Claims
- 1. A compound of the formula ##STR83## wherein X is (--CR.sub.4 R.sub.4).sub.m in which m is 0 or 1;
- Y is (--CR.sub.5 R.sub.6).sub.n is which n is 0, 1 or 2;
- Z is (--CR.sub.7 R.sub.7).sub.p in which p is 1, 2 or 3;
- the sum of m+n+p is an integer of 2 to 5, inclusive;
- R.sub.1 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms;
- R.sub.2 is a hydrogen atom or a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sub.3 is a hydrogen atom or an alkyl group containing from 1 to 10 carbon atoms; a cyano group; an alkyl group substituted by: a hydroxy group, a cyano group, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a C.sub.6-10 arylsulfonyl group, a C.sub.7-11 aralkylsulfonyl group, an azido group, a C.sub.1-6 alkoxycarbonyl group, a hydroxycarbonyl group, a dialkoxyphosphonge group or an amine oxide, carbamoyl or thiocarbamoyl group, each nitrogen atom substitued by hydrogen or by 1 or 2 alkyl groups containing from 1 to 4 carbon atoms; or R.sub.3 is an alkenyl or alkynyl group containing 2 to 4 carbon atoms; 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 halogen or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms, each optionally substituted by one or more halogen atoms, or R.sub.3 is a group --CO.sub.2 R.sub.8 ; --CON(R.sub.8).sub.2, or --CSNH.sub.2 in which R.sub.8 is a hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms; or R.sub.3 is an acyl group containing 1 to 6 carbon atoms or an oxime or an acetal derivative of said acyl group;
- each R.sub.4 is independently a hydrogen atom, an alkyl group containing from 1 to 4 carbon atoms each optionally substituted by up to 3 halogen atoms, a hydroxy group or an alkoxy group containing 1 to 4 carbon atoms; or one of R.sub.4 and R.sub.1 when taken together form a carbon-carbon bond;
- R.sub.5 and R.sub.6 each independently is a hydrogen atom, or an alkyl group containing from 1 to 2 carbon atoms; or when located on a carbon atom adjacent to the ring oxygen atom then R.sub.5 and R.sub.6 together form an alkylene group containing 4 or 5 carbon atoms;
- each R.sub.7 independently is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms; or when n is 0 then R.sub.7 is also a chlorine atom, a bromine atom, or two of R.sub.7 when located on adjacent carbon atoms together form an epoxide ring or carbon-carbon bond; or when n is 1 then one R.sub.7 on the carbon adjacent to the carbon bearing R.sub.2 is a hydroxy group, a C.sub.7-11 aralkoxy group or an alkoxy group containing 1 to 4 carbon atoms, and the other R.sub.7 is a hydrogen atom;
- both of Q are hydrogen atoms or are fluorine atoms;
- W is an alkenyl or alkynyl group containing up to 4 carbon atoms, or an aromatic or a heterocyclic group containing up to 14 carbon atoms, each optionally substituted by hydroxy, cyano, halogen of atomic number of from 9 to 35, inclusive, alkyl, haloalyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl alkylsulfonyl, alkenyl or alkynyl of up to 4 carbon atoms, or aminocarbonyl, carboxyl, amino or alkanoylamino, each of which hydrogen can be substituted by alkyl of 1 to 4 carbon atoms; a cycloalkyl group containing 3 to 10 carbon atoms optionally substituted by alkyl of 1 to 3 carbon atoms; a cyclohexenyl group; a cyano group; or a secondary alkyl group containing 3 to 10 carbon atoms; and stereoisomer forms or mixtures thereof.
- 2. A compound according to claim 1 wherein R.sub.1 is a hydrogen atom, each Q is a hydrogen atom, and W is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms, a 2-pyridinyl group; a 3-pyridazinyl group; a pyrazinyl group; a pyrimidinyl group; a 2-furanyl group; or a phenyl group optionally substituted by one or more of halogen, cyano, amino, or an alkoxy, alkylthio group containing 1 to 3 carbon atoms, each optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, or by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms.
- 3. A compound according to claim 1 wherein R.sub.2 is a hydrogen atom or a straight-chain alkyl group containing from 1 to 3 carbon, atoms.
- 4. A compound according to claim 3 wherein R.sub.3 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms.
- 5. A compound according to claim 3 wherein R.sub.2 is a methyl group, and R.sub.3 is an isopropyl group when n is 0, or is a hydrogen atom when n is 1 or 2.
- 6. A compound according to claim 3 wherein each R.sub.4 and R.sub.7 is a hydrogen atom.
- 7. A compound according to claim 3 wherein R.sub.5 and R.sub.6 each is a methyl group when on a ring carbon atom adjacent to the ring oxygen atom or otherwise each is a hydrogen atom.
- 8. A compound according to claim 1 wherein W is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by 1 or 2 chlorine or fluorine atoms or methyl groups.
- 9. A compound according to claim 8 wherein W is a 2-methylphenyl, a 2-chlorophenyl, a 2-fluorophenyl, a 2,6-dichlorophenyl or 2-pyridinyl group.
- 10. A compound according to claim 9 wherein each R.sub.1, R.sub.4 and R.sub.7 is a hydrogen atom, R.sub.2 is a methyl group, R.sub.3 is an isopropyl group when n is 0 and is a hydrogen atom when n is 1 or 2, each R.sub.5 and R.sub.6 is a methyl group when on a ring carbon atom adjacent to the ring oxygen atom or otherwise each R.sub.5 and R.sub.6 is a hydrogen atom.
- 11. A compound according to claim 10 wherein W is a 2-methylphenyl group.
- 12. A compound according to claim 10 wherein W is a 2-chlorophenyl group.
- 13. A compound according to claim 10 wherein W is a 2-fluorophenyl group.
- 14. A compound according to claim 10 wherein W is a 2,6-dichlorophenyl group.
- 15. A compound according to claim 10 wherein W is a 2-pyridinyl group.
- 16. A compound according to any one of claims 1, 8 or 10 in which m is 1, n is 0 or 1 and p is 2.
- 17. A compound of the formula I ##STR84## wherein R is a hydrogen atom; or a straight-chain alkyl group containing from 1 to 6 carbon atoms;
- R.sub.1 is a hydrogen atom; a cyano group; or is an alkyl group containing from 1 to 10 carbon atoms optionally substituted by up to 3 halogen atoms, each having an atomic number of from 9 to 35, inclusive, or by a hydroxy group, a cyano group, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a C.sub.6-10 arylsulfonyl group, a C.sub.7-11 aralkylsulfonyl group, an azido group, a C.sub.1-6 alkoxycarbonyl group, a hydroxycarbonyl group, a dialkoxyphosphonyl group an amine oxide group, a carbamoyl group, a thiocarbamoyl group substituted by hydrogen or by 1 or 2 alkyl groups containing from 1 to 6 carbon atoms; or
- R.sub.1 is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms; or is an aryl or aralkyl group, each containing from 6 to 11 carbon atoms, and 1 to 4 carbons in the alkyl portion, each optionally ring-substituted by one or more substituents independently selected from a halogen atom, each having an atomic number of from 9 to 35, inclusive, or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or R.sub.1 is a group --CO.sub.2 R.sub.6, --CON(R.sup.6).sub.2, or --CSNH.sub.2 in which R.sub.6 is a hydrogen atom, or an alkyl group containing from 1 to 6 carbon atoms;
- R.sub.2 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-furanyl group; a naphthyl group or a phenyl group optionally substituted by one or more substituents independently selected from a halogen atom, each having an atomic number of from 9 to 35, inclusive, or an alkoxy, alkylthio or alkylsulfinyl group containing from 1 to 3 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or naphthyl or phenyl substituted by an alkyl group containing 1 or 2 carbon atoms optionally substitued by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, monoor dialkylamino- or alkanoylamino containing 1 or 2 carbon atoms in each alkyl group, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms, or is a phenyl group substitued by mono- or dialkylamino- or alkanoylamino containing 1 or 2 carbon atoms in each alkyl group or by carboxyl;
- each R.sub.3 is independently selected from a hydrogen atom; a chlorine atom; a bromine atom; or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms, each having an atomic number of from 9 to 35, inclusive; or two of R.sup.3 when located on adjacent carbon atoms together form an epoxide ring or carbon-carbon bond;
- R.sub.4 is a hydrogen atom; or an alkyl group containing from 1 to 4 carbon atoms optionally substituted by up to 3 halogen atoms having an atomic number of from 9 to 35, inclusive;
- each R.sup.5 is independently selected from a hydrogen atom; or an alkyl group containing from 1 to 4 carbon atoms, each optionally substituted by up to 3 halogen atoms having an atomic number of from 9 to 35, inclusive, a hydroxy group, or an alkoxy group containing 1 to 4 carbon atoms; or
- R.sup.4 and R.sup.5 when taken together form a carbon-carbon bond;
- both of Q are hydrogen atoms or fluorine atoms; and stereoisomeric forms or mixtures thereof.
- 18. A compound according to claim 17 wherein each Q is a hydrogen atom; R is a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms, and R.sup.1 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, optionally substituted by halogen.
- 19. A compound according to claim 17 wherein each R.sup.3 is a hydrogen atom or an alkyl group containing 1 or 2 carbon atoms.
- 20. A compound according to claim 17 wherein R.sup.4 is a hydrogen atom.
- 21. A compound according to claim 17 wherein each R.sup.5 is a hydrogen atom or an alkyl group containing 1 or 2 carbon atoms.
- 22. A compound according to claim 17 wherein each R.sup.3, R.sup.4 and R.sup.5 is a hydrogen atom.
- 23. A compound according to claims 17 or 22 wherein R.sup.2 is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by 1 or 2 chlorine or fluorine atoms or methyl groups.
- 24. A compound of the formula Ia ##STR85## wherein R is a straight-chain alkyl group containing from 1 to 6 carbon atoms; R.sup.1 is an alkyl group containing from 1 to 6 carbon atoms optionally substituted by up to 3 halogen atoms selected independently from fluorine, chlorine and bromine atoms or by OH, CN, an alkoxy group containing from 1 to 6 carbon atoms, a C.sub.1-6 alkylsulfonyl group, a phenylsulfonyl group, a benzylsulfonyl group, or is an aryl or aralkyl group each containing from 6 to 11 carbon atoms, and 1 or 2 carbon atoms in any alkyl portion, optionally substituted by one or more substituents independently selected from halogen atoms having an atomic number of from 9 to 35, inclusive, or by an alkyl or alkoxy group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of from 9 to 17; and R.sup.2 is an ethynyl group, a 2-pyridinyl group, a 2-furanyl group or a phenyl group optionally substituents by one or more substituents independently selected from a halogen atom having an atomic number of from 9 to 35, inclusive, or by an alkoxy or alkylthio group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, or phenyl substituted by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms; and stereoisomeric forms or mixtures thereof.
- 25. A compound according to claim 24 wherein R.sup.2 is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by one or more chlorine atoms, fluorine atoms or methyl groups.
- 26. A compound according to claim 25 wherein R is an alkyl group containing from 1 to 3 carbon atoms and R.sup.1 is an alkyl group containing from 1 to 3 carbon atoms optionally substituted by halogen.
- 27. A compound according to claim 26 wherein R is an alkyl group containing from 1 to 2 carbon atoms, and R.sup.1 is an alkyl group containing from 1 to 3 carbon atoms optionally substituted by chlorine.
- 28. A compound according to claim 27 wherein R is a methyl or ethyl group and R.sup.1 is a methyl, ethyl, n-propyl, isopropyl or 1-chloromethylethyl group.
- 29. A compound according to claim 28 wherein R.sup.2 is 2-pyridinyl or a phenyl group substituted in the 2- or 2- and 6-positions by a chlorine atom, a fluorine atom or a methyl group.
- 30. A compound according to claim 29 wherein R is a methyl group and R.sup.1 is an isopropyl group.
- 31. A compound according to claim 30 wherein R.sup.2 is a 2-methylphenyl group.
- 32. A compound according to claim 30 wherein R.sup.2 is a 2-chlorophenyl group.
- 33. A compound according to claim 30 wherein R.sup.2 is a 2-fluorophenyl group.
- 34. A compound according to claim 30 wherein R.sup.2 is a 2,6-dichlorophenyl group.
- 35. A compound according to claim 30 wherein R.sup.2 is a 2-pyridinyl group.
- 36. A compound according to claim 29 wherein R and R.sup.1 each is an ethyl group or R is a methyl group and R.sup.1 is a 1-chloro-1-methylethyl group.
- 37. A compound according to claim 36 wherein R.sup.2 is a 2-methylphenyl, a 2-chlorophenyl, a 2-fluorophenyl, a 2,6-dichlorophenyl or a 2-pyridinyl group.
- 38. A compound according to according claim 17 or 24 in which the OCQ.sub.2 R.sup.2 or OCH.sub.2 R.sup.2 group is in the exo configuration with respect to the oxygen bridge, substantially free of other stereoisomer configurations.
- 39. A compound according to claim 30 in which the OCH.sub.2 R.sup.2 group is in the exo configuration with respect to the oxygen bridge and the carbon bearing the R group has the S absolute configuration, substantially free of other stereoisomer configurations.
- 40. A compound of the formula II ##STR86## wherein both of Q are hydrogen atoms or fluorine atoms; R is a hydrogen atom; or a straight-chain alkyl group containing from 1 to 6 carbon atoms; R.sup.1 and R.sup.2 each independently is a hydrogen atom; or an alkyl group containing 1 or 2 carbon atoms; or R.sup.1 and R.sup.2 taken together form an alkylene group containing 4 or 5 carbon atoms; R.sup.3 is a hydrogen atom; a hydroxy group; a benzyloxy group; or an alkoxy group containing 1 or 2 carbon atoms; R.sup.4 is an alkenyl or alkynyl group containing from 2 to 4 carbon atoms; a 2-pyridinyl group; a 2-furanyl group; or a phenyl group optionally substituted by one or more substituents independently selected from a cyano group, a halogen atom, each having an atomic number of from 9 to 35, inclusive; or an alkoxy or alkylthio group containing from 1 to 3 carbon atoms, each optionally substituted by one or more halogen atoms, each having an atomic number of 9 or 17, or by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms; R.sup.5, R.sup.6, R.sup.7 and each R.sup.8 is each independently is a hydrogen atom; or an alkyl group containing from 1 to 4 carbon atoms.
- 41. A compound according to claim 40 wherein R is a hydrogen atom or an alkyl group containing 1 or 2 carbon atoms.
- 42. A compound according to claim 40 wherein R.sup.1 and R.sup.2 each independently is a hydrogen atom, an alkyl group containing 1 or 2 carbon atoms or R.sup.1 and R.sup.2 when taken together is a tetramethylene or pentamethylene group.
- 43. A compound according to claim 40 wherein both of Q and R.sup.3, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are hydrogen atoms.
- 44. A compound according to claim 40 wherein R.sup.4 is an ethynyl group, a 2-pyridinyl group, a phenyl group or a phenyl group substituted at the 2- or 2- and 6-position by a chlorine atom, a fluorine atom or a methyl group.
- 45. A compound according to claim 40 wherein R is a methyl group, R.sup.1 and R.sup.2 each is a methyl or ethyl group, R.sup.3 is a hydrogen atom and R.sup.4 is a phenyl group substituted at the 2- or 2- and 6-position by a chlorine atom, a fluorine atom or a methyl group.
- 46. A compound of the formula IIc ##STR87## wherein R is a straight-chain alkyl group containing from 1 to 6 carbon atoms; R.sup.1 and R.sup.2 each independently is an alkyl group containing from 1 to 2 carbon atoms or R.sup.1 and R.sup.2 when taken together form a alkylene group containing 4 or 5 carbon atoms; R.sup.3 is a hydrogen atom, a hydroxy group, a benzyloxy or an alkoxy group containing 1 or 2 carbon atoms; and R.sup.4 is an ethynyl group, a 2-pyridinyl group, a 2-furanyl group or a phenyl group optionally substituted by one or more substituents independently selected from a halogen atom having an atomic number of from 9 to 35, inclusive, or an alkoxy or alkylthio group containing from 1 to 2 carbon atoms each optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, or by an alkyl group containing 1 or 2 carbon atoms optionally substituted by one or more halogen atoms having an atomic number of 9 or 17, hydroxy, alkoxy of 1 or 2 carbon atoms or alkylthio of 1 or 2 carbon atoms.
- 47. A compound according to claim 46 wherein R.sup.4 is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by one or more chlorine atoms, fluorine atoms or methyl groups.
- 48. A compound according to claim 46 wherein R is a methyl group; R.sup.1 and R.sup.2 each independently is a methyl group or an ethyl group or R.sup.1 and R.sup.2 when taken together is a tetramethylene or a pentamethylene group; and R.sup.3 is a hydrogen atom.
- 49. A compound according to claim 48 wherein R.sup.1 and R.sup.2 are both methyl or ethyl groups.
- 50. A compound according to claim 48 wherein R.sup.4 is 2-pyridinyl or a phenyl group substituted in the 2- or 2- and 6-position by a chlorine atom, a fluorine atom or a methyl group.
- 51. A compound according to claim 50 wherein R.sup.1 and R.sup.2 are both methyl groups.
- 52. A compound according to claim 51 wherein R.sup.4 is a 2-methyl-phenyl group.
- 53. A compound according to claim 50 wherein R.sup.1 and R.sup.2 are both ethyl groups.
- 54. A compound according to claim 53 wherein R.sup.4 is a 2-methyl-phenyl group.
- 55. A compound according to claim 53 wherein R.sup.4 is a 2-fluorophenyl group.
- 56. A compound according to claim 48 in which the OCH.sub.2 R.sup.4 group is in the endo configuration with respect to the unsubstituted ethano bridge, substantially free of other stereoisomer configurations.
- 57. A compound according to claim 56 in which the carbon bearing the R group is in the S configuration, substantially free of other stereoisomer configurations.
- 58. A compound according to claim 1 wherein m, n and p each is 1.
- 59. A compound according to claim 58 wherein each of Q, R.sub.1, R.sub.3, R.sub.4 and R.sub.7 is a hydrogen atom, R.sub.2 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, R.sub.6 and R.sub.7 each is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, and W is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by 1 or 2 chlorine or fluorine atoms or methyl groups.
- 60. A compound according to claim 59 wherein R.sub.2, R.sub.6 and R.sub.7 each is a methyl group and W is 2-methylphenyl, 2-fluorophenyl or a phenyl group.
- 61. A compound according to claim 1 wherein m is 1, n is 0 and p is 3.
- 62. A compound according to claim 61 wherein each Q, R.sub.1, R.sub.4 and R.sub.7 is a hydrogen atom, R.sub.2 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, R.sub.3 is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, and W is an ethynyl group, a 2-pyridinyl group or a phenyl group optionally substituted by 1 or 2 chlorine or fluorine atoms or methyl groups.
- 63. A compound according to claim 62 wherein R.sub.2 and R.sub.3 are methyl groups and W is a 2-methylphenyl or 2-fluorophenyl group.
- 64. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1, 17, 24, 40, 46, 58 or 61 and at least one carrier or surface-active agent.
- 65. A method of controlling undesirable plant growth at a locus comprises applying to the locus or the plants an effective amount of a compound according to any one of claims 1, 17, 24, 40, 46, 58 or 61.
- 66. A method according to claim 65 wherein the control is herbicidal.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of application Ser. No. 331,094, filed Dec. 16, 1981 now abandoned.
US Referenced Citations (12)
Foreign Referenced Citations (1)
Number |
Date |
Country |
2937645 |
Apr 1981 |
DEX |
Non-Patent Literature Citations (3)
Entry |
Orchin et al., The Vocabulary of Org. Chem., Wiley, p. 80. |
Fletcher et al., Nomenclature of Org. Compounds, p. 39, p. 40. |
Rose, The Condensed Chem. Dictionary, 7th. Ed., Reinhold, p. 991 (1966). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
331094 |
Dec 1981 |
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