Substituted pyrimidines, process for their preparation, and their use as pesticides and fungicides
First Claim
1. A compound of the formula I ##STR271## in which R1 is hydrogen, halogen, (C1 -C4)-alkyl or (C3 -C6)-cycloalkyl,R2 is hydrogen, (C1 -C4)-alkyl, halogen, (C1 -C4)-haloalkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkyl, (C1 -C4)-alkylthio, (C1 -C4)-alkylthio-(C1 -C4)-alkyl, (C1 -C4)-alkyl-amino or di-(C1 -C4)-alkylamino,R3 is hydrogen, (C1 -C4)-alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy, halogen, (C1 -C4)-alkylthio, amino, (C1 -C4)-alkylamino or di-(C1 -C4)-alkyl-amino orR2 and R3 together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered carbocyclic ring which, if it is a 5-membered ring, can contain an oxygen atom in place of CH2 and which 5- or 6-membered ring is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C1 -C4)-alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkyl, (C1 -C4)-haloalkoxy or halogen, or if it is a 5-membered ring, can also contain a sulfur atom in place of CH2 and which ring is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C1 -C6)alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkyl, or (C1 -C4)-haloalkoxy, orR2 and R3 together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered carbocyclic ring which can contain an oxygen or sulfur atom in place of CH2 and which is optionally substituted by 1, 2 or 3 (C1 -C4)-alkyl groups,X is NH or oxygen,E is a direct bond or a straight-chain or branched (C1 -C4)-alkanediyl group,Q has the meaning Q1 andQ1 is a cycloalkyl group of the formula II ##STR272## in which n is an integer from 2 to 7, R4 and R5 are identical or different and are in each case hydrogen, (C1 -C12)-alkyl, (C3 -C8)-cycloalkyl, (C3 -C8)-cycloalkyl-(C1 -C4) -alkyl, (C1 -C4)-alkoxy, (C3 -C8)-cycloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkyl, (C3 -C8)-cycloalkyl-(C1 -C4)-alkoxy, tri-(C1 -C4)-alkylsilyl, di-(C1 -C8)-alkyl-(C3 -C8)-cycloalkyl-silyl, di-(C1 -C8)-alkyl-(phenyl-(C1 -C4)-alkyl)-silyl, di-(C1 -C8)-alkyl-(C1 -C4)-haloalkylsilyl, dimethylphenyl silyl, (C1 -C4)-haloalkyl, halogen, (C1 -C4)-haloalkoxy, phenyl, phenyl-(C1 -C4)-alkyl, benzyloxy, benzyloxy-(C1 -C4)-alkyl, benzylthio, phenylthio or phenoxy, it being possible for the phenyl rings in the seven last-mentioned radicals to be unsubstituted or provided with one or two substituents and these substituents are identical or different and can be in each case (C1 -C8)-alkyl, (C1 -C8)-cycloalkyl, (C1 -C4)-haloalkyl, halogen, (C1 -C4)-dialkylamino, (C1 -C4)-alkylthio, (C1 -C8)-alkoxy, (C1 -C4)-haloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkoxy, H5 C2 --O--[CH2 --CH2 --O]y, 2- (tetrahydro-2H-pyran-2-yloxy)-ethoxy, (C2 -C8)-alkenyl, (C2 -C8)-alkynyl, benzyloxy which in the phenyl radical optionally carries one or two identical or different substituents selected from the group comprising (C1 -C4)-alkyl, (C1 -C4)-haloalkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy and halogen, or tri-(C1 -C4)-alkylsilylmethoxy, (C3 -C8)-cycloalkyl-(C1 -C4)-alkoxy, 1,3 -dioxolan-2-ylmethoxy, tetrahydrofuran-2 -ylmethoxy or tetrahydro-2H-pyran-2-ylmethoxy, where, both R4 and R5 do not coincidentally denote hydrogen, and where, in two adjacent substituents which are identical or different and selected from the group comprising (C1 -C8)-alkyl and (C1 -C8)-alkoxy, in each case one hydrogen atom can be replaced by a joint carbon-carbon bond which links these two substituents, orR4 and R5 together with the cycloalkyl group form a 3-8-membered spirocyclic ring system which can contain oxygen or sulfur in place of one or two CH2 groups orR4 and R5 together with the carbon atoms carrying them form a fused 5- or 6-membered carbocycle,y is 2, 3 or 4, orQ has the meaning Q2 andQ2 is a group of the formula III ##STR273## in which R6 is a group of the formula Z--W and Z is a direct bond or carbonyl or sulfonyl and W is a phenyl, naphthyl, or biphenyl or heteroaryl selected from the group consisting of 2-pyridyl, 2-quinoxalinyl and 2-pyrimidinyl which phenyl, naphthyl, biphenyl or heteroaryl can be unsubstituted or provided with one or two substituents and these substituents are identical or different and are in each case (C1 -C8)-alkyl, (C3 -C8) -cycloalkyl, trifluoromethyl, halogen, (C1 -C4)-alkoxy, (C1 -C4)-dialkylamino or (C1 -C4)-alkylthio, or acid addition salts thereof.
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Accused Products
Abstract
The invention relates to compounds of the formula ##STR1## in which R1, R2, R3 and Q are as defined in the description, X is NH or oxygen and E is a bond or a 1- to 4-membered carbon chain, to a process for their preparation, to agents containing them, and to their use in the control of pests and as fungicides.
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Citations
16 Claims
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1. A compound of the formula I ##STR271## in which R1 is hydrogen, halogen, (C1 -C4)-alkyl or (C3 -C6)-cycloalkyl,
R2 is hydrogen, (C1 -C4)-alkyl, halogen, (C1 -C4)-haloalkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkyl, (C1 -C4)-alkylthio, (C1 -C4)-alkylthio-(C1 -C4)-alkyl, (C1 -C4)-alkyl-amino or di-(C1 -C4)-alkylamino, R3 is hydrogen, (C1 -C4)-alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy, halogen, (C1 -C4)-alkylthio, amino, (C1 -C4)-alkylamino or di-(C1 -C4)-alkyl-amino or R2 and R3 together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered carbocyclic ring which, if it is a 5-membered ring, can contain an oxygen atom in place of CH2 and which 5- or 6-membered ring is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C1 -C4)-alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkyl, (C1 -C4)-haloalkoxy or halogen, or if it is a 5-membered ring, can also contain a sulfur atom in place of CH2 and which ring is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C1 -C6)alkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkyl, or (C1 -C4)-haloalkoxy, or R2 and R3 together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered carbocyclic ring which can contain an oxygen or sulfur atom in place of CH2 and which is optionally substituted by 1, 2 or 3 (C1 -C4)-alkyl groups, X is NH or oxygen, E is a direct bond or a straight-chain or branched (C1 -C4)-alkanediyl group, Q has the meaning Q1 and Q1 is a cycloalkyl group of the formula II ##STR272## in which n is an integer from 2 to 7, R4 and R5 are identical or different and are in each case hydrogen, (C1 -C12)-alkyl, (C3 -C8)-cycloalkyl, (C3 -C8)-cycloalkyl-(C1 -C4) -alkyl, (C1 -C4)-alkoxy, (C3 -C8)-cycloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkyl, (C3 -C8)-cycloalkyl-(C1 -C4)-alkoxy, tri-(C1 -C4)-alkylsilyl, di-(C1 -C8)-alkyl-(C3 -C8)-cycloalkyl-silyl, di-(C1 -C8)-alkyl-(phenyl-(C1 -C4)-alkyl)-silyl, di-(C1 -C8)-alkyl-(C1 -C4)-haloalkylsilyl, dimethylphenyl silyl, (C1 -C4)-haloalkyl, halogen, (C1 -C4)-haloalkoxy, phenyl, phenyl-(C1 -C4)-alkyl, benzyloxy, benzyloxy-(C1 -C4)-alkyl, benzylthio, phenylthio or phenoxy, it being possible for the phenyl rings in the seven last-mentioned radicals to be unsubstituted or provided with one or two substituents and these substituents are identical or different and can be in each case (C1 -C8)-alkyl, (C1 -C8)-cycloalkyl, (C1 -C4)-haloalkyl, halogen, (C1 -C4)-dialkylamino, (C1 -C4)-alkylthio, (C1 -C8)-alkoxy, (C1 -C4)-haloalkoxy, (C1 -C4)-alkoxy-(C1 -C4)-alkoxy, H5 C2 --O--[CH2 --CH2 --O]y, 2- (tetrahydro-2H-pyran-2-yloxy)-ethoxy, (C2 -C8)-alkenyl, (C2 -C8)-alkynyl, benzyloxy which in the phenyl radical optionally carries one or two identical or different substituents selected from the group comprising (C1 -C4)-alkyl, (C1 -C4)-haloalkyl, (C1 -C4)-alkoxy, (C1 -C4)-haloalkoxy and halogen, or tri-(C1 -C4)-alkylsilylmethoxy, (C3 -C8)-cycloalkyl-(C1 -C4)-alkoxy, 1,3 -dioxolan-2-ylmethoxy, tetrahydrofuran-2 -ylmethoxy or tetrahydro-2H-pyran-2-ylmethoxy, where, both R4 and R5 do not coincidentally denote hydrogen, and where, in two adjacent substituents which are identical or different and selected from the group comprising (C1 -C8)-alkyl and (C1 -C8)-alkoxy, in each case one hydrogen atom can be replaced by a joint carbon-carbon bond which links these two substituents, or R4 and R5 together with the cycloalkyl group form a 3-8-membered spirocyclic ring system which can contain oxygen or sulfur in place of one or two CH2 groups or R4 and R5 together with the carbon atoms carrying them form a fused 5- or 6-membered carbocycle, y is 2, 3 or 4, or Q has the meaning Q2 and Q2 is a group of the formula III ##STR273## in which R6 is a group of the formula Z--W and Z is a direct bond or carbonyl or sulfonyl and W is a phenyl, naphthyl, or biphenyl or heteroaryl selected from the group consisting of 2-pyridyl, 2-quinoxalinyl and 2-pyrimidinyl which phenyl, naphthyl, biphenyl or heteroaryl can be unsubstituted or provided with one or two substituents and these substituents are identical or different and are in each case (C1 -C8)-alkyl, (C3 -C8) -cycloalkyl, trifluoromethyl, halogen, (C1 -C4)-alkoxy, (C1 -C4)-dialkylamino or (C1 -C4)-alkylthio, or acid addition salts thereof.
Specification
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- Resources
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Current AssigneeHoechst Aktiengesellschaft (Sanofi )
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Original AssigneeHoechst Aktiengesellschaft (Sanofi )
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InventorsBraun, Peter, Knauf, Werner, Schaper, Wolfgang, Kern, Manfred, Waltersdorfer, Anna, Preuss, Rainer, Sachse, Burkhard, Bonin, Werner, Salbeck, deceased, Gerhard, L ummen, Peter
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Primary Examiner(s)Ford, John M.
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Application NumberUS08/029,889Time in Patent Office1,335 DaysField of Search544/298, 544/319, 544/326, 544/327, 544/229, 544/296, 544/278, 544/283, 544/284, 544/287, 544/289, 514/256, 514/269, 514/63, 514/249US Class Current514/269CPC Class CodesA01N 43/54 1,3-Diazines; Hydrogenated ...A01N 43/90 having two or more relevant...C07D 239/34 One oxygen atomC07D 239/42 One nitrogen atom nitro rad...C07D 239/47 One nitrogen atom and one o...C07D 239/52 Two oxygen atomsC07D 239/88 Oxygen atomsC07D 239/94 Nitrogen atomsC07D 401/12 linked by a chain containin...C07D 405/12 linked by a chain containin...C07D 495/04 Ortho-condensed systems
