# US 4,400,198 A · Herbicidal tetrahydrofuran derivatives

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- Number: US 4,400,198 A
- Document ID: US4400198A
- Status: Granted
- Kind: A
- Application number: 06/283,704
- Filed: 1981-07-16
- Granted: 1983-08-23
- Earliest claimed: 1980-01-21
- Assignees: Shell Oil Company
- Inventors: Alexander F. Orr; Michael D. Barker
- Web page: https://patentgrep.com/patent/US4400198A

## CPC

- C07D 307/32: Oxygen atoms
- A01N 43/08: with oxygen as the ring hetero atom
- A01N 43/32: six-membered rings
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/20: N-Aryl derivatives thereof
- C07C 43/15: containing only non-aromatic carbon-to-carbon double bonds
- C07D 307/14: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 307/20: Oxygen atoms
- C07D 307/30: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 493/10: Spiro-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Compounds of the general formula ##STR1## wherein each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl or aryl group, or R.sup.1 and R.sup.2 together represent an optionally substituted alkylene group; each of X and Y independently represents one of the groups CR.sup.6 R.sup.7, C=O, C=N--Z, CH--NH.sub.2 ##STR2## in which n is 2 or 3; R.sup.6 represents a hydrogen atom, an optionally substituted alkyl or aryl group or a group of formula --OA in which A represents a hydrogen atom, a heterocyclyl group, an acyl group derived from a carboxylic or a substituted carbamic acid, or a group CR.sup.10 R.sup.11 R.sup.12 ; R.sup.7 represents a hydrogen atom or an optionally substituted alkyl or aryl group; Z represents a hydroxy, alkoxy, acyloxy, amino, alkylamino or dialkylamino group; R.sup.3 represents a hydrogen atom or an optionally substituted alkyl group; each of R.sup.4 and R.sup.5 independently represents a hydrogen atom or an optionally substituted alkyl group; each of R.sup.8 and R.sup.9 independently represents a hydrogen atom, an alkyl group or an aryl group; each of R.sup.10 and R.sup.11 independently represents a hydrogen atom or an alkyl group; R.sup.12 represents an alkoxyalkoxy group a heterocyclyl group, an alkoxycarbonyl group, an optionally substituted aryl group, an alkylthio group or a substituted carboxamido group; and Ar represents an optionally substituted fully unsaturated ring having 5 or 6 atoms in the ring of which one is a nitrogen atom and the remainder are carbon atoms, or the N-oxide or an acid addition salt thereof, or Ar represents an optionally substituted phenyl group; with the proviso that if both X and Y represent groups CR.sup.6 R.sup.7, at least one substituent R.sup.6 is a group --OA; exhibit useful herbicidal activity.

## Claims

### Claim 1

A tetrahydrofuran derivative of the formula ##STR14## wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, a methyl group or an ethyl group, or R.sup.1 and R.sup.2 together represent a pentamethylene group; R.sup.3 represents a methyl, halomethyl, ethyl or methoxymethyl group, and Ar represents phenyl, 2-fluorophenyl, 2-chlorophenyl, 2,6-dichlorophenyl or 2-pyridyl.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R.sup.1 and R.sup.2 are methyl groups and R.sup.3 is an ethyl group.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein Ar is a 2-fluorophenyl group.

### Claim 4 (depends on 2)

A compound according to claim 2 wherein Ar is a 2-chlorophenyl group.

### Claim 5 (depends on 2)

A compound according to claim 2 wherein Ar is a 2,6-dichlorophenyl group.

### Claim 6 (depends on 2)

A compound according to claim 2 wherein Ar is a 2-pyridyl group.

### Claim 7 (depends on 1)

A herbicidal composition which comprises a herbicidally effective amount of a compound according to claim 1, together with a carrier.

### Claim 8 (depends on 7)

A composition according to claim 7, which comprises at least two carriers, at least one of which is a surface-active agent.

### Claim 9 (depends on 1)

A method of combating undesired plant growth at a locus, which comprises treating the locus with a herbicidally effective amount of a compound according to claim 1, or a composition thereof.

### Claim 10 (depends on 2)

A compound according to claim 2 wherein Ar is phenyl.