WO1999048369A1 - Fungizide mischungen auf der basis von tripeloximetherderivaten und weiteren fungiziden - Google Patents
Fungizide mischungen auf der basis von tripeloximetherderivaten und weiteren fungiziden Download PDFInfo
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- WO1999048369A1 WO1999048369A1 PCT/EP1999/001911 EP9901911W WO9948369A1 WO 1999048369 A1 WO1999048369 A1 WO 1999048369A1 EP 9901911 W EP9901911 W EP 9901911W WO 9948369 A1 WO9948369 A1 WO 9948369A1
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- 0 CC(c1c(*)cc(*)cc1)NC(C(C(C1)C1(Cl)Cl)C#N)=O Chemical compound CC(c1c(*)cc(*)cc1)NC(C(C(C1)C1(Cl)Cl)C#N)=O 0.000 description 2
Classifications
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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
- A01N37/44—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
- A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
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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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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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
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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
- A01N37/36—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
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/56—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by doubly-bound oxygen atoms
Definitions
- the present invention relates to fungicidal mixtures for combating harmful fungi which
- R independently of one another hydrogen and -CC alkyl
- n 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
- R 3 is hydrogen, cyano, -CC 4 alkyl, C 1 -C haloalkyl, C -C 6 cycloalkyl;
- R 4 , R 5 are independently hydrogen
- Ci-Cg-alkylaminocarbonyl di-Ci-Cg-alkyl-aminocarbonyl
- Ci-C ⁇ -alkylaminothiocarbonyl di-Ci-Cg-alkylaminothiocarbonyl
- C 2 -C 6 alkenyl C 2 -C 6 alkenyl oxy
- Benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C ( NOR 7 ) -A n -R 3 ;
- Ci-Cg-Alkylaminocarbonyl Di-Ci-Cg-Alkylaminocarbonyl, Ci-Cg-Alkylaminothio-carbonyl, Di-Ci-Cg-Alkylaminothiocarbonyl, Ci-Cg-Alkyl- sulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Ci-Cg-
- Ci-Cg-alkyl Ci-Cg-haloalkyl, Cx-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci -Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-
- R 7 is hydrogen or Ci-Cg-alkyl
- R 8 denotes hydrogen or Ci-Cg-alkyl
- AC 3 -Cg cycloalkyl which one to three
- Ci-Cg-alkyl or C 2 -Cg-alkenyl where these radicals can be partially or completely halogenated and / or can carry one or two of the following groups: -C-C 4 alkoxy, C ⁇ -C 4 -haloalkoxy, C ⁇ -C 4 alkyl hio,
- C 1 -C 4 -alkoxycarbonyl C 3 -Cg-cycloalkyl and phenyl, where the phenyl may be partially or completely halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, -C-C 4 -alkoxy, -C-C 4 -haloalkoxy,
- R 10 , R 11 , R 12 are hydrogen or, independently of that, one of the meanings of the radical R 9 ;
- W is phenyl, naphthyl or heteroaryl, where these radicals may carry one to three of the following groups: nitro, halogen, cyano, C ⁇ _-C 4 -alkyl, halo-4 ⁇ C alkyl, C ⁇ -C 4 alkoxy, C ⁇ - C 4 haloalkoxy, C 1 -C 4 alkyl thio, C 3 -Cg cycloalkyl and C ⁇ -C 4 alkoxycarbonyl,
- R 13 Cg-Cis-bicycloalkyl or C -C] _ 5- bicycloalkenyl, where these radicals can be completely halogenated and, if they are not fully halogenated, two carbon atoms of these radicals together with a C 3 -C 5 ⁇ alkylidene group five- to seven-membered saturated carbocyclic ring form and / or may carry one or independently two, three, four or five of the following groups: cyano, C 4 -alkyl, halo-C 4 alkyl, C ⁇ -C 4 ⁇ Alkoxy, -C-C 4 haloalkoxy and aryl, where the aryl can be partially or completely halogenated and / or one or independently of one another can carry two or three of the following substituents: nitro, cyano, C 1 -C 4 alkyl, C ⁇ -C 4- haloalkyl, C 1 -C 4 -alkoxy, Ci-C 4 -halo
- R 14 , R 15 , R 15 independently of one another water tof f, 6
- Ci-C ⁇ -alkyl which can be partially or completely halogenated and / or can carry one or two of the following groups: -C 4 -alkoxy, -C-C 4 -haloalkoxy, -C-C 4 -alkylthio, C 3 - C 7 -cycloalkyl, C 5 -C 7 -cycloalkenyl, the cyclic groups in turn carrying one or independently of one another two or three halogen atoms, C ⁇ -C 3 alkyl groups and / or -C ⁇ C 3 alkoxy groups and wherein the aryl may be partially or fully halogenated and / or carry one or independently two or three of the following substituents aryl, can: nitro, cyano, C 4 -alkyl, C 4 haloalkyl, C 1 -C 4 -alkoxy, Ci "C 4 -haloalkoxy and C 1 -C 4 -alkylthio or
- Ar is aryl or heteroaryl, where these radicals may carry one or independently two or three of the following groups: halogen, cyano, C 4 alkyl, C 1 -C 4 alkoxyalkyl, C ⁇ -C4 haloalkyl, C ⁇ -C 4 -alkoxy,
- the object of the present invention was to provide fungicidal mixtures which have a good fungicidal action which goes beyond the effectiveness of the mixture components alone, in particular against fungal diseases in rice.
- EP 341,475 common name: Carpropamid (trade name: WIN®, Bayer)
- the compounds I can be obtained as E / Z isomer mixtures, which e.g. can be separated into the individual compounds by crystallization or chromatography in the usual way.
- isomer mixtures are obtained in the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
- the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
- the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
- R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
- R 3 is CF 3 .
- R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, if appropriate subst.
- Aryl or hetaryl is.
- R 5 for optionally subst.
- Aryl or hetaryl is.
- R 5 is optionally substituted.
- R 5 for optionally subst. Furyl, thienyl or pyrrolyl.
- R 5 for optionally subst.
- R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
- R 5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy, C 1 -C 4 alkylamino, di-C ⁇ -C 4 ⁇
- R 4 represents hydrogen, Ci-Cg-alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl .
- R 4 is Ci-Cg-alkyl
- the carbon atom which carries the groups R 9 and R 10 preferably has the R configuration.
- Cycloalkylalkane carboxamides IV are preferred in which R 9 is methyl and R 10 is either methyl or hydrogen; Compounds IV in which R 9 is methyl and R 10 is hydrogen are particularly preferred.
- Cycloalkylalkanecarboxamides of the formula IV are furthermore preferred, in which W represents optionally substituted phenyl, which is in particular substituted in the 2-position or in the 2 and 4 positions.
- W represents optionally substituted phenyl, which is in particular substituted in the 2-position or in the 2 and 4 positions.
- the substitution in the 4-position on the phenyl ring is very particularly preferred, and preferably there 10
- the substituents R 3 and R 4 are preferably C 1 -C 4 -alkyl and in particular methyl. Also preferred is the combination in which one of the two substituents is hydrogen and the other is C 1 -C 4 -alkyl and in particular methyl.
- ⁇ -chloro or ⁇ -bromocycloalkylalkane carboxamides IV bromine or chlorine
- cycloalkylalkane carboxamides of the formula IV are preferred, where A is unsubstituted or substituted cyclopropyl.
- cyclopropyl is preferred, which carries one to three substituents selected from the group consisting of chlorine and C 1 -C 3 -alkyl, in particular methyl.
- Chlorinated cyclopropyl preferably carries two chlorine atoms and this m mmal position on the cyclopropane.
- Alkylated or preferably methylated cyclopropyl preferably carries one of the alkyl (methyl) substituents on the carbon atom at the point of attachment of the cyclopropane to the rest of the molecule.
- Carboxamides IVb.OOl to IVb.108 of the general formula IVb in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1. 14
- Carboxamides IVc.OOl to IVc.108 of the general formula IVc in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVd.OOl to IVd.108 of the general formula IVd in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVe.OOl to IVe.108 of the general formula IVe in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVf.OOl to IVf.108 of the general formula IVf in which the meanings of the combinations of Z 1 , z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVg.OOl to IVg.108 of the general formula IVg in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVh.OOl to IVh.108 of the general formula IVh in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVi.001 to IVi.108 of the general formula IVi in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVk.OOl to IVk.108 of the general formula IVk in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVm.OOl to IVm.108 of the general formula IVm in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- Carboxamides IVn.OOl to IVn.108 of the general formula IVn in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1. 17
- Carboxamides IVo.OOl to IVo.108 of the general formula IVo in which the meanings of the combinations of Z 1 , Z 2 and "*" are given by the rows in Table 1.
- the amide formation takes place according to the methods known from the literature.
- the free carboxylic acids of the formula VI ', where Z is hydroxyl, are generally m previously an activated carboxylic acid derivative VI, where Z is e.g. stands for chlorine.
- the carboxylic acids VI 'can preferably also be activated in situ by directly using the carboxylic acids VI' with the addition of e.g. Dicyclohexylcarbodiimide, chloroformic acid ethyl ester, cyanophosphonic acid diethyl ester, triphenylphosphm / azodicarboxylic acid ester, 2-pyridimidosulfide / triphenylphosphm, carbonyldumidazole, thionylchloride, phosphorothrichloride in general, phosphorus penta- chloro the carbodumides with respect to the carboxylic acids VI 'in equimolar amounts.
- Dicyclohexylcarbodiimide chloroformic acid ethyl ester
- cyanophosphonic acid diethyl ester triphenylphosphm / azodicarboxylic acid ester
- the carboxylic acids are activated via acyl cyanides, for example by reacting the carboxylic acids VI 'with diethyl cyanophosphonate, preferably in an inert solvent such as tetrahydrofuran, toluene or dichloromethane (cf. Tetrahedron Lett. 18 (1973) 1595-8).
- Activation via anhydrides takes place, for example, by reacting the carboxylic acids VI 'with carbonic acid chlorides, such as ethyl chloroformate, in general in the presence of bases and, if appropriate, in an inert solvent such as toluene or tetrahydrofuran (cf. "Houben-Weyl", 4th edition (1974) , 15/1 page 28-32).
- carbonic acid chlorides such as ethyl chloroformate
- Amide formation is preferably carried out in the presence of bases such as tertiary amines, e.g. Triethylamm or Dimethylcyclohexyla m, alkali metal carbonates, alkali metal hydroxides, Pyridm etc. performed.
- bases such as tertiary amines, e.g. Triethylamm or Dimethylcyclohexyla m, alkali metal carbonates, alkali metal hydroxides, Pyridm etc. performed.
- the reactants and the auxiliary base are expediently used in aquimolar amounts. A small excess of the auxiliary base of 0.1 - 0.5 equivalents can be helpful under certain circumstances.
- Aliphatic hydrocarbons such as hexane and ligrom, aromatic hydrocarbons such as toluene and xylene, chlorinated hydrocarbons such as methylene chloride and 1,2-dichloroethane, ethers such as methyl tert-butyl ether and tetrahydrofuran, polar aprotic solvents such as acetonitrile and dimethylformamide or esters such as ethyl acetate come as solvents or mixtures thereof in the question. 19
- the molar ratio of carboxylic acid derivatives VI to amine VII is generally 0.8 to 1.5 and preferably 0.9 to 1.1.
- the work-up is carried out as usual, e.g. by introducing the reaction mixture into water and then extracting the amide.
- Carboxylic acid derivatives of the formula VIA can still be prepared according to Scheme 2.
- the cycloalkyl acetic acids VIII can be according to the instructions in J. Am. Chem. Soc 70 (1948) 3626 -7 brominate ⁇ continuously. Working up in the presence of a Ci-Cg alcohol leads directly to the corresponding ester. The subsequent bromine / cyan exchange is as in Synth. Commun. 23 (1993) 2323-9.
- the condensation is usually carried out in a water-immiscible solvent, such as hexane, toluene or xylene, with the water formed in the reaction being removed from the circle.
- a water-immiscible solvent such as hexane, toluene or xylene
- the reaction mixture is heated to boiling under reflux for several hours.
- Bases such as e.g. Pipe ⁇ dm, Pyridm, ammonia or ß-Alanm m presence of an acid such as glacial acetic acid.
- reaction temperature of from -10 to 80 ° C. and preferably from 10 to 60 ° C. is set. 22
- the Grignard compound XI is generally used in m aquimolar amounts based on the Michael system X. In some cases it proves advantageous to use the Grignard compound in an excess of 0.2 to 0.5 molar equivalents.
- the addition is copper-catalyzed by adding 1-10 mol% of e.g. Copper (I) iodide carried out. This achieves a higher selectivity with regard to 1,2-addition versus 1,4-addition.
- Z stands for a nucleophilically interchangeable radical such as hydroxy, -CC 4 alkoxy, halogen z.
- B bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.
- Carboxylic acid derivatives of the formula VI in which n is 1 and / or A is optionally substituted cyclopropyl are particularly preferred.
- carboxylic acid derivatives of the formula VIA are preferred, in which A is cyclopropyl, which can carry one to three substituents such as chlorine and / or C 1 -C 3 -alkyl.
- Chlorinated cyclopropyl preferably carries two chlorine atoms and these in the geminal position on the cyclopropane ring.
- the compounds V can start from the corresponding carboxylic acids Xlla
- the carboxylic acids Xlla are known from EP-A 653 418.
- the amines XIII are also generally known or can be obtained by known methods (cf. WO-A 95/23 784).
- carboxylic acids Xlla are first converted into carboxy-activated derivatives XII, especially in acyl halides - e.g. the chlorides, acyl cyanides or anhydrides, transferred (cf. Tetrahedron Letters, volume 18, page 1595 to page 1598 (1973) or "Houben-Weyl", volume 15/1, page 28 to page 32). These derivatives XII are then reacted with the amines XIII in the presence of bases.
- carboxy-activated anhydrides For the preparation of the carboxy-activated anhydrides, the reaction of the carboxylic acids Xlla with carbonic acid chlorides such as isobutyl chloroformate in the presence of bases and, if appropriate, in an inert solvent such as toluene or tetrahydrofuran is preferred.
- carbonic acid chlorides such as isobutyl chloroformate
- an inert solvent such as toluene or tetrahydrofuran
- reaction of the amines XIII with the carboxy-activated carboxylic acids III is preferably carried out in a solvent such as dichloromethane, tetrahydrofuran or toluene.
- the amines XIII themselves can serve as bases, usually being recovered from the crude product.
- the carboxylic acid XII, the amine XIII, the reagent suitable for producing the carboxy-activated derivative of the carbamoylcarboxylic acid XII and the base are reacted in a one-pot process, if appropriate in an inert solvent.
- the reaction mixture thus obtained is worked up to the compounds V in a conventional manner, e.g. by mixing with water, separating the phases and, if necessary, purifying the crude products by chromatography.
- the end products sometimes fall in the form of colorless or slightly brownish, viscous oils, which can be freed of volatile components under reduced pressure and at a moderately elevated temperature. If the end products are obtained as solids, the purification can also be carried out, for example, by recrystallization or digesting.
- the compounds of formula V may optionally be present in ness ⁇ Depending on the type of substituents present as geometrical and / or optical isomers or isomer mixtures.
- the carbon atom which carries the groups R 3 and R 4 can have the R or S configuration according to the IUPAC nomenclature. Both the pure isomers described here and the mixtures of the isomers have fungicidal activity.
- the remaining part of the molecule can be arranged exo or endo in the compounds V with respect to the radical R 13 . Both isomers and their mixtures are fungicidally active.
- compounds V are preferred in which the carbon atom which carries the groups R 15 and R 16 has an R configuration. 25th
- R 15 is hydrogen and R 16 is -CC alkyl, especially methyl.
- Compounds V are furthermore preferred in which Ar represents optionally substituted phenyl which is substituted in particular in the 2-position or in the 2- and 4-position and especially in the 4-position.
- Preferred sole substituents in the 4-position are cyano, preferably methyl and especially halogen, especially chlorine.
- R 13 represents optionally substituted bicycloalkyl having 6 to 10 carbon atoms.
- Halogen fluorine, chlorine, bromine and iodine
- Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-Cg-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpenty1, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,
- Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 26
- C 1 -C 4 -alkoxy and the alkoxy parts of C 1 -C 4 -alkoxycarbonyl methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2 -methylpropoxy and 1, 1 -dirnethylethoxy;
- C 1 -C 4 haloalkoxy a C 1 -C 4 -alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2- Chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2 -difluoroethoxy, 2, 2, 2 -trifluoroethoxy, 2 -chloro-2 -fluoroethoxy, 2 -chloro-2, 2 -difluoroethoxy, 2, 2 -dichloro-2 - fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloro
- Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
- Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -Cg-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl , 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4th -Pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , l-methyl-3-buten
- Alkynyl straight-chain or branched alkynyl groups with 2 to 10 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl 2-propynyl, 15 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-
- Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocycliclamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which one to
- 25 contain three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bonded to the structure directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, e.g. 2 -Tetrahydro-
- Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-C0-) or (arylsulfonyl) are bonded to the skeleton via a sulfonyl group (-S0 -), for example phenyl ' , naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
- Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which may directly or .
- Hetarylsulfonyl are attached to the skeleton via a sulfonyl group (-S0 -), e.g.
- 5-membered heteroaryl containing one to three nitrogen atoms _5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-triazol-3-yl and 1, 3, 4-triazol-2- yl;
- 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and may contain a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-0
- Benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms or a nitrogen atom and / or an oxygen or sulfur atom 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or an oxygen - Or can contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group;
- 5-membered heteroaryl bonded via nitrogen containing one to four nitrogen atoms, or 5-membered heteroaryl bonded via nitrogen, benzo-condensed, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three May contain nitrogen atoms as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent 30th
- Carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
- 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl, 1, 2, 4-triazin-3-yl and 1,2,4, 5-tetrazin-3-yl;
- 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
- Hetarylamino aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
- Bicycloalkyl bicyclic alkyl groups with 6 to 15 carbon ring members, e.g. Bicyclo- [2.1.1] -hex-5-yl, bicyclo- [2.2.1] - hept-2-yl, bicyclo- [2.2.2] oct-2-yl, bicyclo- [3.2.1] -oct -6 -yl, bicyclo- [3.2.2] -non-6-yl, bicyclo- [4.2.2] -dec-7-yl, bicyclo- [3.1.0] -hex-l-yl, bicyclo- [ 4.1.0] -hept-1-yl, bicyclo- [4.3.0] -non-l-yl, bicyclo- [4.4.0] -dec-1-yl, particularly preferably 5-methyl-bicyclo- [2.1.
- Bicycloalkenyl bicyclic alkenyl groups with 7 to 15 carbon ring members, for example bicyclo- [2.2.1] -hept-2-en-5 -yl, bicyclo- [2.2.2] -oct-2-en-5 -yl, bicyclo- [ 4.2.2] -dec-7 -en-2 -yl, 31
- Alkylidene straight-chain or branched alkylidene groups with 3 to 5 carbon atoms, e.g. 1,3-propylidene, 1,4-butylidene, 1-methyl-1,3-propylidene, 2-methyl-1,3-propylidene, 2,2-dimethyl-1,3-propylidene, 1,5- Pentylidene, 1-methyl-l, 4-butylidene;
- Cycloalkenyl monocyclic alkyl groups with 5 to 7 carbon ring members which contain one or more double bonds, for example C 5 -C 7 -cycloalkenyl such as cyclopentenyl, cyclohexenyl and cycloheptenyl;
- Heterocyclyl three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles, which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which are bound to the skeleton, for example 2-tetrahydrofuranyl, oxiranyl, 3-tetra-hydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 - isoxazoldinyl, 4-isoxazolidinyl, 5 - isoxazolidinyl, 3 - isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3 - pyrazolidinyl, 4 - pyrazolidinyl, 5 -pyrazolidinyl, 2 -oxazolidinyl, 4 -oxazolidinyl, 5
- the pure active compounds I and II to V where th one further active substances against harmful fungi or against other pests, such as Insek ⁇ , arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers.
- the mixtures of the compounds I and at least one compound II to V can be turned simultaneously, jointly or separately at ⁇ and are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Basidiomycetes, phycoerythrine mycetes and Deuteromycetes. Some of them are systemically effective and can therefore also be used as leaf and soil fungicides.
- the mixtures according to the invention can particularly preferably be used to control Pyricularia oryzae.
- the compounds I and at least one of the compounds II to V can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the control success.
- the application rates of the mixtures according to the invention are from 0.01 to 8 kg / ha, preferably from 0.1 to 5 g / ha, in particular from 0.5 to 3.0 kg / ha, depending on the type of effect desired.
- the application rates for the compounds I are 0.01 to 2.5 kg / ha, preferably 0.05 to 2.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
- the application rates for the compounds II to V are accordingly 0.001 to 5 kg / ha, preferably 0.005 to 2 kg / ha, in particular 0.01 to 1.0 kg / ha.
- the separate or joint application of the compounds I and at least one of the compounds II to V is carried out by spraying or dusting the seeds, the plants or the soil before or after the plants have been sown or before or after the Emergence of plants.
- the fungicidal synergistic mixtures according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting , Scattering or pouring can be applied.
- the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
- the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent other organic solvents can also be used as auxiliary solvents.
- auxiliaries solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyclohexanone), Amines (eg ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g.
- kaolins, clays, talc, chalk) and synthetic stone powder e.g. highly disperse silica, silicates
- Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
- the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylated isooctyl, octyl or nonyl phenyl glycol polyphenol, alkylphenol, al
- Powder sprinklers and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to V or the mixture of the compounds I and at least one compound II to V with a solid carrier.
- Granules e.g. coating, impregnation or homogeneous granules
- a solid carrier e.g., a wax, a wax, or a wax.
- Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
- mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics and fertilizers are used as fillers or solid carriers such as ammonium sulfate, ammonium phosphate, ammonium
- the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to V or the mixture of the compounds I and at least one of the compounds II to V.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
- the application can take place before or after the infestation by the harmful fungi.
- Active ingredients 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
- IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid urea Formaldehyde condensate and 88 parts by weight of a paraffinic mineral oil.
- the active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
- ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
- the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
- Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were washed with an aqueous spore suspension. 38 sion of Pyricularia oryzae inoculated. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually
- Example active ingredient conc. in ppm the unhindered control
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ506727A NZ506727A (en) | 1998-03-24 | 1999-03-22 | Fungicide mixtures based on triple oxime ether derivatives and additional fungicides |
IL13816699A IL138166A0 (en) | 1998-03-24 | 1999-03-22 | Fungicide mixtures based on triple oxime ether derivatives and additional fungicides |
EP99916856A EP1082010A1 (de) | 1998-03-24 | 1999-03-22 | Fungizide mischungen auf der basis von tripeloximetherderivaten und weiteren fungiziden |
CA002323588A CA2323588A1 (en) | 1998-03-24 | 1999-03-22 | Fungicide mixtures based on triple oxime ether derivatives and additional fungicides |
JP2000537435A JP2002507554A (ja) | 1998-03-24 | 1999-03-22 | トリス(オキシムエーテル)誘導体及び他の殺菌剤を基礎とする殺菌剤混合物 |
BR9909017-1A BR9909017A (pt) | 1998-03-24 | 1999-03-22 | Mistura para proteção de cultivo, e, processo para controlar fungos nocivos |
AU35195/99A AU3519599A (en) | 1998-03-24 | 1999-03-22 | Fungicide mixtures based on triple oxime ether derivatives and additional fungicides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19812759.6 | 1998-03-24 | ||
DE19812759 | 1998-03-24 |
Publications (1)
Publication Number | Publication Date |
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WO1999048369A1 true WO1999048369A1 (de) | 1999-09-30 |
Family
ID=7862020
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/001911 WO1999048369A1 (de) | 1998-03-24 | 1999-03-22 | Fungizide mischungen auf der basis von tripeloximetherderivaten und weiteren fungiziden |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1082010A1 (de) |
JP (1) | JP2002507554A (de) |
KR (1) | KR100560595B1 (de) |
CN (1) | CN1149925C (de) |
AU (1) | AU3519599A (de) |
BR (1) | BR9909017A (de) |
CA (1) | CA2323588A1 (de) |
CO (1) | CO5050309A1 (de) |
ID (1) | ID26490A (de) |
IL (1) | IL138166A0 (de) |
NZ (1) | NZ506727A (de) |
TW (1) | TW585740B (de) |
WO (1) | WO1999048369A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002049434A1 (de) * | 2000-12-18 | 2002-06-27 | Basf Aktiengesellschaft | Fungizide mischungen auf der basis von oximetherderivaten |
WO2006066810A2 (de) * | 2004-12-20 | 2006-06-29 | Basf Aktiengesellschaft | Verfahren zur bekämpfung von pilzkrankheiten bei leguminosen |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19547627A1 (de) * | 1995-09-21 | 1997-03-27 | Bayer Ag | Fungizide Wirkstoffkombinationen |
WO1997015552A1 (de) * | 1995-10-23 | 1997-05-01 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
-
1999
- 1999-03-22 JP JP2000537435A patent/JP2002507554A/ja active Pending
- 1999-03-22 CA CA002323588A patent/CA2323588A1/en not_active Abandoned
- 1999-03-22 NZ NZ506727A patent/NZ506727A/xx unknown
- 1999-03-22 WO PCT/EP1999/001911 patent/WO1999048369A1/de active IP Right Grant
- 1999-03-22 AU AU35195/99A patent/AU3519599A/en not_active Abandoned
- 1999-03-22 EP EP99916856A patent/EP1082010A1/de not_active Withdrawn
- 1999-03-22 ID IDW20001903A patent/ID26490A/id unknown
- 1999-03-22 CN CNB998043427A patent/CN1149925C/zh not_active Expired - Fee Related
- 1999-03-22 IL IL13816699A patent/IL138166A0/xx unknown
- 1999-03-22 KR KR1020007010572A patent/KR100560595B1/ko not_active IP Right Cessation
- 1999-03-22 BR BR9909017-1A patent/BR9909017A/pt not_active Application Discontinuation
- 1999-03-24 TW TW088104666A patent/TW585740B/zh not_active IP Right Cessation
- 1999-03-24 CO CO99017836A patent/CO5050309A1/es unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19547627A1 (de) * | 1995-09-21 | 1997-03-27 | Bayer Ag | Fungizide Wirkstoffkombinationen |
WO1997015552A1 (de) * | 1995-10-23 | 1997-05-01 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002049434A1 (de) * | 2000-12-18 | 2002-06-27 | Basf Aktiengesellschaft | Fungizide mischungen auf der basis von oximetherderivaten |
WO2006066810A2 (de) * | 2004-12-20 | 2006-06-29 | Basf Aktiengesellschaft | Verfahren zur bekämpfung von pilzkrankheiten bei leguminosen |
WO2006066810A3 (de) * | 2004-12-20 | 2006-09-21 | Basf Ag | Verfahren zur bekämpfung von pilzkrankheiten bei leguminosen |
EA012612B1 (ru) * | 2004-12-20 | 2009-10-30 | Басф Акциенгезельшафт | Способ борьбы с грибковыми заболеваниями бобовых культур |
Also Published As
Publication number | Publication date |
---|---|
NZ506727A (en) | 2002-08-28 |
CO5050309A1 (es) | 2001-06-27 |
CN1294492A (zh) | 2001-05-09 |
EP1082010A1 (de) | 2001-03-14 |
AU3519599A (en) | 1999-10-18 |
TW585740B (en) | 2004-05-01 |
ID26490A (id) | 2001-01-11 |
BR9909017A (pt) | 2000-12-05 |
KR100560595B1 (ko) | 2006-03-16 |
CN1149925C (zh) | 2004-05-19 |
IL138166A0 (en) | 2001-10-31 |
KR20010034648A (ko) | 2001-04-25 |
JP2002507554A (ja) | 2002-03-12 |
CA2323588A1 (en) | 1999-09-30 |
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