Pyridine-based compound including isoxazoline ring and use thereof as herbicide

2:

• The compound of claim 1, wherein R1 is H, a methyl group, an ethyl group, or a benzyl group;
• R2 is H or a methyl group;
• n is an integer of 0 to 1;
• X is Cl or —NR3R4 wherein R3 and R4 are each independently H, a C1 to C2 alkyl group, or a C(O)methyl group;
• Y is CH, CCl, CF, or N;
• and
• Z is H, Br, Cl, a C1 to C4 alkyl group, a C1 to C4 halo alkyl group, a C1 to C4 alkoxy group, a C1 to C4 alkoxy carbonyl group, a phenyl group substituted with at least one R5 wherein —R5 is F, Cl, or a methoxy group;
• or a heterocyclic group selected from the group consisting of

3:

• The compound of claim 1, wherein R1 is H, a methyl group, an ethyl group, or a benzyl group;
• R2 is H or a methyl group;
• n is an integer of 0 to 1;
• X is —NR3R4 wherein R3 and R4 are each independently H, a methyl group, or a C(O)methyl group;
• Y is CH, CCl, CF, or N;
• and
• Z is H, Br, Cl, a methyl group, a tert-butyl group, or a trifluoromethyl group.

4:

• The compound of claim 1, wherein the compound is any one compound selected from the group consisting of:
• methyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-methyl-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-methyl-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-bromo-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-bromo-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-trifluoromethyl-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-trifluoromethyl-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-tert-butyl-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-tert-butyl-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(4,5-dihydroisoxazol-5-yl)picolinate;
• methyl 4-amino-3-chloro-6-(3-bromo-5-methyl-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3-chloro-6-(3-bromo-5-methyl-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-chloro-5-methyl-4,5-dihydroisoxazol-5-yl)picolinate;
• methyl 4-amino-6-((3-chloro-4,5-dihydroisoxazol-5-yl)methyl)-3-chloropicolinate;
• 4-amino-6-((3-chloro-4,5-dihydroisoxazol-5-yl)methyl)-3-chloropicolinic acid;
• ethyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• isopropyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• isobutyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• benzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-methylbenzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-trifluoromethylbenzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-methoxybenzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-bromobenzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-fluorobenzyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• phenyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-picolinate;
• lithium 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• sodium 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• ethyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• isopropyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• isobutyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• benzyl 4-amino-3-chloro-6-(3-bromo-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-methylbenzyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• 4-trifluoromethylbenzyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• 4-methoxybenzyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• 4-bromobenzyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• 4-fluorobenzyl 4-amino-6-(3-bromo-4,5-dihydroisoxazol-5-yl)-3-chloropicolinate;
• phenyl 4-amino-3-chloro-6-(3-bromo-4,5-dihydroisoxazol-5-yl)picolinate;
• methyl 6-amino-5-chloro-2-(3-bromo-4,5-dihydroisoxazol-5-yl)pyrimidine-4-carboxylate;
• 6-amino-5-chloro-2-(3-bromo-4,5-dihydroisoxazol-5-yl)pyrimidine-4-carboxylic acid;
• methyl 6-amino-5-chloro-2-(3-chloro-4,5-dihydroisoxazol-5-yl)pyrimidine-4-carboxylate;
• 6-amino-5-chloro-2-(3-chloro-4,5-dihydroisoxazol-5-yl)pyrimidine-4-carboxylic acid;
• methyl 3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-4-(methylamino)picolinate;
• methyl 3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-4-(dimethylamino)picolinate;
• 3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-4-(dimethylamino)picolinic acid;
• methyl 4-amino-3,5-dichloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinate;
• 4-amino-3,5-dichloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)picolinic acid;
• methyl 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-5-fluoropicolinate;
• 4-amino-3-chloro-6-(3-chloro-4,5-dihydroisoxazol-5-yl)-5-fluoropicolinic acid;
• and
• agrochemically acceptable salts thereof.

8:

• A herbicide composition comprising:
• a compound selected from the group consisting of a pyridine-based compound containing an isoxazoline ring represented by Formula 1, agrochemically acceptable salt thereof, and a combination of the pyridine-based compound and the agrochemically acceptable salt thereof, as an active ingredient, in an amount of about 0.1 wt % to about 99.9 wt % based on a total weight of the herbicide;
• and
• at least one additive selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, in an amount of about 0.1 wt % to about 99.9 wt % based on a total weight of the herbicide
• wherein, in Formula 1, R1 is H, a C1 to C4 alkyl group, or a benzyl group;
• R2 is H or a C1 to C2 alkyl group;
• n is an integer of 0 to 3;
• X is a halogen or —NR3R4 wherein R3 and R4 are each independently H, a C1 to C2 alkyl group, or a C(O)methyl group;
• Y is CH, C-halogen, or N;
• and
• Z is H, halogen, a C1 to C4 alkyl group, a C1 to C4 halo alkyl group, a C1 to C4 alkoxy group, a C1 to C4 alkoxy carbonyl group, a phenyl group substituted with at least one R5 wherein R5 is halogen, a C1 to C4 alkyl group, a C1 to C4 alkoxy group, or a C1 to C4 halo alkyl group, or a heterocyclic group wherein a heterocyclic group is a 5-membered or 6-membered saturated or unsaturated ring containing at least one selected from N, O, and S.

11:

• A method of preparing a pyridine-based compound containing an isoxazoline ring represented by Formula 1, the method comprising:
• reacting a compound represented by Formula 2 with a compound represented by Formula 3:
• wherein, in Formulae 1, 2 and 3, R1 is H, a C1 to C4 alkyl group, or a benzyl group;
• R2 is H or a C1 to C2 alkyl group;
• n is an integer of 0 to 3;
• X is a halogen or —NR3R4 wherein R3 and R4 are each independently H, a C1 to C2 alkyl group, or a C(O)methyl group;
• Y is CH, C-halogen, or N;
• and
• Z is H, halogen, a C1 to C4 alkyl group, a C1 to C4 halo alkyl group, a C1 to C4 alkoxy group, a C1 to C4 alkoxy carbonyl group, a phenyl group substituted with at least one R5 wherein R5 is halogen, a C1 to C4 alkyl group, a C1 to C4 alkoxy group, or a C1 to C4 halo alkyl group, or a heterocyclic group wherein a heterocyclic group is a 5-membered or 6-membered saturated or unsaturated ring containing at least one selected from the group consisting of N, O, and S.