# US 4,400,201 A · Novel pyrimidinyl ethers, their use as herbicides, herbicidal compositions comprising said pyrimidinyl ethers and processes for the preparation thereof

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- Number: US 4,400,201 A
- Document ID: US4400201A
- Status: Granted
- Kind: A
- Application number: 06/329,260
- Filed: 1981-12-10
- Granted: 1983-08-23
- Earliest claimed: 1980-12-15
- Assignees: Sandoz Ltd.
- Inventors: Karlheinz Milzner
- Web page: https://patentgrep.com/patent/US4400201A

## CPC

- C07D 239/47: One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- 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

## Abstract

Pyrimidines having an amino group in the 2-position and a cyclopropylmethoxy group in the 4-position of the pyrimidine nucleus. Compounds according to the invention have valuable herbicidal activity, particularly after pre-emergence application in cotton and sunflower.

## Claims

### Claim 1

A compound of formula I, ##STR31## wherein either R.sub.1 is H or (C.sub.1-18)alkyl, (C.sub.1-18)alkyl substituted by up to 2 substituents selected from (C.sub.1-4)alkoxy or 2-tetrahydrofuryl; (C.sub.1-18)alkenyl; (C.sub.3-8)-cycloalkyl or (C.sub.3-8)cycloalkyl-(C.sub.1-5)alkyl, unsubstituted or substituted by up to 2 halogens selected from fluorine, chlorine and bromine; phenyl unsubstituted or substituted by up to 3 substituents selected from halogen of the group fluorine, chlorine and bromine (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy;
and R.sub.2 is H, (C.sub.1 -C.sub.5)alkyl,
or R.sub.1 and R.sub.2 together are a (C.sub.4 -C.sub.6)alkylene chain,
Y.sub.1 and Y.sub.2 independently are H or halogen selected from fluorine, chlorine or bromine,
R.sub.3, R.sub.4 and R.sub.5 independently are H, (C.sub.1 -C.sub.5)alkyl unsubstituted or substituted by halogen selected from fluorine, chlorine or bromine,
R.sub.6 is (C.sub.1 -C.sub.5)alkyl, and
R.sub.7 is H or (C.sub.1 -C.sub.5)alkyl in free base or acid addition salt form.

### Claim 2 (depends on 1)

A compound according to claim 1 of formula Ia, ##STR32## wherein R.sub.1 ' is (C.sub.1-18)alkyl, and
Y.sub.1, R.sub.3, R.sub.4 and R.sub.5 are as defined in claim 1,
in free base or acid addition salt form.

### Claim 3 (depends on 2)

A compund according to claim 2, selected from the group consisting of compounds wherein R.sub.1 ', Y.sub.1, R.sub.3, R.sub.4 and R.sub.5, are
(a) CH(CH.sub.3).sub.2, Cl, CH.sub.3, H and H respectively
(b) n-C.sub.3 H.sub.7, Cl, H, H and H respectively
(c) CH(CH.sub.3).sub.2, Cl H, H and H respectively
(d) CH(CH.sub.3).sub.2, Br, H, H and H respectively
(e) 2-C.sub.4 H.sub.9, Cl, H, H and H respectively
(f) CH(CH.sub.3).sub.2, H, H, H and H respectively
in free base or acid addition salt form.

### Claim 4 (depends on 1)

A herbicide, comprising a compound as claimed in claim 1, in free base or herbicidally acceptable acid addition salt form, and an herbicidally acceptable diluent.

### Claim 5 (depends on 1)

A method of combatting weeds, which comprises applying thereto or to the locus thereof a herbicidally effective amount of a compound of claim 1, in free base or herbicidally acceptable acid addition salt form.

### Claim 6 (depends on 1)

A method of combatting weeds in a crop locus, which comprises applying to said locus a selective herbicidally effective amount of a compound of claim 1, in free base or herbicidally acceptable acid addition salt form.

### Claim 7 (depends on 6)

A method according to claim 6, wherein the compound is applied pre-emergence and wherein the crop is cotton or sunflower.