US2009221424A1PendingUtilityA1
Pesticides
Est. expiryMar 3, 2028(~1.6 yrs left)· nominal 20-yr term from priority
Inventors:Nneka T. BreauxMichael R. LosoTimothy C. JohnsonJonathan M. BabcockBenjamin M. NugentTimothy P. MartinAnnette V. BrownRonald Ross, Jr.William C. LoMatthias S. Ober
C07D 213/75C07C 381/10C07C 2603/18A01N 43/40C07C 2601/14C07C 2601/02C07D 405/12A01N 47/44A01N 47/36A01N 47/34C07D 401/12C07D 413/12C07D 213/32
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Claims
Abstract
Compounds having the following generic formula are disclosed.
Claims
exact text as granted — not AI-modified1 . A compound having the following formula (I)
wherein:
(a) R1 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, heterocyclyl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl;
(b) R2 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, heterocyclyl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring;
(c) R3 is F, Cl, Br, I, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, H, heterocyclyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 aryl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C 1 -C 8 alkoxy) C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R3 and R4 may also form a 4, 5, or 6 membered ring;
(d) R4 is F, Cl, Br, I, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, H, heterocyclyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 aryl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C1-C 8 alkoxy) C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R3 and R4 may also form a 4, 5, or 6 membered ring;
(e) R5 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, H, heterocyclyl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 3 -C 8 cycloalkyl, C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring, and wherein R5 and R6 may also form a 3, 4, 5, or 6 membered ring;
(f) R6 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, H, heterocyclyl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 3 -C 8 cycloalkyl, C 1 -C 6 hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring, and wherein R5 and R6 may also form a 3, 4, 5, or 6 membered ring;
(g) n is 0 to 4;
(h) X is NR8, O, or S;
(i) J is N or CR7;
(j) R7 is H, F, Cl, Br, I, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, heterocyclyl, or C 0 -C 8 alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 1 -C 6 hydroxyalkyl, NR9R10 and heterocyclyl;
(k) R8 is H, OH, OC(═O)C 1 -C 6 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C 1 -C 8 alkoxy), C 1 -C 6 hydroxyalkyl, and heterocyclyl;
(l) R9 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n1=0-2), OSO 2 C 1 -C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 1 -C 6 hydroxyalkyl, and heterocyclyl, and wherein R9 and R10 may also form a 4, 5, or 6 membered ring; and
(m) R10 is C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenylthio, C 1 -C 8 alkoxy, C 1 -C 8 alkyl, C 1 -C 8 alkylthio, C 2 -C 8 alkynyl, C 2 -C 8 alkynyloxy, C 2 -C 8 alkynylthio, aryl, C 3 -C 8 cycloalkenyl, C 3 -C 8 cycloalkenyloxy, C 3 -C 8 cycloalkenylthio, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 haloalkylthio, S(═O) n1 C 1 -C 6 alkyl (where n1=0-2), S(═O) n1 C 1 -C 6 haloalkyl (where n=0-2), OSO 2 C1-C 6 haloalkyl, C(═O)OC 1 -C 6 alkyl, C(═O)C 1 -C 6 alkyl, C(═O)C 1 -C 6 haloalkyl, aryl, C 1 -C 6 hydroxyalkyl, and heterocyclyl, and wherein R9 and R10 may also form a 4, 5, or 6 membered ring.
2 . A compound that is a pesticidally acceptable acid addition salt of a compound according to claim 1 .
3 . A solvate comprising compound according to claim 1 .
4 . A process comprising applying a compound according to claim 1 to a locus to control pests.
5 . A process comprising applying a compound according to claim 1 to a locus to control pests of Phylum Nematoda or Phylum Arthropoda.
6 . A composition comprising a mixture of a compound according to claim 1 with at least one other pesticide.
7 . A composition comprising a mixture of a compound according to claim 1 with at least one herbicide, at least one fungicide, or at least one herbicide and fungicide.
8 . A composition comprising a compound according to claim 1 with at least one of the following items: acetyl choline esterase inhibitor; sodium channel modulator; chitin biosynthesis inhibitor; GABA-gated chloride channel antagonist; GABA and glutamate-gated chloride channel agonist; acetyl choline receptor agonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinic acetylcholine receptor; Midgut membrane disrupter; or oxidative phosphorylation disrupter.
9 . A process of applying a compound of claim 1 to a seed.
10 . A process of applying a compound of claim 1 to a seed that has been genetically transformed to express one or more specialized traits.
11 . A process of applying a compound of claim 1 to a genetically transformed plant that has been genetically transformed to express one or more specialized traits.
12 . A process of orally administering or applying a compound of claim 1 to an animal.
13 . A process comprising reacting
to yield a compound according to claim 1 , wherein R1, R2, R3, R4, R5, and R6 are as specified in claim 1 .
14 . A compound having the following formulaCited by (0)
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