Herbicidal cyclohexanol derivatives, compositions, and method of use therefor

• US 4,761,172 A
• Filed: 10/05/1984
• Issued: 08/02/1988
• Est. Priority Date: 10/05/1983
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Keil, Michael, Becker, Rainer, Meyer, Norbert, Jahn, Dieter, Wuerzer, Bruno, Richarz, Winfried, Schirmer, Ulrich
• Primary Examiner(s): Rotman, Alan L.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US06/658,432
• Time in Patent Office: 1,397 Days
• Field of Search: 549/13, 549/419, 549/420, 549/425, 71/88, 71/90, 71/91, 71/115
• US Class Current: 504/292
• CPC Class Codes: A01N 35/10 containing a carbon-to-nitrogen double bond
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• CPC Class Codes: A01N 37/38 having at least one oxygen or sulfur atom attached to an aromatic ring system
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 41/04 Sulfonic acids; Derivatives thereof
• CPC Class Codes: A01N 43/08 with oxygen as the ring hetero atom
• CPC Class Codes: A01N 43/16 with oxygen as the ring hetero atom
• CPC Class Codes: A01N 43/18 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: A01N 57/12 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 261/18 Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
• CPC Class Codes: C07D 307/14 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 309/06 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 309/10 Oxygen atoms
• CPC Class Codes: C07D 335/02 not condensed with other rings
• CPC Class Codes: C07D 405/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 407/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 493/04 : Ortho-condensed systems
• CPC Class Codes: C07F 7/1804 : Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 9/177 : with cycloaliphatic alcohols
• CPC Class Codes: C07F 9/58 : Pyridine rings
• CPC Class Codes: C07F 9/65515 : the oxygen atom being part of a five-membered ring

Abstract

Cyclohexenol derivatives of the formula ##STR1## where R¹, R², R³, X and A have the meanings stated in the description, are used for controlling undesirable plant growth.

Claims

1. A cyclohexenol derivative of the formula I ##STR19## wherein R₁ is a tetrahydropyran, a tetrahydrothiopyran, a 1-oxo-tetrahydrothiopyran, or a 1,1-dioxo-tetrahydrothiopyran radical, X is hydrogen wherein R¹ is a pyran or thiopyran radical, is hydrogen or methoxycarbonyl, R² is alkyl of 1 to 4 carbon atoms, R³ is alkyl of 1 to 3 carbon atoms, alkenyl of 3 or 4 carbon atoms, haloalkenyl of 3 or 4 carbon atoms and 1 to 3 halogen substituents, or propargyl, and A is a radical of the general structure DE, where D is methylene, CO or SO₂ and E is an alkyl or alkenyl radical of not more than 20 carbon atoms, unsubstituted or methyl-substituted cycloalkyl of not more than 6 carbon atoms, or styryl, or is a phenyl or benzyl radical which is unsubstituted or substituted by not more than 3 substituents from the group consisting of halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and nitro, or is a 1-methylbenzyl or 1,1-dimethylbenzyl radical which is unsubstituted or substituted by halogen or methoxy, or is haloalkyl of note more than 3 carbon atoms and not more than 3 halogen atoms, alkoxymethyl, acetoxymethyl or alkoxycarbonylalkyl, or is phenoxyalkyl which is unsubstituted or substituted in the phenoxy moiety by not more than 3 substituents from the group consisting of halogen, alkyl, alkoxy and methylsulfonyl, and which possesses a straight-chain or branched alkylene chain of not more than 5 carbon atoms, or

A is a radical of the formula ##STR20## where R⁴ is phenyl which is substituted by trifluoromethyl, halogen or C₁ -C₄ -alkyl, or

A is a radical of the formula ##STR21## where R⁵ and R⁶ are each halogen or CF₃.

2. A cyclohexenol derivative of the formula I as defined in claim 1, where X is hydrogen.

3. A cyclohexenol derivative of the formula I as defined in claim 1, where R¹ is tetrahydropyranyl, tetrahydrothiopyranyl, 1-oxotetrahydrothiopyranyl or 1,1-dioxotetrahydrothiopyranyl.

4. A cyclohexanol derivative(I) as defined in claim 11, wherein R¹ is tetrahydropyran.

5. A cyclohexenol derivative of the formula I as claimed in claim 1, where R¹ is tetrahydrothiopyran-3-yl.

6. A cyclohexenol derivative of the formula I as defined in claim 1, where R¹ is tetrahydrothiopyran-3-yl, R² is n-propyl, R³ is ethyl, X is hydrogen, and A is benzoyl.

7. A cyclohexanol derivative of the formula I as defined in claim 1, where R¹ is tetrahydrothiopyran-3-yl, R² is n-propyl, R³ is ethyl, X is hydrogen, and A is 2-[4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl.

8. A cyclohexenol derivative of the formula I as defined in claim 1, wherein A is benzoyl.

9. A cyclohexenol derivative of the formula I as defined in claim 1, wherein A is 2-[4-(4-trifluoromethylphenoxy)-phenoxy]-propionyl.

10. A herbicidal composition containing an inert carrier and a herbicidally effective amount of a cyclohexenol derivative as defined in claim 1.

11. A herbicidal composition containing an inert carrier and a herbicidally effective amount of a cyclohexenol derivative of the formula I as defined in claim 2.

12. A herbicidal composition containing an inert carrier and a herbicidally effective amount of a cyclohexenol derivative of the formula I as defined in claim 3.

13. A process for controlling the growth of unwanted grassy plants, wherein the unwanted plants and/or the area to be kept free from unwanted plant growth are treated with a herbicidally effective amount of a cyclohexenol derivative of the formula I as defined in claim 1.

14. A process for controlling the growth of unwanted grassy plants, wherein the unwanted plants and/or the area to be kept free from unwanted plant growth are treated with a herbicidally effective amount of a cyclohexenol derivative of the formula I as defined in claim 8.

15. A process for controlling the growth of unwanted grassy plants, wherein the unwanted plants and/or the area to be kept free from unwanted plant growth are treated with a herbicidally effective amount of a cyclohexenol derivative of the formula I as defined in claim 9.