30) or a group represented by the formula:
- R n ii represents a linear or branched alkyl or alkenyl group having 6 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 12 represents a hydrogen atom or a methyl group; j represents a positive number of 1 to 5; and r, which generally represents an average value, represents a positive number of 0 to 30).
- tertiary amine salt to be used in the present invention examples include salts of the above- mentioned organic tertiary amines, for example, inorganic salts thereof such as hydrochlorides, sulfates and nitrates thereof, and organic salts thereof such as carboxylates and sulfonates thereof.
- examples of the quaternary ammonium salt to be used in the present invention include those which will be described below.
- each A represents an alkylene group having 2 or 3 carbon atoms
- R 1 and R 2 are either the same or different from each other and each represents an alkyl group having 1 to 5 carbon atoms
- R 3 represents an alkyl group having 1 to 5 carbon atoms or a group represented by the formula: (AO),—H
- i when R 3 is an alkyl group
- j when R 3 is a group represented by the formula: (AO),—H) , which represents the average oxyalkylene number per molecule, is a number of 2 to 20
- X " is an appropriate counter anion.
- EO represents an oxyethylene group
- PO represents an oxypropylene group
- R 1 and R 2 are either the same or different from each other and each represents an alkyl group having 1 to 3 carbon atoms
- R 3 represents an alkyl group having 1 to 3 carbon atoms or a group represented by the formula: EO-(PO ⁇ -H; either n (when R 3 is an alkyl group) or the sum of n and m (when R 3 is a group represented by the formula: EO-fPO jj -H) , which represents the average oxypropylene number per molecule, is a number of 2 to 20
- X " is an appropriate counter anion.
- R 1 , R 2 , R 3 and R 4 are either the same or different from one another and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyethyl group, or two among R 1 , R 2 , R 3 and R 4 form a 3- to 7-membered ring together with the nitrogen atom bonded thereto and -0-, -NH- or -NR- (wherein R represents an alkyl group having 1 to 4 carbon atoms) may substitute for one -CH 2 - group constituting said 3- to 7-membered ring; X " represents an anion of inorganic or organic, monobasic or polybasic acid; and n represents 1, 2 or 3 depending on the valence of X " . (6) Quaternary ammonium salts represented by the following formula (6):
- R j represents a linear or branched alkyl or alkenyl group having 20 to 40 carbon atoms, an alkyl(or alkenyl)arylpolyoxyalkylene, alkyl(or alkenyl)polyoxyethylene or alkyl(or alkenyl)- polyoxypropylene group having a linear or branched alkyl or alkenyl group having 20 to 40 carbon atoms, or an acylaminoalkyl or acyloxy- alkyl group having a linear or branched acyl group having 20 to 40 carbon atoms;
- R 2 and R 3 are either the same or different from each other and each represents a group represented by the
- R ⁇ represents an alkyl or alkenyl group having 12 to 30 carbon atoms, an alkylpolyoxyalkylene, alkyl- arylpolyoxyalkylene, alkylpolyoxyethylene or alkylpolyoxypropylene group having an alkyl group having 12 to 30 carbon atoms, or an acylamino- alkyl or acyloxyalkyl group having an acyl group having 12 to 30 carbon atoms; and X " represents a counter anion selected from the group consisting of a halide ion, a phosphate group having an alkyl moiety with 1 to 10 carbon atoms, a sulfate group having an alkyl moiety with 1 to 10 carbon atoms and a carboxyl group having an alkyl moiety with 1 to 10 carbon atoms. (7) Quaternary ammonium salts represented by the following formula (7)
- R j , R 2 and R 3 is a linear or branched alkyl or alkenyl group having 8 to 30 carbon atoms while the other(s) each represents a methyl group, an ethyl group, a benzyl group, a
- R 4 represents a methyl group or an ethyl group
- X " which represents a counter ion, is an anionic oligomer or polymer having an average molecular weight of 300 to 20,000 and having an acid type anionic residue, for example, a naphthalene sulfonic acid/formaldehyde condensate.
- R 7 and R 8 are either the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms
- R 9 represents a hydrogen atom, a benzyl group or an alkyl group having 1 to 4 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms
- R 10 and R 11 are either the same or different from each other and each represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group
- each R 12 represents a hydrogen atom or a methyl group
- each R 13 represents a hydrogen atom or a methyl group
- j and k are either the same or different from each other and each represents a positive number of 1 to 5
- r and s, which generally each represents an average value, are either the same or different from each other and each represents a number of 0 to 30
- X " is a counter ion.
- R represents a hydrogen atom, a benzyl group or an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group, preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group
- R 1 represents an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group
- R 2 represents a linear or branched alkyl group having 1 to 36 carbon atoms which may be substituted by a hydroxyl group or a linear or branched alkenyl group having 2 to 36 carbon atoms which may be substituted by a hydroxyl group, preferably a linear or branched alkyl or alkenyl group having 5 to 36 carbon atoms which may be substituted by a hydroxyl group, a group represented by the formula: -C n .-H 2n t-(G 1 )-R 4 (wherein R 4 ' represents a
- R 6 ' ii I 0 R 6 ' ii I ,, by the formula: -C B .H 2B >-C-(OCHCH 2 ) p .OR b (wherein R 5 represents a linear or branched alkyl or alkenyl group having 6 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 6 represents a hydrogen atom or a methyl group; m' is a positive number of 1 to 5; and p', which generally represents an average value, is a number of 0 to 30) or a group represented by the
- R 8 ' formula: -C ⁇ H ⁇ .-(G 2 ')-C k .H 2 .-(OCHCH 2 ) q .OR 7 ' (wherein
- R 7 represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 8 represents a hydrogen atom or a methyl group; G 2 represents a group represented by the formula:
- R 3 represents a group represented by the formmula:
- R 9 ' represents a linear or branched alkyl or alkenyl group having 4 to 36 carbon atoms which may be substituted by a hydroxyl group; each R 10 represents a hydrogen atom or a methyl group; G 3 represents a group represented by the formula: -0C0- or a group represented by the formula: -NHCO-; s' is a positive number of 2 to 6; t' is a positive number of 1 to 5; and h', which generally represents an average value, is a number of 0 to 30), or a group represented by the
- R 12 ' formula: -C j .H 2j .-C 11 -(0C'HCH 2 ) r .0R ⁇ ir (wherein R 11 represents a linear or branched alkyl or alkenyl group having 6 to 36 carbon atoms which may be substituted by a hydroxyl group; each R i2 represents a hydrogen atom or a methyl group; j' is a positive number of 1 to 5; and r', which generally represents an average value, is a number of 0 to 30); and X " is a counter ion.
- R 18 represents a hydrogen atom, a benzyl group or an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group, preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group
- R 19 represents an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxyl group
- R 20 represents a linear or branched alkyl or alkenyl group having 6 to 36 carbon atoms which may be substituted by a hydroxyl group
- R 21 represents a linear or branched alkyl or alkenyl group having 5 to 36 carbon atoms which may be substituted by a hydroxyl group
- d is a positive number of 1 to 5
- X " is a counter ion.
- R 1 and R 2 are either the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms, a group represented by the formula: - )
- ll -H wherein each R 7 represents a hydrogen atom or a methyl group; and ml, which generally represents an average value, is a number of 1 to 30
- each R ⁇ represents a hydrogen atom or a methyl group
- R 12 represents a linear or branched alkyl or alkenyl group having 5 to 36 carbon atoms which may be substituted by a hydroxyl group
- q2 which generally represents an average value, is a number of 0 to 30
- each R 5 represents a hydrogen atom or a methyl group
- R° represents a linear or branched alkyl or alkenyl group having 5 to 35 carbon atoms which may be substituted by a hydroxyl group
- n which generally represents an average value, is a number of .0 to 30
- X " is a counter ion.
- Quaternary ammonium salts represented by the above formula (11) includes, for example, those having an oxyalkylene group(s) and those represented by the following formula (11'):
- R 1 to R 3 are either the same or different from one another and each represents an alkyl or hydroxyalkyl group having 1 to 4 carbon atoms;
- R 4 represents a group represented by the formula: -OCOR (wherein R represents an alkyl or alkenyl group having 14 to 22 carbon atoms); R° represents an alkyl or alkenyl group having 14 to 22 carbon atoms; and
- X' " is a counter anion derived from a strong acid.
- R ⁇ and R 2 are either the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms or a group represented by the formula: R 5 -CH-CH 2 - (wherein R 5
- R 6 represents an alkyl or alkenyl group having 4 to
- Rg represents an alkyl or alkenyl group having 2 to 20 carbon atoms
- R ⁇ and R 2 represents a group represented by the formula: R 5 -CH-CH 2 - (wherein R 5 and R g each has the same meaning as the one defined above)
- R 3 and R ⁇ are either the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms
- X " is a counter anion.
- R R 2 , and R j represents an alkyl or alkenyl group having 8 to 30 carbon atoms while the other(s) each represents a methyl group, an ethyl group, a benzyl group, a group
- n which generally represents an average value, is a number of 1 to 15, preferably an integer of 1 to 15
- R4 represents a methyl group
- Quaternary ammonium salts represented by the formula (14) :
- R , R 2 and R 3 represents a linear or branched alkyl or alkenyl group having 8 to 30 carbon atoms while the other(s) each represents a methyl group, an ethyl group, a benzyl group, a group represented by the formula:
- each A represents an alkylene group, preferably an alkylene group having 2 to 4 carbon atoms; and x, which generally represents an average value, represents a number of 1 to 60, preferably an integer of 1 to 60) or a group represented by the formula: -CH 2 - (CH) 5 CH 2 OH; R 4
- OH represents a methyl group, an ethyl group or a group represented by the formula: -CH 2 CH 2 OH; and X " , which represents a counter anion, represents a halide ion, a phosphate group, a phosphonate group, a sulfonate group having a hydrocarbon moiety with at least 7 carbon atoms, a sulfate group having a hydrocarbon moiety with at least 7 carbon atoms or an anionic oligomer or copolymer having a degree of polymerization of at least 3 and having an anionic residue.
- Quaternary ammonium salts represented by the following formula (15) :
- R ⁇ and R 2 are either the same or different from each other and each represents a linear or branched alkyl or hydroxyalkyl group having 1 to 30 carbon atoms or a linear or branched alkenyl group having 2 to 30 carbon atoms ;
- a ⁇ O and A 2 0 each represents an oxyalkylene group having 2 to 4 carbon atoms;
- n and m each represents 0 or a positive number, preferably 0 or a positive integer, provided that the sum of n and m, which generally represents an average value, is a number of 1 to 100; and
- X " represents a counter ion.
- A represents a hydrogen atom, a group represented by the formula: -CH 2 CH 2 -CN, a group represented by the formula: -CH 2 CH 2 COOH, a group represented by the formula: -CHCOONa, a group
- R represented by the formula : -C n H 2n 0- ( CH 2 CHO ) B -C-R >2
- n is a number of 2 to 9; p, which generally represents an average value, is a number of 0 to 30; each R represents a hydrogen atom or a methyl group; and R 2 represents an alkyl or alkenyl group having 4 to 30 carbon atoms
- B, C and D are either the same or different from one another and each represents a hydrogen atom, a methyl group, an ethyl group, a group represented by the formula: -(CiHo.-O) JJ-C n-R 3 (wherein R 3
- 0 represents an alkyl or alkenyl group having 4 to 30 carbon atoms; i is a number of 2 to 6; and j, which generally represents an average value, is a number of 1 to 10), a group represented by the formula: -CH 2 C00H, a group represented by the formula: -(C ⁇ H 2i 0),--H (wherein i and j each has the same meaning as the one defined above) , a group represented by the formula: -CH 2 C00 " , a group represented by the formula: -CH 2 CH(OH)CH 2 S0 3 " or a benzyl group, provided that when one of B, C and D is a group represented by the formula: -CH 2 C00 " or a group represented by the formula: -CH 2 CH(OH)CH 2 S0 3 " , then the others are each a groups other than a group represented by the formula: -CH 2 COO " and a group represented by the formula: -CH 2 CH(OH)CH
- Y and Z are either the same or different from each other and each represents an alkyl or alkenyl group having 6 to 30 carbon atoms, a group represented by the formula:
- R 5 0 -C n H 2]1 0-(CH 2 C 1 HO) p -C"-Rfi t) (wherein each R b represents a hydrogen atom or a methyl group; R 6 represents an alkyl or alkenyl group having 5 to 29 carbon atoms; n is a number of 2 to 9; and p, which generally represents an average value, is a number of 0 to 30), a group represented by the formula -C 3 HgNHCOR 6 (wherein R 6 has the same meaning as the one defined above) , a group represented by the formula:
- R 6 has the same meaning as the one defined above, provided that Y and Z do not represent alkyl or alkenyl groups having 1 to 4 carbon atoms at the same time; R 4 represents an alkyl group having 1 to 4 carbon atoms or a
- R 7 and R 8 are either the same or different from each other and each represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or a group
- R 10 represents a hydrogen atom or a methyl group; and q, which generally represents an average value, is a number of 1 to 30);
- R 9 represents an alkyl group having 6 to 36 carbon atoms, a group represented by the formula:
- R 10 0 formula : -0- ( CH 2 CHO ) p -C r H 2r NHC-R n (wherein p , r , R 10 and R 11 each has the same meaning as the one defined above ) ; n is a number of 2 to 9 ; and X " is a counter ion .
- Examples thereof include halide ions such as Cl “ , Br “ and I “ , alkyl sulfate (RS0 4 " ) groups, alkylbenzene- sulfonate (R-benzene-S0 3 " ) groups, alkylnaphthalene- sulfonate (R-naphthalene-S0 3 ⁇ ) groups, fatty acid residues (RCOO “ ) , alkyl phosphate (R0P0 3 H “ , wherein R represents an alkyl group) groups, anionic oligomers and anionic polymers.
- halide ions such as Cl “ , Br “ and I "
- alkyl sulfate (RS0 4 " ) groups alkylbenzene- sulfonate (R-benzene-S0 3 " ) groups, alkylnaphthalene- sulfonate (R-naphthalene-S0 3 ⁇ ) groups, fatty acid residues
- compounds represented by the formulae (6), (7), (12), (13), (14) and (15) are preferably used, compounds represented by the formulae (16) , (17) and (18) are still more preferably used, and compounds represented by the formulae (2), (3), (8), (9), (10) and (11) are most preferably used.
- the chelating agent to be used in the present invention is not particularly restricted, so long as it is capable of chelating a metal ion.
- the chelating agent usable in the present invention include amino polycarboxylic acid chelating agents, aromatic or aliphatic carboxylic acid chelating agents, amino acid chelating agents, ether polycarboxylic acid chelating agents, phosphonic acid chelating agents such as iminodimethylphosphonic acid (IDP) and alkyldiphosphonic acid (ADPA) , hydroxy carboxylic acid chelating agents, electrolyte chelating agents of polymer (including oligomer) type, and dimethylglyoxi e (DG) .
- These chelating agents may be in the form of either an acid or a salt such as sodium salt, potassium salt and ammonium salt. Alternatively, these chelating agents may be in the form of an ester derivative thereof which can be hydrolyzed.
- aminopolycarboxylic acid chelating agents include a) compounds represented by the chemical formula of RNX 2 , b) compounds represented by the chemical formula of NX 3 , c) compounds represented by the chemical formula of R-NX-CH 2 CH 2 -NX-R, d) compounds represented by the chemical formula of R-NX-CH 2 CH 2 -NX 2 , e) compounds represented by the chemical formula of X 2 N-R'-NX 2 and f) compounds similar to compounds of e) and containing four or more Xs, for example, a compound represented by the formula: (HOOCH 2 C) 2 N-CH 2 CH 2 -N-CH 2 CH 2 -N(CH 2 COOH) 2 .
- X represents a group represented by the formula: -CH 2 COOH or a group represented by the formula: -CH 2 CH 2 COOH
- R represents a group to be contained in these type, known chelating agents such as a hydrogen atom, an alkyl group, a hydroxyl group and a hydroxyalkyl group
- R' represents a group to be contained in these type, known chelating agents such as an alkylene group and a cycloalkylene group.
- aminopoly ⁇ carboxylic acid chelating agents include ethylene- diaminetetraacetic acid (EDTA) , cyclohexanediamine- tetraacetic acid (CDTA) , nitrilotriacetic acid (NTA) , iminodiacetic acid (IDA), N-(2-hydroxyethyl)imino- diacetic acid (HIMDA) , diethylenetriaminepentaacetic acid (DTPA) , N-(2-hydroxyethyl)ethylenediamine- triacetic acid (EDTA-OH) and glycoletherdiamine- tetraacetic acid (GEDTA) , and salts thereof.
- EDTA ethylene- diaminetetraacetic acid
- CDTA cyclohexanediamine- tetraacetic acid
- NTA nitrilotriacetic acid
- IDA iminodiacetic acid
- HAMDA N-(2-hydroxyethyl)imino- diacetic acid
- aromatic or aliphatic carboxylic acid chelating agents to be used in the present invention include oxalic acid, succinic acid, pyruvic acid, salicylic acid and anthranilic acid, and salts, methyl esters and ethyl esters thereof.
- amino acid chelating agents to be used in the present invention include glycine, serine, alanine, lysine, cystine, cysteine, ethionine, tyrosine and methionine, and salts and derivatives thereof.
- examples of the ether polycarboxylic acid chelating agents to be used in the present invention include compounds represented by the following formula, compounds similar to the compounds represented by the following formula and salts (e.g., sodium salt) thereof:
- Y 1 represents a hydrogen atom, a group represented by the formula: -CHCOOH or a group represented by the formula: -COOH
- Z 1 represents a hydrogen atom, a group represented by the formula: -CH 2 COOH or a group represented by the formula: -CHCOOH.
- hydroxy carboxylic acid chelating agents examples include malic acid, citric acid, glycolic acid, gluconic acid, heptonic acid, tartaric acid, lactic acid and salts thereof.
- electrolyte chelating agents of polymer (including oligomer) type to be used in the present invention include acrylic acid polymers, maleic anhydride polymers, ⁇ -hydroxyacrylic acid polymers, itaconic acid polymers, copolymers comprising at least two of the constituting monomers of these polymers and epoxysuccinic acid polymers.
- chelating agents to be used in the present inveniton further include ascorbic acid and thioglycollic acid, and salts thereof.
- chelating agents include aliphatic carboxylic acid chelating agents, aromatic carboxylic acid chelating agents, hydroxy carboxylic acid chelating agents, amino acid chelating agents, ether polycarboxylic acid chelating agents, phosphonic acid chelating agents, electrolyte chelating agents of polymer (including oligomer) type, dimethylglyoxime (DG) , ascorbic acid and thioglycollic acid, and salts of ascorbic acid and thioglycollic acid.
- aliphatic carboxylic acid chelating agents, aromatic carboxylic acid chelating agents, hydroxy carboxylic acid chelating agents, amino acid chelating agents and ether polycarboxylic acid chelating agents are still more preferable.
- such a chelating agent is used in an amount of from 0.01 to 30 mol, preferably from 0.05 to 20 mol and still more preferably from 0.1 to 15 mol, per mol of the above-mentioned nitrogen-containing compound (the total content by mol, when two or more nitrogen- containing compounds are used).
- the enhancer composition for agricultural chemicals of the present invention comprises the above-mentioned nitrogen-containing compound (A) and the chelating agent (B) .
- this enhancer composition for agricultural chemicals can enhance the efficacy of the agricultural chemical twice to thrice without causing any phytotoxicity.
- the enhancer for agricu.1tural chemicals of the present invention can be safely applied to various crops without causing any phytotoxicity.
- the nitrogen-containing compounds employed in the present invention are those positively charged in water. Therefore, it specifically adheres to cell membranes of plants, microorganisms and insects, invades the membranes and then abnormally elevates the flowability of the cell membranes, thus causing a disturbance in the membrane functions. As a result, the amount of the agricultural chemical incorporated into the cells is increased and thus the efficacy of the agricultural chemical is enhanced. It is estimated that the chelating agent undergoes some interaction with the nitrogen-containing compound to thereby enhance the efficacy of the agricultural chemical.
- the effect of the chelating agent in the present invention essentially differs from the effect, which has hitherto been lectured, of a chelating agent of trapping trace metal ions in water and thus enhancing the efficacy of an agricultural chemical. It has been observed in practice that the effect of a nitrogen-containing compound according to the present invention in enhancing the efficacy of an agricultural chemical is strengthened by adding a chelating agent both in distilled water and in hard water.
- the dose of the above-mentioned nitrogen-containing compound (A) can be reduced while maintaining the enhancing effect thereof on an agricultural chemical by further using a surfactant (C) other than the nitrogen-containing compounds (A) and/or an adjuvant for penetration of agricultural chemicals (D) therewith.
- a surfactant (C) other than the nitrogen-containing compounds (A) and/or an adjuvant for penetration of agricultural chemicals (D) therewith.
- surfactant (C) other than the nitrogen-containing compounds examples include nonionic surfactants, anionic surfactants and amphoteric surfactants. These surfactants may be used either alone or as a mixture of two or more of them.
- nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkyl- aryl ethers, polyoxyethylene alkylaryl ether/ formaldehyde condensates, polyoxyalkylene aryl ethers, polyoxyalkylene alkyl esters, polyoxyalkylene alkylsorbitol esters, polyoxyalkylene sorbitan esters, polyoxyalkylene alkylglycerol esters, polyoxyalkylene block copolymers, polyoxyalkylene block copolymer/ alkylglycerol esters, polyoxyalkylene alkylsulfon- amides, polyoxyalkylene rosin esters, polyoxypropylene block copolymers, polyoxyethylene oleyl ethers, polyoxyalkylene alkylphenols, alkylglycosides, alkylpolyglycosides, polyoxyalkylene alkyl- polyglycosides, and mixtures comprising two or
- anionic surfactants typical ones are available in the form of an aqueous solution or a solid.
- anionic surfactants typical ones are available in the form of an aqueous solution or a solid.
- examples thereof include sodium mono- and di- alkylnaphthalenesulfonates, sodium ⁇ -olefinsulfonate, sodium alkanesulfonates, alkylsulfosuccinates, alkylsulfates, polyoxyalkylene alkyl ether sulfates, polyoxyalkylene alkyl aryl ether sulfates, polyoxy ⁇ alkylene styryl phenyl ether sulfates, mono- and dialkylbenzenesulfonates, alkylnaphthalenesulfonates, alkylnaphthalenesulfonate/formaldehyde condensates, alkyl diphenyl ether sulfonates, olefinic sulf
- ampholytic surfactants include lauryldimethylamine oxide, Armox C/12, amine oxides, Monaterics, Miranols, betaines, Lonzaines, other amine oxides and mixtures thereof.
- nonionic surfactants nonionic surfactants, anionic surfactants and mixtures of a nonionic surfactant and an anionic surfactants are preferable, and mixtures of a nonionic surfactant and an anionic surfactants are still more preferable.
- these mixtures those in which the weight ratio of the nonionic surfactant to the anionic surfactant ranges from 1/50 to 50/1 are desired, and those in which the weight ratio ranges from 1/30 to 15/1 are particularly desired.
- nonionic surfactants those of the ester type, such as polyoxyalkylene sorbitan esters and polyoxyalkylene alkyl glycerol esters, polyoxyalkylene alkyl ethers and polyoxyalkylene alkylphenyl ethers are preferred, and those of the ester type are particularly preferred from the point of view of environmental conservation, since they are excellent in biodegradability.
- anionic surfactants polyoxyalkylene alkyl ether sulfates, alkylbenzene- sulfonates, and linear and branched alkyl polyoxyalkylene ether acetic acids and salts thereof are preferred and polyoxyalkylene alkyl ether sulfates and linear and branched alkyl polyoxyalkylene ether acetic acids and salts thereof are particularly preferred.
- the weight ratio of the nitrogen-containing compound (A) to the surfactant (C) other than the nitrogen-containing compounds preferably ranges from 1/10 to 50/1, still more preferably from 1/1 to 10/1.
- the adjuvant for penetration of agricultural chemicals (D) is used for the efficient penetration of an agricultural chemical into insects, plants, fungi, etc. Examples thereof include those described below.
- Water including deionized water, aqueous solutions of organic or inorganic acids and aqueous solutions of alkalis.
- Monohydric alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, isoamyl alcohol, 3-pentanol, n-hexanol, n-heptanol, 2-heptanol, n-octanol, 2-ethylhexanol, n-decanol, undecanol, n-dodecanol, tetradecanol, heptadecanol, cyclohexanol and benzyl alcohol.
- Polyhydric alcohols and alcohol ethers such as ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monomethyl acetate, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol isopropyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol isoamyl ether, ethylene glycol monophenyl ether, ethylene glycol monophenyl ether acetate, ethylene glycol benzyl ether, ethylene glycol monohexyl ether, dimethoxyethanol, ethylene glycol monoacetate, ethylene glycol diacetate, diethylene glycol, 1,3- butylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol
- preferable ones are polyalkylene glycol monoalkyl ethers and polyalkylene glycol dialkyl ethers, and still more preferable ones are diethylene glycol monoalkyl(C ⁇ . ) ethers, diethylene glycol dialkyl(C ⁇ g) ethers, triethylene glycol monoalkyl(C ⁇ g) ethers and triethylene glycol dialkyl(C ) ethers.
- Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane , dichloroethane , trichlorofluoromethane and dichlorodifluoromethane .
- Ethers such as diethyl ether, diisopropyl ether, dibutyl ether, dihexyl ether, diisoamyl ether, methyl phenyl ether, ethyl phenyl ether, amyl phenyl ether, ethyl benzyl ether, 1,4-dioxane, tetrahydrofuran, tetrahydropyran and polyoxyalkylene phenyl ethers.
- preferable ones are polyoxyalkylene phenyl ethers
- still more preferable ones are polyoxyethylene phenyl ethers wherein the number of oxyethylene groups per molecule is from 1 to 10.
- Ketones such as acetone, methylacetone , methyl ethyl ketone, methyl n-butyl ketone, methyl isobutyl ketone, methyl n-hexyl ketone, diethyl ketone, acetone oil, acetonylacetone, phorone , isophorone, cyclo- hexanone , methylcyclohexanone and pyrrolidone.
- Esters such as methyl acetate, ethyl acetate, n-butyl acetate, n-amyl acetate, isoamyl acetate, methylisoamyl acetate, methyl prop onate, isoamyl propionate, n-butyl butyrate, butyl stearate, amyl stearate, 2-ethylhexyl oleate, lauryl oleate, oleyl oleate, methyl lactate, ethyl lactate, ethyl benzoate, propyl benzoate, isoamyl benzoate, benzyl abietate, diethyl oxalate , dibutyl oxalate, dimethyl malonate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, di-2-ethylhexyl phthalate and alkyl trimellitates (e.g
- alkyl oleates alkenyl oleates, alkyl phthalates and alkyl trimellitates
- alkyl(C ⁇ ) oleates alkenyl(C 2 _ 12 ) oleates.
- Nitrogen-containing compounds such as formamide, N,N-dimethylformamide , acetonitrile and morpholine.
- Hydrocarbon compounds such as n-pentane, n-hexane , isohexane, n-heptane, n-octane, n-decane, petroleum ether, petroleum benzine, petroleum fractions (e.g., paraffins, kerosine and gas oil), cyclohexane, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene and dimethyl sulfoxide.
- Vegetable oils such as soybean oil and cottonseed oil.
- polyalkylene glycol monoalkyl ethers and polyalkylene glycol dialkyl ethers are most preferable.
- the weight ratio of the nitrogen-containing compound (A) In the enhancer composition for agricultural chemicals comprising a nitrogen-containing compound (A) , a chelating agent (B) and an adjuvant for penetration (D) according to the present invention, the weight ratio of the nitrogen-containing compound
- the adjuvant for penetration (D) preferably ranges from 1/5 to 5/1, still more preferably from 1/2 to 2/1.
- the ratio exceeds 5/1, the enhancing effect of the adjuvant for penetration (D) is unsatisfactory.
- the ratio is lower than 1/5, the enhancing effect of the adjuvant for penetration (D) is no longer improved and, unfavorably, the combination use of the enhancer composition for agricultural chemicals comprising a nitrogen-containing compound (A) , a chelating agent
- the agricultural chemical composition of the present invention comprises the above-mentioned enhancer composition for agricultural chemicals of the present invention and an agricultural chemical.
- the term "agricultural chemical” means one which is employed as an active or principle ingredient in common agricultural chemical compositions or preparations.
- the enhancer composition for agricultural chemicals of the present invention which is employed for preparing the agricultural chemical composition of the present invention, may further comprises a surfactant (C) other than the nitrogen-containing compounds (A) and/or an adjuvant for penetration (D) as described above.
- the weight ratio of the sum total of the nitrogen-containing compound (A) and the chelating agent (B) to the agricultural chemical(s) is from 0.05 to 50, preferably from 0.05 to 20 and still more preferably from 0.1 to 10.
- this ratio is below 0.05, any desired effect of enhancing the effectiveness of the agricultural chemical(s) can not be fully achieved.
- this ratio exceeds 50, on the other hand, the enhancing effect is no longer improved.
- Zineb Zineb [zinc ethylenebis(dithio- carbamate)], Maneb [manganese ethylenebis(dithio- carba ate)], Thiram [bis(dimethylthiocarbamoyl) disulfide] , Mancozeb [complex of zinc and manganese ethylenebis(dithiocarbamate) ] , Polycarbamate [dizinc bis(dimethyldithiocarbamate) ethylenebis(dithio ⁇ carbamate)], Propineb [polymeric zinc propylenebis- (dithiocarbamate) ] , benzimidazole fungicides such as Benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazole- carbamate] and Thiophanate-methyl [1,2-bis(3-methoxy- carbonyl-2-thioureido)benzene]
- pyrethroid insecticides such as Fenvalerate [ ⁇ -cyano- 3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoate] and Cyfluthrin (Baythroid) [ ⁇ -cyano-4-fluoro-3- phenoxyphenylmethyl 3-(2,2-dichloroethenyl)-2,2- dimethylcyclcopropanecarboxylate] ; organophosphorus insecticides such as Dichlorvos (DDVP) [dimethyl 2,2-dichlorovinyl phosphate], Fenitrothion (MEP) [0,0-dimethyl-0-(3-methy1-4-nitrophenyl)thio- phosphate] , Malathion (Malathon) [S-[1,2-bis(ethoxy- carbonyl)ethyl]dimethyl phosphorothiol-thionate] , Dimethoate [dimethyl S-(N-methylcar
- pyrethrin preparations which originate from Chrysanthemum iner ⁇ riaefol ium
- rotenone preparations which originate from Derris which is a shrub of the pulse family
- nicotine preparations [containing 3-(l-methyl-2-pyrrolidinyl)pyridine sulfate] .
- IGR insect growth regulators
- diflubenzuron [1-(4-chlorophenyl)- 3-(2,6-difluorobenzoyl)urea]
- teflubenzuron [l-(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-difluoro- benzoyl)urea]
- buprofezin [2-tert-butylimino-3- isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-l,3,5- thiadiazin-4-one]
- fenoxycarb [ethyl 2-(4- phenoxyphenoxy)ethylcarbamate]
- miticides or acaricides
- Pyridaben [2-tert-butyl-5-(4-tert-butyl- benzylthio)-4-chloropyridazin-3(2H)-one]
- Acricid [2,4-dinitro-6-sec-butylphenyldimethylacrylate]
- Chloromite [isopropyl 4,4-dichlorobenzylate]
- Chlorobenzilate (Akar) [ethyl 4,4'-dichlorobenzilate]
- Dicofol (Kelthane) [1 , 1-bis(p-chlorophenyl)-2 , 2 , 2- trichloroethanol]
- Benzoximate (Citrazon) [ethyl-O- benzoyl-3-chloro-2, 6-dimethoxybenzohydroximate]
- Propargite (Omite) [2-(p-tert-butyl) [2-(
- herbicides included are acid amide hebicides such as Propanil (DCPA) [3' ,4'- dichloropropionanilide] and Alachlor [2-chloro-2' , 6 ' - diethyl-N-(methoxyethyl)acetanilide] ; urea herbicides such as Diuron (DCMU) [3- (3,4-dichlorophenyl)-1,1- dimethylurea] and Linuron [3- (3,4-dichlorophenyl)-1- methoxy-1-methylurea) ; dipyridyl herbicides such as Paraquat Dichloride (Paraquat) [1 , 1 ' -dimethyl-4,4' - bipyridirium dichloride] and Diquat Dibromide (Diquat) [6 , 7-dihydrodipyrido[l, 2-a:2' , 1 ' -c]-pyraz
- DCPA
- MH maleic hydrazide
- Ethephon 2-chloroethyl- phosphonic acid
- fungicide an insecticide, a miticide or a plant growth regulator
- a herbicide it is preferable to use one other than organophosphorus herbicides.
- the agricultural chemical composition of the present invention may be formulated into any preparation such as liquid preparations, emulsions, wettable powders, granules, powders and flowables without any limitation. Accordingly, the agricultural chemical composition of the present invention may contain other additives which are selected depending on the formulation or preparation, for example, emulsifiers, dispersing agents and carriers.
- the agricultural chemical composition according to the present invention may further contain a pH regulator, an inorganic salt or a thickener, if required.
- pH regulators to be used in the present invention include citric acid, phosphoric acid (e.g., pyrophosphoric acid) and gluconic acid, and salts thereof.
- inorganic acid salts to 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, ammonium nitrate, ammonium phosphate, ammonium thiocyanate, ammonium chloride and ammonium sulfamate.
- inorganic mineral salts such as clay, talc, bentonite, zeolite, calcium carbonate, diatomaceous earth and white carbon
- inorganic ammonium salts such as ammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium thiocyanate, ammonium chloride and ammonium sulfamate.
- thickeners to be used in the present invention include natural, semisynthetic and synthetic, water-soluble thickeners.
- natural mucilaginous matters xanthane gum and zanflow, which are derived from microorganism, and pectine, gum arabic and guar gum, which are derived from plant, are cited.
- semisynthetic mucilaginous matters methylated, carboxyalkylated and hydroxyalkylated products of cellulose such as methylcellulose, carboxymethylcellulose and hydroxymethylcellulose, methylated, carboxyalkylated and hydroxyalkylated products of starch derivatives, and sorbitol are cited.
- polyacrylates, polymaleates, polyvinylpyrrolidone and pentaerythritol/ethyleneoxide adducts are cited as synthetic mucilaginous matters.
- the agricultural chemical composition of the present invention may further contain one or more ingredients such as plant growth regulators other than those cited above, fertilizers and preservatives.
- the agricultural chemical composition of the present invention is used in order to control fungi (or bacteria), insects, mites (or acarids) and herbs or to regulate the growth of plants.
- the agricultural chemical kit according to the present invention comprises a container containing the enhancer composition according to the present invention and another container containing an agricultural chemical composition.
- the enhancer composition may comprise at least one nitrogen-containing compound (A) s-elected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent.
- the enhancer composition may further comprise a surfactant (C) other than the nitrogen-containing compounds (A) and/or an adjuvant for penetration (D) .
- another agricultural chemical kit comprises a container containing at least one nitrogen-containing compound (A) selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent (B) , a container containing a surfactant (C) other than the nitrogen-containing compounds (A) and a container containing an agricultural chemical composition.
- the container containing at least one nitrogen-containing compound (A) and a chelating agent (B) and/or the container containing a surfactant (C) may further contain an adjuvant for penetration (D) .
- an agricultural chemical kit which comprises a container containing at least one nitrogen-containing compound (A) selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent (B) , a container containing an adjuvant for penetration (D) and a container containing an agricultural chemical composition
- another agricultural chemical kit which comprises a container containing at least one nitrogen-containing compound (A) selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt and a chelating agent (B) , a container containing a surfactant (C) other than the nitrogen-containing compounds (A) , a container containing an adjuvant for penetration (D) and a container containing an agricultural chemical composition, are included in the scope of the present invention.
- the "agricultural chemical composition” which is a constituent of the kit is a composition which comprises an agricultural chemical(s), is free from the nitrogen-containing compound (A) and is in the form of, for example, an emulsion, a liquid or a wettable powder.
- the agricultural chemical composition may contain a small amount of the chelating agent (B) .
- a composition comprising an agricultural chemical is separated from the enhancer composition for agricultural chemicals comprising a nitrogen-containing compound (A) and a chelating agent (B) according to the present invention.
- the agricultural chemical composition which is a constituent of the kit differs from the agricultural chemical composition of the present invention which comprises the enhancer composition for agricultural chemicals according to the present invention and an agricultural chemical(s) in admixture.
- Each of contents in these containers is not restricted in their form but appropriately prepared depending on the use and purpose.
- the material of the container is not restricted so long as it is not react with or affect the content. Examples of the material include plastics, glass, foil, etc.
- the enhancer composition according to the present invention is applied with an agricultural chemical to a locus which would benefit from such treatment, i.e., the application of the enhancer composition and the agricultural chemical.
- the enhancer composition and the agricultural chemical are used with water or a liquid carrier.
- the agricultural chemical composition of the present invention containing the nitrogen-containing compound (A) and the chelating agent (B) and having a preparation form is used (if necessary, the agricultural chemical composition is diluted with, for example, tap water), (2) another one wherein the enhancer composition of the present invention is added to an agricultural chemical composition, which has been diluted with water, and (3) another one wherein the enhancer composition of the present invention is diluted with water and then an agricultural chemical composition is diluted with the resultant diluted solution of the enhancer composition, are useful.
- the desired enhancement effect can be achieved by either means.
- the agricultural chemical composition of the present invention includes one containing the agricultural chemical in high concentration, the nitrogen-containing compound (A) in high concentration and the chelating agent (B) in high concentration, and another one containing the agricultural" chemical in an appropriate concentration for application, the nitrogen-containing compound (A) in an appropriate concentration for application and the chelating agent (B) in an appropriate concentration for application.
- the agricultural chemical composition is diluted with water, etc., for example, just before applying.
- the agricultural chemical compositions used in the above cases (2) and (3) include those containing the agricultural chemical in high concentration and being free from the nitrogen-containing compound (A) .
- the contents of the agricultural chemical, the nitrogen-containing compound (A) and the chelating agent (B) in the diluted solution are not limited.
- the content of the agricultural chemical in the diluted solution depends on, for example, the kind of the agricultural chemical and its use. While the contents of the nitrogen-containing compound (A) and the chelating agent (B) in the diluted solution depends on, for example, the kind of the agricultural chemical to be mixed.
- the diluted liquid comprising an appropriate amount of an agricultural chemical, an appropriate amount of the nitrogen-containing compound (A) and an appropriate amount of the chelating agent (B) is applied to, for example, plants, crops, vegetables, fruits, trees, fruit trees, grasses, weeds or seeds, and, at the same time, to fungi, bacteria, insects, acarids or mites.
- the diluted liquid is applied to a farm, a plantation, a fruit garden, an orchard, a flower garden, a lawn, a wood and a forest.
- Spray gun (mf. by Iwata Tosoki Kogyo K.K. , type RG) was used for the application of the agricultural chemical compositions to the crabgrasses.
- the crabgrasses in the pots were uniformly sprayed with each of the agricultural chemical compositions at a ratio corresponding to 1000 1/ha (liter per hectare) to evaluate the herbicidal efficacy.
- the above-ground part of the fresh plant was weighed and the result was expressed in a herbicidal ratio on the basis of the fresh weight of the above-ground part in the untreated lot (see the following formula) .
- Herbicidal untreated lot test lot ratio x 100
- Tables 5 , 6-1 and 6-2 show the herbicidal ratios of the agricultural chemical compositions .
- Nissorun V emulsion containing 55% by weight of active ingredients including 50% by weight of hexythiazox and 5% by weight of DDVP
- Osadan wettable powder 25 containing 25% by weight of phenbutatin oxide as the active ingredient
- the same enhancer compositions for agricultural chemicals as those employed in Example 1 were used.
- the concentration of each enhancer composition for agricultural chemicals i.e., sum total of compound (A), chelating agent (B) and surfactant (C)] in the dilution was adjusted to 0.05% by weight. Further, the above procedure was repeated without using any enhancer compositions. Tables 7, 8-1 and 8-2 show the results.
- Rice planthopper larvae of the third instar were incubated and used in an efficacy test on insecticides in triplicate runs by the dipping method (each lot having 10 larvae) .
- the insecticidal ratio was determined in the same manner as the one employed for the determination of the miticidal ratio.
- Commercially available insecticides i.e., Sumithion emulsion (containing 50% by weight of MEP as the active ingredient) and Malathon emulsion (containing 50% by weight of malathon as the active ingredient) were each diluted 3,000-fold with the use of deionized water, and the dilutions thus obtained were used.
- each enhancer composition for agricultural chemicals, those employed in Example 1 were used in such a manner as to adjust the concentration of each enhancer composition [i.e., sum total of compound (A), chelating agent (B) and surfactant (C)] in the diluted solution to 0.1% by weight.
- Tables 9, 10-1 and 10-2 show the results.
- a marketed fungicide i.e. , Bayleton wettable powder 5 (containing 5% by weight of triadimefon as the active ingredient) was diluted 3, 000-fold with the 2,500-fold dilution (diluent: deionized water) of each of the enhancer compositions employed in Example 1.
- the dilution thus obtained was applied onto the seedlings at a ratio of 5 ml per pot. After allowing the pots to stand at 25° C under a relative humidity of 85%, lesions were counted and the preventive value was calculated in accordance with the following equation. Tables 11, 12-1 and 12-2 show the results .
- Examples 1 to 4 show tests whereby the efficacies of the enhancer compositions for agricultural chemicals of the present invention were compared with those of common cationic surfactants employed as enhancers for agricultural chemicals or chelating agents.
- the chelating agent further enhanced the effect of at least one nitrogen-containing compound selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt in enhancing the efficacy of the agricultural chemicals in the enhancer compositions for agricultural chemicals of the present invention
- the enhancer compositions for agricultural chemicals of the present invention exhibited remarkable effects of enhancing the efficacy of the agricultural chemicals.
- the chelating agent specifically enhances the effect of at least one nitrogen-containing compound selected from the group consisting of a tertiary amine, a tertiary amine salt and a quaternary ammonium salt of enhancing the efficacy of the agricultural chemicals.
- Example 13 shows the results.
- the term "herbicide concn.” means the concentration of the marketed herbicide formulation in a dilution to be applied, the term “enhancer compn.
- concn means the concentration of the enhancer composition [i.e., sum total of compound (A), chelating agent (B) and surfactant (C)] in a dilution to be applied, and the term, "agricultural chemical” means the active ingredien (s) of the marketed herbicide formulation.
- the enhancer compositions for agricultural chemicals listed in Table 14 were prepared by adding an adjuvant for penetration to each of the enhancer compositions listed in Tables 4-1 and 4-2.
- the above-mentioned enhancer compositions for agricultural chemicals listed in Table 14 were each dissolved in deionized water to give a 0.05% by weight [as sum total of compound (A) , chelating agent (B) and surfactant (C)] dilution.
- commercially available herbicides i.e., Karmex wettable powder (containing 78.5% by weight of DCMU as the active ingredient)
- Herbiace liquid formulation containing 20% by weight of Bialaphos as the active ingredient
- Roundup liquid formulation containing 41% by weight of isopropylamine salt of Glyphosate as the active ingredient
- Example 14 The same test as the one effected in Example 1 was carried out by using the agricultural chemical compositions thus obtained, and their herbicidal ratios were determined. Table 15 show the results. Table 14
- Invention 45 22 diethylene glycol monobutyl 1/0.5 1/0.63 product ether
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DE69419500T DE69419500T2 (en) | 1993-12-28 | 1994-12-27 | EFFECTIVENING COMPOSITIONS FOR AGROCHEMICALS AND AGROCHEMICAL COMPOSITIONS |
BR9406470A BR9406470A (en) | 1993-12-28 | 1994-12-27 | Composition and process for improving chemicals applicable in agriculture and chemical composition applicable in agriculture |
JP51792295A JP3507078B2 (en) | 1993-12-28 | 1994-12-27 | Pesticide efficacy enhancer composition and pesticide composition |
EP95904000A EP0685995B1 (en) | 1993-12-28 | 1994-12-27 | Enhancer composition for agricultural chemicals and agricultural chemical composition |
US09/053,084 US6706666B2 (en) | 1993-12-28 | 1998-04-01 | Enhancer composition for agricultural chemicals and agricultural chemical composition |
US10/747,948 US20040151749A1 (en) | 1993-12-28 | 2003-12-31 | Enhancer composition for agricultural chemicals and agricultural chemical composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP5/337502 | 1993-12-28 | ||
JP33750293 | 1993-12-28 |
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US09/053,084 Continuation US6706666B2 (en) | 1993-12-28 | 1998-04-01 | Enhancer composition for agricultural chemicals and agricultural chemical composition |
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WO1995017817A1 true WO1995017817A1 (en) | 1995-07-06 |
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ID=18309263
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PCT/JP1994/002263 WO1995017817A1 (en) | 1993-12-28 | 1994-12-27 | Enhancer composition for agricultural chemicals and agricultural chemical composition |
Country Status (7)
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US (2) | US6706666B2 (en) |
EP (1) | EP0685995B1 (en) |
JP (1) | JP3507078B2 (en) |
CN (1) | CN1112846C (en) |
BR (1) | BR9406470A (en) |
DE (1) | DE69419500T2 (en) |
WO (1) | WO1995017817A1 (en) |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2302106A1 (en) * | 1975-02-25 | 1976-09-24 | Kao Corp | GERMICIDAL, DISINFECTANT AND ANTISEPTIC COMPOSITION |
US3998967A (en) * | 1973-12-12 | 1976-12-21 | Stauffer Chemical Company | Method of inhibiting the growth of bacteria and fungi with higher aliphatic amine salts of nitrilotriacetic acid |
JPS5276435A (en) * | 1975-12-18 | 1977-06-27 | Sakai Chemical Industry Co | Composition to prevent germs and mold |
EP0036106A2 (en) * | 1980-03-04 | 1981-09-23 | Hoechst Aktiengesellschaft | Synergistic mixtures of phosphinothricine |
EP0509346A1 (en) * | 1991-04-17 | 1992-10-21 | Kao Corporation | Biocide activator |
EP0597488A1 (en) * | 1992-11-13 | 1994-05-18 | Kao Corporation | Argricultural chemical composition |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4138483A (en) | 1977-11-11 | 1979-02-06 | M&T Chemicals Inc. | Insecticidal compositions containing certain tetraorganotin compounds and method for using same |
US4190601A (en) | 1978-05-31 | 1980-02-26 | Union Carbide Corporation | Production of tertiary amines by reductive alkylation |
JPS5598105A (en) | 1979-01-18 | 1980-07-25 | Nissan Chem Ind Ltd | Herbicidal composition |
JPH072608B2 (en) | 1986-12-04 | 1995-01-18 | モンサント コンパニ− | Aqueous concentrated herbicide formulation |
ES2058337T5 (en) | 1987-04-29 | 2005-10-01 | Monsanto Europe S.A. | IMPROVED FORMULATIONS OF GLYPHOSATE. |
US5668085A (en) | 1987-04-29 | 1997-09-16 | Monsanto Company | Glyphosate formulations comprising alkoxylated amine surfactants |
US4888447A (en) | 1988-06-30 | 1989-12-19 | Ethyl Corporation | Process for preparing alkoxylated tertiary amines |
NZ231897A (en) | 1988-12-30 | 1992-09-25 | Monsanto Co | Dry water-soluble granular composition comprising glyphosate and a liquid surfactant |
FR2644036B1 (en) | 1989-03-07 | 1992-01-17 | Rhone Poulenc Agrochimie | HERBICIDE COMBINATION OF A WATER-SOLUBLE POLYMERIC PACKAGE AND AN N-PHOSPHONOMETHYLGLYCIN-CONTAINING HERBICIDE |
SE9001446D0 (en) | 1989-05-02 | 1990-04-23 | Rhone Poulenc Agrochimie | COMPOSITIONS LIQUIDES CONCENTREES AND BASE THE N-PHOSPHONOMETHYLGYLINE |
GB9002495D0 (en) | 1990-02-05 | 1990-04-04 | Monsanto Europe Sa | Glyphosate compositions |
JPH0747523B2 (en) | 1990-04-16 | 1995-05-24 | 花王株式会社 | Biocide potency enhancer |
DE69218411T2 (en) | 1991-01-24 | 1997-08-28 | Monsanto Co | FORMULATIONS OF GLYPHOSATES |
US5258359A (en) | 1991-08-02 | 1993-11-02 | Monsanto Company | Glyphosant-containing herbicidal compositions comprising acetylenic diol rainfastness enhancing agents |
US5462912A (en) * | 1991-10-09 | 1995-10-31 | Kao Corporation | Agricultural chemical composition enhancer comprising quaternary di(polyoxyalkylene) ammonium alkyl sulfates |
US5563111A (en) * | 1993-08-03 | 1996-10-08 | Kao Corporation | Agricultural chemical composition comprising amine surfactants with at least one ester or amide linkage |
US5622911A (en) * | 1994-02-14 | 1997-04-22 | Kao Corporation | Method for enhancing the efficacy of agricultural chemical with alkoxylated fatty acid amides |
US5849663A (en) * | 1994-06-02 | 1998-12-15 | Kao Corporation | Enhancer for agricultural chemicals, enhancer composition for agricultural chemicals and method for enhancing the efficacy of agricultural chemical |
EP0762830B1 (en) * | 1994-06-02 | 2001-12-19 | Kao Corporation | Method for enhancing the efficacy of agricultural chemicals |
JP3113161B2 (en) * | 1994-11-25 | 2000-11-27 | 花王株式会社 | Pesticide efficacy enhancer composition and pesticide composition |
MY114016A (en) * | 1995-06-27 | 2002-07-31 | Kao Corp | Liquid enhancer composition for amino acid series herbicides |
MY113674A (en) * | 1995-06-27 | 2002-04-30 | Kao Corp | Liquid composition for stabilizing bipyridinium series herbicides |
AR004705A1 (en) * | 1995-11-07 | 1999-03-10 | Sabba Da Silva Lima Michele | LIQUID AGROCHEMICAL COMPOSITION, METHOD TO CONVERT IT INTO A STABLE LIQUID AND ADJUVANT COMPOSITION FOR THE PREPARATION OF THE SAME. |
DE69715754T2 (en) * | 1996-03-01 | 2003-05-15 | Kao Corp., Tokio/Tokyo | EFFICIENCY AMPLIFIER FOR AGRICULTURAL CHEMICALS AND AGRICULTURAL CHEMICAL COMPOSITIONS |
MY129957A (en) * | 1996-03-06 | 2007-05-31 | Kao Corp | Aqueous liquid agricultural composition |
-
1994
- 1994-12-27 JP JP51792295A patent/JP3507078B2/en not_active Expired - Fee Related
- 1994-12-27 EP EP95904000A patent/EP0685995B1/en not_active Expired - Lifetime
- 1994-12-27 CN CN94191323A patent/CN1112846C/en not_active Expired - Fee Related
- 1994-12-27 WO PCT/JP1994/002263 patent/WO1995017817A1/en active IP Right Grant
- 1994-12-27 DE DE69419500T patent/DE69419500T2/en not_active Expired - Lifetime
- 1994-12-27 BR BR9406470A patent/BR9406470A/en not_active IP Right Cessation
-
1998
- 1998-04-01 US US09/053,084 patent/US6706666B2/en not_active Expired - Fee Related
-
2003
- 2003-12-31 US US10/747,948 patent/US20040151749A1/en not_active Abandoned
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3998967A (en) * | 1973-12-12 | 1976-12-21 | Stauffer Chemical Company | Method of inhibiting the growth of bacteria and fungi with higher aliphatic amine salts of nitrilotriacetic acid |
FR2302106A1 (en) * | 1975-02-25 | 1976-09-24 | Kao Corp | GERMICIDAL, DISINFECTANT AND ANTISEPTIC COMPOSITION |
JPS5276435A (en) * | 1975-12-18 | 1977-06-27 | Sakai Chemical Industry Co | Composition to prevent germs and mold |
EP0036106A2 (en) * | 1980-03-04 | 1981-09-23 | Hoechst Aktiengesellschaft | Synergistic mixtures of phosphinothricine |
EP0509346A1 (en) * | 1991-04-17 | 1992-10-21 | Kao Corporation | Biocide activator |
EP0597488A1 (en) * | 1992-11-13 | 1994-05-18 | Kao Corporation | Argricultural chemical composition |
Non-Patent Citations (1)
Title |
---|
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Week Y32, Derwent World Patents Index; AN 56498Y * |
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WO1997032476A1 (en) * | 1996-03-06 | 1997-09-12 | Kao Corporation | Aqueous liquid agricultural composition |
US5948421A (en) * | 1996-03-06 | 1999-09-07 | Kao Corporation | Aqueous liquid agricultural composition |
US6500783B1 (en) | 1998-11-30 | 2002-12-31 | Monsanto Technology Llc | Process and compositions promoting biological effectiveness of exogenous chemical substances in plants |
EP1139764A1 (en) * | 1999-01-15 | 2001-10-10 | Cognis Corporation | Adjuvant composition |
EP1139764A4 (en) * | 1999-01-15 | 2002-04-03 | Cognis Corp | Adjuvant composition |
US6432878B1 (en) | 1999-01-15 | 2002-08-13 | Cognis Corporation | Adjuvant composition |
US6645913B2 (en) | 1999-01-15 | 2003-11-11 | Cognis Corporation | Adjuvant composition |
EP1044608A1 (en) * | 1999-03-31 | 2000-10-18 | Altinco, S.L. | A phtosanitary product comprising quaternary ammonium salts as enhancers |
US6521785B2 (en) * | 1999-08-03 | 2003-02-18 | Syngenta Participations Ag | Pesticide formulations containing alkoxylated amine neutralized aromaticsulfonic acid surfactants |
WO2001060160A1 (en) * | 2000-02-16 | 2001-08-23 | Chemia S.P.A. | Herbicidal composition |
US6897184B2 (en) | 2002-05-31 | 2005-05-24 | Kao Corporation | Enhancer for agricultural chemicals |
US7141532B2 (en) | 2002-08-31 | 2006-11-28 | Monsanto Technology Llc | Process for the preparation of a dry pesticidal composition containing a dicarboxylate component |
US7883715B2 (en) | 2002-08-31 | 2011-02-08 | Monsanto Technology Llc | Pesticide compositions containing dicarboxylic acids |
EP2292095A2 (en) | 2002-08-31 | 2011-03-09 | Monsanto Technology LLC | Pesticide compositions containing a dicarboxylic acid or derivative thereof |
US7226892B2 (en) | 2003-02-03 | 2007-06-05 | Durga Technologies Aps | Herbicidal composition and use |
WO2004068948A1 (en) * | 2003-02-03 | 2004-08-19 | Kim Carl-Christian Henningsen | Herbicidal composition and use |
US9980479B2 (en) | 2004-06-07 | 2018-05-29 | Syngenta Crop Protection, Llc | Method of reducing nematode damage |
AU2006326729B2 (en) * | 2005-12-13 | 2011-12-08 | Bayer Cropscience Ag | Insecticidal compositions with improved effect |
US8247351B2 (en) | 2005-12-13 | 2012-08-21 | Bayer Cropscience Ag | Insecticidal compositions having improved effect |
WO2007068427A2 (en) | 2005-12-13 | 2007-06-21 | Bayer Cropscience Ag | Herbicidal compositions having improved effect |
WO2007073856A2 (en) | 2005-12-15 | 2007-07-05 | Bayer Cropscience Ag | 3'-alkoxy-spirocyclopentyl-substituted tetramic and tetronic acids |
WO2007096058A1 (en) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkylphenyl substituted cyclic ketoenols |
EP2186791A1 (en) | 2006-02-21 | 2010-05-19 | Bayer CropScience AG | Cycloalkyl-phenyl-substituted cyclic ketoenoles |
EP2186805A1 (en) | 2006-02-21 | 2010-05-19 | Bayer CropScience AG | Cycloalkyl-phenyl-substituted cyclic ketoenoles |
EP2184275A1 (en) | 2006-02-21 | 2010-05-12 | Bayer CropScience AG | Cycloalkyl-phenyl-substituted cyclic ketoenoles |
US8067458B2 (en) | 2006-04-22 | 2011-11-29 | Bayer Cropscience Ag | Alkoxyalkyl-substituted cyclic ketoenols |
US8173697B2 (en) | 2006-06-02 | 2012-05-08 | Bayer Cropscience Ag | Alkoxyalkyl-substituted cyclic keto-enols |
US8507537B2 (en) | 2006-10-25 | 2013-08-13 | Bayer Cropscience Ag | Trifluromethoxyphenyl-substituted tetramic acid derivatives pesticides and/or herbicides |
US9000189B2 (en) | 2006-12-04 | 2015-04-07 | Bayer Cropscience Ag | Biphenyl-substituted spirocyclic ketoenols |
US8993782B2 (en) | 2006-12-04 | 2015-03-31 | Bayer Cropscience Ag | Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives |
EP2534952A1 (en) | 2007-05-25 | 2012-12-19 | Bayer CropScience AG | Insecticide compositions of 2-cyanobenzolsulfonamides and their isomeric forms with improved properties |
DE102007024575A1 (en) | 2007-05-25 | 2008-11-27 | Bayer Cropscience Ag | Insecticidal compositions of 2-cyanobenzenesulfonamide compounds and their isomeric forms having improved activity |
US8604068B2 (en) | 2007-05-25 | 2013-12-10 | Bayer Cropscience Ag | Insecticidal compositions of 2-cyanobenzene sulfonamide compounds and isomeric forms thereof having improved effect |
WO2009015801A1 (en) | 2007-08-02 | 2009-02-05 | Bayer Cropscience Ag | Oxaspirocyclic spiro-substituted tetramic and tetronic acid derivatives |
US8859466B2 (en) | 2007-08-02 | 2014-10-14 | Bayer Cropscience Ag | Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives |
US8435549B2 (en) | 2007-09-25 | 2013-05-07 | Bayer Cropscience Ag | Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives |
WO2009039975A1 (en) | 2007-09-25 | 2009-04-02 | Bayer Cropscience Ag | Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives |
EP2092824A1 (en) | 2008-02-25 | 2009-08-26 | Bayer CropScience AG | Heterocyclyl pyrimidines |
WO2009115262A1 (en) | 2008-03-19 | 2009-09-24 | Bayer Cropscience Ag | 4'4'-dioxaspiro-spirocyclically substituted tetramates |
EP2103615A1 (en) | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclic substituted tetramates |
EP2123159A1 (en) | 2008-05-21 | 2009-11-25 | Bayer CropScience AG | (1,2-Benzisothiazol-3-yl)(thio)carbamates and (1,2-Benzisothiazol-3-yl)(thio)oxamates and their oxidation forms as pesticides |
US8367873B2 (en) | 2008-10-10 | 2013-02-05 | Bayer Cropscience Ag | Phenyl-substituted bicyclooctane-1,3-dione derivatives |
US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8173641B2 (en) | 2008-12-15 | 2012-05-08 | Bayer Cropscience Ag | 4-amino-1,2,3-benzoxathiazine-derivatives as pesticides |
EP2196461A1 (en) | 2008-12-15 | 2010-06-16 | Bayer CropScience AG | 4-Amino-1,2,3-benzoxathiazine-derivatives as pesticides |
EP2484676A2 (en) | 2008-12-18 | 2012-08-08 | Bayer CropScience AG | Tetrazol-substituted anthranilic acid amides as pesticides |
US8324390B2 (en) | 2008-12-18 | 2012-12-04 | Bayer Cropscience Ag | Tetrazole-substituted anthranilamides as pesticides |
WO2010094418A2 (en) | 2009-02-23 | 2010-08-26 | Bayer Cropscience Ag | Insecticidal compositions having an improved effect |
EP2223598A1 (en) | 2009-02-23 | 2010-09-01 | Bayer CropScience AG | Insecticidal compounds with improved effect |
US8518985B2 (en) | 2009-03-11 | 2013-08-27 | Bayer Cropscience Ag | Haloalkylmethyleneoxyphenyl-substituted ketoenols |
EP3153503A1 (en) | 2009-03-11 | 2017-04-12 | Bayer Intellectual Property GmbH | Intermediates for halogenoalkylmethylenoxy-phenyl-substituted ketoenols |
US9045390B2 (en) | 2009-03-11 | 2015-06-02 | Bayer Cropscience Ag | Haloalkylmethyleneoxyphenyl-substituted ketoenols |
WO2010102758A2 (en) | 2009-03-11 | 2010-09-16 | Bayer Cropscience Ag | Halogenalkylmethylenoxy-phenyl-substituted ketoenols |
US9572341B2 (en) | 2009-03-30 | 2017-02-21 | Kao Corporation | Method for enhancing efficacy of agrichemical, and agrichemical-containing composition |
US9161530B2 (en) | 2009-03-30 | 2015-10-20 | Kao Corporation | Method for enhancing efficacy of agrichemical, and agrichemical-containing composition |
WO2010113692A1 (en) | 2009-03-30 | 2010-10-07 | 花王株式会社 | Method for enhancing efficacy of agrichemical, and agrichemical-containing composition |
US20130012384A1 (en) * | 2009-05-19 | 2013-01-10 | Bayer Cropscience Ag | Spiroheterocyclic Tetronic Acid Derivatives |
US8592610B2 (en) | 2009-05-19 | 2013-11-26 | Bayer Cropscience Ag | Spiroheterocyclic tetronic acid derivatives |
WO2010133337A1 (en) | 2009-05-19 | 2010-11-25 | Bayer Cropscience Ag | Herbicidal spiroheterocyclic tetronic acid derivatives |
US8318956B2 (en) | 2009-05-19 | 2012-11-27 | Bayer Cropscience Ag | Spiroheterocyclic tetronic acid derivatives |
EP2266397A1 (en) | 2009-06-18 | 2010-12-29 | LANXESS Deutschland GmbH | Azole compounds containing amidoalkylamine to protect technical materials |
EP2263456A1 (en) | 2009-06-18 | 2010-12-22 | LANXESS Deutschland GmbH | Azole compounds containing amidoalkylamine to protect technical materials |
WO2011098440A2 (en) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Biphenyl substituted cyclical keto-enols |
WO2011098443A1 (en) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Spiroheterocyclical substituted tetramic acid derivatives |
US8901038B2 (en) | 2010-02-10 | 2014-12-02 | Bayer Cropscience Ag | Biphenyl-substituted cyclic ketoenols |
US9809542B2 (en) | 2010-02-10 | 2017-11-07 | Bayer Intellectual Property Gmbh | Spiroheterocyclically substituted tetramic acid derivatives |
WO2011131623A1 (en) | 2010-04-20 | 2011-10-27 | Bayer Cropscience Ag | Insecticidal and/or herbicidal composition having improved activity on the basis of spiro-heterocyclically substituted tetramic acid derivatives |
US8889592B2 (en) | 2010-04-20 | 2014-11-18 | Bayer Cropscience Ag | Insecticidal and/or herbicidal composition having improved activity based on spiroheterocyclically substituted tetramic acid derivatives |
WO2012000902A1 (en) | 2010-06-29 | 2012-01-05 | Bayer Cropscience Ag | Improved insecticidal compositions comprising cyclic carbonylamidines |
US10188101B2 (en) | 2010-09-03 | 2019-01-29 | Kao Corporation | Method for producing an agricultural product |
WO2012059436A2 (en) | 2010-11-02 | 2012-05-10 | Bayer Cropscience Ag | Phenyl-substituted bicyclooctane-1,3-dione-derivatives |
EP2719680A1 (en) | 2010-11-02 | 2014-04-16 | Bayer Intellectual Property GmbH | Phenyl-substituted bicycle octane 1.3 dion derivatives |
WO2012110519A1 (en) | 2011-02-17 | 2012-08-23 | Bayer Cropscience Ag | Substituted 3-(biphenyl-3-yl)-8,8-difluoro-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy and halogen-substituted spirocyclic ketoenols |
US8946124B2 (en) | 2011-02-17 | 2015-02-03 | Bayer Intellectual Property Gmbh | Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy and halogen-substituted spirocyclic ketoenols |
WO2012110518A1 (en) | 2011-02-17 | 2012-08-23 | Bayer Pharma Aktiengesellschaft | Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy |
WO2012116960A1 (en) | 2011-03-01 | 2012-09-07 | Bayer Cropscience Ag | 2-acyloxy-pyrrolin-4-ones |
US9204640B2 (en) | 2011-03-01 | 2015-12-08 | Bayer Intellectual Property Gmbh | 2-acyloxy-pyrrolin-4-ones |
CN103491774A (en) * | 2011-04-26 | 2014-01-01 | 辛根塔有限公司 | Formulation component |
CN103491774B (en) * | 2011-04-26 | 2016-03-30 | 辛根塔有限公司 | Preparation component |
US10206388B2 (en) | 2011-04-26 | 2019-02-19 | Syngenta Limited | Formulation component |
WO2012146887A1 (en) * | 2011-04-26 | 2012-11-01 | Syngenta Limited | Formulation component |
WO2012146889A1 (en) * | 2011-04-26 | 2012-11-01 | Syngenta Limited | Formulation component |
WO2012146888A1 (en) * | 2011-04-26 | 2012-11-01 | Syngenta Limited | Formulation component |
US9173397B2 (en) | 2011-04-26 | 2015-11-03 | Syngenta Limited | Formulation component |
US8728454B1 (en) | 2012-10-30 | 2014-05-20 | The Clorox Company | Cationic micelles with anionic polymeric counterions compositions thereof |
US8933010B2 (en) | 2012-10-30 | 2015-01-13 | The Clorox Company | Cationic micelles with anionic polymeric counterions compositions thereof |
US8883705B2 (en) | 2012-10-30 | 2014-11-11 | The Clorox Company | Cationic micelles with anionic polymeric counterions systems thereof |
US8883706B2 (en) | 2012-10-30 | 2014-11-11 | The Clorox Company | Anionic micelles with cationic polymeric counterions systems thereof |
US8765114B2 (en) | 2012-10-30 | 2014-07-01 | The Clorox Company | Anionic micelles with cationic polymeric counterions methods thereof |
US8728530B1 (en) | 2012-10-30 | 2014-05-20 | The Clorox Company | Anionic micelles with cationic polymeric counterions compositions thereof |
WO2016001129A1 (en) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Improved insecticidal compositions |
WO2019197621A1 (en) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Oil-based suspension concentrates |
WO2019197619A1 (en) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Oil-based suspension concentrates |
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US20010029240A1 (en) | 2001-10-11 |
DE69419500D1 (en) | 1999-08-19 |
US6706666B2 (en) | 2004-03-16 |
EP0685995B1 (en) | 1999-07-14 |
JP3507078B2 (en) | 2004-03-15 |
DE69419500T2 (en) | 1999-12-16 |
CN1112846C (en) | 2003-07-02 |
CN1118567A (en) | 1996-03-13 |
JPH08509241A (en) | 1996-10-01 |
EP0685995A1 (en) | 1995-12-13 |
US20040151749A1 (en) | 2004-08-05 |
BR9406470A (en) | 1996-01-23 |
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