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US4146384A Expired / Lapsed US ⏱️ 0.0 years remaining

Tetrahydrofuran-ether compounds and herbicidal compositions

Assignee: Bayer AG
•
Filing: 1978-02-16
•
Granted: 1979-03-27
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Expires: 1998-02-16
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Abstract

Abstract New tetrahydrofuran-ether compounds of the formula ##STR1## in which A is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, or substituted phenyl, B 1 , b 2 , c 1 , c 2 , d 1 and D 2 , which are selected independently of one another, each represent hydrogen, alkyl, haloalkyl, alkoxyalkyl, phenyl, or substituted phenyl, R is aryl or substituted aryl; and X is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, phenyl, or substituted phenyl; Exhibit powerful herbicidal, especially selectively herbicidal, properties and are particularly useful as grass herbicides.

Inventors

  • 👤 Thomas Schmidt
  • 👤 Wilfried Draber
  • 👤 Ludwig Eue
  • 👤 Robert R. Schmidt

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 21:07
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/20; A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1786

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 326 words
Tetrahydrofuran-ether compound of the formula ##STR80## wherein A is hydrogen, straight-chain or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3-6 carbon atoms, alkenyl or alkynyl, each of up to 4 carbon atoms or phenyl optionally substituted by halogen, alkyl or alkoxy of 1 or 2 carbon atoms, or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms; B 1 , b 2 , c 1 , c 2 , d 1 and D 2 , which are selected independently of one another, each represent hydrogen, straight-chain or branched alkyl of 1 to 6 carbon atoms, alkoxyalkyl of 1 or 2 carbon atoms in each alkyl part, haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms or phenyl optionally substituted by halogen, alkyl or alkoxy of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms; R is optionally substituted aryl of 6 to 10 carbon atoms which can carry one or more substituents selected, independently, from halogen, alkyl and alkoxy, each with 1 to 4 carbon atoms, haloalkyl, haloalkoxy and haloalkylthio, each of up to 4 carbon atoms and up to 5 halogen atoms, phenyl, phenoxy and phenoxycarbonyl (which are each optionally substituted by halogen, alkyl or alkoxy, of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms), alkoxycarbonyl of 1 to 4 carbon atoms in the alkyl part, the methylenedioxo group, or the trimethylene, tetramethylene or pentamethylene radical; and X is hydrogen, straight-chain or branched alkyl of 1 to 4 carbon atoms, alkenyl or alkynyl of 2 to 4 carbon atoms, haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms and phenyl which is optionally substituted by halogen, alkyl or alkoxy, of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms, and up to 3 halogen atoms.
Claim 2
Dependent Claim 326 words
Tetrahydrofuran-ether compound of the formula ##STR80## wherein A is hydrogen, straight-chain or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3-6 carbon atoms, alkenyl or alkynyl, each of up to 4 carbon atoms or phenyl optionally substituted by halogen, alkyl or alkoxy of 1 or 2 carbon atoms, or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms; B 1 , b 2 , c 1 , c 2 , d 1 and D 2 , which are selected independently of one another, each represent hydrogen, straight-chain or branched alkyl of 1 to 6 carbon atoms, alkoxyalkyl of 1 or 2 carbon atoms in each alkyl part, haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms or phenyl optionally substituted by halogen, alkyl or alkoxy of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms; R is optionally substituted aryl of 6 to 10 carbon atoms which can carry one or more substituents selected, independently, from halogen, alkyl and alkoxy, each with 1 to 4 carbon atoms, haloalkyl, haloalkoxy and haloalkylthio, each of up to 4 carbon atoms and up to 5 halogen atoms, phenyl, phenoxy and phenoxycarbonyl (which are each optionally substituted by halogen, alkyl or alkoxy, of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms), alkoxycarbonyl of 1 to 4 carbon atoms in the alkyl part, the methylenedioxo group, or the trimethylene, tetramethylene or pentamethylene radical; and X is hydrogen, straight-chain or branched alkyl of 1 to 4 carbon atoms, alkenyl or alkynyl of 2 to 4 carbon atoms, haloalkyl of up to 2 carbon atoms and up to 3 halogen atoms and phenyl which is optionally substituted by halogen, alkyl or alkoxy, of 1 or 2 carbon atoms or haloalkyl of up to 2 carbon atoms, and up to 3 halogen atoms.
Claim 3
Dependent Claim 11 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein A is hydrogen.
Claim 4
Dependent Claim 11 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein A is alkyl.
Claim 5
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein A is alkenyl or alkynyl.
Claim 6
Dependent Claim 11 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein A is cycloalkyl.
Claim 7
Dependent Claim 14 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein A is phenyl or substituted phenyl.
Claim 8
Dependent Claim 29 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein one of B 1 , B 2 , C 1 , C 2 , D 1 and D 2 is hydrogen.
Claim 9
Dependent Claim 32 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein one of B 1 , B 2 , C 1 , C 2 , D 1 and D 2 is alkyl, haloalkyl or alkoxyalkyl.
Claim 10
Dependent Claim 32 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein one of B 1 , B 2 , C 1 , C 2 , D 1 and D 2 is phenyl or substituted phenyl.
Claim 11
Dependent Claim 11 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein X is hydrogen.
Claim 12
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein X is alkyl or haloalkyl.
Claim 13
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein X is alkenyl or alkynyl.
Claim 14
Dependent Claim 14 words
Tetrahydrofuran-ether compound as claimed in claim 1 wherein X is phenyl or substituted phenyl.
Claim 15
Dependent Claim 56 words
Compounds as claimed in claim 1 wherein R is optionally substituted aryl of 6 to 10 carbon atoms which can carry one or more substituents selected, independently, from halogen, alkyl and alkoxy, each with 1 to 4 carbon atoms, haloalkyl, haloalkoxy and haloalkylthio, each of up to 4 carbon atoms and up to 5 halogen atoms.
Claim 16
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR81## designated 3-(2-fluorobenzyloxy)-tetrahydrofuran.
Claim 17
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR82## designated 3-(2-chlorobenzyloxy)-tetrahydrofuran.
Claim 18
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR83## designated 3-(2-methylbenzyloxy)-tetrahydrofuran.
Claim 19
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR84## designated 3-(2-fluorobenzyloxy)-2,5-dimethyl-tetrahydrofuran.
Claim 20
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR85## designated 3-(2-methylbenzyloxy)-2,5-dimethyl-tetrahydrofuran.
Claim 21
Dependent Claim 13 words
Tetrahydrofuran-ether compound as claimed in claim 1 of the formula ##STR86## designated 3-(2-fluorobenzyloxy)2,2-dimethyl-tetrahydrofuran.
Claim 22
Dependent Claim 34 words
A herbicidal composition containing as active ingredient, herbicidally effective amount of a compound as claimed in claim 1 in admixture with a solid or liquefied gaseous diluent or liquid carrier containing a surface-active agent.
Claim 23
Dependent Claim 18 words
A composition as claimed in claim 21 containing from 0.1 to 95% of the active compound by weight.
Claim 24
Dependent Claim 24 words
A method of combating weeds which comprises applying to the weeds or their habitat, herbicidally effective amounts, a compound as claimed in claim 1.
Claim 25
Dependent Claim 28 words
A method as claimed in claim 23 wherein the active compound is applied to an area of agriculture in an amount of 0.1 to 10 kg per hectare.
Claim 26
Dependent Claim 28 words
A method as claimed in claim 24 wherein the active compound is applied to an area of agriculture in an amount of 0.2 to 5 kg per hectare.

References Cited (Backward Citations)

US2421569A Cited
US3046191A Cited
US3318916A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-03-26 1982-09-25 1983-03-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-03-26 1986-09-25 1987-03-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-03-26 1990-09-25 1991-03-27 $7700.00 Window Closed / Lapsed

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