MXPA99008296A - Substituted aminosalicyclic acid amides with fungicidal effect and intermediate products for production thereof - Google Patents

Abstract

The invention relates to new substituted aminosalicyclic acid amides of general formula (I), several methods for their production and their use as fungicides, as well as new intermediate products and several methods for their production.

Description

AMIDAS OF THE ACID AMINOSALICI ICO SUBSTITUTED WITH FUNGICIDE EFFECT AND INTERMEDIATE PRODUCTS FOR ITS OBTAINING.

FIELD OF THE INVENTION The invention relates to new amides of the substituted inosalicylic acid, to various processes for their preparation and to their use as fungicides, as well as to new intermediates and to various processes for their preparation.

DESCRIPTION OF THE PREVIOUS TECHNIQUE Certain substituted amides of acylaminosalicylic acid are already known, such as for example the compounds 3-formamido-salicylanilide and 3- (formylamino) -2-hydroxy-N- (phenyl-methyl) -benzamide (see for example the Biochim. Biophys publications. Acta (1993), 1142 (3), 262-8, J. Med. Chem. (1990), 33 (1), 136-42 or J. Biol. Chem. (1971), 246 (23), 7125-30). However, an effect against the pests of these previously known compounds has not been described up to now.

REF .: 31092 DETAILED DESCRIPTION OF THE INVENTION.

New substituted arnics of the aminosalicylic acid of the general formula (I) have now been found, wherein R "signifies hydrogen, alkyl or alkoxy, Y", Y ", Y", Y "5 and Y" are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or halogenoalkoxy and well Y " or Y means -GZ, where G means one of the following groupings -Q-CQ-, -CQ-Q-, -CQ-Q-CH; -, -CH; -Q-CQ-, -Q-CQ-CH ..-, -Q-CQ-Q-CH; -, -N ---- .5 (0) -, -CH -S (O) -CQ-, -S (0): - CH-, -C (RJ) = N-0-, -C (RJ) = N-0-CH-, -N (R -) -, -CQ-N (R4) -, -N (R ') - CQ-, -Q-CQ -N (R) -, -N = C (R3) -Q-CH.-, -CH2-0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R) -CQ-Q-, -CQ-N (R) -CQ- Q-, -N (R4) -CQ-Q-CH2-, -QC (R3) = N-0-CH-, -N (R4) -C (R3) -0-CH2-C (R3) = N-0-CH _--, -N = NC (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH; -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T-Ar1- or -T-Ar1-Q- / where Ar 1 signifies substituted arylene, heteroarylene, cycloalkylene or heterocycle alkylene (ie a double-linked aliphatic ring, in which one or more carbon atoms are replaced by heteroatoms, ie by atoms other than carbon), n means numbers 0, 1 or 2, Q means oxygen or sulfur, R3 means hydrogen, cyano, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively substituted, and R4 means hydrogen, hydroxy, cyano or means alkyl / alkoxy or cycloalkyl substituted respectively where appropriate, R5 means hydrogen or alkyl and T means a single bond, means oxygen, sulfur -CH2-0-, -CH2-S- or means substituted alkanediyl optionally, Z means alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl substituted respectively, if appropriate.

In the definitions the hydrocarbon chains, such as alkyl, alkylene, alkenyl or alkynyl, even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are respectively straight-chain or branched chain.

In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially fluorine or chlorine.

Aryl means aromatic, mono- or polycyclic hydrocarbon rings, such as for example phenyl, naphthyl, anthranil, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

Heterocycle means saturated or unsaturated ring compounds, as well as aromatic, with up to 8 members in the ring, in which at least one member of the ring is a heteroatom, that is, an atom other than carbon. If the ring contains several heteroatoms, these may be the same or different. Preferred heteroatoms are oxygen, nitrogen or sulfur. If necessary, the ring compounds form a polycyclic ring system together with other carbocyclic or heterocyclic rings, which are over-condensed or bridged. Mono- or bicyclic ring systems are preferred, especially mono- or bicyclic, aromatic ring systems.

Cycloalkyl means saturated, carbocyclic, ring-shaped compounds, which optionally form with other carbocyclic, over-condensed or bridged rings, a polycyclic ring system.

Cycloalkylene means carbocyclic, ring-shaped compounds containing at least one double bond and, if appropriate, form a polycyclic ring system with other carbocyclic, over-condensed or bridged rings.

It has also been found that the new substituted amides of the acylaminosalicylic acid of the general formula (I) are obtained, if a) Aminosalicylic acid amides of the general formula (II) are reacted, wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with acylating agents of the general formula (III) OR R X1 (m) wherein R1 has the meaning indicated above and X1 means halogen, hydroxy, alkoxy or alkylcarbonyloxy, if appropriate in the presence of a diluent, if appropriate in the presence of an acid-binding agent and, if given, in the presence of another agent auxiliary to the reaction, or b) nitrosalicylic acid amides of the general formula (IV) are reacted wherein 1 f? 2 f? 3 r? 4 and Y5 have the meanings given above, with formic acid, if appropriate in the presence of a catalyst and, if appropriate, in the presence of another reaction auxiliary agent, or yes c) O-benzyl-nitrosalicylic acid amides of the general formula (V) are reacted, wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with formic acid, if appropriate in the presence of hydrogen or a non-noble metal, if appropriate in the presence of a catalyst and, if appropriate, in the presence of another agent auxiliary to the reaction.

Finally it has been found that the new substituted amides of the aminosalicylic acid of the general formula (I) show a very potent fungicidal effect.

The compounds according to the invention and their starting materials are optionally also available as mixtures of the various possible isomeric forms, especially of stereoisomers, such as, for example, the E and Z isomers, threo and erythro, as well as optics or also tautomers. HE they claim both the E isomers and the Z isomers, as well as the threo and erythro isomers, as well as the optical isomers, as well as the possible tautomers, and the arbitrary mixtures of these isomers.

In the general formula (I), R 1 preferably denotes hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; especially means hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy; preferably it means hydrogen, methyl or ethyl, especially preferably hydrogen.

In the general formula (I), Y1, Y4 and Y5 preferably represent, independently of one another, hydrogen, halogen, cyano, cycloalkoxy with 1 to 4 carbon atoms, haloalkyl or haloalkoxy with 1 to 4 carbon atoms; especially they mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy; preferably they mean hydrogen.

In the general formula (I), Y2 and Y3 mean, independently of one another, preferably hydrogen, halogen, cyano, alkyl or alkoxy with 1 to 4 carbon atoms, haloalkyl, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and one of the residues Y2 or Y3 means the group -GZ.

Especially Y2 means hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, preferably hydrogen.

Especially Y3 means hydrogen, fluorine, chlorine, bromine, cyano, methyl, methyl, methoxy, trifluoromethyl or difluoromethoxy; preferably it means the group G-Z.

In the general formula (I), G preferably means one of the following groupings. -Q-CQ-, -CQ-Q-, -CQ-Q-CH: -, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH; -, -N = N-, -S (0) r-, -CH: -S (0) n-, -CQ-, -S (0) n -CH2-, -C (R3) = N-0-, -C (R3) = N-0-CH2-, -N (R4) -, -CQ-N (R4) -, -N (R4) -CQ-, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH2-, -CH2-0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R4) -CQ-Q-, -CQ-N (R4) -CQ-Q-, -N (R4) -CQ-Q-CH2-, -Q-C (R3) = N-0-CH2-, -N (R) -C (R3) = N-0-CH2-, -O-CH-C (R3) = N-0-CH _-- -N = NC (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH = -, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T -Ar1- or -T-Ar1-Q-, where Q, n, R3, R4 and R5 have the meanings given in the application Especially G stands for -C (R3) = N-0-CH2-, where R3 preferably denotes cyclopropyl and especially means methyl.

Preferably G means -T-Ar1-, -T-Ar1-S- and especially means -1-? R1-0-, where T preferably means a single bond, means oxygen, sulfur, -CH2-0-, -CH- S-, or means alkanediyl having 1 to 3 carbon atoms, especially means a single bond, means oxygen, sulfur, -CH2-0-, -CH2-S-, methylene, ethylene or propylene and preferably means oxygen.

Preferably Ar1 means phenylene, naphthylene, cycloalkylene, each optionally substituted one or more times, in the same or in different ways or means heteroarylene or heterocycloalkylene with 3 to 7 members in the ring, one of which means oxygen, Sulfur or nitrogen, and optionally one or two more mean nitrogen, the possible substituents being preferably chosen in the following enumeration: halogen, cyano, amino , hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl halogenoalkenyloxy respectively straight-chain or branched chain, with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions, as well as cycloalkyl with 3 to 6 carbon atoms and especially means phenylene or pyridinediyl substituted respectively in case given from one to three times, in the same or in different forms, means pyrimidindiyl, pyridazindiyl, pyrazinyl, 1, 2, 3-triazindyl, 1, 2,4-triazindiyl, or 1, 3, 5-triazindiyl, respectively monosubstituted if appropriate, or means 1,2,4-thiadiazoldiyl, 1,3,4-thiadiazoldiyl, 1,2-oxadiazoldiyl, 1,3,4-oxa-diazoldiyl, the possible substituents being preferably chosen from the following enumeration: fluorine , chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, tinylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and Arl preferably means 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl, or 1, 3, 5-triazindiyl substituted respectively in case given once or twice, in the same or in different ways, the aforementioned substituents being taken into consideration or, particularly preferably, means 1, 2, 4-thiadiazoldiyl or substituted pyrimidinediyl optionally once or twice, the same or in different forms, the above-mentioned substituents being considered and the substituents preferably being halogen, especially fluorine.

In the general formula (I), preferably, z means alkyl with 1 to 8 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen, by cyano, by hydroxy, by amino, by alkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms or for alkylsulfonyl having 1 to 4 carbon atoms (which may be substituted, if appropriate, by halogen, respectively); means alkenyl or alkynyl with respectively up to 8 carbon atoms, respectively substituted, if appropriate, by halogen; means cycloalkyl having from 3 to 6 carbon atoms, each optionally substituted one or more times, in the same or different manner by halogen, by cyano, by carboxy, by phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms), by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl having 1 to 4 carbon atoms; means phenyl, naphthyl respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, at least one of which means oxygen, sulfur or nitrogen and, if appropriate, one or two more mean nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, respectively straight-chain or branched chain, respectively having 1 to 6 carbon atoms; alkenyl or alkenyloxy respectively straight-chain or branched chain, respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain, with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene, with respectively 1 to 6 carbon atoms, respectively double-bonded, respectively substituted, if appropriate, one or more times, in the same or different ways, by halogen and / or by straight-chain or branched-chain alkyl with 1 to 4 carbon atoms and / or by straight-chain or branched-chain halogen with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; phenyl or phenoxy substituted, if appropriate one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl having 1 to 4 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, 1 to 3 of which, respectively, are the same or different heteroatoms, especially nitrogen, oxygen and / or sulfur, or a group wherein A1 means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano, by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl, or by a group wherein A3 means alkyl having 1 to 4 carbon atoms and A4, A5, A6 and A7 are the same or different and independently of each other hydrogen, alkyl or hydroxyalkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or A4 and A5 or A4 and A5 or A6 and A7 form together with the corresponding carbon atoms, with which they are bonded, a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

In the general formula (I), it preferably means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted one to three times, in the same or in different ways by fluorine, by chlorine, by cyano or by methoxy; means vinyl, allyl or propargyl respectively substituted, if appropriate, by fluorine or chlorine; means cyclopropyl, cyclopentyl or cyclohexyl respectively substituted one to three times, in the same or different ways by fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; and preferably, it means phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1, 2, 4-oxadiazolyl, 1,3-oxadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2, 3 -triazinyl, 1,2,4-triazinyl or 1, 3, 5-triazinyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents having the meanings indicated above and preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy methylthio, ethylthio, n- or propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively doubly attached each substituted optionally one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or a grouping where A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2- methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthio ethyl, methylthioethyl, ethylthioethyl, di ethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a grouping wherein A3 means methyl or ethyl and A4, A5, A6 and A7 are the same or different and mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n- i-, s- or t- butyl, hydroxymethyl, trifluoromethyl, or trifluoroethyl, or A4 and A5 or A4 and A5 or A6 and A7 together with the respective carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

In the general formula (I), preferably, it means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted one to three times, in the same or different forms by fluorine, by chlorine, by cyano or by methoxy; means vinyl, allyl or propargyl respectively substituted, if appropriate by fluorine or by chlorine, means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted one to three times, in the same or in different forms by fluorine, by chlorine, by cyano, by methoxy, by phenyl, by methyl or by ethyl; and preferably means phenyl, pyridyl, pyrimidyl or thienyl substituted, if appropriate, one to three times, in the same or in different ways, the possible substituents having the meanings indicated above and preferably chosen from the following list: fluorine, chlorine, bromine , cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl, trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl or phenoxy; Methylenedioxy, ethylendioxy, respectively double-bonded, each optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy or a grouping wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-en-1-yl, 2-methyl- prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a grouping wherein A3 means methyl or ethyl and A4, A5, A6 and A7 are the same or different and mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or A4 and A5 or A4 and A6 or A6 and A7 form, together with the corresponding carbon atoms with which they are bonded, a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

In the general formula (I), particularly preferably, Z means pyridyl, pyrimidyl, respectively substituted one to three times, in the same or different forms, and especially phenyl unsubstituted or substituted one to three times, in the same or in different forms, the possible substituents having the meanings previously indicated and preferably chosen in the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or - propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl or phenoxy.

The subject of the present application are preferably amides of the aminosalicylic acid of the formula (I), in which R 1 denotes hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, Y 1, Y 2, Y 3, Y4 and Y5 are the same or different and mean hydrogen, halogen, cyano, alkyl or alkoxy with respectively 1 to 4 carbon atoms, haloalkyl or haloalkoxy with respectively 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms, and Y2 or Y3 mean -GZ, where G means one of the following groupings -Q-CQ-, -CQ-Q-, -CQ-Q-CH2-, -CH: -Q-CQ-, -Q-CQ-CH; -, -Q-CQ-Q-CH2-, -N = N-, -S (0) n ", -CH2-S (0) n-, -CQ-, -S (0) n-CH2- , -C (R3) = N-0-, -C (R3) = N-0-CH2-, -N (R4) -, -CQ-N (R4) -, -N (R) -CQ-, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH: -, -CH2-0-N = C (R3) -, -C (CH3) -0-N = C ( R3) -, -N (R4) -CQ-Q-, -CQ-N (R4) -CQ-Q-, -N (R4) -CQ-Q-CH2-, -QC (R3) = N-0 -CH2-, -N (R) -C (R3) = N-0-CH2-, -0-CH-C (R3) = N-0-CH2-, -N = N-C (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T -Ar1- or -TA ^ -Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R3 means hydrogen, cyano, means alkyl, alkoxy, alkylthio alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the groups alkyl, respectively substituted, if appropriate, by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or by cycloalkyl having 3 to 6 carbon atoms substituted, if appropriate, by halogen, cyano, carboxy, alkyl 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to carbon atoms and R 4 means hydrogen, hydroxy, cyano or means alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by halogen, cyano by carboxy, alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms, R5 means hydrogen or alkyl having 1 to 4 carbon atoms, Ar_ means phenylene, naphthylene, cycloalkylene, each optionally substituted one or more times, in the same or in different forms or means heteroarylene or heterocycloalkyl ileno with 3 a 7 members in the ring, one of which means at least oxygen, sulfur or nitrogen and if necessary one or two more mean nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; means alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; means alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; means halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms; means halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 same or different halogen atoms; means alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions, as well as cycloalkyl with 3 to 6 carbon atoms and T means a single bond, means oxygen, sulfur, -CH2-0-, -CH2-S- or means alkanediyl with 1 to 3 carbon atoms, Z means alkyl with 1 to 8 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen , by cyano, by hydroxy, by amino, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms ( which may be substituted, if appropriate, by halogen, respectively); means alkenyl or alkynyl with respectively up to 8 carbon atoms, optionally substituted by halogen, means cycloalkyl having 3 to 6 carbon atoms, respectively optionally substituted one or more times, in the same or different forms by halogen, cyano, by carboxy, by phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms), by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms; means phenyl, naphthyl respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, at least one of which means oxygen, sulfur or nitrogen and, if appropriate, one or two more mean nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenalkenyl or halogenoalkenyloxy respectively straight chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 same or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxy-alkylene with respectively 1 to 6 carbon atoms, respectively double-bonded, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 4 carbon atoms and / or straight chain or branched chain halogen with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; phenyl or phenoxy substituted, if appropriate one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl having 1 to 4 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, among which respectively 1 to 3 are identical heteroatoms or different especially nitrogen, oxygen and / or sulfur-, or a grouping wherein A1 means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, respectively, optionally substituted by cyano, by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl or a group where A3 means alkyl with 1 to 4 carbon atoms and A4, A5, A6 and A7 are the same or different and mean, independently of one another, hydrogen, alkyl or hydroxyalkyl with respectively 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms, A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

The present application relates especially to the compounds of the formula (I), in which R 1 is hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy, Y 1, Y 2, Y 3, Y 4 and Y 5 are the same or different and represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy Y2 or Y3 well mean -GZ-, where G represents one of the groupings below -Q-CQ-, -CQ-Q -, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CHz-, -N = N-, -S (0) n ", -CH2-S (0) n-, -CQ-, -S (0) n -CH2-, -C (R3) = N-0-, -C (R3) = N-0-CH2-, -N (R4) -, -CQ-N (R4) -, -N (R4) -CQ-, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH2-, -CH2-0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R4) -CQ-Q-, -CQ-N (R4) -CQ-Q-, -N (R4) -CQ-Q-CH2-, -QC (R3) = N-0-CH-, -N (R4) -C (R3) = N-0-CH2-, -O-CH-C (R3) = N -0-CH-, -N = NC (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH: -, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (-N-0-R5) -C (R3) -0-N = C (CH3) - -T -Ar1- or -T-Ar1-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R3 signifies hydrogen, cyano, methyl, ethyl or cyclopropyl and R4 signifies hydrogen, methyl, ethyl, or cyclopropyl, R5 signifies hydrogen or methyl, Ar1 signifies phenyl or pyridinediyl substituted in each case optionally one to three times, identically or differently, I mean pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3 triazindiilo, 1, 2, 4-I triazindiilo 1, 3, 5-triazindiilo respectively monosubstituted optionally o is 1, 2, 4-thiadiazolediyl, 1, 3, 4-thiadiazolediyl, 1, 2, 4-oxadiazolediyl, 1, 3, 4-oxadiazolediyl, choosing the possible substituents preferably the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i- propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulfonyl and T means a single bond, means oxygen, sulfur, -CH2-0-, -CH2-S-, methylene, ethylene or propylene, Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted one to three times, in the same or different ways by fluorine, by chlorine, by cyano or by methoxy; means vinyl, allyl or propargyl respectively substituted, if appropriate, by fluorine or chlorine; means cyclopropyl, cyclopentyl or cyclohexyl respectively substituted one to three times, in the same or different ways by fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; or Z represents phenyl, 1, 2, 4-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 2, 4-oxadiazolyl, 1, 3, 4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1, 2, 3 -triazinyl, 1, 2, 4-triazinyl or 1, 3, 5-triazinyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoro ethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively doubly attached substituted in each case given one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl , cyclobutyl, cyclopentyl or cyclohexyl, or a grouping wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxy ethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a group where A3 means methyl or ethyl and A4, A5, Ad and A7 are the same or different and mean, independently of one another, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or A4 and A5 or A4 and A6 or A6 and A7, together with the corresponding carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

A particularly preferred group of compounds according to the invention are those compounds of the formula (I), wherein R 1 signifies hydrogen, methyl or methoxy, Y 1, Y 2, Y 3, Y 4 and Y 5 are the same or different and mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, I or Y2 or Y3 mean -GZ, where G means -C (R3) = N-0-CH2-, where R3 signifies methyl or cyclopropyl and Z means phenyl, pyridyl or pyrimidyl respectively substituted one to three times, in the same way or in different ways, choosing the possible substituents preferably from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoro ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl ethoxyiminoethyl, methylenedioxy or ethylenedioxy respectively doubly linked, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl, as well as phenyl and phenoxy.

Also particularly preferred groups of compounds according to the invention are those compounds of the formula (I): in which R 1 signifies hydrogen, methyl or methoxy. Y1, Y2, Y3, Y4 and Y5 are the same or different and mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy. Y2 or Y3 mean -GZ, where G means -T-Ar1- or -T-Ar1-0- where Ar1 means 1, 2,4-thiadiazolidiyl, 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1, 3, 4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl or 1, 3, 5-triazindiil respectively substituted one or two times, in the same or different way by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, T means a single bond, means oxygen, sulfur, -CH2-0-, -CH2-S-, methylene, ethylene or propylene. Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted one to three times, in the same or in different ways, by fluorine, by chlorine, by cyano or methoxy; means vinyl, allyl or propargyl respectively substituted, if appropriate, by fluorine or chlorine; means cyclobutyl, cyclopentyl or cyclohexyl respectively substituted, if appropriate one to three times, in the same or different ways by fluorine, by chlorine, by cyano, by methoxy, by phenyl, by methyl or by ethyl; or means phenyl, pyridyl, pyrimidyl, thienyl, respectively, optionally substituted one to three times, in the same or in different ways, with the possible substituents being chosen, preferably from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively doubly bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy or a group wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-propyl-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, ethylthiomethyl, ethylthiomethyl, methylthioethyl , ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, ethylaminomethyl, methylaminoethyl or benzyl, or a grouping where Av3 means methyl or ethyl and A4, A5, A6 and A7, are the same or different and mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl, or trifluoroethyl, or A4 and A5 or A4 and A6 or A6 and A7 together with the corresponding carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

The definitions of the residues given above in a general manner or in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting materials or for the intermediate products necessary respectively for the obtaining.

The definitions of the residues indicated individually for these residues in the corresponding combinations or in the preferred combinations of the residues will be arbitrarily replaced by the corresponding definitions of the residues of the other preferred ranges, independently of the combination given in each case.

By way of example and preferably, tables 1 to 4 according to the invention are indicated: Table 1 where Z1 means the following substituents: Table 2 (I-b) where Z2 means the following substituents: (Continuation of table 2).

(Continuation of table 2] Table 3 where Z2 means the substituents indicated in table 2.

Table 4 (I-) where Z2 means the substituents indicated in table 2.

The amides of aminosalicylic acid, which are necessary as starting materials, for carrying out process a) according to the invention, are generally defined by means of formula (II). In this formula (II) Y1, Y2, Y3, Y4 and Y5 preferably have or especially those meanings which have already been mentioned as being preferred or especially preferred for Y1, Y2, Y3, Y4 and Y5 in relation to the description of the compounds of the formula (I) according to the invention.

The starting materials of the formula (II) are new and also constitute an object of the present application.

The aminosalicylic acid amides of the formula (II) are obtained if they are reacted (process d) nitrosalicylic acid amides of the general formula (IV), wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with a reducing agent, such as, for example, hydrogen, iron, zinc, tin chloride-II, sodium or ammonium hydrogen sulphide, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst, or if (process e) O-benzyl-nitrosalicylic acid amides of the general formula (V) are reacted, wherein Y1, Y2, Y3, Y4 and Y5 have the meanings given above, with hydrogen, optionally in the presence of a diluent and, if appropriate, in the presence of a catalyst.

The amides of nitrosalicylic acid, which are necessary as starting materials, for carrying out process d) according to the invention are generally defined by means of formula (IV). In this formula (IV), Y1, Y2, Y3, Y4 and? 5 preferably have, or are particularly preferably, those meanings which have already been mentioned in a preferred manner or, more particularly, for Y1, Y2, Y3, Y4 and Y5 in relation to the description of the compounds of the formula (I) according to invention.

The nitrosalicylic acid amides of the formula (IV) are novel and are also an object of the present application.

These are obtained by reacting (process f) 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-nitrobenzoyl chloride with an amine of the formula (VII), wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, optionally in the presence of a diluent, if appropriate, in the presence of a condensing agent, and, if appropriate, in the presence of an acceptor of acid.

It has also been found that the novel nitrosalicylic acid amides of the formula (IV) are suitable for the control of pests in plants and industrial materials, preferably against fungi, insects and bacteria.

The 2-hydroxy-3-nitrobenzoic acid or the 2-hydroxy-3-nitrobenzoyl chloride, which are necessary as starting materials for carrying out process f) according to the invention, are known (see, for example, J. Chem. Soc. ., 1953, 2049, 2050 or US Patent 03527865).

The amines, which are also necessary as starting materials for carrying out process f) according to the invention, are generally defined by means of formula (VII). In this formula (VII), Y1, Y2, Y3, Y4 and Y5 preferably have or especially those meanings that have already been mentioned above, preferably or especially preferably for Y1, Y2, Y3, Y4 and Y5 in relation to with the description of the compounds of the formula (I) according to the invention.

The amines of the formula (VII) are partially known and can be prepared according to procedures known (see for example WO-A 9601825, EP-A 192180).

New and also constitute an object of the present application, the amines of the formula wherein Y6, Y7, Y8, Y9 and Y10 are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy and, Y7 or Y8 mean a grouping -Ar where m means 0 or 1, Ar2 means 1,2,4-oxadiazol-3,5-diyl, 1,2,4-thiadiazol-3,5-diyl or means pyrimidin-4,6-diyl optionally substituted at the 5-position by halogen and + Z3 means aryl, if any, substituted.

Preference is given to amines of the formula (Vil-a), in which Y6, Y7, Y8, Y9 and Y10 are the same or different and denote hydrogen, halogen, cyano, alkyl or alkoxy with 1 to 4 carbon atoms, haloalkyl or halogenalkoxy with 1 to 4 carbon atoms or 1 to 5 same or different halogen atoms, and either Y7 or Y8 mean a grouping where m means 0 or 1, Ar2 means 1,2,4-oxadiazol-3,5-diyl, 1,2,4-thiadiazol-3,5-diyl, or means substituted pyrimidin-4,6-diyl, if appropriate in position 5 by fluorine or by chlorine and means phenyl or naphthyl respectively substituted one or more times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, with respectively 1 to 6 carbon atoms, respectively straight chain or branched chain; alkenyl or alkenyloxy with respectively 2 to 6 carbon atoms, respectively straight-chain or branched chain; haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, respectively straight chain or branched chain; haloalkenyl or haloalkenyloxy with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, respectively straight-chain or branched chain; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy, respectively straight chain or branched chain, with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene, with respectively 1 to 6 carbon atoms, respectively double-bonded, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 6 carbon atoms; to 4 carbon atoms and / or by straight chain or branched chain halogen alkyl with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; phenyl or phenoxy substituted, if appropriate one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl having 1 to 4 carbon atoms; heterocyclyl or heterocyclylmethyl respectively 3 to 7 members in the ring, between which, respectively 1 to 3 are the same or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, or a grouping A- I o where A8 means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A9 means alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano , by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl, or a group wherein A10 means alkyl with 1 to 4 carbon atoms and A11, A12, A13 and A14 are the same or different and independently of each other, hydrogen, alkyl or hydroxyalkyl with respectively 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms, or A11 and A12 or A11 and A13 or A13 and A14 together with the corresponding carbon atoms, with those that are linked form an aliphatic ring with 5, 6 or 7 carbon atoms.

Especially preferred are amines of the formula (VII-a), in which Y6, Y7, Y8, Y9 and Y10 are the same or different and denote hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluormetoxy, well ^ o-Ar-o-; z Y7 or Y8 denote a grouping where m means 0 or 1, Ar2 means 1,2,4-oxadiazol-3,5-diyl, 1,2,4-thiadiazol-3,5-diyl or means pyrimidine-4, β- diyl optionally substituted at position 5 by fluorine or chlorine and means phenyl which is respectively substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following number: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy , difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively double-bonded, substituted or, optionally, one to four times, in the same or in different forms by fluorine, chlorine, methyl, trifluoromethyl or ethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclo utilo, cyclopentyl or cyclohexyl, or a grouping OR Wherein A8 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A9 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl- "LQ prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, di-ethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a group 0 wherein A10 means methyl or 'ethyl and A11 and A12 or A11 and A13 or A13 and A14 are the same or different and they mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or A11 and A12 or A11 and A13 or A13 and A14 together with the corresponding carbon atoms, with which they are bound, they form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

The amines of the formula (Vil-a) are obtained (process h), if diazoles of the general formula (VIII) or halogeno-pyrimidine of the general formula (IX) are reacted, (HIV) (IX) where m means 0 or 1, X2 means hydrogen, fluorine or chlorine, X3 means chlorine or fluorine, X 4 means methylsulfonyl, chlorine or bromine and Q means oxygen or sulfur, and Z 3 has the meaning indicated above, with an aminophenol of the formula, wherein Y11, Y12, Y13, Y14 and Y15 are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy, and either Y12 or Y13 means amino, if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst, or if (process i) reacting aminophenoxypyrimidine of the general formula (XI), wherein X2, Y11, Y12, Y13, Y14 and Y15 have the meanings indicated above and X5 means chloro or fluoro, with a phenol of the general formula (XII), Z -OH (XII) wherein Z3 has the meaning indicated above, if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst.

The. diazoles, necessary as starting materials, for carrying out process h) according to the invention are defined in general by means of formula (VIII). In this formula (VIII), m and Z3 have preferably or especially those meanings which have already been mentioned in a preferred manner or, more preferably, for m and Z3 in relation to the description of the compounds of the formula (VIIa) according to the invention. X4 means methylsulfonyl, chlorine or bromine.

The diazoles of the formula (VIII) are known and can be prepared according to known processes (see for example DE-A 2142913).

The halogenopyrimidines necessary alternatively as starting compounds for carrying out process h) according to the invention are generally defined by means of formula (IX). In this formula (IX), m and Z3 preferably have or especially those meanings which have already been mentioned in a preferred manner or, more preferably, for m and Z3 in relation to the description of the compounds of the formula (VII-a) according to the invention. X2 means hydrogen, fluorine or chlorine. X3 means fluorine or chlorine.

The halogenopyrimidines of the formula (IX) are partially known and can be prepared according to known methods (see for example the publications Pharm. Chem. J. (Engl Transí.), 23, 6, 1989, 500-503; RU, 23, 6, 1989, 705-707).

New, and also an object of the present application, are 4-chloro-5-fluoro-6-phenoxypyrimidines of the general formula wherein Z3 has the above-stated meaning, the compound consisting of methyl 2- [(6-chloro-5-fluorou-4-pyrimidinyl) -oxy] -a- (ethoxymethylene) -benzoate being excluded.

The new 4-chloro-5-fluoro-6-phenoxypyrimidines are obtained and reacted (process j) phenols of the general formula (XII), Z3-OH (XII) wherein Z3 has the meaning indicated above, with 4,6-dichloro-5-fluoropyrimidine (XIII), if appropriate in the presence of a diluent, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a catalyst.

The phenols which are necessary as starting materials for carrying out process j) according to the invention are generally defined by means of formula (XII). In this formula (XII), Z3 preferably has or especially that meaning which has already been preferentially or very preferably indicated for Z3 in relation to the description of the compounds of the formula (VIIa) in accordance with invention.

The phenols of the formula (XII) are chemical products for known syntheses or can be prepared according to known processes (WC 95-04728).

The 4,6-dichloro-5-fluoropyrimidine (XIII), which is also necessary as starting material for carrying out process j) according to the invention, is new and also constitutes an object of the present application.

This is obtained if it is reacted (procedure k) 5-fluoro-6-hydroxy-4 (1H) -pyrimidinone (XIV) with a chlorinating agent, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst.

The 5-fluoro-6-hydroxy-4 (1H) -pyrimidinone (XIV), necessary as a starting material for carrying out process k) according to the invention is known and can be prepared according to known methods (JP 61205262; CA: 106: 84632).

The aminophenoxypyrimidines necessary as starting materials for carrying out process i) according to the invention are generally defined by means of formula (XI). In this formula (XI), Y11, Y12, Y13, Y14 and? 15 preferably have or especially those meanings that have already been mentioned preferably or particularly preferably for Y11, Y12, Y13, Y14 and Y15 in relation to with the description of the amines of the formula (X). X2 and X5 mean, independently of each other, chlorine or fluorine.

The aminophenoxypyrimidines of the formula (XI) are new and also constitute an object of the present application.

These are obtained if they are reacted (process 1) trihalógenopiri idinas of the formula (XV), wherein X2 and X5 have the meanings indicated above and X6 means fluorine or chlorine, with an aminophenol of the formula (X), optionally in the presence of a diluent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst.

The trihalopyrimidines, necessary as starting materials for carrying out the procedure 1) according to the invention are generally defined by means of formula (XV). In this formula (XV) X2 and X5 preferably have or especially those meanings which have already been mentioned in a preferred manner or, more particularly, for X2 and X5 in relation to the description of the compounds of the formula (XI). X6 means fluorine or chlorine.

The trihalopyrimidines of the formula (XV) are partially known and can be prepared according to known methods (see for example Chesterfield et al., J. Chem. Soc., 1955; 3478, 3480). A special case for the compounds of the formula (XV) does not constitute the compound according to the invention (XIII); it can be prepared according to process k).

The aminophenols of the formula (X), which are also necessary as starting materials for carrying out the process 1) according to the invention, have already been described above on the occasion of the description of the process h) according to the invention.

The phenols of the formula (XII), which are also necessary as starting materials for carrying out the process i) according to the invention, have already been described previously on the occasion of the description of process j) according to the invention.

The amides O-benzyl-nitrosalicylic acid necessary as starting materials for carrying out process e) according to the invention, are generally defined by means of formula (V). In this formula (V), Y1, Y2, Y3, Y4 and Y5 preferably have or especially those meanings which have already been mentioned in a preferred manner or, more preferably, for Y1, Y2, Y3, Y4 and Y5 in relation to Description of the compounds of the formula (I) according to the invention.

The O-benzyl-nitrosalicylic acid amides of the formula (V) are not yet known, as new products constitute an object of the present application.

The O-benzyl-nitrosalicylic acid amides of the formula (V) are obtained if they are reacted (process g) O-benzyl-nitrosalicylic acid derivatives of the formula (VI), wherein X7 means halogen, hydroxy or alkoxy, with an amine of the formula (VII), optionally in the presence of a diluent, if appropriate in the presence of a condensing agent and, if appropriate, in the presence of a Acid acceptor.

The O-benzyl-nitrosalicylic acid derivatives necessary as starting materials for carrying out process g) according to the invention are generally defined by the formula (VI). In this formula (VI), X7 means halogen, preferably chlorine; hydroxy or alkoxy, preferably methoxy or ethoxy.

The O-benzyl-nitrosalicylic acid derivatives of the formula (VI) are known and can be prepared according to known methods (see, for example, J. Am.

Chem. Soc. 1959, 5215-5217).

The amines of the formula (VII), which are additionally necessary as starting materials for carrying out process g) according to the invention, have been described above in relation to the description of process f) according to the invention.

The alkylation agents, which are also necessary as starting materials, for carrying out process a) according to the invention are generally defined by means of formula (III). In this formula (III), R 1 preferably has or especially that meaning which has already been indicated in a preferred manner or, more particularly, for R 1 in relation to the description of the compounds of the formula (I) according to the invention. X1 means halogen, alkoxy or alkylcarbonyloxy, preferably chloro, hydroxy, methoxy or ethoxy or acetoxy.

The acylating agents of the formula (III) are known reagents in organic chemistry.

The nitrosalicylic acid amides of the formula (IV), necessary as starting materials for the embodiment of process b) according to the invention, have already been described above in relation to the description of process d) according to the invention.

The O-benzyl-nitrosalicylic acid amides of the formula (V), which are necessary as starting materials for carrying out process c) according to the invention, have already been described above in relation to the description of process e).

Suitable diluents for carrying out processes a), f) and g) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, ethylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1/2-dimethoxyethane, 1,2-diethoxyethane or anisole; ketones, such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; 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 hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; sulfoxides, such as dimethylsulfoxide or sulfones, such as sulfolane.

Suitable diluents for carrying out processes d) and e) according to the invention are all inert organic solvents. These preferably include esters such as methyl acetate or ethyl acetate; alcohols, such as methanol, ethanol, n- or i-propanol, n- i-, sec- or tert-butanol, ethanediol, propane-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, water, saline solutions, such as for example ammonium chloride solution, acids, such as for example hydrochloric acid or acetic acid, as well as arbitrary mixtures of the indicated diluents.

Suitable diluents for carrying out processes h), i), j) and 1) according to the invention are all inert organic solvents. These preferably include ethers, such as 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-metipyrrolidone or hexamethylphosphorotriamide; sulfoxides, such as dimethylsulfoxide; or sulfones, such as sulfolane.

The diluents for carrying out process k) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, ethylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile.

The processes a), f), g) according to the invention are carried out, if appropriate, in the presence of a suitable acid-accepting agent. As such, all inorganic or organic bases are suitable. TO they preferably include hydroxides, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, bicarbonate of potassium or sodium bicarbonate as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The processes b), c), d) and e) according to the invention are carried out, if appropriate, in the presence of a catalyst. As such, all the catalysts which are usually used for hydrogenations are also suitable. Examples which may be mentioned are: Raney nickel, palladium or platinum, optionally on a support material, such as, for example, activated carbon.

The process c) according to the invention is also carried out in the presence of hydrogen or, where appropriate, in the presence of a non-noble metal. Examples of non-noble metals which may be mentioned are: zinc, tin, iron, aluminum or magnesium.

Other dehydrating agents, especially acetic anhydride, are suitable as other reaction aids for carrying out the processes a), b) and c) according to the invention.

The processes f) and g) according to the invention are carried out, if appropriate, in the presence of a condensation agent. These include acyl halide formers, such as, for example, phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiol, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ) or triphenylphosphine / tetrachloromethane.

The processes h), i), j) and 1) according to the invention are carried out, if appropriate, in the presence of a suitable acid-binding agent. As such, they enter consideration of all usual inorganic or organic bases. These preferably include hydrides, hydroxides, alcoholates, carbonates or bicarbonates of alkaline earth metals or alkali metals such as, for example, sodium hydride, sodium amide, potassium tert-butylate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate or baking soda.

All catalysts for the processes h), i), j) and 1) according to the invention are suitable all copper (I) salts, such as for example cuprous (I), cuprous (I) or cuprous iodide (I) ), or else fluorides, such as for example sodium, potassium or ammonium fluoride, as well as tertiary ammonium fluorides, such as tetrabutylammonium fluoride.

The process k) according to the invention is carried out, if appropriate, in the presence of a suitable catalyst. Suitable as such are all tertiary amines, such as, for example, trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU), as well as amides, such as dimethylformamide.

Suitable halogenating agents for carrying out process k) according to the invention are all reagents that can exchange hydroxyl groups, bonded on carbon, by chlorine. Examples which may be mentioned are: phosgene, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride and optionally also hydrogen chloride or chlorine.

The reaction temperatures in the carrying out of processes a), b), c), d), e), f) and g) can vary within wide limits. In general, temperatures are from 0 ° C to 180 ° C, preferably at temperatures from 0 ° C to 130 ° C.

The reaction temperatures may vary in carrying out processes h), i), j) and 1) within wide limits. In general, work is carried out at temperatures -20 ° C to 200 ° C, preferably at temperatures from -10 ° C to 150 ° C.

The reaction temperatures may vary in carrying out process k) according to the invention within wide limits. In general, the process is carried out at temperatures from 0 ° C to 250 ° C, preferably at temperatures from 0 ° C to 200 ° C.

To carry out the process a) according to the invention for the preparation of the compounds of the formula (I), generally 1 to 2,000 moles, preferably 1 to 2 moles, are used per mole of the aminosalicylic acid amide of the formula (II). 1 to 800 moles of acylating agent of the formula (III).

To carry out the processes b) and c) according to the invention for the preparation of the compounds of the formula (I), the molarity of the nitrosalicylic acid amide of the formula (IV) or of the acid amine is used per mole. O-benzyl-nitrosalicylic acid of the formula (V), in general from 100 to 2,000 moles, preferably from 200 to 1,000 moles of formic acid.

To carry out the process d) according to the invention for the preparation of the compounds of the formula (II), per mol of the nitrosalicylic acid amide of the formula (IV), in general from 1 to 100 mol, preferably from 2 to 20 moles of the agent of reduction.

To carry out the process e) according to the invention for the preparation of the compounds of the formula (11) / they are used, for the preparation of the compounds of the formula (II), they are used, per mole of the O-acid amide -benzylnitrosalicylic acid of the formula (V), in general, from 1 to 100 moles, preferably from 2 to 50 moles of hydrogen.

To carry out the process f) according to the invention for the preparation of the compounds of the formula (IV) are used, per mole of the amine of the formula (VII), in general from 0.5 to 10 moles, preferably from 0.8 to 5 moles of the 2-hydroxy-3-nitrobenzoic acid or of the 2-hydroxy-3-chloride -nitrobenzoyl.

For carrying out process g) according to the invention for the preparation of the compounds of the formula (V) are used, per mole of the amine of the formula (VII), in general from 0.5 to 10 moles, preferably from 0.8 to moles of the o-benzyl-nitrosalicylic acid derivative of the formula (VI).

For carrying out process h) according to the invention for the preparation of the compounds of the formula (VII-a) are used, per mole of the aminophenol of the formula (X), in general from 0.5 to 5 moles, preferably from 0.8 to 2 moles of halogenopyrimidine of the formula (IX), or of diazol of the formula ( VIII).

For carrying out the process i) according to the invention for the preparation of the compounds of the formula (VII-a) are used, per mole of the phenol of the formula (XII), in general from 0.5 mol to 5 mol, preferably from 0.8 to 2 mol of aminophenoxypyrimidine (XI).

For carrying out process j) according to the invention for the preparation of the compounds of the formula (IX-a) are used, per mole of the phenol of the formula (XII), in general from 0.5 to 5 moles, preferably from 0.8 to 2 moles of the 4,6-dichloro-5-fluoropyrimidine (XIII). P For carrying out the process k) according to the invention for the preparation of 4,6-dichloro-5-fluoropyrimidine (XIII), per mole of 5-fluoro-6-hydroxy-4 (1H) -pyrimidinone (XIV) are used ), in general from 0.05 to 20 moles, preferably from 0.1 to 10 moles of halogenating agent.

For carrying out the procedure 1) according to invention for the preparation of the compounds of the formula (XI) are, per mole of the amino acid of the formula (X), generally 0.5 to 5 moles, preferably 0.8 to 2 moles of trihalopyrimidine (XV).

The processes a) to 1) according to the invention are generally carried out under normal pressure. However, it is also possible to work under higher pressure or under reduced pressure, generally between 0.1 bar and 10 bar.

The products according to the invention have a powerful microbicidal effect and can be used in practice to combat undesired micro-organisms, such as fungi and bacteria, in the protection of plants and in the protection of materials.

Fungicidal agents are used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes.

Bactericidal agents are used to protect plants against pseudomonadaceae, rhizobiaceae, enterobacteriaceae, corynebacteriaceae and streptomycetes.

Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be mentioned by way of example, but without any limiting character: types of Xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia types, such as, for example, Erwinia amylovora; Pythium types, such as for example Pythium ultimun; types of Phytophthora, such as for example Phytophthora infestans; Pseudoperonospora types, such as for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara types, such as, for example, Plasmopara viticola; Bremia types, such as, for example, Bremia lactucae; Peronospora types, such as, for example, Peronospora pisi or P. brassicae; Erysiphe types, such as for example Erysiphe graminis; Sphaerotheca types, such as for example Sphaerotheca fuliginea; types of Podosphaera, such as for example Podosphaera lencotricha; Venturia types, such as, for example, Venturia inaequalis; types of Pyrenophora, such as, for example, Pyrenophora teres or P. graminea; (form of conidia, Drechslera, Syn: Helminthosporium); types of Cochliobolus, such as, for example, Cochliobolus sativus (conidia form, Drechslera, Syn: Henminthosporium); Uromyces types, such as, for example, Uromyces appendiculatus; Puccinia types, such as Puccinia recondita; Sclerotinia types, such as, for example, Sclerotinia sclerotiorum; types of Tilletia, such as for example Tilletia caries; types of Ustilago, such as for example Ustilago nuda or Ustilago avenae; Pellicularia types, such as, for example, Pellicularia sasakii; types of Pyricularia, such as, for example, Pyricularia oryzae; Fusarium types, such as for example Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of Leptosphaeria, such as for example Leptosphaeria nodorum; Cercospora types, such as, for example, Cercospora canescens; Alternate types, such as Alternarla brassicae; Pseudocercosporella types, such as, for example, Pseudocercosporella herpotrichoides.

The good compatibility with the plants and the active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil.

In this case, the active compounds according to the invention will be used with particularly good success in combating diseases in vine, fruit and vegetable plantations, such as, for example, against Venturia types and Phytophthora types. Grain diseases, such as, for example, Pseudocercosporella types or rice diseases, such as Pyricularia types, are also successfully controlled.

In addition, the active products according to the invention They are suitable to increase harvesting of crops. They also have minimal toxicity and have a good compatibility with plants.

The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as cold and hot fog ultra-low volume (ULV) formulations.

These formulations are prepared in known manner, for example by mixing the active compounds with extenders, that is, with liquid solvents, liquefied gases under pressure and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam generating means. When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol, or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as water; by liquefied gaseous excipients or excipients are meant those liquids which are gaseous at normal temperature and pressure, for example propellant gases for aerosols, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide; as solid excipients, the ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and the synthetic molten minerals, such as highly dispersed silicic acid, aluminum oxide and silicates; as solid excipients for granulates, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as sawdust, walnut shells, can be used of coconut ears corn and tobacco stalks; suitable emulsifiers and / or foamers are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated esters of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates as well as albumin hydrolysates; Suitable dispersants are sulfite lignin blends and methylcellulose.

Adhesives, such as carboxymethylcellulose and natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as phospholipids, such as cephalin and lecithin and synthetic phospholipids can be used in the formulations. Other additives can be mineral or vegetable oils.

Colorants, such as inorganic pigments, for example, iron oxide, Prussian blue titanium oxide and organic colorants, such as alizarin, azo and metal phthalocyanine dyes as well as trace nutrients, such as iron, manganese salts, boron, copper, cobalt, molybdenum and zinc.

The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product.

The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as cold and hot fog ultra-low volume (ULV) formulations.

The active compounds according to the invention can be used as such or in their formulations even in admixture with fungicides, bactericides, acaricides, nematicides or insecticides so as to extend the spectrum of activity or to overcome resistance developments. In many cases synergistic effects are obtained in this way, that is to say that the activity of the mixture is greater than the activities of the individual components.

The following compounds are suitable as mixing components: Fungicides: Aldimorph, Ampropylfos, Ampropylfos-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin, Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacrylisobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimat, Buthiobat, Calciumpolysulfid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinómethionat), Chlobenthiazon, Chlorfenazole, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozycalon, Cufraneb, Cymoxanil, Cyproconazole, Cyprodinil, Cyprofuram, Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran , Diethofencarb, Difenoconazole, Dimethirimol, Dimethomorph, Diniconazole, Diniconazole-M, Dinocap, Diphenylamin, Dipyrithione, Ditalimphos, Dithianon, Dodemorph, Dodine, Drazoxolon, Ediphenphos, Epoxiconazole, Etaconazole, Ethyrimol, Etriadiazole, Famoxadon, Fenapanil, Fenarimol, Fenbuconazole, Fenfuram , Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentihidroxyd, Ferbam , Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazole, Flurprimidol, Flusilazole, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fosetyl-sodium, Ftalid, Fuberidazole, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis, Fumercyclox, Guazatin, Hexachlorobenzol, Hexaconazol, Hymexazol, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilate, Iminoctadinetriacetate, Iodocarb, Ipconazole, Iprobenfos (PPI), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Kasugamycin, Kresoxim-methyl. Preparation of copper, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, copper oxide and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanypyrim, Mepromil, Metalaxyl, Metconazole , Methasulfocarb, Nethfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazole, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Natrium, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Pyroxyfur, Quinconazole, Quintozen ( PCNB), Sulfur and sulfur preparations, Tebuconazole, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Tthiophanatemethyl, Thiram, Thioxymid, Tolclofos-methyl, 5 Tolylfluanid, Triadimefon, Triadimenol, Triazbutyl, Triazoxid, Trichlamid, Tricyclazole, Tridemorph, Triflumizol, Triforin, Triticonazole, Uniconazole, Validamycin A, Vinclozolin, Viniconazole, -j_0 Zarilamide, Zineb, Ziram as well as Dagger G, OK-8705, OK-8801, a- (1,1-dimethylethyl) -β- (2- phenoxyethyl) -1 H-1,2,4-triazole-1-j-5 ethanol, - (2,4-dichlorophenyl) -β-fluoro-b-propyl-lH-1,2,4-triazole-1-ethanol, - (2,4-dichlorophenyl) -β-methoxy-a-methyl-lH-1,2,4-triazole-1-ethanol, OL- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) -phenyl] -methylene] -1H-1,2,4-triazole-1-ethanol, (5RS, 6RS) -6-hydroxy-2, 2,7,7-tetramethyl-5 - (1H-1, 2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide, carbamate of. { 2-methyl-l- [[1- (4-methylphenyl) -ethyl] -amino] - carbonyl] -propyl} -l-isopropyl, 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) -oxime, 1- (2-methyl- l-naphthalenyl) -lH-pyrrole-2, 5-dione, 1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1- [(diiodomethyl) -sulfonyl] -4-methyl-benzene, l- [[2- (2,4-dichlorophenyl) -1, 3-dioxolan-2-yl] -methyl] -1H-imidazole, 1- [[2- (4-chlorophenyl) -3-phenyloxyranyl] -methyl) -1 H-1,2,4-triazole, 1- [1- [2- [(2,4-dichlorophenyl) -methoxy] -phenyl] -etenyl] -1H-imidazole, l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4' -trifluoromethoxy-4'-trifluoromethyl- 1,3-thiazole-5-carboxanilide, 2,2-dichloro-N- (1- (4-chlorophenyl) -ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide, 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-triiodo-2-propenyl) -2H-tetrazole, 2- [(1-methylethyl) -sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole, 2- [[ 6-deoxy-4-0- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] -amino] -4-methoxy-lH-pyrrolo [2, 3-d] - pyrimidine-5-carbonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentandinitrile, 2-chloro-N- (2,3-dihydro-l, 1,3-trimethyl-lH-inden-4-yl) ) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide, 2-phenylphenol (OPP), 3,4-dichloro-l- [4- (difluoromethoxy) - phenyl] -lH-pyrrole-2, 5-dione, 3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3- (1,1-dimethylpropyl) ) -l-oxo-lH-inden-2-carbonitrile, 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine, 4-chloro-2-cyan-N, N-dimethyl- 5- (4-methylphenyl) -lH-imidazole-1-sulfonamide, 4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one, 8- (1,1-dimethylethyl) -N-ethyl -N-propyl-1,4-dioxaspiro- [4,5] decan-2-methanamine, 8-hydroxyquinolinesulfate, 9H-xanten-9-carboxylic-2- [(phenylamino) -carbonyl] -hydrazide, bis- (1 -methylethyl) -3-methyl-4- [(3-methylbenzoyl) -oxy] -2,5-thio-fendicarboxylate, cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazole) -l-il) - cycloheptanol, cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride, ethyl- [(4-chlorophenyl) -azo] -cyanoacetate , potassium bicarbonate, Methantethrathiol-Sodium salt, methyl-1- (2,3-dihydro-2, 2-dimethyl-lH-inden-1-yl) -1H-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) -1-methyl-cyclohexanecarboxamide, 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-l- [(chloroacetyl) -amino] -ethyl] -benzamide, N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N '-methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine, sodium salt 0, 0-diethyl- [ 2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1,2,3-benzothiadiazole-7-carbothioate, spiro [2H] -l-benzopyran-2, lr (3'H) -isobenzofuran] -3'-one.

Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, 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-chlorophenyl) -1- (ethoxy-methyl) -5- (trifluoromethyl) -lH- pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Brornophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N- [(6-chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanimidamide , Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Delta ethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos , Diclofhos, Dicrothos, Diethion, Diflubenzuron, Dimethoat, Dymethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad , Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinan, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH , Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, 'Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, Zetamethrin.

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

The active products can be used as such in the form of their formulations or of the forms of application prepared from the above, such as ready-to-use solutions, suspensions, injectable powders, pastes, soluble powders, dusts and granules. The use is carried out in the usual manner, for example by watering, spraying, sprinkling, spreading, dusting, foaming, brush application, etc. It is also possible to apply the active products also according to the ultra-low volume process or to inject the active product preparation or the active product itself into the soil. The seeds of the plants can also be treated.

When treating parts of plants the concentration of active product can vary in the forms of application within a wide range. When treating parts of the plants, the amounts of active compound used are generally between 1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the amounts used of active product are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0. 01 and 10 g per kilogram of seeds. When the soil is treated, the quantities used of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

Preparation examples: Example (1).

Procedure c). 1.67 g (3.02 mmol) of 2-benzyloxy-N- [4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl) -3-nitro-benzamide are stirred in 20 ml of formic acid with 0.4 nickel g Raney for 24 hours at 40 ° C. The mixture is poured into water and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated by evaporation under reduced pressure. The residue is chromatographed on silica gel with cyclohexane / ethyl acetate (1: 1). 0.4 g (35% theory) of N- [4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl] -3-formyl-amino-2-hydroxy-benzamide is obtained in the form of colorless oil. HPLC: logP = 3.31 Example 1) .

Procedure b). 0.5 g (1.08 mmol) of N- [4- (4-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl] -2-hydroxy-3-nitrobenzamide are stirred in 10 ml of formic acid with 0.5 g of Raney nickel for 24 hours at 40 ° C. The mixture is poured into water and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated by evaporation under reduced pressure. The residue is chromatographed on silica gel with cyclohexane / ethyl acetate (1: 1). 0.4 g (81% of theory) of N- [4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl] -3-formyl- is obtained. amino-2-hydroxy-benzamide as a colorless oil. HPLC: logP = 3.31.

Obtaining the compounds of the formula (IV) Example (IV-1): Procedure f) A mixture consisting of 1.7 g (9 mmol) of 3-nitrosalicylic acid and 2.7 g (9 mmol) of 4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenylamine in 20 ml is heated. of toluene, under stirring, at 50 ° C. Then add 0.5 g of phosphorus trichloride and heat for another 4 hours at reflux to boiling. After cooling, the mixture is concentrated by evaporation and the residue is extracted with dichloromethane. The organic phase is washed several times with water and dried over sodium sulfate. Behind the Removal by distillation of the solvent gives 1.7 g (41% of theory) of N- [4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl] -2-hydroxy-3-nitrobenzamide. Mass spectrum: m / e = 462 (M +).

Obtaining the compounds of the formula (V). Example (V-l).

Procedure g). A solution of 4.3 g (18 mmol) of 2-benzyloxy-3-nitro-benzoyl chloride in 20 ml of dichloromethane is added dropwise at 0 ° C to a solution of 2.4 g (0.011 mol) of triethylamine and 5.3 g (18 mmol) of 4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenylamine in 30 ml of dichloromethane and stir for another 2 hours without additional cooling. The mixture is filtered, the filtrate it is washed with water, dried over sodium sulphate and concentrated by evaporation under reduced pressure. The residue is chromatographed on silica gel with cyclohexane / ethyl acetate (2: 1). 2.8 g (30% of theory) of 2-benzyloxy-N- [4- (5-fluoro-6-phenoxy-pyrimidin-4-yloxy) -phenyl] -3-nitro-benzamide are obtained as an oil. HPLC: logP = 4.56.

Obtaining the compounds of the formula (IX-a) Example (IX-a-1): Procedure j). A mixture of 5 g (0.0295 mol) of 4,6-dichloro-5-fluoropyrimidine and 5 g (0.036 mol) of potassium carbonate in 25 ml of acetonitrile is heated at 50 ° C. At this temperature, a solution of 3.8 g (0.03 mol) of 2-chlorophenol is added dropwise over the course of 6 hours. in 25 ml of acetonitrile and stirred for another 6 hours at this temperature. After cooling, the solvent is distilled off under reduced pressure and the residue is taken up with water and extracted several times with 40 ml of dichloromethane each time. The organic phase is washed with 10% sodium hydroxide solution, dried over sodium sulfate and concentrated again by evaporation under reduced pressure. 6.9 g (86.7% of theory) of 4-chloro-6- (2-chlorophenoxy) -5-fluoropyrimidine are obtained. ^ - MR: d = 7.24-7.53 (m, 4H); 8.29 (s, 1H) ppm.

Example (IX-a-2) Procedure j). A mixture of 3 g (0.01%) is heated to 70 ° C. moles) of 4,6-dichloro-4-fluoropyrimidine and 2.8 g (0.018 moles) of potassium carbonate in 30 ml of acetonitrile. At this temperature, a solution of 3.8 g (0.03 mol) of (5,6-dihydro- [1,4,2] dioxazin-3-yl) - (2-) is added dropwise over the course of 2 hours. hydroxy-phenyl) -methanone-O-methyl oxime in 20 ml of acetonitrile and heating at reflux for a further 16 hours. After cooling, the solvent is distilled off under reduced pressure and the residue is taken up with water and extracted several times with 40 ml of dichloromethane each time. The organic phase is washed with 10% sodium hydroxide solution, dried over sodium sulfate and concentrated again by evaporation under reduced pressure. 7 g (86.7% of theory) of [2- (6-chloro-5-fluoropyrimidin-4-yloxy) -phenyl] - (5,6-dihydro- [1,4,2] -dioxazin-3 are obtained. -yl) -methanon-O-methyloxime. ^ -NMR: d = 3.83 (s, 3H) -; 4.14 (m, 2H); 4.45 (m, 2H); 7.39-7.54 (m, 4H); 8.32 (s, 1H) ppm.

Obtaining 4,6-dichloro-5-fluoropyrimidine. Example (XIII): Procedure k). 30 ml of phosphorus oxychloride are added dropwise in the course of 30 minutes 7.8 g (0.064 mole) of N, N-dimethylaniline and stirred for 10 minutes at 25 ° C. Then add 8.3 g of 5-fluoropyrimidin-4,6-diol and heat for reflux for 15 hours. After cooling, the excess phosphorus oxychloride is removed by distillation under vacuum from the water pump and the residue is subjected to a vacuum distillation. 11.2 g (100% of the theory) of 4,6-dichloro-5-fluoropyrimidine are obtained with a boiling point of 58-60 ° C at 14 nabares.

Obtaining the compounds of the formula (VII-a] Example (VII-a-1); Procedure i] A mixture consisting of 2 g (9 mmol) of 4- (4-aminophenoxy) -6-chloro-pyrimidine, 1.1 g (9 mmol) of 3-chlorophenol and 2 g is refluxed for 4 hours. (18 mmoles) of anhydrous potassium carbonate in 20 ml of acetonitrile. The mixture is then filtered and the filtrate is concentrated by evaporation under reduced pressure.

The residue is taken up in dichloromethane, washed with water, the organic phase is dried over sodium sulphate and concentrated again by evaporation under reduced pressure. 1.3 g (46% of theory) of 4- (4-aminophenoxy) -6- (2-chlorophenoxy) -pyrimidine are obtained. HPLC: logP = 1.96.

Obtaining the compounds of the formula (XI) Example (XI-1): Procedure 1). Heat at reflux for 4 hours, a mixture consisting of 50 g (0.3 mol) of 4,6-dichloropyrimidine, 37 g (0.3 mol) of 4-aminophenol, 80 g (0.6 mol) of anhydrous potassium carbonate and 50 mg of cupric bromide-II in 600 ml of acetonitrile. The mixture is then filtered and the filtrate is concentrated by evaporation under reduced pressure. The residue is taken up in dichloromethane, washed with water, the organic phase is dried over sodium sulphate and again concentrated by evaporation under reduced pressure. 60 g (58% of theory) of 4- (4-aminophenoxy) -6-chloro-pyrimidine are obtained. HPLC: logP = 0.65.

Example (VII-a-2): Procedure h). 2.7 g of 6-chloro-5-fluoro-4- (2-chlorophenyloxy) pyrimidine and 1.5 g of potassium carbonate in 20 ml of acetonitrile are added and combined, under reflux, in the 1.5 hours, with 1.8 g of 2,3-dichloro-4-aminophenol. The mixture is heated at reflux for a further 12 hours, cooled, the solvent is removed in vacuo and the residue is taken up in 45 ml of dichloromethane. After washing with 0.25 N aqueous sodium hydroxide solution, the solution is combined with 5 g of activated carbon, filtered and the solvent is distilled off. The residue is chromatographed on silica gel with petroleum ether / ethyl acetate (2: 1). 2.7 g (64.3%) of 2,3-dichloro-4- [6- (2-chlorophenoxy) -5-fluoropyrimidin-4-yloxy] -phenylamine are obtained with a melting point of 162-163 ° C.

In a manner analogous to that of Example 1, as well as according to the general description of processes b) and c) according to the invention, the compounds of the formula (I-f) indicated in the following table 5 are obtained: (I-f) Table 5 Example? 2 Y3 logP Example Y2 Y3 logP Example Y2 Y3 logP twenty - . 20 -H 3.27 ^ Example? 2 Y3 logP 29 -. 29 -H 4 0 Cl 30 -H 3.88 In a manner analogous to that of example (IV-1), and in accordance with the general description of process f) according to the invention, the compounds of formula (IV-a) indicated in the following table 6 were obtained: Table 6 Example Physical data Mass spectrum.

Analogously to the example (V-1), and according to the general description of process g) according to the invention, the compounds of the formula (VII-a) indicated in the following table 7 were obtained: Table 7. Example? 2 Y3 logP Example? 2 Y3 logP (V-ll) -H VYVY to 4.73 (V-12) -H VYV 4.35 -H 2 (V-15) -H or 4.4 Y? ? Br Example Y2 Y3 logP Example Y2 Y3 logP (V-34) -H xr n Vo "?? 5.12 In a manner analogous to that of the examples (VII-a-1) and (VII-a-2), as well as according to the general description of the processes h) and i) according to the invention, the compounds of the formula ( Vll-b) indicated in the following table: (Vp-b) TABLE 8 Ei. ns Y10 Y9 A? Z3 P.f: oqP 1 Phenyl 130 1.53 0 Phenyl 2,57 VII-a-5 -H -H 1 Phenyl 1,88 l Phenyl 2,32 VII-a-7 -H -H 1 4-Chloro-phenyl 2.12 VII-a-8 -H -H 1 3, 4-difluorophenyl 4,55 VII-a-9 -H -H j | I 1 4-bromophenyl 2,02 VII-a-10 -H -H 2, 4-dichlorophenyl 2,33 VII-a-11 -H -H x 3, -dichlorophenyl 2,48 VII-a-12 -H -H 1 3-methoxyphenyl 1.61 E-i. ng Y10 Y9 Ar £ m Z3 P. f; LosP VII-a-13 -H-4-trifluoromethyl-2, 21 phenyl VII-a-14 -H -H | l J 1 3-trifluoromethyl-2,18 phenyl VII-a-15 -H -H x 2-fluorphenyl 1.61 VII-a-16 -H -H 3-Fluorophenyl 1,46 VII-a-17 -H -H II .JL 1 3-tolyl 2.12 VII-a-18 -H -H 1 2,5-dxchlorophenyl 2,26 VII-a-19 -H -H 1 2, 3-dimethylphenyl 1.98 VII-a-20 -H -H || I 1 3,5-dimethylphenyl 2.12 VII-a-21 -H -H i 2, -difluorophenyl 1.76 VII-a-22 -H -H 1 3, 5-dichlorophenyl 2,6 VII-a-23 -H -H- ^ 1 4-methoxyphenyl 1.52 N ^ N E-i. nfi Y10 Y9 Ar Z3 P.f i LoqP VII-a-24 -H -H p i 4-f lúorfil 1,59 Vll-a-25 -H -H 1 3-bromofenyl 2.05 VII-a-26 -H -H p 1 2, 3-dlclorofen? Lo 2,26 VII-a-27 -H -H 1 2, 5-dimethylphenyl 2.02 viI-a-28 -H -H! | | 1 4-phenoxyphenyl 2,55 VII-a-29 -H -H 1 2-me'to? Ifenil0 lf 6 VII-a-30 -H -H 2-tolyl 1.71 VII-a-31 -H -H N N x 3-phenoxyphenyl 2,54 VII-a-32 -H-H-2-chlorophenyl 3,61 VII-a-33 -H -H N - ^^ N 1 2, 6-dimethylphenyl VII-a-34 -H -H .1 2,6-dichlorophenyl Application examples: Example A Phytophthora (tomato) / protectant assay. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether.

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

To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After the spray applied coating is dried, the plants are inoculated with an aqueous suspension of Phytophthora infestans. The plants are then placed in an inoculation cabinet at approximately 20 ° C and with a relative humidity of 100%.

The evaluation is carried out 3 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of untreated controls, while an activity level of 100% means that no attack is observed.

In this test, for example, the following compounds of Preparation Examples 1, 2 and 4 show, with an application amount of 100 g / ha, an activity level of 80% compared to untreated controls.

EXAMPLE B Assay with Venturia (apple tree) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether.

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

To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying of the spray applied coating plants are inoculated with an aqueous suspension of conidia of the pathogen of anthracnose of the apple tree Venturia inaequalis and then remain 1 day at 20 ° C approximately and 100% relative humidity of the air in an incubation cabin.

The plants are then placed in the greenhouse at approximately 21 ° C and with a relative humidity of approximately 90%.

The evaluation is carried out 12 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed.

In this test, for example, the following compounds of Preparation Examples 1 and 2 show, with an exemplary active product application amount of 100 g / ha, an activity level of 80% compared to untreated controls.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Having described the invention as above, the content of the following is claimed as property:

Claims (27)

1. Compounds of the general formula (i; characterized in that R1 signifies hydrogen, alkyl or alkoxy, Y "/ Y2, Y3 / Y4 and Y5 are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy and either Y ~ or Y3 mean -GZ, where G means one of the following groupings -Q-CQ-, -CQ-Q-, -CQ-Q-CH; -, -CH: -Q-CQ-, -Q-CQ-CH: -, -Q-CQ -Q-CH: -, -N = N-. -S'0) n, -CH-S (0) r-, -CQ-, -S (0) r-CH: -, -C (R3) = N-0-, -C (R3) = N-0-CH: -, -N (R4 -) -, -CQ-N (R4) -, -N (R4) -CQ-, -Q-CQ -N (R4) -, -N = C (R3) -Q-CH; -, -CH; -0-N = C (R3) -, -C (CH3) -0-N = C (R3) - , -N (R) -CQ-Q-, -CQ-N (R) -CQ-Q-, -N (R4) -CQ-Q-CH-, -QC (R3) = N-0-CH2-, -N (R4) -C (R3) = N-0-CH2-, -O-CH-C (R3) = N-0-CH _--, -N = N-C (R3) = N-0-CH2-, -C (= N-0-R5) -C (R5) = N-0-CH: -, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T -Ar1- or -T-Ar1-Q-, where Ar 1 signifies substituted arylene, heteroarylene, cycloalkylene or heterocycle alkylene (ie a double-linked aliphatic ring, in which one or more carbon atoms are replaced by heteroatoms, ie by atoms other than carbon), n means numbers 0, 1 or 2, Q means oxygen or sulfur, R3 means hydrogen, cyano, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively substituted, and R4 means hydrogen, hydroxy, cyano or means alkyl, alkoxy or cycloalkyl substituted respectively where appropriate, R5 means hydrogen or alkyl and T means a single bond, means oxygen, sulfur -CJ ^ -O-, -CH2-S- or means alkanediyl, if appropriate substituted, Z means alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl substituted respectively, if appropriate.

2. Compounds of the formula (I) according to claim 1, characterized in that R 1 preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; Y1, Y2, Y3, Y4 and Y5 are the same or different and denote hydrogen, halogen, cyano, alkyl or alkoxy with 1 to 4 carbon atoms, haloalkyl or haloalkoxy with 1 to 4 carbon atoms and 1 to 5 carbon atoms, respectively halogen the same or different, and either Y2 or Y3 mean -GZ, where G means one of the following groupings -Q-CQ-, -CQ-Q-, -CQ-Q-CHc- / -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N = N-, -S (0) n-, -CH2-S (0) n-, -CQ- -S (0) n-CH2-, -C (R3) = N-0-, -C (R3) = N-0-CH2-, -N (R4) -CQ-N (R4) -, -N (R4) - CQ-, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH2- -CH2-0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R4) -CQ-Q- -CQ-N (R4) -CQ-Q-, -N (R4) -CQ-Q-CH-, -QC (R3) = N-0 -CH2- -N (R4) -C (R3) = N-0-CH; -, -0-CH-C (R-) = N-0-CH: -, -N = N-C (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH_-, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -CN = C (CHJ - -T-Ar1- or -T-Ar: -Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R means hydrogen, cyano, means alkyl, alkoxy, alkylthio alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, respectively substituted in each case by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or by cycloalkyl with 3 to 6 carbon atoms substituted, where appropriate, by halogen, cyano, carboxy, alkyl with 1 to 4 carbon atoms or alkoxycarbonyl having 1 to 4 carbon atoms and R "means hydrogen, hydroxy, cyano or means alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms or cycloalkyl with 3 to 6 carbon atoms optionally substituted by halogen, by cyano by carboxy, by alkyl with 1 to 4 carbon atoms carbon or by alkoxycarbonyl with 1 to 4 carbon atoms, R5 means hydrogen or alkyl with 1 to 4 carbon atoms, Ar1 means phenylene, naphthylene, cycloalkylene, respectively substituted one or more times, in the same or different forms or means heteroarylene or heterocycloalkylene with 3 to 7 members in the ring, one of which means oxygen, sulfur or nitrogen and optionally one or two more mean nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano , amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl respectively straight chain or chain branched with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; respectively straight-chain or branched chain alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl with respectively 1 to 6 carbon atoms in the individual alkyl portions, as well as cycloalkyl with 3 to 6 carbon atoms and T means a simple bond, means oxygen, sulfur, -CH2-0-, -CH2-S- or means alkanediyl with 1 to 3 carbon atoms, Z means alkyl with 1 to 8 carbon atoms, optionally substituted one or several times, in the same or different ways by halogen, by cyano, by hydroxy, p amino, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl having 1 to 4 carbon atoms (which may be substituted, if appropriate, by halogen, respectively); means alkenyl or alkynyl with respectively up Eight carbon atoms, each substituted, if appropriate, by halogen, means cycloalkyl having 3 to 6 carbon atoms, each optionally substituted one or more times, in the same or different ways by halogen, cyano, carboxy, phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by haloalkoxy with 1 to 4 atoms carbon), by 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms; means phenyl, naphthyl respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, at least one of which means oxygen, sulfur or nitrogen and, if appropriate, one or two more mean nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or straight-chain or branched-chain alkylsulfonyl, respectively having 1 to 6 carbon atoms; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxy-alkylene with respectively 1 to 6 carbon atoms, respectively double-bonded, each optionally substituted one or more times, in the same or in different ways by halogen and / or by straight-chain or chain alkyl branched with 1 to 4 carbon atoms and / or straight chain or branched chain halogen with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; phenyl or phenoxy substituted, if appropriate one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl having 1 to 4 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, between which respectively 1 to 3 are the same or different heteroatoms, especially nitrogen, oxygen and / or sulfur, or a group wherein A1 means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, respectively, optionally substituted by cyano, for alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl or a group where A3 means alkyl having 1 to 4 carbon atoms and A4, A5, A6 and A7 are the same or different and independently of one another are hydrogen, alkyl or hydroxyalkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 4 atoms of carbon and 1 to 5 identical or different halogen atoms, A4 and A5 or A4 and A6 or A6 and A7 together with the respective carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms. carbon

3. Compounds of the formula (I), according to claim 1, characterized in that R 1 signifies hydrogen, methyl, ethyl, n- or i-propyl, methoxy or ethoxy, Y 1, Y 2, Y 3, Y 4 and Y 5 are the same or different and they mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy and either Y2 or Y3 mean -GZ-, where G means one of the following groups -Q-CQ-, -CQ-Q-, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2- -Q-CQ-Q-CH2-, -N = N-, -S (0) n-, -CH2- S (0) n-, -CQ-, -S (0) n-CH2-, -C (R3) = N-0-, -C (R3) = N-0-CH2-, -N (R4) -, -CQ-N (R4) -, -N (R4) -CQ-, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH2-, -CH2-0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R4) -CQ-Q-, • -CQ-N (R) -CQ-Q-, -N (R4) -CQ-Q-CH-, -Q-C (R3) = N-0-CH2-, -N (R4) -C (R3) = N-0-CH2-, -0-CHz-C (R3) = N-0-CH2-, -N = NC (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) = N-0-CH2-, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T-Ar1- or -TA ^ -Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R3 signifies hydrogen, cyano, methyl, ethyl or cyclopropylous and R4 signifies hydrogen, methyl, ethyl, or cyclopropyl, R5 means hydrogen or methyl, Ar1 means phenyl or pyridinediyl substituted, if appropriate, one to three times, in the same or different ways, meaning pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,2,3-triazindiyl, 1, 2, 4 -triazindiyl 1, 3, 5-triazindiilo respectively monosubstituido or means 1, 2, 4-thiadiazoldiilo, 1, 3, 4-thiadiazoldiilo, 1, 2, 4-oxadiazoldiilo, 1, 3, 4-oxadiazoldiilo, being chosen the possible substituents preferably from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , methylsulphinyl, ethylsulfinyl, methylsulfonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylstulphosate or trifluoromethylsulphonyl and T means a single bond, means oxy geno, sulfur, _CJJ2-0-, -CH2-S-, methylene, ethylene d propylene, Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted one to three times, in the same or in different ways by fluorine, by chlorine, by cyano or by methoxy; means vinyl, allyl or propargyl substi tudes respectively, where appropriate, by fluorine or chlorine; means cyclopropyl cyclobutyl, cyclopentyl or cyclohexyl each respectively substituted one to three times, in the same or different ways by fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; or Z means phenyl, 1,2,4-thiadiazoyl, 1,3-thiadia-olyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1, 2, 3. -triazinyl, 1,2,4-triazinyl or 1, 3, 5-triazinyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine , bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio , methylsulphinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively doubly linked, each optionally substituted one to four times, in the same or in different ways by fluorine, by chlorine, by methyl , by trifluoromethyl or by ethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or a grouping wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- o. t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2- methyl- prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a grouping wherein A3 means methyl or ethyl and A4, A5, A6 and A7 are the same or different and mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or A4 and A5 or A4 and A6 or A6 and A7, together with the corresponding carbon atoms, with which they are bound, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

4. Compounds of the formula (I), according to claim 1, characterized in that R 1 signifies hydrogen, methyl or methoxy, Y 1, Y 2, Y 3, Y 4 and Y 5 are the same or different and mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either Y2 or Y3 mean -GZ, where G means -C (R3) = N-0-CH2-, where R3 signifies methyl or cyclopropyl and Z means phenyl, pyridyl or substituted pyrimidyl respectively, optionally from one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl n-, i -, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or 1-propylthio, methylsulfinyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difl úlorchloromethylthio, trifluoromethyl-sulphonyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl, ethoxyiminoethyl, methylenedioxy or ethylenedioxy respectively doubly linked, each optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or by ethyl, as well as phenyl and phenoxy.

5. Compounds of the formula (I), according to claim 1, characterized in that R 1 is hydrogen, methyl or methoxy. Y1, Y2, Y3, Y4 and Y5 are the same or different and mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either Y2 or Y3 mean -GZ, where G means -T- Ar1- or -T-Ar1-0-, where Ar1 means 1, 2,4-thiadiazolidiyl, 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridinediyl, pyrimidindiyl or 1, 3, 5-triazindiyl respectively substituted one or two times, in the same or different ways by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, by methoxy, by methylthio, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, T means a single bond, means oxygen , sulfur, -CH2-0-, -CH2-S-, methylene, ethylene or propylene. Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted one to three times, in the same or in different ways, by fluorine, by chlorine, by cyano or methoxy; means vinyl, allyl or propargyl respectively substituted, if appropriate, by fluorine or chlorine; means cyclopropyl, cyclopentyl or cyclohexyl respectively substituted one to three times, in the same or different ways by fluorine, chlorine, cyano, methoxy, phenyl, methyl or ethyl; or Z means phenyl, pyridyl, pyrimidyl, thienyl, each optionally substituted one to three times, in the same or in different ways, with the possible substituents being chosen, preferably from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, diflúorclarometiltio, trifluoromethylsulphinyl or trifluoro ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively double-bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy or a grouping wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-propyl-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a grouping wherein A3 means methyl or ethyl and A4, A5, A6 and A7 are the same or different and independently of one another are hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl, or trifluoroethyl, or A4 and A5 or A4 and A6 or A6 and A7 together with the corresponding carbon atoms, with which they are linked, form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

6. Compounds of the formula (IV) characterized in that Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above.

7. Pesticidal agents, characterized in that they have a content in at least one compound of the formula (I) and / or the formula (IV) according to claims 1 to 6.

8. Process for combating pests, characterized in that compounds of the formula (I) and / or the formula (IV) according to claims 1 to 6 are allowed to act on the pests and / or on their environment.

9. Process for obtaining the compounds of formula (I), wherein R "signifies hydrogen, alkyl or alkoxy, Y :, Y2, Y", Y4 and Y5 are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl , alkoxy or haloalkoxy and well Y "or Y ~ signify -GZ, where G means one of the following groupings -Q-CQ-,, -CQ-Q-, -CQ-Q-CH; -, -CH-Q- CQ-, -Q-CQ-CH; -, -Q-CQ-Q-CH; -, -NsN-, S (0 ^ -, -CH-S (0) r-, -CQ-, -S ( 0.-CH_-, -C (R3) = N-0-, -C (R3) = N-0-CH: -, -N (R4 -) -, -CQ-N (R ") -, -N (R4) -CQ -, -Q-CQ-N (R4) -, -N = C (R3) -Q-CH: -, -CH: -0-N = C (R3) -, -C (CH3) -0-N = C (R3) -, -N (R4) -CQ-Q-, -CQ-N (R4) -CQ-Q-, -N (R4) -CQ-Q-CH; -, -QC (R3) = N-0-CH; -, -N (R4) -C (R3) ) -NO-CH-, -O-CH-C (R3) = N-0-CH-, -N = N-C (R3) = N-0-CH_-, -C (= N-0-R5) -C (R3) = N-0-CH: -, -C (= N-0-R5) -C (R3) -0-N = CH-, -C (= N-0-R5) -C (R3) -0-N = C (CH3) - -T -Ar1- or -T-Ar: -Q-, where Ar 'means arylene, if any, substituted, heteroarylene, cycloalkylene or heterocycle alkylene (ie a double-bonded aliphatic ring, in which one or more carbon atoms are replaced by heteroatoms, ie by atoms other than carbon), n means 0, 1 or 2, Q means oxygen or sulfur, R3 means hydrogen, cyano, or means substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively if appropriate, and R4 signifies hydrogen, hydroxy, cyano or means alkyl, alkoxy or cycloalkyl substituted respectively where appropriate, R5 signifies hydrogen or alkyl and T signifies a single bond, means oxygen, sulfur -CH2-0-, -CH2- S- or means substituted alkanediyl, Z means alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl substituted respectively where appropriate, characterized in that a) Aminosalicylic acid amides of the general formula (II) are reacted, wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with acylating agents of the general formula (III) OR R x (HI) wherein R1 has the meaning indicated above and X1 means halogen, hydroxy, alkoxy or alkylcarbonyloxy, if appropriate in the presence of a diluent, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of another auxiliary agent of the reaction, or b) nitrosalicylic acid amides of the general formula (IV) are reacted (IV) wherein Y1, Y2, Y3, Y4 and Y5 have the meanings given above, with formic acid, if appropriate in the presence of a catalyst and, if appropriate, in the presence of another reaction auxiliary agent, or c) O-benzyl-nitrosalicylic acid amides of the general formula (V) are reacted, wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with formic acid, if appropriate in the presence of hydrogen or a non-noble metal, optionally in the presence of a catalyst and, if appropriate, in the presence of another agent auxiliary to the reaction.

10. Process for obtaining the compounds of formula (IV), as defined in claim 6, characterized in that 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-chloride are reacted (process c) nitrobenzoyl with an amine of the formula (VII), wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, optionally in the presence of a diluent, if appropriate, in the presence of a condensing agent, and, if appropriate, in the presence of an acceptor of acid.

11. Use of the compounds of the formula (I) and / or of the formula (IV) and the agents according to claims 1 to 7 to combat pests.

12. Process for obtaining pesticidal agents, characterized in that compounds of the formula (I) and / or the formula (IV) according to claims 1 to 7 are mixed with extenders and / or with surfactants.

13. Compounds of the formula (II) characterized in that Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, in claim 1.

14. Process for obtaining the compounds of the formula (II) as defined in claim 13, characterized in that (process d) are reacted amines of the nitrosalicylic acid of the general formula (IV), wherein Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, with a reducing agent, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst, or (process e) they react acid amides O-benzyl-nitrosalicylic acid of the general formula (V), wherein Y1, R2, A3, 4 and Y5 have the meanings indicated above, with hydrogen, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst.

15. Compounds of the formula characterized because Y6, Y7, Y8, Y9 and Y10 are the same or different and mean hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy and, Y7 or Y8 mean a grouping Ar2 ^ where m means 0 or 1, Ar 2 means 1,2,4-oxadiazol-3,5-diyl, 1,2,4-thiadiazol-3,5-diyl or means pyrimidin-4,6-diyl substituted, if appropriate, in the position 5 by halogen and Z3 signifies aryl, if any, substituted.

16. Compounds of the formula (Vil-a), according to claim 15, characterized in that Y6, Y7, Y8, Y9 and Y10 are the same or different and mean hydrogen, halogen, cyano, alkyl or alkoxy with respectively 1 to 4 carbon atoms. carbon, haloalkyl, or haloalkoxy with respectively 1 to 4 carbon atoms or 1 to 5 same or different halogen atoms, and either Y7 or Y8 mean a grouping ? x £ where m means 0 or 1, Ar2 means 1,2,4-oxadiazol-3, 5-diyl, 1, 2,4-thiadiazole-3, 5-diyl, or means pyrimidin-4,6-diyl optionally substituted in the 5-position by fluorine or chlorine and Z3 means phenyl or naphthyl respectively substituted one or more times, in the same or in different ways the possible substituents being preferably chosen from the following enumeration: halogen, cyano, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, with respectively 1 to 6 carbon atoms, respectively straight chain or branched chain; alkenyl or alkenyloxy with respectively 2 to 6 carbon atoms, respectively straight-chain or branched chain; haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulphonyl having 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, respectively straight chain or branched chain; haloalkenyl or haloalkenyloxy with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, respectively straight-chain or branched chain; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy, respectively straight-chain or branched chain, each having 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene, with respectively 1 to 6 carbon atoms, respectively double-bonded, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 6 carbon atoms; to 4 carbon atoms and / or straight-chain or branched-chain halo-haloalkyl with 1 to 4 carbon atoms and 1 to 9 halogen atoms same or different; cycloalkyl with 3 to 6 carbon atoms; phenyl or phenoxy substituted, if appropriate one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl having 1 to 4 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, among which, respectively 1 to 3 are the same or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, or a group N where A8 means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A9 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano, by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl, or by a group wherein A10 means alkyl with 1 to 4 carbon atoms and A11, A12, A13 and A14 are the same or different and independently of each other, hydrogen, alkyl or hydroxyalkyl with 1 to 4 carbon atoms or halogen alkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or A11 and A12 or A11 and A13 or A13 and A14 together with the corresponding carbon atoms, with which they are bonded, form an aliphatic ring with 5, 6 or 7 carbon atoms.

17. Compounds of the formula (VII-a), according to claim 15, characterized in that Y6, Y7, Y8, Y9 and Y10 are the same or different and mean hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, trifluoromethyl or difluoromethoxy, and either Y7 or Y8 mean a group where m means 0 or 1, Ar2 means 1,2,4-oxadiazol-3,5-diyl, 1,2,4-thiadiazol-3,5-diyl or means pyrimidin-4,6- The diyl optionally substituted in the 5-position by fluorine or chlorine and Z3 means phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine , bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio , methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methylenedioxy, ethylenedioxy, respectively doubly linked, substituted or optionally from one to four times, same or differently by fluorine, chlorine, methyl, trifluoromethyl or ethyl, phenyl, 4-chlorophenyl, 4-methylphenyl, phenoxy, 4-chlorophenoxy, 4-methylphenoxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or grouping Aa I O where A8 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl, A9 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en- 3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthio ethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl, or a group wherein A10 means methyl or ethyl and A11 and A12 or A11 and A13 or A13 and A14 are the same or different and mean, independently of each other, hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or A11 and A12 or A11 and A13 or A13 and A14 together with the corresponding carbon atoms, with which they are bound, they form a cycloaliphatic ring with 5, 6 or 7 carbon atoms.

18. Process for obtaining the compounds of formula (Vil-a) as defined in claim 15, characterized in that diazoles of the general formula (VIII) or halogeno-pyrimidine of the general formula (IX) are reacted, (HIV) (IX) where m means 0 or 1, X 2 means hydrogen, fluorine or chlorine, X 3 means chlorine or fluorine, X 4 means methylsulfonyl, chlorine or bromine and Q means oxygen or sulfur, and Z 3 has the meaning indicated above, with an aminophenol of the formula, wherein Y11, Y12, Y13, Y14 and Y15 are the same or different and denote hydrogen, halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy, and either Y12 or Y13 means amino, if appropriate in the presence of a diluent, in given case in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst, (process i) aminophenoxypyrimidine of the general formula (XI) are reacted, wherein X2, Y11, Y12, Y13, Y14 and Y15 have the meanings given above and X5 means chloro or fluoro, with a phenol of the general formula (XII), Z3-OH (???; wherein Z3 has the meaning indicated above, if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst.

19. Compounds of the formula (IX-a) characterized in that Z3 has the meanings given above in claims 15 to 17, the compound being excluded methyl 2- [(6-chloro-5-fluoro-4-pyrimidinyl) -oxy] -a- (methoxymethylene) -benzoate.

20. Process for obtaining the compounds of the formula (IX-a) as defined in claim 19, characterized in that (process j) phenols of the general formula (XII) are reacted, Z3-OH (XII) wherein Z3 has the meaning indicated above, with 4,6-dichloro-5-fluoropyrimidine (XIII), if appropriate in the presence of a diluent, optionally in the presence of an acid-binding agent and, if appropriate, in the presence of a catalyst.

21. 4, 6-dichloro-5-fluoropyrimidine of the formula (XIII),

22. Procedure for obtaining 4,6-dichloro-5-fluorpirimidine, characterized in that (method k) the 5-fluoro-6-hydroxy-4 (1H) -pyrimidinone (XIV) is reacted with a chlorinating agent, if appropriate in the presence of a diluent and, if appropriate, in the presence of a catalyst .

23. Compounds of the formula (XI) characterized in that X \ Y11, Y, Y, Y14 and Y1S have the meanings indicated in claim l

24. Process for obtaining the compounds of the formula (XI) as defined in claim 23, characterized in that (process 1) trihalogenopyrimidines of the formula (XV) are reacted (XV) wherein X2 and X5 have the meanings indicated above and X6 means fluorine or chlorine, with an aminophenol of the formula (X), optionally in the presence of a diluent, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a catalyst.

25. Compounds of the formula (V), characterized in that Y1, Y2, Y3, Y4 and Y5 have the meanings indicated above, in claim 1.

26. Process for obtaining the compounds of the formula (V), as defined in claim 25, characterized in that (process g) O-benzyl-nitrosalicylic acid derivatives of the formula (VI) are reacted, characterized in that X7 means halogen, hydroxy or alkoxy, with an amine of the formula (VII), optionally in the presence of a diluent, if appropriate, in the presence of a condensing agent and, if appropriate, in the presence of an acceptor of acid.

27. Use of the compounds of formula (VI), (IV), (VII-a), (IX-a), (XI), and (XIII) as intermediates.