http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-103266-A1

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filingDate 2015-12-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 2017-04-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-103266-A1
titleOfInvention REPLACED CYCLIC COMPOUNDS WITH A CONDENSED RING SYSTEM TO COMBAT INVERTEBRATE PESTS
abstract Also to the use of these compounds to control pests of invertebrates, plant propagation material and an agricultural and veterinary composition comprising said compounds. Claim 1: Compounds characterized by the formula (1), wherein X¹ is S, O or CH₂; A is a group A¹ or A²; wherein A¹ is a group of the formula (2), where # indicates the bond to the aromatic ring of the formula (1); and W is selected from 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, provided that, at most, one of B¹, B², B³, B⁴ and B⁵ is N; Rᵍ¹ and Rᵍ² together form a bridge group selected from -CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂-, -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 0, 1 or 2, where the hydrogen atoms of the above groups can be replaced by one or more substituents selected from halogen, methyl, halogenated methyl, hydroxyl, methoxy and halogenated methoxy; and / or one or two CH₂ groups of the above groups can be replaced by a group C = O; R¹ is C₁-haloalkyl; each R² is independently selected from the group consisting of hydrogen, halogen, C₁₋₂-haloalkoxy and C₁₋₂-haloalkyl; R³ᵃ and R³ᵇ are independently selected from hydrogen and halogen; R⁷ᵃ and R⁷ᵇ are independently selected from hydrogen, cyano, methyl and C₁-haloalkyl; R⁵¹ and R⁵² are independently selected from the group consisting of hydrogen, C₁₋₃-alkyl, C₂₋₃-alkenyl, C₂₋₃-alkynyl, C₁₋₆-alkoxymethyl and CH₂-CN; R⁶¹ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkyl having one or two radicals R⁸¹, C₁₋₆-haloalkyl having a radical R⁸¹, C₂₋₆- alkenyl, C₂₋₆-haloalkenyl, C₂₋₆ alkynyl, C₃₋₆-cycloalkyl which can be substituted with 1 or 2 CN substituents; C₃₋₆-halocycloalkyl; -N (R¹⁰¹ᵃ) R¹⁰¹ᵇ, -CH = NOR⁹¹, phenyl that can be substituted with 1, 2, 3, 4 or 5 R¹⁶ substituents, and a heterocyclic ring selected from rings E-1 to E-63 of the formula group ( 3), where, in rings E-1 to E-63, the zigzag line indicates the point of attachment to the rest 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, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkyl substituted with one or more radicals R⁸², C₁₋₆-haloalkyl having a radical R⁸², C₂₋₆- alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₂₋₆-haloalkynyl, C₃₋₆-cycloalkyl optionally having a CN substituent, C₃₋₆-halocycloalkyl, -N (R¹⁰²ᵃ) R¹⁰²ᵇ, -C (= O ) N (R¹¹²ᵃ) R¹¹²ᵇ, -CH = NOR⁹², phenyl which is optionally substituted with 1, 2, 3, 4 or 5 R¹⁶ substituents; and a heterocyclic ring selected from the rings of formulas E-1 to E-63 as defined above; R⁸¹ is independently selected from OH, CN, C₃₋₈-cycloalkyl which optionally has a CN or C₁-haloalkyl, C₃₋₆-halocycloalkyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₁₋₆-alkylthio, C₁ substituent ₋₆-haloalkylthio, C₁₋₆-alkylsulfinyl, C₁₋₆-haloalkylsulfinyl, C₁₋₆-alkylsulfonyl, C₁₋₆-haloalkylsulfonyl, -C (= O) N (R¹⁰¹ᶜ) R¹⁰¹ᵈ, phenyl, optionally substituted with 1, 2, 3, 4 or 5 R¹⁶ substituents and a heterocyclic ring selected from rings E-1 to E-63 as defined above; each R⁸² is independently selected from OH, CN, C₃₋₆-cycloalkyl which optionally has a CN or C₁-haloalkyl, C₃₋₆-halocycloalkyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₁₋₆-alkylthio substituent, C₁₋₆-haloalkylthio, C₁₋₆-alkylsulfinyl, C₁₋₆-haloalkylsulfinyl, C₁₋₆-alkylsulfonyl, C₁₋₆-haloalkylsulfonyl, -C (= O) N (R¹⁰²ᶜ) R¹⁰²ᵈ, phenyl, optionally substituted with 1, 2 , 3, 4 or 5 R¹⁶ substituents and a heterocyclic ring selected from rings E-1 to E-63 as defined above; R⁹¹ and R⁹² are independently selected from hydrogen, C₁₋₆-alkyl and C₁₋₆-haloalkyl; R¹⁰¹ᵃ, R¹⁰²ᵃ, R¹⁰²ᶜ and R¹¹²ᵃ are independently selected from hydrogen and C₁₋₆-alkyl; R¹⁰¹ᵇ is selected from hydrogen, -C (= O) N (R¹⁴ᵃ) R¹⁴ᵇ, phenyl, optionally substituted with 1, 2, 3, 4 or 5 R¹⁶ substituents; and a heterocyclic ring selected from the rings of formulas E-1 to E-42 as defined above; R¹⁰²ᵇ is selected from hydrogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, CH₂-CN, C₂₋₄-alkenyl, C₂₋₄-alkynyl, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆- cycloalkylmethyl, C₃₋₆-halocycloalkylmethyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5 R¹⁶ substituents; and a heterocyclic ring selected from the rings of formulas E-1 to E-42 as defined above; R¹⁰¹ᶜ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₃-alkynyl and CH₂-CN; R¹⁰¹ᵈ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₄-alkenyl, C₂₋₄-alkynyl, CH₂-CN, C₁₋₆-haloalkyl, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkylmethyl, C₃₋₆-halocycloalkylmethyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, phenyl which is optionally substituted with 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, cyano, nitro, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₂₋₄-alkenyl, C₂₋₄-haloalkenyl, C₂₋₄-alkynyl, C₂₋₄-haloalkynyl, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₁₋₄-alkoxy, C₁₋₄-haloalkoxy, C₁₋₄-alkylthio and C₁₋₄-haloalkylthio; and a heterocyclic ring selected from the rings of formulas E-1 to E-63 as defined above; R¹⁰²ᵈ and R¹¹²ᵇ are independently selected from hydrogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₂₋₆-alkenyl, C₂₋₆-haloalkenyl, C₂₋₆-alkynyl, C₂₋₆-haloalkynyl, C₃ ₋₆ -cycloalkyl having optionally a CN, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkylmethyl and C₃₋₆-halocycloalkylmethyl substituent; R¹⁴ᵃ is selected from the group consisting of hydrogen and C₁₋₆-alkyl; R¹⁴ᵇ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₂₋₄-alkenyl, C₂₋₄-alkynyl, CH₂-CN, C₁₋₆-haloalkyl, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkylmethyl, C₁₋₄-alkoxy and C₁₋₄-haloalkoxy; each R¹⁶ is independently selected from the group consisting of halogen, cyano, nitro, C₁₋₄-alkyl, C₁₋₄-haloalkyl, C₂₋₄-alkenyl, C₂₋₄-haloalkenyl, C₂₋₄-alkynyl, C₂₋₄- haloalkynyl, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkyl-C₁₋₄-alkyl, C₃₋₆-halocycloalkyl C₁₋₄-alkyl, 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, C₁₋₄-haloalkylcarbonyl, aminocarbonyl, C₁ ₋₄-alkylaminocarbonyl and di- (C₁₋₄-alkyl) aminocarbonyl; or two R¹⁶ present in the same carbon atom of a saturated ring can form together = O or = S; or two R¹⁶ present in the same member of the S or SO ring of a heterocyclic ring can together form a group = N (C₁₋₆-alkyl), = NO (C₁₋₆-alkyl), = NN (H) (C₁₋ ₆-alkyl) o = NN (C₁₋₆-alkyl) ₂; and the N-oxides, stereoisomers and salts thereof acceptable in agriculture or veterinary.
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