Claims
- 1. A compound of formula I ##STR130## wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by R.sub.4 ; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.4 is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 - C.sub.5 alkynyl or the radical (CH.sub.2).sub.n --X--C.sub.1 -C.sub.3 -alkyl;
- R.sub.7 is the group --NH.sub.2, ##STR131## R.sub.8 is hydrogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; R.sub.9 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.3 alkyl substituted by hydroxy, OR.sub.12, SR.sub.12 or by N(R.sub.12).sub.2, C.sub.3 -C.sub.6 cycloalkyl, cyclopropyl substituted by SR.sub.12, C.sub.3 -C.sub.10 alkenyl, C.sub.1 -C.sub.3 haloalkyl, phenyl, phenyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.2 haloalkyl, hydroxy, nitro, cyano, amino or by dimethylamino, 1- or 2-naphthyl, 1-, 2- or 3-pyridyl, ##STR132## R.sub.8 and R.sub.9, together with the carbon atom in the radical R.sub.7, are a saturated or unsaturated ring comprising 4 to 7 carbon atoms; R.sub.10 is CH(R.sub.8)R.sub.9, phenyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or cyanoalkyl having 2 or 3 carbon atoms in the alkyl radical; R.sub.11 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or cyanoalkyl having 2 or 3 carbon atoms in the alkyl radical; R.sub.12 is CH.sub.3 or C.sub.2 H.sub.5 ; X is oxygen or sulfur; Z is O, S, NH or NCH.sub.3 ; and n is 1 to 3; including the acid addition salts and metal salt complexes thereof.
- 2. A compound of formula I according to claim 1, wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by R.sub.4 ; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.4 is halogen or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or the radical (CH.sub.2).sub.n --X--C.sub.1 -C.sub.3 alkyl; R.sub.9 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.1 -C.sub.3 haloalkyl, phenyl or phenyl mono- to tri-substituted by halogen, methyl, methoxy, halomethoxy or by halomethyl; R.sub.8 and R.sub.9, together with the carbon atom in the radical R.sub.7, are a saturated or unsaturated ring comprising 5 or 6 carbon atoms; R.sub.7, R.sub.10, R.sub.11, R.sub.12 and Z are as defined under formula I; X is oxygen or sulfur; and n is 1 to 3.
- 3. A compound of formula I according to claim 1, wherein: R.sub.1 is phenyl or phenyl mono-substituted by halogen; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by OR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by OR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl substituted by methyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sub.9 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.1 -C.sub.3 haloalkyl, phenyl or phenyl mono- to tri-substituted by halogen, methyl, methoxy, halomethoxy or by halomethyl; R.sub.8 and R.sub.9, together with the carbon atom in the radical R.sub.7, are a saturated or unsaturated ring comprising 5 or 6 carbon atoms; and R.sub.7, R.sub.10, R.sub.11 and R.sub.12 are as defined under formula I.
- 4. A compound of formula I according to claim 1, wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by R.sub.4 ; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.4 is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or the radical (CH.sub.2).sub.n --X--C.sub.1 -C.sub.3 alkyl; R.sub.7 is --NH.sub.2 ; X is oxygen or sulfur; and n is 1 to 3; including the acid addition salts and metal salt complexes thereof.
- 5. A compound of formula I according to claim 4, wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by R.sub.4 ; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.4 is halogen; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or the radical (CH.sub.2).sub.n --X--C.sub.1 -C.sub.3 alkyl; X is oxygen or sulfur; and n is 1 to 3.
- 6. A compound of formula I according to claim 1, wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by halogen; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or the radical (CH.sub.2).sub.n --X--C.sub.1 -C.sub.3 alkyl; X is oxygen or sulfur; and n is 1 to 3.
- 7. A compound of formula I according to claim 1, wherein: R.sub.1 is phenyl or phenyl mono-substituted by chlorine or by fluorine; R.sub.2 is C.sub.1 -C.sub.5 alkyl, or is C.sub.1 -C.sub.2 alkyl substituted by OR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl substituted by methyl; and R.sub.5 is hydrogen or C.sub.1 -C.sub.2 alkyl.
- 8. A compound of formula I according to claim 7, wherein R.sub.3 is: methyl, fluoromethyl, chloromethyl, bromomethyl, C.sub.3 -C.sub.6 cycloalkyl or methoxymethyl.
- 9. A compound of formula I according to claim 1 from the group:
- N-(4-fluoromethyl-6-cyclopropylpyrimid-2-yl)-N-phenylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-m-fluorophenylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-p-fluorophenylhydrazine.
- 10. A compound of formula I according to claim 5 from the group:
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenylhydrazine; N-(4,6-dimethylpyrimid-2-yl)-N-phenylhydrazine; N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenylhydrazine.
- 11. A compound of formula I according to claim 1 from the group:
- N-(4,6-dimethylpyrimid-2-yl)-N-phenylpropionaldehyde hydrazone;
- N-(4,6-dimethylpyrimid-2-yl)-N-phenylisobutyraldehyde hydrazone;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenylisobutyraldehyde hydrazone;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenylpropionaldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenylpropionaldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-n-butyraldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenylisobutyraldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyltrichloroacetaldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-p-fluorophenylacetaldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-p-fluorophenylisobutyraldehyde hydrazone;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-m-fluorophenylisobutyraldehyde hydrazone;
- N-(4,6-dimethylpyrimid-2-yl)-N-phenyl-N'-methylhydrazine;
- N-(4,6-dimethylpyrimid-2-yl)-N-phenyl-N'-dimethylhydrazine;
- N-(4,6-dimethylpyrimid-2-yl)-N-phenyl-N'-n-propylhydrazine;
- N-(4,6-dimethylpyrimid-2-yl)-N-phenyl-N'-isobutylhydrazine;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenyl-N'-methylhydrazine;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenyl-N'-n-propylhydrazine;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-phenyl-N-dimethylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-N'-methylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-N'-isobutylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-N'-dimethylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-N'-diethylhydrazine;
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-phenyl-N'-methyl-N'-ethylhydrazine
- N-(4-methyl-6-cyclopropylpyrimid-2-yl)-N-p-fluorophenyl-N'-ethylhydrazine;
- N-(4-methyl-6-methoxymethylpyrimid-2-yl)-N-m-fluorophenyl-N'-isopropylhydrazine.
- 12. A process for the preparation of a compound of formula I according to claim 1, which comprises
- a) reacting a pyrimidine derivative of formula II ##STR133## with a phenylhydrazine derivative of formula III
- R.sub.1 --NH--NH--R (III)
- in the presence of a base, in an aprotic solvent and at temperatures of -50.degree. to 150.degree. C., wherein Y is halogen, the radical SO.sub.2 R.sub.6 of N.sup..sym. (CH.sub.3).sub.3, R.sub.6 is C.sub.1 -C.sub.4 alkyl, phenyl or phenyl substituted by methyl or by chlorine and R is hydrogen, CH(R.sub.8)R.sub.9, phenyl, C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.5 -alkenyl, C.sub.3 -C.sub.5 -alkynyl or cyanoalkyl having 2 or 3 carbons in the alkyl radical.
Priority Claims (2)
Number |
Date |
Country |
Kind |
3371/88 |
Sep 1988 |
CHX |
|
2579/89 |
Jul 1989 |
CHX |
|
Parent Case Info
This application is a continuation of application Ser. No. 403,250, filed Sep. 5, 1989, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4897396 |
Hubele |
Jan 1990 |
|
Foreign Referenced Citations (5)
Number |
Date |
Country |
0019450 |
Nov 1980 |
EPX |
0182190 |
May 1986 |
EPX |
0270111 |
Jun 1988 |
EPX |
2209470 |
Sep 1972 |
DEX |
WO8907599 |
Aug 1989 |
WOX |
Continuations (1)
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Number |
Date |
Country |
Parent |
403250 |
Sep 1989 |
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