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US 6,274,613 B1Granted
Cyclic imines as pesticides
AssigneeBayer Aktiengesellschaft
InventorsAndrew Plant, Gerd Kleefeld, Thorsten Pötter, Christoph Erdelen, Norbert Mencke, Andreas Turberg, Ulrike Wachendorff-Neumann
Life of this patent
Estimating the term…
Abstract
The invention relates to novel cyclic imines of the formula (I) in which Ar1 and Ar2 each represent substituted phenyl and n represents 1, to a process for their preparation and to their use as pesticides.
Claims9
Compounds of the formula (I)
- in which
- n represent 1
- Ar1 represents the radical
- and
- Ar2 represents the radical
- in which
- m represents 0, 1, 2, 3 or 4,
- R1 represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkyl, —S(O)oR6 or —NR7R8,
- R2 and R3 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkyl, —S(O)oR6 or —NR7R8,
- R4 represents halogen, cyano, trialkylsily, —CO—NR10R11, tetrahydropyranyl or one of the groupings below
- (l) —X—A
- (m) —B—Z—D
- (n) —Y—E,
- R5 represents hydrogen, halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkoxyalkoxy or —S(O)oR6,
- o represents 0, 1 or 2,
- R6 represents alkyl or halogenoalkyl,
- R7 and R8 independently of one another each represent hydrogen or alkyl, or together represent alkylene,
- R10 and R11 independently of one another each represent hydrogen, alkyl, halogenoalkyl or represent phenyl or phenylalkyl, each of which is optionally mono- or polysubstituted by radicals from the list W1,
- X represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or di-alkylsilylene,
- A represents phenyl, naphthyl or tetrahydronaphthyl, each of which is optionally mono or polysubstituted by radicals from the list W1, or represents 5- to 10-membered heterocyclyl having one or more hetero atoms from the group consisting of nitrogen, oxygen and sulphur and containing 1 or 2 aromatic rings, which is optionally mono- or polysubstituted by radicals from the list W2,
- B represents p-phenylene which is optionally mono- or disubstituted by radicals from the list W1,
- Z represents oxygen or sulphur,
- D represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, respectively optionally halogen-, alkyl-, alkenyl-, halagenoalkenyl-, phenyl-, styryl-, halogenophenyl- or halogenostyryl-substituted cycloalkyl or cycloalkylalkyl, represents respectively optionally halogen- or alkyl-substituted cycloalkenyl or cycloalkenylalkyl, represents respectively optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenylalkyl, naphthylalkyl, tetrahydronaphthylalkyl or 5- or 6-membered hetarylalkyl having 1 or 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, represents —CO—R12, —CO—NR13R14 or represents the grouping
- —(CH2)p—(CR15R16)q—(CH2)r—G, or
- Z and D together represent optionally, nitro-, halogen-, alkyl, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenoxyalkyl,
- Y represents a direct bond, oxygen, sulphur, carbonyl, carbonyloxy, oxycarbonyl, alkylene, alkenylene, alkinylene, alkyleneoxy, oxyalkylene, thioalkylene, alkylenedioxy or represents p-phenylene which is optionally moon- or disubstituted by radicals from the list W1,
- E represents hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkenyl-, phenyl-, styryl-, halogenophenyl or halogenostyryl-substituted cycloalkyl, represents respectively optionally halogen- or alkyl-substituted cycloalkenyl, represents phenyl which is optionally mono- to tetrasubstituted by radicals from the list W1 or represents a 5- or 6-membered hotaryl having 1 or 2 hetero atoms from the group consisting of nitrogen, oxygen and sulphur, which is optionally mono- to tetrasubstituted by radicals from the list W2, or represents the grouping
- —(CH2)p—(CR15R16)q—(CH2)r—G,
- R12 represents alkyl, alkoxy, alkenyl, alkenyloxy, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyloxy or represents respectively optionally nitro-, halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or naphthyl,
- R13 represents hydrogen or alkyl,
- R14 represents alkyl, halogenoalkyl, respectively optionally halogen-, alkyl-, alkenyl-, halogenoalkyl- or halogenoalkenyl-substituted cycloalkyl, cycloalkylalkyl or represents respectively optionally halogen-, alkyl-, alkoxy-, halogenoalkyl- or halogenoalkoxy-substituted phenyl or phenylalkyl,
- p, q and r independently of one another each represent 0, 1, 2 or 3, their sum being smaller than 6,
- R15 and R16 independently of one another each represent hydrogen or alkyl,
- G represents cyano, represents a 5- or 6-membered heterocycle having 1 to 3 identical or different hetero atoms from the group consisting of nitrogen, oxygen and sulphur, which is optionally substituted by halogen, alkyl or halogenoalkyl and, at the attachment point, optionally by the radical R17, or represents one of the groupings below
- (a) —CO—R17
- (b) —CO—OR18
- (c) —CO—NR19R20
- (d) —CS—NR19R20
- R17 represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl, or represents phenyl which is optionally mono- to pentasubstituted by alkylcarbonylamino, alkylcarbonylalkylamino and/or radicals from the list W3,
- R18 represents hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represents arylalkyl which is optionally mono to pentasubstituted by radicals from the list W3,
- R19 and R20 independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl, represent aryl or arylalkyl, each of which is optionally mono- to pentasubstituted by radicals from the list W3, represent —OR18 or —NR17R18 or together represent an alkylene chain having 2 to 6 members in which one methylene group is optionally replaced by oxygen,
- R21 represents —OR18, —NR17R19 or —N(R17)—COOR18,
- R22, R23 and R24 Independently of one another each represent alkyl,
- W1 represents hydrogen, halogen, cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio or —S(O)oR6,
- W2 represents halogen cyano, formyl, nitro, alkyl, trialkylsilyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkylcarbonyl, alkoxycarbonyl, pentafluorothio or —S(O)oR6 or —C(H17)═N—R21,
- W3 represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino —S(O)oR6, —COOR26 or —CONR26R27,
- R25 represents hydrogen, alkyl, halogenoalkyl, optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or represents phenyl which is optionally mono- to pentasubstituted by radicals from the list W4,
- R26 and R27 independently of one another each represent hydrogen, alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxy, respectively optionally halogen-, alkyl- or halogenoalkyl-substituted cycloalkyl or cycloalkylalkyl or represent aryl or arylalkyl, each of which is optionally mono- to pentasubstituted by radicals from the list W4, represent OR22 or —NR23R24 or together represent an alkylene chain having 2 to 6 members in which one methylene group is optionally replaced by oxygen, and
- W4 represents halogen, cyano, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, dialkylamino, alkoxycarbonyl, dialkylaminocarbonyl or —S(O)oR6;
- provided that if Y represents a direct bond, E cannot be hydrogen.
47 more elements
Dependencies are inferred from the claim text.