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US 12,604,895 B2Granted
Pesticidally active cyclic amine compounds
AssigneeSyngenta Crop Protection AG
InventorsOttmar Franz Hueter, Caroline Chenel, Pierre Joseph Marcel Jung, Elke Maria Hillesheim, Ruifang Chen, Hua Li, Long Lu
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
Claims17
A compound of formula (I)
- wherein
- R1 is CN, C(═S)NH2 or C1-C6-haloalkyl;
- R2 is H, OH, halogen, C1-C6-alkoxy or C1-C6-haloalkoxy;
- R3 is H, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, or C1-C6-haloalkyoxy;
- R4 is H, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, or C1-C6-haloalkyoxy;
- R5 is phenyl or phenyl substituted with 1 to 3 substituents R6;
- Q is a cyclic amine represented by formula Ila or a cyclic amine represented by formula IIb,
- wherein the arrow indicates the connection to the carbonyl group;
- p1 and p2 are each 0, or p1 and p2 are each 1;
- q1 is 1 or 2 and indicates the number of methylene groups;
- q2 is 1 or 2 and indicates the number of methylene groups;
- X is hydrogen, hydroxyl, C1-C6-alkoxy, cyano or halogen;
- Y is cyano, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylsulfanyl-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-alkenylsulfanyl-C1-C6-alkyl, C3-C6-alkenylsulfinyl-C1-C6-alkyl, C3-C6-alkenylsulfonyl-C1-C6-alkyl, C3-C6-alkynylsulfanyl-C1-C6-alkyl, C3-C6-alkynylsulfinyl-C1-C6-alkyl, C3-C6-alkynylsulfonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonylamino, RaRbNC(O), RcC(O) NRd, ReSO2NRf, RgO—N═CRh, 4 to 6 membered non-aromatic heterocyclic ring system in which one or two carbons are replaced independently by nitrogen, oxygen, sulfur, or sulfonyl, phenyl, phenyl substituted with 1 to 3 substituents R8, 5 or 6 membered monocyclic heteroaryl, or 5 or 6 membered monocyclic heteroaryl substituted with 1 to 3 substituents R9;
- or
- X and Y together form a double bond to a nitrogen which is substituted with a group RmO;
- A is cyano, C1-C6-cyanoalkyl, C2-C6-cyanoalkenyl, C3-C6-cyanocycloalkyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-halocycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-alkylsulfanyl-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, RiSO2, RjRkNSO2, phenyl, phenyl substituted with 1 to 3 substituents R10, heteroaryl (which is either a 5 or 6 membered monocyclic or a 9 or 10 membered bicyclic), or heteroaryl (which is either a 5 or 6 membered monocyclic or a 9 or 10 membered bicyclic) substituted with 1 to 3 substituents R11;
- Ra and Rb are independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl and C1-C6-alkylsulfonyl;
- Rc and Rd are independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl;
- Rf is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;
- Re and Ri are independently selected from C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl;
- Rg and Rh are independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl;
- Rj and Rk are independently selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl;
- Rm is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;
- and
- R6, R8, R9, R10, R11 are independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfanyl;
- or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula I.
23 more elements
A compound selected from any one in Tables P1-P8:
- TABLE P1
- Comp.
- No
- Y
- R3
- P1.1
- 5-methyl-1,2,4-
- CF3
- oxadiazole-3-yl
- P1.2
- CH2SCH2CH3
- CF3
- P1.3
- CH2S(═O)CH2CH3
- CF3
- P1.4
- CH2SO2CH2CH3
- CF3
- P1.5
- 1,1-dioxo-1,2-
- CF3
- thiazolidin-2-yl
- P1.6
- 5-methyl-1,2,4-
- CH3
- oxadiazole-3-yl
- P1.7
- CH2SCH2CH3
- CH3
- P1.8
- 1,1-dioxo-1,2-
- CH3
- thiazolidin-2-yl
- P1.9
- 5-methyl-1,2,4-
- H
- oxadiazole-3-yl
- P1.10
- CH2SCH2CH3
- H
- P1.11
- 1,1-dioxo-1,2-
- H
- thiazolidin-2-yl
- P1.12
- CH2SCH3
- CF3
- P1.13
- CH2S(═O)CH3
- CF3
- P1.14
- CH2SO2CH3
- CF3
- P1.15
- CH2SCH2CH═CH2
- CF3
- P1.16
- CH2S(═O)CH2CH═CH2
- CF3
- P1.17
- CH2SO2CH2CH═CH2
- CF3
- P1.18
- CH2SCH2CHCH
- CF3
- P1.19
- CH2S(═O)CH2CHCH
- CF3
- P1.20
- CH2SO2CH2CHCH
- CF3
- P1.21
- CH2SCH2CH2CH3
- CF3
- P1.22
- CH2S(═O)CH2CH2CH3
- CF3
- P1.23
- CH2SO2CH2CH2CH3
- CF3
- P1.24
- CH2SCH3
- CH3
- P1.25
- CH2S(═O)CH3
- CH3
- P1.26
- CH2SO2CH3
- CH3
- P1.27
- CH2SCH2CH═CH2
- CH3
- P1.28
- CH2S(═O)CH2CH═CH2
- CH3
- P1.29
- CH2SO2CH2CH═CH2
- CH3
- P1.30
- CH2SCH2CHCH
- CH3
- P1.31
- CH2S(═O)CH2CHCH
- CH3
- P1.32
- CH2SO2CH2CHCH
- CH3
- P1.33
- CH2SCH2CH2CH3
- CH3
- P1.34
- CH2S(═O)CH2CH2CH3
- CH3
- P1.35
- CH2SO2CH2CH2CH3
- CH3
- P1.36
- (E)-N-methoxy-imino-
- CF3
- methyl
- P1.37
- (E)-N-ethoxy-imino-
- CF3
- methyl
- P1.38
- methylsulfonyl-
- CF3
- carbamoyl
- P1.39
- dimethylcarbamoyl
- CF3
- P1.40
- ethyl(methyl)carbamoyl
- CF3
- P1.41
- methanesulfonamido
- CF3
- P1.42
- ethanesulfonamido
- CF3
- P1.43
- 5-methyl-1,2,4-
- OCH3
- oxadiazole-3-yl
- P1.44
- CH2SCH2CH3
- OCH3
- P1.45
- 5-methyl-1,2,4-
- OCH2CH3
- oxadiazole-3-yl
- P1.46
- CH2SCH2CH3
- OCH2CH3
- P1.47
- ethoxycarbonyl
- CF3
- P1.48
- tert-butoxy-
- CF3
- carbonylamino
- P1.49
- trifluoromethyl-
- CF3
- sulfonylamino
- P1.50
- 1-methyl-1,2,4-triazol-
- CF3
- 3-yl
- P1.51
- phenyl
- CF3
- P1.52
- ethoxymethyl
- CF3
- P1.53
- cyano
- CF3
- TABLE P2
- Comp.
- No
- A
- R3
- P2.1
- 3,5-dichloro-2-pyridyl
- CF3
- P2.2
- 3,5-dichloro-2-pyridyl
- CH3
- P2.3
- 3,5-dichloro-2-pyridyl
- H
- P2.4
- 3,5-dichloro-2-pyridyl
- OCH3
- P2.5
- 3,5-dichloro-2-pyridyl
- OCH2CH3
- P2.6
- cyano
- CF3
- P2.7
- CH2CN
- CF3
- P2.8
- CH2CH2CN
- CF3
- P2.9
- 2,2,2-trifluoroethyl
- CF3
- P2.10
- 3,3-dichloroallyl
- CF3
- P2.11
- CH2CH2SCH3
- CF3
- P2.12
- CH2CH2S(═O)CH3
- CF3
- P2.13
- methylsulfonyl
- CF3
- P2.14
- trifluoromethyl-
- CF3
- sulfonyl
- P2.15
- tert-butoxy-carbonyl
- CF3
- P2.16
- trifluoromethyl-
- CF3
- carbonyl
- P2.17
- methoxyethyl
- CF3
- TABLE P3
- Comp.
- No
- Y
- R3
- P3.1
- CH2SCH3
- CF3
- P3.2
- CH2S(═O)CH3
- CF3
- P3.3
- CH2SO2CH3
- CF3
- P3.4
- CH2SCH2CH3
- CF3
- P3.5
- CH2S(═O)CH2CH3
- CF3
- P3.6
- CH2SO2CH2CH3
- CF3
- P3.7
- CH2S(═O)CH2CH2CH3
- CF3
- P3.8
- CH2SO2CH2CH2CH3
- CF3
- P3.9
- CH2SCH2CH2CH3
- CF3
- Table P4:
- TABLE P4
- Comp. No
- Rm
- R3
- P4.1
- methyl
- CF3
- P4.2
- ethyl
- CF3
- ;
- Table P5:
- TABLE P5
- Comp. No
- Y
- X
- R3
- P5.1
- phenyl
- OH
- CF3
- P5.2
- 4-Cl-phenyl
- OH
- CF3
- P5.3
- 4-Cl-phenyl
- OCH3
- CF3
- ;
- Table P6:
- TABLE P6
- Comp. No
- Y
- R3
- P6.1
- 5-methyl-1,2,4-
- CH3
- oxadiazole-3-yl
- ;
- Table P7:
- TABLE P7
- Comp. No
- A
- R3
- P7.1
- 3,5-dichloro-2-
- CH3
- pyridyl
- ;
- and
- Table P8:
- TABLE P8
- Comp. No
- A
- R3
- P8.1
- 3,5-dichloro-2-
- CH3
- pyridyl
- .
327 more elements
Dependencies are inferred from the claim text.