Insecticidal Benzenedicarboxamide Derivative
First Claim
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1. A benzenedicarboxamide derivative represented by the following formula:
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Abstract
The present invention relates to a novel benzenedicarboxamide derivative and the use thereof as an insecticide having the formula (I) wherein the chemical groups W1 to W9, and R1 to R3 are as defined here-in.
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4 Claims
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1. A benzenedicarboxamide derivative represented by the following formula:
- View Dependent Claims (2, 3, 4)
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2. The compound of claim 1, wherein R1 represents a hydrogen atom, or C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, C1-8 alkoxy, C2-8 (total number of carbon atoms) dialkylamino, carboxy-C1-6 alkyl, formyl-C1-6 alkyl, hydroxyimino-C1-6 alkyl, hydroxy-C1-6 alkyl, C2-8 (total number of carbon atoms) alkoxyalkyl, aminosulfonyl-C1-6 alkyl, C2-10 (total number of carbon atoms) alkylaminosulfonylalkyl, C2-10 (total number of carbon atoms) alkylthioalkyl, C2-10 (total number of carbon atoms) alkylsulfinylalkyl, C2-10 (total number of carbon atoms) alkylsulfonylalkyl, C4-12 (total number of carbon atoms) cycloalkylthioalkyl, C4-12 (total number of carbon atoms) cycloalkylsulfinylalkyl, C4-12 (total number of carbon atoms) cycloalkylsulfonylalkyl, C4-10 (total number of carbon atoms) trialkylsilylalkyl, C2-10 (total number of carbon atoms) alkoxycarbonylmethylaminocarbonylalkyl, C2-10 (total number of carbon atoms) alkylcarbamoyloxyalkyl, C2-10 (total number of carbon atoms) monoalkylcarbamoylalkyl, C3-10 (total number of carbon atoms) monoalkenylcarbamoylalkyl, C4-10 (total number of carbon atoms) cycloalkylcarbamoylalkyl, C2-10 (total number of carbon atoms) alkoxycarbonylaminoalkyl, C2-10 (total number of carbon atoms) dialkylaminosulfonylalkyl, benzyloxycarbonyl-C1-6 alkyl, benzyloxy-C1-6 alkyl, C1-4 alkylthioaryl, C1-4 alkylsulfinylaryl, C1-4 alkylsulfonylaryl, C1-4 alkylthioheteroaryl, C1-4 alkylsulfinylheteroaryl, C1-4 alkylsulfonylheteroaryl, C3-10 (total number of carbon atoms) cycloalkylalkyl which may be substituted, or 5- or 6-membered heterocyclyl or 5- or 6-membered heterocyclyl-C1-6 alkyl which may be substituted,
R1 and R2 together with a nitrogen atom to which they are attached may form a saturated 5- or 6-membered heterocyclic group constituted by a combination of a carbon atom, an oxygen atom and a sulfur atom, R2 and R3 represent a hydrogen atom, or C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-8 (total number of carbon atoms) alkoxyalkyl or C2-8 (total number of carbon atoms) alkylthioalkyl which may be substituted, W1 represents a nitrogen atom or C— - X1,
W2 represents a nitrogen atom or C—
X2,W3 represents a nitrogen atom or C—
X3,W4 represents a nitrogen atom or C—
X4, X1, X2, X3 and X4, which may be identical or different, represent a hydrogen atom, nitro, formyl, amino, cyano, halogen, carbamoyl, or C1-6 alkyl, C1-6 haloalkyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 acylamino, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylthio, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, C3-8 cycloalkylthio, C3-8 cycloalkylsulfinyl, C3-8 cycloalkylsulfonyl, C4-10 (total number of carbon atoms) cycloalkylalkylthio, C4-10 (total number of carbon atoms) cycloalkylalkylsulfinyl, C4-10 (total number of carbon atoms) cycloalkylalkylalkylsulfonyl, C1-6 alkylsulfonyloxy, C1-6 haloalkylsulfonyloxy, C1-6 monoalkylaminosulfonyl, C2-8 (total number of carbon atoms) dialkylaminosulfonyl, C1-6 monoalkylamino, C2-8 (total number of carbon atoms) dialkylamino, C1-6 monoalkylcarbamoyl, C2-8 (total number of carbon atoms) dialkylcarbamoyl, C2-6 alkenyl, C2-6 alkenyloxy, C2-6 alkynyl, C2-6 alkynyloxy, C3-8 cycloalkyl, C3-8 cycloalkyloxy which may be substituted, or aryl, aryloxy, arylthio, aryl C1-4 alkyl, aryl C1-4 alkoxy which may be substituted, aryl C1-4 alkylthio, heteroaryl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclyl C1-4 alkoxy which may be substituted by nitro, formyl, cyano, halogen, and C1-4 alkyl, C1-4 haloalkyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio or C1-4 haloalkylthio which may be substituted, adjacent W1 and W2, W2 and W3 or W3 and W4 may form a 5- or 6-membered carbon ring or a heterocyclic group constituted by a combination of oxygen, sulfur, nitrogen which may be substituted by C1-2 alkyl, and carbon which may be substituted by halogen,W5 represents a nitrogen atom, C—
Y1 or C-(A)r-Q,W6 represents a nitrogen atom, C—
Y2 or C-(A)r-Q,W7 represents a nitrogen atom, C—
Y3 or C-(A)r-Q,W8 represents a nitrogen atom, C—
Y4 or C-(A)r-Q,W9 represents a nitrogen atom, C—
Y5 or C-(A)r-Q,among these, at least one of W5 to W9 necessarily represents C-(A)r-Q, Y1, Y3, Y4 and Y5, which may be identical or different, represent a hydrogen atom, nitro, formyl, carbamoyl, amino, cyano, halogen, or C1-6 alkyl, C1-6 haloalkyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 acylamino, C1-6 alkoxy, C1-6 haloalkoxy, C2-8 (total number of carbon atoms) alkoxycarbonylalkyl, C1-6 alkylthio, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylthio, C2-8 (total number of carbon atoms) alkylthioalkyl, C1-6 monoalkylamino, C2-8 (total number of carbon atoms) dialkylamino, C1-6 monoalkylcarbamoyl, C2-8 (total number of carbon atoms) dialkylcarbamoyl, C2-6 alkenyl, C2-6 alkenyloxy, C2-6 alkynyl, C2-6 alkynyloxy, C3-8 cycloalkyl, C3-8 cycloalkyloxy, C4-9 (total number of carbon atoms) cycloalkylalkyl, C4-9 (total number of carbon atoms) cycloalkylalkoxy which may be substituted, or aryl, aryloxy, arylthio, aryl C1-4 alkyl, aryl C1-4 alkoxy, aryl C1-4 alkylthio, heteroaryl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclyl C1-4 alkoxy which may be substituted by at least one selected from the group consisting of formyl, cyano, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkylcarbonyl, C1-4 alkoxycarbonyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio and C1-4 haloalkylthio, A represents O, S, SO, SO2, NH, N(CH3), CH(CH3), CH(C2H5), C(═
O), C(═
N—
OCH3), CH(OH), CH(CN), CH(CF3), C(CF3)2, CH(CO2CH3) or CH(CO2C2H5), or C1-4 alkylene which may be interrupted by O, S, SO, SO2, NH, N(CH3), CH(CH3), CH(C2H5), C(═
O), C(═
N—
OCH3), CH(OH), CH(CN), CH(CF3), C(CF3)2, CH(CO2CH3) or CH(CO2C2H5),r represents 0, 1, 2, 3 or 4, and Q represents a 5- or 6-membered heterocyclic group which has at least one heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom and is selected from the following Q1 to Q67;
- X1,
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3. The compound of claim 1, wherein R1 represents a hydrogen atom, or C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C1-6 alkoxy, C2-6 (total number of carbon atoms) dialkylamino, carboxy-C1-4 alkyl, formyl-C1-4 alkyl, hydroxyimino-C1-4 alkyl, hydroxy-C1-4 alkyl, C2-6 (total number of carbon atoms) alkoxyalkyl, aminosulfonyl-C1-4 alkyl, C2-8 (total number of carbon atoms) alkylaminosulfonylalkyl, C2-8 (total number of carbon atoms) alkylthioalkyl, C2-8 (total number of carbon atoms) alkylsulfinylalkyl, C2-8 (total number of carbon atoms) alkylsulfonylalkyl, C4-10 (total number of carbon atoms) cycloalkylthioalkyl, C4-10 (total number of carbon atoms) cycloalkylsulfinylalkyl, C4-10 (total number of carbon atoms) cycloalkylsulfonylalkyl, C4-8 (total number of carbon atoms) trialkylsilylalkyl, C2-8 (total number of carbon atoms) alkoxycarbonylmethylaminocarbonylalkyl, C2-8 (total number of carbon atoms) alkylcarbamoyloxyalkyl, C2-8 (total number of carbon atoms) monoalkylcarbamoylalkyl, C3-8 (total number of carbon atoms) monoalkenylcarbamoylalkyl, C4-8 (total number of carbon atoms) cycloalkylcarbamoylalkyl, C2-8 (total number of carbon atoms) alkoxycarbonylaminoalkyl, C2-8 (total number of carbon atoms) dialkylaminosulfonylalkyl, benzyloxycarbonyl-C1-4 alkyl, benzyloxy-C1-4 alkyl, C1-2 alkylthioaryl, C1-2 alkylsulfinylaryl, C1-2 alkylsulfonylaryl, C1-2 alkylthioheteroaryl, C1-2 alkylsulfinylheteroaryl, C1-2 alkylsulfonylheteroaryl, C3-8 (total number of carbon atoms) cycloalkylalkyl, 5- or 6-membered heterocyclyl or 5- or 6-membered heterocyclyl-C1-4 alkyl which may be substituted, R1 and R2 together with a nitrogen atom to which they are attached may form a 5- or 6-membered heterocyclic group:
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4. An insecticide comprising as an active ingredient a compound of claim 1
wherein R1 represents a hydrogen atom, or alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, dialkylamino, carboxyalkyl, formylalkyl, hydroxyiminoalkyl, hydroxyalkyl, alkoxyalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cycloalkylthioalkyl, cycloalkylsulfinylalkyl, cycloalkylsulfonylalkyl, trialkylsilylalkyl, alkoxycarbonylmethylaminocarbonylalkyl, alkylcarbamoyloxyalkyl, monoalkylcarbamoylalkyl, monoalkenylcarbamoylalkyl, monoalkynylcarbamoylalkyl, cycloalkylcarbamoylalkyl, alkoxycarbonylaminoalkyl, dialkylaminosulfonylalkyl, benzyloxycarbonylalkyl, benzyloxyalkyl, alkylthioaryl, alkylsulfinylaryl, alkylsulfonylaryl, alkylthioheteroaryl, alkylsulfinylheteroaryl, alkylsulfonylheteroaryl, cycloalkylalkyl, heterocyclyl or heterocyclylalkyl which may be substituted, R2 and R3 each independently represent a hydrogen atom, or alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl which may be substituted, R1 and R2 together with a nitrogen atom to which they are attached may form a 5- or 6-membered heterocyclic group, W1 represents a nitrogen atom or C— - X1,
W2 represents a nitrogen atom or C—
X2,W3 represents a nitrogen atom or C—
X3,W4 represents a nitrogen atom or C—
X4,X1, X2, X3 and X4, which may be identical or different, represent a hydrogen atom, nitro, formyl, amino, cyano, halogen, carbamoyl, or alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, acylamino, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, cycloalkylalkylthio, cycloalkylalkylsulfinyl, cycloalkylalkylsulfonyl, alkylsulfonyloxy, haloalkylsulfonyloxy, monoalkylaminosulfonyl, dialkylaminosulfonyl, monoalkylamino, dialkylamino, monoalkylcarbamoyl, dialkylcarbamoyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, cycloalkyl, cycloalkyloxy, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, heteroaryl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylalkoxy which may be substituted, adjacent W1 and W2, W2 and W3 or W3 and W4 may together form a 5- or 6-membered carbon ring or a heterocyclic group, W5 represents a nitrogen atom, C—
Y1 or C-(A)r-Q,W6 represents a nitrogen atom, C—
Y2 or C-(A)r-Q,W7 represents a nitrogen atom, C—
Y3 or C-(A)r-Q,W8 represents a nitrogen atom, C—
Y4 or C-(A)r-Q,W9 represents a nitrogen atom, C—
Y5 or C-(A)r-Q,at least one of W5 to W9 necessarily represents C-(A)r-Q, Y1, Y2, Y3, Y4 and Y5, which may be identical or different, represent a hydrogen atom, nitro, formyl, carbamoyl, amino, cyano, halogen, or alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, acylamino, alkoxy, haloalkoxy, alkoxycarbonylalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, alkylthioalkyl, monoalkylamino, dialkylamino, monoalkylcarbamoyl, dialkylcarbamoyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, aryl, aryloxy, arylthio, arylalkyl, arylalkoxy, arylalkylthio, heteroaryl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylalkoxy which may be substituted, A represents O, S, SO, SO2, NH, N(CH3), CH(CN), C(═
N—
OCH3), C(═
O), CH(OH), CH(CH3), CH(CF3), C(CF3)2, CH(CO2CH3) or CH(CO2C2H5), or alkylene which may be interrupted by O, S, SO, SO2, NH, N(CH3), CH(CN), C(═
N—
OCH3), C(═
O), CH(OH), CH(CH3), CH(CF3), C(CF3)2, CH(CO2CH3) or CH(CO2C2H5),r represents 0, 1, 2, 3, 4 or 5, and Q represents a 5- or 6-membered heterocyclic group which may be substituted.
- X1,
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2. The compound of claim 1, wherein R1 represents a hydrogen atom, or C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, C1-8 alkoxy, C2-8 (total number of carbon atoms) dialkylamino, carboxy-C1-6 alkyl, formyl-C1-6 alkyl, hydroxyimino-C1-6 alkyl, hydroxy-C1-6 alkyl, C2-8 (total number of carbon atoms) alkoxyalkyl, aminosulfonyl-C1-6 alkyl, C2-10 (total number of carbon atoms) alkylaminosulfonylalkyl, C2-10 (total number of carbon atoms) alkylthioalkyl, C2-10 (total number of carbon atoms) alkylsulfinylalkyl, C2-10 (total number of carbon atoms) alkylsulfonylalkyl, C4-12 (total number of carbon atoms) cycloalkylthioalkyl, C4-12 (total number of carbon atoms) cycloalkylsulfinylalkyl, C4-12 (total number of carbon atoms) cycloalkylsulfonylalkyl, C4-10 (total number of carbon atoms) trialkylsilylalkyl, C2-10 (total number of carbon atoms) alkoxycarbonylmethylaminocarbonylalkyl, C2-10 (total number of carbon atoms) alkylcarbamoyloxyalkyl, C2-10 (total number of carbon atoms) monoalkylcarbamoylalkyl, C3-10 (total number of carbon atoms) monoalkenylcarbamoylalkyl, C4-10 (total number of carbon atoms) cycloalkylcarbamoylalkyl, C2-10 (total number of carbon atoms) alkoxycarbonylaminoalkyl, C2-10 (total number of carbon atoms) dialkylaminosulfonylalkyl, benzyloxycarbonyl-C1-6 alkyl, benzyloxy-C1-6 alkyl, C1-4 alkylthioaryl, C1-4 alkylsulfinylaryl, C1-4 alkylsulfonylaryl, C1-4 alkylthioheteroaryl, C1-4 alkylsulfinylheteroaryl, C1-4 alkylsulfonylheteroaryl, C3-10 (total number of carbon atoms) cycloalkylalkyl which may be substituted, or 5- or 6-membered heterocyclyl or 5- or 6-membered heterocyclyl-C1-6 alkyl which may be substituted,
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Current AssigneeBayer Cropscience AG (Bayer AG)
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Original AssigneeBayer Cropscience AG (Bayer AG)
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InventorsFunke, Christian, Paulitz, Christian, Sato, Yoshitaka, Kapferer, Tobias, Fisher, Rüdiger, Kishikawa, Hidetoshi, Gomibuchi, Takuya, Kudo, Sachio, Yoneta, Yasushi, Franken, Eva-Maria, Sanwald, Erich, Malsam, Olga, Görgens, Ulrich, Shibuya, Katsuhiko, Reckmann, Udo, Shimojo, Eiichi, Wada, Katsuaki, Arnold, Christian, Murata, Tetsuya, Ataka, Masashi, Emoto, Akira
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Application NumberUS13/056,518Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current548/262.2CPC Class CodesA01N 43/36 five-membered ringsA01N 43/50 1,3-Diazoles; Hydrogenated ...A01N 43/54 1,3-Diazines; Hydrogenated ...A01N 43/56 1,2-Diazoles; Hydrogenated ...A01N 43/653 1,2,4-Triazoles; Hydrogenat...A01N 43/707 1,2,3- or 1,2,4-triazines; ...A01N 43/713 having rings with four or m...A01N 43/78 1,3-Thiazoles; Hydrogenated...A01N 43/80 five-membered rings with on...A01N 43/82 five-membered rings with th...C07D 231/12 with only hydrogen atoms, h...C07D 233/64 with substituted hydrocarbo...C07D 239/26 with only hydrogen atoms, h...C07D 239/34 One oxygen atomC07D 249/02 not condensed with other ringsC07D 249/08 1,2,4-Triazoles; Hydrogenat...C07D 249/12 Oxygen or sulfur atomsC07D 253/07 with hetero atoms, or with ...C07D 257/04 Five-membered ringsC07D 261/08 with only hydrogen atoms, h...C07D 271/06 : 1,2,4-Oxadiazoles; Hydrogen...C07D 271/10 : 1,3,4-Oxadiazoles; Hydrogen...C07D 401/04 : directly linked by a ring-m...C07D 401/06 : linked by a carbon chain co...C07D 401/12 : linked by a chain containin...C07D 403/04 : directly linked by a ring-m...C07D 403/06 : linked by a carbon chain co...C07D 403/12 : linked by a chain containin...C07D 405/04 : directly linked by a ring-m...C07D 405/12 : linked by a chain containin...C07D 409/04 : directly linked by a ring-m...C07D 409/12 : linked by a chain containin...C07D 417/12 : linked by a chain containin...