http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-119426-A1

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filingDate 2020-07-17-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ff0eef2715ee6481189b2b98f3682c12
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publicationDate 2021-12-15-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-119426-A1
titleOfInvention 5-AMINO PYRAZOLES AND TRIAZOLES AS PESTICIDES
abstract 1,2-diazole and 1,2,4-triazole derivatives as pesticides; formulations that comprise them and their use for the control of animal pests, in particular insects, arachnids or nematodes. These compounds are also used in the protection of seeds or plants. Claim 1: Compound of the formula (1) in which Ar represents phenyl or a 5- or 6-membered heteroaromatic ring, in each case unsubstituted or substituted with 1 to 4 RAʳ; where each RAʳ considered independently of the others represents halogen, cyano, nitro, SF₅, C(Q¹)Rᵃ, C(O)ORᵃ, C(Q¹)NRᵇRᶜ, NRᵈRᵉ, ORᵃ, S(O)ₙRᵃ or SO₂NRᵇRᶜ; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, all of which may in each case be unsubstituted or mono- to trideca-substituted with halogen and/or optionally with 1 to 3Rᶠ; or represents phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered heteroaromatic ring system, each of which is in each occurrence unsubstituted or substituted with 1 to 3 Rᵍ; A represents N or CRA; where RA represents H, halogen, cyano, nitro, SF₅, C(Q¹)Rᵃ, C(O)ORᵃ, C(Q¹)NRᵇRᶜ, NRᵈRᵉ, ORᵃ, S(O)ₙRᵃ or SO₂NRᵇRᶜ; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, all of which may in each case be unsubstituted or mono- to trideca-substituted with halogen and/or optionally with 1 to 3Rᶠ; or represents phenyl, a 5- or 6-membered heteroaromatic ring or a 7- to 11-membered aromatic heterocyclic ring system, each of which is in each case unsubstituted or substituted with 1 to 3 Rᵍ; R¹ represents -NR¹¹R¹², -N(Rᵇ)NRᵈRᵉ, -N(Rᵇ)ORᵃ, -N(Rᵇ)-CN, -N(R¹¹)C(Q¹)Rᵇ, -N(R¹¹)C(Q¹)NRᵇRᶜ, - N(R¹¹)C(O)ORᵃ, -N(R¹¹)C(O)C(O)Rᵇ, -N(R¹¹)C(O)C(O)ORᵃ, -N(R¹¹)C(O)C (O)NRᵇRᶜ, -N(R¹¹)SO₂Rᵃ, -N=C(Rᵇ)N(Rᵇ)(Rᶜ), -N=C(Rᵇ)(Rᶜ), -N=S(O)RᵃRᵃ or -N= SSRᵃRᵃ; where R¹¹ represents H; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, all of which may in each case be unsubstituted or mono- to penta-substituted with halogen and/or optionally with 1 to 2Rʰ; or represents phenyl or represents a saturated, partially saturated or aromatic 4- to 7-membered heterocycle having 1 to 3 heteroatoms, in each case unsubstituted or substituted with 1 to 5 Rᵍ; R¹² represents H; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, each of which in each case is unsubstituted or substituted with 1 to 5 Rᵍ; or R¹¹ and R¹² together with the nitrogen atom to which they are attached represent an optionally substituted saturated, partially saturated or aromatic heterocycle having from 3 to 7 ring atoms and may optionally be interrupted with other heteroatoms and/or one or two groups C=O; R² represents the substructure of the general formula -X-Y-Z, where X represents phenyl or a 5- or 6-membered heteroaromatic ring, each of which is in each case unsubstituted or substituted with 1 to 3 RX; where each RX considered independently of the others represents halogen, cyano, nitro, C(Q¹)Rᵃ, C(O)ORᵃ, C(Q¹)NRᵇRᶜ, NRᵈRᵉ, ORᵃ, S(O)ₙRᵃ or SO₂NRᵇRᶜ; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, each of which in each case is unsubstituted or substituted with 1 to 7 Rᶠ; Y represents -CRY¹=N-, where N is linked to Z, or represents -NRY²-C(=QY)-, where C is linked to Z; where RY¹ and RY² each represent H; or represent C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, each of which is in each case unsubstituted or substituted by 1 to 7 RY¹¹; where each RY¹¹ taken independently of the others represents halogen, cyano, C₁₋₄-alkyl, C₃₋₆-cycloalkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy or C₁₋₄-haloalkoxy; QY represents O or S; Z represents the fragments of the general formula (A1), (A2), (A3) or (A4), of the group of formulas (2); where # is the attachment point to Y and where each T represents O or S; RZ¹ considered independently of the others represents a 5- to 10-membered aromatic or heteroaromatic ring or bicyclic ring system, in each case unsubstituted or substituted with 1 to 4 RZ¹¹; where each RZ¹¹ considered independently of the others represents halogen, cyano, nitro, SF₅, C(Q¹)Rᵃ, C(O)ORᵃ, C(Q¹)NRᵇRᶜ, NRᵈRᵉ, ORᵃ, S(O)ₙRᵃ or SO₂NRᵇRᶜ; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, each of which in each case is unsubstituted or substituted with 1 to 5 RZ¹ᵃ; or represents phenyl or a 5- or 6-membered heteroaromatic ring, each of which is in each occurrence unsubstituted or substituted by 1 to 3 RZ¹ᵃ; or two adjacent RZ¹¹ together form a straight chain C₃₋₅-alkylene group which is unsubstituted or substituted with 1 to 6 RZ¹ᵃ, where considering each independently of the others one CH₂ unit may be replaced by carbonyl and 1 to 2 CH₂ units can be replaced with O, S, NH or N(CH₃); where each RZ¹ᵃ represents halogen, cyano, C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-thioalkyl, C₁₋₄-haloalkyl or C₁₋₄-haloalkoxy; RZ², RZ²ᵃ and RZ³ considering each independently of the others represent H; or represent C(O)Rᵃ, C(O)ORᵃ, C(O)NRᵇRᶜ, S(O)ₙRᵃ; or represent C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl, each of which is in each case unsubstituted or substituted by 1 to 5 RZ²¹; or represents phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each of which is in each case unsubstituted or substituted by 1 to 4 RZ²¹; where each RZ²¹ considered independently of the others represents halogen, cyano, nitro, SF₅, C(Q¹)Rᵃ, C(O)ORᵃ, C(Q¹)NRᵇRᶜ, NRᵈRᵉ, ORᵃ, S(O)ₙRᵃ or SO₂NRᵇRᶜ; or represents C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl or C₃₋₇-cycloalkyl; o RZ² and RZ³ together with the T-C-N unit form a ring of 5 to 7 members; where the RZ²-RZ³ ring members consist of carbon atoms and optionally 1 oxygen or sulfur or nitrogen atom; where the heteroatom is not directly attached to T; where up to 2 ring member carbon atoms considering each independently of the others may consist of C(=O) and C(=S) and the ring member sulfur atom may consist of S, S(O) or S( O)₂; where this RZ²-RZ³ unit is unsubstituted or substituted with 1 to 5 RZ²¹; where each RZ²¹ considered independently of the others represents halogen, cyano, C₁₋₆-alkyl, C₃₋₆-cycloalkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy or C₁₋₆-haloalkoxy; o RZ²ᵃ and a second RZ²ᵃ together with the N-C-N unit form a ring of 5 to 7 members; where the ring members RZ²ᵃ-RZ²ᵃ consist of carbon atoms and up to 2 heteroatoms which considering each independently of the others can be selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms; where up to 2 ring member carbon atoms considering each independently of the others may consist of C(=O) and C(=S) and where the ring member sulfur atom may consist of S, S(O) or S (O)₂; where this RZ²-RZ³ unit is unsubstituted or substituted with 1 to 5 RZ²¹; RZ⁴¹, RZ⁴² and RZ⁴³ each taken independently of the others represent H, halogen or NRᵈRᵉ; or represent C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₃₋₇-cycloalkyl, C₁₋₆-alkoxy, C₂₋₆-alkenyloxy, C₂₋₆-alkynyloxy, C₃₋₇-cycloalkoxy, C₁₋₆-alkylcarbonyloxy, C₂₋₆-alkenylcarbonyloxy or C₃₋₇-cycloalkylcarbonyloxy, each of which is in each occurrence unsubstituted or substituted with 1 to 7 Rᶠ; or one of the radicals RZ⁴¹, RZ⁴² or RZ⁴³ represents oxo; RZ⁴⁴ represents H; or represents C₁₋₆-alkyl, C₁₋₆-alkoxy, C₂₋₆-alkenyloxy, each of which in each occurrence is unsubstituted or substituted with 1 to 5 Rᶠ; where each Q¹ considered independently of the others represents O, S, NORᵃ or NCN; Rᵃ considered independently of the others represents C₁₋₆-alkyl, C₃₋₆-cycloalkyl, C₂₋₆-alkenyl, or C₂₋₆-alkynyl, all of which may in each case be unsubstituted or mono- to trideca-substituted with halogen and/or optionally substituted with 1 to 3 Rᶠ; or represents phenyl, unsubstituted or substituted with 1 to 7 Rᵍ; Rᵇ and Rᶜ considering each independently of the others represent H; or represent C₁₋₆-alkyl, C₃₋₆-cycloalkyl, C₂₋₆-alkenyl or C₂₋₆-alkynyl, each of which is in each case unsubstituted or substituted by 1 to 7 Rᶠ; or represent phenyl, or represent a 5- or 6-membered heteroaromatic ring, each of which is in each case unsubstituted or substituted by 1 to 4 Rᵍ; o Rᵇ and Rᶜ together form a ring of 3 to 7 members; Rᵈ and Rᵉ considering each independently of the others represent H, C(Q¹)Rᵃ, C(O)ORᵃ; or represent C₁₋₆-alkyl, C₃₋₆-cycloalkyl, C₂₋₆-alkenyl or C₂₋₆-alkynyl, each of which is in each case unsubstituted or substituted by 1 to 7 Rᶠ; or represent phenyl, unsubstituted or substituted with 1 to 7 Rᵍ; o Rᵈ and Rᵉ together form a ring of 3 to 7 members; Rᶠ considered independently of the others represents halogen, cyano, nitro, C₃₋₆-cycloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio, C₁₋₄-haloalkylthio, C₁₋₄-alkylsulfinyl , C₁₋₄-haloalkylsulfinyl, C₁₋₄-alkylsulfonyl, C₁₋₄-haloalkylsulfonyl, C₁₋₄-alkylcarbonyl, or C₁₋₄-alkoxycarbonyl; or represents phenyl or a 5- or 6-membered heteroaromatic ring, each of which is in each occurrence unsubstituted or substituted by 1 to 7 Rᵍ; Rᵍ considered independently of the others represents halogen, cyano, nitro, C₁₋₄-alkyl, C₃₋₆-cycloalkyl, C₁₋₄-haloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio , C₁₋₄-haloalkylthio, C₁₋₄-alkylsulfinyl, C₁₋₄-haloalkylsulfinyl, C₁₋₄-alkylsulfonyl, C₁₋₄-haloalkylsulfonyl, C₁₋₄-alkylcarbonyl, or C₁₋₄-alkoxycarbonyl; Rʰ considered independently of the others represents halogen, cyano, nitro, hydroxy, C₃₋₆-cycloalkyl, C₁₋₄-alkoxy, C₃₋₆-cycloalkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio, C₃₋₆ -cycloalkylthio, C₁₋₄-haloalkylthio, C₁₋₄-alkylsulfinyl, C₃₋₆-cycloalkylsulfinyl, C₁₋₄-haloalkylsulfinyl, C₁₋₄-alkylsulfonyl, C₃₋₆-cycloalkylsulfonyl, C₁₋₄-haloalkylsulfonyl, OSO₵Ⴖႇ,N (Rᵇ)(Rᶜ), C(Q¹)NRᵇRᶜ, N(Rᵇ)C(Q¹)Rᵃ, C(O)Rᵃ, C(O)ORᵇ OC(O)Rᵃ; o represents phenyl; or represents a saturated, partially saturated or aromatic 4- to 7-membered heterocycle having 1 to 3 heteroatoms, each of which is in each case unsubstituted or substituted with 1 to 4 Rᵍ; n considered independently of the others represents 0, 1 or 2.
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