WO2000063182A2

WO2000063182A2 - 2,4-diamino-pyrimidine derivatives and their use as microbicides and herbicides

Info

Publication number: WO2000063182A2
Application number: PCT/EP2000/003158
Authority: WO
Inventors: Stefan Lehr; Hans-Jochem Riebel; Astrid Mauler-Machnik; Karl-Heinz Kuck; Mark Wilhelm Drewes; Ingo Wetcholowsky
Original assignee: Bayer Aktiengesellschaft
Priority date: 1999-04-20
Filing date: 2000-04-10
Publication date: 2000-10-26
Also published as: DE19917785A1; WO2000063182A3; AU3819200A

Abstract

The invention relates to novel 2,4-diamino-pyrimidine derivatives of the formula (I), in which R<1>, R<2>, R<3>, R<4>, R<5> and R<6> have the meanings defined in the description. The invention also relates to their acid addition salts and metal salt complexes and to several methods for producing said novel substances and to their use as microbicides and herbicides. Also disclosed are novel intermediates of the formulae (IIa) and (IIb), wherein R<1>, R<5>, R<6>, X and Z have the meanings defined in the description, and to methods for producing them.

Description

2,4-Diammopyrimidine derivatives

The present invention relates to new 2,4-diamino-pyrimidine derivatives, several processes for their preparation and their use as microbicides and

Herbicides.

It has already become known that numerous substituted 2,4-diamino-pyrimidines have herbicidal and in some cases also microbicidal properties (cf. JP-A 68 563-1991, JP-A 227 978-1991 and DE-A 3 717 480 ). For example, 2-amino

Use 4-benzylamino-6-trifluoromethyl-pyrimidine both to control unwanted microorganisms and weeds. However, the effectiveness of this substance is not always satisfactory, especially at low application rates.

There have now been new 2,4-diamino-pyrimidine derivatives of the formula

in which

R ^{1 represents} trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfinyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl,

R ^{2 represents} halogen, cyano or nitro, R ^{3 represents} hydrogen, alkyl, hydroxy, alkoxy, amino, alkylamino, dialkylamino, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl,

R ⁴ for optionally substituted cycloalkyl, optionally substituted

Aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl, and

R ⁵ and R ⁶ independently of one another are hydrogen, alkyl, methylsulfonyl, acetyl,

Carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl or

R ⁵ and R ⁶ together represent an alkylene chain having 4 to 6 carbon atoms or a - (CH2) ₂ -O- (CH ₂ ) ₂ group

or

R ¹ for trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfonyl, cyano,

Chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl,

R ^{2 represents} hydrogen,

R ^{3 represents} hydrogen, alkyl, hydroxy, alkoxy, amino, alkylamino, dialkylamino, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl,

R ⁴ for optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted Aryloxyalkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl,

R ^{5 represents} hydrogen and

R ^{6 represents} methylsulfonyl or trifluoromethylcarbonyl,

as well as their acid addition salts and metal salt complexes.

It has also been found that 2,4-diamino-pyrimidine derivatives of the formula (I) and their acid addition salts and metal salt complexes can be prepared by:

a) 4-Halogen-2-aminopyrimidines of the formula

in which

R ¹ , R ² , R ⁵ and R ^{6 have} the meanings given above and

X represents chlorine or bromine,

with amines of the formula

R ^J

/

HN (III) in which

R ³ and R ^{4 have} the meanings given above,

if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,

or

b) 2,4-diamino-pyrimidine derivatives of the formula

in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

either

α) with halogen compounds of the formula

R ⁷ -Cl (IV) in which

R ^{7 represents} alkyl, acetyl, trifluoromethylcarbonyl, methylsulfonyl or alkoxycarbonyl, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,

or

ß) with acid anhydrides of the formula

O O

₈ HN

R -C— O— C-R

(N) in which

R ^{8 represents} methyl or trifluoromethyl,

or

γ) with isocyanates of the formula

R ⁹ -Ν = C = O (VI) in which

R ^{9 represents} alkyl,

if appropriate in the presence of a diluent,

or

δ) with carbamic acid ethyl ester of the formula

if appropriate in the presence of a diluent,

or

2,4-diamino-pyrimidine derivatives of the formula

in which

R ¹ , R ² , R ⁴ , R ⁵ and R ^{6 have} the meanings given above,

either

α) with halogen compounds of the formula

R ⁷ -Cl (IV) in which

R ^{7 represents} alkyl, acetyl, trifluoromethylcarbonyl, methylsulfonyl or alkoxycarbonyl,

if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or

ß) with acid anhydrides of the formula

O O

, 11 II 8

R -C—O— CR ⁸

(V) in which

R ^{8 represents} methyl or trifluoromethyl,

or

γ) with isocyanates of the formula

R -N = C = O (VI) in which

R ^{9 represents} alkyl,

if appropriate in the presence of a diluent,

or

δ) with carbamic acid ethyl ester of the formula

if appropriate in the presence of a diluent,

and optionally subsequent to the compounds of formula (I)

Acid or a metal salt added.

Finally, it was found that the 2,4-diamino-pyrimidine derivatives of the formula (I) and their acid addition salts and metal salt complexes are very good for combating undesired microorganisms and also as

Herbicides can be used.

Surprisingly, the 2,4-diamino-pyrimidine derivatives of the formula (I) and their acid addition salts and metal salt complexes according to the invention show a substantially better microbicidal and herbicidal activity than the structurally most similar, known substances of the same action. For example, they outperform 2-amino-4-benzylamino-6-trifluoromethyl-pyrimidine in terms of microbicidal, especially fungicidal, properties.

Formula (I) provides a general definition of the 2,4-diaminopyrimide derivatives according to the invention.

Compounds of the formula (I) in which

R ¹ for trifluoromethyl, difluoromethyl, chloro-difluoromethyl, methyl, methoxy,

Trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfinyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part,

R ^{2 represents} fluorine, chlorine, bromine, cyano or nitro, R ^{3 represents} hydrogen, alkyl having 1 to 4 carbon atoms, hydroxy, alkoxy having 1 to 4 carbon atoms, amino, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group, aminocarbonyl, alkylaminocarbonyl with 1 to

4 carbon atoms in the alkyl part or represents trifluoromethylcarbonyl,

R ^{4 represents} cycloalkyl having 3 to 8 carbon atoms, where each of these radicals can be substituted once to three times, identically or differently by

Halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4

Carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4

Carbon atoms, haloalkoxy having 1 to 4 carbon atoms and 1 to

5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenyl or naphthyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms , Haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro,

Phenyl and / or phenoxy, or

R ^{4 represents} phenylalkyl or naphthylalkyl, each having 1 to 4 carbon atoms in the alkyl part, it being possible for the aromatic ring to be substituted once to three times, in the same way or differently, by halogen or alkyl

1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or R ^{4 represents} phenoxyalkyl or naphthoxyalkyl, each having 1 to 4 carbon atoms in the alkyl part, it being possible for the aromatic ring to be substituted once to three times, in the same way or differently, by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} five- or six-membered heteroaryl with 1 to 3 heteroatoms, such as nitrogen, sulfur and / or oxygen, where each heterocycle can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} five- or six-membered heteroarylalkyl having 1 to 3 heteroatoms, such as nitrogen, sulfur and / or oxygen, in the heteroaryl part and 1 to 4 carbon atoms in the alkyl part, where each heterocycle can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, and

R ⁵ and R ⁶ independently of one another represent hydrogen, alkyl having 1 to 4 carbon atoms, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, aminocarbonyl, alkylaminocarbonyl having 1 to 4 carbon atoms in the alkyl part or trifluoromethylcarbonyl or R ⁵ and R ⁶ together represent an alkylene chain with 4 or 5 carbon atoms or a - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ group.

Compounds of the formula (I) in which

R ^{1 represents} trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfmyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part,

R ^{2 represents} hydrogen,

R ^{3 represents} hydrogen, alkyl having 1 to 4 carbon atoms, hydroxy, alkoxy having 1 to 4 carbon atoms, amino, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group,

Methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy group, aminocarbonyl, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part or for trifluoromethylcarbonyl,

R ^{4 represents} cycloalkyl having 3 to 8 carbon atoms, each of these radicals being monosubstituted to triple, identical or differently substituted by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 up to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenyl or naphthyl, where each of these radicals can be monosubstituted to trisubstituted, identical or different, by halogen or alkyl

1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, halogen alkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenylalkyl or naphthylalkyl each having 1 to 4 carbon atoms in the alkyl part, where the aromatic ring can in each case be substituted once to three times, in the same way or differently, by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenoxyalkyl or naphthoxyalkyl each having 1 to 4 carbon atoms in the alkyl part, where the aromatic ring can in each case be substituted once to three times, in the same way or differently, by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and

1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy, or

R ⁴ for five- or six-membered heteroaryl with 1 to 3 heteroatoms, such as

Nitrogen, sulfur and / or oxygen, where each heterocycle can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, haloalkoxy 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or

Phenoxy, or

R ⁴ for five- or six-membered heteroarylalkyl having 1 to 3 heteroatoms, such as

Nitrogen, sulfur and / or oxygen, in the heteroaryl part and 1 to 4 carbon atoms in the alkyl part, where each heterocycle can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms. atoms, haloalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, phenyl and / or phenoxy,

R ^{5 represents} hydrogen and

R ^{6 represents} methylsulfonyl or trifluoromethylcarbonyl.

2,4-Diaminopyrimidine derivatives of the formula (I) in which

R ^{1 represents} trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfonyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl, methoxycarbonyl or ethoxycarbonyl,

R ^{2 represents} fluorine, chlorine, bromine, cyano or nitro,

R ³ for hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec.-butyl, tert.-butyl, hydroxy, methoxy, ethoxy, amino, methylamino,

Ethylamino, dimethylamino, diethylamino, methylsulfonyl, acetyl,

Carboxyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl or trifluoromethylcarbonyl,

R ^{4 represents} cycloalkyl having 3 to 7 carbon atoms, each of these radicals being monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or R ^{4 represents} phenyl or naphthyl, where each of these radicals can be substituted once to three times, identically or differently, by fluorine, chlorine, bromine,

Methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl,

Trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenylalkyl or naphthylalkyl each having 1 to 4 carbon atoms in the alkyl part, where the aromatic ring can in each case be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n- Butyl, iso-butyl, sec-butyl, tert-butyl,

R ^{4 represents} phenoxyalkyl or naphthoxyalkyl each having 1 to 4 carbon atoms in the alkyl part, where the aromatic ring can in each case be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n- Butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} pyrrolyl, pyrazolyl, pyridyl, pyrimidinyl, imidazolyl, triazolyl, thiazolyl, thiadiazolyl, thienyl or furyl, it being possible for these radicals to be substituted once or twice, in the same or different manner, by fluorine, chlorine, bromine, methyl, ethyl, n- Propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl,

Methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} pyrrolylalkyl, pyrazolylalkyl, pyridylalkyl, pyrimidinylalkyl, imidazolylalkyl, triazolylalkyl, thiazolylalkyl, thiadiazolylalkyl, thienylalkyl or furylalkyl each having 1 to 4 carbon atoms in the alkyl part, the heterocycle in each case being single or double, identical or different can be substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec. -Butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, and

R ⁵ and R ⁶ independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methylsulfonyl, acetyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, Methylaminocarbonyl, ethylaminocarbonyl or trifluoromethylcarbonyl are or

R ⁵ and R ⁶ together represent an alkylene chain with 4 or 5 carbon atoms or a - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ group.

2,4-Diamino-pyrimidine derivatives of the formula (I) in which

R ^{1 represents} trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfinyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl, methoxycarbonyl or ethoxycarbonyl,

R ^{2 represents} hydrogen,

Ethylamino, dimethyla ino, diethylamino, methylsulfonyl, acetyl,

R ^{4 represents} cycloalkyl having 3 to 7 carbon atoms, where each of these radicals can be substituted once to three times, identically or differently by Fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenyl or naphthyl, where each of these radicals can be monosubstituted to triple, identical or differently substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.- Butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenylalkyl or naphthylalkyl each having 1 to 4 carbon atoms in the alkyl part, where the aromatic ring can in each case be substituted one to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n- Butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{4 represents} phenoxyalkyl or naphthoxyalkyl, each having 1 to 4 carbon atoms in the alkyl part, it being possible for the aromatic ring to be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine,

Methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ⁴ for pyrrolyl, pyrazolyl, pyridyl, pyrimidinyl, imidazolyl, triazolyl,

Thiazolyl, thiadiazolyl, thienyl or furyl, where these radicals can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec.- Butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or R ^{4 stands} for pyrrolylalkyl, pyrazolylalkyl, pyridylalkyl, pyrimidinylalkyl, imidazolylal yl, triazolylalkyl, thiazolylalkyl, thiadiazolylalkyl, thienylalkyl or for furylalkyl each having 1 to 4 carbon atoms in the alkyl part, where the heterocycle can be substituted once or twice, in the same way or differently by fluorine, chlorine, bromine, methyl, ethyl, n-propyl,

Isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy,

R ^{5 represents} hydrogen and

R ^{6 represents} methylsulfonyl or trifluoromethylcarbonyl.

A very particularly preferred group of substances according to the invention are 2,4-diaminopyrimidine derivatives of the formula

in which

R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} the meanings given above as being particularly preferred.

Another group of very particularly preferred substances according to the invention are 2,4-diamino-pyrimidine derivatives of the formula

in which

R ³ , R ⁴ and R ^{5 have} the meanings given above as being particularly preferred.

in which

R ⁴ and R ^{5 have} the meanings given above as being particularly preferred.

Finally, another group of very particularly preferred substances according to the invention are 2,4-diamino-pyrimidine derivatives of the formula

in which R ⁵ for hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, methylsulfonyl, acetyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl or for Trifluoromethylcarbonyl,

R ^{10 represents} phenyl, naphthyl, phenoxy or naphthoxy, where each of these radicals can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl , sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, or

R ^{10 represents} pyrrolyl, pyrazolyl, pyridyl, pyrimidinyl, imidazolyl, triazolyl, thiazolyl, thiadiazolyl, thienyl or furyl, these radicals being able to be substituted once or twice, in the same or different manner, by fluorine, chlorine, bromine, methyl, ethyl, n- Propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, nitro, phenyl and / or phenoxy, and

n stands for the numbers 0, 1 or 2.

The specified substituent definitions can be combined with one another as desired. In addition, individual substituent definitions can also be omitted.

The 2,4-diamino-pyrimidine derivatives of the formula (If) contain an asymmetrically substituted carbon atom. They can therefore be in the form of optically active compounds or as mixtures thereof.

Preferred substances according to the invention are also addition products of acids and those 2,4-diamino-pyrimidine derivatives of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} those meanings which have been mentioned as preferred for these radicals.

The acids that can be added preferably include hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, sulfuric acid, nitric acid, acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids, e.g. p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid, saccharin and thiosaccharin.

Preferred substances according to the invention are also addition products from salts of metals of the II. To IV. Main and of I. and II. And IV. To VIII. Subgroup of the periodic table of the elements and those 2,4-diamino-pyrimidine derivatives of the formula (I) in which R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 are} those

Have meanings which have been mentioned as preferred for these radicals.

Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred. Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products. Particularly preferred such acids in this connection are the hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.

If 4,5-dichloro-6-trifluoromethyl-2-aminopyrimidine and 1-phenyl-ethylamine are used as starting materials, the course of process (a) according to the invention can be illustrated by the following formula.

If 5-chloro-6-trifluoromethyl-2-amino-4- (1-phenyl-1-ethyl lamino) pyrimidine and acetyl chloride are used as starting materials, the course of the process according to the invention (b, variant α) can be illustrated by the following formula are illustrated.

If 5-chloro-6-trifluoromethyl-2-amino-4- (1-phenyl-1-ethylamino) pyrimidine and trifluoroacetic anhydride are used as starting materials, the course can of the inventive method (b, variant ß) are illustrated by the following formula.

If 5-chloro-6-trifluoromethyl l-2-amino-4- (1-phenyl-1-ethyl lamino) pyrimidine and methyl isocyanate are used as starting materials, the course of the process (b, variant γ) can be carried out by the following Formula scheme can be illustrated.

If 5-chloro-6-trifluoromethyl-2-amino-4- (1-phenyl-4-ethylamino) pyrimidine and carbamic acid ethyl ester are used as starting materials, the course of the process (b, variant δ) can be followed by the following formula scheme can be illustrated.

If 5-chloro-6-trifluoromethyl-2-dimethylamino-4- (1-phenyl-1-ethylamino) pyrimidine and acetyl chloride are used as starting materials, the course of the process according to the invention (c, variant α) can be carried out by the following Formula scheme can be illustrated.

If 5-chloro-6-trifluoromethyl-2-dimethylamino-4- (1-phenyl-1-ethylamino) pyrimidine and trifluoroacetic anhydride are used as starting materials, the course of the process according to the invention (c, variant β) can be carried out by the following Formula scheme can be illustrated.

If 5-chloro-6-trifluoromethyl-2-dimethylamino-4- (1-phenyl-1-ethyl-amino) -pyrimidine and methyl isocyanate are used as starting materials, the course of the process according to the invention (c, variant γ) can be carried out by the following Formula scheme can be illustrated.

If 5-chloro-6-trifluoromethyl-2-dimethylamino-4- (1-phenyl-1-ethylamino) pyrimidine and ethyl carbamic acid are used as starting materials, the course of the process according to the invention (c, variant δ) can be followed the following

Formula scheme can be illustrated.

Formula (II) provides a general definition of the 4-halo-2-aminopyrimidines required as starting materials when carrying out process (a) according to the invention. In this formula, R ¹ , R ² , R ⁵ and R ⁶ preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention. X also preferably represents chlorine or bromine.

Some of the 4-halo-2-aminopyrimidines of the formula (II) are known (cf. J.

Het. Chem. 20, 219 (1983), JP-A 68 563-1991, JP-A 227 978-1991 and DE-A 3 717 480).

4-Halogen-2-aminopyrimides of the formula are new

in which

R ¹ , R ⁵ , R ⁶ and X have the meanings given above and

Z represents chlorine or bromine.

The 4-halo-2-aminopyrimidines of the formula (Ila) can be prepared by

d) 4-hydroxy-pyrimidine derivatives of the formula

in which

R ¹ , R ⁵ , R ⁶ and Z have the meanings given above,

with phosphorus oxyhalides of the formula

O = PX ₃ (IX)

in which

X has the meaning given above,

optionally in the presence of a diluent and optionally in

In the presence of an acid binder. Formula (VIII) provides a general definition of the 4-hydroxy-pyrimidine derivatives required as starting materials when carrying out process (d). In this formula, R ¹ , R ⁵ and R ⁶ preferably have those meanings which already in connection with the description of the substances of the invention

Formula (I) for these radicals have been mentioned as preferred. Z also preferably represents chlorine or bromine.

The 4-hydroxy-pyrimidine derivatives of the formula (VIII) are new. They can be made by

e) pyrimidine derivatives of the formula

in which

R ¹ , R ⁵ and R ^{6 have} the meanings given above,

with chlorine or bromine, optionally in the presence of a diluent.

Formula (X) provides a general definition of the pyrimidine derivatives required as starting materials when carrying out process (e). In this formula, R ¹ , R ⁵ and R ⁶ preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention. The pyrimidine derivatives of the formula (X) are known or can be prepared by known methods (cf. J. Het. Chem. 20, 219 (1983)).

Suitable diluents for carrying out process (e) are all organic solvents customary for such reactions. Halogenated hydrocarbons, such as methylene chloride, chloroform and carbon tetrachloride, or aliphatic carboxylic acids, such as acetic acid, are preferably usable.

When carrying out process (e), the reaction temperatures can be varied within a certain range. Generally one works at

Temperatures between 0 ° C and 50 ° C, preferably between 5 ° C and 40 ° C.

When carrying out process (e), as in carrying out processes (a) to (d), the process is preferably carried out under atmospheric pressure.

When carrying out process (e), an equivalent amount or an excess of chlorine or bromine is generally employed per mol of pyrimidine derivative of the formula (X). The processing takes place according to usual methods. In general, the reaction mixture is made alkaline by adding base, added to water, the solid obtained is filtered off with suction, the filtrate is extracted with an water-immiscible organic solvent, and the combined organic phases are dried and concentrated.

Formula (IX) defines the phosphorus oxyhalides required as reaction components when carrying out process (d). It is the

Compounds phosphorus oxychloride and phosphorus oxybromide.

Suitable diluents for carrying out process (d) are all solvents customary for such reactions. However, it is also possible to work in the absence of additional diluents. Suitable acid binders for carrying out process (d) are all customary inorganic or organic bases. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, can preferably be used ,

Potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N , N-dimethylbenzylamine, pyridine, N-methylpiperidine,

N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out process (d). Generally one works at

Temperatures between 0 ° C and 120 ° C, preferably between 10 ° C and 100 ° C.

When carrying out process (d), an equivalent amount or an excess of phosphorus oxyhalide of the formula (IX) and an approximately equivalent amount of acid binder are generally employed per mole of 4-hydroxypyrimidine derivative of the formula (VIII) . The processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is concentrated under reduced pressure, the remainder is poured into ice water, the solid which is obtained is filtered off with suction, washed and dried. The product obtained can be freed of any impurities that may still be present using customary methods.

Formula (III) provides a general definition of the amines required as reaction components when carrying out process (a) according to the invention. In this formula, R ³ and R ⁴ preferably have those meanings which have already in connection with the description of the substances of the formula (I) according to the invention for these radicals have been mentioned as preferred.

The amines of the formula (III) are known or can be prepared by known methods.

Suitable acid binders for carrying out process (a) according to the invention are all customary inorganic and organic bases. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, are preferably usable. Sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, further

Ammonium hydroxide, ammonium acetate or ammonium carbonate, or tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-

Dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin can preferably be used; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ether like

Diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane. When carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 130 ° C.

When carrying out process (a) according to the invention, an equivalent amount or an excess of amine of the formula (III) and an equivalent amount are generally employed per mol of 4-halo-2-aminopyrimidine of the formula (II) Acid binder. The processing takes place according to usual methods.

In general, the reaction mixture is concentrated, the remaining residue is stirred with water, the solid formed is filtered off with suction, washed and freed from any impurities which may still be present by customary methods, such as recrystallization and / or chromatography.

Formula (Ia) generally defines the 2,4-diamino-pyrimidine derivatives required as starting materials when carrying out process (b) according to the invention. In this formula, R ¹ , R ² , R ³ and R ⁴ preferably have those meanings which have already been mentioned for these radicals in connection with the description of the substances of the formula (I) according to the invention.

The 2,4-diamino-pyrimidine derivatives of the formula (Ia) are substances according to the invention which can be prepared by process (a) according to the invention.

Formula (IV) provides a general definition of the halogen compounds required as reaction components when carrying out process (b, variant α) according to the invention. In this formula it says R ⁷ preferably for alkyl having 1 to 4 carbon atoms, acetyl, trifluoromethylcarbonyl, methylsulfonyl or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part,

R ⁷ particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, acetyl, trifluoromethylcarbonyl, methylsulfonyl, methoxycarbonyl or ethoxycarbonyl.

The halogen compounds of the formula (IV) are known or can be prepared by known processes.

All customary inorganic and organic bases are suitable as acid binders when carrying out process (b, variant α). All those acid binders which have already been mentioned as preferred in connection with carrying out process (a) according to the invention can preferably be used.

Suitable diluents for carrying out the process (b, variant α) are all customary inert organic solvents. All those solvents which have already been mentioned as preferred in connection with the description of process (a) according to the invention can preferably be used.

The reaction temperatures can also be varied within a certain range when carrying out the process according to the invention (b, variant α). In general, temperatures between 0 ° C and 100 ° C, preferably between 10 ° C and 80 ° C.

When carrying out process (b, variant α) according to the invention, an equivalent amount or an excess of halogen compound of the formula is generally employed per mol of 2,4-diamino-pyrimidine derivative of the formula (Ia) (IV) and an equivalent amount or an excess of acid binder. The processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is diluted with water, the organic phase is separated off, washed, dried and concentrated under reduced pressure. However, it is also possible to first concentrate the reaction mixture, then to add a water-immiscible organic solvent, to wash the resulting organic phase and, after drying, to concentrate under reduced pressure. If necessary, the resulting product can be freed of any impurities that may still be present, using customary methods.

Formula (V) defines the acid anhydrides required as reaction components when carrying out process (b, variant β) according to the invention. The compounds in question are known.

Suitable acid binders when carrying out process (b, variant β) according to the invention are all inorganic and organic bases customary for such reactions.

Suitable diluents for carrying out the process according to the invention (b, variant β) are all inert organic solvents which are customary for such reactions.

The reaction temperatures can also be varied within a certain range when carrying out the process (b, variant β). In general, temperatures between 0 ° C and 100 ° C, preferably between 10 ° C and 80 ° C.

When carrying out process (b, variant β) according to the invention, 1 to 4 mol of acid anhydride of the formula (V) and an equivalent amount or are generally employed per mol of 2,4-diamino-pyrimidine derivative of the formula (Ia) also an excess of acid binder. The processing takes place according to usual Methods. In general, the reaction mixture is concentrated, water is added, the mixture is then extracted with an organic solvent which is not very miscible with water, and the combined organic phases are concentrated after drying under reduced pressure. The resulting product can, if necessary, be freed from impurities still adhering by customary methods.

Formula (VI) provides a general definition of the isocyanates required as reaction components when carrying out process (b, variant γ). In this formula, R ⁹ preferably represents alkyl having 1 to 4 carbon atoms, particularly preferably methyl or ethyl.

The isocyanates of the formula (VI) are known.

Suitable diluents for carrying out the process (b, variant γ) are all inert organic solvents which are customary for such reactions.

The reaction temperatures can also be varied within a certain range when carrying out the process (b, variant γ). In general, temperatures between 0 ° C and 80 ° C, preferably between 10 ° C and 60 ° C.

When carrying out process (b, variant γ) according to the invention, an equivalent amount or an excess of isocyanate of the formula (VI) is generally employed per mol of 2,4-diamino-pyrimidine derivative of the formula (Ia). The

Refurbishment is carried out using customary methods.

The carbamic acid ethyl ester of the formula (VII) required as reaction component when carrying out the process (b, variant δ) is known. Suitable diluents for carrying out the process (b, variant δ) are all inert organic solvents which are customary for such reactions. Alcohols such as methanol, ethanol, n-propanol or isopropanol can preferably be used.

The reaction temperatures can also be varied within a certain range when carrying out the process (b, variant δ). In general, temperatures between 20 ° C and 100 ° C, preferably between 30 ° C and 90 ° C.

When carrying out process (b, variant δ) according to the invention, 1 mole of 2,4-diamino-pyrimidine derivative of the formula (Ia) is generally an equivalent amount or an excess of ethyl carbamic acid of the formula (VII) on. The processing takes place according to usual methods.

Formula (Ib) provides a general definition of the 2,4-diamino-pyrimidine derivatives required as starting materials when carrying out process (c) according to the invention. In this formula, R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ preferably have those meanings which have already been mentioned for these radicals in connection with the description of the substances of the formula (I) according to the invention.

The 2,4-diamino-pyrimidine derivatives of the formula (Ib) are substances according to the invention which can be prepared by process (a) according to the invention.

When carrying out the process (c) according to the variants (α, β, γ and δ), all those components which have already been mentioned in connection with the description of the process (b) according to the invention serve as reaction components. In addition, when carrying out process (c) according to the variants (α, β, γ and δ), the reaction conditions are also identical to those mentioned in the description of process (b) according to the invention.

The 2,4-diaminopyrimidine derivatives of the formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.

For the preparation of acid addition salts of the compounds of formula (I), preference is given to those acids which have already been mentioned as preferred acids in connection with the description of the acid addition salts according to the invention.

The acid addition salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by disconnecting the

Formula (I) in a suitable inert solvent and adding the acid e.g. Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.

For the preparation of metal salt complexes of the compounds of formula (I), preference is given to those salts of metals which have already been mentioned as preferred metal salts in connection with the description of the metal salt complexes according to the invention.

The metal salt complexes of the compounds of formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for. B. ethanol and adding to compounds of formula (I). You can metal salt complexes in a known manner, for. B. by filtering, isolate and, if necessary, clean by urine crystallization. The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.

Fungicides can be used to control Plasmodiophoromycetes,

Use Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or

Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P. brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (Conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporella he otrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention are particularly suitable for combating cereal diseases, such as Erysiphe, Puccinia and Leptosphaeria species. In addition, the substances according to the invention can be used very well against Pyricularia oryzae on rice.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance. In material protection, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials include non-living ones

Understand materials that have been prepared for use in the art. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms . In the context of the materials to be protected, parts of production plants, for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms. In the context of the present invention, the preferred technical materials are adhesives, glues, papers and cartons, leather, wood, paints,

Cooling lubricants and heat transfer liquids called, particularly preferably wood.

Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

For example, microorganisms of the following genera may be mentioned:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, like Chaetomium globosum,

Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.

The active compounds according to the invention also have a herbicidal activity and can be used as defoliants, desiccants, haulm killers and in particular as

Weed killers are used. Weeds in the broadest sense are all plants that grow in places where they are undesirable.

Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The dosages of the inventive weed control necessary

Active ingredients are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,

Carduus, Sonchus, Solanum, Rorippa, Rotola, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to others

Plants.

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective weed control be used in annual crops.

Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations. These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents Means. In case of using water as

Extenders can, for example, also use organic solvents as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as Butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. The following are suitable as solid carriers: for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silicic acid, aluminum oxide and silicates. Possible solid carriers for granules are: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:

Fungicides: aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole,

Azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,

Binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate,

Buthiobate, calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvon,

Quinomethionate (Quinomethionate), Chlobenthiazon, Chlorfenazol, Chloroneb, Chlo- ropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dodithine, dithianon, dithianon,

Drazoxolon,

Edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,

Fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimidol,

Flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fosetyl

Natrixim, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,

Furconazole-cis, furmecyclox,

Guazatin, hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, imibenconazole, iminoctadine, iminoctadineal besilate, iminoctadine triacetate,

Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovededione,

Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and

Bordeaux mix,

Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,

Metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,

Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamate, Nitrothal-Isopropyl, Nuarimol,

Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin,

Piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,

Propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

Quinconazole, quintozen (PCNB), quinoxyfen, Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,

Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,

Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Triticonazol,

Uniconazole,

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G, OK-8705,

OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß-fluorine -b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1 -ethanol, - (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH- 1,2,4-triazol-1-ethanol,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1 H-1, 2,4-triazol-1-yl) -3-octanone,

(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

{2-Methyl- 1 - [[[1 - (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester

1 - (2,4-dichloφhenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) -oxime,

1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione, l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l- [ (Diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichlorophenyl) -l, 3-dioxolan-2-yl] methyl] -IH-imidazole,

1 - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] - 1H-1, 2,4-triazole,

1 - [1 - [2- [(2,4-Dichloφheny l) methoxy] phenyl] etheny 1] - 1 H-imidazole, l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol ,

2 ', 6'-dibromo-2-methyl-4 ^, -trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide,

2, 2-dichloro-N- [1 - (4-chloro-1-yl) -ethy 1] - 1 -ethy 1-3 -methy 1-cy clopropanecarboxamide, 2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,

2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3, 3-triiod-2-propenyl) -2H-tetrazole, 2 - [(l -methylethyl) sulfonyl] -5- (trichloromethyl) - 1, 3, 4-thiadiazole,

2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4-methoxy-1 H-pyrrolo [2,3-d] pyrimidine - 5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) pentandinitrile, 2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,

2-phenylphenol (OPP),

3, 4-dichloro-1 - [4- (difluoromethoxy) pheny 1] - 1 H-pyrrole-2, 5-dione,

3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3 - (1, 1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile ,

3 - [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -lH-imidazole-l-sulfonamide,

4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine, 8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (1-methylethyl) -3-methyl-4- [(3-methylbenzoyl) -oxy] -2.5 -thiophendicarboxy lat, cis-l- (4-chloro-phenyl) -2- (lH-l, 2,4-triazol-l -yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl ) -phenyl-2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,

Ethyl [(4-chlθφhenyl) azo] cyanoacetate,

Potassium hydrogen carbonate,

Methane tetrathiol sodium salt,

Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexane carboxamide.

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,

N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -1, 4,5,6-tetrahydro-2-pyrimidinamine,

N- (4-hexylphenyl) - 1, 4,5, 6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,

N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,

N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide, N- [3-chloro-4,5-bis- (2-propynyloxy) phenyl] -N ' -methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,

O-methyl-S-phenyl-phenylpropylphosphoramidothioat,

S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, r (3Η) -isobenzofuran] -3'-one,

Bactericides:

Bromopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz,

Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, 4-Bromo-2- (4-chloφhenyl) - 1 - (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3- carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos,

N - [(6-chloro-3-pyridinyl) methyl] -N ^, -cyano-N-methyl-ethanimidamide, chloropyrifos, chlorophyros M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, Cyhexatin, cypermethrin, cyromazine,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon,

Dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate,

Dimethylvinphos, Dioxathion, Disulfoton, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos,

Etrimphos,

Fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,

Fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate,

Fipronil, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,

Lambda cyhalothrin, lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,

Naled, NC 184, Nitenpyram,

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Prome- carb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetroos, Pyri- phllos daphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,

Quinalphos,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin,

Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiacloprid, Thiafenox, Thiametoxam, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin,

Tralomethrin, triarathes, triazophos, triazuron, trichlorfon, triflumuron,

Trimethacarb,

Vamidothione, XMC, xylylcarb, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.

When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the soil, the active compound application rates are generally between 0.1 and

10,000 g / ha, preferably between 1 and 5,000 g / ha.

The agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95% by weight, preferably 10 to 75% by weight. The application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to

1.0% by weight based on the material to be protected.

The effectiveness and the spectrum of activity of the active substances to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to increase the Spectrum of effects or achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.

The preparation and use of active compounds according to the invention are illustrated by the following examples.

Manufacturing examples

example 1

A mixture of 4.8 g (0.02 mol) of 4,5-dichloro-6-trifluoromethyl-2-aminopyrimidine in 80 ml of dioxane is mixed with 2.8 g (0.022 mol) of N, N-diisopropyl- ethylamine and 3.03 g (0.022 mol) of 3-phenyl-1-propylamine were added and the mixture was heated to 60 ° C. for 18 hours with stirring. Then 0.3 g of N, N-diisopropylethylamine and 0.3 g of 3-phenyl-1-propylamine are added and a further 8 are heated

Hours with stirring to 80 ° C. The reaction mixture is then concentrated under reduced pressure and water and a small amount of hydrochloric acid are added. The precipitate is filtered off, washed with water and, after drying, dissolved in diethyl ether. This solution is suctioned off through silica gel and the filtrate is concentrated under reduced pressure. In this way, 4 g (60% of theory) of 5-chloro-6-trifluoromethyl-2-amino-4- (3-phenyl-l-propylamino) pyrimidine are obtained in the form of a solid with a melting point of 106 ° C.

Manufacture of starting substances

16.3 g (0.076 mol) of 5-chloro-6-trifluoromethyl-2-amino-4-hydroxy-pyrimidine are mixed with 78 ml of phosphorus oxychloride and 22 ml of N, N-diethyl-aniline at room temperature with stirring and with cooling. After the addition has ended, the reaction mixture is heated to 90 ° C. with stirring for 1.5 hours. The mixture is then concentrated to a third of the original volume under reduced pressure.

The remaining mixture is slowly stirred into cold water. The resulting solid is filtered off, washed successively once with water and once with n-hexane and then dried. In this way, 13.9 g (78.8% of theory) of 4,5-dichloro-6-trifluoromethyl-2-aminopyrimidine are obtained in the form of a solid with a melting point of 105 ° C.

In a mixture of 11 g (0.06 mol) of 6-trifluoromethyl-2-amino-4-hydroxy-pyrimidine and 45 ml of acetic acid are added with stirring at room temperature and with cooling

4.2 g (0.06 mol) of chlorine gas are introduced so that the temperature of the reaction mixture does not exceed 30 ° C. After the addition is complete, stirring is continued for 2 hours at room temperature. The reaction mixture is then poured into water and made alkaline by adding aqueous ammonia. The resulting solid is suctioned off and dried. The filtrate is extracted three times with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. In this way, a total of 5.2 g (40% of theory) of 5-chloro-6-trifluoromethyl-2-amino-4-hydroxypyrimidine is obtained in the form of a solid substance with a melting point above 260 ° C.

92 g (0.8 mol) of potassium tert-butoxide and then 38.2 g (0.4 mol) of guanidine hydrochloride are added to 320 ml of n-butanol at room temperature with cooling and under an argon atmosphere, with stirring. Then you leave that

Boil the mixture under reflux at a bath temperature of 120 ° C. for 15 minutes, then cool to 60 ° C. and 73.6 g (0.4 mol) of ethyl 4,4,4-trifluoroacetoacetate are quickly added dropwise. The reaction mixture is then heated under reflux for 4 hours and then cooled to room temperature. The precipitate is filtered off and washed with 25 ml of n-butanol. The filtrate is adjusted to pH 5 by adding acetic acid. The resulting solid is suctioned off, stirred once with n-hexane and suctioned off again. The solid product is stirred with cold water, again suction filtered and dried, working under reduced pressure at a bath temperature of 60 ° C. This gives 35 g (49% of theory) of 6-trifluoromethyl-2-amino-4-hydroxypyrimidine in the form of a solid with a melting point of 282 ° C.

Example 2

A mixture of 1.2 g (0.005 mol) of 4,5-dichloro-6-trifluoromethyl-2-aminopyrimidine, 15 ml of dioxane and 0.5 g (0.005 mol) of triethylamine is stirred at room temperature with a solution of 0. 62 g (0.005 mol) of 1-phenylethylamine in 1 ml of dioxane were added. The reaction mixture is stirred at 95 ° C. for 18 hours, then with 0.62 g (0.005 ml) 1-phenylethylamine was added and the mixture was stirred at 95 ° C. for 5 hours. After further adding 1 g (0.01 mol) of triethylamine and 0.62 g (0.005 mol) of 1-phenylethylamine, the mixture is stirred at 95 ° C. for a further 64 hours and then concentrated under reduced pressure. The residue is washed several times with water, then stirred with cyclohexane and suction filtered. The remaining product is chromatographed on silica gel using cyclohexane: acetone = 8: 2 as the eluent. After concentrating the eluate under reduced pressure, 0.85 g (54% of theory) of 5-chloro-6-trifluoromethyl-2-amino-4- (1-phenyl-1-ethylamino) pyrimidine is obtained in the form of a solid substance melting point 118 ° C.

According to the methods given above, the substances of the formula listed in Table 1 below are

manufactured.

Table 1

Table 1 (continued)

Example 19

A mixture of 1.23 g (0.0035 mol) of 5-chloro-6-trifluoromethyl-2-amino-4- [l- (4-chlorophenyl) -l-ethylamino] pyrimidine, 25 ml of methylene chloride , 0.82 g (0.0104 mol)

Pyridine and 0.22 g (0.0018 mol) of dimethylamino-pyridine are mixed at 0 ° C with stirring with 0.32 g (0.0039 mol) of acetyl chloride. After the addition has ended, the reaction mixture is stirred at room temperature for 18 hours. Then 0.08 g of pyridine, 0.02 g of dimethylamino-pyridine and 0.03 g of acetyl chloride are added, and the mixture is stirred for a further 6 hours at room temperature. Water is then added to the reaction mixture. The organic phase is separated off, washed with slightly acidified water (pH 4), dried and concentrated under reduced pressure. The residue is taken up in toluene. The resulting mixture is filtered and concentrated under reduced pressure. This gives 0.9 g (65% of theory) of the compound of the structure given above in the form of a

Solid substance with a melting point of 127 ° C.

Example 20

A mixture of 1.5 g (0.0048 mol) of 6-trifluoromethyl-2-amino-4- (3-phenyl-l-methyl-prop-l-yl-amino) pyrimidine and 4 g (0.0061 mol ) Pyridine is 0.7 g (0.0061 mol) of methanesulfonic acid chloride were added to the temperature and the mixture was then stirred at room temperature for 18 hours. The mixture is then concentrated under reduced pressure, the remaining residue is dissolved in ethyl acetate, the solution is washed with slightly acidified water (pH 4), dried and concentrated under reduced pressure. The remaining residue is chromatographed on silica gel with n-hexane: acetone = 8: 2. After concentrating the eluate, 0.7 g (37% of theory) of the compound of the formula given above is obtained in the form of an oil with a log P value of 3.36.

Example 21

A mixture of 0.75 g (0.0022 mol) of 6-trifluoromethyl-5-chloro-2-amino-4- (3-phenyl-l-methyl-prop-l-yl-amino) pyrimidine, 0.85 g (0.0085 mol) of triethylamine and 15 ml of acetonitrile are added in portions at 0 ° C. while stirring with 0.5 g (0.0024 mol) of trifluoroacetic anhydride. When the addition is complete, the mixture is stirred at room temperature for 18 hours, 0.05 g of trifluoroacetic anhydride and 0.085 g of triethylamine are then added, and the mixture is stirred for a further 6 hours at room temperature. Then 0.085 g of triethylamine and 0.05 g of trifluoroacetic anhydride are again added and the mixture is stirred for another hour at room temperature. The reaction mixture is then concentrated under reduced pressure. The residue is mixed with water and extracted several times with ethyl acetate. The combined organic phases are dried and concentrated under reduced pressure. In this way 0.8 g (92% of theory) of the compound of the structure given above is obtained in the form of an oil with a log P value of 4.74. According to the methods given above, the substances listed in Table 2 below are also of the formula

manufactured.

Table 2

Table 2 (continued)

Table 2 (continued)

") The substance shows a signal at 11.12 ppm in the" H-NMR spectrum (d ₆ -DMSO) for the group -NH-SO ₂ CH ₃

The substances listed in the following examples are also produced by the methods given above.

Example 35

Melting point: 149 ° C

Example 36

Melting point: 139-141 ° C

Examples of use

Example A

Erysiphe test (wheat) / protective

Solvent: 25 parts by weight of N, N-dimethylacetamide emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate.

After the spray coating has dried on, the plants are covered with spores from Erysiphe graminis f.sp. tritici pollinated.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table A

Erysiphe test (wheat) / protective

Example B

Puccinia test (wheat) / protective

Solvent: 25 parts by weight of N, N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table B

Puccinia test (wheat) / protective

Example C

Leptosphaeria nodorum test (wheat) / curative

Solvent: 25 parts by weight of N, N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To test for curative effectiveness, young plants are sprayed with a conidia suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours and are then sprayed with the preparation of active compound in the stated application rate.

The plants are placed in a greenhouse at a temperature of approx. 15 ° C and a relative humidity of approx. 80%.

Active ingredients, application rates and test results come from the following

Table. Table C.

Leptosphaeria nodorum test (wheat) / curative

Example D

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

Active ingredients, application rates and test results come from the following

Table. Table D

Post emergence / greenhouse

Claims

1. 2,4-diamino-pyrimidine derivatives of the formula

in which

R ^{2 represents} halogen, cyano or nitro,

R ^{3 represents} hydrogen, alkyl, hydroxy, alkoxy, amino, alkylamino,

Dialkylamino, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl,

R ^{4 represents} optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl, and

R ⁵ and R ⁶ independently of one another are hydrogen, alkyl, methylsulfonyl,

Acetyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl or R ⁵ and R ⁶ together represent an alkylene chain having 4 to 6 carbon atoms or a - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ group

or

R ^{1 represents} trifluoromethyl, difluoromethyl, chlorofluoromethyl, methyl, methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl,

R ^{2 represents} hydrogen,

R ^{3 represents} hydrogen, alkyl, hydroxy, alkoxy, amino, alkylamino, dialkylamino, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl,

Aminocarbonyl, alkylaminocarbonyl, alkyl or trifluoromethylcarbonyl,

R ^{4 represents} optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryl or optionally substituted heteroarylalkyl,

R ^{5 represents} hydrogen and

R ^{6 represents} methylsulfonyl or trifluoromethylcarbonyl,

as well as their acid addition salts and metal salt complexes. Process for the preparation of 2,4-diamino-pyrimidine derivatives of the formula (I) according to Claim 1 and of their acid addition salts and metal salt complexes, characterized in that

a) 4-Halogen-2-aminopyrimidines of the formula

in which

R ¹ , R ² , R ⁵ and R ^{6 have} the meanings given above and

X represents chlorine or bromine,

with amines of the formula

in which

R ³ and R ^{4 have} the meanings given above,

or 2,4-diamino-pyrimidine derivatives of the formula

in which

R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

either

α) with halogen compounds of the formula

R ⁷ -C1 (IV) in which

or

ß) with acid anhydrides of the formula

in which

R ^{8 represents} methyl or trifluoromethyl,

or

γ) with isocyanates of the formula

R ⁹ -Ν = C = O (VI) in which

R ^{9 represents} alkyl,

if appropriate in the presence of a diluent,

or

δ) with carbamic acid ethyl ester of the formula

if appropriate in the presence of a diluent,

or

2,4-diamino-pyrimidine derivatives of the formula

in which

R ¹ , R ² , R ⁴ , R ⁵ and R ^{6 have} the meanings given above,

either

α) with halogen compounds of the formula

R ⁷ -Cl (IV) in which

or ß) with acid anhydrides of the formula

O O II

R ⁸ XO- CR ⁸

(N) in which

R ^{8 represents} methyl or trifluoromethyl,

or

γ) with isocyanates of the formula

R ⁹ -Ν = C = O (VI) in which

R ^{9 represents} alkyl,

if appropriate in the presence of a diluent,

or

δ) with carbamic acid ethyl ester of the formula

if appropriate in the presence of a diluent,

and optionally then adding an acid or a metal salt to the compounds of the formula (I).

3. Microbicidal and herbicidal compositions, characterized in that they contain at least one 2,4-diamino-pyrimidine derivative of the formula (I) according to

Claim 1 or an acid addition salt or metal salt complex of a 2,4-diaminopyrimidine derivative of the formula (I) in addition to extenders and / or surface-active substances.

4. Use of 2,4-diamino-pyrimidine derivatives of the formula (I) according to

Claim 1 or of their acid addition salts and metal salt complexes as microbicides and herbicides.

5. A method for controlling unwanted microorganisms and weeds, characterized in that 2,4-diamino-pyrimidine derivatives of the formula (I) according to Claim 1 or their acid addition salts or

Metal salt complexes on the microorganisms or weeds and / or their habitat.

6. A process for the preparation of microbicidal and herbicidal compositions, characterized in that 2,4-diamino-pyrimidine derivatives of the formula (I) according to Claim 1 or their acid addition salts or metal salt complexes with extenders and / or surface-active substances mixed.

. 4-halo-2-aminopyrimidines of the formula

in which

R ⁵ and R ⁶ independently of one another represent hydrogen, alkyl, methylsulfonyl, acetyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or trifluoromethylcarbonyl or

R ⁵ and R ⁶ together represent an alkylene chain with 4 to 6 carbon atoms or a - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ group,

X represents chlorine or bromine and

Z represents chlorine or bromine.

8. A process for the preparation of 4-halo-2-amino-pyrimidines of the formula (Ila) according to claim 7, characterized in that

d) 4-hydroxy-pyrimidine derivatives of the formula

in which

R ¹ , R ⁵ , R ⁶ and Z have the meanings given above and

with phosphorus oxyhalides of the formula

O = PX ₃ (IX)

in which

X has the meaning given above,

if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.

9. 4-hydroxypyrimidine derivatives of the formula

in which R ¹ for trifluoromethyl, difluoromethyl, chloro-difluoromethyl, methyl,

Methoxy, trifluoromethoxy, methylthio, trifluoromethylthio, methylsulfinyl, methylsulfonyl, cyano, chlorine, bromine, carboxyl, aminocarbonyl or alkoxycarbonyl,

R ⁵ and R ⁶ together represent an alkylene chain having 4 to 6 carbon atoms or a - (CH ₂ ) ₂ -O- (CH ₂ ) ₂ group and

Z represents chlorine or bromine.

10. A process for the preparation of 4-hydroxy-pyrimidine derivatives of the formula (VIII) according to claim 9, characterized in that

e) pyrimidine derivatives of the formula

in which

R ¹ , R ⁵ and R ^{6 have} the meanings given above, with chlorine or bromine, optionally in the presence of a diluent.