# US 6,297,251 B1 · Fungicidal trifluorophenyl-triazolopyrimidines

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- Number: US 6,297,251 B1
- Document ID: US6297251B1
- Status: Granted
- Kind: B1
- Application number: 09/457,250
- Filed: 1999-12-08
- Granted: 2001-10-02
- Earliest claimed: 1999-12-08
- Assignees: American Cyanamid Company
- Inventors: Klaus-Juergen Pees; Guido Albert
- Web page: https://patentgrep.com/patent/US6297251B1

## CPC

- C07D 487/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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 novel compounds of formula I: (R1, R2 and Hal are defined in the specification) show selective fungicidal activity. The new compounds are processed with carriers and adjuvants to fungicidal compositions.

## Claims

### Claim 1

A compound of the formula I
in which
R1 and R2 each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group other than optionally substituted 2,2,2-trifluoroethyl groups, or
R1 and R2 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring, and
Hal represents a halogen atom,
provided that Hal is other than chlorine when R1 represents a straight or branched C1-C6-alkyl or C3-C6-cycloalkyl group and R2 represents a hydrogen atom or when R1 and R2 together with the interjacent nitrogen atom represent a piperidine group optionally substituted with one or two C1-C6-alkyl groups.

### Claim 2 (depends on 1)

A compound according to claim 1 in which
R1 represents straight chained or branched C1-C6-alkyl, C1-C6-haloalkyl or straight chained or branched C2-C6-alkenyl, and R2 represents hydrogen or C1-C6-alkyl, or
R1 and R2 together with the interjacent nitrogen atom represent a heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C1-C6-alkyl groups.

### Claim 3 (depends on 1)

A compound according to claim 1 in which R2 represents a hydrogen atom.

### Claim 4 (depends on 1)

A compound according to claim 1 in which R1 and R2 together with the interjacent nitrogen atom represent a heterocyclic ring selected from 4-methylpiperidin-1-yl, 2-methylpiperidin-1-yl, 5,6-dihydro-2H-pyridin-1-yl, 2-ethylpiperidin-1-yl and azepan-1-yl.

### Claim 5 (depends on 1)

A compound according to claim 1 selected the group consisting of:
5-chloro-7-(N,N-diethylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-ethyl-N-2-methylallylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(4-thiomorpholino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(azepan-1-yl)6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidine;
5-chloro-7-(N-allyl-N-ethylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-norborn-2-ylamino)-6-(2,4,6trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(8-aza-1,5-dioxaspiro[5.5]undecan-8-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(1,2,5,6-tetrahydropyrid-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-methyl-N-2-methylallylamino)-6-(2,4,6trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-ethyl-N-isopropylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine;
5-chloro-7-(N-allyl-N-2-methylpropylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-isopropyl-N-2-methylpropylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine; 5-chloro-7-[N,N-di-(2-methylpropylamino)]-6(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-{N-2-methylpropyl-N-[2-(1,1,1-trifluoropropyl)-amino]}-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-{N-methyl-N-[2-(1,1,1-trifluoropropyl)-amino]}6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-1-phenylethyl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-ethyl-N-2-methylpropylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-but-2-yl-N-methylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-cyclopentyl-N-methylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-(2,2,2-trifluoroethyl)-N-(trimethylsilylmethyl)-amino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(3-hydroxypiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(3-hydroxypyrollidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-(2-(3-fluorophenyl)-ethyl)-amino]-6(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-(1-(4-methylphenyl)-ethyl)-amino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine;
5-chloro-7-(N-4-tert-butylcyclohexyl-amino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(tetrahydropyrid-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(1,2,3,6-tetrahydropyrid-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(N-2-hyroxypropylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(4-hydroxypiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(4-hydroxymethylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-([1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-(1-phenyl-2,2,2-trifluoroethyl)-amino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-2-(1,1,1-tifluorobutyl)-amino]-6-(2,4,6trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-(3-methylbutyl)-N-methylamino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[N-2-(3-methyl-1,1,1-trifluorobutyl)-amino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-(1,1,3,3-tetramethylbutylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[3-(2-methylhexyl)-amino]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
5-chloro-7-[2-(5-methylhexyl)-amino]-(2,4,6trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine.

### Claim 6

A process for the preparation of a compound of formula I
in which
R1 and R2 each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group other than optionally substituted 2,2,2-trifluoroethyl groups, or
R1 and R2 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring, and
Hal represents a halogen atom
which comprises treating a compound of the formula II
in which
Hal is as defined above,
with an amine of the formula III
in which
R1 and R2 are as defined above,
to produce a compound of formula I.

### Claim 7

A compound of formula II
in which
Hal is a halogen atom.

### Claim 8

5,7-Dihydroxy-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine.

### Claim 9 (depends on 1)

A fungicidal composition which comprises a carrier, and as active agent, at least one compound of formula I as defined in claim 1.

### Claim 10 (depends on 1, 9)

A method of combating fungus at a locus which comprises treating the locus with a fungicidally effective amount of a compound of formula I as defined in claim 1 or a composition as defined in claim 9.

### Claim 11

5-chloro-7-(N-3-chlorotricyclo[2.2.1.02,6]hept-5-ylaminio)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine.