# US 5,707,995 A · Pesticidal pyrimidine compounds

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- Number: US 5,707,995 A
- Document ID: US5707995A
- Status: Granted
- Kind: A
- Application number: 08/351,477
- Filed: 1995-07-24
- Granted: 1998-01-13
- Earliest claimed: 1992-07-17
- Assignees: American Cyanamid Company
- Inventors: David Munro; Royston Davis; Janet Anne Day; Jacqueline Anne Wilkin; William W. Wood
- Web page: https://patentgrep.com/patent/US5707995A

## CPC

- C07D 239/48: Two nitrogen atoms
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A61P 33/00: Antiparasitic agents
- C07D 239/52: Two oxygen atoms
- C07D 239/58: Two sulfur atoms
- C07D 239/60: Three or more oxygen or sulfur atoms
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I) in which X.sup.1 and X.sup.2 each represents oxygen; S(O).sub.n, n being 0, 1 or 2; or CO, CH.sub.2 or NR, R being hydrogen or alkyl; R.sup.1 and R.sup.10 are each hydrogen or halogen; R.sup.2 and R.sup.9 are each hydrogen, halogen, cyano, nitro, alkyl, halo-alkyl, alkoxy, alkylthio, amino, mono- or di-alkylamino, alkoxyalkyl, haloalkoxyalkyl or alkoxycarbonyl; R.sup.3 and R.sup.8 are each hydrogen, chlorine, alkyl, haloalkyl, haloalkenyl, halo-alkynyl, haloalkoxy, haloalkoxycarbenyl, haloalkylthio, haloalkoxyalkyl, haloalkylsulphinyl, or haloalkylsulphonyl, nitro or cyano; R.sup.4 and R.sup.7 are each hydrogen, halogen, alkyl or alkoxy; R.sup.5 is hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy, alkylthio, alkylsulphonyl or phenyl; and R.sup.6 is hydrogen or, when R.sup.5 is hydrogen, alkyl; provided that either each phenyl is unsubstituted or at least one of R.sup.3 and R.sup.8 is not hydrogen, have useful pesticidal activity.

## Claims

### Claim 1

A compound having the structural formula ##STR9## wherein X.sup.1 and X.sup.2 are the same and each represents an oxygen atom; a group S(O).sub.n in which n is 0, 1 or 2; or a group CO, CH.sub.2 or NR in which R represents a hydrogen atom or a C.sub.1-6 alkyl group;
R.sup.1 and R.sup.10 are the same or different and each represents a hydrogen atom or a halogen atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen atom, a halogen atom or a cyano, nitro, C.sub.1-6 alkyl, haloC.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, amino, mono- or di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkoxyC.sub.1-6 alkyl, haloC.sub.1-6 alkoxyC.sub.1-6 alkyl or (C.sub.1-6 alkoxy) carbonyl group;
R.sup.3 and R.sup.8 are the same or different and each represents a hydrogen atom, a chlorine atom, or a C.sub.1-6 alkyl, haloC.sub.1-6 alkyl, haloC.sub.1-6 alkoxy, haloC.sub.1-6 alkylthio, haloC.sub.2-6 alkenyl, haloC.sub.2-6 alkynyl, haloC.sub.1-6 alkoxyC.sub.1-6 alkyl, (haloC.sub.1-6 alkoxy) carbonyl, haloC.sub.1-6 alkylsulphinyl, haloC.sub.1-6 alkylsulphonyl, nitro or cyano group;
R.sup.4 and R.sup.7 are the same or different and each represents a hydrogen atom, a halogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;
R.sup.5 represents a hydrogen atom, a halogen atom, or a cyano, C.sub.1-6 alkyl, haloC.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl or phenyl group; and
R.sup.6 represents a hydrogen atom or, when R.sup.5 is hydrogen, a C.sub.1-6 alkyl group;
provided that at least one of R.sup.3 and R.sup.8 is other than hydrogen.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom, a sulphur atom or a group NH;
R.sup.1 and R.sup.10 are the same and each represents a hydrogen or a fluorine atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen atom, a halogen atom, a nitro, C.sub.1-4 alkyl or cyano group;
R.sup.3 and R.sup.8 are the same or different and each represents a hydrogen, fluorine or chlorine atom, or a nitro, C.sub.1-4 alkyl, haloC.sub.1-4 alkyl, haloC.sub.1-4 alkoxy, haloC.sub.2-4 alkenyl or (C.sub.1-4 alkoxy) carbonyl group provided that at least one of R.sup.3 and R.sup.8 is a haloC.sub.1-4 alkyl group;
R.sup.4 and R.sup.7 are the same or different and each represents a hydrogen or halogen atom or a C.sub.1-4 alkyl group;
R.sup.5 represents a hydrogen atom, a halogen atom or a haloC.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkylsulphinyl group; and
R.sup.6 represents a hydrogen atom or, when R.sup.5 is hydrogen, a methyl group.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom;
each of R.sup.1 and R.sup.10 represents a hydrogen atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen, fluorine or chlorine atom;
R.sup.3 and R.sup.8 are the same or different and each represents a trifluoromethyl or pentafluoroethyl group;
R.sup.5 represents a hydrogen or chlorine atom, or a methylthio group; and
R.sup.6 represents a hydrogen atom.

### Claim 4 (depends on 3)

The compound according to claim 3 selected from the group consisting of
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.,4-tetra-fluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-chloropyrimid ine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-(methylthio)p yrimidine;
4-›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-6-›(.alpha.,.alpha., .alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!pyrimidine; and
4,6-bis ›m-(1,1,2,2,2-pentafluoroethyl)phenoxy!pyrimidine.

### Claim 5 (depends on 4)

The compound according to claim 4 wherein the compound is 4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.a lpha.,.alpha.,4-tetra-fluoro-m-tolyl)oxy!pyrimidine.

### Claim 6 (depends on 1)

A method for controlling acarina and insects at a locus which method comprises applying to the locus an acaricidally or insecticidally effective amount of a compound having the structural formula ##STR10## wherein X.sup.1, X.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as described in claim 1.

### Claim 7 (depends on 6)

The method according to claim 6 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom, a sulphur atom or a group NH;
R.sup.1 and R.sup.10 are the same and each represents a hydrogen or a fluorine atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen atom, a halogen atom, a nitro, C.sub.1-4 alkyl or cyano group;
R.sup.3 and R.sup.8 are the same or different and each represents a hydrogen, fluorine or chlorine atom, or a nitro, C.sub.1-4 alkyl, haloC.sub.1-4 alkyl, haloC.sub.1-4 alkoxy, haloC.sub.2-4 alkenyl or (C.sub.1-4 alkoxy) carbonyl group provided that at least one of R.sup.3 and R.sup.8 is a haloC.sub.1-4 alkyl group;
R.sup.4 and R.sup.7 are the same or different and each represents a hydrogen or halogen atom or a C.sub.1-4 alkyl group;
R.sup.5 represents a hydrogen atom, a halogen atom or a haloC.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkylsulphinyl group; and
R.sup.6 represents a hydrogen atom or, when R.sup.5 is hydrogen, a methyl group.

### Claim 8 (depends on 7)

The method according to claim 7 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom;
each of R.sup.1 and R.sup.10 represents a hydrogen atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen, fluorine or chlorine atom;
R.sup.3 and R.sup.8 are the same or different and each represents a trifluoromethyl or pentafluoroethyl group;
R.sup.5 represents a hydrogen or chlorine atom, or a methylthio group; and
R.sup.6 represents a hydrogen atom.

### Claim 9 (depends on 8)

The method according to claim 8 wherein the compound is selected from the group consisting of
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.,4-tetra-fluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-chloropyrimid ine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-(methylthio)p yrimidine;
4-›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-6-›(.alpha.,.alpha., .alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!pyrimidine; and
4,6-bis›m-(1,1,2,2,2-pentafluoroethyl)phenoxy!pyrimidine.

### Claim 10 (depends on 6)

The method according to claim 6 wherein the acarina are mites.

### Claim 11 (depends on 1)

A method for controlling animal ectoparasites which method comprises applying to the skin or coat of an animal an ectoparisiticidally effective amount of a compound having the structural formula ##STR11## wherein X.sup.1, X.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as described in claim 1.

### Claim 12 (depends on 11)

The method according to claim 11 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom, a sulphur atom or a group NH;
R.sup.1 and R.sup.10 are the same and each represents a hydrogen or a fluorine atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen atom, a halogen atom, a nitro, C.sub.1-4 alkyl or cyano group;
R.sup.3 and R.sup.8 are the same or different and each represents a hydrogen, fluorine or chlorine atom, or a nitro, C.sub.1-4 alkyl, haloC.sub.1-4 alkyl, haloC.sub.1-4 alkoxy, haloC.sub.2-4 alkenyl or (C.sub.1-4 alkoxy) carbonyl group provided that at least one of R.sup.3 and R.sup.8 is a haloC.sub.1-4 alkyl group;
R.sup.4 and R.sup.7 are the same or different and each represents a hydrogen or halogen atom or a C.sub.1-4 alkyl group;
R.sup.5 represents a hydrogen atom, a halogen atom or a haloC.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkylsulphinyl group; and
R.sup.6 represents a hydrogen atom or, when R.sup.5 is hydrogen, a methyl group.

### Claim 13 (depends on 12)

The method according to claim 12 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom;
each of R.sup.1 and R.sup.10 represents a hydrogen atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen, fluorine or chlorine atom;
R.sup.3 and R.sup.8 are the same or different and each represents a trifluoromethyl or pentafluoroethyl group;
R.sup.5 represents a hydrogen or chlorine atom, or a methylthio group; and
R.sup.6 represents a hydrogen atom.

### Claim 14 (depends on 11)

The method according to claim 11 wherein the animal ectoparasites are ticks.

### Claim 15 (depends on 1)

A composition for controlling acarina, insects and animal ectoparasites which composition comprises a carrier and an acaricidally, insecticidally or animal ectoparasiticidally effective amount of a compound having the structural formula ##STR12## wherein X.sup.1, X.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as described in claim 1.

### Claim 16 (depends on 15)

The composition according to claim 15 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom, a sulphur atom or a group NH;
R.sup.1 and R.sup.10 are the same and each represents a hydrogen or a fluorine atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen atom, a halogen atom, a nitro, C.sub.1-4 alkyl or cyano group;
R.sup.3 and R.sup.8 are the same or different and each represents a hydrogen, fluorine or chlorine atom, or a nitro, C.sub.1-4 alkyl, haloC.sub.1-4 alkyl, haloC.sub.1-4 alkoxy, haloC.sub.2-4 alkenyl or (C.sub.1-4 alkoxy) carbonyl group provided that at least one of R.sup.3 and R.sup.8 is a haloC.sub.1-4 alkyl group;
R.sup.4 and R.sup.7 are the same or different and each represents a hydrogen or halogen atom or a C.sub.1-4 alkyl group;
R.sup.5 represents a hydrogen atom, a halogen atom or a haloC.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkylsulphinyl group; and
R.sup.6 represents a hydrogen atom or, when R.sup.5 is hydrogen, a methyl group.

### Claim 17 (depends on 16)

The composition according to claim 16 wherein
each of X.sup.1 and X.sup.2 represents an oxygen atom;
each of R.sup.1 and R.sup.10 represents a hydrogen atom;
R.sup.2 and R.sup.9 are the same or different and each represents a hydrogen, fluorine or chlorine atom;
R.sup.3 and R.sup.8 are the same or different and each represents a trifluoromethyl or pentafluoroethyl group;
R.sup.5 represents a hydrogen or chlorine atom, or a methylthio group; and
R.sup.6 represents a hydrogen atom.

### Claim 18 (depends on 17)

The composition according to claim 17 wherein the compound is selected from the group consisting of
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.,4-tetra-fluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-chloropyrimid ine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-2-(methylthio)p yrimidine;
4-›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!-6-›(.alpha.,.alpha., .alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4-›(4-chloro-.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)oxy!-6-›(.alpha.,.al pha.,.alpha.-trifluoro-m-tolyl)oxy!pyrimidine;
4,6-bis›(.alpha.,.alpha.,.alpha.,4-tetrafluoro-m-tolyl)oxy!pyrimidine; and
4,6-bis›m-(1,1,2,2,2-pentafluoroethyl)phenoxy!pyrimidine.

### Claim 19 (depends on 1)

A process for the preparation of a compound having the structural formula I as claimed in claim 1 in which R.sup.1 =R.sup.10, R.sup.2 =R.sup.9, R.sup.3 =R.sup.8 and R.sup.4 =R.sup.7, which process comprises reacting under basic conditions a 4,6-dihalopyrimidine compound having the structural formula ##STR13## in which R.sup.5 and R.sup.6 are as defined in claim 1 and each of Hal.sup.1 and Hal.sup.2, independently, represents a halogen atom, with a compound having the structural formula ##STR14## in which X represents a group CH.sub.2 Hal, COHal, OH, SH or NRH, Hal represents a halogen atom, and R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1, in a molar ratio of at least 1:2.

### Claim 20 (depends on 1)

An intermediate compound having the structural formula ##STR15## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as described in claim 1; and R.sup.11 represents an OH or NH.sub.2 group, provided that at least one of R.sup.3 and R.sup.8 is a haloC.sub.1-6 alkyl group.