# US 5,350,856 A · 2-(substituted imino)-1,3,4-dihydrothiadiazoles

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- Number: US 5,350,856 A
- Document ID: US5350856A
- Status: Granted
- Kind: A
- Application number: 07/463,190
- Filed: 1990-01-10
- Granted: 1994-09-27
- Earliest claimed: 1987-07-24
- Assignees: ICI Americas Inc.
- Inventors: Raymond A. Felix
- Web page: https://patentgrep.com/patent/US5350856A

## CPC

- C07D 285/135: Nitrogen atoms
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- A01N 47/40: the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N 53/00: Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- 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

This invention relates to a process for producing a compound of the formula ##STR1## comprising reacting a compound having the formula ##STR2## with cyanogen chloride or cyanogen bromide.

## Claims

### Claim 1

A process for producing a compound of the formula ##STR64## in which R is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, mono-, di-, tri- or tetrafluoroethyl, fluoroalkylthio, fluoroalkoxy, methylthio, methylsulfonyl, halomethylsulfonyl, C.sub.1 -C.sub.2 alkyl, or methoxy;
n is 1 or 2, provided that:
(a) is n is 1 and R is other than fluoro, the substituent R is located at the 3-position on the phenyl ring; and
(b) if n is 2, the substituents R are located at the 3- and 4-positions on the phenyl ring;
R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 alkyl thio, C.sub.3 -C.sub.4 alkenylthio, cyano, carbamyl, C.sub.1 -C.sub.4 mono-alkylcarbamyl, C.sub.1 -C.sub.2 carboalkoxy, or NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 are independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl; and
R.sub.2 is hydrogen, comprising reacting a compound having the formula ##STR65## with cyanogen chloride or cyanogen bromide.

### Claim 2 (depends on 1)

A process for producing a hydrohalide salt according to claim 1 comprising reacting a compound having the formula ##STR66## with cyanogen chloride or cyanogen bromide in the presence of a base.

### Claim 3

A process for producing a compound of the formula ##STR67## in which R is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, mono-, di-, tri- or tetrafluoroethyl, fluoro alkylthio, fluoroalkoxy, methylthio, methylsulfonyl, halomethyl sulfonyl, C.sub.1 -C.sub.2 alkyl, or methoxy;
n is 1 or 2, provided that:
(a) is n is 1 and R is other than fluoro, the substituent R is located at the 3-position on the phenyl ring; and
(b) if n is 2, the substituents R are located at the 3- and 4-positions on the phenyl ring;
R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenylthio, cyano, carbamyl, C.sub.1 -C.sub.4 mono-alkylcarbamyl, C.sub.1 -C.sub.2 carboalkoxy, or NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 are independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl; and
R.sub.2 is C.sub.1 -C.sub.4 mono- or dialkylcarbamyl; phenylcarbamyl; C.sub.1 -C.sub.4 mono-alkylthiocarbamyl; C.sub.4 -C.sub.6 ketoalkenyl; cyano; C.sub.1 -C.sub.4 alkylsulfonyl; C.sub.1 -C.sub.4 haloalkylsulfonyl; or ##STR68## in which Y is oxygen or sulfur; m is 0 or 1; and R.sub.5 is C.sub.1 -C.sub.10 alkyl; C.sub.2 -C.sub.10 alkenyl; C.sub.2 -C.sub.8 alkynyl if m is 0; C.sub.3 -C.sub.8 alkynyl in which the triple bond is separated from the oxygen or sulfur atom (Y) by at least one methylene group if m is 1; C.sub.1 -C.sub.8 haloalkyl if m is 0; C.sub.2 -C.sub.8 haloalkyl if m is 1; C.sub.2 -C.sub.10 alkoxyalkyl if m is 0; pyridyl if m is 0; C.sub.3 -C.sub.10 alkoxyalkyl in which the alkylene portion has at least two carbon atoms if m is 1; or R.sub.5 is
(R.sub.6).sub.p R.sub.7
in which p is 0 or 1; R.sub.6 is a C.sub.1 -C.sub.2 alkylene group and R.sub.7 is phenyl, halo-substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl, optionally substituted by from 1 to 3 methyl groups; C.sub.1 -C.sub.4 carboalkoxy; or a saturated or unsaturated heterocyclic ring containing from 5 to 6 atoms including from 1 to 2 hetero atoms selected from oxygen and sulfur, optionally substituted by from 1 to 3 methyl groups and optionally substituted by from 1 to 2 oxo groups; provided that when R.sub.1 is methylthio and R.sub.2 is isopropylcarboxy, then R is not 2-fluoro, comprising
(a) reacting a compound having the formula ##STR69## with cyanogen chloride or cyanogen bromide, optionally in the presence of a base; and
(b) reacting the product of step (a) with an acylating agent selected from the group consisting of compounds having the formula ##STR70## in which Z' is a halogen and isocyanates and isothiocyanates having the formula R.sub.9 --NCO or R.sub.9 NCS in which R.sub.9 is C.sub.1 -C.sub.4 alkyl or phenyl.