DE4104377A1 - New fluoro:cyclopropane derivs. - useful as insecticides and acaricides - Google Patents
New fluoro:cyclopropane derivs. - useful as insecticides and acaricidesInfo
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- DE4104377A1 DE4104377A1 DE4104377A DE4104377A DE4104377A1 DE 4104377 A1 DE4104377 A1 DE 4104377A1 DE 4104377 A DE4104377 A DE 4104377A DE 4104377 A DE4104377 A DE 4104377A DE 4104377 A1 DE4104377 A1 DE 4104377A1
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- alkyl
- formula
- alkenyl
- compounds
- alkoxy
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- Chemical & Material Sciences (AREA)
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Abstract
Description
Die Erfindung betrifft neue Halogencyclopropylalkylderivate, ihre Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel, insbesondere gegen Insekten und Milben.The invention relates to new halogenocyclopropylalkyl derivatives, their preparation and their use as pesticides, especially against insects and mites.
Es ist bereits bekannt, daß Cyclopropanverbindungen akarizide und insektizide Eigenschaften besitzen (EP 1 16 889).It is already known that cyclopropane compounds are acaricidal and insecticidal Have properties (EP 1 16 889).
Der Nachteil der bekannten Verbindungen ist jedoch die nicht ausreichende in sektizide und akarizide Wirksamkeit.However, the disadvantage of the known compounds is that they are not sufficient in secticidal and acaricidal effectiveness.
Die Aufgabe der vorliegenden Erfindung ist es, Verbindungen zur Verfügung zu stellen, welche Insekten und Milben besser als die für diesen Zweck bekannten Verbindungen bekämpfen.The object of the present invention is to provide connections put which insects and mites better than those known for this purpose Fight connections.
Es wurde nun gefunden, daß Halogencyclopropylalkylderivate der allgemeinen Formel IIt has now been found that halocyclopropylalkyl derivatives of the general Formula I.
worin
R¹ Fluor, Chlor oder Wasserstoff bedeutet,
A die Gruppe -COOR², -CONR²R³, -CH₂OR⁴ oder -COOCH₂CONR²R³, wobei
R² und R³ unabhängig voneinander für
Wasserstoff,
C1-20-Alkyl,
C2-20-Alkenyl,
C2-20-Alkinyl,
C1-10-Alkoxy-C1-10-alkyl,
C1-10-Halogenalkyl,
Halogencyclopropyl-C1-9-alkylcarboxy-C2-10-alkyl,
Halogencyclopropyl-C1-9-alkylcarboxy-C2-6-alkoxy-C2-6-alkyl,
Aryl-C1-3-alkyl,
Aryl-C2-4-alkenyl,
Aryl-C2-4-alkinyl,
Halogenaryl-C1-3-alkyl,
Halogenaryl-C2-4-alkenyl,
Aryloxyaryl-C1-3-alkyl,
Aryloxyaryl-C2-4-alkenyl,
C1-10-Alkylaryl-C1-3-alkyl,
C1-10-Alkylaryl-C2-4-alkenyl,
C1-10-Alkoxyaryl-C1-3-alkyl,
C1-10-Alkoxyaryl-C2-4-alkenyl,
C2-6-Alkenoxyaryl-C2-4-alkenyl,
C2-6-Alkinoxyaryl-C2-4-alkenyl,
Halogencyclopropyl-C1-4-alkylcarboxyaryl,
Halogencyclopropyl-C1-4-alkylcarboxyaryl-C2-4-alkenyl,
unsubstituiertes Aryl oder durch C1-20-Alkyl, Halogen-C1-6-alkyl, C1-16-
Alkoxy, Halogen-C1-6-alkoxy, Phenyl-C1-6-alkyl, Phenyl-C1-6-alkoxy, C3-10-
Cycloalkoxy, Halogen-C3-10-cycloalkenyloxy, Halogen-C2-6-alkenyloxy, C2-6-
Alkinyloxy, Halogen-C2-6-alkinyloxy, Aryl-C1-6-alkoxy, Halogen, Amino,
Cyano, Hydroxy, Nitro, Aryloxy, Heteroaryloxy, Halogenaryloxy, Arylamino,
Halogenarylamino, C1-6-Alkoxycarbonyl, C1-6-Alkoxycarbonylmethyl, Halogen-
C1-6-alkoxycarbonyl, C1-2-Alkyldioxy, C1-6-Alkylthio, C1-6-Alkylamino,
Di-C1-6-alkylamino, ein- oder mehrfach substituiertes Aryl, freies Heteroaryl,
durch Halogen, C1-3-Alkyl oder Halogen-C1-3-alkyl substituiertes
Heteroaryl, wobei
R² und R³ gemeinsam mit dem Stickstoffatom einen gesättigten, teilgesättigten
oder ungesättigten verzweigten oder unverzweigten heterocyclischen
Ring bilden können, und
falls A für die Gruppe -COOR² steht, bedeutet R² auch ein Alkalimetallatom
oder ein Äquivalent eines zweiwertigen Metalls oder unsubstituiertes
oder durch C1-10-Alkyl ein- oder mehrfach substituiertes Ammonium, und
R⁴ Wasserstoff oder den Restwherein
R¹ is fluorine, chlorine or hydrogen,
A the group -COOR², -CONR²R³, -CH₂OR⁴ or -COOCH₂CONR²R³, where
R² and R³ independently of one another are hydrogen, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 1-10 -alkoxy-C 1-10 -alkyl, C 1-10 -haloalkyl, Halocyclopropyl-C 1-9 -alkylcarboxy-C 2-10 -alkyl, halocyclopropyl-C 1-9 -alkylcarboxy-C 2-6 -alkoxy-C 2-6 -alkyl, aryl-C 1-3 -alkyl, aryl- C 2-4 alkenyl, aryl-C 2-4 -alkynyl, haloaryl-C 1-3 alkyl, haloaryl-C 2-4 alkenyl, aryloxyaryl-C 1-3 alkyl, aryloxyaryl-C 2-4 - alkenyl, C 1-10 alkylaryl-C 1-3 alkyl, C 1-10 alkylaryl-C 2-4 alkenyl, C 1-10 alkoxyaryl-C 1-3 alkyl, C 1-10 alkoxyaryl -C 2-4 -alkenyl, C 2-6 -alkenoxyaryl-C 2-4 -alkenyl, C 2-6 -alkynoxyaryl-C 2-4 -alkenyl, halocyclopropyl-C 1-4 -alkylcarboxyaryl, halocyclopropyl-C 1- 4- alkylcarboxyaryl-C 2-4 -alkenyl, unsubstituted aryl or by C 1-20 -alkyl, halogen-C 1-6 -alkyl, C 1-16 -alkoxy, halogen-C 1-6 -alkoxy, phenyl-C 1-6 -alkyl, phenyl-C 1-6 -alkoxy, C 3-10 - cycloalkoxy, halogen-C 3-10 -cycloalkenyloxy, halogen-C 2-6 -alkenyloxy, C 2-6 - alk inyloxy, halo-C 2-6 alkynyloxy, aryl-C 1-6 -alkoxy, halogen, amino, cyano, hydroxy, nitro, aryloxy, heteroaryloxy, haloaryloxy, arylamino, haloarylamino, C 1-6 alkoxycarbonyl, C 1- 6 -alkoxycarbonylmethyl, halogen- C 1-6 -alkoxycarbonyl, C 1-2 -alkyldioxy, C 1-6 -alkylthio, C 1-6 -alkylamino, di-C 1-6 -alkylamino, mono- or polysubstituted aryl, free heteroaryl, heteroaryl substituted by halogen, C 1-3 alkyl or halogen C 1-3 alkyl, where
R² and R³ together with the nitrogen atom can form a saturated, partially saturated or unsaturated branched or unbranched heterocyclic ring, and
if A stands for the group -COOR², R² also denotes an alkali metal atom or an equivalent of a divalent metal or unsubstituted or monosubstituted or polysubstituted by C 1-10 -alkyl, and
R⁴ hydrogen or the rest
bedeuten und
n für eine gerade Zahl zwischen 2 und 20 steht,
eine im Vergleich zu den bekannten Verbindungen verbesserte insektizide und
akarizide Wirksamkeit zeigen.mean and
n stands for an even number between 2 and 20,
show an improved insecticidal and acaricidal activity compared to the known compounds.
Die Bezeichnung "Alkyl" steht für eine geradlinige oder verzweigte Kette von Kohlenstoffatomen.The term "alkyl" stands for a straight or branched chain of Carbon atoms.
Die Bezeichnung "Alkenyl" steht für eine geradlinige oder verzweigte Kette von Kohlenstoffatomen, die durch Doppelbindungen ein- oder mehrfach unterbrochen ist.The term "alkenyl" stands for a straight or branched chain of Carbon atoms that are interrupted by double bonds one or more times is.
Die Bezeichnung "Alkinyl" steht für eine geradlinige oder verzweigte Kette von Kohlenstoffatomen, die durch Dreifachbindungen ein- oder mehrfach unterbrochen ist.The term "alkynyl" stands for a straight or branched chain of Carbon atoms interrupted by triple bonds one or more times is.
Die Bezeichnung "Aryl" steht für einen ein- bis dreikernigen aromatischen Rest, wie z. B. Phenyl, Naphthyl oder Phenanthryl.The term "aryl" stands for a mono- to trinuclear aromatic residue, such as B. phenyl, naphthyl or phenanthryl.
Die Bezeichnung "Heteroaryl" steht für einen 5- oder 6gliedrigen Ring, der ein oder mehrere Stickstoff-, Sauerstoff- und/oder Schwefelatome enthält, gesättigt, teilgesättigt oder ungesättigt sein kann und gegebenenfalls benzoanelliert ist, wie z. B. Pyridin, Thiazol oder Chromen.The term "heteroaryl" stands for a 5- or 6-membered ring, the one or contains several nitrogen, oxygen and / or sulfur atoms, saturated, can be partially saturated or unsaturated and optionally benzo-fused is how As pyridine, thiazole or chromene.
Die Bezeichnung "Halogen" steht für eine ein- oder mehrfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Jod substituierte Verbindung.The term "halogen" stands for one or more, the same or differently substituted by fluorine, chlorine, bromine or iodine.
Die Bezeichnung "heterocyclischer Ring" steht z. B. für Morpholino, Piperidino, Pyrrolo, Imidazolo oder Triazolo.The term "heterocyclic ring" is e.g. B. for morpholino, piperidino, Pyrrolo, Imidazolo or Triazolo.
Die Erfindung betrifft ferner Verbindungen der allgemeinen Formel IIThe invention further relates to compounds of general formula II
worin
R¹ und n die in Formel I angegebene Bedeutung haben und
X für Hydroxy, Chlor oder Brom steht, als Zwischenprodukte zur Herstellung
von Verbindungen der Formel I.wherein
R¹ and n have the meaning given in formula I and
X represents hydroxy, chlorine or bromine, as intermediates for the preparation of compounds of the formula I.
Des weiteren betrifft die Erfindung Verbindungen der allgemeinen Formel IIIThe invention further relates to compounds of the general formula III
in der
R¹ und n die in Formel I angegebene Bedeutung haben und
Y für Hydroxy oder Brom steht, als Zwischenprodukte zur Herstellung von Verbindungen
der Formel I.in the
R¹ and n have the meaning given in formula I and
Y represents hydroxy or bromine, as intermediates for the preparation of compounds of the formula I.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel I lassen sich herstellen, indem manThe compounds of the general formula I according to the invention can be prepared by one
- a) Verbindungen der allgemeinen Formel IV CH₂=CH-CH₂-(CH₂)n-A (IV)in der A und n die in Formel I angegebenen Bedeutungen haben, in Gegenwart eines inerten Lösungsmittels mit einem Halogencarben Formel:CFR¹,in der R¹ die in Formel I angegebene Bedeutung hat, reagieren läßt, oder a) Compounds of the general formula IV CH₂ = CH-CH₂- (CH₂) n -A (IV) in which A and n have the meanings given in formula I, in the presence of an inert solvent with a halocarbene Formula: CFR¹, in which R¹ has the meaning given in formula I, can react, or
-
b) falls A in Formel I die Gruppe
-COOR²darstellt, Verbindungen der allgemeinen Formel II
in der
R¹ und n die in Formel I angegebene Bedeutung haben und
X für Hydroxy, Chlor oder Brom steht, mit einer Hydroxyverbindung der Formel R²OH, worin R² die in Formel I angegebene Bedeutung hat, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oderb) if A in formula I represents the group -COOR², compounds of general formula II in the
R¹ and n have the meaning given in formula I and
X represents hydroxy, chlorine or bromine, with a hydroxy compound of the formula R²OH, in which R² has the meaning given in formula I, optionally using a solvent and an acid acceptor, or - c) falls A in Formel I die Gruppe -CONR²R³bedeutet, Verbindungen der allgemeinen Formel II, worin R¹ und n die in Formel I angegebene Bedeutung haben und X Chlor oder Brom bedeutet, mit einem Amin der FormelHNR²R³,in der R² und R³ die in Formel I angegebene Bedeutung haben, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oder c) if A in formula I the group -CONR²R³ means compounds of general formula II, wherein R¹ and n are those in Formula I have the meaning given and X is chlorine or bromine an amine of the formula HNR²R³, in which R² and R³ have the meaning given in formula I, if appropriate using a solvent and an acid acceptor, or
-
d) falls A in Formel I die Gruppe
-COOCH₂CONR²R³bedeutet, Verbindungen der allgemeinen Formel II, worin R¹ und n die in
Formel I angegebene Bedeutung haben und X für Hydroxy steht, mit einer
Verbindung der allgemeinen Formel VIIIR²R³NCOCH₂Z (VIII)in der
R² und R³ die in Formel I angegebene Bedeutung haben und
Z für Chlor oder Brom steht, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oderd) if A in formula I means the group -COOCH₂CONR²R³, compounds of the general formula II, in which R¹ and n have the meaning given in formula I and X is hydroxy, with a compound of the general formula VIIIR²R³NCOCH₂Z (VIII) in the
R² and R³ have the meaning given in formula I and
Z represents chlorine or bromine, if appropriate using a solvent and an acid acceptor, or - e) falls A in Formel I die Gruppe -CH₂OR⁴bedeutet, Verbindungen der allgemeinen Formel III, in der Y für Hydroxy steht, mit einer Verbindung der allgemeinen FormelR² COX,in der R² die in Formel I und X die in Formel II angegebene Bedeutung haben, gegebenenfalls unter Verwendung eines Lösungsmittels, eines Säureacceptors oder eines wasserentziehenden Mittels umsetzt.e) if A in formula I the group -CH₂OR⁴ means compounds of the general formula III, in which Y is hydroxy is, with a compound of the general formula R² COX, in which R² has the meaning given in formula I and X the formula II have, optionally using a solvent, an acid acceptor or a dehydrating agent.
Die zur Herstellung der Ausgangsverbindungen der Formel II benötigten Verbindungen sind an sich bekannt oder lassen sich nach bekannten Verfahren herstellen. The compounds required for the preparation of the starting compounds of the formula II are known per se or can be produced by known processes.
Als Säureacceptor für die Durchführung der Reaktionsvarianten b) bis e) eignen sich die üblichen basischen Mittel, insbesondere aliphatische, aromatische und heterocyclische Amine, wie z. B. Triethylamin, Dimethylanilin, Dimethylbenzylamin, Pyridin und Dimethylaminopyridin oder anorganische Basen wie Oxide, Carbonate, Hydrogencarbonate und Alkoholate von Alkali- und Erdalkalimetallen wie Kaliumhydroxid, Natriumhydroxid, Natrium- und Kaliumcarbonat.Suitable as acid acceptors for carrying out reaction variants b) to e) the usual basic agents, especially aliphatic, aromatic and heterocyclic amines, such as. B. triethylamine, dimethylaniline, dimethylbenzylamine, Pyridine and dimethylaminopyridine or inorganic bases such as oxides, Carbonates, bicarbonates and alcoholates of alkali and alkaline earth metals such as potassium hydroxide, sodium hydroxide, sodium and potassium carbonate.
Als Lösungsmittel eignen sich die vorgenannten Säureacceptoren selbst oder inerte Lösungsmittel oder Gemsiche derselben untereinander.The aforementioned acid acceptors themselves or are suitable as solvents inert solvents or mixtures thereof with one another.
Genannt seien beispielsweise aliphatische, alicyclische und aromatische Kohlenwasserstoffe, die gegebenenfalls chloriert sein können wie Hexan, Cyclohexan, Petrolether, Benzol, Toluol, Xylol, Methylenchlorid, Chloroform, Kohlenstoff tetrachlorid, Ethylenchlorid, Trichlorethylen und Chlorbenzol; Ether wie Diethylether, Methylethylether, Diisopropylether, Dibutylether, Propylenoxid, Dioxan und Tetrahydrofuran: Ketone wie Aceton, Methylethylketon, Methyliso propylketon und Methylisobutylketon; Nitrile wie Acetonitril, Propionitril und Benzonitril; Ester wie Ethylacetat und Amylacetat; Säureamide wie Dimethylformamid und Dimethylacetamid sowie Sulfone und Sulfoxide wie Dimethylsulfoxid und Sulfolan.Examples include aliphatic, alicyclic and aromatic hydrocarbons, which can optionally be chlorinated, such as hexane, cyclohexane, Petroleum ether, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene and chlorobenzene; Ethers such as diethyl ether, Methyl ethyl ether, diisopropyl ether, dibutyl ether, propylene oxide, Dioxane and tetrahydrofuran: ketones such as acetone, methyl ethyl ketone, methyl iso propyl ketone and methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile and Benzonitrile; Esters such as ethyl acetate and amyl acetate; Acid amides such as dimethylformamide and dimethylacetamide and sulfones and sulfoxides such as dimethyl sulfoxide and sulfolane.
Die Umsetzung kann innerhalb eines weiten Temperaturbereiches durchgeführt werden. Im allgemeinen wird sie bei einer Temperatur zwischen -20°C und 200°C, durchgeführt.The reaction can be carried out within a wide temperature range will. Generally, it is at a temperature between -20 ° C and 200 ° C.
Die Umsetzung wird unter dem Druck der Umgebung durchgeführt, wenngleich sie auch bei erhöhtem Druck oder vermindertem Druck durchgeführt werden könnte.The implementation is done under the pressure of the environment, albeit it could also be carried out at elevated pressure or reduced pressure.
Die Erzeugung des Fluorcarbens der Formel :CFR¹ erfolgt nach an sich bekannten Methoden (z. B. Wakselman et al. Synthesis 1985, 754). Beispielsweise werden für die Darstellung von Chlorfluorcarben die Salze der Dichlorfluoressigsäure in hochsiedenden Lösungsmitteln wie Diglyme, Triglyme und Tetraglyme verwendet. The fluorocarbon of the formula: CFR 1 is produced according to known per se Methods (e.g. Wakselman et al. Synthesis 1985, 754). For example, for the representation of chlorofluorocarbons in the salts of dichlorofluoroacetic acid high-boiling solvents such as diglyme, triglyme and tetraglyme are used.
Als Chlorfluorcarbendonatoren eignen sich beispielsweise Halogenfluorkohlen wasserstoffe wie Dichlorfluormethan und Alkalimetalldichlorfluoracetate wie Natriumdichlorfluoracetat.Halogen fluorocarbons, for example, are suitable as chlorofluorocarbon donors Hydrogen such as dichlorofluoromethane and alkali metal dichlorofluoroacetate such as Sodium dichlorofluoroacetate.
Die Erzeugung von Difluorcarben erfolgt nach in der Fachliteratur bekannten Methoden [z. B. Burton und Hahnfeld, Fluorine Chem. Rev. 2, 8 (1977), 119 ff].Difluorocarbons are produced according to the methods known in the specialist literature Methods [e.g. B. Burton and Hahnfeld, Fluorine Chem. Rev. 2, 8 (1977), 119 ff].
Als Difluorcarbenspender eignen sich beispielweise Alkalimetallchloridfluoracetate wie Natriumchlordifluoracetat, Halogendifluorkohlenwasserstoffe wie Chlordifluormethan; Organozinn-Verbindungen wie Trimethyl(trifluormethylzinn; Organoquecksilber-Verbindungen wie Bis(trifluormethyl)quecksilber; Organo phosphor-Verbindungen wie Tris(trifluormethyl)-difluorphosphoran und Triphenyl- (bromidfluormethyl)-phosphoniumbromid.Examples of suitable difluorocarbon donors are alkali metal chloride fluoroacetates such as sodium chlorodifluoroacetate, halogen difluorocarbons such as Chlorodifluoromethane; Organotin compounds such as trimethyl (trifluoromethyltin; Organomercury compounds such as bis (trifluoromethyl) mercury; Organo phosphorus compounds such as tris (trifluoromethyl) difluorophosphorane and triphenyl (bromide fluoromethyl) phosphonium bromide.
Die nach oben genannten Verfahren herstellbaren erfindungsgemäßen Verbindungen können nach den üblichen Verfahren aus dem Reaktionsgemisch isoliert werden, beispielsweise durch Abdestillieren des eingesetzten Lösungsmittels bei normalem, oder vermindertem Druck, durch Ausfällen mit Wasser oder durch Extraktion.The compounds according to the invention which can be prepared by the abovementioned processes can be isolated from the reaction mixture by the customary methods, for example by distilling off the solvent used in normal, or reduced pressure, by precipitation with water or by extraction.
Ein erhöhter Reinheitsgrad kann in der Regel durch säulenchromatographische Aufreinigung sowie durch fraktionierte Destillation oder Kristallisation erhalten werden.An increased degree of purity can usually be determined by column chromatography Purification and obtained by fractional distillation or crystallization will.
Die erfindungsgemäßen Verbindungen zeichnen sich durch gute insektizide und akarizide Wirkung aus und stellen damit eine wertvolle Bereicherung der Technik dar. Aufgrund ihrer Wirkung gegen eine weite Spanne saugender Arthropoden unterschiedlichster Verwandschaftsgruppen können die erfindungsgemäßen Verbindungen nicht gegen Schädlinge an Kulturpflanzen eingesetzt werden, sondern auch zur Bekämpfung von Parasiten des Menschen und der Nutztiere. Besondere Bedeutung hat die Wirkung der erfindungsgemäßen Verbindungen gegen Parasiten, die hinsichtlich anderer Mittel Resistenz entwickelt haben.The compounds according to the invention are notable for good insecticides and acaricidal effect and thus provide a valuable addition to the technology Because of their action against a wide range of absorbent arthropods The compounds according to the invention can be of very different kinship groups not used against pests on crops, but also to combat parasites of humans and farm animals. Special The effect of the compounds according to the invention against parasites is important, who have developed resistance to other agents.
Zu den Insekten und Milben, einschließlich tierischer Ektoparasiten, die erfindungsgemäß bekämpft werden können, gehören beispielsweise die Lepidopteren wie Plutella xylostella, Spodoptera littoralis, Heliothis armigera und Pieris brassicae; die Dipteren wie Musca domestica, Ceratitis capitata, Erioischia brassicae, Lucilia sericata und Aedes aegypti; die Homopteren einschließlich Blattläusen wie Megoura viciae und Nilaparvata lugens; die Coleopteren wie Phaedon cochleariae, Anthonomus grandis und Cornrootworm (Diabrotica spp., beispielsweise Diabrotica undecimpunctata); die Orthopteren wie Blattella germanica; die Zecken wie Boophilus microplus und die Läuse wie Damalinia bovis und Linognathus vituli sowie die Spinnmilben wie Tetranychus urticae und Panonychus ulmi, und Gallmilben wie Phyllocoptruta oleivora.To the insects and mites, including animal ectoparasites, according to the invention can be fought, for example, the Lepidoptera such as Plutella xylostella, Spodoptera littoralis, Heliothis armigera and Pieris brassicae; the dipteras such as Musca domestica, Ceratitis capitata, Erioischia brassicae, Lucilia sericata and Aedes aegypti; including the homopterans Aphids such as Megoura viciae and Nilaparvata lugens; the coleopteras like Phaedon cochleariae, Anthonomus grandis and Cornrootworm (Diabrotica spp., For example Diabrotica undecimpunctata); the orthoptera such as Blattella germanica; the ticks like Boophilus microplus and the lice like Damalinia bovis and Linognathus vituli and spider mites such as Tetranychus urticae and Panonychus ulmi, and gall mites such as Phyllocoptruta oleivora.
Die Anwendung der erfindungsgemäßen Verbindungen kann in Konzentrationen von 0,0005 bis 5,0%, vorzugsweise von 0,001 bis 0,1% erfolgen, worunter das Gewicht im Gramm Wirkstoff in 100 ml Zubereitung zu verstehen ist.The compounds according to the invention can be used in concentrations of 0.0005 to 5.0%, preferably 0.001 to 0.1%, including the weight in grams of active ingredient in 100 ml preparation.
Die erfindungsgemäßen Verbindungen können entweder allein, in Mischung miteinander oder mit anderen insektiziden Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel wie zum Beispiel Insektizide, Akarizide oder Fungizide, je nach dem gewünschten Zweck zugesetzt werden.The compounds according to the invention can either be used alone or in a mixture with one another or with other insecticidal agents. Possibly other pesticides or pesticides such as Example insecticides, acaricides or fungicides, depending on the desired purpose be added.
Eine Förderung der Wirkungsintensität und der Wirkungsgeschwindigkeit kann zum Beispiel durch wirkungssteigernde Zusätze wie organische Lösungsmittel, Netzmittel und Öle erzielt werden. Solche Zusätze lassen daher gegebenenfalls eine Verringerung der Wirkstoffdosierung zu.A promotion of the intensity and speed of impact can Example by adding additives such as organic solvents, wetting agents and oils can be obtained. Such additives may therefore have one Reduction of drug dosage too.
Als Mischungspartner können außerdem Phospholipide verwendet werden, zum Beispiel solche aus der Gruppe Phosphatidylcholin, den hydrierten Phosphatidylcholinen, Phosphatidylethanolamin, den N-Acyl-phosphatidylethanolaminen, Phos phatidylinosit, Phosphatidylserin, Lysolecithin und Phosphatidylglycerol.Phospholipids can also be used as mixing partners, for example those from the group phosphatidylcholine, the hydrogenated phosphatidylcholines, Phosphatidylethanolamine, the N-acylphosphatidylethanolamines, Phos phatidylinositol, phosphatidylserine, lysolecithin and phosphatidylglycerol.
Zweckmäßig werden die erfindungsgemäßen Wirkstoffe oder deren Mischungen in Form von Zubereitungen wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Träger stoffen beziehungsweise Verdünnungsmitteln und gegebenenfalls Haft-, Netz-, Emulgier- und Dispergierhilfsmitteln angewandt.The active compounds according to the invention or their mixtures are expediently used in Form of preparations such as powders, sprinkling agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers substances or diluents and, if necessary, adhesives, wetting agents, Emulsifying and dispersing aids applied.
Geeignete flüssige Trägerstoffe sind zum Beispiel aliphatische und aromatische Kohlenwasserstoffe wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethylsulfoxid, Dimethylformamid, weiterhin Mineralölfraktionen und Pflanzenöle.Suitable liquid carriers are, for example, aliphatic and aromatic Hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, Dimethylformamide, further mineral oil fractions and vegetable oils.
Als feste Trägerstoffe eignen sich Mineralien, zum Beispiel Tonsil, Silicagel, Talkum, Kaolin, Attapulgit, Kalkstein und pflanzliche Produkte, zum Beispiel Mehle.Minerals are suitable as solid carriers, for example Tonsil, silica gel, Talc, kaolin, attapulgite, limestone and herbal products, for example Flour.
An oberflächenaktiven Stoffen sind zum Beispiel zu nennen Calciumligninsulfonat, Polyethylenalkylphenylether, Naphthalinsulfonsäuren und deren Salze, Phe nolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzolsulfonsäuren und deren Salze.Examples of surface-active substances include calcium lignin sulfonate, Polyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, Phe nolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.
Der Anteil des bzw. der Wirkstoffe(s) in den verschiedenen Zubereitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 10 bis 90 Gewichtsprozente Wirkstoff, etwa 90 bis 10 Gewichtsprozente flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Gewichtsprozente oberflächenaktive Stoffe.The proportion of the active ingredient (s) in the different preparations can vary within wide limits. For example, the agents contain about 10 to 90 Weight percent active ingredient, about 90 to 10 weight percent liquid or solid Carriers and optionally up to 20 percent by weight surface-active Fabrics.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, zum Beispiel mit Wasser als Träger in Spritzbrühmengen von etwa 100 bis 3000 Liter/ha. Eine Anwendung der Mittel im sogenannten Low-Volume und Ultra-Low-Volume-Verfahren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikroganulaten. The funds can be applied in the customary manner, for example with Water as a carrier in spray liquor quantities of approximately 100 to 3000 liters / ha. A Use of the funds in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called micro-organics.
Zur Herstellung der Zubereitungen werden zum Beispiel die folgenden Bestandteile eingesetzt:For example, the following ingredients are used to prepare the preparations used:
-
A Spritzpulver
20 Gew.-% Wirkstoff
35 Gew.-% Bleicherde
8 Gew.-% Calciumsalz der Ligninsulfonsäure
2 Gew.-% Natriumsalze des N-Methyl-N-oleyl-taurins
35 Gew.-% KieselsäureA wettable powder 20 wt .-% active ingredient
35% by weight of bleaching earth
8% by weight calcium salt of lignin sulfonic acid
2% by weight of sodium salts of N-methyl-N-oleyl-taurine
35% by weight of silica -
B Paste
45 Gew.-% Wirkstoff
5 Gew.-% Natriumaluminiumsilikat
15 Gew.-% Cetylpolyglycolether mit 8 Mol Ethylenoxid
2 Gew.-% Spindelöl
10 Gew.-% Polyethylenglykol
23 Teile WasserB paste 45 wt .-% active ingredient
5% by weight sodium aluminum silicate
15% by weight of cetyl polyglycol ether with 8 moles of ethylene oxide
2% by weight spindle oil
10% by weight polyethylene glycol
23 parts of water -
C Emulsionskonzentrat
20 Gew.-% Wirkstoff
75 Gew.-% Isophoron
5 Gew.-% einer Mischung auf Basis des Natriumsalzes des N-Methyl-N-oleyl-taurins und des Calciumsalzes der LigninsulfonsäureGew.-% = GewichtsprozentC emulsion concentrate 20% by weight of active ingredient
75% by weight isophorone
5% by weight of a mixture based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignosulfonic acid
Die folgenden Beispiele beschreiben die Herstellung der erfindungsgemäßen Verbindungen.The following examples describe the preparation of the compounds according to the invention.
Eine Lösung von 9 g (0,035 mol) 5-Hexansäure-(2-naphthyl)-)methylester in 100 ml
Diglyme wird auf 162°C erhitzt. Innerhalb 1,5 Stunden tropft man eine Lösung
von 10,8 g (0,07 mol) Natriumchlordifluoracetat in 50 ml Diglyme hinzu und erhitzt
1 Stunde auf 190°C. Man läßt abkühlen, filtriert den ausgefallenen Feststoff
ab und engt das Filtrat unter vermindertem Druck ein. Das Rohprodukt wird
säulenchromatographisch an Kieselgel mit Hexan/Essigester 95 : 5 als Elutionsmittel
gereinigt.
Ausbeute: 6,5 g (61% der Theorie)
: 1,54130A solution of 9 g (0.035 mol) of 5-hexanoic acid (2-naphthyl) -) methyl ester in 100 ml of diglyme is heated to 162 ° C. A solution of 10.8 g (0.07 mol) of sodium chlorodifluoroacetate in 50 ml of diglyme is added dropwise over the course of 1.5 hours and the mixture is heated at 190 ° C. for 1 hour. The mixture is allowed to cool, the precipitated solid is filtered off and the filtrate is concentrated under reduced pressure. The crude product is purified by column chromatography on silica gel with hexane / ethyl acetate 95: 5 as the eluent.
Yield: 6.5 g (61% of theory)
: 1.54130
Zu einer Lösung von 2,5 g (0,07 mol) 4-(2,2-Difluorcyclopropyl)-butanol, 0,1 g
4-Dimethylaminopyridin, 2,3 ml (0,017 mol) Triethylamin in 30 ml Tetrahydrofuran
(THF) wird bei 0°C eine Lösung von 5 g (0,017 mol) Octadecansäurechlorid
in 30 ml THF zugetropft und 4 Stunden bei Raumtemperatur nachgerührt. Der ausgefallene
Feststoff wird abfiltriert und das Filtrat bei vermindertem Druck
eingeengt. Der Rückstand wird in Essigester aufgenommen, zweimal mit Wasser gewaschen,
über Magnesiumsulfat getrocknet und eingeengt. Das Rohprodukt wird
säulenchromatographisch an Kieselgel mit Hexan/Essigester 8 : 2 als Elutionsmittel
gereinigt.
Ausbeute: 4,7 g (67% der Theorie)
Schmelzpunkt: 27°C
To a solution of 2.5 g (0.07 mol) of 4- (2,2-difluorocyclopropyl) butanol, 0.1 g of 4-dimethylaminopyridine, 2.3 ml (0.017 mol) of triethylamine in 30 ml of tetrahydrofuran (THF) a solution of 5 g (0.017 mol) of octadecanoic acid chloride in 30 ml of THF is added dropwise at 0 ° C. and the mixture is subsequently stirred at room temperature for 4 hours. The precipitated solid is filtered off and the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate, washed twice with water, dried over magnesium sulfate and concentrated. The crude product is purified by column chromatography on silica gel with hexane / ethyl acetate 8: 2 as the eluent.
Yield: 4.7 g (67% of theory)
Melting point: 27 ° C
In analoger Weise lassen sich die folgenden Verbindungen herstellen:The following connections can be made in an analogous manner:
Die nachfolgenden Anwendungsbeispiele belegen die biologische Wirksamkeit der erfindungsgemäßen Verbindungen.The following application examples demonstrate the biological effectiveness of compounds of the invention.
Aus entwickelten Primärblättern der Buschbohne (Phaseolus vulgaris nanus Aschers.) werden runde Blattscheiben mit einem Durchmesser von 24 mm gestanzt und unbehandelt bzw. nach Tauchbehandlung mit einer 0,1%igen wäßrigen Zubereitung des Wirkstoffs auf nasses Fließpapier gelegt, wobei die Blattunterseite nach oben gerichtet ist. Nach Antrocknen der so behandelten Proben werden ungeflügelte Stadien von Aphis fabae aufgesetzt (etwa 100 pro Blattscheibe) bei drei Wiederholungen. Die Blattscheiben werden auf naß gehaltenem Filterpapier zwei Tage bei 25°C und 16 h/Tag bei Licht aufgestellt. Dann wird die prozentuale Mortalität geschätzt und unter Bezug auf die unbehandelte Kontrolle die Wirkung nach Abbott berechnet.From developed primary leaves of the bush bean (Phaseolus vulgaris nanus Aschers.) Round leaf discs with a diameter of 24 mm are punched and untreated or after immersion treatment with a 0.1% aqueous preparation of the active ingredient placed on wet blotting paper, with the underside of the sheet is directed upwards. After the samples treated in this way have dried, they are wingless Stages of Aphis fabae (approximately 100 per leaf disc) three repetitions. The leaf disks are placed on filter paper kept wet set up for two days at 25 ° C and 16 h / day with light. Then the percentage Mortality is estimated and related to the untreated control Effect calculated according to Abbott.
Die erfindungsgemäßen Verbindungen gemäß den Beispielen 1, 3, 4, 5, 7, 20-24 und 26-29 zeigen eine Wirkung von 80% oder mehr.The compounds according to the invention according to Examples 1, 3, 4, 5, 7, 20-24 and 26-29 show an effect of 80% or more.
Reissämlinge (Oryza sativa L.) im Zweiblattstadium (etwa 10 je Polystyroltopf von 6,5×6,5 cm) werden unbehandelt bzw. nach Tauchbehandlung mit 0,1% Wirkstoff enthaltender wäßriger Zubereitung bis zum Antrocknen der Flüssigkeit gestülpt, durch dessen obere Öffnung etwa 30 mit Kohlendioxid betäubte Individuen von Nilaparvata lugens im 4.-5. Stadium eingebracht werden. Nach Verschließen der Öffnung mit einem engmaschigen Sieb werden die Töpfe zwei Tage lang bei 28°C und 16 h/Tag bei Licht gehalten. Dann wird die prozentuale Mortalität bestimmt und unter Bezug auf die unbehandelte Kontrolle die Wirkung nach Abbott berechnet.Rice seedlings (Oryza sativa L.) in the two-leaf stage (about 10 per polystyrene pot of 6.5 × 6.5 cm) are untreated or after immersion treatment with 0.1% active ingredient containing aqueous preparation put on until the liquid dries, through its upper opening, about 30 individuals anesthetized with carbon dioxide Nilaparvata lugens in the 4th-5th Stage. After closing the The pots are opened with a close-meshed sieve at 28 ° C for two days and kept in light for 16 h / day. The percentage mortality is then determined and calculated the Abbott effect based on the untreated control.
Die erfindungsgemäßen Verbindungen gemäß den Beispielen 4, 16, 17, 24 und 27 zeigten eine Wirkung von 80% oder mehr.The compounds according to the invention according to Examples 4, 16, 17, 24 and 27 showed an effect of 80% or more.
Aus entwickelten Primärblättern der Buschbohne (Phaseolus vulgaris nanus Aschers.) werden runde Blattscheiben mit einem Durchmesser von 14 mm gestanzt und unbehandelt bzw. nach Tauchbehandlung mit einer 0,1% Wirkstoff enthaltenen wäßrigen Zubereitung auf nasses Filterpapier gelegt, wobei die Blattunterseite nach oben gerichtet ist. Nach Antrocknen der so behandelten Proben werden sechs erwachsene Weibchen von Tetranychus urticae auf jede Blattscheibe gesetzt und für 3 Tage bei 25°C und 16 h/Tag bei Licht gehalten (vier Wiederholungen). Dann werden die toten und lebenden Weibchen gezählt und entnommen. Gleichfalls werden die abgelegten Eier gezählt. Nach weiteren sieben Tagen werden die lebenden Larven gezählt, und unter Bezug auf die unbehandelte Kontrolle wird die Gesamtwirkung nach Abbott berechnet.From developed primary leaves of the bush bean (Phaseolus vulgaris nanus Aschers.) Round leaf disks with a diameter of 14 mm are punched and untreated or after immersion treatment with a 0.1% active ingredient aqueous preparation placed on wet filter paper, with the underside of the leaf is directed upwards. After the samples treated have dried on six adult females of Tetranychus urticae placed on each leaf disc and kept for 3 days at 25 ° C and 16 h / day in the light (four repetitions). Then the dead and living females are counted and removed. Likewise the laid eggs are counted. After another seven days, the live larvae are counted, and referring to the untreated control the overall effect calculated according to Abbott.
Die erfindungsgemäßen Verbindungen gemäß den Beispielen 1-29 zeigten eine 80-100%ige Gesamtwirkung.The compounds according to the invention according to Examples 1-29 showed one 80-100% overall effect.
Aus entwickelten Primärblättern der Buschbohne (Phaseolus vulgaris nanus Aschers.) werden runde Blattscheiben mit einem Durchmesser von 14 mm gestanzt und mit abwärts gerichteter Oberseite auf nasses Filterpapier gelegt. Je Blattscheibe werden mindestens 5 adulte Weibchen von Tetranychus urticae aufgesetzt und für 2 Tage bei etwa 25°C, 50-60% relativer Luftfeuchte und 16 Stunden Licht pro Tag gehalten. Nach dem Absammeln der Adulten werden die Blattscheiben mit den abgelegten Eiern in eine 0,064% Wirkstoff und Netzmittel enthaltende Zubereitung getaucht. Als Kontrolle werden Blattscheiben in Wasser getaucht, wobei das Netzmittel in gleicher Konzentration wie in der Wirkstoff enthaltenden Zubereitung enthalten ist. Nach Zählung der Eier werden die Blattscheiben für 7 Tage bei etwa 25°C, 50-60% relativer Luftfeuchte und 16 Stunden Licht pro Tag gehalten. Aus der prozentualen Differenz abgelegter Eier und lebender Larven wird unter Bezug auf die Kontrolle nach Abbott die Wirkung berechnet. Der Durchschnitt ergibt sich aus drei Wiederholungen.From developed primary leaves of the bush bean (Phaseolus vulgaris nanus Aschers.) Round leaf disks with a diameter of 14 mm are punched and placed on wet filter paper with the top down. Per leaf disc at least 5 adult Tetranychus urticae females are placed and for 2 days at about 25 ° C, 50-60% relative humidity and 16 hours Light kept per day. After collecting the adults, the leaf disks become with the laid eggs in a 0.064% active ingredient and wetting agent Preparation dipped. As a control, leaf disks are immersed in water, wherein the wetting agent in the same concentration as in the active ingredient Preparation is included. After counting the eggs, the leaf disks for 7 days at about 25 ° C, 50-60% relative humidity and 16 hours of light held per day. From the percentage difference between laid eggs and live eggs Larvae are calculated with reference to the Abbott control. The average is three repetitions.
Die Verbindungen gemäß den Beispielen 1-3, 5-12 und 15-18 zeigten eine Wirkung von 80% oder mehr.The compounds according to Examples 1-3, 5-12 and 15-18 showed an effect of 80% or more.
Die erfindungsgemäßen Verbindungen werden als wäßrige Zubereitung mit einer Wirkstoffkonzentration von 0,1% eingesetzt. Von diesen Wirkstoffzubereitungen werden 0,2 ml auf den Boden einer Polystyrolpetrischale sowie auf den darin enthaltenen Maiskeimling und auf die im Schalenzentrum befindlichen ca. 50 Eier des Maiswurzelwurms (Diabrotica undecimpunctata) pipettiert. Die verschlossenen Schalen werden für 4-7 Tage bei 25°C unter Langtagbedingungen aufgestellt. Kriterium für die Wirkungsbeurteilung ist die Abtötung von Eiern oder der frisch schlüpfenden Larven bei Versuchsende.The compounds of the invention are used as an aqueous preparation with a Active ingredient concentration of 0.1% used. Of these drug preparations 0.2 ml on the bottom of a polystyrene petri dish and on the inside contained corn seedling and on the approx. 50 eggs located in the shell center of the corn rootworm (Diabrotica undecimpunctata). The locked ones Trays are set up for 4-7 days at 25 ° C under long day conditions. The criterion for the effectiveness assessment is the killing of eggs or the freshly hatching larvae at the end of the experiment.
Die erfindungsgemäßen Verbindungen gemäß den Beispielen 5 und 20 erzielten eine 80-100%ige Wirkung. The compounds according to the invention according to Examples 5 and 20 achieved one 80-100% effect.
Die erfindungsgemäßen Verbindungen werden als wäßrige Zubereitungen mit einer Wirkstoffkonzentration von 0,1% eingesetzt. In diese Wirkstoffzubereitungen werden einen Tag alte Eiablagen, die von befruchteten Falterweibchen auf Filterpapier abgesetzt worden waren, bis zur völligen Benetzung getaucht und für 4 Tage bei 25°C unter Langtagbedingungen in geschlossenen Petrischalen deponiert. Kriterium für die Wirkungsbeurteilung ist die prozentuale Schlupfverhinderung im Vergleich zu unbehandelten Eiablagen.The compounds of the invention are used as aqueous preparations with a Active ingredient concentration of 0.1% used. In these drug preparations are one day old egg-laying, that of fertilized female butterflies Filter paper had been removed, dipped and soaked until completely wetted for 4 days at 25 ° C under long day conditions in closed petri dishes deposited. The criterion for the effectiveness assessment is the percentage slip prevention compared to untreated egg laying.
Die erfindungsgemäßen Verbindungen gemäß den Beispielen 5, 11, 12, 20 und 28 erzielten eine 80-100%ige Wirkung.The compounds according to the invention according to Examples 5, 11, 12, 20 and 28 achieved an 80-100% effect.
Claims (8)
R¹ Fluor, Chlor oder Wasserstoff bedeutet,
A die Gruppe -COOR², -CONR²R³, -CH₂OR⁴ oder -COOCH₂CONR²R³, wobei
R² und R³ unabhängig voneinander für Wasserstoff, C1-20-Alkyl, C2-20-Alkenyl, C2-20-Alkinyl, C1-10-Alkoxy-C1-10-alkyl, C1-10-Halogenalkyl, Halogencyclopropyl-C1-9-alkylcarboxy-C2-10-alkyl, Halogencyclopropyl-C1-9-alkylcarboxy-C2-6-alkoxy-C2-6-alkyl, Aryl-C1-3-alkyl, Aryl-C2-4-alkenyl, Aryl-C2-4-alkinyl, Halogenaryl-C1-3-alkyl, Halogenaryl-C2-4-alkenyl, Aryloxyaryl-C1-3-alkyl, Aryloxyaryl-C2-4-alkenyl, C1-10-Alkylaryl-C1-3-alkyl, C1-10-Alkylaryl-C2-4-alkenyl,
C1-10-Alkoxyaryl-C1-3-alkyl, C1-10-Alkoxyaryl-C2-4-alkenyl, C2-6-Alkenoxyaryl-C2-4-alkenyl, C2-6-Alkinoxyaryl-C2-4-alkenyl, Halogencyclopropyl-C1-4-alkylcarboxyaryl, Halogencyclopropyl-C1-4-alkylcarboxyaryl-C2-4-alkenyl, unsubstituiertes Aryl oder durch C1-20-Alkyl, Halogen-C1-6-alkyl, C1-16- Alkoxy, Halogen-C1-6-alkoxy, Phenyl-C1-6-alkyl, Phenyl-C1-6-alkoxy, C3-10- Cycloalkoxy, Halogen-C3-10-cycloalkenyloxy, Halogen-C2-6-alkenyloxy, C2-6- Alkinyloxy, Halogen-C2-6-alkinyloxy, Aryl-C1-6-alkoxy, Halogen, Amino, Cyano, Hydroxy, Nitro, Aryloxy, Heteroaryloxy, Halogenaryloxy, Arylamino, Halogenarylamino, C1-6-Alkoxycarbonyl, C1-6-Alkoxycarbonylmethyl, Halogen- C1-6-alkoxycarbonyl, C1-2-Alkyldioxy, C1-6-Alkylthio, C1-6-Alkylamino, Di-C1-6-alkylamino, ein- oder mehrfach substituiertes Aryl, freies Heteroaryl, durch Halogen, C1-3-Alkyl oder Halogen-C1-3-alkyl substituiertes Heteroaryl, wobei
R² und R³ gemeinsam mit dem Stickstoffatom einen gesättigten, teilgesättigten oder ungesättigten verzweigten oder unverzweigten heterocyclischen Ring bilden können, und
falls A für die Gruppe -COOR² steht, bedeutet R² auch ein Alkalimetallatom oder ein Äquivalent eines zweiwertigen Metalls oder unsubstituiertes oder durch C1-10-Alkyl ein- oder mehrfach substituiertes Ammonium, und
R⁴ Wasserstoff oder den Rest bedeuten und
n für eine gerade Zahl zwischen 2 und 20 steht.1. Halocyclopropylalkyl derivatives of the general formula I wherein
R¹ is fluorine, chlorine or hydrogen,
A the group -COOR², -CONR²R³, -CH₂OR⁴ or -COOCH₂CONR²R³, wherein
R² and R³ independently of one another are hydrogen, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 1-10 -alkoxy-C 1-10 -alkyl, C 1-10 -haloalkyl, Halocyclopropyl-C 1-9 -alkylcarboxy-C 2-10 -alkyl, halocyclopropyl-C 1-9 -alkylcarboxy-C 2-6 -alkoxy-C 2-6 -alkyl, aryl-C 1-3 -alkyl, aryl- C 2-4 alkenyl, aryl-C 2-4 -alkynyl, haloaryl-C 1-3 alkyl, haloaryl-C 2-4 alkenyl, aryloxyaryl-C 1-3 alkyl, aryloxyaryl-C 2-4 - alkenyl, C 1-10 -alkylaryl-C 1-3 -alkyl, C 1-10 -alkylaryl-C 2-4 -alkenyl,
C 1-10 alkoxyaryl-C 1-3 alkyl, C 1-10 alkoxyaryl-C 2-4 alkenyl, C 2-6 alkenoxyaryl-C 2-4 alkenyl, C 2-6 alkynoxyaryl-C 2-4 -alkenyl, halocyclopropyl-C 1-4 -alkylcarboxyaryl, halocyclopropyl-C 1-4 -alkylcarboxyaryl-C 2-4 -alkenyl, unsubstituted aryl or by C 1-20 alkyl, halo-C 1-6 alkyl , C 1-16 -alkoxy, halo-C 1-6 -alkoxy, phenyl-C 1-6 -alkyl, phenyl-C 1-6 -alkoxy, C 3-10 - cycloalkoxy, halo-C 3-10 -cycloalkenyloxy , Halo-C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, halo-C 2-6 -alkynyloxy, aryl-C 1-6 -alkoxy, halogen, amino, cyano, hydroxy, nitro, aryloxy, heteroaryloxy, haloaryloxy , arylamino, haloarylamino, C 1-6 alkoxycarbonyl, C 1-6 alkoxycarbonylmethyl, halo C 1-6 alkoxycarbonyl, C 1-2 -Alkyldioxy, C 1-6 alkylthio, C 1-6 alkylamino, di -C 1-6 -alkylamino, mono- or polysubstituted aryl, free heteroaryl, heteroaryl substituted by halogen, C 1-3 -alkyl or halogen-C 1-3 -alkyl, where
R² and R³ together with the nitrogen atom can form a saturated, partially saturated or unsaturated branched or unbranched heterocyclic ring, and
if A stands for the group -COOR², R² also denotes an alkali metal atom or an equivalent of a divalent metal or unsubstituted or monosubstituted or polysubstituted by C 1-10 -alkyl, and
R⁴ hydrogen or the rest mean and
n stands for an even number between 2 and 20.
R¹ und n die in Formel I angegebene Bedeutung haben und
X für Hydroxy, Chlor oder Brom steht, als Zwischenprodukte zur Herstellung von Verbindungen der Formel I.3. Compounds of the general formula II wherein
R¹ and n have the meaning given in formula I and
X represents hydroxy, chlorine or bromine, as intermediates for the preparation of compounds of the formula I.
R¹ und n die in Formel I angegebene Bedeutung haben und
Y für Hydroxy oder Brom steht, als Zwischenprodukte zur Herstellung von Verbindungen der Formel I.4. Compounds of the general formula III in the
R¹ and n have the meaning given in formula I and
Y represents hydroxy or bromine, as intermediates for the preparation of compounds of the formula I.
- a) Verbindungen der allgemeinen Formel IV CH₂=CH-CH₂-(CH₂)n-A (IV)in der A und n die in Formel I angegebenen Bedeutungen haben, in Gegenwart eines inerten Lösungsmittels mit einem Halogencarben Formel:CFR¹,in der R¹ die in Formel I angegebene Bedeutung hat, reagieren läßt, oder
- b) falls A in Formel I die Gruppe
-COOR²darstellt, Verbindungen der allgemeinen Formel II
in der
R¹ und n die in Formel I angegebene Bedeutung haben und
X für Hydroxy, Chlor oder Brom steht, mit einer Hydroxyverbindung der Formel R²OH, worin R² die in Formel I angegebene Bedeutung hat, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oder - c) falls A in Formel I die Gruppe -CONR²R³bedeutet, Verbindungen der allgemeinen Formel II, worin R¹ und n die in Formel I angegebene Bedeutung haben und X Chlor oder Brom bedeutet, mit einem Amin der FormelHNR²R³,in der R² und R³ die in Formel I angegebene Bedeutung haben, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oder
- d) falls A in Formel I die Gruppe
-COOCH₂CONR²R³bedeutet, Verbindungen der allgemeinen Formel II, worin R¹ und n die in
Formel I angegebene Bedeutung haben und X für Hydroxy steht, mit einer
Verbindung der allgemeinen Formel VIIIR²R³NCOCH₂Z (VIII)in der
R² und R³ die in Formel I angegebene Bedeutung haben und
Z für Chlor oder Brom steht, gegebenenfalls unter Verwendung eines Lösungsmittels sowie eines Säureacceptors umsetzt, oder - e) falls A in Formel I die Gruppe -CH₂OR⁴bedeutet, Verbindungen der allgemeinen Formel III, in der Y für Hydroxy steht, mit einer Verbindung der allgemeinen FormelR²COX,in der R² die in Formel I und X die in Formel II angegebene Bedeutung haben, gegebenenfalls unter Verwendung eines Lösungsmittels, eines Säureacceptors oder eines wasserentziehenden Mittels umsetzt.
- a) Compounds of the general formula IV CH₂ = CH-CH₂- (CH₂) n -A (IV) in which A and n have the meanings given in formula I, in the presence of an inert solvent with a halocarbene Formula: CFR¹, in which R¹ has the meaning given in formula I, can react, or
- b) if A in formula I represents the group -COOR², compounds of general formula II in the
R¹ and n have the meaning given in formula I and
X represents hydroxy, chlorine or bromine, with a hydroxy compound of the formula R²OH, in which R² has the meaning given in formula I, optionally using a solvent and an acid acceptor, or - c) if A in formula I means the group -CONR²R³, compounds of the general formula II, in which R¹ and n have the meaning given in formula I and X is chlorine or bromine, with an amine of the formula HNR²R³, in which R² and R³ have the formula I have the meaning given, optionally using a solvent and an acid acceptor, or
- d) if A in formula I means the group -COOCH₂CONR²R³, compounds of the general formula II, in which R¹ and n have the meaning given in formula I and X is hydroxy, with a compound of the general formula VIIIR²R³NCOCH₂Z (VIII) in the
R² and R³ have the meaning given in formula I and
Z represents chlorine or bromine, if appropriate using a solvent and an acid acceptor, or - e) if A in formula I means the group -CH₂OR⁴, compounds of the general formula III in which Y is hydroxy, with a compound of the general formula R²COX in which R² has the meaning given in formula I and X as defined in formula II, if appropriate using a solvent, an acid acceptor or a dehydrating agent.
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