Claims
- 1. A phenylacetic acid compound of the formula I where the substituents and the index have the following meanings:X is oxygen or sulfur; R is hydrogen and or C1-C4-alkyl; R1 is hydrogen and C1-C4-alkyl; R2 is cyano, nitro, trifluoromethyl, halogen, C1-C4-alkyl and or C1-C4-alkoxy; m is 0, 1 or 2, it being possible for the R2 radicals to be different if m is 2; R3 is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylamino or di-C1-C4-alkylamino; R4 is C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C1-C4-alkoxy, arylthio, aryl-C1-C4-alkylthio, hetaryl, hetaryloxy, hetaryl-C1-C4-alkoxy, hetarylthio, hetaryl-C1-C4-alkylthio, it being possible for the cyclic radicals in turn to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR6)—An—R7; or C3-C6-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R5 is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the cyclic groups in turn to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)—An—R7; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, it being possible for these radicals to be partly or completely halogenated or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)—An—R7; A is oxygen, sulfur or nitrogen and where the nitrogen carries hydrogen or C1-C6-alkyl; n is 0 or 1; R6 is hydrogen or C1-C6-alkyl and R7 is hydrogen or C1-C6-alkyl, or a salt thereof.
- 2. The compound of the formula I defined in claim 1, whereinR3 is hydrogen, hydroxyl, cyclopropyl, halogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio, and R5 is hydrogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkylcarbonyl, C2-C10-alkenylcarbonyl, C3-C10-alkynylcarbonyl or C1-C10-alkylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it being possible for the aromatic and heteroaromatic radicals, in turn, to be partly or completely halogenated and/or to carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, halogen, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR6)—An—R7; or aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, it being possible for these groups to be partly or completely halogenated or to carry one to 3 of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR6)—An—R7; or a salt thereof.
- 3. The compound of the formula I defined in claim 1, wherein m is 0.
- 4. The A compound of the formula I defined in claim 1, wherein R1 is methyl.
- 5. The compound defined in claim 1, wherein R4 denotes C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: cyano, hydroxyl, halogen, C1-C6-alkoxy, C3-C6-cycloalkyl, heterocyclyl, aryl, aryloxy, hetaryl and hetaryloxy, or C3-C6-cycloalkyl, which is partly or completely halogenated or carries one to three of the following groups: halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy.
- 6. The compound defined in claim 1, wherein R4 denotes C1-C6-alkyl, which is partly or completely halogenated or carries one to three of the following radicals: halogen and C1-C6-alkoxy.
- 7. A process for preparing a compound of the formula I as defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II wherein L1 is a nucleophilically replaceable leaving group, with a hydroxyimine of the formula IIIR5ON═C(R4)—C(R3)═NOH (III).
- 8. A process for preparing a compound of the formula I as defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II with a dihydroxyimine of the formula IVHON═C(R4)—C(R3)═NOH (IV) to give a compound of the formula Vand then reacting V with a compound of the formula VIR5—L2 (VI) wherein L2 is a nucleophilically replaceable leaving group, to give I.
- 9. A process for preparing a compound of the formula I defined in claim 1, wherein R3 is not halogen, which comprises reacting a benzyl compound of the formula II with a carbonylhydroxyimine of the formula VIIO═C(R4)—C(R3)═NOH (VII) to give a compound of the formula VIII then either reacting VIIIa) first with hydroxylamine or its salt and then with a compound of the formula VI R5—L2 (VI) orb) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb R5ONH2 (IXa) R5ONH3⊕Q⊖ (IXb) where Q⊖ is the anion of an acid, to give I.
- 10. A composition against animal pests or harmful fungi, comprising customary additives and an effective amount of a compound of the formula I defined in claim 1.
- 11. A method for controlling animal pests or harmful fungi, which comprises treating the pests or harmful fungi, their environment or the plants, surfaces, materials or spaces to be kept free from said pests or fungi with an effective amount of a compound of the formula I defined in claim 1.
Priority Claims (2)
Number |
Date |
Country |
Kind |
44 03 448 |
Feb 1994 |
DE |
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44 21 182 |
Jun 1994 |
DE |
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Parent Case Info
This is a Divisional Application of application Ser. No. 09/334,385, filed Jun. 16, 1999 (now U.S. Pat. No. 6,100,263), which is a Divisional Application of application Ser. No. 09/015,692, filed Jan. 29, 1998 (now U.S. Pat. No. 5,981,581), which is a Divisional Application of application Ser. No. 08/687,480, filed on Aug. 5, 1996 (now U.S. Pat. No. 5,889,059), which was filed under 35 U.S.C. 371 as a National Stage application of International Application No. PCT/EP 95/00,007, filed on Jan. 3, 1995.
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