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EP0081893A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Oxabicycloalkane herbicides

Assignee: Shell Internationale Research Maatschappij BV
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Filing: 1982-12-15
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Granted: —
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Expires: 2002-12-15
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Abstract

Abstract Herbicidal compounds of the general formula wherein X is (-CR 4 R 4 -) m in which m is 0 or 1; Y is (-CR 5 R 6 -) n in which n is 0,1 or 2; Z is (-CR 7 R 7 -) p in which p is 1, 2 or 3; the sum of m + n + p is an integer of from 2 to 5; R, is a hydrogen atom or a C 1-6 alkyl group optionally substituted by up to 3 fluorine, chlorine and/or bromine atoms; R 2 is a hydrogen atom or a C 1-6 straight-chain alkyl group; R 3 is a hydrogen atom; a C 1-10 alkyl group; a cyano group; an alkyl group substituted by one or more halogen atoms or by a hydroxy group, a cyano group, a C 1-6 alkoxy group, an aryloxy group, a C 1-6 alkylsulphonyl group, an arylsulphonyl group, an aralkylsulphonyl group, an azido group, a C 1-6 alkoxycarbonyl group, an aralkoxycarbonyl group, a hydroxycarbonyl group, a phosphoryl group, a phosphoryloxy group, or an amine oxide, carbamoyl or thiocarbamoyl group in which each nitrogen is substituted by hydrogen or by 1 or 2 C 1-4 alkyl groups; a C 2 - 4 alkenyl or alkynyl group; an aryl or aralkyl group, each containing from 6 to 11 carbon atoms including 1 to 4 carbon atoms in the alkyl portion and optionally ring substituted by one or more fluorine, chlorine and/or bromine atoms or by a C 1-2 alkyl or alkoxy group, each optionally substituted by one or more fluorine and/or chlorine atoms; a group -CSNH 2 : a group -CO 2 R 8 or -CON(R 8 ) 2 in which R 8 is a hydrogen atom or a C 1-6 alkyl group; or a C 1-6 acyl group or an oxime or an acetal derivative of said acyl group; each R 4 is independently a hydrogen atom; an alkyl group optionally substituted by up to 3 halogen atoms; a hydroxy group; or a C 1-4 alkoxy group; or one of R 4 and R 1 together form a carbon-carbon bond; R 5 and R 6 each independently is a hydrogen atom or a C 1-2 alkyl group; or when located on a carbon atom adjacent to the ring oxygen atom then R 5 and R 6 together form an alkylene group containing 4 or 5 carbon atoms; each R 7 independently is a hydrogen atom or a C 1-4 alkyl group optionally substituted by up to 3 halogen atoms; or when n is 0 then R 7 is also a chlorine or bromine atom, or two of R 7 when located on adjacent carbon atoms togetherform an epoxide ring or a carbon-carbon bond; or when n is 1, then one R 7 on the carbon adjacent to the carbon bearing R 2 is a hydroxy group, a C 7-11 aralkoxy group, or a C 1-4 alkoxy group, and the other R 7 is a hydrogen atom; both of Q are hydrogen atoms or fluorine atoms; and W is an optionally-substituted unsaturated group of up to 4 carbon atoms; an optionally substituted aryl or heterocyclic group containing up to 14 carbon atoms; a C 3-10 cycloaliphatic group optionally substituted by C 1-3 alkyl; or C 3-10 secondary alkyl group.

Inventors

  • 👤 George Bernson Payne
  • 👤 Samuel Barney Soloway
  • 👤 James Edward Powell
  • 👤 Steven Alan Roman
  • 👤 Willy Dietrich Kollmeyer

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-31 21:07
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A01; A01N; A01N43/00; A01N43/90; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/103; C07C29/106; C07C29/36; C07C29/38; C07C29/40; C07C33/00; C07C33/05; C07C33/12; C07C33/14; C07C35/00; C07C35/02; C07C35/08; C07C35/22; C07C35/37; C07C35/38; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1781; C07C45/00; C07C45/51; C07C45/511; C07C45/513; C07C2601/00; C07C2601/06; C07C2601/08; C07C2601/12; C07C2601/16; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/20

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 553 words
A compound of the general formula I wherein X is (-CR 4 R 4- ) m in which m is 0 or 1; Y is (-CR 5 R 6 -) n in which n is 0, 1 or 2; Z is (-CR 7 R 7 -) p in which p is 1, 2 or 3; the sum of m + n + p is an integer of from 2 to 5; R 1 is a hydrogen atom or C 1-6 alkyl group optionally substituted by up to 3 fluorine, chlorine and/or bromine atoms; R 2 is a hydrogen atom or a C 1-6 straight-chain alkyl group; R 3 is a hydrogen atom; a C 1-10 alkyl group; a cyano group; an alkyl group substituted by one or more halogen atoms or by a hydroxy group, a cyano group, a C 1-6 alkoxy group, an aryloxy group, a C 1-6 alkylsulphonyl group, an arylsulphonyl group, an aralkylsulphonyl group, an azido group, a C 1-6 alkoxycarbonyl group, an aralkoxy carbonyl group, a hydroxycarbonyl group, a phosphoryl group, a phosphoryloxy group, or an amine oxide, carbamoyl or thiocarbamoyl group in which each nitrogen is substituted by hydrogen or by 1 or 2 C 1-4 alkyl groups; a C 2-4 alkenyl or alkynyl group; an aryl or aralkyl group, each containing from 6 to 11 carbon atoms including 1 to 4 carbon atoms in the alkyl portion and optionally ring substituted by one or more fluorine, chlorine and/or bromine atoms or by a C 1-2 alkyl or alkoxy group, each optionally substituted by one or more fluorine and/or chlorine atoms; a group -CSNH 2 ; a group -CO 2 R 8 or -CON(R 8 ) 2 in which R 8 is a hydrogen atom or a C 1-6 alkyl group; or a C 1-6 acyl group or an oxime or an acetal derivative of said acyl group; each R 4 is independently a hydrogen atom; an alkyl group optionally substituted by up to 3 halogen atoms; a hydroxy group; or a C 1-4 alkoxy group; or one of R 4 and R 1 together form a carbon-carbon bond; R 5 and R 6 each independently is a hydrogen atom or a C 1-2 alkyl group; or when located on a carbon atom adjacent to the ring oxygen atom then R 5 and R 6 together form an alkylene group containing 4 or 5 carbon atoms; each R 7 independently is a hydrogen atom or a C 1-4 alkyl group optionally substituted by up to 3 halogen atoms; or when n is 0 then R 7 is also a chlorine or bromine atom, or two of R 7 when located on adjacent carbon atoms together form an epoxide ring or a carbon-carbon bond; or when n is 1, then one R 7 on the carbon adjacent to the carbon bearing R 2 is a hydroxy group, a C 7-11 aralkoxy group, or a C 1-4 alkoxy group, and the other R 7 is a hydrogen atom; both of Q are hydrogen atoms or fluorine atoms; and W is an optionally-substituted unsaturated group of up to 4 carbon atoms; an optionally substituted aryl or heterocyclic group containing up to 14 carbon atoms; a C 3-10 cycloaliphatic group optionally substituted by C1-3 alkyl; or a C 3-10 secondary alkyl group.
Claim 2
Dependent Claim 23 words
A compound as claimed in Claim 1, in which each R 4 independently represents a hydrogen atom or a methyl or ethyl group.
Claim 3
Dependent Claim 31 words
A compound as claimed in either claim 1 or claim 2, in which each of R 5 and R 6 independently represents a hydrogen atom or a methyl or ethyl group.
Claim 4
Dependent Claim 75 words
A compound as claimed in any one of claims I to 3, in which each R 7 independently represents a hydrogen atom or a methyl or ethyl group, or when n is 0, a chlorine or bromine atom, or when n is 1, one R 7 on the carbon atom adjacent to the carbon atom bearing R 2 is a hydroxy, methoxy, ethoxy or benzyloxy group, the or each other R being a hydrogen atom.
Claim 5
Dependent Claim 16 words
A compound as claimed in claim 4, in which each R 7 represents a hydrogen atom.
Claim 6
Dependent Claim 24 words
A compound as claimed in any one of claims 1 to 5, in which m is 1; n is 0; and p is 2.
Claim 7
Dependent Claim 24 words
A compound as claimed in any one of claims 1 to 5, in which m is 1; n is 1; and p is 2.
Claim 8
Dependent Claim 78 words
A compound as claimed in any one of claims I to 7, in which W represents a cyano group; a C 2-4 alkenyl or alkynyl group; a pyrimidinyl, pyrazinyl, pyridazinyl, pyridyl, furyl or naphthyl group; or a phenyl group optionally substituted by one or more of hydroxy; cyano; halogen; C 1-3 alkoxy, alkylthio or alkylsulphinyl, each optionally substituted by halogen; benzyloxy; C 1-3 alkyl optionally substituted by halogen, hydroxy, amino, alkanoylamino, alkoxy or alkylthio; and carboxyl or aminocarboxyl.
Claim 9
Dependent Claim 80 words
A compound as claimed in claim 8, in which W represents a C 2-4 alkenyl or alkynyl group; a 4-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 2-pyridyl or 2-furyl group; or a phenyl group optionally substituted by one or more of halogen, cyano, amino, C 1-3 alkoxy or alkylthio each optionally substituted by one or more fluorine and/or chlorine atoms, or C 1-2 alkyl optionally substituted by one or more fluorine and/or chlorine atoms or by hydroxy, C 1-2 alkoxy or C 1-2 alkylthio.
Claim 10
Dependent Claim 40 words
A compound as claimed in claim 9, in which W represents an ethynyl group; a 2-pyridyl group; or a phenyl group which is unsubstituted or substituted by one or two substituents selected from methyl groups, fluorine atoms and chlorine atoms.
Claim 11
Dependent Claim 24 words
A compound as claimed in any one of claims 1 to 10, in which R 7 represents a methyl group or a hydrogen atom.
Claim 12
Dependent Claim 22 words
A compound as claimed in any one of claims 1 to 11, in which R 2 represents a methyl or ethyl group
Claim 13
Dependent Claim 114 words
A compound as claimed in any one of claims 1 to 12, in which R 3 represents a hydrogen atom; a C 1-6 alkyl group optionally substituted by up to 3 fluorine, chlorine and/or bromine atoms or by a hydroxy, cyano, C 1-6 al ko x y, C 1-6 alkylsulphonyl, phenylsulphonyl or benzylsulphonyl group; a C 2-4 alkenyl or alkynyl group; or an aryl or aralkyl group containing 6 to 11 carbon atoms and 1 or 2 carbon atoms in any alkyl portion, optionally ring substituted by one or more fluorine, chlorine and/or bromine atoms or by a C 1-2 alkyl or alkoxy group optionally substituted by one or more fluorine and/or chlorine atoms.
Claim 14
Dependent Claim 29 words
A compound as claimed in claim 13, in which R 3 represents a hydrogen atom or a C 1-3 alkyl group optionally substituted by one or more halogen atoms.
Claim 15
Dependent Claim 20 words
15 A compound as claimed in any one of claims 1 to 14, in which both Q's represent hydrogen atoms.
Claim 16
Dependent Claim 18 words
A compound as claimed in claim 1 and named in any one of Examples 26 to 193 herein.
Claim 17
Dependent Claim 310 words
A compound as claimed in claim 1, in which R 3 is a hydrogen atom or a C 1-10 alkyl group or when n is 0, then R 3 is additionally a cyano group, an alkyl group substituted by a hydroxy group, a cyano group, a C 1-6 alkylsulphonyl group, an arylsulphonyl group, an aralkylsulphonyl group, an azido group, a C 1-6 alkoxycarbonyl group, a hydroxycarbonyl group, a phosphoryl group, a phosphoryloxy group, or an amine oxide, carbamoyl or thiocarbamoyl group in which each nitrogen is substituted by hydrogen or by 1 or 2 C 1-4 alkyl groups; or R 3 is a C 2-4 alkenyl or alkynyl group; an aryl or aralkyl group, each containing from 6 to 11 carbon atoms including 1 to 4 carbon atoms in the alkyl portion and optionally ring substituted by one or more substituents selected from fluorine, chlorine and/or bromine atoms, or by a C1-2 alkyl or alkoxy group, each optionally substituted by one or more fluorine and/chlorine atoms; or R 3 is a group -CO 2 R 8 or -CON(R 8 ) 2 in which R 8 is a hydrogen atom or a C 1-6 alkyl group; each R 4 is independently a hydrogen atom or an alkyl group optionally substituted by up to 3 halogen atoms; or one of R 4 and R 1 together form a carbon-carbon bond; and W is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms; a 4-pyrimidinyl group; a 2-pyrazinyl group; a 3-pyridazinyl group; a 2-pyridinyl group; a 2-furyl group; or a phenyl group optionally substituted by one or more of halogen, cyano, amino, C 1-3 alkoxy or alkylthio each optionally substituted by one or more fluorine and/or chlorine atoms, or C 1-2 alkyl optionally substituted by one or more fluorine and/or chlorine atoms, hydroxy, C 1-2 alkoxy, or C 1-2 alkylthio.
Claim 18
Dependent Claim 99 words
A process for the preparation of a compound as claimed in claim 1, which comprises reacting a compound of the general - formula in which R 1 , R 29 R 3 , X, Y and Z have the meanings given for the general formula I, with a compound of the general formula WCQ 2 L, in which W and Q have the meanings given for the general formula I, and L represents a suitable leaving group; and if required, converting a resulting compound of the general formula I into any other required compound of the general formula I.
Claim 19
Dependent Claim 16 words
A process as claimed in claim 18, carried out in the presence of a strong base.
Claim 20
Dependent Claim 24 words
A process as claimed in either claim 18 or claim 19, carried out at a temperature in the range of from 0 to 120°C.
Claim 21
Dependent Claim 21 words
A process as claimed in claim 18, carried out substantially as described in any one of Examples 26 to 32 herein.
Claim 22
Dependent Claim 22 words
A compound as claimed in claim 1, whenever prepared by a process as claimed in any one of claims 18 to 21.
Claim 23
Dependent Claim 28 words
A herbicidal composition which comprises a compound as claimed in any one of claims 1 to 17 and 22, together with a carrier * and/or a surface-active agent.
Claim 24
Dependent Claim 38 words
A process for the control of unwanted plants at a locus, which comprises treating the locus with a compound as claimed in anyone of claims 1 to 17 and 22 or a composition as claimed in claim 23.

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