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US 9,955,692 B2Granted
Pyrazoles for controlling invertebrate pests
AssigneeBASF SE
InventorsSebastian Soergel, Daniel Saelinger, Birgit Gockel
Life of this patent
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Abstract
The present invention relates to novel pyrazoles of formula I. Moreover, the invention relates to processes and intermediates for preparing the pyrazoles of formula I, and also to active compound combinations comprising them, to compositions comprising them, and to their use for protecting growing plants from attack or infestation by invertebrate pests. Furthermore, the invention relates to methods of applying such compounds. The present invention also relates to seed comprising such compounds.
Claims22
A pyrazole compound of formula I
- wherein
- V is O, S or NR1a, wherein R1a is selected from the group consisting of H, C1-C10-alkyl, C1-C4-haloalkyl, C3-C10-cycloalkyl, C3-C10-cycloalkylmethyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C1-C10-alkoxy-C1-C4-alkyl, ORa, heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, hetaryl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or
- wherein R1a and R4 together with the carbon atom to which R4 is bound and the nitrogen atom to which R1a is bound as well as the nitrogen atom between said carbon atom and said nitrogen atom form a 4- to 8-membered heterocycle, which contains the two nitrogen atoms as heteroatoms, and may further contain 1 or 2 heteroatoms which, independently of each other, are selected from the group consisting of NRB, O, and S, wherein S may be oxidized, and/or wherein the heterocycle may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from RA;
- D is selected from the group consisting of C1-C8-alkylene, C3-C8-cycloalkylene, C3-C8-heterocycloalkylene, C2-C8-alkenylene, C3-C8-cycloalkenylene, C3-C8-heterocycloalkenylene, and C2-C8-alkynylene, wherein D may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from RA;
- U is N or CRU;
- T is S, O or NR1b, wherein R1b is selected from the group consisting of H, C1-C10-alkyl, C1-C4-haloalkyl, C3-C10-cycloalkyl, C3-C10-cycloalkylmethyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C1-C10-alkoxy-C1-C4-alkyl, ORa, heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, hetaryl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- RP1, RP2, RP3, and RU are independently of each other selected from the group consisting of H, halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxy, C1-C3-haloalkoxy, C1-C4-alkylthio, C1-C3-haloalkylthio, C1-C4-alkylsulfinyl, C1-C3-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C3-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C1-C4-alkoxy-C1-C4-alkyl;
- R1 is selected from the group consisting of H, CN, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C5-alkylen-CN, ORa, C1-C5-alkylen-ORa, C(Y)Rb, C1-C5-alkylen-C(Y)Rb, C(Y)ORc, C1-C5-alkylen-C(Y)ORc, S(O)2Rd, NReRf, C1-C5-alkylen-NReRf, C(Y)NRgRh, C1-C5-alkylen-C(Y)NRgRh, S(O)nNReRf, C(Y)NRiNReRf, C1-C5-alkylen-S(O)2Rd, C1-C5-alkylen-S(O)nNReRf, C1-C5-alkylen-C(Y)NRiNReRf, phenyl, heterocyclyl, hetaryl, phenyl-C1-C5-alkyl, C3-C10-cycloalkyl-C1-C5-alkyl, heterocyclyl-C1-C5-alkyl and hetaryl-C1-C5-alkyl wherein the ring of the seven last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals Ry and Rx;
- R2 and R3 are independently of each other selected from the group consisting of H, halogen, CN, NO2, C1-C10-alkyl, C2-C10-alkenyl and C2-C10-alkynyl, wherein the 3 last mentioned radicals may be unsubstituted, may be partially or fully halogenated or may carry 1, 2 or 3 identical or different substituents Rx, or wherein R2 and R3 are further selected from the group consisting of ORa, SRa, C(Y)Rb, C(Y)ORc, S(O)Rd, S(O)2Rd, NReRf, C(Y)NRgRh, heterocyclyl, hetaryl, C3-C10-cycloalkyl, C5-C10-cycloalkenyl and phenyl, wherein the five last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different substituents selected from the radicals Ry and Rx, and wherein
- R4 is selected from the group consisting of H, C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl and C3-C6-cycloalkyl-X, wherein X is selected from the group consisting of O, S, and NRB, wherein the C1-C6-alkyl or C3-C6-cycloalkyl may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from RA;
- and
- R5 is selected from the group consisting of C1-C6-alkyl, C1-C6-alkyl-X, C3-C6-cycloalkyl and C3-C6-cycloalkyl-X, wherein X is selected from the group consisting of O, S, and NRB, wherein the C1-C6-alkyl or C3-C6-cycloalkyl may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from RA, or wherein
- R4 and R5 together with the carbon atom to which they are bound form a 3- to 8-membered, saturated or unsaturated carbo- or heterocycle, which may contain 1, 2, or 3 heteroatoms which, independently of each other, are selected from the group consisting of NRB, O, and S, wherein S may be oxidized and/or wherein the carbo- or heterocycle may be unsubstituted or may be partially or fully substituted by substituents which, independently of each other, are selected from RA;
- and wherein
- RA is selected from the group consisting of halogen, NO2, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, S(O)nRD, ═O, ═S, ═NRC, ═NORC, and ═NSRC;
- or wherein
- two RA bound to the same carbon atom or to adjacent carbon atoms together with the carbon atom(s) to which they are bound form a 3- to 6-membered, saturated or unsaturated carbo- or heterocycle, which may contain 1 or 2 heteroatoms which, independently of each other, are selected from the group consisting of NRB, O, and S, wherein S may be oxidized;
- and wherein
- RB is selected from the group consisting of H, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-alkylcarbonyl, C1-C2-haloalkylcarbonyl, and C1-C2-alkoxycarbonyl;
- RC is selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl;
- RD is selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
- n is 0, 1, or 2;
- Y is O or S;
- Ra, Rb, Rc are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, hetaryl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Rd is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, hetaryl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- and wherein
- Re and Rf are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, heterocyclyl, heterocyclyl-C1-C4-alkyl, heterocyclylcarbonyl, heterocyclylsulfonyl, phenyl, phenylcarbonyl, phenylsulfonyl, hetaryl, hetarylcarbonyl, hetarylsulfonyl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the twelve last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which, independently of each other, are selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- or
- Re and Rf together with the nitrogen atom to which they are bound form a 5- or 6-membered, saturated or unsaturated heterocycle, which may carry a further heteroatom being selected from the group consisting of O, S and N as a ring member atom and wherein the heterocycle may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- and wherein
- Rg and Rh are independently of each other selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, heterocyclyl, heterocyclyl-C1-C4-alkyl, phenyl, hetaryl, phenyl-C1-C4-alkyl and hetaryl-C1-C4-alkyl, wherein the ring in the six last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Ri is selected from the group consisting of H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and phenyl-C1-C4-alkyl wherein the phenyl ring in the two last mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 substituents which are independently of each other selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
- Rx is selected from the group consisting of CN, NO2, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)nRd, S(O)nNReRf, C1-C10-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, 5- to 7-membered heterocyclyl, 5- or 6-membered hetaryl, phenyl, C3-C6-cycloalkoxy, 3- to 6-membered heterocyclyloxy and phenoxy, wherein the last 7 mentioned radicals may be unsubstituted or may carry 1, 2, 3, 4 or 5 identical or different radicals Ry;
- and
- Ry is selected from the group consisting of halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, S(O)nRd, S(O)nNReRf, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C1-C4-alkoxy-C1-C4-alkyl,
- and/or a salt, stereoisomer, tautomer, or N-oxide thereof.
33 more elements
Dependencies are inferred from the claim text.