| US 7,601,743 B2 | ||
| Cyano anthranilamide insecticides | ||
| Andre Jeanguenat, Basel (Switzerland); Anthony O'Sullivan, Basel (Switzerland); Michael Muehlebach, Basel (Switzerland); Stephan Trah, Basel (Switzerland); and Roger Graham Hall, Basel (Switzerland) | ||
| Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US) | ||
| Appl. No. 11/911,887 PCT Filed Apr. 18, 2006, PCT No. PCT/EP2006/003504 § 371(c)(1), (2), (4) Date Oct. 18, 2007, PCT Pub. No. WO2006/111341, PCT Pub. Date Oct. 26, 2006. |
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| Claims priority of application No. 0507989.2 (GB), filed on Apr. 20, 2005; and application No. 0525060.0 (GB), filed on Dec. 08, 2005. | ||
| Prior Publication US 2008/0182750 A1, Jul. 31, 2008 | ||
| Int. Cl. C07D 401/04 (2006.01); A61K 31/4439 (2006.01) | ||
| U.S. Cl. 514—341 [544/92; 546/275.4; 548/374.1] | 10 Claims |
1. A compound of formula I
 each of E and Z, which may be the same or different, represents oxygen or sulfur;
A is C1-C6alkylene, C2-C6alkenylene, C2-C6alkynylene, or a bivalent three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated
or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur,
it not being possible for each ring system to contain more than 2 oxygen atoms or more than 2 sulfur atoms;
and it being possible for the three- to ten-membered ring system itself and also for the C1-C6alkylene, C2-C6alkenylene and C2-C6alkynylene groups to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated
or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur,
it not being possible for each ring system to contain more than 2 oxygen atoms or more than 2 sulfur atoms, and it being possible
for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy, C3-C6trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C2-C4alkylcarbonyl-C1-C3alkylthio, C2-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsutflnyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylamino-sulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano or nitro; and
substituents at nitrogen atoms in the ring systems being other than halogen;
X is oxygen, NH or C1-C4alkyl-N;
Y is a three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated or fully saturated
and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible
for each ring system to contain more than 2 oxygen atoms or more than 2 sulfur atoms;
and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano,
nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated
or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur,
it not being possible for each ring system to contain more than 2 oxygen atoms or more than 2 sulfur atoms, and it being possible
for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy, C3-C6trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C2-C4alkylcarbonyl-C1-C3alkylthio, C2-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylamino- sulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano or nitro; and
substituents at nitrogen atoms in the ring systems being other than halogen;
p is 0 or 1;
q is 0 or 1;
B is a three- to four-membered ring system which is fully or partially saturated and can contain a hetero atom selected from
the group consisting of nitrogen, oxygen and sulfur, and it being possible for the three- to four-membered ring system itself
to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulflnyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy, C3-C6trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated
or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur,
it not being possible for each ring system to contain more than 2 oxygen atoms or more than 2 sulfur atoms, and it being possible
for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C5-C7cycloalkenyl, C5-C8cycloalkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C5-C7halocycloalkenyl, C5-C8halocycloalkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy, C3-C6trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C1-C6alkyl, C1-C6haloalkyl,C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C1-C3alkoxy-C1-C3alkylthio, C2-C4alkylcarbonyl-C1-C3alkylthio, C2-C4alkoxycarbonyl-C1-C3alkylthio, cyano-C1-C3alkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylamino-sulfonyl, N,N-di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano or nitro; and
substituents at nitrogen atoms in the ring systems being other than halogen;
each R1 independently is halogen, nitro, cyano, hydroxy, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro,
halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino, C1-C6alkyl-C3-C6cycloalkylamino, C2-C4alkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6alkylaminocarbonyl, C3-C6dialkylaminocarbonyl, C2-C6alkoxycarbonyloxy, C2-C6alkylaminocarbonyloxy, C3-C6dialkylaminocarbonyloxy or C3-C6trialkylsilyl;
n is 0, 1, 2 or 3;
each of R2 and R3, which may be the same or different, represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C8cycloalkyl; or C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C8cycloalkyl substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino, C3-C6cycloalkylamino and C1-C6alkyl-C3-C6cycloalkylamino;
D is phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl; or phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted
by C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, halogen, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl;
or D is a group
 R5, R6, R8, R11, R12, R15, R16 and R18 independently from each other, are C1-C6alkyl, or C1-C6alkyl mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C1-C4alkoxy, C2-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkylamino, C2-C4dialkylamino or C3-C6cycloalkylamino; or are phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl; or are or phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-,
di- or trisubstituted by C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, halogen, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl;
R7, R9, R13 and R14 independently from each other, are hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkenyl or C3-C6haloalkenyl or agronomically acceptable salts/stereoisomers/enantiomers/tautomers/N-oxides of those compounds.
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