CA2166754A1 - Fluorinated pyrimidines as herbicides - Google Patents

Fluorinated pyrimidines as herbicides

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Publication number
CA2166754A1
CA2166754A1 CA 2166754 CA2166754A CA2166754A1 CA 2166754 A1 CA2166754 A1 CA 2166754A1 CA 2166754 CA2166754 CA 2166754 CA 2166754 A CA2166754 A CA 2166754A CA 2166754 A1 CA2166754 A1 CA 2166754A1
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Prior art keywords
ome
alkyl
phenyl
carry
alkoxy
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CA 2166754
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French (fr)
Inventor
Uwe Josef Vogelbacher
Joachim Rheinheimer
Ernst Baumann
Uwe Kardorff
Ulf Mislitz
Karl-Otto Westphalen
Helmut Walter
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BASF SE
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Fluorinated pyrimidines of the formula I

(I) where A is one of the following radicals:

and where the symbols have the following meanings:

W is =O, =N-R3, =N-O-R3, =N-NR4R5;

X is -O-, -S-, and -NR6-;

Y and Z are halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino and/or dialkylamino;

R1, R2 and n have the meanings indicated in the description, and processes and intermediates for preparing the compounds I
are described.

Description

21~6~ 4 Fluorinated pyrimidines as herbicides The applications EP 223406, EP 249707, EP 249708; EP 287072, EP
315889, EP 321846, EP 402751 and WO 94-13065 describe pyrimidine derivatives having strong herbicidal action. Their action and their selectivity, however, are not always adequate.

It is an object of the present invention to find compounds which 10 overcome this disadvantage.

We have found that this object is achieved by fluorinated pyrimi-dines of the formula I

N

where A is one of the following radicals:

(R2)n~ (R2)n~ (R2)n ~ (R2)n~

W~ Rl W~ Rl _ W~--R

W~ Rl ~ (R2~n~ ~ W/~R

(R2)n~ (R2)n W~ ~ Rl W~ ~ Rl The symbols have the following meanings:

~66 ~'~ 4 W is =0~ =N-R3~ =N-o-R3, =N-NR4Rs;

X is -0-, -S- or -NR6-;

Y and Z are halogen, Cl-C6-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio, Cl-C4-alkylamino and/or di-Cl-C4-alkylamino;

10 Rl is hydrogen;

Cl-C6-alkyl, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl;

a succinyliminooxy group;

a 5-membered heteroaromatic comprising one to three nitrogen atoms which can carry one to four halogen atoms and/or one or two of the following radicals: Cl-C6-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy and/or Cl-C4-alkylthio;

a radical oR7;

a radical ()m - N

where R3 and R9 can be identical or different;

or a radical NH -- - Rl o o R2 is hydrogen;

halogen;

7~
, amino;

Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-alkylsulfonyl, Cl-C4-alkylamino, di-Cl-C4-alkylamino, which can carry one of the following substituents, which in the case of dialkylamino can be identical or different: C1-C4-alkoxy, Cl-C4-alkylthio, di-Cl-C4-alkylamino, thienyl, furyl, a five-membered aromatic heterocycle having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, it being possible for the five - hered ring heterocycles to carry one to three halogen atoms and/or one to three of the following radicalss nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl; or phenyl which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups; or phenoxy which i9 unsubstituted or ~ubstituted by one to three halogen atoms and/or one to three methyl groups, or a six-membered aromatic heterocycle having one to three nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl;
phenyl, substituted phenyl;
phenoxy, substituted phenoxy;

phenylthio, substituted phenylthio, phenylsulfonyl, substituted phenylsulfonyl;

a five-membered heteroaromatic having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
a benzo-fused 5-membered heteroaromatic, which can comprise one to three nitrogen atoms or a nitrogen atom and additionally an oxygen or sulfur atom and can carry one of the following radicals: halogen, nitro, cyano, C1-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, C1-C4-haloalkoxy or phenyl, which is unsubstituted or 21~7S~

substituted by one to three halogen atoms and/or one to three methyl groups;

a thienyl or furyl radical which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
a benzothienyl or benzofuryl radical, which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups a 6-membered heteroaromatic having one to four nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical which in each case can carry up to three halogen atoms and/or up to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
a 5-membered heteroaromatic bonded via an oxygen atom and having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzo-fused 5-membered heteroaromatic bonded via an oxygen atom, which can contain one to three nitrogen atoms or a nitrogen atom and additionally an oxygen or sulfur atom and can carry one of the following radicals: halogen, `~ ~lfi~751 nitro, cyano, Cl-C6-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a thienyl or furyl radical bonded via an oxygen atom, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzothienyl or benzofuryl radical bonded via an oxygen atom, which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a 6-membered heteroaromatic bonded via an oxygen atom and having one to four nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical bonded via an oxygen atom, which in each case can carry one to three halogen atoms and/or up to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-haloalkyl, Cl-C4-haloalkoxy or phenyl, which is unsubstituted or sub~tituted by one to three halogen atoms andtor one to three methyl groups;

a radical 21~7S4 N~F
~`~
~ 0~ N ~ Z

where Z', Xl', X2 and X3' have the meanings indicated above for Z, Xl, x2 and X3 can be identical to or different from them;
a group where W' and Rl' have the same meanings as ~ and Rl, and can be identical to or different from these units;

R3 is hydrogen, phenyl, substituted phenyl or Cl-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, which can carry one to three of the following substituents: halogen, Cl-C6-alkyl, Cl-C4-alkoxy, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl, carboxyl, Cl-C4-alkylthio, phenyl, substituted phenyl;

R4 is hydrogen, Cl-C6-alkyl or phenyl;
R5 is hydrogen, phenyl, substituted phenyl or Cl-C6-alkyl which can carry one to three of the following substituents:
halogen, Cl-C4-alkoxy, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl, carboxyl, Cl-C4-alkylthio, phenyl, substituted phenyl;

R6 is hydrogen, Cl-C6-alkyl, formyl, carbamoyl or Cl-C6-alkoxycarbonyl;

40 R7 is hydrogen, an alkali metal cation, the equivalent of an alkaline earth metal cation or an organic ammonium ion;

a C3-Cl2-cycloalkyl group which can carry one to three Cl-C4-alkyl radicals;
- 2~;6754 a C1-C4-alkyl group which can carry one to five halogen atoms and/or one or two of the following radicals:
Cl-C4-alkoxy, Cl-C4-alkylthio, cyano, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl, C3-Cl2-cycloalkyl, a radical -0-N=CRllRl2, where Rll and Rl2 can be identical or different, phenyl, phenoxy or phenylcarbonyl, it being possible for the aromatic radicals in turn to carry one to five halogen atoms and/or one to three of the following radicals: Cl-C6-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy and/or Cl-C4-alkylthio;

a Cl-C6-alkyl group which can carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic cont~ining one to three nitrogen atoms, which can carry one to four halogen atoms and/or one or two of the following radicals: Cl-C6-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloalkoxy and/or Cl-C4-alkylthio;

an alkyl group which in the 2-position carries one of the following radicals: Cl-Cl2-alkoxyimino, C3-Cl2-alkenyloxyimino, C3-C6-haloalkenyloxyimino or benzyloxyimino;

a C3-C6-alkenyl or a C3-C6-alkynyl group, it being possible for these groups in turn to carry one to five halogen atoms;

phenyl which is unsubstituted or mono- to trisubstituted by nitro, Cl-C6-alkyl or Cl-C6-alkoxy or mono- to pentasubstituted by halogen;

a radical -N=CRl3Rl4, where Rl3 and Rl4 can be identical or different;

a 5-membered aromatic heterocycle bonded via a nitrogen atom and having one to four nitrogen atoms in the ring or a benzo-fused 5-membered aromatic heterocycle bonded via a nitrogen atom and having one to three nitrogen atoms in the ring, which can be substituted by halogen, Cl-C6-alkyl or Cl-C4-haloalkyl;
R3 and R9 are hydrogen;

Cl-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, it being possible for these radicals in each case to carry one to five halogen atom~ and/or one or two of the following 2 1 6~75~

groups: C1-C4-alkoxy, Cl-C4-alkylthio, cyano, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl, di-Cl-C4-alkylamino, cyclo-C3-C12-alkyl;

cyclo-C3-Cl2-alkyl, which can carry one to three Cl-C4-alkyl substituents;
phenyl or substituted phenyl;

together are a C3-Cl2-alkylene chain closed to give ring or together are a C3-C12-alkylene chain closed to give a ring with a heteroatom, which can be oxygen, sulfur or nitrogen, and which in each case can carry one to three Cl-C4-alkyl substituents;
or a group fH~/
o R16 Rl is Cl-C6-alkyl or phenyl, which can carry one to four of the following substituents: halogen, nitro, cyano, Cl-C6-alkyl;

Rll and Rl2 are alkyl, which can carry a Cl-C4-alkoxy or Cl-C4-alkylthio group, or together are a C3-Cl2-alkylene chain;
Rl3 and Rl4 are Cl-C6-alkyl which can carry a phenyl radical, or a Cl-C4-alkoxy and/or a Cl-C4-alkylthio group, C3-Cl2-cycloalkyl, phenyl, or together are a C3-Cl2-alkylene chain which can carry one to five Cl-C6-alkyl groups and can be bridged by an alkylene chain;

Rl5 is hydrogen or C1-C6-alkyl which can be substituted by hydroxyl, amino, hydrogen sulfide, C1-C4-alkylthio, carboxyl, carbamoyl, guanidinyl, phenyl, hydroxyphenyl, imidazolyl or indolyl radicals or together with R9 is bonded via a C3-Cl2-alkylene chain to give a ring;

R16 i8 Cl-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;

m is 0 or 1;

21 667~ ~

n is 0, 1, 2 or 3;

substituted phenyl, substituted phenoxy, substituted phenylthio or substituted phenylsulfonyl in each case means that the phenyl ring can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, Cl-C6-alkyl, Cl-C4-halo-alkyl, Cl-C6-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio, Cl-C4-alkylamino, di-Cl-C4-alkylamino, Cl-C6-alkylcarbonyl, Cl-C6-alkoxycarbonyl, phenyl, phenyl substituted by one to three 10 halogen atoms or one to three methyl groups, phenoxy, phenoxy substituted by one to three halogen atoms or one to three methyl groups or, on two adjacent atoms, a unit -O-(CH2)o~0~, it being possible for o to assume the values 1 or 2.

Fluorinated pyrimidines of the formula I are preferred where A is one of the following radicals:

( R2 ) n~ ( R2 ) n~ ~ ( R2 ) n~

W~ Rl W~ Rl W~ R

(R2)n~(R2)n~J~ (R2)n W~ Rl W~ Rl W~ R

and where the symbols indicated have the following meanings:
W is =0;
X is -O- or -S-;

Y and Z are alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or dialkylamino;
40 Rl is hydrogen;

a 5-membered heteroaromatic containing one to three - nitrogen atoms;
a radical oR7;

2 1 ~ 6 7~

a radical ~R8 ()m--N

where R8 and R9 can be identical or different;
R2 is hydrogen;
halogen;

alkyl, alkenyl, alkynyl, alkoxy, alkylamino, dialkylamino, each of which can carry one of the following substituents, which can be identical or different in the case of dialkylamino: alkoxy, alkylthio, dialkylamino, thienyl, furyl, a fivc -mhered aromatic heterocycle having one to four nitrogen atom~ or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, it being possible for the fivc - hered ring heterocycles to carry one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl;
phenyl, substituted phenyl phenoxy, substituted phenoxy;
phenylthio, substituted phenylthio, phenylsulfonyl, substituted phenylsulfonyl;

a 5-membered heteroaromatic from the group consisting of pyrrole,-pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, 1,3,4-oxadiazole, furazan, 1,3,4-thiadiazole and 1,2,3-thiadiazole, which can carry one to three halogen atoms and/or one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a thienyl or furyl radical which can carry one to three halogen atoms and/or one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

-- 216~7~4 a benzothienyl or benzofuryl radical which can carry one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a 6-membered heteroaromatic from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,2,4-triazine and 1,3,5-triazine, which can carry one to three halogen atoms and/or one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical which in each case can carry up to three halogen atoms and/or up to three of the following radicals:
alkyl, alkoxy, haloalkyl, haloalkoxy;

a thienyl or furyl radical bonded via an oxygen atom, which can carry one to three halogen atoms and/or one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a benzothienyl or benzofuryl radical bonded via an oxygen atom, which can carry one to three of the following radicals: alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a 6-membered heteroaromatic bonded via an oxygen atom and from the group consisting of pyrimidine and 1,3,5-triazine, which can carry one to three halogen atom~ and/or one to three of the following radicals:
alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;

a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical bonded via an oxygen atom which can carry one to three of- the following radicals: alkyl, alkoxy, haloalkyl, haloalkoxy;
a radical Y' ~ 0~ Z ~

21 66 75 ~

where Y' and Z' have the meanings indicated above for X
and Z and can be identical to or different from them;
a group where W' and Rl' have the same meanings as W or R1, and can be identical to or different from these units;

R7 is hydrogen, an alkali metal cation, or the equivalent of an alkaline earth metal cation;

an alkyl group which can carry one to five halogen atom~
and/or one or two of the following radicals: alkoxy, alkylthio, cyano, alkylcarbonyl, alkoxycarbonyl, cycloalkyl;

an alkyl group which can carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic containing one to three nitrogen atoms;

an alkyl group which, in the 2-position, carries one of the following radicals: alkoxyimino or alkenyloxyimino;

an alkenyl or an alkynyl group, it being possible for these groups in turn to carry one to five halogen atoms;

phenyl which is unsubstituted or mono- to trisubstituted by nitro or alkyl or mono- to pentasubstituted by halogen;-a radical -N=CRl3Rl4, where Rl3 and Rl4 can be identical or different;
0 R~ and R9 are hydrogen;
alkyl, alkenyl, alkynyl;
cycloalkyl;
phenyl or substituted phenyl;

-- 21~67~ 1 together an alkylene chain closed to give a ring or together an alkylene chain closed to give a ring and containing a heteroatom which can be oxygen, sulfur or nitrogen;

Rl3 and Rl4 are alkyl which can carry a phenyl radical, cycloalkyl, phenyl or together an alkylene chain;

m is 0 or 1;
n is 0, 1, 2 or 3;

where substituted phenyl, substituted phenoxy, substituted phenylthio, substituted phenylsulfonyl means that the phenyl ring can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, dialkylamino, alkylcarbonyl or, on two adjacent atoms, a unit -0-(CH2)o~O~, it being possible for o to assume the values 1 or 2.

(R2)n~J~ (R2)n~ (R2)n~

W~ Rl W~ Rl W~ R

and where the symbols indicated have the following meanings:
30 W is =0;
X is -0- or -S-;
Y and Z are alkoxy;
R1 is a radical oR7;
R2 is hydrogen;
gO halogen;
alkyl, alkoxy, dialkylamino;
phenyl, substituted phenyl;

21667S~

a 5-membered heteroaromatic from the group consisting of pyrazole and thiazole, which can carry one of the following radicals: halogen, alkoxy a thienyl radical which can carry a halogen atom and/or the following radical: alkoxy;

a 6-membered heteroaromatic from the group consisting of pyridine, pyrimidine and 1,3,5-triazine, which can carry one of the following radicals: halogen, alkoxy;

a thienyl or furyl radical bonded via an oxygen atom, which can carry a halogen atom and/or the following radical: alkoxy;

a 6-membered heteroaromatic bonded via an oxygen atom and from the group consisting of pyrimidine and 1,3,5-triazine, which can carry one of the following radicals: halogen, alkoxy; 0 a radical Y' N ~ F

~ O/~N~Z

where Y~ and Z~ have the meanings indicated above for X
and Z and can be identical to or different from them;
a group W
~/
Rl ' where W' is an alkoxyimino group and Rl' is hydrogen or an alkyl group;
-R7 is hydrogen or an alkali metal cation;

216~754 .

an alkyl group which can carry one or two of the following radicals: alkoxy, alkylthio;
an alkenyl or an alkynyl group;

phenyl which is unsubstituted or monosubstituted by nitro or monosubstituted by halogen;

a radical -N=CRl3Rl4, where Rl3 and Rl4 can be identical or different;
n is l;

where substituted phenyl, substituted phenoxy, substituted phenylthio or substituted phenylsulfonyl means that the phenyl ring can carry one or two of the following radicals: alkoxy, alkylthio, a unit -0-(CH2)o~0~ on two adjacent atoms, it being possible for o to assume the values 1 or 2.
The substituents mentioned in the description preferably have the following meanings:

Cl-C6-alkyl: methyl, ethyl, l-propyl, 2-propyl, l-butyl, 2-butyl, 2-methylpropyl, l,l-dimethylethyl, l-pentyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl, 2-methyl-2-butyl, 3-methyl-2-butyl, l,l-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, l-hexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 30 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 3,3-dimethyl-2-butyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, in particular methyl, ethyl, propyl, 2-propyl, butyl, 2-butyl, l,l-dimethylethyl, pentyl, 2,2-dimethylpropyl, hexyl;

Cl-C4-haloalkyl: chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 40 1,1,2,2-tetrafluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-1,1,2-trifluoroethyl and pentafluoroethyl, decafluorobutyl, l,l-bis-trifluoromethyl-2,2,2-trifluoroethyl, preferably difluoromethyl, trifluoromethyl, trichloromethyl and chlorodifluoromethyl;

., 2166~sia~ .

C3-C6-alkenyl: propenyl, l-butenyl, 2-butenyl, 2-methylpropenyl, pentenyl, 2-pentenyl, 2-methylbutenyl, 3-methylbutenyl, 2-methyl-2-butenyl, hexenyl, 2-hexenyl, 3-hexenyl, 2-methylpentenyl, 3-methylpentenyl, 4-methylpentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 2,3-dimethylbutenyl, 2-ethylbutenyl, 3,3-dimethylbutenyl, 2,3-dimethyl-2-butenyl;

C3-C6-alkynyl: propynyl, butynyl, 2-butynyl, pentynyl, 2-pentynyl, 10 3-methylbutynyl, hexynyl, 2-hexynyl,3-hexynyl, 3-methylpentynyl, 4-methylpentynyl, 4-methyl-2-pentynyl;

C3-Cl2-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl, particularly preferably cyclopropyl, cyclopentyl and cyclohexyl;

Cl-C4-alkoxy: methoxy, ethoxy, propoxy, l-methylethoxy, butoxy, 2-butoxy, l-methylpropoxy, 2-methylpropoxy, l,l-dimethylethoxy, 20 in particular methoxy, ethoxy, l-methylethoxy;

Cl-C6-alkoxy: Cl-C4-alkoxy and also pentoxy, 2-pentoxy, 3-pentoxy, l-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methyl-2-butoxy, 3-methyl-2-butoxy, l,l-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, l-hexoxy, 2-hexoxy, 3-hexoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 2-methyl-2-pentoxy, 3-methyl-2-pentoxy, 4-methyl-2-pentoxy, 2-methyl-3-pentoxy, 3-methyl-3-pentoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 2,3-dimethyl-2-butoxy, 30 3,3-dimethyl-2-butoxy, in particular methoxy, ethoxy, l-methylethoxy;

Cl-C4-haloalkoxy: difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, l-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy and pentafluoroethoxy, 1,1,2,3,3,3-hexafluoropropoxy, heptafluoropropoxy, decafluorobutoxy, 1,1-bis-trifluoromethyl-2,2,2-trifluoroethoxy, preferably 40 difluoromethoxy, trifluoromethoxy and chlorodifluoromethoxy;

Cl-C4-alkylthio: methylthio, ethylthio, propylthio, l-methylethylthio, butylthio, 2-butoxy, l-methylpropylthio, 2-methylpropylthio, l,l-dimethylethylthio, in particular methylthio, ethylthio, l-methylethylthio;

21~i~75~

Cl-C4-alkylamino: methylamino, ethylamino, propylamino, l-methylethylamino, butylamino, 2-butylamino, 1-methylpropylamino, 2-methylpropylamino, l,l-dimethylethylamino, in particular methylamino, ethylamino, l-methylethylamino;

di-C1-C4-alkylamino: dimethylamino, n-methyl-n-ethylamino, diethylamino, n-methyl-n-propylamino, n-ethyl-n-propylamino, dipropylamino, diisopropylamino, n-isopropyl-n-methylamino, n-ethyl-n-isopropylamino, n-isopropyl-n-propylamino, 10 dibutylamino, di-2-methylpropylamino, di-l-methylpropylamino, n-butyl-n-methylamino and also isomers, n-butyl-n-ethylamino and also isomers, n-butyl-n-propylamino and also isomer~;

Cl-C6-alkylcarbonyl: acetyl, propionyl, l-propylcarbonyl, 2-propylcarbonyl, 1-butylcarbonyl, 2-butylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, l-pentylcarbonyl, 2-pentylcarbonyl, 3-pentylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2-methyl-2-butylcarbonyl, 3-methyl-2-butylcarbonyl, 20 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-hexylcarbonyl, 2-hexylcarbonyl, 3-hexylcarbonyl, 2-methylpentylcarbonyl, 3-methyl-pentylcarbonyl, 4-methylpentylcarbonyl, 2-methyl-2-pentylcarbonyl, 3-methyl-2-pentylcarbonyl, 4-methyl-2-pentylcarbonyl, 2-methyl-3-pentylcarbonyl, 3-methyl-3-pentylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 3,3-dimethyl-2-butylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, in particular acetyl, propionyl, 30 propylcarbonyl, 2-propylcarbonyl, butylcarbonyl, 2-butylcarbonyl, 1,1-dimethylpropionyl, pentylcarbonyl, 2,2-dimethylpropylcarbonyl, hexylcarbonyl;

Cl-C6-alkoxycarbonyl: acetoxycarbonyl, propoxycarbonyl, 1-propoxycarbonyl, 2-propoxycarbonyl, 1-butoxycarbonyl, 2-butoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, 1-pentoxycarbonyl, 2-pentoxycarbonyl, 3-pentoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2-methyl-2-butoxycarbonyl, 40 3-methyl-2-butoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, l-hexoxycarbonyl, 2-hexoxycarbonyl, 3-hexoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 2-methyl-2-pentoxycarbonyl, 3-methyl-2-pentoxycarbonyl, 4-methyl-2-pentoxycarbonyl, 2-methyl-3-pentoxycarbonyl, 3-methyl-3-pentoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 21~67~4 3,3-dimethylbutoxycarbonyl, 3,3-dimethyl-2-butoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-Trimethylpropoxycarbonyl, in particular acetoxycarbonyl, propoxycarbononyl, 2-propoxycarbonyl, butoxycarbonyl, 2-butoxycarbonyl, l,1-dimethylpropionyl, pentoxycarbonyl, 2,2-dimethylpropoxycarbonyl, hexoxycarbonyl;

Cl-C12-alkoxyimino: methoxyimino, ethoxyimino, propoxyimino, 2-propoxyimino, butoxyimino, l,l-dimethylethoxyimino, 10 pentoxyimino, hexoxyimino, heptyloxyimino, octyloxyimino, nonyloxyimino, decyloxyimino, undecyloxyimino, dodecyloxyimino, in particular methoxyimino and ethoxyimino;

C3-Cl2-alkenyloxyimino: propenyloxyimino, 2-propenyloxyimino, butenyloxyimino, pentenyloxyimino, hexenyloxyimino, heptenyloxyimino, octenyloxyiminoj nonenyloxyimino, decenyloxyimino, undecenyloxyimino, dodecenyloxyimino, in particular 2-propenyloxyimino;

20 C3-C6-haloalkenyloxyimino: 2,3,3-trifluoro-2-propenyloxyimino, 2,3,3-trichloro-2-propenyl- oxyimino, pentafluoro-2-propenyloxyi-mino, pentachloro-2- propenyloxyimino;

C3-Cl2-alkylene chain: propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, in particular butylene, pentylene;
5-membered heteroaromatics which may be mentioned are especially the following heterocycles: 2-thienyl, 3-thienyl, 2-furyl, 30 3-furyl, l-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, l-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, l-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, (lh)1,2,4-triazol-1-yl, (lh)1,2,4-triazol-3-yl, (lh)1,2,4-triazol-5-yl, (4h)1,2,4-triazol-2(5)-yl, (4h)1,2,4-triazol-4-yl, l-tetrazolyl, 5-tetrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 40 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 3(4)-furazanyl, 1,3,4-oxadiazol-2(5)-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

- 216675~
6-membered heteroaromatics which may be mentioned are especially the following heterocycles: 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4(6)-pyrimidinyl, 5-pyrimidinyl, 3(6)-pyrazinyl, 4(5)-pyrazinylt 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,4,5-tetrazin-3(6)-yl.

Benzo-fused 5- or 6-membered ring aromatics are especially:
benzofuranyl, benzothienyl, indolyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzisothiazolyl, benzpyrazolyl, 10 indazolyl, 1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, benzotriazolyl, benzofuroxanyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl or benzoxazinyl.

The compounds of the formula I according to the invention are obtained by reacting a derivative of the formula A-XH
20 where the symbols A and X have the meaning indicated above, in the presence of a base with a pyrimidine of the formula II

Rl7' ~ X z (II) 30 where the symbols Y and Z have the meanings indicated above and where Rl7 is a nucleofugic leaving group such as halogen, prefer-ably chlorine or bromine, alkylsulfonyl, preferably methylsulfo-nyl, phenylsulfonyl or substituted phenylsulfonyl, preferably 4-methylphenylsulfonyl, or another equivalent leaving group.
Bases which can be used are alkali metal or alkaline earth metal hydrides such as NaH or CaH2, alkali metal hydroxides such as NaOH
or KOH, alkali metal alkoxides such as potassium tert-butoxide, alkali metal carbonates such as sodium carbonate or potassium carbonate, alkali metal amides such as sodium amide, lithium 40 diisopropylamide or lithium tetramethylpiperidide or tertiary amines. When using an inorganic base, a phase-transfer catalyst can be added if this promotes the conversion. The solvents used are especially protic or aprotic polar solvents such as, for ex-ample, lower alcohols, tetraalkyl-substituted cyclic or acyclic ureas, dimethylformamide or dimethyl sulfoxide.

216~7~4 Compounds of the formula I can also be prepared by starting from the corresponding carboxylic acids, i.e. compounds of the formula I where W is oxygen and Rl is hydroxyl, and first converting these in a customary manner to an activated form such as a halide or imidazolide and then reacting this with an appropriate nucleo-phile. These two steps can also be simplified, for example, by allowing the carboxylic acid to act on the nucleophile in the presence of a dehydrating agent, such as carbodiimide.

10 Compounds of the formula II can be prepared starting from 2-fluo-romalonic acid esters, 2-fluorocyanoacetic esters, 2-fluoromalo-nonitrile or 1,3-dicarbonyl compounds of the formulae III and IV
F F

(III) ~ OR (IV) O o O O

20 by methods known from the literature (eg. A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon Press 1984; EP 582288).

The compounds I and their agriculturally utilizable salts are suitable, both as isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions containing I
control vegetation on noncultivated areas very well, particularly at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against broad-leaved weeds and 30 grass weeds without noticeably damaging the crop plants. This ef-fect occurs especially at lower application rates.

Taking into account the versatility of the application method, the compounds I or compositions containing them can additionally be employed in a further number of crop plants for the elimin-ation of undesired plants. The following crops, for example, are suitables Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp.
40 rapa, Brassica napus var. napus, Brassica napus var.
napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citr-us limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus `- 21 6~75ll lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N.
rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare)~ Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia 10 faba, Vitis vinifera, Zea mays.

Moreover, the compounds I can also be used in crops which are tolerant to the action of herbicides as a result of breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre-emergence or post-emergence. If the active compounds are less tolerable for certain crop plants, application techniques can be used in which the herbicidal compositions are 20 sprayed with the aid of the spray equipment such that the leaves of the sensitive crop plants are not affected if possible, while the active compounds reach the leaves of undesired plants growing underneath or the uncovered soil surface tpost-directed, lay-by).

The compounds I or the herbicidal compositions containing them can be applied by spraying, atomizing, dusting, broadcasting or watering, for example in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions, or dispersions, emulsions, oil 30 dispersions, pastes, dusting compositions, broadcasting compositions or granules. The application forms depend on the intended uses; in each case they should if possible guarantee the finest dispersion of the active compounds according to the invention.

Suitable inert additives are mineral oil fractions of medium to high boiling point~, such as kerosene or diesel oil, further coal tar oils and also oils of vegetable or ~ni~l origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin, 40 tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone or strongly polar solvents, such as N-methylpyrrolidone or water.

Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by addition of water. To prepare - ~166754 emulsions, pastes or oil dispersions, the substrates can be homogenized in water as such, or dissolved in an oil or solvent, by means of wetting agents, adherents, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, adherent, dispersant or emulsifier and, possibly, solvent or oil can also be prepared, which are suitable for dilution with water.

Suitable surface-active substances (adjuvants) are the alkali 10 metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, napthalene- and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylaryl-sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols as well a~ of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenyl ethers, ethoxylated 20 isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powdered, broadcasting and dusting compositions can be prepared by mixing or joint grinding of the active substances with a solid carrier.
Granules, eg. coated, impregnated and homogeneous granules, can be prepared by binding of the active compounds to solid carriers.
Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic substances, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as grain flower, tree bark, wood and nut shell meal, cellulose powder or 40 other solid carriers.

The concentrations of the active compounds I in the ready-to-apply preparations can be varied within wide ranges. The formulations in general contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of active compound. The - 2i~67~

active compounds are in this case employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

I 20 parts by weight of the compound No.I.001 are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of cal-cium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. ~y pouring out the solution and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

II 20 parts by weight of the compound No.I.124 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 40 mol of isooctyl-phenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pour-ing the ~olution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound.

30 III 20 parts by weight of the active compound No. I.059 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280 C and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By pouring the solution into and finely dispersing it in 100,000 parts by weight of water, an aqueous dispersion is obtained which con-tains 0.02 % by weight of the active compound.

40 IV 20 parts by weight of the active compound No. I.001 are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of - the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray 2~ 667~4 mixture is obtained which contains 0.1 % by weight of the active compound.

V 3 parts by weight of the active compound No. I.124 are mixed with 97 parts by weight of finely divided kaolin.
In this way a dusting composition is obtained which con-tains 3% by weight of the active compound.

VI 20 parts by weight of the active compound No. I.059 are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

VII 1 part by weight of the compound I.001 is dissolved in a mixture which consists of 70 parts by weight of cyclo-hexanone, 20 parts by weight of ethoxylated isooctylphe-nol and 10 parts by weight of ethoxylated ca~tor oil. A
stable emulsion concentrate is obtained.

VIII 1 part by weight of the compound I.124 is dissolved in a mixture which consists of 80 parts by weight of cyclo-hexanone and 20 parts by weight of Emulphor EL. A stable emulsion concentrate is obtained.

To broaden the spectrum of action and to obtain synergistic effects, the fluorinated pyrimidines I can be mixed with numerous 30 representatives of other herbicidal or growth-regulating active compound groups and applied jointly. For example, suitable mixture components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylic acids, triazines, amide~, ureas, diphenyl ethers,-triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives which, for example, carry a carboxyl or carbimino group in the 2-position, quinolinecar-boxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy- or heteroaryloxyphenoxypropionic acids 40 and their salts, esters and amides and others.

Additionally, it can be of use to apply the compounds I on their own or jointly, in combination with other herbicides, additionally mixed with further crop protection compositions, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Further of interest is the miscibility of mineral salt solutions which are employed for the 2 1 ~

elimination of nutritional and trace element deficiencies.
Nonphytotoxic oils and oil concentrates can also be added.

The compounds of the formula I can furthermore affect the various stages of development of a plant and are therefore empIoyed as growth regulators. The diversity of action of the plant growth regulators is especially dependent a) on the plant species and variety, b) on the time of application, based on the stage of development of the plant, and on the time of year, c) on the type and method of application (eg. seed dressing, soil treatment, foliar application or stem injection in the case of trees), d) on climatic factors (eg. temperature, amount of precipita-tion, and additionally also length of day and light inten-sity),e) on the soil condition (including fertilization), f) on the formulation or application form of the active compound and g) on the concentrations of the active substance applied.

A few of the number of various application possibilities of the 30 plant growth regulators of the formula I according to the invention in plant cultivation, in agriculture and in horticulture are mentioned below:

A. The vegetative growth of the plants can be severely inhibited by the compounds which can be used according to the inven-tion, which is manifested, in particular, in a reduction of the longitudinal growth. The treated plants accordingly ex-hibit compact growth; additionally a darker leaf coloration is to be observed.
A decreased intensity of the growth of grasses on roadsides, hedgerows, canal banks and on plots of gras-s such as parks, sp~rts grounds and orchards, ornamental lawns and airfields proves to be advantageous in practice, so that labor- and cost-intensive mowing can be reduced.

- 216~7~4 The increase in the resistance of crops susceptible to lodg-ing, such as cereals, corn, sunflowers and soybeans, is also of economic interest. The culm shortening and culm strengthening caused in this case decrease or eliminate the danger of lodging (of being bent over) of plants under unfa-vorable weather conditions before harvesting.

The application of growth regulators for inhibiting the lon-gitudinal growth and for temporally altering the course of ripening in cotton i8 also important. Completely mechanized harvesting of this important crop plant is thus made pos-sible.

In the case of fruit and other trees, pruning costs can be saved using the growth regulators. In addition, the alterna-tion of fruit trees can be broken by means of growth regula-tors.

The lateral branching of the plants can also be increased or inhibited by application of growth regulators. There is interest in this if, eg. in the case of tobacco plants, the formation of side shoots (suckers) is to be inhibited in favor of leaf growth.

In the case of winter rape, for example, the frost resistance can also be considerably increased using growth regulators.
In this case, on the one hand, the longitudinal growth and the development of an excessively luxuriant (and thereby par-ticularly frost-susceptible) herbage or biomass are inhib-ited. On the other hand, after sowing and before the winterfrosts set in the young rape plants are held back in the vegetative development stage despite favorable growth condi-tions. As a re~ult, the frost danger to those plants which are prone to premature degeneration of the inhibition of flowering and to transition into the generative phase is also eliminated. Even in other crops, eg. winter cereals, it is advantageous if the populations are indeed well tillered by treatment with compounds according to the invention in the fall, but are not too luxuriant when going into the winter.
As a result, the increased frost sensitivity and, because of the relatively low herbage or biomass, attack by various dis-eases (eg. fungal disease) can be prevented. The inhibition of the vegetative growth additionally makes possible a more compact planting of the soil with many crop plants, so that an additional yield can be achieved, based on the soil area.

-- 21667a~i B. Additional yields both of parts of plants and of plant con-stituents can be achieved using the growth regulators. Thus it is possible, for example, to induce the growth of greater amounts of buds, flowers, leaves, fruit, seeds, roots and tu-bers, to increase the content of sugar in sugar beet, sugar cane and citrus fruits, to raise the protein content in cere-als or soybeans or to stimulate rubber trees to an increased flow of latex.

In this case, the compounds of the formula I can cause increases in yield by intervention in the plant metabolism or by promotion or inhibition of vegetative and/or of generative growth.

C. Finally, both reduction or prolongation of the development stages and acceleration or retardation of the ripening of the harvested parts of plants before or after harvesting can be achieved using plant growth regulators.

Of economic interest, for example, is the facilitation of harvesting, which is made possible by the temporally concen-trated fall or decrease in the adhesiveness to the tree in the case of citrus fruits, olives or in the case of other species and varieties of pomes, drupes and indehiscent fruit.
The same mechanism, that is the promotion of the formation of abscission tissue between the fruit or leaf and shoot part of the plant, is also essential for a well-controllable defoli-ation of productive plants such as, for example, cotton.

30 D. The consumption of water by plants can furthermore be reduced using growth regulators. This is particularly important for usable agricultural areas which have to be artificially watered with a high outlay in terms of cost, eg. in arid or semiarid areas. By the use of the substances according to the invention, t-he intensity of watering can be reduced and thus a more cost-effective management can be carried out. Under the influence of growth regulators, a better utilization of the water present occurs because, inter alia, - the opening width of the stomata is reduced, - - a thicker epidermis and cuticle are formed, - the root penetration of the soil is improved and - - the microclimate in the plant population is favorably influenced by a more compact growth.

2166~5~

The compounds I are particularly suitable for culm shortening of crop plants such as barley, rape and wheat.

The growth regulators of the formula I to be used according to the invention can be supplied to the crop plants~both from seeds (as seed-dressing agents) and via the soil, ie. by the roots and, particularly preferably, by spraying over the leaf. The compositions are prepared here in a similar manner to the herbicides (see above).
A~ a result of the high plant compatibility, the application rate of active compound is not critical. The optimum applica-tion rate varies depending on the control target, time of year, target plants and stages of growth.

Depending on the control target, time of year, target plants and stage of growth, the application rates of active compound are from 0.001 to 3.0, preferably from 0.01 to 2.0, kg/ha of active substance (a.s.) Use examples The herbicidal and growth-regulatory action of the fluorinated pyrimidines of the formula I was shown by greenhouse tests:

The cultivation containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as a substrate. The seeds of the test plants were sown separately according to species.
In the case of pre-emergence treatment, the active compounds suspended or emulsified in water were applied directly after sowing by means of finely dispersing nozzles. The containers were lightly watered in order to promote germination and growth, and then covered with transparent plastic hoods until the plants had taken root. This covering causes a uniform germination of the test plants if this has not been adversely affected by the active compoundq.

40 For the purpose of post-emergence treatment, the test plants are first grown, depending on growth form, to a height of growth of from 3 to 15 cm and treated only then with the active compounds suspended or emulsified in water. For this purpose, the test plants are either sown directly and raised in the same containers or they are first grown separately as seedlings and transplanted into the test containers a few days before treatment. The application rate for post-emergence treatment is 0.0625 or 0.0313 kg/ha of a.s.

The plants were kept in a speeies-specific manner at 10-25 C or 20-35 C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their reaction to the individual treatments was assessed.

Assessment was carried out on a scale from 0 to 100. In this 10 case, 100 means no emergence of the plants or complete destruction at least of the above-ground parts and 0 means no damage or normal course of growth.

The plants used in the greenhouse tests were made up of the following species:

Botanical name Common name Alopecurus blackgrass 20 myosuroides Sinapis alba white mustard Solanum nigrum black nightshade Table 1 - Herbicidal activity on post-emergence application in the greenhouse ~ ~ N
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1.078 O-Cyclopropyl O O OMe OMe - 4-Cl 1.079 OCH2-CO2Me O O OMe OMe - 4-Cl 1.080 1 O O OMe OMe - 4-Cl ~,0 1.081 OPh O O OMe OMe - 4-Cl 1.082 O-C6H4-4-NO2 OMe OMe - 4-Cl 1.083 ON-CMe2 - O O OMe OMe - 4-Cl 1.084 ON=CMe2 O S OMe OMe - 4-Cl `- 21667~

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1.170 H N-OH O OMe OMe - 4-Br ~ ~Ca 1.171 H N-OMe O OMe OMe - 4-Br 1.172 H N-OEt O OMe OMe - 4-Br 1.173 H N-OtBu O OMe OMe - 4-Br 1.174 H N-OCH=CH2 O OMe OMe - 4-Br 1.175 H N- O OMe OMe - 4-Br OCH2CH=CH2 1.176 H N-OPh O OMe OMe - 4-Br 1.177 H N-NH2 O OMe OMe - 4-Br 1.178 H N-NHMe O OMe OMe - 4-Br 1.179 H N-NMe2 O OMe OMe - 4-Br No . Rl W X Y Z ( R2 ) n Rn 1.180 H N-NHPh O OMe OMe - 4-Br 1.181 O,H O O OMe OMe - 2-F
1.182 OH O O OMe OMe - 3-F
1.183 OH O O OMe OMe - 4-F
1.184 OH O O OMe OMe - 2,3,4,5,6-Fs 1.185 OH 'O O OMe OMe - 2-Me 1.186 OH O O OMe OMe - 3-He 1.187 OH O O OMe OMe - 4-Me 1.188 OH O O OMe OMe - 2-Et 1.189 OH O O OMe OMe - 3-Et 1.190 OH o o OMe OMe - 4-Et O C~
1.191 OH O O OMe OMe - 2-CMe2 1.192 OH O O OMe OMe - 3-CMe2 1.193 OH O O OMe OMe - 4-CMe2 1.194 OH O O OMe OMe - 2,3-Me2 1.195 OH O O OMe OMe - 2,4-Me2 1.196 OH O O OMe OMe - 2,5-Me2 1.197 OH O O OMe OMe - 2,6-Me2 1.198 OH O O OMe OMe - 3,4-Me2 1.199 OH O O OMe OMe - 3,5-Me2 1.200 OH O O OMe OMe - 2,4,6-Me3 ~16675l~

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1.280 OH O O OMe OMe - ~ o o/
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No. Rl W X Y Z ( R2 ) n Het 2.077 O-K+ O O OMe OMe - 1-Methylpyrrol-3-yl 2.078 O~ l/2Ca2+O O OMe OMe - l-Methylpyrrol-3-yl 2.079 O-(NH4)+ O O OMe OMe - 1-Methylpyrrol-3-yl 2.080 O~(NMe4)+ O O OMe OMe - l-Methylpyrrol-3-yl 2.081 OMe O O OMe OMe - l-Methylpyrrol-3-yl 2.082 OEt 'O O OMe OMe - 1-Methylpyrrol-3-yl 2.083 O-CH2-OMe O O OMe OMe - 1-Methylpyrrol-3-yl 2.084 0-CH2-SMe O O OMe OMe - 1-Methylpyrrol-3-yl 2.085 OCH2CH=CH2 OMe OMe - 1-Methylpyrrol-3-yle~
2.086 OCH2C_CH- O O OMe OMe - 1-Methylpyrrol-3-yl_~
2.087 ~ ~ O O OMe OMe - 1-Methylpyrrol-3-yl~ ~n O N
2.088 O-Cyclopropyl O O OMe OMe - 1-Methylpyrrol-3-yl 2.089 OCH2-CO2He O O OMe OMe - 1-Methylpyrrol-3-yl 2.090 1 O O OMe OMe - 1-Methylpyrrol-3-yl N
2.091 OPh O O OMe OMe - l-Methylpyrrol-3-yl 2.092 o-C6H4-4-NO2 OMe OMe - l-Methylpyrrol-3-yl 2.093 ON=CMe2 O O OMe OMe - 1-Methylpyrrol-3-yl 2.094 ON=CMe2 O S OMe OMe - 1-Methylpyrrol-3-yl No . Rl . W X Y Z ( R2 ) n Het 2.095 O O O OMe OMe - l-Methylpyrrol-3-yl N=O
2.096 ONzCMe-SMe O O OMe OMe - l-Methylpyrrol-3-yl 2.097 O-NMe2 O O OMe OMe - l-Methylpyrrol-3-yl 2.098 O-(l-Piperidyl) O O OMe OMe - 1-Methylpyrrol-3-yl 2.099 0-(4-Morpholinyl) O O OMe OMe - l-Methylpyrrol-3-yl 2.100 o\\ O O OMe OMe - l-Methylpyrrol-3-yl -- N
~ CS;~
2.101 1-Pyrrolyl O O OMe OMe - l-Methylpyrrol-3-yl ~ C~
2.102 l-Pyrazolyl O O OMe OMe - 1-Methylpyrrol-3-yl ~n 2.103 l-Imidazolyl O O OMe OMe - l-Hethylpyrrol-3-yl 2.104 1,2,4-Tria2Ol-l-yl O O OMe OMe - l-Methylpyrrol-3-yl 2.105 NH-SO2Me O O OMe OMe - l-Methylpyrrol-3-yl 2.106 NH-SO2Ph O O OHe OMe - l-Methylpyrrol-3-yl 2.107 NHSO2C6H4-4-Me O O OMe OMe - l-Methylpyrrol-3-yl 2.109 H O O OMe OMe - l-Methylpyrrol-3-yl 2.110 Me O O OMe OMe - 1-Methylpyrrol-3-yl 2.111 H NMe O OMe OMe - l-Methylpyrrol-3-yl 2.112 H NtBu O OMe OMe - l-Methylpyrrol-3-yl 2.113 H NPh O OMe OMe - 1-Methylpyrrol-3-yl No. Rl W X Y Z ( R2 ) n Het2.114 H N-OH O OHe OMe - 1-Hethylpyrrol-3-yl 2.115 H N-OMe O OMe OMe - 1-Methylpyrrol-3-yl 2.116 H N-OEt O OMe OMe - 1-Methylpyrrol-3-yl 2.117 H N-Ot~u O OMe OHe - 1-Methylpyrrol-3-yl 2.118 H N-OCH=CH2 O OMe OMe - 1-Methylpyrrol-3-yl 2.119 H N-OCH2CH=CH2 OMe OMe - 1-Methylpyrrol-3-yl 2.120 H N-OPh O OMe OMe - 1-Methylpyrrol-3-yl 2.121 H N-NH2 O OMe OMe - 1-Methylpyrrol-3-yl 2.122 H N-NHMe O OMe OMe - 1-Methylpyrrol-3-yl 2.123 H N-NMe2 O OMe OMe - 1-Methylpyrrol-3-yl 2.124 H N-NHPh O OMe OMe - 1-Methylpyrrol-3-yl ~ _~
2.125 OH O O OMe OMe - 2-Methylpyrrol-3-yl 2.126 OH O O OMe OMe - 4-Methylpyrrol-3-yl 2.127 OH O O OMe OMe - 5-Methylpyrrol-3-yl 2.128 OH O O OMe OMe - 3,5-Dimethylpyrrol-1-yl 2.129 OH O O OMe OMe - 1,4-Dimethylpyrrol-3-yl 2.130 OH O O OMe OMe - 1,5-Dimethylpyrrol-3-yl 2.131 OH O O OMe OMe - 1,3-Dimethylpyrrol-4-yl 2.132 OH O O OMe OMe - 1,5-Dimethylpyrrol-3-yl 2.133 OH O O OMe OMe - 1,4-Dimethylpyrrol-5-yl 2.134 OH O O OMe OMe - 1,3-Dimethylpyrrol-5-yl ~1667~

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m m m m m m m m m m m m m :1: m m m m m m m oo,ooooooooooooooooooo No . Rl W X Y Z ( R2 ) n Het2.156 OH O O OMe OMe - 3-Methyl-5-phenylpyrrol-1-yl 2.157 pH O O OMe OMe - 3,5-Bistrifluoromethylpyrrol-l-yl 2.lS8 OH O O OMe OMe - 4-Nitropyrrol-1-yl 2.159 OH O O OMe OMe - l-Phenylpyrrol-3-yl 2.160 OH O O OMe OMe - 1,3,5-Trimethylpyrrol-4-yl 2.161 OH O O OMe OMe - 1-Phenylpyrrol-2-yl 2.162 OH O O OMe OMe - l-Phenylpyrrol-3-yl 2.163 OH O O OMe OMe - 5-Methyl-1-phenylpyrrol-3-yl 2.164 OH O O OMe OMe - 3-Methyl-1-phenylpyrrol-4-yl 2.165 OH O O OMe OMe - 5-Methyl-1-phenylpyrrol-2-yl 2.166 OH O O OMe OMe - 3,5-Dimethyl-1-phenylpyrrol-4-yl 2.167 OH O O OMe OMe - 3-Methyl-1-phenylpyrrol-5-yl 2.168 OH O O OMe OMe - 1-Metho~y~ ol-2-yl 2.169 OH O O OMe OMe - 1-Metho~y~yLrol-3-yl 2.170 OH O O OMe OMe - 2-Methoxypyrrol-1-yl 2.171 OH O O OMe OMe - 2-Methoxy-l-methylpyrrol-3-yl 2.172 OH O O OMe OMe - 2-Hethoxy-1-methylpyrrol-4-yl 2.173 OH O O OMe OMe - 2-Methoxy-1-methylpyrrol-5-yl 2.174 OH O O OMe OMe - 3-Metho~y~y~ol-l-yl 2.175 OH O O OMe OMe - 3-Methoxy-1-methylpyrrol-2-yl 2.176 OH O O OMe OMe - 3-Methoxy-1-methylpyrrol-4-yl No . Rl W X Y Z ( R2 ) n Het 2.177 OH O O OMe OMe - 3-Methoxy-1-methylpyrrol-5-yl 2.178 ,OH O O OMe OMe - 2-Difluorometho~y~yLLol-l-yl 2.179 OH O O OMe OMe - 2-Difluoromethoxy-1-methylpyrrol-3-yl 2.180 OH O O OMe OMe - 2-Difluoromethoxy-1-methylpyrrol-4-yl 2.181 OH O O OMe OMe - 2-Difluoromethoxy-1-methylpyrrol-5-yl 2.182 OH ' O O OMe OMe - 3-Difluoromethoxypyrrol-1-yl 2.183 OH O O OMe OMe - 3-Difluoromethoxy-1-methylpyrrol-2-yl ~
2.184 OH O O OHe OMe - 3-Difluoromethoxy-1-methylpyrrol-4-yl ~' 2.185 OH O O OMe OMe - 3-Difluoromethoxy-1-methylpyrrol-5-yl C~
2.186 OH O O OMe OMe - 1-Indolyl ~~
2.187 OH O O OMe OMe - l-Methylindol-2-yl 2.188 OH O O OMe OMe - 1-Methylindol-3-yl 2.189 OH O O OMe OMe - 3-Methylindol-1-yl 2.190 OH O O OMe OMe - 2-Thienyl 2.191 H O O OMe OMe - 2-Thienyl 2.192 OH O NH OMe OMe - 2-Thienyl 2.193 OH O N-CN OMe OMe - 2-Thienyl 2.194 OH N-OH O OMe OMe - 2-Thienyl 2.195 OH N-OMe O OMe OMe - 2-Thienyl 2.196 OH O O OMe OMe 5-Me 2-Thienyl 2.197 O~Na+ O O OMe OMe - 2-Thienyl No. Rl . W X Y Z ( R2 ) n Het 2.198 O-K+ O O OMe OMe - 2-Thienyl 2.199 p~ 1/2Ca2+ O O OMe OMe - 2-Thienyl 2.200 O-~NH4)+ O O OMe OMe - 2-Thienyl 2.201 O~~ We4)+ O O OMe OHe - 2-Thienyl 2.202 OMe O O OMe OMe - 2-Thienyl 2.203 OEt O O OMe OMe - 2-Thienyl 2.204 O-CH2-OMe O O OMe OMe - 2-Thienyl 2.205 O-CH2-SMe O O OMe OMe - 2-Thienyl 2.206 0CH2CH=CH2 OMe OMe - 2-Thienyl e~
2.207 OCH2C_CH O O OMe OMe - 2-Thienyl C~
2.208 ~ ~ o o OMe OMe - 2-Thienyl ~ cn O N
2.209 O-Cyclopropyl O O OMe OMe - 2-Thienyl 2.210 OCH2-CO2Me O O OMe OMe - 2-Thienyl 2.211 1 O O OMe OMe - 2-Thienyl 0 ~,0 2.212 OPh O O OMe OMe - 2-Thienyl 2.213 o-C6H4-4-NO2 OMe OMe - 2-Thienyl 2.214 ON=CMe2 O O OMe OMe - 2-Thienyl 2.215 ON=CMe2 O S OMe OMe - 2-Thienyl 216 ~ 7 ~ 4 -c c c c c c c c c c c c c r c c c c a a a, a, a a a a a, a a a a a a a a a r .~ .r r ~ ~ r r r r r r r r r r ~
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No . Rl W X Y Z ~ R2 ) n Het 2.234 H N-OH O OMe OMe - 2-Thienyl 2.235 H N-OMe O OMe OMe - 2-Thienyl 2.236 H N-OEt O OMe OMe - 2-Thienyl 2.237 H N-OtBu O OMe OMe - 2-Thienyl 2.238 H N-OCH=CH2 O OMe OMe - 2-Thienyl 2.239 H N-OCH2CH=CH2 OMe OMe - 2-Thienyl 2.240 H N-OPh O OHe OMe - 2-Thienyl 2.241 H N-NH2 O OMe OMe - 2-Thienyl 2.242 H N-NHMe O OMe OMe - 2-Thienyl 2.243 H N-NMe2 0 OMe OMe - 2-Thienyl 2.244 H N-NHPh O OMe OMe - 2-Tkienyl o C~
2.245 OH O O OMe OMe - 3-Thienyl 2.246 H O O OMe OMe - 3-Thienyl 2.247 OH O NH OMe OMe - 3-Thienyl 2.248 OH O N-CN OMe OMe - 3-Thienyl 2.249 OH N-OH O OMe OMe - 3-Thienyl 2.250 OH N-OMe O OMe OMe - 3-Thienyl 2.251 OH O O OMe OMe 5-Me 3-Thienyl 2.252 O~Na+ O O OMe OMe - 3-Thienyl 2.253 O-K+ O O OMe OMe - 3-Thienyl 2.254 O~ 1/2Ca2+ O O OHe OMe - 3-Thienyl ` ` 21667~1 .

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No . Rl W X Y Z ( R2 ) n Het 2.291 H N-OEt O OMe OMe - 3-Thienyl 2.292 H N-OtBu O OMe OMe - 3-Thienyl 2.293 H N-OCH=CH2 O OMe OMe - 3-Thienyl 2.294 H N-OCH2CH=CH2 OMe OMe - 3-Thienyl 2.295 H N-OPh O OMe OMe - 3-Thienyl 2.296 H N-NH2 O OMe OMe - 3-Thienyl 2.297 H N-NHMe O OMe OMe - 3-Thienyl 2.298 H N-NMe2 0 OMe OMe - 3-Thienyl CS~
2.299 H N-NHPh O OMe OMe - 3-Thienyl 2.300 OH O O OMe OMe - 3-Methyl-2-thienylw ~.
2.301 OH O O OMe OMe - 4-Methyl-2-thienyl 2.302 OH O O OMe OMe - 5-Methyl-2-thienyl 2.303 OH O O OMe OMe - 2-Methyl-3-thienyl 2.304 OH O O OMe OMe - 4-Methyl-3-thienyl 2.305 OH O O OMe OMe - 5-Methyl-3-thienyl 2.306 OH O O OMe OMe - 4,5-Dimethyl-3-thienyl 2.307 OH O O OMe OMe - 4,5-Dimethyl-2-thienyl 2.308 OH O O OMe OMe - 4-Chloro-5-thienyl 2.309 OH O O OMe OMe - 3-Chloro-5-thienyl 2.310 OH O O OMe OMe - 2-Chloro-5-thienyl ~1667~4 C~ C~
~SL~CCCCCC~
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No . Rl W X Y Z ( R2 ) n Het 2.332 OH O O OMe OMe - 5-Ethoxy-4-thienyl 2.333 ,OH O O OMe OMe - 3-Ethoxy-4-thienyl 2.334 OH O O OMe OMe - 2-Ethoxy-4-thienyl 2.335 OH O O OMe OMe - 4-Difluoromethoxy-5-thienyl 2.336 OH O O OMe OMe - 3-Difluoromethoxy-5-thienyl 2.337 OH O O OMe OMe - 2-Difluoromethoxy-5-thienyl 2.338 OH O O OMe OMe - 5-Difluoromethoxy-4-thienyl 2.339 OH O O OMe OMe - 3-Difluoromethoxy-4-thienyl 2.340 OH O O OMe OMe - 2-Difluoromethoxy-4-thienyl 2.341 OH O O OMe OMe - 4-Methylthio-5-thienyl 2.342 OH O O OMe OMe - 3-Methylthio-5-thienyl 2.343 OH O O OMe OMe - 2-Methylthio-5-thienyl 2.344 OH O O OMe OMe - 5-Methylthio-4-thienyl 2.345 OH O O OMe OMe - 3-Methylthio-4-thienyl 2.346 OH O O OMe OMe - 2-Methylthio-4-thienyl 2.347 OH O O OMe OMe - 4-Dimethylamino-5-thienyl 2.348 OH O O OMe OMe - 3-Dimethylamino-5-thienyl 2.349 OH O O OMe OMe - 2-Dimethylamino-5-thienyl 2.350 OH O O OMe OMe - 5-Dimethylamino-4-thienyl 2.351 OH O O OMe OMe - 3-Dimethylamino-4-thienyl 2.352 OH o O OMe OMe - 2-Dimethylamino-4-thienyl 2:~6754 ,. ..

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o No ~ Rl W X Y Z ( R2 ) n Het 2.374 OH O O OMe OMe - 2-Chloro-4-furyl 2.375 OH O O OMe OMe - 4-Bromo-5-furyl 2.376 OH O O OMe OMe - 3-Bromo-5-furyl 2.377 OH O O OMe OMe - 2-Bromo-5-furyl 2.378 OH O O OMe OMe - 5-Bromo-4-furyl 2.379 OH O O OMe OMe - 3-Bromo-4-furyl 2.380 OH O O OMe OMe - 2-Bromo-4-furyl 2.381 OH O O OMe OMe - 2,3-Dichloro-4-furyl 2.382 OH O O OMe OMe - 2,5-Dichloro-3-furyl 2.383 OH O O OMe OMe - 2-Nitro-5-furyl 2.384 OH O O OMe OMe - 4-Methoxy-5-furyl ~ C~2.385 OH O O OMe OMe - 3-Methoxy-5-furyl e 2.386 OH O O OMe OMe - 2-Methoxy-5-furyl 2.387 OH O O OMe OMe - 5-Methoxy-4-furyl 2.388 OH O O OMe OMe - 3-Methoxy-4-furyl 2.389 OH O O OMe OMe - 2-Methoxy-4-furyl 2.390 OH O O OMe OMe - 4-Ethoxy-5-furyl 2.391 OH O O OMe OMe - 3-Ethoxy-5-furyl 2.392 OH O O OMe OMe - 2-Ethoxy-5-furyl 2.393 OH O O OMe OMe - 5-Ethoxy-4-furyl 2.394 OH O O OMe OMe - 3-Ethoxy-4-furyl No . Rl W X Y Z ( R2 ) n Het 2.395 OH O O OMe OMe - 2-Ethoxy-4-furyl 2.396 OH O O OMe OMe - 4-Difluoromethoxy-S-furyl 2.397 OH O O OMe OMe - 3-Difluoromethoxy-5-furyl 2.398 OH O O OMe OMe - 2-Dif}uoromethoxy-5-furyl 2.399 OH O O OMe OMe - 5-Difluoromethoxy-4-furyl 2.400 OH ~O O OMe OMe - 3-Difluoromethoxy-4-furyl 2.401 OH O O OMe OMe - 2-Difluoromethoxy-4-furyl 2.402 OH O O OMe OMe - 4-Methylthio-5-furyl 2.403 OH O O OMe OMe - 3-Methylthio-5-furyl ~' 2.404 OH O O OMe OMe - 2-Methylthio-5-furyl 2.405 OH O O OMe OMe - 5-Methylthio-4-furyl ~ G
2.406 OH O O OMe OMe - 3-Methylthio-4-furyl 2.407 OH O O OMe OMe - 2-Methylthio-4-furyl 2.408 OH O o OMe OMe - 4-Dimethylamino-5-furyl 2.409 OH O O OMe OMe - 3-Dimethylamino-5-furyl 2.410 OH O O OMe OMe - 2-Dimethylamino-5-furyl 2.411 OH O O OMe OMe - 5-Dimethylamino-4-furyl 2.412 OH O O OMe OMe - 3-Dimethylamino-4-furyl 2.413 OH O O OMe OMe - 2-Dimethylamino-4-furyl 2.414 OH O O OMe OMe - Benzofur-2-yl 2.415 OH O S OMe OMe - Benzofur-2-yl No . Rl W X Y Z ( R2 ) n Het 2.416 OH O O OMe OMe - Benzofur-3-yl 2.417 ,H O O OMe OMe - Benzofur-3-yl 2.418 OH O S OMe OMe - Benzofur-3-yl 2.419 OH O O OMe OMe - l-Pyrazolyl 2.420 H O O OMe OMe - l-Pyrazolyl 2.421 OH O O OMe OMe - l-Methylpyrazol-3-yl 2.422 OH O S OMe OMe - l-Methylpyrazol-3-yl 2.423 OH O O OMe OMe - l-Methylpyrazol-4-yl 2.424 OH O S OMe OMe - l-Methylpyrazol-4-yl 2.425 OH O NH OMe OMe - l-Methylpyrazol-4-yl C5 2.426 OH O N-CN OMe OMe - l-Methylpyrazol-4-yl ~ c~
2.427 OH N-OH O OMe OMe - l-Methylpyrazol-4-yl 2.428 OH N-OMe O OMe OMe - l-Methylpyrazol-4-yl 2.429 OH O O OMe OMe 5-Me l-Methylpyrazol-4-yl 2.430 O~Na+ O O OMe OMe - l-Methylpyrazol-4-yl 2.431 O-K+ O O OMe OMe - l-Methylpyrazol-4-yl 2.432 O~ l/2Ca2+ O O OMe OMe - l-Methylpyrazol-4-yl 2.433 O-(NH4)+ O O OMe OMe - l-Methylpyrazol-4-yl 2.434 O~(NMe4)+ O O OMe OMe - l-Methylpyrazol-4-yl 2.435 OMe O O OMe OMe - l-Methylpyrazol-4-yl 2.436 OEt O O OMe OMe - 1-Methylpyrazol-4-yl No . Rl W X Y Z ( R2 ) n Het 2.437 O-CH2-OMe O O OMe OMe - l-Methylpyrazol-4-yl 2.438 ~-CH2-SMe O O OMe OMe - l-Methylpyrazol-4-yl 2.439 OCH2CH=CH2 OMe OMe - 1-Methylpyrazol-4-yl 2.440 OCH2C-CH O O OMe OMe - l-Hethylpyrazol-4-yl 2.441 ~ ~ O O OMe OMe - l-Methylpyrazol-4-yl O N
2.442 O-Cyclopropyl O O OMe OMe - l-Methylpyrazol-4-yl 2.443 OCH2-CO2Me o o OMe OMe - l-Methylpyrazol-4-yl 2.444 1 0 0 OMe OMe - l-Methylpyrazol-4-yl o~,o N
2.445 OPh O O OMe OMe - 1-Methylpyrazol-4-yl 2.446 O-C6H4-4-NO2 OMe OMe - 1-Methylpyrazol-4-yl 2.447 ON=CMe2 0 0 OMe OMe - l-Hethylpyrazol-4-yl 2.448 ON=CMe2 0 S OMe OMe - l-Methylpyrazol-4-yl 2.449 0 0 0 OMe OMe - l-Methylpyrazol-4-yl N=O
2.450 ON=CMe-SMe O O OMe OMe - 1-Methylpyrazol-4-yl 2.451 O-NMe2 0 0 OMe OMe - l-Methylpyrazol-4-yl 2.452 O-(l-Piperidyl) O O OMe OMe - l-Methylpyrazol-4-yl 2.453 0-(4-Morpholinyl) O O OMe OMe - l-Methylpyrazol-4-yl No Rl W X Y Z ( R2 ) n Het 2.454 ~ O O OMe OMe - 1-Methylpyrazol-4-yl , -- N~
//

2.455 1-Pyrrolyl O O OMe OMe - l-Methylpyrazol-4-yl 2.456 1-Pyrazolyl O O OMe OMe - 1-Methylpyrazol-4-yl 2.457 1-Imidazolyl O O OMe OMe - 1-Methylpyrazol-4-yl 2.458 1,2,4-Triazol-l-yl O O OMe OMe - l-Methylpyrazol-4-yl 2.459 NH-S02Me O O OMe OMe - 1-Hethylpyrazol-4-yl 2.460 NH-SO2Ph O O OMe OMe - 1-Methylpyrazol-4-yl C~
2.461 NHSO2C6H4-4-Me O O OHe OMe - l-Methylpyrazol-4-yl C~
2.462 H O O OMe OHe - 1-Methylpyrazol-4-yl 2.463 Me O O OHe OMe - l-Methylpyrazol-4-yl 2.464 H NMe O OMe OMe - 1-Methylpyrazol-4-yl 2.465 H NtBu O OMe OMe - 1-Methylpyrazol-4-yl 2.466 H NPh O OMe OMe - 1-Methylpyrazol-4-yl 2.467 H N-OH O OMe OMe - 1-Methylpyrazol-4-yl 2.468 H N-OMe O OMe OMe - 1-Methylpyrazol-4-yl 2.469 H N-OEt O OMe OMe - l-Methylpyrazol-4-yl 2.470 H N-OtBu O OMe OMe - l-Methylpyrazol-4-yl 2.471 H N-OCH=CH2 O OMe OMe - 1-Methylpyrazol-4-yl 2.472 H N-OCH2CH=CH2 OMe OMe - 1-Methylpyrazol-4-yl No . Rl W X Y Z ( R2 ) n Het 2.473 H N-OPh O OHe OMe - 1-Methylpyrazol-4-yl 2.474 ,H N-NH2 O OMe OMe - l-Methylpyrazol-4-yl 2.475 H N-NHMe O OMe OMe - l-Methylpyrazol-4-yl 2.476 H N-NMe2 O OMe OMe - l-Methylpyrazol-4-yl 2.477 H N-NHPh O OMe OMe - l-Methylpyrazol-4-yl 2.478 OH O O OMe OMe - 1-Methylpyrazol-5-yl 2.479 OH O S OMe OMe - l-Methylpyrazol-5-yl 2.480 OH O O OMe OMe - 3-Methylpyrazol-l-yl 2.481 OH O O OMe OMe - 4-Methylpyrazol-l-yl 2.482 OH O O OMe OMe - 5-Methylpyrazol-l-yl 2.483 OH O O OMe OMe - 1,4-Dimethylpyrazol-3-yl 2.484 OH O O OMe OMe - 1,S-Dimethylpyrazol-3-yl 2.485 OH O O OMe OMe - 1,3-Dimethylpyrazol-4-yl 2.486 OH O O OMe OMe - 1,S-Dimethylpyrazol-4-yl 2.487 OH O O OMe OMe - 1,3-Dimethylpyrazol-S-yl 2.488 OH O O OMe OMe - 1,4-Dimethylpyrazol-S-yl 2.489 OH O O OMe OMe - 3,4,5-Trimethylpyrazol-l-yl 2.490 OH O O OMe OMe - 1,4,5-Trimethylpyrazol-3-yl 2.491 OH O O OMe OMe - 1,3,5-Trimethylpyrazol-4-yl 2.492 OH O o OMe OMe - 1,3,4-Trimethylpyrazol-5-yl 2.493 OH O O OMe OMe - l-Methoxypyrazol-3-yl No. Rl W . X Y Z ( R2 ) n Het 2.494 OH O S OMe OMe - l-Methoxypyrazol-3-yl 2.495 ,OH O O OMe OMe - 1-Methoxypyrazol-4-yl 2.496 OH O S OMe OMe - l-Methoxypyrazol-4-yl 2.497 OH O O OMe OMe - l-Methoxypyrazol-5-yl 2.498 OH O S OMe OMe - 1-Methoxypyrazol-5-yl 2.499 OH O O OMe OMe - l-Methyl-4-methoxypyrazol-3-yl 2.500 OH O S OMe OMe - l-Methyl-4-methoxypyrazol-3-yl 2.501 OH O O OMe OMe - l-Methyl-4-methoxypyrazol-5-yl ~a 2.502 OH O S OMe OMe - l-Methyl-4-methoxypyrazol-5-yl 2.503 OH O O OMe OMe - l-Methyl-3-methoxypyrazol-4-yl 2.504 OH O S OMe OMe - l-Methyl-3-methoxypyrazol-4-yl 2.505 OH O O OMe OMe - 1-Methyl-3-methoxypyrazol-5-yl 2.506 OH O S OMe OMe - l-Methyl-3-methoxypyrazol-5-yl 2.507 OH O O OMe OMe - l-Hethyl-5-methoxypyrazol-3-yl 2.508 OH O S OMe OMe - l-Methyl-5-methoxypyrazol-3-yl 2.509 OH O O OMe OMe - 1-Methyl-5-methoxypyrazol-4-yl 2.510 OH O S OMe OMe - 1-Methyl-5-methoxypyrazol-4-yl 2.511 OH O O OMe OMe - l-Ethoxypyrazol-3-yl 2.512 OH O S OMe OMe - l-Ethoxypyrazol-3-yl 2.513 OH O O OMe OMe - l-Ethoxypyrazol-4-yl 2.514 OH o S OMe OMe - l-Ethoxypyrazol-4-yl No. Rl W X y Z (R2 )n Het 2.515 OH O O OMe OMe - l-Ethoxypyrazol-S-yl 2.516 ,OH O S OMe OMe - 1-Ethoxypyrazol-5-yl 2.517 OH O O OMe OMe - l-Isopropoxypyrazol-3-yl 2.518 OH O S OMe OMe - l-Isopropoxy~y~azol-3-yl 2.519 OH O O OMe OMe - l-Isopropoxypyrazol-4-yl 2.520 OH 'O S OMe OMe - l-Isopropoxypyrazol-4-yl 2.521 OH O O OMe OMe - l-Isopropoxypyrazol-S-yl 2.522 OH O S OMe OMe - l-Isopropoxypyrazol-5-yl 2.523 OH O O OHe OMe - l-Methyl-4-difluoromethoxypyrazol-3-yl 2.524 OH O S OMe OMe - l-Methyl-4-difluoromethoxypyrazol-3-yl 2.525 OH O O OHe OMe - l-Methyl-4-difluoromethoxypyrazol-5-yl 2.526 OH O S OMe OMe - l-Methyl-4-difluoromethoxypyrazol-5-yl 2.527 OH O O OMe OMe - l-Methyl-3-difluoromethoxypyrazol-4-yl 2.528 OH O S OMe OMe - l-Methyl-3-difluoromethoxypyrazol-4-yl 2.529 OH O O OMe OMe - l-Methyl-3-difluoromethoxypyrazol-5-yl 2.530 OH O S OMe OMe - l-Methyl-3-difluoromethoxypyrazol-5-yl 2.531 OH O O OMe OMe - l-Methyl-5-difluoromethoxypyrazol-3-yl 2.532 OH O S OMe OMe - l-Methyl-5-difluoromethoxypyrazol-3-yl 2.533 OH O O OMe OMe - l-Methyl-5-difluoromethoxypyrazol-4-yl 2.534 OH O S OMe OMe - l-Methyl-5-difluoromethoxypyrazol-4-yl 2.535 OH o O OMe OMe - l-Methyl-4-methylthiopyrazol-3-yl No . Rl W X Y Z ( R2 ) n Het 2.536 OH O S OMe OMe - l-Methyl-4-methylthiopyrazol-3-yl 2.537 ~H O O OMe OMe - l-Methyl-4-methylthiopyrazol-5-yl 2.538 OH O S OMe OMe - l-Methyl-4-methylthiopyrazol-5-yl 2.539 OH O O OMe OMe - l-Hethyl-3-methylthiopyrazol-4-yl 2.540 OH O S OMe OMe - 1-Methyl-3-methylthiopyrazol-4-yl 2.541 OH 'O O OMe OMe - l-Methyl-3-methylthiopyrazol-5-yl 2.542 OH O S OMe OMe - l-Methyl-3-methylthiopyrazol-5-yl 2.543 OH O O OMe OMe - l-Methyl-5-methylthiopyrazol-3-yl 2.544 OH O S OMe OMe - l-Methyl-5-methylthiopyrazol-3-yl 2.545 OH O O OMe OMe - l-Methyl-5-methylthiopyrazol-4-yl 2.546 OH O S OMe OMe - 1-Methyl-5-methylthiopyrazol-4-yl ~ _~
2.547 OH O O OMe OMe - 3,5-Dimethylpyrazol-l-yl 2.548 OH O O OMe OHe - 4-Chloropyrazol-l-yl 2.549 OH O O OMe OMe - 4-Bromopyrazol-l-yl 2.550 OH O O OMe OMe - 4-Phenylpyrazol-1-yl 2.551 OH O O OHe OMe - 3,4,5-Trimethylpyrazol-1-yl 2.552 OH O O OMe OMe - 4-Chloro-3,5-dimethylpyrazol-1-yl 2.553 OH O O OMe OMe - 4-Isopropylpyrazol-l-yl 2.554 OH O O OMe OMe - 3(5)-Phenylpyrazol-l-yl 2.555 OH O O OMe OMe - 3(5)-Methyl-5(3)-phenylpyrazol-1-yl 2.556 OH O O OMe OMe - 3,5-Bistrifluoromethylpyrazol-l-yl No . Rl W X Y Z ( R2 ) n Het 2.557 OH O O OMe OMe - 4-Nitropyrazol-l-yl 2.558 pH O O OHe OMe - l-Phenylpyrazol-4-yl 2.559 OH O O OMe OMe - 1,3,5-Trimethylpyrazol-4-yl 2.560 OH O O OMe OMe - l-Phenylpyrazol-5-yl 2.561 OH O O OMe OMe - l-Phenylpyrazol-3-yl 2.562 OH O O OMe OMe - 1,4-Dimethylpyrazol-3-yl 2.563 OH O O OMe OMe - 5-Methyl-l-phenylpyrazol-3-yl 2.564 OH O O OMe OMe - 1,5-Dimethylpyrazol-3-yl 2.565 OH O O OMe OMe - 1,3-Dimethylpyrazol-4-yl 2.566 OH O O OMe OMe - 1,5-Dimethylpyrazol-4-yl 2.567 OH O O OMe OMe - 3-Methyl-l-phenylpyrazol-4-yl 2.568 OH O O OMe OMe - 5-Methyl-l-phenylpyrazol-4-yl 2.569 OH O O OMe OMe - 3,5-Dimethyl-l-phenylpyrazol-4-yl 2.570 OH O O OMe OMe - 3-Methyl-l-phenylpyrazol-5-yl 2.571 OH O O OMe OMe - 1,4-Dimethylpyrazol-5-yl 2.572 OH O O OMe OMe - 1,3-Dimethylpyrazol-5-yl 2.573 OH O O OMe OMe - ~enzopyrazol-l-yl 2.574 OH O O OMe OMe - l-Methylbenzopyrazol-3-yl 2.575 OH O O OMe OMe - l-Imidazolyl 2.576 H O O OMe OMe - l-Imidazolyl 2.577 OH O O OMe OMe - 2-Methylimidazol-l-yl 21~675!-1 _~ ~ ~ ~ ~ 11~1 U) r-l~1 ~I r l ~
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2.693 OH O O OMe OMe - 3-Methyl-4-chloroisoxazol-5-yl 2.694 OH O O OMe OMe - 3-Methylisoxazol-4-yl 2.695 OH O O OMe OMe - 3,5-Dimethylisoxazol-4-yl 2.696 OH O O OMe OMe - 4-Methoxyisoxazol-3-yl 2.697 OH O O OMe OMe - 5-Methoxyisoxazol-3-yl 2.698 OH O O OMe OMe - 3-Methoxyisoxazol-4-yl 2.699 OH O O OMe OMe - 5-Methoxyisoxazol-4-yl 2.700 OH O O OMe OMe - 3-Methoxyisoxazol-5-yl 2.701 OH O O OMe OMe - 4-Methoxyisoxazol-5-yl 2.702 OH O o OMe OMe - 2-Thiazolyl 67~

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2.725 OPh O O OMe OMe - 2-Thiazolyl 2.726 o-C6H4-4-NO2 OMe OMe - 2-Thiazolyl 2.727 ON=CMe2 O O OMe OMe - 2-Thiazolyl 2.728 ON=CMe2 O S OMe OMe - 2-Thiazolyl 2.729 O O OMe OMe - 2-Thiazolyl 2.730 ON=CHe-SMe O O OHe OHe - 2-Thiazolyl 2.731 0-NMe2 0 0 OMe OMe - 2-Thiazolyl ~ ~-2.732 O-(l-Piperidyl) O O OMe OMe - 2-Thiazolyl 2.733 0-(4-Morpholinyl) O O OMe OMe - 2-Thiazolyl 2.734 ~ O O OMe OMe - 2-Thiazolyl -- N/~ .
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2.735 1-Pyrrolyl O O OMe OMe - 2-Thiazolyl 2.736 1-Pyrazolyl O O OMe OMe - 2-Thiazolyl 2.737 1-Imidazolyl O O OMe OMe - 2-Thiazolyl 2.738 1,2,4-Triazol-l-yl O O OMe OMe - 2-Thiazolyl ~- 21667~ll -m OCCiOOCCCOCCCCCCOCCCCC
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No . Rl W X Y Z ( R2 ) n Het 2.859 H N-OEt O OMe OMe - 2-Pyridyl 2.860 ,H N-OtBu O OMe OHe - 2-Pyridyl 2.861 H N-OCH=CH2 O OMe OMe - 2-Pyridyl 2.862 H N-OCH2CH=CH2 OMe OMe - 2-Pyridyl 2.863 H N-OPh O OMe OMe - 2-Pyridyl 2.864 H 'N-NH2 O OMe OMe - 2-Pyridyl 2.865 H N-NHMe O OMe OMe - 2-Pyridyl 2.866 H N I.lc2 O OMe OMe - 2-Pyridyl 2.867 H N-NHPh O OMe OMe - 2-Pyridyl 2.868 OH O O OMe OMe - 3-Pyridyl 2.869 H O O OMe OMe - 3-Pyridyl ~ CJ~
2.870 OH O S OMe OMe - 3-Pyridyl 2.871 OH O NH OMe OMe - 3-Pyridyl 2.872 OH O N-CN OMe OMe - 3-Pyridyl 2.873 OH N-OH O OMe OMe - 3-Pyridyl 2.874 OH N-OMe O OMe OMe - 3-Pyridyl 2.875 OH O O OMe OMe 5-Me 3-Pyridyl 2.876 O~Na+ O O OMe OMe - 3-Pyridyl 2.877 O-K+ O O OMe OMe - 3-Pyridyl 2.878 O~ l/2Ca2+ O O OMe OMe - 3-Pyridyl 2.879 O-(NH4)+ O O OMe OMe - 3-Pyridyl No . Rl W . X Y Z ( R2 ) n Het 2.880 O~(NMe4)~ O O OMe OMe - 3-Pyridyl 2.881 OMe O O OMe OMe - 3-Pyridyl 2.882 OEt O O OMe OHe - 3-Pyridyl 2.883 O-CH2-OMe O O OMe OMe - 3-Pyridyl 2.884 O-CH2-SMe O O OMe OMe - 3-Pyridyl 2.885 OCH2CH=CH2 OMe OMe - 3-Pyridyl 2.886 OCH2C-CH O O OMe OMe - 3-Pyridyl 2.887 ~ ~ O O OMe OMe - 3-Pyridyl O N
2.888 O-Cyclopropyl O O OMe OMe - 3-Pyridyl C~2.889 OCH2-CO2Me O O OMe OMe - 3-Pyridyl ~ _~
2.890 1 0 0 OMe OMe - 3-Pyridyl 0 ~0 2.891 OPh O O OMe OMe - 3-Pyridyl 2.892 O-C6H4-4-NO2 OMe OMe - 3-Pyridyl 2.893 ON=CMe2 O O OMe OMe - 3-Pyridyl 2.894 ON=CMe2 O S OMe OMe - 3-Pyridyl 2.895 O O O OMe OMe - 3-Pyridyl ~0 2.896 ON=CMe-SMe O O OMe OMe - 3-Pyridyl No . Rl W X Y Z ( R2 ) n Het 2.897 O-NMe2 O O OMe OMe - 3-Pyridyl 2.898 O-(l-Piperidyl) O O OMe OMe - 3-Pyridyl 2.899 0-(4-Morpholinyl) O O OMe OHe - 3-Pyridyl 2.900 ~\ O O OMe OMe - 3-Pyridyl -- N~
O
2.901 l-Pyrrolyl O O OMe OMe - 3-Pyridyl 2.902 1-Pyrazolyl O O OMe OMe - 3-Pyridyl 2.903 1-Imidazolyl O O OMe OMe - 3-Pyridyl ~
2.904 1,2,4-Triazol-1-yl O O OMe OMe - 3-Pyridyl w ~ .
2.905 NH-S02Me O O OMe OMe - 3-Pyridyl 2.906 NH-SO2Ph O O OMe OMe - 3-Pyridyl 2.907 NHSOzC6H4-4-Me O O OMe OMe - 3-Pyridyl 2.908 H O O OMe OMe - 3-Pyridyl 2.909 Me O O OMe OMe - 3-Pyridyl 2.910 H NMe O OMe OMe - 3-Pyridyl 2.911 H NtBu O OMe OMe - 3-Pyridyl 2.912 H NPh O OMe OMe - 3-Pyridyl 2.913 H N-OH O OMe OMe - 3-Pyridyl 2.914 H N-OMe O OMe OMe - 3-Pyridyl No . Rl W X Y Z t R2 ) n Het 2.915 H N-OEt O OMe OMe - 3-Pyridyl 2.916 ,H N-OtBu O OMe OMe - 3-Pyridyl 2.917 H N-OCH=CH2 O OMe OMe - 3-Pyridyl 2.918 H N-ocH2cH=cH2 OMe OMe - 3-Pyridyl 2.919 H N-OPh O OMe OMe - 3-Pyridyl 2.920 H N-NH2 O OMe OMe - 3-Pyridyl 2.921 H N-NHMe O OMe OMe - 3-Pyridyl 2.922 H N-NMe2 0 OMe OMe - 3-Pyridyl r~
2.923 H N-NHPh O OMe OMe - 3-Pyridyl 2.924 OH - O O OMe OMe - 4-Pyridyl 2.925 H O O OMe OMe - 4-Pyridyl 2.926 OH O S OMe OMe - 4-Pyridyl 2.927 OH O NH OMe OMe - 4-Pyridyl 2.928 OH O N-CN OMe OMe - 4-Pyridyl 2.929 OH N-OH O OMe OMe - 4-Pyridyl 2.930 OH N-OMe O OMe OMe - 4-Pyridyl 2.931 OH O O OMe OMe 5-Me 4-Pyridyl 2.932 O~Na+ O O OMe OMe - 4-Pyridyl 2.933 O-K+ O O OMe OMe - 4-Pyridyl 2.934 O~ l/2Ca2+ O O OMe OMe - 4-Pyridyl 2.935 O-(NH4)+ O O OMe OMe - 4-Pyridyl No . Rl W X Y Z ( R2 ) n Het 2.936 O~(NMe4)+ O O OMe OMe - 4-Pyridyl 2.937 OMe O O OMe OHe - 4-Pyridyl 2.938 OEt O O OMe OMe - 4-Pyridyl 2.939 O-CH2-OMe O O OMe OMe - 4-Pyridyl 2.940 O-CH2-SMe O O OMe OMe - 4-Pyridyl 2.941 OCH2CHzCH2 OMe OMe - 4-Pyridyl 2.942 OCH2C_CH O O OMe OMe - 4-Pyridyl 2.943 ~ ~ O O OMe OMe - 4-Pyridyl O N
2.944 O-Cyclopropyl O O OMe OMe - 4-Pyridyl 2.945 OCH2-CO2Me O O OMe OMe - 4-Pyridyl 2.946 1 0 0 OMe OMe - 4-Pyridyl 0 ~,0 2.947 OPh O O OHe OMe - 4-Pyridyl 2.948 o-C6H4-4-NO2 OMe OMe - 4-Pyridyl 2.949 ON=CMe2 O O OMe OMe - 4-Pyridyl 2.950 ON=CMe2 O S OMe OMe - 4-Pyridyl 2.951 O O OMe OMe - 4-Pyridyl ~0 2.952 ON=CMe-SMe O O OMe OMe - 4-Pyridyl No . Rl W X Y Z ( R2 ) n Het 2.953 O-NMe2 O O OMe OMe - 4-Pyridyl 2.954 ,O-(l-Piperidyl) O O OMe OMe - 4-Pyridyl 2.955 0-~4-Morpholinyl) O O OMe OMe - 4-Pyridyl 2.956 O O OMe OMe - 4-Pyridyl 2.956 ~\ O O OMe OMe - 4-Pyridyl -- N~J
O
2.957 1-Pyrrolyl O O OHe OMe - 4-Pyridyl 2.958 l-Pyrazolyl O O OMe OMe - 4-Pyridyl ~
2.559 l-Imidazolyl O O OMe OMe - 4-Pyridyl ~Z
2.660 1,2,4-Triazol-l-yl O O OMe OMe - 4-Pyridyl 2.961 NH-SO2Me O O OMe OMe - 4-Pyridyl 2.962 NH-SO2Ph O O OMe OMe - 4-Pyridyl 2.963 NHSO2C6H4-4-Me O O OMe OMe - 4-Pyridyl 2.964 H O O OMe OHe - 4-Pyridyl 2.965 Me O O OMe OMe - 4-Pyridyl 2.966 H NMe O OMe OMe - 4-Pyridyl 2.967 H NtBu O OMe OMe - 4-Pyridyl 2.969 H NPh O OMe OMe - 4-Pyridyl 2.970 H N-OH O OMe OMe - 4-Pyridyl 2.971 H N-OMe O OMe OMe - 4-Pyridyl ~1667~ 1 4 4 '4 4 4 4 ~4 ~4 4 4 4 1.~4 ~4 4 ~4 ~4 L14 4 ~4 ~
~U I I

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o ~ o ~ c c c e c ~ c c ~ c ~
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L L
L L L L L L L L ~ J
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~ oooooooooooooo No . Rl W X Y Z ( R2 ) n Het 2.1014 OH O O OMe OMe - 2-Ethoxy-6-pyridyl 2.1015 pH O O OMe OMe - 6-Ethoxy-S-pyridyl 2.1016 OH O O OMe OMe - 4-Ethoxy-5-pyridyl 2.1017 OH O O OMe OMe - 3-Ethoxy-5-pyridyl 2.1018 OH O O OMe OMe - 2-Ethoxy-S-pyridyl 2.1019 OH O O OMe OMe - 2-Ethoxy-4-pyridyl 2.1020 OH O O OMe OMe - 3-Ethoxy-4-pyridyl 2.1021 OH O O OMe OMe - 5-Isopropoxy-6-pyridyl 2.1022 OH O O OMe OMe - 4-Isopropoxy-6-pyridyl ~3 2.1023 OH O O OMe OMe - 3-Isopropoxy-6-pyridyl 2.1024 OH O O OMe OMe - 2-Isopropoxy-6-pyridyl 2.1025 OH O O OMe OMe - 6-Isopropoxy-5-pyridyl 2.1026 OH O O OMe OMe - 4-Isopropoxy-5-pyridyl 2.1027 OH O O OMe OMe - 3-Isopropoxy-5-pyridyl 2.1028 OH O O OMe OMe - 2-Isopropoxy-5-pyridyl 2.1029 OH O O OMe OMe - 2-Isopropoxy-4-pyridyl 2.1030 OH O O OMe OMe - 3-Isopropoxy-4-pyridyl 2.1031 OH O O OMe OMe - 5-Difluoromethoxy-6-pyridyl 2.1032 OH O O OMe OMe - 4-Difluoromethoxy-6-pyridyl 2.1033 OH O O OMe OMe - 3-Difluoromethoxy-6-pyridyl 2.1034 OH o O OMe OMe - 2-Difluoromethoxy-6-pyridyl No . Rl W X Y Z ( R2 ) n Het 2.1035 OH O O OMe OMe - 6-Difluoromethoxy-5-pyridyl 2.1036 OH O O OMe OMe - 4-Difluoromethoxy-S-pyridyl 2.1037 OH O O OMe OMe - 3-Difluoromethoxy-5-pyridyl 2.1038 OH O O OMe OMe - 2-Difluoromethoxy-5-pyridyl 2.1039 OH O O OMe OMe - 2-Difluoromethoxy-4-pyridyl 2.1040 OH ' O O OMe OMe - 3-Difluoromethoxy-4-pyridyl 2.1041 OH O O OMe OMe - 5-Methylthio-6-pyridyl 2.1042 OH O O OMe OMe - 4-Methylthio-6-pyridyl 2.1043 OH O O OMe OMe - 3-Methylthio-6-pyridyl 2.1044 OH O O OMe OMe - 2-Methylthio-6-pyridyl 2.1045 OH O O OMe OMe - 6-Methylthio-5-pyridyl 0 C~
2.1046 OH O O OMe OMe - 4-Methylthio-5-pyridyl C~
2.1047 OH O O OMe OMe - 3-Methylthio-5-pyridyl 2.1048 OH O O OMe OMe - 2-Methylthio-5-pyridyl 2.1049 OH O O OMe OMe - 2-Methylthio-4-pyridyl 2.1050 OH O O OMe OMe - 3-Hethylthio-4-pyridyl 2.1051 OH O O OMe OMe - 5-Dimethylamino-6-pyridyl 2.1052 OH O O OMe OMe - 4-Dimethylamino-6-pyridyl 2.1053 OH O O OMe OMe - 3-Dimethylamino-6-pyridyl 2.1054 OH O O OMe OMe - 2-Dimethylamino-6-pyridyl 2.1055 OH O O OMe OMe - 6-Dimethylamino-5-pyridyl - 21~6754 ,.........

Ln Ln u~

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- 216675 ~

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No . Rl W XY Z Al A2 A3 A4 ( R2) n 3.013 OMe O O OMeOMe N CH CH CH -3.014 OEt O O OMeOMe N CH CH CH
3.015 O-CH2-OMe O O OMeOMe N CH CH CH
3.016 O-CH2-SMe O O OMeOMe N CH CH CH
3.017 OCH2CH=CH2 OMe OMe N CH CH CH
3.018 OCH2C_CH O, O OMeOMe N CH CH CH
3.019 ~ O O OMeOMe N CH CH CH
O N ~_~
3. 020 O-Cyclopropyl O O OMe OMe N CH CH CH - C5 3 .021 OCH2-CO2Me O O OMe OMe N CH CH CH - -~
3.023 1 0 0 OMe OMe N CH CH CH - ~ c~n 0 ~,0 3.024 OPh O OOMe OMe N CH CH CH
3.025 o-C6H4-4-NO2 OMe OMe N CH CH CH
3.026 ON=CMe2 0 0OMe OMe N CH CH CH
3.027 ON=CMe2 O SOMe OMe N CH CH CH
3.028 o O OOMe OMe N CH CH CH
~0 3.029 ON=CMe-SMe O OOMe OMe N CH CH CH
3.030 O-NMe2 O OOMe OMe N CH CH CH
3.031 O-(l-Piperidyl) O o OMe OMe N CH CH CH

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No. Rl W XY Z Al A2 A3 A4 (R2) n3.051 H N-OCH2CH=CH2 OMe OMe N CH CH CH
3.052 H N-OPh O OMe OMe N CH CH CH
3.053 H N-NH2 O OMe OMe N CH CH CH
3.054 H N-NHMe O OMe OMe N CH CH CH
3.055 H N-NMe2 O OMe OMe N CH CH CH
3.056 H N-NHPh O OMe OMe N CH CH CH
3.057 OH O O OMe OMe CH N CH CH
3.0S8 OH O O OMe OMe CH CH N CH
3.059 OH O O OMe OMe CH CH CH N
3.060 OH O O OMe OMe N CH CH CH - ~__3.061 OH O O OMe OMe N CH CH CH 5-NMe2 cr 3.062 OH O O OMe OMe N CH CH CH 5-Cl o -~
3.063 OH O O OMe OMe N CH CH CH 5-OMe C~
3.064 OH O O OMe OMe N CH CH CH 5-SMe 3.065 OH O O OMe OMe N CH CH CH 5-Ph 3.066 OH o o OMe OMe N CH CH CH 5-(4-Chlorophenyl) 3.067 OH O O OMe OMe N CH CH CH 5-(4 B~ Pnyl) 3.068 OH O O OMe OMe N CH CH CH 5-(4-Methoxy-2-pyridyl) 3.069 OH O O OMe OMe N CH CH CH 5-(3-Methoxy-2-pyridyl) 3.070 OH O O OMe OMe N CH CH CH 5-(4-Methoxy-3-pyridyl) 3.071 OH O O OMe OMe N CH CH CH 5-(3-Methoxy-4-pyridyl) 3.072 OH O O OMe OMe N CH CH CH 5-(2-Thienyl) -- 21667~4 ... .... ... ... ............ , ~
, _ , .. _ ~. C
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W~ R

No. Rl W X Y Z (R2)n C~
4.001 OH O O OMe OMe -4.002 OH O S OMe OMe - ~ C~
4.003 OH O NH OMe OMe 4.004 OH O N-CN OMe OHe 4.005 OH N-OH O OMe OMe 4.006 OH N-OMe O OMe OMe 4.007 OH O O OMe OMe 4.008 O~Na+ O O OMe OMe 4.009 O-K+ O O OMe OMe 4.010 O~ l/2Ca2+ O O OMe OMe 4.011 O-(NH4)+ OMe OMe No- Rl W XY Z (R2)n 4.012 O~(NMe4)+ O O OMe OMe 4.013 OMe O O OHe OMe 4.014 OEt O O OMe OMe 4.015 O-CH2-OMe O O OMe OMe 4.016 O-CH2-SMe O O OMe OMe 4.017 OCH2CH=CH2 OMe OMe 4.018 OCH2C_CH O O OMe OMe 4.019 ~ ~ O O OMe OMe -O N ~5~
4.020 O-Cyclopropyl O O OHe OMe -4.021 OCH2-C02Me O O OMe OMe - C
4.023 1 O O OMe OMe N
4.024 OPh O O OMe OMe 4.025 O-C6H4-4-NO2 OMe OMe 4.026 ON=CMe2 O O OMe OMe 4.027 ON=CMe2 O S OMe OMe 4.028 O O O OMe OMe \,~=o 4.029 ON=CMe-SMe O O OMe OMe -- 2~6~S4 .

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No. Rl W XY Z (R2)n 4.070 OHe O O OHe OHe 6-Cl 4.072 O,Et O O OHeOHe 6-Cl 4.073 O-CH2-OHe O O OHeOMe 6-Cl 4.074 O-CH2-SHe O O OHeOMe 6-Cl 4.075 OCH2CH=CH2 O OHe OMe 6-Cl 4.076 OCH2C_CH O O OHeOHe 6-Cl 4.077 ~ ~ o O OHeOMe 6-Cl O N
4.078 O-Cyclopropyl O O OMe OMe 6-Cl 4.079 OCH2-CO2Me O OOHe OMe 6-Cl ~_~
4.080 1 0 0 OMeOMe 6-Cl ~ cJ~
~0 Ul C~
4.081 OPh O OOHe OMe 6-Cl 4.082 o-C6H4-4-NO2 OHe OHe 6-Cl 4.083 ON=CMe2 O OOHe OHe 6-Cl 4.084 O O OOHe OHe 6-Cl ~0 4.085 ON=CMe-SHe O OOHe OMe 6-Cl 4.086 O-NMe2 O OOMe OMe 6-Cl 4.087 O-(1-Piperidyl) O O OMe OHe 6-Cl - ~16675il -yy yyyyyyyyyyuyyyyyy o o~0 0 æO Oæ æO ~0 ~0 æO O OX O 0 ~0 Oæ ~ g æO æOOæ æO Oæ æO æO o Oæ 0 æO æO Oæ 3 0 æO ~ æ

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-~U UUU UUUU UUUUU U

O O O O O O O O O 0 0~ 0 0 0 0 O O O O O O O O ~ ~0 0 0 0 0 0 Oo ooO OOOO OOOOO o -,1 ~ ~

U ~~ o N ~ O U ~ ~r U \b ~) ~ o/ pl U 11 ~ ~~ z O - O O O O O O O O O -~
~ O~ O _I ~ ~) ~ ~1 ~ 1~ CO O~ O
Z

No . Rl W X Y Z ( R2 ) n 4.143 1-Pyrazolyl O S OMe OMe 6-Cl 4.144 l-Imidazolyl O S OHe OMe 6-Cl 4.145 1,2,4-Triazol-1-yl O S OMe OMe 6-Cl 4.146 NH-SO2Me O S OMe OMe 6-Cl 4.147 NH-SO2Ph O S OMe OMe 6-Cl 4.148 NHSO2C6H4-4-Me 'O . S OMe OMe 6-Cl 4.149 H O S OMe OHe 6-Cl 4.150 Me O S OMe OMe 6-Cl 4.151 H NMe S OMe OMe 6-Cl 4.152 H NtBu S OMe OMe 6-Cl 2 4.153 H NPh S OMe OMe 6-Cl CJ~
4.154 H N-OH S OMe OMe 6-Cl _~
4.155 H N-OMe S OMe OMe 6-Cl CJ~
4.156 H N-OEt S OMe OMe 6-Cl 4.157 H N-OtBu S OMe OMe 6-Cl 4.158 H N-OCH=CH2S OMe OMe 6-Cl 4.159 H N-OCH2CH=CH2 SOMe OMe 6-Cl 4.160 H N-OPh S OMe OMe 6-Cl 4.161 H N-NH2 S OMe OMe 6-Cl 4.162 H N-NHMe S OMe OMe 6-Cl 4.163 H N-NMe2 S OMe OMe 6-Cl 2 1 ~ 4 N

-~ S 2 ~ X ~ ~
~ N --I ~ U l O l O
s m 2 U U I 11 .~ ~S O
~ , u u u 1l u U m I I z 1I z u u ml ~ IIY u lu lu lu u U lu lu u u u lu u lu O O O O O O O O O O O O O O O O O O O O O

ooooooooooooooooooooo U~oooooooooooooooooooo g ps, z Zoooooooooooooooooooo m m m m m m m m m m m m m m m m m m m m m o- o o o o o o o o o o o o o o o o o o o z No. Rl W X Y Z (R2)n 4.185 OH O O OMe OMe 6-CH=N-O-Ph 4-186 O,H O O OMe OHe 6-~MC-~7 O-Ph 4.187 OH O O OMe OMe 6-OMe 4.188 OH O O OMe OMe 6-OCHF2 4.189 OH O O OMe OMe 6-OEt 4.l90 OH O O OMe OMe (~la~) 4.191 OH O O OHe OMe 6- ~ ~ C1 E

~n 4.192 OH O O OMe OMe 6-OCFzCHF
4.193 OH O O OMe OMe 6-OCH2CH=CH2 4.194 OH O O OHe OMe 6-0-Ph 4.l95 OH O O OMe OMe 6-0-(4-Chlorophenyl) 4.l96 OH O O OMe OMe 6-0-(4-Bromophenyl) 4.197 OH O O OMe OMe 6-0-(4-Isopropoxyphenyl) 4.l98 OH O O OMe OMe 6-0-(2-Hethylphenyl) 4.l99 OH O O OMe OMe 6-0-(3-Methoxyphenyl) 4.200 OH O O OMe OMe 6-0-(2-Pyridyl) 4.20l OH O O OMe OMe 6-0-(3-Pyridyl) No. Rl W X Y Z (R2)n 4.202 OH O O OMe OMe 6-O-(4-Pyridyl)4.203 OH O O OMe OMe 6-0-(6-Hethoxy-2-pyridyl) 4.204 OH O O OMe OMe 6-O-(2-Pyrimidyl) 4.205 OH O O OHe OMe 6-O-(3-Pyrimidyl) 4.206 OH O O OHe OMe 6-o-(4-pyrimidyl) 4.207 OH O O OMe OMe 6-0-(1,3,5-Triazinyl) 4.208 OH O OMe OMe 6-O-(1-Pyrazolyl) 4.209 OH O O OMe OMe 6-O-(1-Methylpyrazol-4-yl) 4.210 OH O O OMe OMe 6-SMe 4.211 OH O O OMe OMe 6-SPh ~' 4.212 OH O O OMe OMe 6-SO2Me 4.213 OH O O OMe OMe 6-SO2Ph ~ ~~
4.214 OH O OMe OMe 6-S02-C6H4-4-Me 4.215 OH O O OMe OMe 6-4.215 OH O O OMe OMe 6- ~ /F

~ ~ N
4.216 OH O o OMe OMe 4.217 OH O O OMe OMe 6-NMe2 4.218 OH O O OMe OMe 6-O-(2-Naphthyl) `- 216~7~

N a~
P:
In a~ a~ a~ ~ a~
oUooo~ooo~oo a~ a) a~ ~ a~
ooooooooo O o ~n z o o o o o o o a~ ~\ Z
:~ Z~ o ol ooooZZooooo 3 ~3~
/=, 3 N
O

Z Z ~ Z
-o mO o o o o o o o b o U~
a . O O O O O O O o o _1 1 ~ o O O O O o O O o o o o r z No. R1 W XY Z (R2)n 5.012 O~(NMe4)+ O O OMe OMe 5.013 O,Me O O OMe OMe 5.014 OEt O O OMe OMe 5.015 O-CH2-OMe O O OMe OMe 5.016 O-CH2-SMe O O OMe OMe 5.017 OCH2CH=CH2 OMe OMe 5.018 OCH2C_CH O O OMe OMe 5.019 ~ ~ O O OMe OMe O N
5.020 O-Cyclopropyl O O OMe OMe 5.021 OCH2-C02Me O O OMe OMe 5.022 1 0 0 OMe OMe 0 ~,0 5.023 OPh O O OMe OMe - -5.024 o-C6H4-4-NO2 OMe OMe 5.025 ON=CMe2 O O OMe OMe 5.026 ON=CMe2 O S OMe OMe 5.027 O . O O OMe OMe ~0 5.028 ON=CMe-SMe O O OMe OMe No. Rl W X Y Z
5.029 O-NMe2 O O OMe OMe 5.030 O~ Piperidyl) O O OMe OMe 5.031 0-(4-Morpholinyl) O O OMe OMe 5.032 O-NEt2 O O OMe OMe ~ O OMe OMe 5.034 1-Pyrrolyl O O OMe OMe 5.035 1-Pyrazolyl O O OMe OMe 5.036 l-Imidazolyl O O OMe OMe 5.037 1,2,4-Triazol-l-yl O O OMe OMe 5.038 NH-S02Me O O OMe OMe 5.039 NH-S02Ph O O OMe OMe 5.040 NHSO2C6H4-4-Me O O OMe OMe 5.041 H - O O OMe OMe 5.042 Me O O OMe OMe 5.043 H NMe O OHe OMe 5.044 H NtBu O OMe OMe 5.045 H NPh O OMe OMe 5.046 H N-OH O OMe OMe 5.047 H N-OMe O OMe OMe No. Rl W XY Z (R2)n 5.048 H N-OEt O OMe OMe 5.049 H N-OtBu O OMe OMe 5.050 H N-OCH=CH2 O OMe OMe 5.051 H N-OCH2CH=CHz O OMe OMe 5.052 H N-OPh O OMe OMe 5.053 H 'N-NH2 O OMe OMe 5.054 H N-NHMe O OMe OMe 5.055 H N-NMe2 O OHe OMe 5.056 H N-NHPh O OMe OMe 2`5 216 6 ~ 5 i~

Preparation examples 5-Fluoro-4,6-dihydroxy-2-methylsulfonylpyrimidine 44 g (0.293 mol) of dimethyl 2-fluoromalonate were dissolved in 450 ml of methanol and treated with 106.5 g (0.59 mol) of 30 NaOMe solution. 41.6 g (0.15 mol) of bis(S-methylisothiourea) sulfate were then added and the mixture was stirred at RT for lO three days. It was then concentrated, and the residue was dis-solved in water and brought to pH 1 using hydrochloric acid. The solid which was deposited was filtered off with ~uction and re-crystallized from 1200 ml of water. 18 g of a colorless solid, m.p. 230-238 C, were obtained. The mother liquor was concentrated to 100 ml, a further 4.6 g of product (m.p. 230 C) being de-posited. Total yield: 22.6 g (44~).

4,6-Dichloro-5-fluoro-2-methylsulfonylpyrimidine 20 19.7 g (0.112 mol) of 5-fluoro-4,6-dihydroxy-2-methyl~ulfonyl-pyrimidine were dissolved in 103 g (0.67 mol) of phosphorus oxychloride and treated with 8.2 g (0.068 mol) of N,N-dimethyl-aniline. The mixture was heated under reflux until starting material was no longer present (about 4 h). The mixture was al-lowed to cool and was concentrated, 100 ml of water were added, the mixture was stirred and the precipitate which deposited was filtered off with suction. It was washed with ice water and dried at 40 C under reduced pressure. 19.9 g (83~) of a colorless solid, m.p. 54-56 C, remained.
5-Fluoro-4,6-dimethoxy-2-methylsulfonylpyrimidine 9 g (42 mmol) of 4,6-dichloro-5-fluoro-2-methylsulfonylpyrimidine were dissolved in 32 ml of methanol and treated with 22.7 g (126 mmol) of sodium methoxide solution (30~). The mixture was additionally heated at 50 C for 4 h, a solid being deposited.
After cooling to room temperature, it was adjusted to pH 7 using glacial acetic acid and stirred into 100 ml of ice water. The precipitate formed was filtered off with suction, washed with ice 40 water and dried at room temperature on an oil pump. 8.1 g (94~) of a colorless powder, m.p. 78-79 C, were obtained.

5-Fluoro-4,6-dimethoxy-2-methylsulfonylpyrimidine 11.6 g (57 mmol) of 5-fluoro-4,6-dimethoxy-2-methylsulfonyl-pyrimidine were initially introduced into 80 ml of glacial acetic acid, 0.86 g of disodium tungstate was added and the mixture was warmed to 30 C. 17.1 ml (171 mmol) of hydrogen peroxide solution (30%) were then added and the mixture was stirred overnight at room temperature. It was poured into 400 ml of ice water, the mixture was stirred for 30 min and the precipitate was then fil-tered off with suction and washed with ice water. After drying in a vacuum drying oven at 50 C, 12.1 g (90%) of a colorless solid, m.p. 130-133 C, remained.

2-(5-Fluoro-4,6-dimethoxypyrimidin-2-yloxy)-6-phenylbenzoic acid lO (Comp. 1.001) 1.8 g (8.5 mmol) of 6-phenylsalicylic acid were dissolved in 30 ml of dried dimethyl sulfoxide and treated in portions with 1.9 g (17 mmol) of potassium tert-butoxide, the temperature of the reaction mixture rising to approximately 30 C. The mixture was cooled to room temperature, 2.0 g (8.5 mmol) of 5-fluoro-4,6-dimethoxy-2-methylsulfonylpyrimidine were added and it was stirred at 60 C for approximately 4 h. The reaction mixture was poured into a mixture of 100 ml of cold water and 2 ml of ortho-20 phosphoric acid and extracted with methyl tert-butyl ether. The organic phase was washed with a little water, dried over sodium sulfate and concentrated. The residual oil was purified by chro-matography on silica gel using hexane/acetone. 2.4 g of a color-less powder, m.p. 178-182 C, were obtained.

The following compounds were prepared in a similar manner to the process described above:

1.004 6-(4-Chlorophenyl)-2-(5-fluoro-4,6-dimethoxy-pyrimidin-2-yloxy)benzoic acid, m.p. 160-165 C

1.007 6-(4-Bromophenyl)-2-(5-fluoro-4,6-dimethoxy-pyrimidin-2-yloxy)benzoic acid, m.p. 160-168 2.1008 6-(2-Methoxy-6-pyridyl)-2-(5-fluoro-4,6-dimethoxy-pyrimidin-2-yloxy)benzoic acid, m.p. 178 C

2.1014 6-(2-Ethoxy-6-pyridyl)-2-(5-fluoro-4,6-dimethoxy-pyrimidin-2-yloxy)benzoic acid, m.p. 178-179 C.

Claims (11)

1. A fluorinated pyrimidine of the formula I

(I) where A is one of the following radicals:

and where the symbols have the following meanings:

W is =O, =N-R3, =N-O-R3, =N-NR4R5;

X is -O-, -S- or -NR6-;

Y and Z are halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino and/or dialkylamino;

R1 is hydrogen;

alkyl, alkylcarbonyl, alkoxycarbonyl;
2 a succinyliminooxy group;

a 5-membered heteroaromatic comprising one to three nitrogen atoms which can carry one to four halogen atoms and/or one or two of the following radicals:
alkyl, haloalkyl, alkoxy, haloalkoxy andtor alkylthio;
a radical OR7;
a radical where R8 and R9 can be identical or different;

or a radical R2 is hydrogen;
halogen;
amino;

alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfonyl, alkylamino, dialkylamino, which can carry one of the following substituents, which in the case of dialkylamino can be identical or different:
alkoxy, alkylthio, dialkylamino, thienyl, furyl, a five-membered aromatic heterocycle having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, it being possible for the five-membered-ring heterocycles to carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl; or phenyl which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups; or phenoxy which is
3 unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups, or a six-membered aromatic heterocycle having one to three nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl;
phenyl, substituted phenyl;
phenoxy, substituted phenoxy;

phenylthio, substituted phenylthio, phenylsulfonyl, substituted phenylsulfonyl;

a five-membered heteroaromatic having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzo-fused 5-membered heteroaromatic, which can comprise one to three nitrogen atoms or a nitrogen atom and additionally an oxygen or sulfur atom and can carry one of the following radicals: halogen, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a thienyl or furyl radical which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzothienyl or benzofuryl radical, which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
4 a 6-membered heteroaromatic having one to four nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals:
nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical which in each case can carry up to three halogen atoms and/or up to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a 5-membered heteroaromatic bonded via an oxygen atom and having one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzo-fused 5-membered heteroaromatic bonded via an oxygen atom, which can contain one to three nitrogen atoms or a nitrogen atom and additionally an oxygen or sulfur atom and can carry one of the following radicals: halogen, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a thienyl or furyl radical bonded via an oxygen atom, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a benzothienyl or benzofuryl radical bonded via an oxygen atom, which can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one
5 to three halogen atoms and/or one to three methyl groups;

a 6-membered heteroaromatic bonded via an oxygen atom and having one to four nitrogen atoms in the ring, which can carry one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;

a naphthyl, quinolinyl, isoquinolinyl or quinazolinyl radical bonded via an oxygen atom, which in each case can carry one to three halogen atoms and/or up to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or phenyl, which is unsubstituted or substituted by one to three halogen atoms and/or one to three methyl groups;
a radical where X' and Z' have the meanings indicated above for X
and Z and can be identical to or different from them;
a group where W' and R1' have the same meanings as W and R1, and can be identical to or different from these units;

R3 is hydrogen, phenyl, substituted phenyl or alkyl, alkenyl or alkynyl, which can carry one to three of the following substituents: halogen, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carboxyl, alkylthio, phenyl, substituted phenyl;
R4 is hydrogen, alkyl or phenyl;

R5 is hydrogen, phenyl, substituted phenyl or alkyl which can carry one to three of the following substituents:
halogen, alkoxy, alkylcarbonyl, alkoxycarbonyl, carboxyl, alkylthio, phenyl, substituted phenyl;
R6 is hydrogen, alkyl, formyl, carbamoyl or alkoxycarbonyl;

R7 is hydrogen, an alkali metal cation, an equivalent of an alkaline earth metal cation or an organic ammonium ion;

a cycloalkyl group which can carry one to three alkyl radicals;

an alkyl group which can carry one to five halogen atoms and/or one or two of the following radicals:
alkoxy, alkylthio, cyano, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, a radical -O-N=CR11R12, where R11 and R12 can be identical or different, phenyl, phenoxy or phenylcarbonyl, it being possible for the aromatic radicals in turn to carry one to five halogen atoms and/or one to three of the following radicals: alkyl, haloalkyl, alkoxy, haloalkoxy and/or alkylthio;

an alkyl group which can carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic containing one to three nitrogen atoms, which can carry one to four halogen atoms and/or one or two of the following radicals:
alkyl, haloalkyl, alkoxy, haloalkoxy and/or alkylthio;

an alkyl group which in the 2-position carries one of the following radicals: alkoxyimino, alkenyloxyimino, haloalkenyloxyimino or benzyloxyimino;

an alkenyl or an alkynyl group, it being possible for these groups in turn to carry one to five halogen atoms;
phenyl which is unsubstituted or mono- to trisubstituted by nitro, alkyl or alkoxy or mono- to pentasubstituted by halogen;

a radical -N=CR13R14, where R13 and R14 can be identical or different;

a 5-membered aromatic heterocycle bonded via a nitrogen atom and having one to four nitrogen atoms in the ring or a benzo-fused 5-membered aromatic heterocycle bonded via a nitrogen atom and having one to three nitrogen atoms in the ring, which can be substituted by halogen, alkyl or haloalkyl;
R3 and R9 are hydrogen;

alkyl, alkenyl or alkynyl, it being possible for these radicals in each case to carry one to five halogen atoms and/or one or two of the following groups:
alkoxy, alkylthio, cyano, alkylcarbonyl, alkoxycarbonyl, dialkylamino, cycloalkyl;

cycloalkyl, which can carry one to three alkyl substituents;
Phenyl or substituted phenyl;

together are an alkylene chain closed to give a ring or together are an alkylene chain closed to give a ring with a heteroatom, which can be oxygen, sulfur or nitrogen, and which in each case can carry one to three alkyl substituents;
or a group R10 is alkyl or phenyl, which can carry one to four of the following substituents: halogen, nitro, cyano, alkyl;

R11 and R12 are alkyl, which can carry an alkoxy or alkylthio group, or together are an alkylene chain;

R13 and R14 are alkyl which can carry a phenyl radical, or an alkoxy and/or an alkylthio group, cycloalkyl, phenyl, or together are an alkylene chain which can carry one to five alkyl groups and can be bridged by an alkylene chain;

R15 is hydrogen or alkyl which can be substituted by hydroxyl, amino, hydrogen sulfide, alkylthio, carboxyl, carbamoyl, guanidinyl, phenyl, hydroxyphenyl, imidazolyl or indolyl radicals or together with R9 is bonded via an alkylene chain to give a ring;
R16 is alkyl, alkenyl or alkynyl;
m is 0 or 1;
n is 0, 1, 2 or 3;

where substituted phenyl, substituted phenoxy, substituted phenylthio or substituted phenylsulfonyl means that the phenyl ring can carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, phenyl, phenyl substituted by one to three halogen atoms or one to three methyl groups, phenoxy, phenoxy substituted by one to three halogen atoms or one to three methyl groups or, on two adjacent atoms, a unit -O-(CH2)o-O-, it being possible for o to assume the values 1 or 2.

2. A process for preparing the compounds of the formula I as claimed in claim 1, which comprises reacting an appropriate derivative of the formula A-XH

where A and X have the meaning indicated above, in a manner known per se with a heterocycle of the formula II

(II) where R17 is a nucleofugic leaving group, in the presence of an inorganic or organic base.

3. A process for preparing the compounds of the formula I as claimed in claim 1, which comprises first converting compounds of the formula I where W is oxygen and R1 is a hydroxyl group to the halide or another activated form of the carboxylic acid in a manner known per se and then reacting these with a nucleophile, if appropriate in the presence of an inorganic or organic base or in the presence of a dehydrating agent.

4. An intermediate of the formula II

(II) where X, Z and R17 have the meanings indicated above.

5. A herbicidal composition comprising a compound of the formula I as claimed in claim 1.
6. A herbicidal composition as claimed in claim 5, comprising further active constituents.
7. A process for controlling undesired plant growth, which comprises treating the undesired plants and/or their habitat with a herbicidally effective amount of a pyrimidine of the formula I as claimed in claim 1.
8. The use of pyrimidines of the formula I as claimed in claim 1 as herbicides.
9. A composition for affecting plant growth, comprising a pyrimidine of the formula I as claimed in claim 1.
10. A process for regulating plant growth, which comprises allowing an amount of a pyrimidine of the general formula I
as claimed in claim 1 which has a regulatory effect to act on the seeds, plants and/or their habitat.
11. A fungicidal and/or nitrification-inhibiting composition comprising a pyrimidine of the formula I as claimed in claim 1.
CA 2166754 1995-01-09 1996-01-08 Fluorinated pyrimidines as herbicides Abandoned CA2166754A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19500379.9 1995-01-09
DE1995100379 DE19500379A1 (en) 1995-01-09 1995-01-09 Fluorinated pyrimidines as herbicides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU551329A1 (en) * 1975-01-20 1977-03-25 Киевский научно-исследовательский институт фармакологии и токсикологии Method for preparing 2-hydroxy-4-amino-substituted pyrimidine
EP0069703B1 (en) * 1981-07-07 1986-04-23 Ciba-Geigy Ag Reactive dyestuffs, their preparation and their use
US4626590A (en) * 1983-11-22 1986-12-02 Mitsubishi Chemical Industries Limited Reactive monoazo and disazo pyridone dyestuffs containing a halo-substituted 6-member nitrogen-containing heterocyclic ring
DE3402194A1 (en) * 1984-01-24 1985-07-25 Bayer Ag, 5090 Leverkusen METHOD FOR SELECTIVE HYDRATION OF CHLORINE-CONTAINING PYRIMIDINS AND NEW PYRIMIDINS
JPH0651684B2 (en) * 1985-10-15 1994-07-06 クミアイ化学工業株式会社 Pyrimidine derivatives and herbicides
AU587539B2 (en) * 1986-06-14 1989-08-17 Ihara Chemical Industry Co. Ltd. Picolinic acid derivatives and herbicidal compositions
JPH01261306A (en) * 1988-04-13 1989-10-18 Nippon Kayaku Co Ltd Flowering promoter comprising 2-alkylthio-4-aminopyrimidine derivative as active ingredient
DE3919435A1 (en) * 1989-06-14 1990-12-20 Basf Ag SALICYLALDEHYDE AND SALICYLSAEED DERIVATIVES AND THEIR SULFUR ANALOGUE, PROCESS FOR THEIR MANUFACTURE AS HERBICIDES AND BIOREGULATORS
GB9002375D0 (en) * 1990-02-02 1990-04-04 Pfizer Ltd Triazole antifungal agents
JP3743059B2 (en) * 1996-06-28 2006-02-08 松下電器産業株式会社 Direct conversion receiver

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