# US 4,394,153 A · Herbicidal aryl esters of N-[(heterocyclic)-aminocarbonyl]sulfamic acid

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- Number: US 4,394,153 A
- Document ID: US4394153A
- Status: Granted
- Kind: A
- Application number: 06/261,751
- Filed: 1981-05-18
- Granted: 1983-07-19
- Earliest claimed: 1980-07-11
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: James J. Reap
- Web page: https://patentgrep.com/patent/US4394153A

## CPC

- C07D 521/00: Heterocyclic compounds containing unspecified hetero rings
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C07D 491/04: Ortho-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

## Abstract

The compounds are of the class of aryl esters of N-[(heterocyclic)aminocarbonyl]sulfamic acid, such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamic acid, (2-methylsulfonyloxy)-phenyl ester, useful for weed control in crops, brush control and plant growth retardation.

## Claims

### Claim 1

A compound of the formula: ##STR46## where Q is O or NR.sub.5 ;
R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or ##STR47## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2 or C.sub.1 -C.sub.2 alkyl; R.sub.3 is H, F, Cl, Br or CH.sub.3 ;
R.sub.4 is H, CH.sub.3 or OCH.sub.3 ;
R.sub.5 is C.sub.1 -C.sub.4 alkyl;
R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3 ;
A is ##STR48## X is NH.sub.2, N(CH.sub.3).sub.2, NHCH.sub.3, C.sub.1 -C.sub.4 alkyl, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CF.sub.3 or C.sub.1 -C.sub.3 alkyl substituted with 1-3 atoms of F, Cl or Br;
Y is H, CH.sub.3, OCH.sub.3 or Cl;
Z is CH, CCH.sub.3, CBr, CCl, CF or CI
provided that:
(1) when Y is Cl, then Z is CH and X is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3 or OCH.sub.3 ; and
(2) when Y is H, then X is OCH.sub.3, CH.sub.3 or CH.sub.2 OCH.sub.3, and Z is CH, CCH.sub.3, CBr, CCl, CF or CI.

### Claim 2 (depends on 1)

A compound of claim 1 where R.sub.5 is CH.sub.3 and R.sub.4 is H or CH.sub.3.

### Claim 3 (depends on 2)

A compound of claim 2 where R.sub.1 is C.sub.1 -C.sub.4 alkyl or CF.sub.3.

### Claim 4 (depends on 3)

A compound of claim 3 where R.sub.2 is H.

### Claim 5 (depends on 4)

A compound of claim 4 where R.sub.3 is H.

### Claim 6 (depends on 5)

A compound of claim 5 where
R.sub.1 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ;
Q is O;
A is ##STR49## Z is CH.

### Claim 7 (depends on 6)

A compound of claim 6 where R.sub.4 is H.

### Claim 8 (depends on 7)

A compound of claim 7 where X and Y are independently CH.sub.3 or OCH.sub.3, and R.sub.1 is CH.sub.3.

### Claim 9 (depends on 1)

The compound of claim 1, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamic acid, [2-(methylsulfonyloxy)phenyl]ester.

### Claim 10 (depends on 1)

The compound of claim 1, N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]sulfamic acid, [2-(methylsulfonyloxy)phenyl]ester.

### Claim 11 (depends on 1)

The compound of claim 1, N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]sulfamic acid, [2-(methylsulfonyloxy)phenyl]ester.

### Claim 12 (depends on 1)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 13 (depends on 2)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 14 (depends on 3)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 15 (depends on 4)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 16 (depends on 5)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 17 (depends on 6)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 18 (depends on 7)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 19 (depends on 8)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid inert diluent.

### Claim 20 (depends on 1)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.

### Claim 21 (depends on 2)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.

### Claim 22 (depends on 3)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.

### Claim 23 (depends on 4)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.

### Claim 24 (depends on 5)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.

### Claim 25 (depends on 6)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.

### Claim 26 (depends on 7)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.

### Claim 27 (depends on 8)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 8.

### Claim 28

A method for controlling the growth of undesired vegetation in rice without damage to the rice which comprises applying to the locus to be protected an effective amount of N-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]sulfamic acid, [2-(methylsulfonyloxy)-phenyl]ester.