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US 10,093,662 B2Granted
Azoline compounds substituted by a condensed ring system
AssigneeBASF SE
InventorsPascal Bindschaedler, Gopal Krishna Datta, Wolfgang von Deyn, Matthias Pohlman, Franz-Josef Braun
Life of this patent
Estimating the term…
Abstract
Compounds of formula I are provided herein, as well as the use of these compounds for controlling invertebrate pests. Plant propagation material and agricultural and veterinary compositions including these compounds are also provided. Compounds for use as intermediate compounds in the preparation of the compounds of formula I are also described.
Claims26
A compound of formula (I)
- wherein
- X1 is O or CH2;
- A is a group A1 or A2;
- wherein
- A1 is a group of following formula:
- wherein
- # denotes the bond to an aromatic ring of formula (I);
- and
- W is selected from the group consisting of O and S;
- and
- A2 is a group —C(R7a)(R7b)—N(R52)—C(═O)—R62
- B1, B2, B3, B4 and B5 are independently selected from the group consisting of N and CR2, wherein at most one of B1, B2, B3, B4 and B5 is N;
- Rg1 and Rg2 form together a bridging group selected from the group consisting of —CH2CH2O—, —OCH2CH2—, —CH2OCH2—, —OCH2O—, —CH2CH2S(O)p—, —S(O)pCH2CH2—, —CH2S(O)pCH2—, —S(O)pCH2S(O)p—, —OCH2S(O)p—, —S(O)pCH2O—, —OCH2CH2CH2—, —CH2CH2CH2O—, —CH2OCH2CH2—, —CH2CH2OCH2—, —OCH2CH2O—, —OCH2OCH2—, —CH2OCH2O—, —S(O)pCH2CH2CH2—, —CH2CH2CH2S(O)p−, —CH2S(O)pCH2CH2—, —CH2CH2S(O)pCH2—, —S(O)pCH2CH2S(O)p—, —S(O)pCH2S(O)pCH2—, —CH2S(O)pCH2S(O)p—, —S(O)pCH2CH2O—, —OCH2CH2S(O)p—, —S(O)pCH2OCH2—, —OCH2S(O)pCH2—, —CH2OCH2S(O)p— and —CH2S(O)pCH2O-;
- wherein p is one of 0, 1 and 2,
- wherein each hydrogen atom of the bridging group is optionally replaced by a substituent independently selected from the group consisting of:
- halogen, methyl, halogenated methyl, hydroxyl, methoxy and halogenated methoxy;
- and wherein 0, 1, or 2 CH2 groups of the bridging group are replaced by a C═O group;
- R1 is C1-haloalkyl;
- each R2 is independently selected from the group consisting of hydrogen, halogen, C1-C2-haloalkoxy, and C1-C2-haloalkyl;
- R3a and R3b, independently of each other, are selected from the group consisting of hydrogen and halogen;
- R7a and R7b, independently of each other, are selected from the group consisting of hydrogen, cyano, methyl, and C1-haloalkyl;
- R51 and R52, independently of each other, are selected from the group consisting of hydrogen, C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C6-alkoxymethyl, and CH2—CN;
- R61 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl carrying one or two radicals R81, C1-C6-haloalkyl carrying one radical R81, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl carrying 1 or 2 CN substituents, C3-C6-halocycloalkyl, —N(R101a)R101b, —CH═NOR91, phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R16;
- and a heterocyclic ring selected from rings E-1 to E-63
- wherein in rings E-1 to E-63
- the zigzag line denotes an attachment point to the remainder of the molecule;
- k is 0, 1, 2 or 3;
- n is 0, 1 or 2;
- and
- R16 is as defined below;
- R62 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkyl substituted by one or two radicals R82, C1-C6-haloalkyl carrying one radical R82, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl carrying a CN substituent, C3-C6-halocycloalkyl, —N(R102a)R102b, —C(═O)N(R112a)R112b, —CH═NOR92, phenyl, phenyl substituted with 1, 2, 3, 4, or 5- substituents R16;
- and a heterocyclic ring selected from rings of formulae E-1 to E-63 as defined above;
- each R81 is independently selected from the group consisting of OH, CN, C3-C8-cycloalkyl, C3-C8-cycloalkyl carrying a CN substituent, C3-C8-cycloalkyl carrying a C1-haloalkyl substituent, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —C(═O)N(R101c)R101d, phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R16;
- and a heterocyclic ring selected from rings E-1 to E-63 as defined above;
- each R82 is independently selected from the group consisting of OH, CN, C3-C6-cycloalkyl, C3-C6-cycloalkyl carrying a CN substituent, C3-C6-cycloalkyl carrying a C1-haloalkyl substituent, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —C(═O)N(R102c)R102d, phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R16;
- and a heterocyclic ring selected from rings E-1 to E-63 as defined above;
- R91 and R92, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, and C1-C6-haloalkyl;
- R101a, R102a, R102c and R112a, independently of each other, are selected the group consisting of from hydrogen and C1-C6-alkyl;
- R101b is selected from the group consisting of hydrogen, —C(═O)N(R14a)R14b, phenyl, phenyl substituted 1, 2, 3, 4, or 5 substituents R16;
- and a heterocyclic ring selected from rings of formulae E-1 to E-42 as defined above;
- R102b is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, CH2—CN, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkylmethyl, phenyl, phenyl substituted with 1, 2, 3, 4, or 5 substituents R16;
- and a heterocyclic ring selected from rings of formulae E-1 to E-42 as defined above;
- R101c is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C3-alkynyl, and CH2—CN;
- R101d is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, CH2—CN, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, C3-C6-halocycloalkylmethyl, C1-C6-alkoxy, C1-C6-haloalkoxy, phenyl, phenyl having 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of halogen, cyano, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, and C1-C4-haloalkylthio;
- and a heterocyclic ring selected from rings of formulae E-1 to E-63 as defined above;
- R102d and R112b, independently of each other, are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl carrying a CN substituent, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, and C3-C6-halocycloalkylmethyl;
- R14a is selected from the group consisting of hydrogen and C1-C6-alkyl;
- R14b is selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, CH2—CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
- and
- each R16 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl-C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, and di-(C1-C4-alkyl)aminocarbonyl;
- or
- two R16 present on the same carbon atom of a saturated ring may form together ═O or ═S;
- or
- two R16 present on the same S or SO ring member of a heterocyclic ring may together form a group ═N(C1-C6-alkyl), ═NO(C1-C6-alkyl), ═NN(H)(C1-C6-alkyl) or ═NN(C1-C6-alkyl)2;
- or an N-oxide, stereoisomer, or an agriculturally or veterinarily acceptable salt thereof.
52 more elements
Dependencies are inferred from the claim text.