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US 5,034,393 AGranted
Fungicidal use of pyridopyrimidine, pteridine, pyrimidopyrimidine, pyrimidopyridazine, and pyrimido-1,2,4-triazine derivatives
AssigneeDowElanco
InventorsRonald E. Hackler, Glen P. Jourdan
Life of this patent
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Abstract
Fungicidal compositions contain as active ingredient a 4-substituted-pyrido[3,2-d]pyrimidine, -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, or -pyrimido[5,4-e]-1,2,4-triazine, for example 4-[2-(4-chlorophenyl)ethoxy]pyrido[2,3-d]pyrimidine.
Claims40
A fungicidal composition comprising a compound of formula (1):
- ##STR12## wherein or A, C, and D are N and B is CR.sup.1 ;
- a) A is N and B, E, and D are CR.sup.1 ;
- b) B is N and E, E, and D are CR.sup.1 ;
- c) E is N and A, B, and D are CR.sup.1 ;
- d) D is N and A, B, and E are CR.sup.1 ;
- e) A and D are N and B and E are CR.sup.1 ;
- f) B and D are N and A and E are CR.sup.1 ;
- g) E and D are N and A and B are CR.sup.1 ;
- h) A and E are N and B and D are CR.sup.1 ;
- i) A and B are N and E and D are CR.sup.1 ;
- j) A and B are N and E and D are CR.sup.1 ;
- k) A, E, and D are N and B is CR.sup.1 ;
- where R1 and R2 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 a bond or an alkylene chain one to six carbon atoms long, optionally including a carbocyclic ring, and optionally including a hetero atom selected from O, NR.sup.3, S, SO, SO.sub.2, or SiR.sup.20 R.sup.21, where R.sup.3 is as defined above and R.sup.20 and R.sup.21 are independently (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, or substituted phenyl, and optionally substituted with (C.sub.1 -C.sub.4) alkyl, (C.sub.2 -C.sub.4) alkenyl or -alkynyl, branched (C.sub.3 -C.sub.7) alkyl, (C.sub.3 -C.sub.7) cycloalkyl or -cycloalkenyl, halo, hydroxy, or acetyl, and
- Z is
- (a) a (C.sub.1 -C.sub.12) saturated or unsaturated hydrocarbon chain, straight chain or branched optionally including a hetero atom selected from O, S, SO, SO.sub.2, or SiR.sup.20 R.sup.21, where R.sup.20 and R.sup.21 are as defined above, and optionally substituted with halo, halo (C.sub.1 -C.sub.4) alkoxy, hydroxy, (C.sub.3 -C.sub.8) cycloalkyl or cycloalkenyl, or (C.sub.1 -C.sub.4) acyl;
- (b) (C.sub.3 -C.sub.8) cycloalkyl or cycloalkenyl, optionally substituted with (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, halo (C.sub.1 -C.sub.4) alkyl, halo (C.sub.1 -C.sub.4) alkoxy, halo, hydroxy, or (C.sub.1 -C.sub.4) acyl;
- (c) a phenyl group of the formula (2) ##STR13## where 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;
- (d) a furyl group of formula (3) ##STR14## where R.sup.18 is H, halo, halomethyl, CN, NO.sub.2, (C.sub.1 -C.sub.4) alkyl, (C.sub.3 -C.sub.4) branched alkyl, phenyl, or (C.sub.1 -C.sub.4) alkoxy;
- (e) a thienyl group of the formula (4) ##STR15## where R.sup.18 is as defined in paragraph (d);
- (f) a group of formula (5) or (6) ##STR16## where R.sup.18 is as defined in paragraph (d), J is N or CH, and G is O, NR.sup.19, or S, provided that if J is not N then G is NR.sup.19, where R.sup.19 is H, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) acyl, phenylsulfonyl, or substituted phenylsulfonyl;
- (g) a group selected from
- optionally substituted naphthyl, dihydronaphthyl, tetrahydronaphthyl, and decahydronaphthyl;
- optionally substituted pyridyl;
- optionally substituted indolyl;
- and 1,3-benzodioxolyl;
- or an acid addition salt of a compound of formula (1);
- provided that the following compounds are excluded:
- 1) pyrido[2,3-d]pyrimidines of formula (1) wherein X and NR.sup.3 in combination with a phytologically acceptable carrier.
27 more elements
Dependencies are inferred from the claim text.