KR880011189A - 13β-carbamoyloxymilbemycin derivatives useful for controlling parasites in animals and plants - Google Patents

Abstract

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13β-carbamoyloxymilbemycin derivatives useful for controlling parasites in animals and plants

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Claims (15)

A compound of formula (I) Wherein R ₁ is hydrogen or silyl or acyl, R ₂ is methyl, ethyl isopropyl or secondary butyl, R ₃ is straight or branched C ₁ -C ₁₈ alkyl, C ₃ -C ₁₀ cycloalkyl, C _2- Substituted or unsubstituted groups selected from the group aqueous with C ₆ alkenyl, C ₃ -C ₁₀ cycloalkenyl phenyl and naphthyl or R ₄ are groups defined by hydrogen or R ₃ . The compound of claim 1, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, R ₃ is halogen, C ₁ -C ₄ alkoxy, acyloxy; Or C ₁ -C ₁₈ unsubstituted or substituted as unsubstituted phenyl or naphthal groups, respectively, substituted or unsubstituted as halogen, C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxy, C ₁ -C ₂ haloalkyl or nitro. Alkyl; Or substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl with halogen and / or C ₁ -C ₄ alkyl; Or C ₂ -C ₆ alkenyl unsubstituted or substituted with halogen; Or substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl with halogen and / or C ₁ -C ₄ alkyl and R ₄ is hydrogen. The compound of claim 2, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, and R ₃ is substituted or unsubstituted C ₁ -C ₈ alkyl, phenyl or naphthyl Or C ₅ -C ₇ cycloalkyl, C ₂ -C ₆ alkenyl and C ₅ -C ₇ cyclo alkenyl, and R ₄ is hydrogen. The compound of claim 2, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, and R ₃ is halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ And phenyl or naphthyl, each substituted or unsubstituted as alkylthio, C ₁ -C ₄ haloalkyl or nitro, and R ₄ is hydrogen. The compound of claim 4, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, and R ₃ is bromine, chlorine, fluorine, C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxy, C Or phenyl or naphthyl, each substituted or unsubstituted as _1- C ₂ haloalkyl or nitro, and R ₄ is hydrogen. The compound of claim 5, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl isopropyl or secondary butyl, and R ₃ is phenyl or bromine, chlorine, fluorine C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxy, tri A compound which is phenyl substituted as fluoromethyl or nitro or unsubstituted naphthyl. The compound of claim 2, wherein R ₁ is substituted with hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, and R ₃ is halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ acyloxy Substituted C ₁ -C ₈ alkyl or phenyl substituted with phenyl or halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl or nitro, and R ₄ is R ₃ Compounds that are groups as defined in 8. A compound according to claim 7, wherein R ₁ is hydrogen, R ₂ is methyl, ethyl, isopropyl or secondary butyl, R ₃ is C ₁ -C ₈ alkyl, or phenyl, and R ₄ is defined in R ₃ . Compounds that are the same group. 13β-N-methylcarbomoyloxymilbemycin D, 13β-N-methylcarbomoyloxymilbemycin A ₃ , 13β-N-methylcarbomoyloxymilbemycin A ₄ , 13β-N -N-tert-butylcarbomoyloxymilbemycin D, 13β-N-tert-butylcarbomoyloxymilbemycin A ₃ , 13β-N-tert-butylcarbomoyloxymilbemycin A ₄ , 13β-N -Phenylcarbomoyloxymilbemycin D, 13β-N-phenylcarbomoyloxymelbemycin A ₃ , 13β-N-phenylcarbomoyloxymilbemycin A ₄ , 13β-N, N-dimethylcarbomoyloxymilbe Mycin D, 13β-N, N-dimethylcarbomoyloxymilbemycin A ₃ , 13β-N, N-dimethylcarbomoyloxymilbemycin A ₄ , 13β-N, N-diisopropylcarbomoyloxymilbe Mycin D, 13β-N, N-diisopropylcarbomoyloxymilbemycin A ₃ , 13β-N, N-diisopropylcarbomoyloxymilbemycin A ₃ A compound selected from the group consisting of. The 5-O-tert-butyldimethylsilyl-13β-N-methylcarbamoyloxymilbemycin D, 5-O-tert-butyldimethylsilyl-13β-N-methylcarbamoyloxy Milbemycin A ₃ , 5-O-tert-butyldimethylsilyl-13β-N-methylcarbamoyloxymilbemycin A ₄ , 5-O-tert-butyldimethylsilyl-13β-N-tert-butylcarb Bamoyloxymilbemycin D, 5-O-tert-butyldimethylsilyl-13β-N-tert-butylcarbamoyloxymilbemycin A ₃ , 5-O-tert-butyldimethylsilyl-13β-N- Tert-butylcarbamoyloxymilbemycin A ₄ , 5-O-tert-butyldimethylsilyl-13β-N-phenylcarbamoyloxymilbemycin D, 5-O-tert-butyldimethylsilyl-13β- N-phenylcarbamoyloxymilbemycin A ₃ , 5-O-tert-butyldimethylsilyl-13β-N-phenylcarbamoyloxymilbemycin A ₄ , 5-O-tert-butyldimethylsilyl-13β- N, N-dimethylcarbamoyloxymilbemycin D, 5-O-tert-butyldimethylsilyl-13β-N, N-dimethylcarbamoyloxymilbemycin A ₃ , 5-O-tertiary- Butyldimethylsilyl-13β-N, N-dimethylcarbamoyloxymilbemycin A ₄ , 5-O-tert-butyldimethylsilyl-13β-N, N-diisopropylcarbamoyloxymilbemycin D, 5- O-tert-butyldimethylsilyl-13β-N, N-diisopropylcarbamoyloxymilbemycin A ₃ , 5-O-tert-butyldimethylsilyl-13β-N, N-diisopropylcarbamoyl A compound selected from the group consisting of oxymilbemycin A4. When allyl alcohol of the following general formula (II) needs to be reacted with a reagent suitable for introducing the 13β-carbamoyloxy group R _3- (CO) O-, and then a product having a free 5-hydroxy group is necessary. Hydrolyze to remove protecting group R ₁ to prepare compound of formula (I) wherein R ₄ is hydrogen; Or a 13β-carbomoyloxy group as an alcohol alcohol of the following general formula (II) If necessary to react with a reagent suitable for introducing and then to obtain a product having a free 5-hydroxy group, it is hydrolyzed to remove the protecting group R ₁ so that R ₄ has one of the meanings defined in R ₃ . Preparing the compound of (I); Or a protecting group R ₁ and then by hydrolysis followed, if it is necessary to give the general formula (Ⅴ) compounds the following general formula (Ⅵ) 1 primary or secondary amine and the addition product is reacted with a free 5-hydroxy group of Process for preparing a compound of formula (I) In formula (I), R ₁ is hydrogen or silyl or acyl group, R ₂ is methyl, ethyl, isopropyl or secondary butyl, R ₃ is straight chain or C ₁ -C ₁₈ alkyl, C ₃ -C ₁₀ cyclo A substituted or unsubstituted group selected from the group consisting of alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₁₀ cycloalkenyl, phenyl and naphthyl, and R ₄ is defined as hydrogen or R ₃ In the above formulas (II), (V) and (VI), R ₁ is a protecting group, R ₂ , R ₃ and R ₄ are the groups defined in formula (I). A pesticide composition containing at least one compound of the general formula (I) as a conventional formulation adjuvant and an active ingredient. Wherein R ₁ is hydrogen or silyl or acyl, R ₂ is methyl, ethyl, isopropyl or secondary butyl, R ₃ is straight or branched C ₁ -C ₁₈ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ Is a substituted or unsubstituted group selected from the group consisting of -C ₆ alkenyl, C ₃ -C ₁₀ cycloalkenyl, phenyl and naphthyl, and R ₄ is groups defined as hydrogen or R ₃ . 13. A composition according to claim 12, containing at least one compound of the general formula (I) according to any one of claims 2 to 10 as a conventional formulation adjuvant and active ingredient. A method of controlling pests parasitic to animals and plants by using an amount of a compound of the following general formula (I) in an effective amount of a pesticide in a parasite, a plant or an animal, and a parasite habitat. Wherein R ₁ is hydrogen or silyl or acyl, R ₂ is methyl, ethyl, isopropyl or secondary butyl, R ₃ is straight or branched C ₁ -C ₁₈ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₂ Is a substituted or unsubstituted group selected from the group consisting of -C ₆ alkenyl, C ₁ -C ₁₀ cycloalkenyl, phenyl and naphthyl, and R ₄ is as defined as hydrogen or R ₃ . The method according to claim 14, wherein the compound of formula (I) as claimed in any one of claims 2 to 10 is used in an amount of agrochemically effective amount. ※ Note: The disclosure is based on the initial application.