US2018070591A1PendingUtilityA1
Compositions and methods for controlling nematodes
Est. expiryFeb 10, 2029(~2.6 yrs left)· nominal 20-yr term from priority
A61P 33/10C07D 413/04C07D 413/06A01N 43/76A01N 43/82C07D 417/06C07D 417/04A01N 43/653
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Claims
Abstract
Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of Formula XIX or a salt thereof,
wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
B is C(H) or C(CH 3 ); and
C is heteroaryl, heteroarylalkyl, hetroaryloxo, or heteroarylthio, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocyclyl, hydroxyalkyl, halogen, and OCF 3 .
2 . The compound of claim 1 of Formula XIXa or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocyclyl, and halogen;
B is C(H) or C(CH 3 ); and
X is a bond, CH 2 , O or S.
3 . The compound of claim 1 of Formula XIXb or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O or S;
B is C(H) or C(CH 3 ); and
X is a bond, CH 2 , O or S.
4 . The compound of claim 1 of Formula XIXc or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
B is C(H) or C(CH 3 );
E is O or S; and
X is a bond, CH 2 , O or S.
5 . The compound of claim 1 of Formula XIXd or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O or S;
B is C(H) or C(CH 3 ); and
X is a bond, CH 2 , O or S.
6 . The compound of claim 1 of Formula XIXe or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
B is C(H) or C(CH 3 );
E is O or S; and
X is a bond CH 2 , O or S.
7 . A compound of claim 1 selected from the group consisting of:
4-(2,4-dichlorophenyl)-2-(furan-2-yl)oxazole;
4-(2,4-dimethylphenyl)-2-(furan-2-yl)oxazole; and
4-(4-chlorophenyl)-2-(furan-2-yl)oxazole.
8 . A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of claim 1 .
9 . The method of claim 8 wherein the composition comprises a surfactant.
10 . The method of claim 8 wherein the composition includes one or more of a fungicide, an herbicide, and a pesticide.
11 . The method of claim 10 wherein the composition comprises a pesticide selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.
12 . The method of claim 8 wherein the composition is applied to plants, seeds or soil.
13 . The method of claim 8 wherein the composition is applied to a seed.
14 . A nematicidal composition comprising a compound of claim 1 at a concentration sufficient to reduce the viability of a parasitic nematode.
15 . The nematicidal composition of claim 14 wherein the composition comprises a surfactant.
16 . The nematicidal composition of claim 14 wherein the composition comprises one or more of a fungicide, an herbicide, and a pesticide.
17 . The nematicidal composition of claim 14 wherein the composition comprises a co-solvent.
18 . A coated seed wherein the coating comprises a compound of claim 1 .
19 . A compound of Formula I, IV, VII, XIII, XVI, or a salt thereof,
wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
B is C(H) or C(CH 3 ); and
C is pyrrolyl, pyrrolyloxo, pyrrolythio, or pyrrolylalkyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocyclyl, hydroxyalkyl, and halogen.
20 . A compound of Formula II, III,V, VI, XI, XII, XIV, XV, XVII, XVIII, or a salt thereof,
wherein,
A is aryl, arylalkyl, heteroaryl, or heteroarylalkyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
B is C(H) or C(CH 3 );
C is a heteroaryl, which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH 3 , and OCF 3 ; and
X is O or S when the compound is of Formula II, Formula V, Formula XI, Formula XIV, or Formula XVII; or
X is CH 2 , O, or S when the compound is of Formula III, Formula VI, Formula XII, Formula XV, or Formula XVIII.
21 . A compound of Formula XX or a salt thereof,
wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
B is C(H) or C(CH 3 ); and
C is heteroaryl, heteroarylalkyl, hetroaryloxo, or heteroarylthio, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of alkyl, cycloalkyl, heterocyclyl, hydroxyalkyl, halogen, and OCF 3 .
22 . A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of claim 19 .
23 . A nematicidal composition comprising a compound of claim 19 at a concentration sufficient to reduce the viability of a parasitic nematode.
24 . A coated seed wherein the coating comprises a compound of claim 19 .
25 . A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of claim 20 .
26 . A nematicidal composition comprising a compound of claim 20 at a concentration sufficient to reduce the viability of a parasitic nematode.
27 . A coated seed wherein the coating comprises a compound of claim 20 .
28 . A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of claim 21 .
29 . A nematicidal composition comprising a compound of claim 21 at a concentration sufficient to reduce the viability of a parasitic nematode.
30 . A coated seed wherein the coating comprises a compound of claim 21 .Cited by (0)
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