# US 4,397,676 A · N-Phosphonomethylglycine derivatives

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- Number: US 4,397,676 A
- Document ID: US4397676A
- Status: Granted
- Kind: A
- Application number: 06/369,425
- Filed: 1982-04-19
- Granted: 1983-08-09
- Earliest claimed: 1982-03-08
- Assignees: Geshuri Laboratories Ltd.
- Inventors: Izhak Bakel
- Web page: https://patentgrep.com/patent/US4397676A

## CPC

- A01N 57/20: containing acyclic or cycloaliphatic radicals
- C07F 9/3813: {N-Phosphonomethylglycine; Salts or complexes thereof}
- 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
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The invention provides N-Phosphonomethylglycine derivatives of the general formula I ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from --OH and --OR.sub.4 wherein R.sub.4 is a salt forming cation iminourea derivative of the general formula II ##STR2## wherein R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 are independently ##STR3## or an aryl, cycloalkyl or straight or branched chain alkyl or alkenyl group optionally substituted by hydroxy or halogen, or an alkylaryl group, provided that at least one but no more than two of R.sub.1, R.sub.2 or R.sub.3 are OR.sub.4 ; no more than two R.sub.5, R.sub.5', R.sub.6, R.sub.6' are aryl or substituted aryl; and no more than one of R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 is CH.sub.2 OH. The invention also provides a process for preparing the above N-Phosphonomethylglycine imino urea salts as well as providing phytotoxic compositions containing the same.

## Claims

### Claim 1

N-Phosphonomethylglycine derivatives of the general formula I ##STR12## wherein R.sub.1, R.sub.2 and R.sub.3 are independently selected from --OH and --OR.sub.4 wherein R.sub.4 is a salt forming cation iminourea derivative of the general formula II ##STR13## wherein R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 are independently ##STR14## or an aryl, cycloalkyl or straight or branched chain alkyl or alkenyl group optionally substituted by hydroxy or halogen, or an alkylaryl group, provided that
(a) at least one but no more than two of R.sub.1, R.sub.2 or R.sub.3 are OR.sub.4,
(b) no more than two R.sub.5, R.sub.5', R.sub.6, R.sub.6' are aryl or substituted aryl; and
(c) no more than one of R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 is CH.sub.2 OH.

### Claim 2 (depends on 1)

N-Phosphonomethylglycine iminourea salts according to claim 1 wherein R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 are independently selected from H, NH.sub.2, phenyl, alkyl and tolyl.

### Claim 3 (depends on 1)

N-Phosphonomethylglycine iminourea salts according to claim 1 wherein R.sub.5, R.sub.5', R.sub.6, R.sub.6' and R.sub.7 are all hydrogen.

### Claim 4 (depends on 1)

N-Phosphonomethylglycine iminourea salts according to claim 1 wherein one of R.sub.5, R.sub.5', R.sub.6, R.sub.6' is an amino group and the others are hydrogen.

### Claim 5 (depends on 1)

N-Phosphonomethylglycine iminourea salts according to claim 1 selected from the group wherein R.sub.5 or R.sub.5' is phenyl or methylphenyl and the other is hydrogen or R.sub.6 or R.sub.6' is phenyl or methylphenyl and the other is hydrogen.

### Claim 6 (depends on 1)

N-Phosphonomethylglycine derivatives according to claim 1 wherein R.sub.1 and R.sub.2 are OR.sub.4 and R.sub.3 is hydroxy.

### Claim 7 (depends on 1)

N-Phosphonomethylglycine derivatives according to claim 1 wherein R.sub.2 is OR.sub.4 and R.sub.1 and R.sub.3 are hydroxy.

### Claim 8 (depends on 1)

N-Phosphonomethylglycine derivatives according to claim 1 wherein one of R.sub.5, R.sub.5', R.sub.6 and R.sub.6' is an alkyl group and the rest are hydrogen.

### Claim 9 (depends on 1)

N-Phosphonomethylglycine derivatives according to claim 1 wherein said alkyl and alkenyl groups contain up to 6 carbon atoms.

### Claim 10 (depends on 1)

N-Phosphonomethylglycine derivatives according to claim 1 wherein said halogen is chlorine.

### Claim 11 (depends on 1)

A phytotoxic composition comprising an adjuvant and an effective amount of one or more N-phosphonomethylglycine iminourea salts as claimed in claim 1.

### Claim 12 (depends on 1)

A method of controlling vegetation comprising applying a phytotoxic amount of a compound as claimed in claim 1.