# US 5,350,749 A · Pteridine derivatives

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- Number: US 5,350,749 A
- Document ID: US5350749A
- Status: Granted
- Kind: A
- Application number: 07/690,184
- Filed: 1991-04-22
- Granted: 1994-09-27
- Earliest claimed: 1989-07-27
- Assignees: DowElanco
- Inventors: Ronald E. Hackler; Glen P. Jourdan
- Web page: https://patentgrep.com/patent/US5350749A

## CPC

- C07D 471/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D 475/02: with an oxygen atom directly attached in position 4
- C07D 475/06: with a nitrogen atom directly attached in position 4
- C07D 487/04: 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

4-substituted-pyrido[3,2-d]pyridmidine, -pyrido[4,3-d]pyrimidine, -pyrido[3,4-d]pyrimidine, pyrido[2,3-d]pyrimidine, -pteridine, -pyrimido[4,5-d]pyrimidine, -pyrimido[4,5-c]pyridazine, -pyrimido[5,4-d]pyrimidine, -pyrimido[5,4-c]pyridazine, pyrimido[4,5-d]pyridazine, and pyrimido[5,4-e]-1,2,4-triazine derivatives, for example 4-[2-(4-chlorophenyl)ethoxy]pyrido[2,3-d]pyrimidine, are useful as fungicides, inseciticides and miticides.

## Claims

### Claim 1

A compound of the formula (1) ##STR12## wherein a) A and D are N and B and E are CR.sup.1 ;
b) B and D are N and A and E are CR.sup.1 ;
c) E and D are N and A and B are CR.sup.1 ;
d) A and E are N and B and D are CR.sup.1 ;
e) A and B are N and E and D are CR.sup.1 ; or
f) B and E are N and A and D are CR.sup.1 ;
where R.sup.1 and R.sup.2 are independently H, halo, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, (C.sub.1 -C.sub.4) alkoxy, halo (C.sub.1 -C.sub.4) alkyl, phenyl, or substituted phenyl;
X is O, S, SO, SO.sub.2, NR.sup.3, or CR.sup.4 R.sup.5 where R.sup.3 is H, (C.sub.1 -C.sub.4) alkyl, or (C.sub.1 -C.sub.4) acyl, and R.sup.4 and R.sup.5 are independently H, (C.sub.1 -C.sub.4) acyl, (C.sub.1 -C.sub.4) alkyl, (C.sub.2 -C.sub.4) alkenyl or alkynyl, CN, or OH, or R.sup.4 and R.sup.5 combine to form a carbocyclic ring containing four to six carbon atoms;
Y is an alkylene chain 2 to 6 carbon atoms long;
Z is a phenyl group of the formula (2) ##STR13## wherein R.sup.6 to R.sup.10 are independently H, halo, I, (C.sub.1 -C.sub.10) alkyl, (C.sub.3 -C.sub.8) alkenyl or -alkynyl, branched (C.sub.3 -C.sub.6) alkyl, alkenyl or alkynyl, (C.sub.3 -C.sub.8) cycloalkyl or cycloalkenyl, halo (C.sub.1 -C.sub.7) alkyl, (C.sub.1 -C.sub.7) alkoxy, (C.sub.1 -C.sub.7) alkylthio, halo (C.sub.1 -C.sub.7) alkoxy, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, NO.sub.2, acetoxy, OH, CN, SiR.sup.11 R.sup.12 R.sup.13, OSiR.sup.11 R.sup.12 R.sup.13, NR.sup.14 R.sup.15, S(O)R.sup.16, or SO.sub.2 R.sup.17 where R.sup.11, R.sup.12, and R.sup.13 are independently (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, or substituted phenyl, R.sup.14 and R.sup.15 are independently H, (C.sub.1 -C.sub.4) alkyl, or (C.sub.1 -C.sub.4) acyl, and R.sup.16 and R.sup.17 are (C.sub.1 -C.sub.10) alkyl, phenyl, or substituted phenyl,
or an acid addition salt of a compound of formula (1).

### Claim 2 (depends on 1)

A compound of claim 1 wherein X is O.

### Claim 3 (depends on 1)

A compound of claim 1 wherein X is NR.sup.3.

### Claim 4 (depends on 3)

A compound of claim 3 wherein X is NH.

### Claim 5 (depends on 1)

A compound of claim 1 wherein A and D are N and B and E are CR.sup.1.

### Claim 6 (depends on 1)

A compound of claim 1 wherein at least one of R.sup.6 to R.sup.10 is
branched (C.sub.3 -C.sub.6) alkyl,
halo (C.sub.1 -C.sub.4) alkyl,
halo (C.sub.1 -C.sub.4) alkoxy,
phenyl,
substituted phenyl,
phenoxy,
substituted phenoxy,
phenylthio,
substituted phenylthio,
SiR.sup.11 R.sup.12 R.sup.13, or
OSiR.sup.11 R.sup.12 R.sup.13.