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US 2016/0242416 A1Published application
Fungicidal isoxazoline carbinols
AssigneeE. I. Du Pont de Nemours and Company
InventorsROBERT JAMES PASTERIS, JEFFREY KEITH LONG, SRINIVAS CHITTABOINA
Life of this patent
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Abstract
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, wherein A1, A2, R1, R2, R3, R4a, R4b, L, R5 and R6 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.
Claims9
A compound selected from Formula 1, N-oxides and salts thereof,
- wherein
- A1 is CH or N;
- A2 is CH or N;
- R1 is hydrogen, halogen, SH, CN, SCN, C1-C6 alkylthio, C1-C6 haloalkylthio, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-C6 alkynylthio or C2-C6 haloalkynylthio;
- R2 is C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, each optionally substituted with up to 5 substituents independently selected from R2a;
- or C3-C8 cycloalkyl optionally substituted with up to 5 substituents independently selected from R2b;
- or ZQ1;
- each R2a is independently hydroxy, halogen, cyano, nitro, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
- each R2b is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;
- Z is a direct bond, CH2 or CH2O wherein the carbon atom is attached to the remainder of Formula 1 and the oxygen atom is attached to Q1;
- Q1 is a phenyl ring;
- or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R9a on carbon atom ring members and R9b on nitrogen atom ring members;
- R3 is hydrogen, CHO, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkoxycarbonyl, C2-C4 haloalkoxycarbonyl, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkynyl or C2-C4 alkoxyalkyl;
- R4a is hydrogen, halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl or C1-C2 alkoxy;
- R4b is hydrogen, halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl or C1-C2 alkoxy;
- L is a direct bond;
- or a 1-, 2-, 3- or 4-membered saturated, partially unsaturated or fully unsaturated chain containing chain members selected from carbon atoms and up to 2 heteroatoms independently selected from up to 1 O, up to 1 S, and up to 2 N, wherein the chain is optionally substituted with up to 4 substituents independently selected from R7a on carbon atom chain members and R7b on nitrogen atom chain members;
- R5 is C1-C8 alkyl, C1-C8 haloalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C10 alkylcycloalkylalkyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 haloalkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C3-C8 dialkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C3-C8 alkoxycarbonylalkyl, C3-C8 haloalkoxycarbonylalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylamino, C1-C8 haloalkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C8 alkylsulfonylamino, C1-C8 haloalkylsulfonylamino or C3-C8 trialkylsilyl;
- or G;
- G is phenyl or naphthalenyl, each optionally substituted with up to 5 substituents independently selected from R8a;
- or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 5 substituents independently selected from R8aon carbon atom ring members and R8b on nitrogen atom ring members;
- R6 is hydrogen, halogen, cyano, C1-C2 alkyl or C1-C2 haloalkyl;
- or
- R6 and R4a are taken together with the linking atoms to which they are attached to form a 3- to 7-membered ring containing ring members, in addition to the linking atoms, selected from carbon atoms and up to 3 heteroatoms independently selected from up to 1 O, up to 1 S and up to 1 N atom, the ring optionally substituted with up to 2 substituents independently selected from halogen, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy and C1-C2 haloalkoxy on carbon atom ring members and cyano, C1-C2 alkyl and C1-C2 alkoxy on nitrogen atom ring members;
- each R7a is independently cyano, halogen, hydroxy, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;
- each R7b is independently cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C2-C3 alkylcarbonyl;
- each R8a is independently halogen, cyano, hydroxy, amino, nitro, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C2-C4 alkoxyalkyl, C2-C4 hydroxyalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkylcarbonyloxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C2-C4 alkylcarbonylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C6 dialkylamino, C3-C6 cycloalkylamino, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C2-C4 alkylaminocarbonyl, C3-C6 dialkylaminocarbonyl, C3-C6 trialkylsilyl or Q2;
- each R8b is independently cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
- each Q2 is independently a phenyl, benzyloxy, phenoxy, benzylthio, phenylthio or a 5- or 6-membered heteroaromatic ring each optionally substituted with up to 3 substituents independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
- each R9a is independently hydroxy, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or phenoxy;
- and
- each R9b is independently cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C2-C6 alkylcarbonyl;
- provided that
- a) when A1 is N then A2 is N;
- b) L is other than —O—, —S— or —NR7b—;
- c) when Z is a direct bond, then Q1 is bonded to the remainder of Formula 1 via a carbon atom;
- d) when L is a direct bond, then R5 is bonded to the remainder of Formula 1 via a carbon atom;
- and
- e) when Z is CH2, then Q1 is other than a 6-membered heteroaromatic ring.
36 more elements
Dependencies are inferred from the claim text.