http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-111756-A1

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filingDate 2018-05-04-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_dbd0444ccfc7b678b2257126d665f54b
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_443167a85912f50a48d2b27b782bc1ac
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publicationDate 2019-08-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-111756-A1
titleOfInvention 4-DIFLUOROMETILBENZOILAMIDES OF HERBICIDE ACTION
abstract Benzoylamides are described as herbicides. Claim 1: Benzoylamides of the formula (1) and their Salze salts, where the symbols and indices have the following meanings: Q means a radical (Q1), (Q2), (Q3) or (Q4) selected from the group of formulas (two); X means C₁₋₆ alkyl, C₃₋₆ cycloalkyl or halogen; R denotes C₁₋₆ alkyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl, C₁₋₆ alkyl-O-C₁₋₆ alkyl; Rᵃ stands for hydrogen, C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₂₋₆ alkenyl, halogen-C₂₋₆ alkenyl, C₂₋₆ alkynyl, halogen-C₃₋₆ alkynyl, C₃₋₆ cycloalkyl, halogen-C₃₋ cycloalkyl ₆, C₃₋₆-cycloalkyl-C₁₋₆-alkyl, halogen-C₃₋₆-cycloalkyl-C₁₋₆-alkyl, R¹(O)C-C₁₋₆-alkyl, R¹O(O)C-C₁₋₆-alkyl, (R¹)₂N (O)C-C₁₋₆-alkyl, NC-C₁₋₆-alkyl, R¹O-C₁₋₆-alkyl, R¹(O)CO-C₁₋₆-alkyl, R²(O)₂SO-C₁₋₆-alkyl, (R¹)₂N -C₁₋₆-alkyl, R¹(O)C(R¹)N-C₁₋₆-alkyl, R²(O)₂S(R¹)N-C₁₋₆-alkyl, R²(O)ₙS-C₁₋₆-alkyl, R¹O(O )₂S-C₁₋₆-alkyl, (R¹)₂N(O)₂S-C₁₋₆-alkyl, R¹(O)C, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)₂S, or in each case benzyl substituted with radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen; RX means C₁₋₆ alkyl, halogeno-C₁₋₆ alkyl, C₂₋₆ alkenyl, halogeno-C₂₋₆ alkenyl, C₂₋₆ alkynyl, halogeno-C₃₋₆ alkynyl, wherein the last six aforementioned radicals are substituted on each case with s radicals of the group consisting of nitro, cyano, (R⁶)₃Si, (R⁵O)₂(O)P, R²(O)ₙS, (R¹)₂N, R¹O, R¹(O)C, R¹O(O)C , R¹(O)CO, R²O(O)CO, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, C₃₋₆ cycloalkyl, heteroaryl, heterocyclyl, and phenyl, where the last four radicals mentioned are substituted with s radicals from the group consisting of C₁₋₆ alkyl, halogen-C₁₋₆ alkyl, C₁₋₆ alkoxy, halogen-C₁₋₆ alkoxy and halogen and wherein heterocyclyl bears n oxo groups, or RX is C₃ cycloalkyl ₋₇, heteroaryl, heterocyclyl or phenyl, wherein the four aforementioned radicals are substituted in each case with s radicals from the group consisting of halogen, nitro, cyano, C₁₋₆-alkyl, halogen-C₁₋₆-alkyl, C₃₋₆-cycloalkyl , C₁₋₆ alkyl-S(O)ₙ, C₁₋₆ alkoxy, halogen-C₁₋₆ alkoxy and C₁₋₆ alkoxy-C₁₋₄ alkyl; RY means hydrogen, C₁₋₆ alkyl, C₁₋₆ halogeno-alkyl, C₂₋₆ alkenyl, C₂₋₆ halogeno-alkenyl, C₂₋₆ alkynyl, C₃₋₆ halogeno-alkynyl, C₃₋₇ cycloalkyl, C₁₋₆ alkoxy, halogen-C₁₋₆-alkoxy, C₂₋₆-alkenyl-oxy, C₂₋₆-alkynyl-oxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl, , halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl or heteroaryl, heterocyclyl or phenyl substituted in each case with s radicals from the group consisting of C₁₋₆-alkyl, halogeno-C₁₋₆-alkyl, C₁₋₆-alkoxy, halogen-C₁-alkoxy ₋₆ and halogen and wherein the heterocyclyl bears n oxo groups; RZ means hydrogen, C₁₋₆ alkyl, R¹O-C₁₋₆ alkyl, R'CH₂, C₃₋₇ cycloalkyl, halogen-C₁₋₆ alkyl, C₂₋₆ alkenyl, halogeno-C₂₋₆ alkenyl, C₂₋₆ alkynyl, halogen -C₃₋₆-alkynyl, R¹O, R¹(H)N, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl, dimethylamino, trifluoromethylcarbonyl, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl or heteroaryl, heterocyclyl, benzyl or phenyl substituted in each case with s radicals from the group consisting of halogen, nitro, cyano, C₁₋₆-alkyl, halogen-C₁₋₆-alkyl, C₃₋₆-cycloalkyl, C₁₋₆-alkyl-S(O)ₙ, C₁₋₆-alkoxy, halogen-C₁₋₆-alkoxy, and C₁₋₆-alkoxy -C₁₋₄ alkyl, wherein the heterocyclyl bears n oxo groups; R¹ stands for hydrogen, C₁₋₆-alkyl, halogen-C₁₋₆-alkyl, C₂₋₆-alkenyl, halogen-C₂₋₆-alkenyl, C₂₋₆-alkynyl, halogeno-C₃₋₆-alkynyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, Halogen-C₃₋₆-cycloalkyl, C₃₋₆-cycloalkyl-C₁₋₆-alkyl, C₁₋₆-alkyl-O-C₁₋₆-alkyl, cycloalkyl-C₁₋₆-alkyl-O-C₁₋₆-alkyl, phenyl, phenyl-C₁₋-alkyl ₆, Heteroaryl, Heteroaryl-C₁₋₆-Alkyl, Heterocyclyl, Heterocyclyl-C₁₋₆-Alkyl, Phenyl-O-C₁₋₆-Alkyl, Heteroaryl-O-C₁₋₆-Alkyl, Heterocyclyl-O-C₁₋₆-Alkyl, Phenyl-N (R³)-C₁₋₆-alkyl, heteroaryl-N(R³)-C₁₋₆-alkyl, heterocyclyl-N(R³)-C₁₋₆-alkyl, phenyl-S(O)ₙ-C₁₋₆-alkyl, heteroaryl-S( O)ₙ-C₁₋₆-alkyl, heterocyclyl-S(O)ₙ-C₁₋₆-alkyl, wherein the last fifteen mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, rhodan, alkyl C₁₋₆, halogen-C₁₋₆ alkyl, C₃₋₆ cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)ₙS, R³O(O)₂S, (R³)₂N(O)₂S and R³O-C₁₋₆ alkyl and wherein the heterocyclyl lle va n oxo groups; R² stands for C₁₋₆-alkyl, C₁₋₆-halogen-alkyl, C₂₋₆-alkenyl, C₂₋₆-halogen-alkenyl, C₂₋₆-alkynyl, C₃₋₆-halogen-alkynyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, halogen C₃₋₆-cycloalkyl, C₃₋₆-cycloalkyl-C₁₋₆-alkyl, C₁₋₆-alkyl-O-C₁₋₆-alkyl, cycloalkyl-C₁₋₆-alkyl-O-C₁₋₆-alkyl, phenyl, phenyl-C₁₋₆-alkyl, heteroaryl, heteroaryl-C₁₋₆-alkyl, heterocyclyl, heterocyclyl-C₁₋₆-alkyl, phenyl-O-C₁₋₆-alkyl, heteroaryl-O-C₁₋₆-alkyl, heterocyclyl-O-C₁₋₆-alkyl, phenyl-N(R³ )-C₁₋₆-alkyl, heteroaryl-N(R³)-C₁₋₆-alkyl, heterocyclyl-N(R³)-C₁₋₆-alkyl, phenyl-S(O)ₙ-C₁₋₆-alkyl, heteroaryl-S(O) ₙ-C₁₋₆-alkyl, heterocyclyl-S(O)ₙ-C₁₋₆-alkyl, wherein the last fifteen mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, rhodan, C₁₋-alkyl ₆, halogen-C₁₋₆ alkyl, C₃₋₆ cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)ₙS, R³O(O)₂S, (R³ )₂N(O)₂S and R³O-C₁₋₆ alkyl and wherein the heterocyclyl bears n groups oxo; R³ means hydrogen, C₁₋₆ alkyl, halogeno-C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl or phenyl; R⁴ denotes C₁₋₆ alkyl, halogeno-C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkyl-C₁₋₆ alkyl or phenyl; R⁵ means hydrogen or C₁₋₄ alkyl; R⁶ means C₁₋₄ alkyl; R' means acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, C₃₋₆ cycloalkyl or heteroaryl or heterocyclyl substituted in each case with s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen; n means 0, 1 or 2; s means 0, 1, 2 or 3; provided that the compounds 4-difluoromethyl-3-ethylsulfinyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and 4-difluoromethyl-3-ethylsulfonyl- 2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide; as well as its sodium salts.
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