EP0865432A1 - Phenylacetic acid derivatives, process and intermediates for their preparation and their use as pesticides and/or fungicides - Google Patents
Phenylacetic acid derivatives, process and intermediates for their preparation and their use as pesticides and/or fungicidesInfo
- Publication number
- EP0865432A1 EP0865432A1 EP96941603A EP96941603A EP0865432A1 EP 0865432 A1 EP0865432 A1 EP 0865432A1 EP 96941603 A EP96941603 A EP 96941603A EP 96941603 A EP96941603 A EP 96941603A EP 0865432 A1 EP0865432 A1 EP 0865432A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- alkyl
- compounds
- hydrogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Definitions
- the present invention relates to phenylacetic acid derivatives of the formula I.
- R a , R 1 are hydrogen and alkyl
- R 2 cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
- R 3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;
- A is a 5- or 6-membered heteroaromatic ring
- R 4 substituted aryl
- R 5 hydrogen, optionally subst.
- the invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi. Phenylacetic acid derivatives for pest control are known from the literature [WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A
- the present invention was based on new compounds with improved activity as an object.
- the compounds I are obtainable in various ways according to methods known per se in the literature.
- L 1 in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
- the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.
- a base e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.
- the required hydroxyimine III is obtained, for example, by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
- L 2 in formula VI represents a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
- reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
- a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
- the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula v, where v is then converted to I with the nucleophilically substituted reagent VI.
- the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,
- a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,
- Q ⁇ in formula IXb stands for the anion of an acid, in particular an inorganic acid, for example.
- reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73f; Houben-Weyl, vol. E 14b, p. 369f and p. 385f.
- the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VII into a corresponding benzyloxyimine of the formula VIII, VIII being subsequently converted to I with the hydroxylamine IXa or its salt IXb.
- the reaction is carried out in a manner known per se in an inert organic solvent according to the in Houben-Weyl, vol. E 14b, p. 369f; Houben-Weyl, Vol. 10/1, pp. 1189f and Houben-Weyl, Vol. 10/4, pp. 73f or EP-A 513 580.
- reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488, DE-Anm. No. 42 28 867.3 methods described.
- the required carbonyl compound X is obtained, for example, by reacting a corresponding hydroxyiminocarbonyl compound VIa with a nucleophilically substituted reagent VI
- the reactions are carried out in a manner known per se in an inert organic solvent in accordance with the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55f, p. 73f, p. 180f and p. 217f; Houben-Weyl, vol. E 14b, pp. 307f and 369f, Houben-Weyl, vol. E 5, pp. 780f. 1.5
- the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyimino derivative VIa in the corresponding benzyloxyimino derivative of the formula V, V being subsequently converted to I with the nucleophilically substituted reagent VI as described above.
- the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl derivative of the formula XI into the benzyloxyimino derivative of the formula VIII and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.
- the corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII. 4.
- Compounds I in which R 3 is bonded to the skeleton via an oxygen atom are in some cases also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, pp. 826f; Aust. J. Chem. 27, 1341-9 (1974)].
- the corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII.
- Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the ⁇ -keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)).
- the corresponding carboxamides are obtained from the derivatives XV by amidation and are subsequently converted into the compounds I.
- compounds XVI are obtained by converting an ortho-halogen compound after metalation with oxalyl chloride into the corresponding keto acid chloride, which is then converted into the corresponding amide XVI with an amine (cf. J. Org.
- the compounds I in which Y denotes NR a are obtained , starting from the keto esters XV, by first derivatizing the keto function and converting the derivatives thus obtained to the amide using a corresponding amine (Houben-Weyl, Vol. E5, p. 941 f.)
- the compounds II are known (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 585 751, EP-A 400 417, EP-A 251 082) or can be prepared by the methods described therein become.
- Particularly preferred intermediates for the preparation of the compounds I are the compounds III '
- U 2 is oxygen, NOH or NOR 5 , where the radicals A, R 3 , R 4 and R 5 in general and in particular have the meaning given above.
- the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
- isomer mixtures are obtained in the synthesis, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (for example 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 ice isomers of the compounds I are generally preferred with regard to their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
- Halogen fluorine, chlorine, bromine and iodine
- Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 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-methylpentyl, 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 E
- Dialkylamino an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;
- Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
- Alkylsulfonyl straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-SO 2 -);
- Alkylaminocarbonyl alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
- Dialkylaminocarbonyl dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
- Alkylaminothiocarbonyl alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
- Dialkylaminothiocarbonyl dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
- 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, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluor
- Alkoxy straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via an oxygen atom (-O-), e.g.
- C 1 -C 6 alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbuty
- Halogenalkoxy 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, and where these groups are bonded to the skeleton via an oxygen atom;
- Alkylthio straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g.
- C 1 -C 6 alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2- Dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,
- Alkenyloxy straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via an oxygen atom (-O-);
- Alkenylthio straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via a sulfur atom (-S-);
- Alkenylamino an amino group which carries a straight-chain or branched alkenyl group having 2 to 6 carbon atoms as mentioned above;
- Alkenylcarbonyl straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
- Alkynyl straight-chain or branched alkynyl groups with 2 to 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, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propy
- Alkynyloxy straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via an oxygen atom (-O-);
- Alkynylthio straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a sulfur atom (-S-);
- Alkynylamino an amino group which carries a straight-chain or branched alkynyl group having 2 to 6 carbon atoms as mentioned above;
- Alkynylcarbonyl straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
- Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
- Cycloalkoxy monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-);
- Cycloalkylthio monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-); Cycloalkylamino: an amino group bearing a monocyclic alkyl group having 3 to 6 carbon ring members as mentioned above;
- Cycloalkenyl monocyclic alkenyl groups with 5 to 8 carbon ring members, e.g. Cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; Cycloalkenyloxy: monocyclic alkenyl groups with 5 to 8
- Aryl or aryloxy, arylthio, arylamino, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon residues which directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (arylamino) via a nitrogen atom or (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-SO 2 -) are bound to the structure, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl - and sulfonyl residues;
- Hetaryl or hetaryloxy, hetarylthio, hetarylamino, hetarylcarbonyl and hetarylsulfonyl 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 or one oxygen or one sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-O-) or (hetarylthio) a sulfur atom (-S-), (hetarylamino) via a nitrogen atom or (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a Sulfonyl group (-SO 2 -) are bound to the skeleton, for example
- 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-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one 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-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadi azol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,
- 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 bound via nitrogen containing one to four nitrogen atoms.
- benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one
- Nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-the-n-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, or the corresponding oxy, thio, amino, carbonyl or sulfonyl groups.
- cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 - Alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C
- substituted by conventional groups is intended to express that the radicals in question can be partially or completely halogenated and / or can carry one to three of the following substituents: cyano, nitro, hydroxy, amino, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, di-C 1 -C 4 - alkylamino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, phenyl, phenoxy, benzyl and benzyloxy, and / or a C 3 -C 5 alkylene, C 2 -C 4 alkyleneoxy bonded to two adjacent atoms , C 1 -C 4 -Oxyalkylenoxy, and / or a group C (
- 5- or 6-membered heteroaromatic rings in the definition of A are to be understood in particular as the following groups A-1 to A-88.
- the positions marked with # mark the bond to the rest of the molecule.
- the nitrogen atoms the 5-ring heteroaromatics with free valences can carry hydrogen or C 1 -C 6 alkyl in this position.
- X is NO 3 and Y is NR a and R a is hydrogen or methyl.
- X is NO 3 and Y is NR a and R 1 is hydrogen or methyl.
- X is NO 3 and Y is NR a and R a is hydrogen and R 1 is
- CHCH 3 and Y means oxygen.
- compounds of the formula I are preferred in which X is CHCH 2 CH 3 and Y is oxygen.
- R 2 is halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, in particular fluorine, chlorine, methyl and methoxy.
- R 3 represents one of the following substituents: hydrogen, hydroxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 - C 4 alkylthio and C 3 -C 6 cycloalkyl, in particular hydrogen, hydroxy, chlorine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, methylthio and cyclopropyl.
- R 3 represents one of the following substituents: hydrogen, halogen,
- R 3 represents hydrogen or C 1 -C 4 alkyl, in particular methyl.
- R 4 represents substituted phenyl.
- R 4 represents phenyl substituted by customary groups.
- R 4 is phenyl which carries at least one of the following substituents: cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 - Alkoxy, especially fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy and ethoxy.
- R 4 is phenyl which carries at least one trifluoromethyl group.
- A represents one of the following radicals: A-2, A-6, A-10, A-11, A-12, A-17, A-18, A-20, A- 21, A-27, A-29, A-33, A-35, A-39, A-43, A-44, A-45, A-46, A-49, A-50, A-51, A-52, A-55, A-59, A-60, A-61, A-62, A-63, A-65, A-67, A-68, A-69, A-71, A- 72, A-76, A-78, A-79, A-80, A-81 and A-83.
- A represents one of the following radicals: A-2, A-20, A-21, A-39, A-55, A-59, A-67, A-68, A- 69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-20.
- A represents one of the following radicals: A-10, A-II, A-12, A-27, A-29, A-43, A-44, A-45, A- 46, A-63 and A-65, particularly preferably A-44.
- A represents one of the following radicals: A-17, A-18, A-33, A-35, A-49, A-50, A-51, A-52, A- 60, A-61 and A-62, particularly preferably A-50.
- compounds I are preferred in which A is A-2, A-20, A-21 and A-39, particularly preferably A-20.
- compounds I are preferred in which A is A-10, A-II and A-12, particularly preferably A-10.
- compounds I are preferred in which A is A-17 and A-18, particularly preferably A-18.
- compounds I are preferred in which A is A-27, A-29, A-33 and A-35, particularly preferably A-33 and A-35.
- compounds I are preferred in which A is A-43, A-44, A-45 and A-46, particularly preferably A-44 and A-46.
- compounds I are preferred in which A is A-49, A-50, A-51 and A-52, particularly preferably A-50 and A-52.
- compounds I are preferred in which A is A-55, A-59, A-60, A-61, A-62, A-63 and A-65, particularly preferably A-60, A-62 and A- 65, stands.
- compounds I are preferred in which A is A-67, A-68, A-69, A-71 and A-72, particularly preferably A-67 and A-68.
- compounds I are preferred in which A is A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-79.
- R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, di- C 1 -C 4 alkylamino-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl.
- R 5 represents one of the following substituents: hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, in particular hydrogen, methyl, ethyl, n-propyl, iso-propyl and methoxyethyl.
- R 5 represents one of the following substituents: hydrogen and C 1 -C 4 -alkyl, in particular methyl, ethyl, n-propyl and isopropyl, particularly preferably methyl.
- R 5 is C 3 -C 6 alkenyl and C 3 -C 6 haloalkenyl.
- R 5 is C 3 -C 6 alkynyl and C 3 -C 6 haloalkynyl.
- the compounds I are suitable as fungicides.
- the compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides. They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans and pumpkin family, as well as on the seeds of these plants.
- Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia types on cereals, Rhizoctonia and rice species Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Cereospora arachidicola on peanuts, Pseudocrichosidesella on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viti
- the compounds I are also suitable for combating
- Harmful fungi in material protection e.g. wood, paper, fibers or fabric
- material protection e.g. wood, paper, fibers or fabric
- the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
- formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compounds according to the invention.
- the formulations are prepared in a known manner for example, by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
- auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g.
- Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
- Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates)
- Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
- the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
- the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
- amounts of active ingredient generally range from 0.001 to 0.1 g, preferably 0.01 to 0.05 g required per kilogram of seed.
- the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates are in
- Material protection for example 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
- the agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
- Sulfur, dithiocarbamates and their derivatives such as iron, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, Tetramethylthiuramdisulfide, ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), ammonia complex of Zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6
- Strobilurins such as methyl-E-methoxyimino- [ ⁇ - (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino- [ ⁇ - (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [ ⁇ - (2,5-dimethylphenoxy) -o-tolyl] acetamide.
- Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 -cyclopropyl-pyrimidin-2-yl) aniline.
- Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile.
- Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide.
- the compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, storage protection and veterinary sectors.
- the harmful insects from the order of the butterflies include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobisturaumumone, Cheimatobisturaumumone Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,
- Diptera From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropucitae, Cordylobia anthropucaga, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropacea, brassylaciaacropaceacita, brassylaciaacropia , Fannia canicularis, Gasterophilus intestinalis,
- Tipula oleracea Tipula paludosa.
- Thrips for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
- From the order of the hymenoptera for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invieta.
- Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leueopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensidata, Nezara pratensidata, Sol .
- bugs Heteroptera
- Acrosternum hilare Blissus leueopterus
- Cyrtopeltis notatus Dysdercus cingulatus
- Dysdercus intermedius Eurygaster integriceps
- Euschistus impictiventris Leptoglossus phyllopus
- Lygus lineolaris Lygus pratensidata
- Nezara pratensidata Sol .
- suckers for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui,
- Termes natalensis From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinataus, Melanopladusana, Melanopladipana Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
- Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexican
- arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata Otobius megnini, Paratetranyehus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sar
- Amblyomma americanum such as Amblyomma
- root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g.
- root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g.
- the active ingredients as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied.
- the application forms depend entirely on the purposes; she should ensure the finest possible distribution of the active compounds according to the invention in any case.
- the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
- active ingredients are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
- the application rate of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
- emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent, by means of wetting agents,
- Adhesives, dispersants or emulsifiers are homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
- Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
- the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
- Parts of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil are present (active ingredient content 9% by weight).
- V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenalphasulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and in grind in a hammer mill (active ingredient content 80% by weight).
- Spray liquor containing 0.1% by weight of the active ingredient.
- Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
- Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
- mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite
- Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
- Example 1 Synthesis of (E, E, E) -2 - [[[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] - ⁇ - (methoxyimino) phenylacetic acid methyl ester
- the active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight.
- % Emulphor® EL Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration.
- Emulsifier was prepared, sprayed and dusted with spores of powdery mildew (Erysiphe graminis var. Tritici) 24 hours after the spray coating had dried on.
- the test plants were then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area. In this test, those with 250 ppm of compounds no.
- Leaves of potted vines of the "Müller-Thurgau" variety were sprayed with an aqueous spray mixture which had been prepared with a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier.
- the plants were divided in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
- the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C.
- the active ingredients were:
- b. as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) processed and with the desired concentration with acetone in the case of a. or with water in the case of b. diluted.
- Nekanil® LN Litensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
- Emulphor® EL Emulphor® EL
- Potted bush beans with a fully developed pair of leaves were sprayed to runoff point in the spray booth with the aqueous active ingredient solution.
- the plants were guided over a running rail to the turntable of the spray booth and sprayed on all sides with 3 differently oriented nozzles when 30 cm 3 of active ingredient solution was applied.
- the spraying process took about 20 seconds.
- the plants were heavily infested with mites and abundant oviposition. The effect was assessed after 5 days using a binocular. It was determined whether all stages were recorded evenly. The plants were under normal greenhouse conditions during this time. In this experiment, substance 1.17 from the table showed an activity threshold of 200 ppm.
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Abstract
The invention relates to phenylacetic acid derivatives of the formula (I), in which the substituents and the index have the following meaning: X is NOCH3, CHOCH3, CHCH3 and CHCH2CH3; Y is NRa and O; Ra, R1 are hydrogen and alkyl; R2 is cyano, nitro, halogen, alkyl, alkyl halide and alkoxy; m is 0, 1 or 2; R3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, alkyl halide, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino; A is a 5 or 6 membered hetero-aromatic ring; R4 is a substituted aryl; R5 is hydrogen, optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl. The invention also relates to the salts of said derivatives, a process and intermediates for the preparation and use thereof.
Description
PHENYLESSIGSAUREDERIVATE, VERFAHREN UND ZWISCHENPRODUKTE ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS PESTIZIDE UND/ODER FUNGIZIDE. Beschreibung PHENYL ACETIC DERIVATIVES, METHODS AND INTERMEDIATE PRODUCTS FOR THE PRODUCTION THEREOF AND THEIR USE AS PESTICIDES AND / OR FUNGICIDES. description
Die vorliegende Erfindung betriff t Phenylessigsäurederivate der Formel I The present invention relates to phenylacetic acid derivatives of the formula I.
in der die Substituenten und der Index die folgende Bedeutung haben: in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3, CHCH3 und CHCH2CH3; X NOCH 3 , CHOCH 3 , CHCH 3 and CHCH 2 CH 3 ;
Y NRa und O; Y NR a and O;
Ra, R1 Wasserstoff und Alkyl; R a , R 1 are hydrogen and alkyl;
R2 Cyano, Nitro, Halogen, Alkyl, Halogenalkyl und Alkoxy; m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht; R 2 cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Hydroxy, Amino, Cyano, Halogen, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Alkylthio, Alkylamino und Dialkylamino; R 3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;
A ein 5- oder 6-gliedriger heteroaromatischer Ring; A is a 5- or 6-membered heteroaromatic ring;
R4 substituiertes Aryl; R 4 substituted aryl;
R5 Wasserstoff, ggf. subst. Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Heterocyclyl, Aryl und Hetaryl, sowie deren Salze.
Außerdem betrifft die Erfindung Verfahren und Zwischenprodukte zur Herstellung dieser Verbindungen sowie sie enthaltende Mittel zur Bekämpfung tierischer Schädlinge und Schadpilze. Aus der Literatur sind Phenylessigsäurederivate zur Schädlingsbekämpfung bekannt [WO-A 95/18,789, WO-A 95/21,153, WO-A R 5 hydrogen, optionally subst. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl, and their salts. The invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi. Phenylacetic acid derivatives for pest control are known from the literature [WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A
95/21,154]. 95 / 21,154].
Der vorliegenden Erfindung lagen neue Verbindungen mit verbesserter Wirkung als Aufgabe zugrunde. The present invention was based on new compounds with improved activity as an object.
Demgemäß wurden die eingangs definierten Phenylessigsäurederivate I gefunden. Außerdem wurden Verfahren und Zwischenprodukte zu ihrer Herstellung sowie sie enthaltende Mittel zur Bekämpfung von tierischen Schädlingen und Schadpilzen und ihre Verwendung in diesem Sinne gefunden. We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. In addition, processes and intermediates for their preparation and compositions containing them for controlling animal pests and harmful fungi and their use were found in this sense.
Die Verbindungen I sind auf verschiedenen wegen nach an sich in der Literatur bekannten Verfahren erhältlich. The compounds I are obtainable in various ways according to methods known per se in the literature.
Grundsätzlich ist es bei der Synthese der Verbindungen I unerheblich, ob zunächst die Gruppierung -C(X)-COYR1 oder die Gruppierung -CH2ON=C(R3)-C(AR4)=NOR5 aufgebaut wird. Der Aufbau der Gruppierung -C(X)-COYR1 ist beispielsweise aus der eingangs zitierten Literatur sowie aus EP-A 242 070, EP-A 254 426, EP-A 370 629, EP-A 422 597, EP-A 463 488, EP-A 472 300, EP-A 513 580, EP-A 656 352, EP-A 398 692 und PCT/EP 95/02,013 bekannt. In the synthesis of the compounds I, it is fundamentally irrelevant whether the group -C (X) -COYR 1 or the group -CH 2 ON = C (R 3 ) -C (AR 4 ) = NOR 5 is built up first. The structure of the grouping -C (X) -COYR 1 is, for example, from the literature cited at the beginning and from EP-A 242 070, EP-A 254 426, EP-A 370 629, EP-A 422 597, EP-A 463 488 , EP-A 472 300, EP-A 513 580, EP-A 656 352, EP-A 398 692 and PCT / EP 95 / 02,013.
Die Art der Synthese der Gruppierung -CH2ON=C (R3) -C (AR4)=NOR5 richtet sich im wesentlichen nach der Art des Substituenten R3. The type of synthesis of the grouping -CH 2 ON = C (R 3 ) -C (AR 4 ) = NOR 5 depends essentially on the type of the substituent R 3 .
1. Für den Fall, daß R3 nicht Halogen bedeutet, geht man beim Aufbau der Gruppierung -CH2ON=C(R3) -C (AR4) =NOR5 im allgemeinen so vor, daß man ein Benzylderivat der Formel II mit einem Hydroxyimin der Formel III umsetzt.
() 1. In the event that R 3 does not mean halogen, the structure of the grouping -CH 2 ON = C (R 3 ) -C (AR 4 ) = NOR 5 is generally carried out in such a way that a benzyl derivative of the formula II reacted with a hydroxyimine of the formula III. ()
L1 in der Formel II steht für eine nukleophil austauschbare Abgangsgruppe, z.B. Halogen oder Sulfonatgruppen, vorzugsweise Chlor, Brom, Iod, Mesylat, Tosylat oder Triflat. L 1 in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel in Gegenwart einer Base, z.B. Natriumhydrid, Kaliumhydroxid, Kaliumcarbonat und Triethylamin gemäß den in Houben-Weyl, Bd. E 14b, S. 370f und Houben-Weyl, Bd. 10/1, S. 1189f beschriebenen Methoden. The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370f and Houben-Weyl, vol. 10/1, p. 1189f.
Das benötigte Hydroxyimin III erhält man beispielsweise durch Umsetzung eines entsprechenden Dihydroxyimins IV mit einem nukleophil substituierten Reagens VI The required hydroxyimine III is obtained, for example, by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
L2 in der Formel VI steht für eine nukleophil austauschbare Abgangsgruppe, z.B. Halogen oder Sulfonatgruppen, vorzugsweise Chlor, Brom, Iod, Mesylat, Tosylat oder Triflat. L 2 in formula VI represents a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel in Gegenwart einer Base, z.B. Kaliumcarbonat, Kaliumhydroxid, Natriumhydrid, Pyridin und Triethylamin gemäß den in Houben-Weyl, Bd. E 14b, The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
S. 307f, S. 370f und S. 385f; Houben-Weyl, Bd. 10/4, S. 55f, S. 180f und S. 217f; Houben-Weyl, Bd. E 5, S. 780f, beschriebenen Methoden.
1.1 Alternativ können die Verbindungen I auch dadurch erhalten werden, daß das Benzylderivat II zunächst mit dem Dihydroxyiminoderivat IV in ein entsprechendes Benzyloxim der Formel v umgesetzt wird, wobei v anschließend mit dem nukleophil substituierten Reagens VI zu I umgesetzt wird. P. 307f, p. 370f and p. 385f; Houben-Weyl, Vol. 10/4, p. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f. 1.1 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula v, where v is then converted to I with the nucleophilically substituted reagent VI.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel in Gegenwart einer Base z.B. Kaliumcarbonat, Kaliumhydroxid, Natriumhydrid, Pyridin und Triethylamin gemäß den in Houben-Weyl, Bd. 10/1, The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1,
S. 1189f; Houben-Weyl, Bd. E 14b, S. 307f, S. 370f und Pp. 1189f; Houben-Weyl, vol. E 14b, p. 307f, p. 370f and
S. 385f; Houben-Weyl, Bd. 10/4, S. 55f, S. 180f und S. 217f; Houben-Weyl, Bd. E 5, S. 780f, beschriebenen Methoden. P. 385f; Houben-Weyl, Vol. 10/4, p. 55f, p. 180f and p. 217f; Houben-Weyl, vol. E 5, p. 780f.
1.2 Analog ist es ebenfalls möglich, das benötigte Hydroxyimin der Formel III aus einem Carbonylhydroxyimin VII durch Umsetzung mit einem Hydroxylamin IXa oder seinem Salz IXb herzustellen.
1.2 Analogously, it is also possible to prepare the required hydroxyimine of the formula III from a carbonylhydroxyimine VII by reaction with a hydroxylamine IXa or its salt IXb.
QӨ in der Formel IXb steht für das Anion einer Säure , insbesondere einer anorganischen Säure , z .B . Halogenid wieQ Ө in formula IXb stands for the anion of an acid, in particular an inorganic acid, for example. Halide like
Chlorid. Chloride.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in EP-A 513 580; Houben-Weyl, Bd. 10/4, S. 73f; Houben-Weyl, Bd. E 14b, S. 369f und S. 385f beschriebenen Methoden. The reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73f; Houben-Weyl, vol. E 14b, p. 369f and p. 385f.
1.3 Alternativ können die Verbindungen I auch dadurch erhalten werden, daß das Benzylderivat II zunächst mit dem Carbonylhydroxyiminoderivat VII in ein entsprechendes Benzyloxyimin der Formel VIII umgesetzt wird, wobei VIII anschließend mit dem Hydroxylamin IXa bzw. dessen Salz IXb zu I umgesetzt wird. 1.3 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VII into a corresponding benzyloxyimine of the formula VIII, VIII being subsequently converted to I with the hydroxylamine IXa or its salt IXb.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in Houben-Weyl, Bd. E 14b, S. 369f; Houben-Weyl, Bd. 10/1, S. 1189f und
Houben-Weyl, Bd. 10/4, S. 73f oder EP-A 513 580 beschriebenen Methoden. The reaction is carried out in a manner known per se in an inert organic solvent according to the in Houben-Weyl, vol. E 14b, p. 369f; Houben-Weyl, Vol. 10/1, pp. 1189f and Houben-Weyl, Vol. 10/4, pp. 73f or EP-A 513 580.
1.4 Eine weitere Möglichkeit zur Herstellung der Verbindungen I ist die Umsetzung des Benzylderivats II mit N-Hydroxyphthalimid und nachfolgender Hydrazinolyse zum Benzylhydroxylamin Ha und die weitere Umsetzung von Ha mit einer Carbonylverbindung X. 1.4 A further possibility for the preparation of the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to give the benzylhydroxylamine Ha and the further reaction of Ha with a carbonyl compound X.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in EP-A 463 488, DE-Anm. Nr. 42 28 867.3 beschriebenen Methoden. The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488, DE-Anm. No. 42 28 867.3 methods described.
Die benötigte CarbonylVerbindung X erhält man beispielsweise durch Umsetzung einer entsprechenden HydroxyiminocarbonylVerbindung Vlla mit einem nukleophil substituierten Reagens VI
The required carbonyl compound X is obtained, for example, by reacting a corresponding hydroxyiminocarbonyl compound VIa with a nucleophilically substituted reagent VI
oder durch Umsetzung einer entsprechenden Dicarbonylverbindung XI mit einem Hydroxylamin IXa oder dessen Salz IXb
or by reacting a corresponding dicarbonyl compound XI with a hydroxylamine IXa or its salt IXb
Die Umsetzungen erfolgen in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in EP-A 513 580, Houben-Weyl, Bd. 10/4, S. 55f, S. 73f, S. 180f und S. 217f; Houben-Weyl, Bd. E 14b, S. 307f und 369f, Houben-Weyl, Bd. E 5, S. 780f beschriebenen Methoden. 1.5 Entsprechend können die Verbindungen I auch dadurch erhalten werden, daß das Benzylhydroxylamin Ha zunächst mit dem Hydroxyiminoderivat Vlla in das entsprechende Benzyloxyiminoderivat der Formel V umgesetzt wird, wobei V anschließend mit dem nukleophil substituierten Reagens VI wie vorstehend beschrieben zu I umgesetzt wird. The reactions are carried out in a manner known per se in an inert organic solvent in accordance with the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55f, p. 73f, p. 180f and p. 217f; Houben-Weyl, vol. E 14b, pp. 307f and 369f, Houben-Weyl, vol. E 5, pp. 780f. 1.5 Correspondingly, the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyimino derivative VIa in the corresponding benzyloxyimino derivative of the formula V, V being subsequently converted to I with the nucleophilically substituted reagent VI as described above.
1.6 Analog können die Verbindungen I ebenfalls dadurch hergestellt werden, daß das Benzylhydroxylamin Ha zunächst mit dem Dicarbonylderivat der Formel XI in das Benzyloxyiminoderivat der Formel VIII überführt wird und VIII anschließend mit dem Hydroxylamin IXa oder dessen Salz IXb wie vorstehend beschrieben zu I umgesetzt wird.
1.6 Analogously, the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl derivative of the formula XI into the benzyloxyimino derivative of the formula VIII and then reacting VIII with the hydroxylamine IXa or its salt IXb to give I as described above.
2. Verbindungen I, in denen R3 für ein Halogenatom steht, erhält man aus den entsprechenden Vorstufen, in denen der betreffende Rest für eine Hydroxygruppe steht, nach an sich bekannten Methoden [vgl. Houben Weyl, Vol. E5, S. 631; J. Org. Chem. 36, 233 (1977); J. Org. Chem. 57, 3245 (1992)]. Vorzugsweise werden die entsprechenden Umsetzungen zum Halogenderivat auf den Stufen I und VIII vorgenommen. 2. Compounds I in which R 3 represents a halogen atom are obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, p. 631; J. Org. Chem. 36, 233 (1977); J. Org. Chem. 57, 3245 (1992)]. The corresponding reactions to the halogen derivative are preferably carried out at stages I and VIII.
3. Verbindungen I, in denen R3 über ein O-, S- oder N-Atom an das Gerüst gebunden ist, erhält man aus den entsprechenden Vorstufen, in denen der betreffende Rest für ein Halogenatom steht, nach an sich bekannten Methoden [vgl. Houben Weyl, Vol. E5, S. 826f. und 1280f; J. Org. Chem. 36, 233 (1977);3. Compounds I in which R 3 is bonded to the skeleton via an O, S or N atom are obtained from the corresponding precursors in which the radical in question represents a halogen atom by methods known per se [cf. . Houben Weyl, Vol. E5, pp. 826f. and 1280f; J. Org. Chem. 36, 233 (1977);
J. Org. Chem. 46, 3623 (1981)]. Vorzugsweise werden die entsprechenden Umsetzungen der Halogenderivate auf den Stufen I und VIII vorgenommen. 4. Verbindungen I, in denen R3 über ein Sauerstoffatom an das Gerüst gebunden ist, erhält man z.T. auch aus den entsprechenden Vorstufen, in denen der betreffende Rest für eine Hydroxygruppe steht, nach an sich bekannten Methoden [vgl. Houben Weyl, Vol. E5, S. 826f; Aust. J. Chem. 27, 1341-9 (1974)]. Vorzugsweise werden die entsprechenden Umsetzungen der Halogenderivate auf den Stufen I und VIII vorgenommen. J. Org. Chem. 46, 3623 (1981)]. The corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII. 4. Compounds I in which R 3 is bonded to the skeleton via an oxygen atom are in some cases also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se [cf. Houben Weyl, Vol. E5, pp. 826f; Aust. J. Chem. 27, 1341-9 (1974)]. The corresponding reactions of the halogen derivatives are preferably carried out at stages I and VIII.
5. Verbindungen I, in denen Y Sauerstoff bedeutet und R3 nicht für Halogen steht, erhält man bevorzugt dadurch, daß man eine Verbindung X gemäß den in EP-A 493 711 beschriebenen5. Compounds I in which Y is oxygen and R 3 is not halogen are preferably obtained by compound X according to those described in EP-A 493 711
Methoden mit einem Lacton XII zunächst in die entsprechende Benzoesäure XIII überführt und XIII über die entsprechenden Halogenide in die Cyanocarbonsäuren XIV überführt, welche im Wege der Pinner-Reaktion (Angew. Chem. 94, 1 (1982)) in die α-Ketoester XV und anschließend in die Derivate I überführt werden (vgl. EP-A 348 766, DE-A 37 05 389, EP-A 178 826, DE-A 36 23 921).
Methods with a lactone XII first converted into the corresponding benzoic acid XIII and XIII via the corresponding halides into the cyanocarboxylic acids XIV, which by way of the Pinner reaction (Angew. Chem. 94, 1 (1982)) into the α-keto esters XV and are subsequently converted into derivatives I (cf. EP-A 348 766, DE-A 37 05 389, EP-A 178 826, DE-A 36 23 921).
Verbindungen I, in denen R1 Wasserstoff bedeutet, erhält man nach diesem Verfahren durch Verseifung der Ester XV und anschließende Umsetzung zu I. Compounds I in which R 1 is hydrogen are obtained by this process by saponification of the esters XV and subsequent conversion to I.
Verbindungen I, in denen Y NRa bedeutet und R3 nicht für Halogen steht, erhält man bevorzugt dadurch, daß man eine Verbindung X gemäß den in EP-A 493 711 beschriebenen Methoden mit einem Lacton XII zunächst in die entsprechende Benzoesäure XIII überführt und XIII über die entsprechenden Compounds I in which Y is NR a and R 3 is not halogen are preferably obtained by converting a compound X according to the methods described in EP-A 493 711 with a lactone XII into the corresponding benzoic acid XIII and XIII about the corresponding
Halogenide in die Cyanocarbonsäuren XIV überführt, welche dann im Wege der Pinner-Reaktion (Angew. Chem. 94, 1 (1982)) in die α-Ketoester XV überführt werden. Aus den Derivaten XV erhält man durch Amidierung die entsprechenden Carbonsäureamide, die anschließend in die Verbindungen I überführt werden.
Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the α-keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)). The corresponding carboxamides are obtained from the derivatives XV by amidation and are subsequently converted into the compounds I.
7. In Abwandlung des unter 6. beschriebenen Verfahrens kann man auch direkt aus den Carbonsäurehalogeniden durch Umsetzung mit Isocyanaten und anschließender Hydrolyse direkt die Verbindungen XVI erhalten, in denen Ra Wasserstoff bedeutet (EP-A 547 825). 7. In a modification of the process described under 6, the compounds XVI in which R a is hydrogen can also be obtained directly from the carboxylic acid halides by reaction with isocyanates and subsequent hydrolysis (EP-A 547 825).
8. In einer weiteren Variante erhält man Verbindungen XVI dadurch, daß man eine ortho-Halogenverbindung nach Metallierung mit Oxalylchlorid in das entsprechende Ketosäurechlorid überführt, welches anschließend mit einem Amin in das entsprechende Amid XVI überführt wird (vgl. J. Org. 8. In a further variant, compounds XVI are obtained by converting an ortho-halogen compound after metalation with oxalyl chloride into the corresponding keto acid chloride, which is then converted into the corresponding amide XVI with an amine (cf. J. Org.
Chem. 46, 212 f (1981); DE-A 40 42 280; Houben Weyl, Bd. E5, S. 972 f). Chem. 46, 212f (1981); DE-A 40 42 280; Houben Weyl, Vol. E5, p. 972 f).
9. In einer weiteren Variante erhält man die Verbindungen I in denen Y NRa bedeutet, ausgehend von den Ketoestern XV, indem man zunächst die Ketofunktion derivatisiert und die so erhaltenen Derivate mit einem entsprechenden Amin in das Amid überführt (Houben-Weyl, Bd. E5, S. 941 f.) 9. In a further variant, the compounds I in which Y denotes NR a are obtained , starting from the keto esters XV, by first derivatizing the keto function and converting the derivatives thus obtained to the amide using a corresponding amine (Houben-Weyl, Vol. E5, p. 941 f.)
Die Verbindungen II sind bekannt (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 585 751, EP-A 400 417, EP-A 251 082) oder können nach den dort beschriebenen Methoden hergestellt werden.
Besonders bevorzugte Zwischenprodukte zur Herstellung der Verbindungen I sind die Verbindungen III'
The compounds II are known (EP-A 513 580, EP-A 477 631, EP-A 463 488, EP-A 585 751, EP-A 400 417, EP-A 251 082) or can be prepared by the methods described therein become. Particularly preferred intermediates for the preparation of the compounds I are the compounds III '
in denen die Substituenten die folgende Bedeutung haben: in which the substituents have the following meaning:
U1 Sauerstoff oder NOH, U 1 oxygen or NOH,
U2 Sauerstoff, NOH oder NOR5, wobei die Reste A, R3, R4 und R5 im allgemeinen und im besonderen die vorstehend gegebene Bedeutung haben. U 2 is oxygen, NOH or NOR 5 , where the radicals A, R 3 , R 4 and R 5 in general and in particular have the meaning given above.
Desweiteren werden zur Herstellung der Verbidungen I Zwischenprodukte der allgemeinen Formel V bevorzugt, Furthermore, intermediates of the general formula V are preferred for the preparation of the compounds I
in denen U für Sauerstoff oder NOH steht und die Reste A, X, Y, R1, R2, R3 und R4 sowie der Index im allgemeinen und im besonderen die vorstehend gegebene Bedeutung haben. in which U represents oxygen or NOH and the radicals A, X, Y, R 1 , R 2 , R 3 and R 4 and the index in general and in particular have the meaning given above.
Die Verbindungen I können bei der Herstellung aufgrund ihrer C=C und C=N Doppelbindungen als E/Z-Isomerengemische anfallen, die z.B. durch Kristallisation oder Chromatographie in üblicher Weise in die EinzelVerbindungen getrennt werden können. Due to their C = C and C = N double bonds, the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
Sofern bei der Synthese Isomerengemische anfallen, ist im allgemeinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise während der Aufbereitung für die Anwendung oder bei der Anwendung (z.B. unter Licht-, Säure- oder Baseneinwirkung) ineinander umwandeln können. Entsprechende Umwandlungen können auch nach der Anwendung, beispielsweise bei der Behandlung von Pflanzen in der behandelten Pflanze oder im zu bekämpfenden Schadpilz oder tierischen Schädling erfolgen.
In Bezug auf die C=X Doppelbindung werden hinsichtlich ihrer Wirksamkeit die E-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf die -OCH3 bzw. die -CH3 Gruppe im Verhältnis zur (O=C)YR1 Gruppe). If isomer mixtures are obtained in the synthesis, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (for example 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. With regard to the C = X double bond, 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 (O = C) YR 1 group).
In Bezug auf die -C(R3)=NOCH2- Doppelbindung werden hinsichtlich ihrer Wirksamkeit im allgemeinen die eis-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf den Rest R3 im Verhältnis zur -OCH2- Gruppe). With regard to the -C (R 3 ) = NOCH 2 double bond, the ice isomers of the compounds I are generally preferred with regard to their activity (configuration based on the radical R 3 in relation to the -OCH 2 group).
Die Konfiguration der -C(AR4)=NOR5 Doppelbindung hat im allgemeinen einen geringen Einfluß auf die Wirksamkeit der Verbindungen. Sofern eine Beeinflussung der Wirksamkeit auftritt, sind üblicherweise die cis-Isomere (Konfiguration bezogen auf die Gruppe AR4 im Verhältnis zu OR5) bevorzugt. The configuration of the -C (AR 4 ) = NOR 5 double bond generally has little influence on the activity of the compounds. If the effectiveness is influenced, the cis isomers (configuration based on the group AR 4 in relation to OR 5 ) are usually preferred.
Bei den eingangs angegebenen Definitionen der Verbindungen I wurden Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Gruppen stehen: In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
Halogen: Fluor, Chlor, Brom und Jod; Halogen: fluorine, chlorine, bromine and iodine;
Alkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 4, 6 oder 10 Kohlenstoffatomen, z.B. C1-C6-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methyl-propyl, 2-Methylpropyl, 1,1-Dimethylethyl, Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Di-methylpropyl, 1-Ethylpropyl, Hexyl, 1,1-Dimethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 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, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl und 1-Ethyl-2-methylpropyl; Alkylamino: eine Aminogruppe, welche eine geradkettige oder verzweigte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen wie vorstehend genannt trägt; Alkyl: straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 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-methylpentyl, 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 Ethyl butyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; Alkylamino: an amino group which carries a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;
Dialkylamino: eine Aminogruppe, welche zwei voneinander unabhängige, geradkettige oder verzweigte Alkylgruppen mit jeweils 1 bis 6 Kohlenstoffatomen wie vorstehend genannt, trägt; Dialkylamino: an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;
Alkylcarbonyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 10 Kohlenstoffatomen, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind;
Alkylsulfonyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 oder 10 Kohlenstoffatomen, welche über eine Sulfonylgruppe (-SO2-) an das Gerüst gebunden sind; Alkylsulfoxyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, welche über eine Sulfoxylgruppe (-S(=O)-) an das Gerüst gebunden sind; Alkylaminocarbonyl: Alkylaminogruppen mit 1 bis 6 Kohlenstoffatomen wie vorstehend genannt, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind; Alkylcarbonyl: straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-); Alkylsulfonyl: straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-SO 2 -); Alkylsulfoxyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via a sulfoxyl group (-S (= O) -); Alkylaminocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
Dialkylaminocarbonyl: Dialkylaminogruppen mit jeweils 1 bis 6 Kohlenstoffatomen pro Alkylrest wie vorstehend genannt, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind; Dialkylaminocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-);
Alkylaminothiocarbonyl: Alkylaminogruppen mit 1 bis 6 Kohlenstoffatomen wie vorstehend genannt, welche über eine Thiocarbonylgruppe (-CS-) an das Gerüst gebunden sind; Alkylaminothiocarbonyl: alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
Dialkylaminothiocarbonyl: Dialkylaminogruppen mit jeweils 1 bis 6 Kohlenstoffatomen pro Alkylrest wie vorstehend genannt, welche über eine Thiocarbonylgruppe (-CS-) an das Gerüst gebunden sind; Halogenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. C1-C2-Halogenalkyl wie Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor2,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl und Pentafluorethyl; Dialkylaminothiocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-); 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, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro -2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Alkoxy: geradkettige oder verzweigte Alkylgruppen mit 1 bis 4 oder 6 Kohlenstoffatomen wie vorstehend genannt, welche über ein Sauerstoffatom (-O-) an das Gerüst gebunden sind, z.B. Alkoxy: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via an oxygen atom (-O-), e.g.
C1-C6-Alkoxy wie Methyloxy, Ethyloxy, Propyloxy, 1-Methylethyloxy, Butyloxy, 1-Methyl-propyloxy, 2-Methylpropyloxy, 1,1-Dimethylethyloxy, Pentyloxy, 1-Methylbutyloxy, 2-Methylbutyloxy, 3-Methylbutyloxy, 2,2-Di-methylpropyloxy, 1-Ethylpropyloxy, Hexyloxy, 1,1-Dimethylpropyloxy, 1, 2-Dimethylpropyloxy, 1-Methylpentyloxy, 2-Methylpentyloxy, 3-Methylpentyloxy, 4-Methylpentyloxy, 1,1-Dimethylbutyloxy, 1,2-Dimethylbutyloxy, 1,3-Dimethylbutyloxy, 2,2-Dimethylbutyloxy, 2,3-Dimethylbutyloxy, 3,3-Dimethylbutyloxy, 1-Ethyl-butyloxy, 2-Ethylbutyloxy, 1,1,2-Trime
thylpropyloxy, 1,2,2-Trimethylpropyloxy, 1-Ethyl-1-methylpropyl oxy und 1-Ethyl-2-methylpropyloxy; C 1 -C 6 alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1, 2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trime thylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyl oxy and 1-ethyl-2-methylpropyloxy;
Alkoxycarbonyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, welche über eine Oxycarbonylgruppe (-OC(=O)-) an das Gerüst gebunden sind; Alkoxycarbonyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via an oxycarbonyl group (-OC (= O) -);
Halogenalkoxy: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, und wobei diese Gruppen über ein Sauerstoffatom an das Gerüst gebunden sind; Halogenalkoxy: 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, and where these groups are bonded to the skeleton via an oxygen atom;
Alkylthio: geradkettige oder verzweigte Alkylgruppen mit 1 bis 4 oder 6 Kohlenstoffatomen wie vorstehend genannt, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind, z.B. Alkylthio: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g.
C1-C6-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methylpropylthio, 1,1-Dimethylethylthio, Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2,2-Di-methylpropylthio, 1-Ethylpropylthio, Hexylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Trimethylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropylthio und 1-Ethyl-2-methylpropylthio; Alkenyl: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 oder 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1-propenyl, 1-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Methyl-1-butenyl, 2-Methyl-1-butenyl, 3-Methyl-1-butenyl, 1-Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl-2-propenyl, 1,2-Dimethyl-1-propenyl, 1,2-Dimethyl- 2-propenyl, 1-Ethyl-1-propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1-pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-Dimethyl-2-butenyl, 1,1-Di-methyl-3-butenyl, 1,2-Dimethyl-1-
butenyl, 1,2-Dimethyl-2-butenyl, 1,2-Dimethyl-3-butenyl, 1,3-Dimethyl-1-butenyl, 1,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Eth yl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1- Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl und 1-Ethyl-2-methyl-2-propenyl; C 1 -C 6 alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2- Dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; 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 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2- Dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4- Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-p entenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1, 2-dimethyl-1- butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2- butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl -2-methyl-2-propenyl;
Alkenyloxy: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, welche über ein Sauerstoffatom (-O-) an das Gerüst gebunden sind; Alkenyloxy: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via an oxygen atom (-O-);
Alkenylthio: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind; Alkenylthio: straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the structure via a sulfur atom (-S-);
Alkenylamino: eine Aminogruppe, welche eine geradkettige oder verzweigte Alkenylgruppe mit 2 bis 6 Kohlenstoffatomen wie vorstehend genannt trägt; Alkenylcarbonyl: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind; Alkinyl: geradkettige oder verzweigte Alkinylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C2-C6-Alkinyl wie Ethinyl, 2-Propinyl, 2-Butinyl, 3-Butinyl, 1-Methyl-2-propinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1-Methyl-2-butinyl, 1-Methyl-3-butinyl, 2-Methyl-3- butinyl, 1,1-Dimethyl-2-propinyl, 1-Ethyl-2-propinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1-Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-2-pentinyl, 1,1-Dimethyl-2-butinyl, 1,1-Dimethyl-3-butinyl, 1,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 1-Ethyl-2-butinyl, 1-Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2-propinyl; Alkenylamino: an amino group which carries a straight-chain or branched alkenyl group having 2 to 6 carbon atoms as mentioned above; Alkenylcarbonyl: straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-); Alkynyl: straight-chain or branched alkynyl groups with 2 to 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, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl 2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3- pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2- Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2- propinyl;
Alkinyloxy: geradkettige oder verzweigte Alkinylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, welche über ein Sauerstoffatom (-O-) an das Gerüst gebunden sind;
Alkinylthio: geradkettige oder verzweigte Alkinylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind; Alkynyloxy: straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via an oxygen atom (-O-); Alkynylthio: straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a sulfur atom (-S-);
Alkinylamino: eine Aminogruppe, welche eine geradkettige oder verzweigte Alkinylgruppe mit 2 bis 6 Kohlenstoffatomen wie vorstehend genannt trägt; Alkinylcarbonyl: geradkettige oder verzweigte Alkinylgruppen mit 3 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind; Cycloalkyl: monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoffringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl; Alkynylamino: an amino group which carries a straight-chain or branched alkynyl group having 2 to 6 carbon atoms as mentioned above; Alkynylcarbonyl: straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-); Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Cycloalkoxy: monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoffringgliedern wie vorstehend genannt, welche über ein Sauerstoffatom (-O-) an das Gerüst gebunden sind; Cycloalkoxy: monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-);
Cycloalkylthio: monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoffringgliedern wie vorstehend genannt, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind; Cycloalkylamino: eine Aminogruppe, welche eine monocyclische Alkylgruppe mit 3 bis 6 Kohlenstoffringgliedern wie vorstehend genannt trägt; Cycloalkylthio: monocyclic alkyl groups with 3 to 6 carbon ring members as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-); Cycloalkylamino: an amino group bearing a monocyclic alkyl group having 3 to 6 carbon ring members as mentioned above;
Cycloalkenyl: monocyclische Alkenylgruppen mit 5 bis 8 Kohlenstoffringgliedern, z.B. Cyclopentenyl, Cyclohexenyl, Cycloheptenyl und Cyclooctenyl; Cycloalkenyloxy: monocyclische Alkenylgruppen mit 5 bis 8 Cycloalkenyl: monocyclic alkenyl groups with 5 to 8 carbon ring members, e.g. Cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl; Cycloalkenyloxy: monocyclic alkenyl groups with 5 to 8
Kohlenstoffringgliedern wie vorstehend genannt, welche über ein Sauerstoffatom (-O-) an das Gerüst gebunden sind; Cycloalkenylthio: monocyclische Alkenylgruppen mit 5 bis 8 Carbon ring members as mentioned above, which are bonded to the structure via an oxygen atom (-O-); Cycloalkenylthio: monocyclic alkenyl groups with 5 to 8
Kohlenstoffringgliedern wie vorstehend genannt, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind; Cycloalkenylamino: eine Aminogruppe, welche eine monocyclische Alkenylgruppe mit 5 bis 8 Kohlenstoffringgliedern wie vorssehend genannt trägt;
Heterocyclyl, Heterocyclyloxy, Heterocyclylthio bzw. Heterocyclylamino: drei- bis sechsgliedrige, gesättigte oder partiell ungesättigte mono- oder polycyclische Heterocyclen, die ein bis drei Hereroatome ausgewählt aus einer Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel enthalten, und welche direkt bzw. (Heterocyclyloxy) über ein Sauerstoffatom, bzw. (Heterocyclylthio) über ein Schwefelatom oder (Heterocyclylamino) über ein Stickstoffatom an das Gerüst gebunden sind, wie z.B. 2-Tetrahydrofuranyl, Oxiranyl, 3-Tetrahydrofuranyl, 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-Oxazolidinyl, 2-Thiazolidinyl, 4-Thiazolidinyl, 5-Thiazolidinyl, 2-Imidazolidinyl, 4-Imidazolidinyl, 1,2,4-Oxadiazolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadiazolidin- 3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,4-Triazolidin-3-yl, 1,3,4-Oxadiazolidin-2-yl, 1,3,4-Thiadiazolidin-2-yl, 1,3,4-Triazolidin-2-yl, 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,3-Dihydrofur-4-yl, 2,3-Dihydro-fur-5-yl, 2,5-Dihydro-fur-2-yl, 2,5-Dihydrofur-3-yl, 2,3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2,3-Dihydrothien-4-yl, 2,3-Dihydrothien-5-yl, 2,5-Dihydrothien-2-yl, 2,5-Dihydrothien-3-yl, 2,3-Dihydropyrrol-2-yl, 2,3-Dihydropyrrol-3-yl, 2,3-Dihydropyrrol-4-yl, 2,3-Dihydropyrrol-5-yl, 2,5-Dihydropyrrol-2-yl, 2,5-Dihydropyrrol-3-yl, 2,3-Dihydroisoxazol-3-yl, 2,3-Dihydroisoxazol-4-yl, 2,3-Dihydroisoxazol-5-yl, 4,5-Dihydroisoxazol-3-yl, 4, 5-Dihydroisoxazol-4-yl, 4,5-Dihydroisoxazol-5-yl, 2,5-Dihydroisothiazol-3-yl, 2 , 5-Dihydroisothiazol-4-yl, 2,5-Dihydroisothiazol-5-yl, 2,3-Dihydroisopyrazol3-yl, 2,3-Dihydroisopyrazol-4-yl, 2,3-Dihydroisopyrazol-5-yl, 4,5-Dihydroisopyrazol-3-yl, 4,5-Dihydroisopyrazol-4-yl, 4,5-Dihydroisopyrazol-5-yl, 2,5-Dihydroisopyrazol-3-yl, 2,5-Dihydroisopyrazol-4-yl, 2,5-Dihydroisopyrazol-5-yl, 2,3-Dihydrooxazol-3-yl, 2,3-Dihydrooxazol-4-yl, 2,3-Dihydrooxazol-5-yl, 4,5-Dihydrooxazol-3-yl, 4,5-Dihydrooxazol-4-yl, 4,5-Dihydrooxazol-5-yl, 2,5-Dihydrooxazol-3-yl, 2,5-Dihydrooxazol-4-yl, 2 ,5-Dihydrooxazol-5-yl, 2,3-Dihydrothiazol-2-yl, 2,3-Dihydrothiazol-4-yl, 2,3-Dihydrothiazol-5-yl, 4,5-Dihydrothiazol-2-yl, 4,5-Dihydrothiazol-4-yl, 4,5-Dihydrothiazol-5-yl, 2,5-Dihydrothiazol-2-yl, 2,5-Dihydrothiazol-4-yl, 2,5-Dihydrothiazol-5-yl, 2,3-Dihydroimidazol-2-yl, 2,3-Dihydroimidazol-4-yl, 2, 3-Dihydroimidazol-5-yl, 4,5-Dihydroimidazol-2-yl, 4,5-Dihydroimidazol-4-yl, 4,5-Dihydroimidazol-5-yl, 2,5-Dihydroimidazol-2-yl, 2 ,5-Dihydroimidazol-4-yl, 2,5-Dihydroimidazol-5-yl, 2-Morpholinyl, 3-Morpholinyl, 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 3-Tetrahydropyridazinyl, 4-Tetrahydropyridazinyl, 2-Tetrahydropyrimidinyl, 4-Tetrahydropyrimidinyl, 5-Tetrahydropyrimidinyl, 2-Tetrahydro
pyrazinyl, 1,3,5-Tetrahydrotriazin-2-yl, 1,2,4-Tetrahydrotriazin-3-yl, 1,3-Dihydrooxazin-2-yl, 1,3-Dithian-2-yl, 2-Tetrahydropyranyl, 1,3-Dioxolan-2-yl, 3,4,5,6-Tetrahydropyridin-2-yl, 4H-1,3-Thiazin-2-yl, 4H-3, 1-Benzothiazin-2-yl, 1,1-Dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-Benzothiazin-3-yl, 2H-1,4-Benzoxazin-3-yl, 1,3-Dihydrooxazin-2-yl, 1,3-Dithian-2-yl, Carbon ring members as mentioned above, which are bonded to the structure via a sulfur atom (-S-); Cycloalkenylamino: an amino group which carries a monocyclic alkenyl group with 5 to 8 carbon ring members as provided for above; Heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hereroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or (heterocyclyloxy) are bound to the skeleton via an oxygen atom, or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom, such as, for example, 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidone -Pyrrolidinyl, 3-isoxazoldinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl , 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4 -Thiadiazolidin- 3-yl , 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1 , 3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydro-fur-5 -yl, 2,5-dihydro-fur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothiene -4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrole -3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazole -3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazole -5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol3-yl, 2,3-dihydroisopyrazol-4 -yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3 -yl, 2,5-dihydroisopyrazole- 4-yl, 2,5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazole 3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazole 5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol 4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazole 2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazole 5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydro pyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3, 1-benzothiazin-2-yl, 1, 1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2- yl, 1,3-dithian-2-yl,
Aryl bzw. Aryloxy, Arylthio, Arylamino, Arylcarbonyl und Arylsulfonyl: aromatische mono- oder polycyclische KohlenwasserStoffreste welche direkt bzw. (Aryloxy) über ein Sauerstoffatom (-O-) oder (Arylthio) ein Schwefelatom (-S-), (Arylamino) über ein Stickstoffatom oder (Arylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Arylsulfonyl) über eine Sulfonylgruppe (-SO2-) an das Gerüst gebunden sind, z.B. Phenyl, Naphthyl und Phenanthrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyloxy und die entsprechenden Carbonyl- und Sulfonylreste; Aryl or aryloxy, arylthio, arylamino, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon residues which directly or (aryloxy) via an oxygen atom (-O-) or (arylthio) a sulfur atom (-S-), (arylamino) via a nitrogen atom or (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-SO 2 -) are bound to the structure, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl - and sulfonyl residues;
Hetaryl bzw. Hetaryloxy, Hetarylthio, Hetarylamino, Hetarylcarbonyl und Hetarylsulfonyl: aromatische mono- oder polycyclische Reste welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom oder ein Sauerstoff- oder ein Schwefelatom enthalten können und welche direkt bzw. (Hetaryloxy) über ein Sauerstoffatom (-O-) oder (Hetarylthio) ein Schwefelatom (-S-), (Hetarylamino) über ein Stickstoffatom oder (Hetarylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Hetarylsulfonyl) über eine Sulfonylgruppe (-SO2-) an das Gerüst gebunden sind, z.B. Hetaryl or hetaryloxy, hetarylthio, hetarylamino, hetarylcarbonyl and hetarylsulfonyl: 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 or one oxygen or one sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-O-) or (hetarylthio) a sulfur atom (-S-), (hetarylamino) via a nitrogen atom or (hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a Sulfonyl group (-SO 2 -) are bound to the skeleton, for example
- 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyrrolyl, 3-Pyrrolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Imidazolyl, 4-Imidazolyl, 1,2,4-Triazol-3-yl und 1,3,4-Triazol-2-yl; 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-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff oder ein Schwefelatom: 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 Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder Schwefelatom als Ringglieder enthalten können, z.B. 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-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-Imidazolyl, 4-Imidazolyl, 1,2,4-Oxadi
azol-3-yl, 1,2,4-Oxadiazol-5-yl, 1,2,4-Thiadiazol-3-yl, 1,2,4- Thiadiazol-5-yl, 1,2,4-Triazol-3-yl, 1,3,4-Oxadiazol-2-yl, 1,3,4-Thiadiazol-2-yl und 1,3,4-Triazol-2-yl; 5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one 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-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadi azol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazole 3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
- benzokondensiertes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome oder ein Stickstoffatom und/oder ein Sauerstoff- oder Schwefelatom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder ein Schwefelatom als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein Stickstoff- und ein benachbartes Kohlenstoffringglied durch eine Buta-1, 3-dien-1,4-diylgruppe verbrückt sein können; - Benzo-condensed 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;
- über Stickstoff gebundenes 5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome. oder über Stickstoff gebundenes benzokondensiertes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein - 5-membered heteroaryl bound via nitrogen, containing one to four nitrogen atoms. or benzo-fused 5-membered heteroaryl bonded via nitrogen, containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one
Stickstoff- und ein benachbartes Kohlenstoffringglied durch eine Buta-1,3-die-n- 1,4-diylgruppe verbrückt sein können, wobei diese Ringe über eines der Stickstoffringglieder an das Gerüst gebunden sind; Nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-the-n-1,4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
- 6-gliedriges Heteroaryl, enthaltend ein bis drei bzw. ein bis vier Stickstoffatome: 6-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei bzw. ein bis vier Stickstoffatome als Ringglieder enthalten können, z.B. 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 und 1,2,4,5-Tetrazin-3-yl;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;
- benzokondensiertes 6-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome: 6 -Ring Heteroarylgruppen in welchen zwei benachbarte Kohlenstoffringglieder durch eine Buta-1,3-dien- 1,4-diylgruppe verbrückt sein können, z.B. Chinolin, Isochino- lin, Chinazolin und Chinoxalin, bzw. die entsprechenden Oxy-, Thio-, Amino, Carbonyl- oder Sulfonylgruppen. - Benzo-fused 6-membered heteroaryl containing one to four nitrogen atoms: 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, or the corresponding oxy, thio, amino, carbonyl or sulfonyl groups.
Die Angabe "partiell oder volls tändig halogeniert" soll zum Ausdruck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein können.
Die Angabe "substituiert" in Bezug auf die bei der Definition von R4 genannten Reste soll zum Ausdruck bringen, daß die betreffenden Gruppen partiell oder vollständig halogeniert sind und/oder eine bis drei der folgenden Gruppen tragen: The expression "partially or completely halogenated" is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above. The term "substituted" in relation to the radicals mentioned in the definition of R 4 is intended to express that the groups in question are partially or completely halogenated and / or carry one to three of the following groups:
- Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,
- C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkylcarbonyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-alkylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-alkylaminothiocarbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, - C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylaminocarbonyl, di -C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy,
C(=NORb) -Zn-Rc oder unsubstituiertes oder durch übliche Gruppen substituiertes Benzyl, Benzyloxy und Benzylthio; C (= NOR b ) -Z n -R c or unsubstituted or substituted by usual groups benzyl, benzyloxy and benzylthio;
- C3-C6-Cycloalkyl, C3-C6-Cycloalkoxy, Heterocyclyl, Heterocycly- loxy, Aryl, Aryloxy, Arylthio, Aryl-C1-C4-alkyl, Aryl-C1-C4- alkoxy, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclisehen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder eine bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-alkylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-alkylaminothiocarbonyl, C2-C6-Alkenyl, - C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylthio, aryl-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkoxy, hetaryl , Hetaryloxy and Hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 - Alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylaminocarbonyl, di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 - Alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl,
C2-C6-Alkenyloxy, C(=NORb) -Zn-Rc, oder unsubstituiertes oder durch übliche Gruppen substituiertes Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio. C 2 -C 6 alkenyloxy, C (= NOR b ) -Z n -R c , or unsubstituted or substituted by conventional groups, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio.
Die Angabe "durch übliche Gruppen substi tuiert" soll zum Ausdruck bringen, daß die betreffenden Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Substituenten tragen können: Cyano, Nitro, Hydroxy, Amino, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Alkylamino, Di-C1-C4-alkylamino, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, Phenyl, Phenoxy, Benzyl und Benzyloxy, und/oder ein an zwei benachbarte Atome gebundenes C3-C5-Alkylen, C2-C4-Alkylenoxy, C1-C4-Oxyalkylenoxy, und/ oder eine Gruppe C(=NORb)-Zn-Rc. The expression "substituted by conventional groups" is intended to express that the radicals in question can be partially or completely halogenated and / or can carry one to three of the following substituents: cyano, nitro, hydroxy, amino, C 1 -C 4 - Alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, di-C 1 -C 4 - alkylamino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, phenyl, phenoxy, benzyl and benzyloxy, and / or a C 3 -C 5 alkylene, C 2 -C 4 alkyleneoxy bonded to two adjacent atoms , C 1 -C 4 -Oxyalkylenoxy, and / or a group C (= NOR b ) -Z n -R c .
Unter 5- oder 6-gliedrigen heteroaromatischen Ringen in der Definition von A sind insbesondere die folgenden Gruppen A-1 bis A-88 zu verstehen. In den mit * gekennzeichneten Positionen erfolgt die Bindungen an R4 , die mit # gekennzeichneten Positionen markieren die Bindung zum Rest des Moleküls. Die Stickstoffatome
der 5-Ring-Heteoaromaten mit freien Valenzen können in dieser Position Wasserstoff oder C1-C6-Alkyl tragen.5- or 6-membered heteroaromatic rings in the definition of A are to be understood in particular as the following groups A-1 to A-88. In the positions marked with * the bonds to R 4 take place , the positions marked with # mark the bond to the rest of the molecule. The nitrogen atoms the 5-ring heteroaromatics with free valences can carry hydrogen or C 1 -C 6 alkyl in this position.
Im Hinblick auf ihre biologische Wirkung sind Verbindungen der Formel I bevorzugt, in denen Y für Sauerstoff und R1 für Methyl steht. With regard to their biological action, preference is given to compounds of the formula I in which Y is oxygen and R 1 is methyl.
Gleichermaßen bevorzugt sind Verbindungen der Formel I, in denenEqually preferred are compounds of the formula I in which
X NOCH3 und Y NRa bedeutet und Ra für Wasserstoff oder Methyl steht. X is NO 3 and Y is NR a and R a is hydrogen or methyl.
Gleichermaßen bevorzugt sind Verbindungen der Formel I, in denenEqually preferred are compounds of the formula I in which
X NOCH3 und Y NRa bedeutet und R1 für Wasserstoff oder Methyl steht. X is NO 3 and Y is NR a and R 1 is hydrogen or methyl.
Des weiteren bevorzugt sind Verbindungen der Formel I, in denen X NOCH3 und Y NRa bedeutet und Ra und R1 unabhängig voneinander Wasserstoff oder Methyl bedeuten. Also preferred are compounds of formula I in which X is NOCH 3 and Y is NR a and R a and R 1 are independently hydrogen or methyl.
Des weiteren bevorzugt sind Verbindungen der Formel I, in denenFurthermore preferred are compounds of formula I in which
X NOCH3 und Y NRa bedeutet und Ra für Waserstoff und R1 fürX is NO 3 and Y is NR a and R a is hydrogen and R 1 is
Methyl steht. Methyl stands.
Des weiteren bevorzugt sind Verbindungen der Formel I, in denen X NOCH3 und Y NRa bedeutet und Ra für Waserstoff und R1 für Wasserstoff steht. Also preferred are compounds of the formula I in which X is NOCH 3 and Y is NR a and R a is hydrogen and R 1 is hydrogen.
Daneben werden Verbindungen der Formel I bevorzugt, in denen XIn addition, compounds of the formula I are preferred in which X
CHCH3 und Y Sauerstoff bedeutet.
Daneben werden Verbindungen der Formel I bevorzugt, in denen X CHCH2CH3 und Y Sauerstoff bedeutet. CHCH 3 and Y means oxygen. In addition, compounds of the formula I are preferred in which X is CHCH 2 CH 3 and Y is oxygen.
Daneben werden Verbindungen der Formel I bevorzugt, in denen X für NOCH3 und Y für O steht. In addition, compounds of the formula I are preferred in which X is NOCH 3 and Y is O.
Daneben werden Verbindungen der Formel I bevorzugt, in denen X für CHOCH3 und Y für O steht. Insbesondere werden Verbindungen der Formel I bevorzugt, in denen R1 für Methyl steht. In addition, preference is given to compounds of the formula I in which X is CHOCH 3 and Y is O. Compounds of the formula I in which R 1 is methyl are particularly preferred.
Daneben werden Verbindungen der Formel I bevorzugt, in denen Y für O und R1 für Wasserstoff steht. In addition, compounds of the formula I are preferred in which Y is O and R 1 is hydrogen.
Außerdem werden Verbindungen der Formel I bevorzugt, in denen m für 0 oder 1, insbesondere 0, steht. Compounds of the formula I are also preferred in which m represents 0 or 1, in particular 0.
Für den Fall, daß m für 1 steht werden Verbindungen der Formel I bevorzugt, in denen R2 für Halogen, C1-C4-Alkyl und C1-C4-Alkoxy, insbesondere Fluor, Chlor, Methyl und Methoxy, steht. If m is 1, preference is given to compounds of the formula I in which R 2 is halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, in particular fluorine, chlorine, methyl and methoxy.
Daneben werden Verbindungen I bevorzugt, in denen R3 für einen der folgenden Substituenten steht: Wasserstoff, Hydroxy, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Alkylthio und C3-C6-Cycloalkyl, insbesondere Wasserstoff, Hydroxy, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Methoxy, Methylthio und Cyclopropyl. Daneben werden Verbindungen I bevorzugt, in denen R3 für einen der folgenden Substituenten steht: Wasserstoff, Halogen, In addition, compounds I are preferred in which R 3 represents one of the following substituents: hydrogen, hydroxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 - C 4 alkylthio and C 3 -C 6 cycloalkyl, in particular hydrogen, hydroxy, chlorine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy, methylthio and cyclopropyl. In addition, compounds I are preferred in which R 3 represents one of the following substituents: hydrogen, halogen,
C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Alkylthio und C3-C6-Cycloalkyl, insbesondere Wasserstoff, Chlor, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Methoxy, Methylthio und Cyclopropyl. C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio and C 3 -C 6 cycloalkyl, in particular hydrogen, chlorine, methyl, ethyl, n -Propyl, iso-propyl, trifluoromethyl, methoxy, methylthio and cyclopropyl.
Daneben werden Verbindungen I bevorzugt, in denen R3 für Wasserstoff oder C1-C4-Alkyl, insbesondere Methyl, steht. Außerdem werden Verbindungen I bevorzugt, in denen R4 für substituiertes Phenyl steht. In addition, compounds I are preferred in which R 3 represents hydrogen or C 1 -C 4 alkyl, in particular methyl. In addition, compounds I are preferred in which R 4 represents substituted phenyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für durch übliche Gruppen substituiertes Phenyl steht.
Gleichermaßen werden Verbindungen I bevorzugt, in denen R4 für Phenyl steht, welches mindestens einen der folgenden Substituenten trägt: Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und C1-C4-Alkoxy, insbesondere Fluor, Chlor, Brom, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Methoxy und Ethoxy. Furthermore, compounds I are preferred in which R 4 represents phenyl substituted by customary groups. Likewise preferred are compounds I in which R 4 is phenyl which carries at least one of the following substituents: cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 - Alkoxy, especially fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, methoxy and ethoxy.
Gleichermaßen werden Verbindungen I bevorzugt, in denen R4 für Phenyl steht, welches mindestens eine Trifluormethylgruppe trägt. Likewise preferred are compounds I in which R 4 is phenyl which carries at least one trifluoromethyl group.
Gleichermaßen werden Verbindungen I bevorzugt, in denen R4 für Phenyl steht, welches eine Gruppe C(=NORb)-Zn-Rc trägt und zusätzlich einen bis drei der folgenden Substituenten tragen kann: Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und Likewise, preference is given to compounds I in which R 4 is phenyl which carries a group C (= NOR b ) -Z n -R c and can additionally carry one to three of the following substituents: cyano, nitro, halogen, C 1 - C 4 alkyl, C 1 -C 4 haloalkyl and
C1-C4-Alkoxy. C 1 -C 4 alkoxy.
Außerdem werden Verbindungen I bevorzugt, in denen A für einen der folgenden Reste steht: A-2, A-6, A-10, A-11, A-12, A-17, A-18, A-20, A-21, A-27, A-29, A-33, A-35, A-39, A-43, A-44, A-45, A-46, A-49, A-50, A-51, A-52, A-55, A-59, A-60, A-61, A-62, A-63, A-65, A-67, A-68, A-69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 und A-83. In addition, compounds I are preferred in which A represents one of the following radicals: A-2, A-6, A-10, A-11, A-12, A-17, A-18, A-20, A- 21, A-27, A-29, A-33, A-35, A-39, A-43, A-44, A-45, A-46, A-49, A-50, A-51, A-52, A-55, A-59, A-60, A-61, A-62, A-63, A-65, A-67, A-68, A-69, A-71, A- 72, A-76, A-78, A-79, A-80, A-81 and A-83.
Außerdem werden Verbindungen I bevorzugt, in denen A für einen der folgenden Reste steht: A-2, A-20, A-21, A-39, A-55, A-59, A-67, A-68, A-69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 und A-83, insbesondere bevorzugt A-20. In addition, compounds I are preferred in which A represents one of the following radicals: A-2, A-20, A-21, A-39, A-55, A-59, A-67, A-68, A- 69, A-71, A-72, A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-20.
Außerdem werden Verbindungen I bevorzugt, in denen A für einen der folgenden Reste steht: A-10, A-ll, A-12, A-27, A-29, A-43, A-44, A-45, A-46, A-63 und A-65, insbesondere bevorzugt A-44. In addition, compounds I are preferred in which A represents one of the following radicals: A-10, A-II, A-12, A-27, A-29, A-43, A-44, A-45, A- 46, A-63 and A-65, particularly preferably A-44.
Außerdem werden Verbindungen I bevorzugt, in denen A für einen der folgenden Reste steht: A-17, A-18, A-33, A-35, A-49, A-50, A-51, A-52, A-60, A-61 und A-62, insbesondere bevorzugt A-50. In addition, compounds I are preferred in which A represents one of the following radicals: A-17, A-18, A-33, A-35, A-49, A-50, A-51, A-52, A- 60, A-61 and A-62, particularly preferably A-50.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-2, A-20, A-21 und A-39, besonders bevorzugt A-20, steht. Außerdem werden Verbindungen I bevorzugt, in denen A für A-10, A-ll und A-12, besonders bevorzugt A-10, steht. In addition, compounds I are preferred in which A is A-2, A-20, A-21 and A-39, particularly preferably A-20. In addition, compounds I are preferred in which A is A-10, A-II and A-12, particularly preferably A-10.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-17 und A-18, besonders bevorzugt A-18, steht.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-27, A-29, A-33 und A-35, besonders bevorzugt A-33 und A-35, steht. In addition, compounds I are preferred in which A is A-17 and A-18, particularly preferably A-18. In addition, compounds I are preferred in which A is A-27, A-29, A-33 and A-35, particularly preferably A-33 and A-35.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-43, A-44, A-45 und A-46, besonders bevorzugt A-44 und A-46, steht. In addition, compounds I are preferred in which A is A-43, A-44, A-45 and A-46, particularly preferably A-44 and A-46.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-49, A-50, A-51 und A-52, besonders bevorzugt A-50 und A-52, steht. Außerdem werden Verbindungen I bevorzugt, in denen A für A-55, A-59, A-60, A-61, A-62, A-63 und A-65, besonders bevorzugt A-60, A-62 und A-65, steht. In addition, compounds I are preferred in which A is A-49, A-50, A-51 and A-52, particularly preferably A-50 and A-52. In addition, compounds I are preferred in which A is A-55, A-59, A-60, A-61, A-62, A-63 and A-65, particularly preferably A-60, A-62 and A- 65, stands.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-67, A-68, A-69, A-71 und A-72, besonders bevorzugt A-67 und A-68, steht. In addition, compounds I are preferred in which A is A-67, A-68, A-69, A-71 and A-72, particularly preferably A-67 and A-68.
Außerdem werden Verbindungen I bevorzugt, in denen A für A-76, A-78, A-79, A-80, A-81 und A-83, besonders bevorzugt A-79, steht. In addition, compounds I are preferred in which A is A-76, A-78, A-79, A-80, A-81 and A-83, particularly preferably A-79.
Daneben werden Verbindungen der Formel I bevorzugt, in denen R5 Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C4-Alkoxy-C1-C4-alkyl, C1-C4 -Halogenalkoxy-C1-C4-alkyl, Cyano-C1-C4-alkyl, Amino-C1-C4-alkyl, C1-C4-Alkylamino-C1-C4-alkyl, Di-C1-C4-alkylamino-C1-C4-alkyl, C3-C6-Cycloalkyl-C1-C4-alkyl und C3-C6-Cycloalkyl bedeutet. In addition, compounds of the formula I are preferred in which R 5 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, di- C 1 -C 4 alkylamino-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl.
Daneben werden Verbindungen I bevorzugt, in denen R5 für einen der folgenden Substituenten steht: Wasserstoff, C1-C4-Alkyl und C1-C4-Alkoxy-C1-C4-alkyl, insbesondere Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl und Methoxyethyl. In addition, preference is given to compounds I in which R 5 represents one of the following substituents: hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, in particular hydrogen, methyl, ethyl, n-propyl, iso-propyl and methoxyethyl.
Daneben werden Verbindungen I bevorzugt, in denen R5 für einen der folgenden Substituenten steht: Wasserstoff und C1-C4-Alkyl, insbesondere Methyl, Ethyl, n-Propyl und iso-Propyl, besonders bevorzugt Methyl. In addition, compounds I are preferred in which R 5 represents one of the following substituents: hydrogen and C 1 -C 4 -alkyl, in particular methyl, ethyl, n-propyl and isopropyl, particularly preferably methyl.
Daneben werden Verbindungen I bevorzugt, in denen R5 C3-C6-Alkenyl und C3-C6-Halogenalkenyl bedeutet. In addition, compounds I are preferred in which R 5 is C 3 -C 6 alkenyl and C 3 -C 6 haloalkenyl.
Daneben werden Verbindungen I bevorzugt, in denen R5 für Allyl steht. Daneben werden Verbindungen I bevorzugt, in denen R5 für In addition, compounds I are preferred in which R 5 is allyl. In addition, compounds I are preferred in which R 5 is
trans-3-Chlor-prop-2-enyl steht.
Gleichermaßen werden Verbindungen I bevorzugt, in denen R5 C3-C6-Alkinyl und C3-C6-Halogenalkinyl bedeutet. trans-3-chloro-prop-2-enyl. Likewise, compounds I are preferred in which R 5 is C 3 -C 6 alkynyl and C 3 -C 6 haloalkynyl.
Daneben werden Verbindungen I bevorzugt, in denen R5 für Propargyl steht. In addition, compounds I are preferred in which R 5 is propargyl.
Insbesondere sind im Hinblick auf ihre Verwendung die in den folgenden Tabellen zusammengestellten Verbindungen I bevorzugt. In particular, in view of their use, the compounds I compiled in the tables below are preferred.
Die Verbindungen I eignen sich als Fungizide. The compounds I are suitable as fungicides.
Die Verbindungen I zeichnen sich durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Phycomyceten und Basidiomyceten, aus. Sie sind zum Teil systemisch wirksam und können im Pflanzenschutz als Blatt- und Bodenfungizide eingesetzt werden. Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Weizen, Roggen, Gerste, Hafer, Reis, Mais, Gras, Baumwolle, Soja, Kaffee, Zukkerrohr, Wein, Obst- und Zierpflanzen und Gemüsepflanzen wie Gurken, Bohnen und Kürbisgewächsen, sowie an den Samen dieser Pflanzen. The compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides. They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans and Pumpkin family, as well as on the seeds of these plants.
Speziell eignen sie sich zur Bekämpfung folgender Pflanzenkrankheiten: Erysiphe graminis (echter Mehltau) in Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuckerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthosporium-Arten an Getreide, Septoria nodorum an Weizen, Botrytis cinerea (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cereospora arachidicola an Erdnüssen, Pseudocercosporella herpotrichoides an Weizen, Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Fusarium- und Verticillium-Arten an verschiedenen Pflanzen, Plasmopara viticola an Reben, Alternaria-Arten an Gemüse und Obst. They are particularly suitable for combating the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia types on cereals, Rhizoctonia and rice species Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Cereospora arachidicola on peanuts, Pseudocrichosidesella on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.
Die Verbindungen I eignen sich außerdem zur Bekämpfung von The compounds I are also suitable for combating
Schadpilzen im Materialschutz (z.B. Holz, Papier, Fasern bzw. Gewebe) und im Vorratsschutz. Harmful fungi in material protection (e.g. wood, paper, fibers or fabric) and in storage protection.
Die Verbindungen I werden angewendet, indem man die Pilze oder die vor Pilzbefall zu schützenden Pflanzen, Saatgüter, Materialien oder den Erdboden mit einer fungizid wirksamen Menge der Wirkstoffe behandelt. Die Anwendung erfolgt vor oder nach der Infektion der Materialien, Pflanzen oder Samen durch die Pilze. The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
Sie können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine feine und gleichmäßige Verteilung der erfindungsgemäßen Verbindungen gewährleisten. Die Formulierungen werden in bekannter Weise hergestellt,
z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/ oder Trägerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungsmittel auch andere organische Lösungsmittel als Hilfslösungsmittel verwendet werden können. Als Hilfsstoffe kommen dafür im wesentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol), chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol), Ketone (z.B. Cyclohexanon), Amine (z .B.Ethanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtionogene und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose. They can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compounds according to the invention. The formulations are prepared in a known manner for example, by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. Ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
Die fungiziden Mittel enthalten im allgemeinen zwischen 0,1 und 95, vorzugsweise zwischen 0,5 und 90 Gew.-% Wirkstoff. The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
Die Aufwandmengen liegen bei der Anwendung im Pflanzenschutz je nach Art des gewünschten Effektes zwischen 0,01 und 2,0 kg Wirkstoff pro ha. Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 0,1 g, vorzugsweise 0,01 bis 0,05 g je Kilogramm Saatgut benötigt. The application rates in crop protection, depending on the type of effect desired, are between 0.01 and 2.0 kg of active ingredient per ha. In the case of seed treatment, amounts of active ingredient generally range from 0.001 to 0.1 g, preferably 0.01 to 0.05 g required per kilogram of seed.
Bei der Anwendung im Material- bzw. Vorratsschutz richtet sich die Aufwandmenge an Wirkstoff nach der Art des Einsatzgebietes und des gewünschten Effekts. Übliche Aufwandmengen sind im When used in material or storage protection, the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates are in
Materialschutz beispielsweise 0,001 g bis 2 kg, vorzugsweise 0,005 g bis 1 kg Wirkstoff pro Qubikmeter behandelten Materials. Die erfindungsgemäßen Mittel können in der Anwendungsform als Fungizide auch zusammen mit anderen Wirkstoffen vorliegen, der z.B. mit Herbiziden, Insektiziden, Wachstumsregulatoren, Fungiziden oder auch mit Düngemitteln. Beim Vermischen mit Fungiziden erhält man dabei in vielen Fällen eine Vergrößerung des fungiziden Wirkungsspektrums. Material protection, for example 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material. The agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
Die folgende Liste von Fungiziden, mit denen die erfindungsgemäßen Verbindungen gemeinsam angewendet werden können, soll die Kombinationsmöglichkeiten erläutern, nicht aber einschränken:
Schwefel, Dithiocarbamate und deren Derivate, wie Ferridimethyldithiocarbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisdithiocarbamat, Manganethylenbisdithiocarbamat, Mangan-Zink-ethylendiamin-bis-dithiocarbamat, Tetramethylthiuramdisulfide, Ammoniak-Komplex von Zink-(N,N-ethylen-bis-dithiocarbamat), Ammoniak-Komplex von Zink-(N,N'-propylen-bis-dithiocarbamat), Zink(N,N'-propylenbis-dithiocarbamat), N,N'-Polypropylen-bis-(thiocarbamoyl) disulfid; Nitroderivate, wie Dinitro- (1-methylheptyl) -phenylcrotonat, 2-sec-Butyl-4,6-dinitrophenyl-3,3-dimethylacrylat, 2-sec-Butyl4,6-dinitrophenyl-isopropylcarbonat, 5-Nitro-isophthalsäure-diisopropylester; heterocyclische Substanzen, wie 2-Heptadecyl-2-imidazolin-acetat, 2,4-Dichlor-6-(o-chloranilino)-s-triazin, O,O-Diethylphthalimidophosphonothioat, 5-Amino-1-[bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4- triazol, 2,3-Dicyano-1,4-dithioanthrachinon, 2-Thio-1,3-dithiolo[4,5-b]chinoxalin, 1-(Butylcarbamoyl)-2-benzimidazol-carbaminsäuremethylester, 2-Methoxycarbonylamino-benzimidazol, 2-(Furyl-(2))-benzimidazol, 2-(Thiazolyl(4))-benzimidazol, N-(1,1,2,2-Tetrachlorethylthio)-tetrahydrophthalimid, N-Trichlormethylthio-tetrahydrophthalimid, N-Trichlormethylthio-phthalimid, The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations: Sulfur, dithiocarbamates and their derivatives, such as iron, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, Tetramethylthiuramdisulfide, ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), ammonia complex of Zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl4,6-dinitrophenyl-isopropyl carbonate, 5-nitro-isophthalic acid diisopropyl ester ; heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethylphthalimidophosphonothioate, 5-amino-1- [bis- (dimethylamino) -phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoyl ) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl (4)) -benzimidazole, N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide,
N-Dichlorfluormethylthio-N',N'-dimethyl-N-phenyl-schwefelsäurediamid, 5-Ethoxy-3-trichlormethyl-1, 2,3-thiadiazol, 2-Rhodanmethylthiobenzthiazol, 1,4-Dichlor-2,5-dimethoxybenzol, 4-(2-Chlorphenylhydrazono)-3-methyl-5-isoxazolon, Pyridin-2-thio-1-oxid, 8-Hydroxychinolin bzw. dessen Kupfersalz, 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4, 4-dioxid, 2-Methyl-5,6-dihydro-4H-pyran-3-carbonsäure-anilid, 2-Methyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-furan-3-carbonsäureanilid, 2,4,5-Trimethyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-furan-3-carbonsäurecyclohexylamid, N-Cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carbonsäureamid, 2-Methyl-benzoesäure-anilid, 2-Iod-benzoesäure-anilid, N¬Formyl-N-morpholin-2,2,2-trichlorethylacetal, Piperazin-1,4-diylbis-(1-(2,2,2-trichlor-ethyl)-formamid, 1-(3,4-Dichloranilino)-1-formylamino-2, 2,2-trichlorethan, 2,6-Dimethyl-N-tridecylmorpholin bzw. dessen Salze, 2,6-Dimethyl-N-cyclododecyl-morpholin bzw. dessen Salze, N-[3-(p-tert.-Butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morpholin, N-[3-(p-tert.-Butylphenyl)-2-methylpropyl]-piperidin, 1-[2-(2,4-Dichlorphenyl)-4-ethyl-1,3¬dioxolan-2-yl-ethyl]-1H-1,2,4-triazol, 1-[2-(2,4-Dichlorphenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazol, N-(n-Propyl)-N-(2,4,6-trichlorphenoxyethyl)-N'-imidazol-yl-harnstoff,
1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanon, 1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, α-(2-Chlorphenyl)-α-(4-chlorphenyl)-5-pyrimidinmethanol, 5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin, Bis-(p-chlorphenyl)-3-pyridinmethanol, 1,2-Bis-(3-ethoxycarbonyl-2-thioureido)-benzol, 1,2-Bis-(3-methoxycarbonyl-2-thioureido)-benzol, sowie verschiedene Fungizide, wie Dodecylguanidinacetat, 3-[3- (3,5-Dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimid, Hexachlorbenzol, DL-Methyl-N-(2,6-dimethyl-phenyl)-N-furoyl(2)-alaninat, DL-N-(2,6-Dimethyl-phenyl)-N-(2'-methoxyacetyl)-alaninmethyl- ester, N-(2,6-Dimethylphenyl)-N-chloracetyl-D, L-2-aminobutyrolacton, DL-N-(2,6-Dimethylphenyl)-N-(phenylacetyl)-alaninmethylester, 5-Methyl-5-vinyl-3-(3,5-dichlorphenyl)-2,4-dioxo- 1,3-oxazolidin, 3-[3,5-Dichlorphenyl(-5-methyl-5-methoxymethyl]- 1,3-oxazolidin- 2,4-dion, 3-(3,5-Dichlorphenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-Dichlorphenyl)-1,2-dimethylcyclopropan-1,2-dicarbonsäureimid, 2-Cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamid, 1-[2-(2,4-Dichlorphenyl)-pentyl]-1H-1,2,4-triazol, 2,4-Difluor-α-(1H-1,2,4-triazolyl-1-methyl)-benzhydrylalkohol, N-(3-Chlor-2,6-dinitro-4-trifluormethyl-phenyl)-5-trifluormethyl-3-chlor-2-aminopyridin, 1-((bis-(4-Fluorphenyl)-methylsilyl)-methyl)-1H-1,2,4-triazol. N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenyl-sulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1, 2,3-thiadiazole, 2-rhodanmethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1, 4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, 2-methyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide, N- Cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide, 2-methyl-benzoic acid anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino-2, 2,2-trichloroethane, 2,6 -Dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecyl-mo rpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethyl-morpholine, N- [3- (p-tert-butylphenyl) -2 -methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, 1- [2nd - (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2nd , 4,6-trichlorophenoxyethyl) -N'-imidazol-yl urea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3-dimethyl- 1- (1H-1,2,4-triazol-1-yl) -2-butanol, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidinemethanol, 5-butyl-2-dimethylamino- 4-hydroxy-6-methyl-pyrimidine, bis (p-chlorophenyl) -3-pyridine methanol, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl -2-thioureido) -benzene, as well as various fungicides, such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2, 6-dimethyl-phenyl) -N-furoyl (2) -alaninate, DL-N- (2,6-dimethyl-phenyl) -N- (2'-methoxyacetyl) -alanine methyl ester, N- (2,6- Dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5- dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl] -1,3-oxazolidine-2,4-dione, 3- (3rd , 5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dime thylcyclopropane-1,2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4- triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl) -5- trifluoromethyl-3-chloro-2-aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.
Strobilurine wie Methyl-E-methoxyimino-[α-(o-tolyloxy)-o-tolyl]-acetat, Methyl-E-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylat, Methyl-E-methoxyimino-[α-(2-phenoxyphenyl)]-acetamid, Methyl-E-methoxyimino-[α-(2,5-dimethylphenoxy)-o-tolyl]-acetamid. Strobilurins such as methyl-E-methoxyimino- [α- (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl } -3-methoxyacrylate, methyl-E-methoxyimino- [α- (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [α- (2,5-dimethylphenoxy) -o-tolyl] acetamide.
Anilinopyrimidine wie N-(4,6-Dimethylpyrimidin-2-yl)-anilin, N-[4-Methyl-6-(1-propinyl)-pyrimidin-2-yl]-anilin, N-(4-Methyl-6-cyclopropyl-pyrimidin-2-yl)-anilin. Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 -cyclopropyl-pyrimidin-2-yl) aniline.
Phenylpyrrole wie 4-(2,2-Difluor-1,3-benzodioxol-4-yl)-pyrrol-3-carbonitril. Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile.
Zimtsäureamide wie 3-(4-Chlorphenyl)-3-(3,4-dimethoxyphenyl)-acrylsäuremorpholid. Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide.
Die Verbindungen der Formel I sind außerdem geeignet, Schädlinge aus der Klasse der Insekten, Spinnentiere und Nematoden wirksam zu bekämpfen. Sie können im Pflanzenschutz sowie auf dem Hygiene- , Vorratsschutz- und Veterinärsektor als Schädlingsbekämpfungsmittel eingesetzt werden.
Zu den schädlichen Insekten gehören aus der Ordnung der Schmetterlinge (Lepidoptera) beispielsweise Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis eitrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis. The compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, storage protection and veterinary sectors. The harmful insects from the order of the butterflies (Lepidoptera) include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobisturaumumone, Cheimatobisturaumumone Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Helium, Heliothiothiothi, Heliothiothiothiothiothiis, Heliothiothiothiisi, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais, Grapholitha funebranais , Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege stymicaliaiaia, monella lymphoma malachia lympia, monachroma, lympia triaxia triaxia, lympia ustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis eitrella, Pieris brassicae, Plathypena xabylaciaellaellaiaellaellaellaiaellaellaellaiaella pella Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.
Aus der Ordnung der Käfer (Coleoptera) beispielsweise Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.
Aus der Ordnung der Zweiflügler (Diptera) beispielsweise Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis,From the order of the beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Byus Bruchus pisorusum , Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornisis, Diabrotica, diabrotica, Epibrotusisinotilisisinodisinotis, Epabritus histopathy , Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema orynhiachono , Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria. From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropucitae, Cordylobia anthropucaga, brassylaciaacropucita, brassylaciaacropucita, brassylaciaacropacea, brassylaciaacropaceacita, brassylaciaacropia , Fannia canicularis, Gasterophilus intestinalis,
Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae,Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae,
Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria peetoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysoeyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus,Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria peetoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysoeyami, Phorbia antiqua, Phorbia brassicae, Phorbiaagomoletis, Phorbiaagolellais, Phorbiaagolellais ,
Tipula oleracea, Tipula paludosa. Tipula oleracea, Tipula paludosa.
Aus der Ordnung der Thripse (Thysanoptera) beispielsweise Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci. From the order of the thrips (Thysanoptera), for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
Aus der Ordnung der Hautflügler (Hymenoptera) beispielsweise Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invieta. From the order of the hymenoptera, for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invieta.
Aus der Ordnung der Wanzen (Heteroptera) beispielsweise Acrosternum hilare, Blissus leueopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor. From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leueopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensidata, Nezara pratensidata, Sol .
Aus der Ordnung der Pflanzensauger (Homoptera) beispielsweise Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui,From the order of the plant suckers (Homoptera), for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui,
Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharieida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.
Aus der Ordnung der Termiten (Isoptera) beispielsweise Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus,Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megourophusumisodishod , Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii. From the order of the termites (Isoptera), for example Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus,
Termes natalensis. Aus der Ordnung der Geradflügler (Orthoptera) beispielsweise Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus. Termes natalensis. From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinataus, Melanopladusana, Melanopladipana Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
Aus der Klasse der Arachnoidea beispielsweise Spinnentiere (Acarina) wie Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranyehus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus paeificus, Tetranychus telarius, Tetranychus urticae. From the class of the arachnoid, for example arachnids (Acarina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata Otobius megnini, Paratetranyehus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus paeificus, Tetranychus telarius, Tetranychus urticae.
Aus der Klasse der Nematoden beispielsweise Wurzelgallennematoden, z.B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Zysten bildende Nematoden, z.B. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, Stock- und Blattälchen, z.B. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinetus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus elaytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi. From the class of nematodes, for example, root gall nematodes, e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf wholes, e.g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinetus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus elaytoni, Tylenchorhynchusus Prubus negate, Prelateus, chelate
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln, Granulaten durch versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie soll
ten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten. The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied. The application forms depend entirely on the purposes; she should ensure the finest possible distribution of the active compounds according to the invention in any case.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. The active substance concentrations in the ready-to-use preparations can be varied over a wide range.
Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%. Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen. Die Aufwandmenge an Wirkstoff zur Bekämpfung von Schädlingen beträgt unter Freilandbedingungen 0,1 bis 2,0, vorzugsweise 0,2 bis 1,0 kg/ha. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. The active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives. The application rate of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron, stark polare Lösungsmittel, z.B. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser, in Betracht. To produce directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions from medium to high boiling points, such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, by means of wetting agents,
Haft-, Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind. Adhesives, dispersants or emulsifiers are homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Dibutylnaphthalinsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Fettalkoholsulfate und Fettsäuren sowie deren Alkali- und Erdalkalisalze, Salze von sulfatiertem Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem
Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, Alkylphenolpolyglykolether, Tributylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpolyglykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Betracht. Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids as well as their alkali and alkaline earth metal salts, salts of sulfonated fatty alcohol alcohols, condensation products of sulfonated fatty alcohol alcohols and condensation products Naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, Laurylalkoholpolyglykoletheracetal, sorbitol esters , Lignin sulfite liquor and methyl cellulose.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden. Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 95Gew.-%, vorzugsweise zwischen 0,1 und 90 Gew.-% des Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt. The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Beispiele für Formulierungen sind: Examples of formulations are:
I. 5 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 5 Gew.-% des Wirkstoffs enthält. I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 5% by weight of the active ingredient.
II. 30 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit (Wirkstoffgehalt 23 Gew.-%). II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A preparation of the active ingredient with good adhesiveness (active ingredient content 23% by weight) is obtained in this way.
III. 10 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 90 Gew.-Teilen Xylol, 6 Gew.-Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1Mol Ölsäure-N-monoethanolamid, 2 Gew.-Teilen Calciumsalz der Dodecylbenzolsulfonsäure und 2 Gew.-III. 10 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2% by weight
Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 9 Gew.-%). Parts of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil are present (active ingredient content 9% by weight).
IV. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 60 Gew.-Teilen Cyclohexanon,IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone,
30 Gew.-Teilen Isobutanol, 5 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol
und 5 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 16 Gew.-%). V. 80 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalinalpha-sulfonsäure, 10 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 7 Gew.-Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen (Wirkstoffgehalt 80 Gew.-%). 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 16% by weight). V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenalphasulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and in grind in a hammer mill (active ingredient content 80% by weight).
VI. Man vermischt 90 Gew.-Teile einer erfindungsgemäßen Verbindung mit 10 Gew.-Teilen N-Methyl-α-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropfen geeignet ist (Wirkstoffgehalt 90 Gew.-%). VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for use in the form of very small drops (active substance content 90% by weight).
VII. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 40 Gew.-Teilen Cyclohexanon, 30Gew.-Teilen Isobutanol, 20 Gew.-Teilen des AnlagerungsProduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gew.-Teilen Wasser erhält maneine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält. VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight. -Share the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
VIII. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-α-sulfonsäure, 17 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gew.-Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gew.-Teilen Wasser erhält man eine VIII. 20 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives one
Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält. Spray liquor containing 0.1% by weight of the active ingredient.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden, wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.
Zu den Wirkstoffen können Öle verschiedenen Typs, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1:10 bis 10:1 zugemischt werden. Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers. Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
Synthesebeispiele Synthesis examples
Die in den nachstehenden Synthesebeispielen wiedergegebenen VorSchriften wurden unter entsprechender Abwandlung der AusgangsVerbindungen zur Gewinnung weiterer Verbindungen I benutzt. Die so erhaltenen Verbindungen sind in den anschließenden Tabellen mit physikalischen Angaben aufgeführt. Beispiel 1: Synthese von (E,E,E)-2-[[[[2-(1-(4-Chlorphenyl)-pyrazol-4-yl)-2-(methoxyimino)-1-(methyl)ethyliden]amino]oxy]methyl]-α-(methoxyimino)-phenylessigsäure-methylester The instructions given in the synthesis examples below were used with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are listed in the tables below with physical details. Example 1: Synthesis of (E, E, E) -2 - [[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] -α- (methoxyimino) phenylacetic acid methyl ester
Eine Lösung aus 2,7 g (9,23 mmol) E,E-1-(1-(4-Chlorphenyl)pyra¬zol-4-yl)-1-methoxyimino)-propan-2-on-2-oxim in 20 ml N,N-Dimethylformamid wurde mit 1,7 g 30%-iger Natriummethylat Lösung (in Methanol) versetzt und 15 min bei Raumtemperatur (ca. 25°C) gerührt. A solution of 2.7 g (9.23 mmol) of E, E-1- (1- (4-chlorophenyl) pyra¬zol-4-yl) -1-methoxyimino) propan-2-one-2-oxime 1.7 g of 30% sodium methylate solution (in methanol) were added to 20 ml of N, N-dimethylformamide and the mixture was stirred at room temperature (approx. 25 ° C.) for 15 min.
Nach Zugabe von 2,7 g (1 eq.) 2-Brommethyl-α-methoxyimino-phenylessigsäure-methylester in 20 ml N,N-Dimethylformamid wurde eine weitere Stunde bei Raumtemperatur gerührt. Die Mischung wurde anschließend auf Eiswasser gegeben und mit Pentan versetzt, wobei das Produkt als Feststoff ausfiel. Der Feststoff wurde isoliert und durch Verrühren mit Methanol gereinigt. Man erhielt 4,2 g (91%) der Titelverbindung (Fp.: 146-149°C). After addition of 2.7 g (1 eq.) Of 2-bromomethyl-α-methoxyimino-phenylacetic acid methyl ester in 20 ml of N, N-dimethylformamide, the mixture was stirred for a further hour at room temperature. The mixture was then poured onto ice water and pentane was added, the product precipitating as a solid. The solid was isolated and purified by stirring with methanol. 4.2 g (91%) of the title compound were obtained (mp: 146-149 ° C.).
1H-NMR (d6-DMSO; δ in ppm): 2,07 (s,3H); 3,71 (s,3H); 3,87 1 H NMR (d 6 -DMSO; δ in ppm): 2.07 (s, 3H); 3.71 (s, 3H); 3.87
(s,3H); 4,02 (s,3H); 5,06 (s,2H); 7,27 (m, 1H); 7,43 (s, 3H); 4.02 (s, 3H); 5.06 (s. 2H); 7.27 (m. 1H); 7.43
(m,3H); 7,57 (d,2H); 7,68 (d,2H); 8,01 (s,1H); 8,56 (s, 1H)
Beispiel 2 Synthese von (E,E,E)-2-[[[[2-(1-(4-Chlorphenyl)-pyrazol-4-yl)-2-(methoxyimino)-1-(methyl)ethyliden]amino]oxy]methyl]-α-(methoxyimino)-phenylessigsäure-monomethylamid (m, 3H); 7.57 (d. 2H); 7.68 (d. 2H); 8.01 (s, 1H); 8.56 (s, 1H) Example 2 Synthesis of (E, E, E) -2 - [[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino ] oxy] methyl] -α- (methoxyimino) phenylacetic acid monomethylamide
Eine Lösung aus 1,6 g (3,2 mmol) der Verbindung aus Beispiel 1 in 50 ml Tetrahydrofuran wurde mit 2,5 g 40%-iger Monomethylamin Lösung (in Wasser) versetzt und für 24 Stunden bei Raumtemperatur (ca. 25°C) gerührt. Das so erhaltene Reaktionsgemisch wurde mit Wasser versetzt und mit tert.-Buthylmethylether extrahiert. Die organische Phase wurde isoliert, gewaschen, getrocknet und bei vermindertem Druck eingeengt. Der erhaltene Rückstand wurde mit Methanol verrührt, wobei das Produkt kristallisierte. Man erhielt 1,3 g (82%) der Titelverbindung (Fp.: 100-103°C). A solution of 1.6 g (3.2 mmol) of the compound from Example 1 in 50 ml of tetrahydrofuran was mixed with 2.5 g of 40% monomethylamine solution (in water) and for 24 hours at room temperature (approx. 25 ° C) stirred. The reaction mixture thus obtained was mixed with water and extracted with tert-butyl methyl ether. The organic phase was isolated, washed, dried and concentrated under reduced pressure. The residue obtained was stirred with methanol, the product crystallizing. 1.3 g (82%) of the title compound (mp: 100-103 ° C.) were obtained.
1H-NMR (d6-DMSO; δ in ppm): 2,09 (s,3H); 2,66 (d,3H); 3,81 1 H NMR (d 6 -DMSO; δ in ppm): 2.09 (s, 3H); 2.66 (d. 3H); 3.81
(s,3H); 4,01 (s,3H); 5,05 (s,2H); 7,17 (m, 1H); 7,36 (s, 3H); 4.01 (s, 3H); 5.05 (s. 2H); 7.17 (m. 1H); 7.36
(m,3H); 7,54 (d,2H); 7,65 (d,2H); 8,03 (s,1H); 8,21 (m, 3H); 7.54 (d. 2H); 7.65 (d. 2H); 8.03 (s, 1H); 8.21
(m,1H); 8,52 (s,1H) (m, 1H); 8.52 (s, 1H)
Beispiel 3: Synthese von (E,E,E)-2-[[[[2-(1-(4-Chlorphenyl)-pyrazol-4-yl)-2-(methoxyimino)-1-(methyl)ethyliden]amino]oxy]methyl]-α-(methoxyimino)-phenylessigsäure-amid Example 3: Synthesis of (E, E, E) -2 - [[[[[2- (1- (4-chlorophenyl) pyrazol-4-yl) -2- (methoxyimino) -1- (methyl) ethylidene] amino] oxy] methyl] -α- (methoxyimino) phenylacetic acid amide
Eine Mischung aus 1,6 g (3,2 mmol) der Verbindung aus Beispiel 1, 20 ml Methanol, 30 ml Tetrahydrofuran und 20 ml 25%-iger Ammoniak Lösung (in Wasser) wurde für 3 Tage bei Raumtemperatur (ca. 25°C) gerührt. Das so erhaltene Reaktionsgemisch wurde in Eiswasser gegeben und mit Dichlormethan extrahiert. Die organische Phase wurde isoliert, gewaschen, getrocknet und bei vermin
dertem Druck eingeengt. Der erhaltene Rückstand wurde säulenchromatographisch (Kieselgel; n-Hexan/tert.-Butylmethylether 1:1) gereinigt. Man erhielt 1,0 g (82%) der Titelverbindung (Fp.: 164-167°C). A mixture of 1.6 g (3.2 mmol) of the compound from Example 1, 20 ml of methanol, 30 ml of tetrahydrofuran and 20 ml of 25% ammonia solution (in water) was for 3 days at room temperature (approx. 25 ° C) stirred. The reaction mixture thus obtained was poured into ice water and extracted with dichloromethane. The organic phase was isolated, washed, dried and at min reduced pressure. The residue obtained was purified by column chromatography (silica gel; n-hexane / tert-butyl methyl ether 1: 1). 1.0 g (82%) of the title compound (mp: 164-167 ° C.) were obtained.
1H-NMR (d6-DMSO; δ in ppm): 2,12 (s,3H); 3,82 (s,3H); 4,02 1 H NMR (d 6 -DMSO; δ in ppm): 2.12 (s, 3H); 3.82 (s, 3H); 4.02
(s,3H); 5,06 (s,2H); 7,20 (m, 1H); 7,36-7,68 (m,9H); 8,06 (s, 3H); 5.06 (s. 2H); 7.20 (m. 1H); 7.36-7.68 (m, 9H); 8.06
(s,1H); 8,54 (s,1H) (s, 1H); 8.54 (s, 1H)
Beispiele für die Wirkung gegen Schadpilze Die fungizide Wirkung der Verbindungen der allgemeinen Formel I ließ sich durch die folgenden Versuche zeigen: Examples of the action against harmful fungi The fungicidal action of the compounds of the general formula I could be shown by the following experiments:
Die Wirkstoffe wurden als 20%-ige Emulsion in einem Gemisch aus 70 Gew.-% Cyclohexanon, 20 Gew.-% Nekanil® LN (Lutensol® AP6, Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) und 10 Gew.-% Emulphor® EL (Emulan® EL, Emulgator auf der Basis ethoxylierter Fettalkohole) aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.
A) Wirksamkeit gegen Weizenmehltau The active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight. % Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration. A) Efficacy against powdery mildew
Blätter von in Töpfen gewachsenen Weizenkeimlingen der Sorte "Frühgold" wurden mit wäßriger Spritzbrühe, die mit einer Stammlösung aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 %Leaves of potted wheat seedlings of the "Frühgold" variety were washed with an aqueous spray mixture containing a stock solution of 10% active ingredient, 63% cyclohexanone and 27%
Emulgiermittel angesetzt wurde, besprüht und 24 Stunden nach dem Antrocknen des Spritzbelages mit Sporen des Weizenmehltaus (Erysiphe graminis var. tritici) bestäubt. Die Versuchspflanzen wurden anschließend im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 80 % relativer Luftfeuchtigkeit aufgestellt. Nach 7 Tagen wurde das Ausmaß der Mehltauentwicklung visuell in % Befall der gesamten Blattfläche ermittelt. In diesem Test zeigten die mit 250 ppm der Verbindungen Nr. 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.22 und 1.32 behandelten Plfanzen 0 bis 15 % Befall, während die unbehandelten Pflanzen zu 75 % befallen waren. Emulsifier was prepared, sprayed and dusted with spores of powdery mildew (Erysiphe graminis var. Tritici) 24 hours after the spray coating had dried on. The test plants were then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area. In this test, those with 250 ppm of compounds no. 1.2, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.22 and 1.32 treated plants were 0 to 15% infected, while the untreated plants were 75% infected.
B) Wirksamkeit gegen Plasmopara viticola B) Efficacy against Plasmopara viticola
Blätter von Topfreben der Sorte "Müller -Thurgau" wurden mit wäßriger Spritzbrühe, die mit einer Stammlösung aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, besprüht. Um die Dauerwirkung der Substanzen beurteilen zu können, wurden die Pflanzen nach dem Antrocknen des Spritzbelages für 7 Tage im Gewächshaus aufgeteilt. Erst dann wurden die Blätter mit einer wäßrigen Zoosporenaufschwemmung von Plasmopara viticola inokuliert. Danach wurden die Reben zunächst für 48 Stunden in einer wasserdampfgesättigten Kammer bei 24°C und anschließend für 5 Tage im Gewächshaus bei Temperaturen zwischen 20 und 30°C aufgestellt. Nach dieser Zeit wurden die Pflanzen zur Beschleunigung des Sporangienträgerausbruchs abermals für 16 Stunden in eine feuchte Kammer gestellt. Dann wurde das Ausmaß der Befallsentwicklung auf den Blattunterseiten visuell ermittelt. In diesem Test zeigten die mit 63 ppm der Verbindungen Nr.Leaves of potted vines of the "Müller-Thurgau" variety were sprayed with an aqueous spray mixture which had been prepared with a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier. In order to be able to assess the long-term effect of the substances, the plants were divided in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola. The vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually. In this test, those with 63 ppm of compound no.
1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.23, 1.24 und 1.32 behandelten Pflanzen 0 bis 15 % Befall, während die unbehandelten Pflanzen zu 70 % befallen waren.
Beispiele für die Wirkung gegen tierische Schädlinge 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.22, 1.23, 1.24 and 1.32 treated plants 0 to 15% infestation, while the untreated plants too 70% were infected. Examples of the action against animal pests
Die Wirkung der Verbindungen der allgemeinen Formel I gegen tierische Schädlinge ließ sich durch folgende Versuche zeigen: The activity of the compounds of the general formula I against animal pests was demonstrated by the following tests:
Die Wirkstoffe wurden The active ingredients were
a. als 0,1%-ige Lösung in Aceton oder a. as a 0.1% solution in acetone or
b. als 10%-ige Emulsion in einem Gemisch aus 70 Gew.-% Cyclohexanon, 20 Gew.-% Nekanil® LN (Lutensol® AP6, Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) und 10 Gew.-% Emulphor® EL (Emulan® EL, Emulgator auf der Basis ethoxylierter Fettalkohole) aufbereitet und entsprechend der gewünschten Konzentration mit Aceton im Fall von a. bzw. mit Wasser im Fall von b. verdünnt. b. as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) processed and with the desired concentration with acetone in the case of a. or with water in the case of b. diluted.
Nach Abschluß der Versuche wurde die jeweils niedrigste Konzentration ermittelt, bei der die Verbindungen im Vergleich zu unbehandelten Kontrollversuchen noch eine 80 bis 100%-ige Hemmung bzw. Mortalität hervorriefen (Wirkschwelle bzw. Minimalkonzentration). After the end of the tests, the lowest concentration was determined at which the compounds still caused 80 to 100% inhibition or mortality compared to untreated control tests (threshold of action or minimum concentration).
Wirkung gegen Tetranychus urticae (Bohnenspinnmilbe), Kontaktwirkung, Spritzversuch Effect against Tetranychus urticae (bean spider mite), contact effect, spray test
Getopfte Buschbohnen mit einem voll ausgebildeten Blattpaar, wurden in der Spritzkabine mit der wäßrigen Wirkstofflösung tropfnaß gespritzt. Die Pflanzen wurden dazu über eine Laufschiene auf den Drehteller der Spritzkabine geführt und mit 3 unterschiedlich ausgerichteten Düsen bei Ausbringung von 30 cm3 Wirkstofflösung allseitig besprüht. Der Spritzvorgang dauerte ca. 20 Sekunden. Die Pflanzen wiesen einen starken Milbenbefall und reichlich Eiablage auf. Die Wirkung wurde nach 5 Tagen mittels Binokular bonitiert. Dabei wurde festgestellt, ob alle Stadien gleichmäßig erfaßt sind. Die Pflanzen standen während dieser Zeit unter normalen Gewächshausbedingungen. In diesem Versuch zeigte die Substanz 1.17 aus der Tabelle eine Wirkschwelle von 200 ppm.
Potted bush beans with a fully developed pair of leaves were sprayed to runoff point in the spray booth with the aqueous active ingredient solution. The plants were guided over a running rail to the turntable of the spray booth and sprayed on all sides with 3 differently oriented nozzles when 30 cm 3 of active ingredient solution was applied. The spraying process took about 20 seconds. The plants were heavily infested with mites and abundant oviposition. The effect was assessed after 5 days using a binocular. It was determined whether all stages were recorded evenly. The plants were under normal greenhouse conditions during this time. In this experiment, substance 1.17 from the table showed an activity threshold of 200 ppm.
Claims
1. Phenylessigsäurederivate der Formel I 1. Phenylacetic acid derivatives of the formula I.
in der die Substituenten und der Index die folgende Bedeutung haben: in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3, CHCH3 und CHCH2CH3; X NOCH 3 , CHOCH 3 , CHCH 3 and CHCH 2 CH 3 ;
Y NRa und O; Ra, R1 Wasserstoff und Alkyl; Y NR a and O; R a , R 1 are hydrogen and alkyl;
R2 Cyano, Nitro, Halogen, Alkyl, Halogenalkyl und Alkoxy; m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht; R 2 cyano, nitro, halogen, alkyl, haloalkyl and alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Hydroxy, Amino, Cyano, Halogen, Alkyl, Halogenalkyl, Cycloalkyl, Alkoxy, Alkylthio, Alkyla- mino und Dialkylamino; R 3 is hydrogen, hydroxy, amino, cyano, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, alkylamino and dialkylamino;
A ein 5- oder 6-gliedriger heteroaromatischer Ring; A is a 5- or 6-membered heteroaromatic ring;
R4 substituiertes Aryl; R 4 substituted aryl;
R5 Wasserstoff, ggf. subst. Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Heterocyclyl, Aryl und Hetaryl, sowie deren Salze. R 5 hydrogen, optionally subst. Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and hetaryl, and their salts.
2. Phenylessigsäurederivate der Formel I gemäß Anspruch 1, in der die Substituenten und der Index die folgende Bedeutung haben: X NOCH3, CHOCH3, CHCH3 und CHCH2CH3; 2. phenylacetic acid derivatives of the formula I according to claim 1, in which the substituents and the index have the following meaning: X NOCH 3 , CHOCH 3 , CHCH 3 and CHCH 2 CH 3 ;
Y NRa und O; Ra, R1 Wasserstoff und C1-C4-Alkyl; Y NR a and O; R a , R 1 are hydrogen and C 1 -C 4 alkyl;
R2 Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und C1-C4-Alkoxy; m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht; R 2 cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy; m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Hydroxy, Amino, Cyano, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Alkylamino und Di-C1-C4-alkylamino; R 3 is hydrogen, hydroxy, amino, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 - Alkylthio, C 1 -C 4 alkylamino and di-C 1 -C 4 alkylamino;
A ein 5- oder 6-gliedriger heteroaromatischer Ring; R4 substituiertes Aryl; A is a 5- or 6-membered heteroaromatic ring; R 4 substituted aryl;
R5 Wasserstoff, C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl, wobei diese Gruppen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: R 5 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, where these groups can be partially or completely halogenated and / or can carry one to three of the following radicals:
- Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, - cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,
- C1-C6-Alkylcarbonyl, C1-C6-Alkylaminocarbonyl, Di- C1-C6-alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-alkylaminothiocarbonyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C1-C6-Alkoxy, C1-C6- Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-alkylamino, C2-C6- Alkenyloxy, - C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 - haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 alkylamino , Di-C 1 -C 6 alkylamino, C 2 -C 6 alkenyloxy,
- C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-C1-C4-alkoxy, Arylthio, Aryl-C1-C4-alkylthio, Hetaryl, Hetaryloxy, Hetaryl-C1-C4-alkoxy, Hetarylthio und Hetaryl-C1- C4-alkylthio, wobei die cyclischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, C1-C6- Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6- Alkylthio, C1-C6-Alkylamino, Di-C1-C6-alkylamino, C1-C6-Alkylaminocarbonyl, Di-C1-C6-alkylaminocarbonyl, C1-C6-Alkylaminothiocarbonyl, Di-C1-C6-alkylaminothiocarbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NORb) -Zn-Rc; - C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C 1 -C 4 -alkoxy, arylthio, aryl-C 1 -C 4 -alkylthio, hetaryl, hetaryloxy , Hetaryl-C 1 -C 4 -alkoxy, hetarylthio and hetaryl-C 1 - C 4 -alkylthio, where the cyclic radicals in turn can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, Hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 3 -C 6 - Cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 1 -C 6 alkylaminocarbonyl, Di-C 1 -C 6 alkylaminocarbonyl, C 1 -C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, Aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR b ) -Z n -R c ;
C3-C6-Cycloalkyl, C5-C8-Cycloalkenyl, Heterocyclyl, Aryl und Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: - Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, C 3 -C 6 cycloalkyl, C5 -C 8 cycloalkenyl, heterocyclyl, aryl and hetaryl, where the cyclic radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,
- C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkylcarbonyl,C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl,
C1-C6-Alkylsulfonyl, C1-C6-Alkylsulfoxyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkylcarbonyl, C1-C6-Alkoxy, C1- C6-Halogenalkoxy, C1-C6-Alkoxycarbonyl, C1-C6-Alkylthio, C1-C6-Alkylamino, Di-C1-C6-alkylamino, C1-C6- Alkylaminocarbonyl, Di-C1-C6-alkylaminocarbonyl, C1- C6-Alkylaminothiocarbonyl, Di-C1-C6-alkylaminothiocarbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylcarbonyl, Hetaryl, Hetaryloxy, Hetarylcarbonyl, C(=NORb) -Zn-Rc oder NRf-CO-D-Rg; C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylsulfoxyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 6 alkoxy, C 1 - C 6 haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 - C 6 alkylaminothiocarbonyl, di-C 1 -C 6 alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylcarbonyl, hetaryl, hetaryloxy, hetarylcarbonyl, C (= NOR b ) -Z n -R c or NR f -CO-DR g ;
Z Sauerstoff, Schwefel, oder Stickstoff, wobei der Z oxygen, sulfur, or nitrogen, the
Stickstoff Wasserstoff oder C1-C6-Alkyl trägt; D eine direkte Bindung, Sauerstoff oder NRh; n 0 oder 1; Nitrogen carries hydrogen or C 1 -C 6 alkyl; D is a direct bond, oxygen or NR h ; n 0 or 1;
Rb, Rc unabhängig voneinander Wasserstoff oder C1-C6-Alkyl; R b , R c independently of one another are hydrogen or C 1 -C 6 -alkyl;
Rf Wasserstoff, C1-C6-Alkyl, C2-C6-Alkenyl und C2-C6-Alkinyl; R f is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl;
Rg, Rh unabhängig voneinander Wasserstoff und C1-C6-Alkyl. R g , R h independently of one another hydrogen and C 1 -C 6 alkyl.
3. Verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 nicht Halogen bedeutet, dadurch gekennzeichnet, daß man ein Benzylderivat der Formel II in der L1 für eine nucleophil austauschbare Abgangsgruppe steht, in an sich bekannter Weise mit einem Hydroxyimin der Formel III 3. A process for the preparation of the compounds of formula I according to claim 1, in which R 3 is not halogen, characterized in that a benzyl derivative of formula II in which L 1 represents a nucleophilically exchangeable leaving group, in a manner known per se, with a hydroxyimine of the formula III
umsetzt. implements.
4. Verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 nicht Halogen bedeutet, dadurch gekennzeichnet, daß man ein Benzylderivat der Formel II gemäß Anspruch 3 in an sich bekannter Weise mit einem Dihydroxyimin der Formel IV 4. A process for the preparation of the compounds of formula I according to claim 1, in which R 3 is not halogen, characterized in that a benzyl derivative of formula II according to claim 3 in a manner known per se with a dihydroxyimine of formula IV
zu einer Verbindung der Formel V to a compound of formula V
umsetzt und V anschließend mit einer Verbindung der Formel VI reacted and V then with a compound of formula VI
in der L2 für eine nucleophil austauschbare Abgangsgruppe steht, zu I umsetzt. in which L 2 represents a nucleophilically exchangeable leaving group, converts to I.
5. verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 nicht Halogen bedeutet, dadurch gekennzeichnet, daß man ein Benzylderivat der Formel II gemäß Anspruch 3 in an sich bekannter Weise mit einem Carbonylhydroxyimin der Formel VII 5. Process for the preparation of the compounds of the formula I according to claim 1, in which R 3 is not halogen, characterized in that a benzyl derivative of the formula II according to claim 3 in a manner known per se with a carbonylhydroxyimine of the formula VII
zu einer Verbindung der Formel VIII to a compound of formula VIII
umsetzt, VIII anschließend entweder a) zunächst mit Hydroxylamin oder dessen Salz und danach mit einer Verbindung der Formel VI (R5-L2) gemäß Anspruch 4 oder VIII, then either a) first with hydroxylamine or its salt and then with a compound of formula VI (R 5 -L 2 ) according to claim 4 or
b) mit einem Hydroxylamin oder einem Hydroxylammoniumsalz der Formel IXa bzw. IXb b) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb
in der Qθ für das Anion einer Säure steht, zu I umsetzt. in which Q θ stands for the anion of an acid, converts to I.
6. Mittel gegen tierische Schädlinge oder Schadpilze, enthaltend übliche Zusatzstoffe und eine wirksame Menge einer Verbindung der Formel I gemäß Anspruch 1. 6. Agents against animal pests or harmful fungi, containing conventional additives and an effective amount of a compound of formula I according to claim 1.
7. Mittel nach Anspruch 6 zur Bekämpfung tierischer Schädlinge aus der Klasse der Insekten, Spinntiere oder Nematoden. 7. Composition according to claim 6 for combating animal pests from the class of insects, arachnids or nematodes.
8. Verfahren zur Bekämpfung von tierischen Schädlingen oder Schadpilzen, dadurch gekennzeichnet, daß man die Schädlinge oder Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Flächen, Materialien oder Räume mit einer wirksamen Menge einer Verbindung der Formel I gemäß Anspruch 1 behandelt. 8. A method for controlling animal pests or harmful fungi, characterized in that the pests or harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them are treated with an effective amount of a compound of the formula I according to claim 1.
9. Verwendung der Verbindungen I gemäß Anspruch 1 zur Herstellung von Mitteln gegen tierische Schädlinge oder Schadpilze. 9. Use of the compounds I according to claim 1 for the preparation of agents against animal pests or harmful fungi.
10. Verwendung der Verbindungen I gemäß Anspruch 1 zur Bekämpfung von tierischen Schädlingen oder Schadpilzen. 10. Use of the compounds I according to claim 1 for controlling animal pests or harmful fungi.
11. Verbindungen der Formel III' 11. Compounds of the formula III '
in denen die Substituenten die folgende Bedeutung haben: U1 Sauerstoff oder NOH, in which the substituents have the following meaning: U 1 is oxygen or NOH,
U2 Sauerstoff, NOH oder NOR5, wobei die Reste A, R3, R4 und R5 die in Anspruch 1 gegebene Bedeutung haben. U 2 is oxygen, NOH or NOR 5 , where the radicals A, R 3 , R 4 and R 5 have the meaning given in claim 1.
12. Verwendung der Verbindungen III' gemäß Anspruch 11 als Zwischenprodukte. 12. Use of the compounds III 'according to claim 11 as intermediates.
13. Verbindungen der Formel V 13. Compounds of formula V
in denen U für Sauerstoff oder NOH steht und die Reste A, X, Y, R1, R2, R3 und R4 sowie der Index die in Anspruch 1 gegebene Bedeutung haben. in which U represents oxygen or NOH and the radicals A, X, Y, R 1 , R 2 , R 3 and R 4 and the index have the meaning given in claim 1.
14. Verwendung der Verbindungen V gemäß Anspruch 13 als Zwischenprodukte. 14. Use of the compounds V according to claim 13 as intermediates.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19545094 | 1995-12-04 | ||
DE1995145094 DE19545094A1 (en) | 1995-12-04 | 1995-12-04 | Phenylacetic acid derivatives, processes and intermediates for their preparation and compositions containing them |
PCT/EP1996/005247 WO1997020816A1 (en) | 1995-12-04 | 1996-11-28 | Phenylacetic acid derivatives, process and intermediates for their preparation and their use as pesticides and/or fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0865432A1 true EP0865432A1 (en) | 1998-09-23 |
Family
ID=7779086
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP96941603A Withdrawn EP0865432A1 (en) | 1995-12-04 | 1996-11-28 | Phenylacetic acid derivatives, process and intermediates for their preparation and their use as pesticides and/or fungicides |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0865432A1 (en) |
JP (1) | JP2000505058A (en) |
AU (1) | AU1094097A (en) |
DE (1) | DE19545094A1 (en) |
WO (1) | WO1997020816A1 (en) |
ZA (1) | ZA9610127B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011161945A1 (en) * | 2010-06-24 | 2011-12-29 | クミアイ化学工業株式会社 | Alkoxyimino derivative and pest control agent |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE139993T1 (en) * | 1991-01-30 | 1996-07-15 | Zeneca Ltd | FUNGICIDES |
CA2179418C (en) * | 1994-01-05 | 2004-06-22 | Hugo Ziegler | Pesticides |
NZ278072A (en) * | 1994-02-04 | 1998-02-26 | Basf Ag | Phenylacetic acid oxime derivatives; biocides |
-
1995
- 1995-12-04 DE DE1995145094 patent/DE19545094A1/en not_active Withdrawn
-
1996
- 1996-11-28 WO PCT/EP1996/005247 patent/WO1997020816A1/en not_active Application Discontinuation
- 1996-11-28 JP JP9520946A patent/JP2000505058A/en not_active Withdrawn
- 1996-11-28 AU AU10940/97A patent/AU1094097A/en not_active Abandoned
- 1996-11-28 EP EP96941603A patent/EP0865432A1/en not_active Withdrawn
- 1996-12-03 ZA ZA9610127A patent/ZA9610127B/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9720816A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE19545094A1 (en) | 1997-06-05 |
JP2000505058A (en) | 2000-04-25 |
AU1094097A (en) | 1997-06-27 |
ZA9610127B (en) | 1998-06-03 |
WO1997020816A1 (en) | 1997-06-12 |
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