KR850000425A - Herbicides 5-amino-3-oxo-4- (substituted-phenyl) -2,3-dihydrofuran and derivatives thereof - Google Patents

Abstract

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Description

Herbicides 5-amino-3-oxo-4- (substituted-phenyl) -2,3-dihydrofuran and derivatives thereof

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Claims (63)

1) A compound having the formula Wherein R is lower alkyl, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl, 1 to 4 carbon atoms and 1 to 3 selected from the group of fluoro, chloro, bromo or iodo, respectively Haloalkyl having two halo atoms, haloalkenyl having two to four carbon atoms and one to three halo atoms each selected from the group of fluoro, chloro, bromo or iodo, and lower alkoxy, Lower alkoxythio, alkyl and alkoxy when alkyl and alkoxy have 1 to 3 carbon atoms each, alkyl alkoxy when alkyl have 1 to 3 carbon atoms, and phenyl and naphth-1- Arylalkylene when one, inden-1-yl, 4-fluorophenyl, the alkylene component has 1 to 3 carbon atoms, and the aryl component is phenyl, naphth-1-yl or inden-1-yl , Or R is an aryl or substituted arylalkylene selected from the group having the following formula substituted, Wherein one, two or three of R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are lower alkyl, lower alkoxy, halo, nitro or 1-3 carbon atoms and 1-3 Is selected from the group of haloalkyl having the same or different halo atoms, the remainder being hydrogen, R ³ is a single bond or alkylene having 1 to 3 carbon atoms, and R ¹ is hydrogen or 1 to 4 carbon atoms Is alkyl, R ² is hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxy carbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl, R ¹ and R ² may be together bonded to the nitrogen atom a saturated 3 to 6 carbon atoms or having from one double to form the unsaturated nitrogen heterocyclic ring is nitrogen and the remainder are carbon atoms, X is hydrogen, lower alkyl Lower alkoxy, halo or trifluoromethine, and may be at any available position on the phenyl ring, Y is lower alkyl, lower alkoxy, halo, equal to 1 to 4 carbon atoms and 1 to 3 Lower haloalkyl having other halo atoms, lower haloalkoxy having 1 to 4 carbon atoms and 1 to 3 identical or different halo atoms, or 1 to 3 carbon atoms or 1 to 3 same or different Is a lower haloalkylthio having a halo atom and is conditionally that Y is halo wherein R, R ¹ and R ² are not all hydrogen, Y is other than trifluoromethyl, and X is other than hydrogen. Conditionally, R ¹ and R ² are each hydrogen and R is methyl, ethyl, propyl, 2-halophenyl, 2-lower alkylphenyl, or 4-fluorophenyl, and suitable salts thereof. The compound of claim 1 when one of R ¹ or R ² is hydrogen, methyl, ethyl or propyl. The compound of claim 1, wherein one of R 'and R ² is methyl or ethyl and the other is hydrogen, methyl or ethyl. The compound of claim 1 when one of R 'or R ² is hydrogen and the other is methyl, ethyl or propyl. The compound of claim 1 where X is hydrogen. The compound of claim 2 when X is hydrogen. The compound of claim 3 wherein X is hydrogen. The compound of claim 1 when R is phenyl, naphth-1-yl, 4-fluorophenyl or substituted aryl. The compound of claim 8 when R is phenyl, naphthyl or monosubstituted phenyl. The compound of claim 9 when R is phenyl, halophenyl or lower alkylphenyl. The compound of claim 10 when R is phenyl, 4-fluorophenyl, 2-halophenyl, or 2-lower alkylphenyl. The compound of claim 11 where X is hydrogen and R ¹ and R ² are each selected from the group of hydrogen, methyl or ethyl. The compound of claim 1 where R is lower alkyl, cycloalkyl, lower alkenyl, haloalkyl or haloalkenyl. The compound of claim 13 when one of R ¹ or R ² is hydrogen, methyl or ethyl and the other is methyl or ethyl. The compound of claim 14 when R is methyl, ethyl or propyl. The compound of claim 15 when one of R ¹ or R ² is hydrogen and the other is methyl or ethyl. The compound of claim 16 when X is hydrogen. As a compound having the formula Wherein R is lower alkyl, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl, 1 to 4 carbon atoms and 1 to 3 halo atoms each selected from the group of fluoro, chloro, bromo or iodo Haloalkyl having 2 to 4 carbon atoms and alloalkenyl, lower alkoxy, lower alkylthio, alkyl and alkoxy having 2 to 4 carbon atoms and 1 to 3 halo atoms each selected from the group of fluoro, chloro, bromo or iodo Lower alkoxyalkyl when the component has 1 to 3 carbon atoms each, lower alkylthioalkyl when the alkyl component has 1 to 3 carbon atoms each, phenyl, naphth-1-yl, inden-1-yl, 4 Fluorophenyl, an alkylene component having 1 to 3 carbon atoms, the aryl component being phenyl, naphth-1-yl inden-1-yl or arylalkylene or R is substituted aryl or Substituted arylalkylene selected from the group having the formula: Wherein one, two or three of R ⁴ R ⁵ , R ⁷ , R ⁸ and R ⁹ are each lower alkyl, lower alkoxy, halo, nitro or one to three carbon atoms and one to three equal or different halo atoms Is haloalkyl, the remainder is hydrogen, R ³ is a single bond or alkene having 1 to 3 carbon atoms, R ¹ is hydrogen or alkyl having 1 to 4 carbon atoms, R ² is hydrogen, 1 to Alkyl having 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxy-carbonylalkyl, lower alkoxy-alkyl or lower alkylthioalkyl, R ¹ and R ² together being bonded to a nitrogen atom, Form a saturated or unsaturated nitrogen heterocycle having 6 carbon atoms, one of which is nitrogen, the other being carbon atom, X is hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl, May be at any available position on the ring and suitable salts thereof. The compound of claim 18 when R ¹ and R ² are each hydrogen, methyl or ethyl. The compound of claim 19 when one of R ¹ or R ² is methyl or ethyl and the other is hydrogen, methyl or ethyl. The compound of claim 18, wherein one of R ¹ and R ² is methyl or ethyl and the other is hydrogen. The compound of claim 19 when X is hydrogen and R is phenyl, naphthyl, 4-fluorophenyl, 2-halophenyl or 2-lower alkylphenyl. The compound of claim 22 when one of R ¹ or R ² is hydrogen and the remainder is hydrogen, methyl or ethyl. The compound of claim 23 when R is phenyl, 2-fluorophenyl, 2-chlorophenyl, or 2-methylphenyl. The compound of claim 23 when R is phenyl. The compound of claim 23 when R is phenyl, one of R ¹ or R ² is hydrogen, and the remainder is methyl. The compound of claim 23 when R is phenyl, one of R ¹ or R ² is hydrogen and the remainder is ethyl. The compound of claim 18 when R is lower alkyl, cycloalkyl, lower alkenyl, lower haloalkyl or lower haloalkenyl. The compound of claim 28 when R ¹ and R ² are each hydrogen, methyl or ethyl. The compound of claim 29 when R is methyl, ethyl or propyl. The compound of claim 30 when one of R ¹ or R ² is hydrogen, the remainder is methyl or ethyl, and X is hydrogen. The compound of claim 29 when X is hydrogen. The compound of claim 18 when X is hydrogen. The compound of claim 1 where X is hydrogen. The compound of claim 34 when Y is lower alloalkyl having one or two carbon atoms. A herbicidal compound containing a herbicidal amount of a compound according to claim 1 or a mixture of such compounds and a suitable carrier. A herbicidal compound containing an amount of the herbicidal effect of the compound according to claim 25 or a mixture thereof and a suitable carrier. A method of disturbing or destroying a plant comprising applying to the leaves or potential growth medium of the plant an amount of herbicidal effect of the compound according to claim 1 or a mixture thereof. A method of disturbing or destroying a plant, comprising applying to the leaf or potential growth medium of the plant an herbicidal amount of the compound according to claim 25 or a mixture thereof. A compound for controlling plant growth comprising an amount of a compound according to claim 1 or a mixture thereof effective for altering the growth type of a plant. A method of controlling the growth of a plant, comprising applying an amount of a compound according to claim 1 or a mixture thereof to the leaf of the plant or its growth medium effective to change the growth type of the plant. A process for preparing the compound of claim 1 when R is phenyl, naphth-1-yl, inden-1-yl or substituted aryl as defined in claim 1, wherein Contacting the compound, Wherein X and Y are as defined in claim 1, and Z ¹ is a substituted or substituted Raryl as needed with halogen selected from the group consisting of chlorine, bromine and iodine and liquid carboxylic acid under reaction conditions. Corresponding to aryl substituents to produce the compound corresponding to formula (I). The method of claim 47 wherein the method is carried out in an inert organic solvent at a temperature in the range of approximately 0 to 100 ° C. and the halogen is bromine. The method of claim 43 where excess liquid carboxylic acid is used as in the inert organic solvent. A method of making a compound of claim 1 substantially as described herein. A method for preparing a compound of formula I of claim 1 wherein each of R ¹ and R ² is hydrogen, comprising contacting a compound having the formula Wherein X and Y are as defined in claim 1, and have a compound having the formula Wherein R ₅ is lower alkyl, aryl or arylalkyl, R is as defined in claim 1, and is about 0 ° C. using approximately 1-10 degrees of compound (E) per mole of compound (B) It has a strong base under the reaction conditions of the temperature ranges from to 100 ℃. The process of claim 46 wherein said strong base is selected from the group of alkali metal alkanolates, sodium hydrides and potassium hydrides. The method of claim 46 when the process is carried out in an inert organic solvent selected from the group consisting of lower alkanols, tetrahydrofuran, dimethoxyethane, dioxane and suitable mixtures thereof. Claims where R is lower alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, arylalkylene, substituted arylalkylene or alkenylalkyl, and R ¹ and R ² are as defined above herein A process for preparing the compound of formula I of claim 1 comprising contacting a compound having the formula Wherein R ′ ″ is as specified for R herein above, R ¹⁰ is lower alkyl, X and Y are as defined above herein, and are cyclic under reaction conditions of temperature ranging from approximately 0 ° to 200 ° C. Has chemical reagent. The method according to claim 49, wherein the cyclization reagent is a strong acid anhydride, wherein the method is performed using about 1 to 10 moles of cyclization reagent per mole of Compound A '. The method of claim 50 when the method is carried out in an inert organic solvent. The method of claim 51 wherein the cyclization reagent is selected from the group of sulfuric acid, hydrogen chloride, trifluoro-acetic acid and methanesulfonic acid and the inert organic solvent is selected from the group of acetic acid, propionic acid, toluene butyrate and xylene. . A process for preparing a compound of claim 1 in which at least one of R ¹ or R ² is other than hydrogen, comprising contacting the compound having the formula Wherein R ¹ , R, X and Y are as defined above in the present application and have an alkylation reagent having the desired non-hydrogen substitution in an inert organic solvent under reaction conditions at temperatures ranging from approximately 0 ° C. to 100 ° C. The process of claim 53 where the process is a monoalkylation process using from about 1.0 to 1.1 moles of R ² halide having the desired R ² group as the alkylating agent per mole of Compound I. Formula I "in, and R ¹ is hydrogen, said process a compound I" R ² having the desired R ² group as a mole of an alkylating agent of-the claims in the case of double alkylation step of substantially using 1.9 to 4 mol of the halide of claim 53 claim Way. The method of claim 53 wherein said alkylating agent is R ² 'halide, R ² ′ is alkoxyalkyl or alkylthioalkyl, and about 3 to 6 moles of said R ² ′ halide is used per mole of compound II ′. The method of claim 53 when the inert organic solvent is selected from the group of halogenated alkane and tetrahydrofuran. A process for preparing the compound of claim ^{1 in} which R ¹ is lower alkyl and R ² is hydrogen or lower alkyl, wherein R ¹ is hydrogen and R ² is hydrogen or lower alkyl Contacting a compound corresponding to the lower dialkylsulfate required in the presence of a strong base under reaction conditions at a temperature ranging from approximately 0 ° C. to 100 ° C. using approximately 1 to 4 moles of the said dialkyl sulfate per mole of formula I as the starting material. How to. The method of claim 58 when the method is carried out in an inert organic solvent in the presence of a phase shift reagent. The method of claim 59 wherein the strong base is selected from the group of sodium hydroxide, potassium hydroxide, sodium ethoxide, sodium carbonate and potassium carbonate. The method of claim 60 when the inert organic solvent is selected from the group of methylene chloride and carbon tetrachloride. A process for preparing a suitable salt of a compound of formula I of claim 1, comprising contacting with a strong base having a base cation which requires a compound corresponding to formula I when one of R ¹ and R ² are both hydrogen Method comprising the same. 63. The method of claim 62 wherein said base is selected from the group of n-buryl lithium, sodium hydride and potassium hydride. ※ Note: The disclosure is based on the initial application.