IP Library › Granted Patent US 9,585,392

Granted Patent B2

US 9,585,392 · App. 14/430,018 · Granted Mar 7, 2017

3-phenylisoxazolin derivatives with herbicidal action

Inventors: Birgit Kuhn (Kelkheim, DE); Lothar Willms (Hofheim, DE); Thomas Frenzel (Cologne, DE); Klaus Bernhard Haaf (Kelkheim, DE); Stephen David Lindell (Kelkheim, DE); Hansjörg Dietrich (Liederbach am Taunus, DE); Dirk Schmutzler (Hattersheim, DE); Elmar Gatzweiler (Bad Nauheim, DE); Christopher Hugh Rosinger (Hofheim, DE)

Assignee: BAYER CROPSCIENCE AG

A01N43/80 C07D261/04

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Quick Facts

Patent No.: US 9,585,392
App. No.: 14/430,018
Granted: Mar 7, 2017
Kind: B2

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Abstract

3-Phenylisoxazoline derivatives of the formula (I), and the use thereof as herbicides, are described. In this formula (I), X 2 to X 6 and R 1 to R 3 are radicals such as hydrogen, halogen, and organic radicals such as substituted alkyl. W* is carboxyl, cyano or CHO.

Claims (330)

1. A 3-phenylisoxazoline derivative and/or salt thereof, of formula (I)

in which

R 1 and R 2 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine and cyano,

R 1 and R 2 together with the carbon atom to which they are bonded form a saturated or partly or fully unsaturated three-, four- or five-membered ring formed from q carbon atoms and p oxygen atoms;

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or S(O) n R 5 ,

or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 4 )-alkoxy and hydroxyl,

or (C 1 -C 6 )-alkylcarbonyl, (C 2 -C 6 )-alkenylcarbonyl or (C 3 -C 6 )-cycloalkylcarbonyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, and cyano;

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 7 is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;

R 8 is R 7 ;

W* is COOH, COOY, CN or CHO;

Y is (C 1 -C 8 )-alkyl which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl and COO—(C 1 -C 8 )-alkyl and which is interrupted by n heteroatoms from the group consisting of oxygen, sulfur and nitrogen, or

a radical from the group consisting of (cyclohex-2-en-1-one)-3-yl, (propan-1-ol)-3-yl, (2,2-dimethylpropan-1-ol)-3-yl, (methyl 2,2-dimethylpropanoate)-3-yl, (methyl propanoate)-3-yl, (ethyl propanoate)-3-yl, (ethyl butanoate)-3-yl, (ethyl (3R)-4,4,4-trifluorobutanoate)-3-yl, (butan-2-one)-4-yl, (3-methylbutan-2-one)-4-yl, (pent-3-en-2-one)-4-yl,((2S)-dimethyl butanedioate)-2-yl, (dimethyl pentanedioate)-3-yl, (methyl (2R)-2-methylpropanoate)-3-yl, 4-methoxycarbonylbenzyl, 3,5-difluorobenzyl, 3,4-difluorobenzyl, 2,6-difluorobenzyl, 5-methylpyridin-3-ylmethyl, tetrahydrofuran-3-yl and (butan-1-ol)-4-yl;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

or (C 1 -C 4 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 4 )-alkynyloxy or (C 1 -C 4 )-alkylcarbonyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 4 )-alkoxy;

X 3 is fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF 5 , CONR 8 OSO 2 R 5 , CONR 6 R 8 , COR 6 , CO 2 R 8 , CONR 6 R 8 , C(R 6 )═NOR 8 , NR 6 COR 8 , NR 6 CONR 8 R 8 , NR 6 CO 2 R 8 , NR 6 SO 2 R 8 , NR 6 SO 2 NR 6 R 8 , OCONR 6 R 8 , OSO 2 R 5 , R 5 , S(O) n R 5 , SO 2 NR 6 R 8 , OSO 2 NR 6 R 8 ,

or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,

or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkoxy (C 2 -C 6 )-alkenyloxy or (C 2 -C 6 )-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 2 )-alkoxy;

X 5 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF 5 , CONR 8 SO 2 R 5 , CONR 6 R 8 , COR 6 , CO 2 R 8 , CONR 6 R 8 , C(R 6 )═NOR 8 , NR 6 COR 8 , NR 6 CONR 8 R 8 , NR 6 CO 2 R 8 , NR 6 SO 2 R 8 , NR 6 SO 2 NR 6 R 8 , OCONR 6 R 8 , OSO 2 R 5 , R 5 , S(O) n R 5 , SO 2 NR 6 R 8 , OSO 2 NR 6 R 8 ,

or (C 1 -C 6 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,

or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkoxy, (C 2 -C 6 )-alkenyloxy or (C 2 -C 6 )-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 2 )-alkoxy;

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2;

p is 0 or 1;

q is 3, 4 or 5;

with the proviso that

a) X 3 and X 4 are not both substituted or unsubstituted alkoxy,

b) in the compounds in which R 3 is methyl and W* is COOH, X 5 is not hydrogen, and

c) the compounds methyl 3-(3-cyanophenyl)-5-(isopropoxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, methyl 5-(butoxymethyl)-3-(3-cyanophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, methyl 3-(3-cyanophenyl)-5-(methoxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, methyl 3-(3-cyanophenyl)-5-(2-methoxyethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, 3-(3-cyanophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid, methyl 3-(3-cyanophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate, ethyl 3-(3-cyanophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate, methyl 5-methyl-3-(3-nitrophenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate, methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate and ethyl 3-(3-chlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate are excluded.

2. A 3-phenylisoxazoline derivative and/or salt as claimed in claim 1 , in which

R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 1 -C 6 )-alkyl or halo-(C 2 -C 6 )-alkenyl;

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

W* is COOH or COOP;

Y is (C 1 -C 6 )-alkyl which is substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl and COO—(C 1 -C 4 )-alkyl and which is interrupted by n oxygen atoms, or

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

X 3 is fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF 5 , CONR 8 SO 2 R 5 , CONR 6 R 8 , COR 6 , CO 2 R 8 , CONR 6 R 8 , C(R 6 )═NOR 8 , NR 6 COR 8 , NR 6 CONR 8 R 8 , NR 6 CO 2 R 8 , NR 6 SO 2 R 8 , NR 6 SO 2 NR 6 R 8 , OCONR 6 R 8 , OSO 2 R 5 , R 5 , S(O) n R 5 , SO 2 NR 6 R 8 , OSO 2 NR 6 R 8 ,

or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2;

with the proviso that

a) X 3 and X 4 are not both substituted or unsubstituted alkoxy,

b) in the compounds in which R 3 is methyl and W* is COOH, X 5 is not hydrogen, and

3. A 3-phenylisoxazoline derivative and/or salt as claimed in claim 1 , in which

R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, vinyl, (C 2 -C 4 )-alkynyl, halo-(C 1 -C 4 )-alkyl or halo-(C 2 -C 4 )-alkenyl;

R 5 is methyl or ethyl;

R 6 is hydrogen or R 5 ;

R 7 is hydrogen or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine;

R 8 is R 7 ;

W* is COOH or COOP;

a radical from the group consisting of (cyclohex-2-en-1-one)-3-yl, (propan-1-ol)-3-yl, (2,2-dimethyl propan-1-ol)-3-yl, (methyl 2,2-dimethylpropanoate)-3-yl, (methyl propanoate)-3-yl, (ethyl propanoate)-3-yl, (ethyl butanoate)-3-yl, (ethyl (3R)-4,4,4-trifluorobutanoate)-3-yl, (butan-2-one)-4-yl, (3-methylbutan-2-one)-4-yl, (pent-3-en-2-one)-4-yl,((2S)-dimethyl butanedioate)-2-yl, (dimethyl pentanedioate)-3-yl, (methyl (2R)-2-methylpropanoate)-3-yl, 4-methoxycarbonylbenzyl, 3,5-difluorobenzyl, 3,4-difluorobenzyl, 2,6-difluorobenzyl, 5-methylpyridin-3-ylmethyl, tetrahydrofuran-3-yl and (butan-1-ol)-4-yl;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, or chlorine,

or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, cyano and (C 1 -C 4 )-alkoxy;

X 3 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

X 5 is hydrogen, fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

m is 0, 1, 2 or 3;

n is 0, 1 or 2;

with the proviso that

a) X 3 and X 4 are not both substituted or unsubstituted alkoxy,

b) in the compounds in which R 3 is methyl and W* is COOH, X 5 is not hydrogen, and

4. A 3-phenylisoxazoline derivative and/or salt as claimed in claim 3 , in which

X 5 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine.

5. A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) and/or salt

in which

R 1 and R 2 together with the carbon atom to which they are bonded form a saturated or partly or fully unsaturated three-, four- or five-membered ring formed from q carbon atoms and p oxygen atoms;

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or S(O) n R 5 ,

or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkenyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 4 )-alkoxy and hydroxyl,

or (C 1 -C 6 )-alkylcarbonyl, (C 2 -C 6 )-alkenylcarbonyl or (C 3 -C 6 )-cycloalkylcarbonyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 6 )-alkoxy;

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ,

R 7 is hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkenyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;

R 8 is R 7 ,

W* is COOH, COOY, CN or CHO;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2;

p is 0 or 1;

q is 3, 4 or 5;

with the proviso that

a) X 3 and X 4 are not both substituted or unsubstituted alkoxy,

b) in the compounds in which R 3 is methyl and W* is COOH, X 5 is not hydrogen, and

6. The herbicidal composition as claimed in claim 5 in a mixture with one or more formulation auxiliaries.

7. The herbicidal composition as claimed in claim 5 , comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

8. The herbicidal composition as claimed in claim 7 , comprising a safener.

9. The herbicidal composition as claimed in claim 8 , in which the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor and dichlormid.

10. The herbicidal composition as claimed in claim 7 , comprising a further herbicide.

11. A method for controlling one or more unwanted plants comprising applying an effective amount of at least one compound of formula (Ia) to the one or more plants and/or a site of unwanted vegetation, wherein the compound of formula (Ia) is a 3-phenylisoxazoline derivative of formula (Ia)

in which

R 1 and R 2 together with the carbon atom to which they are bonded form a saturated or partly or fully unsaturated three-, four- or five-membered ring formed from q carbon atoms and p oxygen atoms;

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or S(O) n R 5 ,

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

W* is COOH, COOY, CN or CHO;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

X 3 is fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF 5 , CONR 8 SO 2 R 5 , CONR 6 R 8 , COR E , CO 2 R 8 , CONR 6 R 8 , C(R 6 )═NOR 8 , NR 6 COR 8 , NR 6 CONR 8 R 8 , NR 6 CO 2 R 8 , NR 6 SO 2 R 8 , NR 6 SO 2 NR 6 R 8 , OCONR 6 R 8 , OSO 2 R 5 , R 5 , S(O) n R 5 , SO 2 NR 6 R 8 , OSO 2 NR 6 R 8 ,

X 5 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF 5 , CONR 8 SO 2 R 5 , CONR 6 R 8 , COR E , CO 2 R 8 , CONR 6 R 8 , C(R 6 )═NOR 8 , NR 6 COR 8 , NR 6 CONR 8 R 8 , NR 6 CO 2 R 8 , NR 6 SO 2 R 8 , NR 6 SO 2 NR 6 R 8 , OCONR 6 R 8 , OSO 2 R 5 , R 5 , S(O) n R 5 , SO 2 NR 6 R 8 , OSO 2 NR 6 R 8 ,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2;

p is 0 or 1;

q is 3, 4 or 5.

12. The method as claimed in claim 11 , in which

R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 1 -C 6 )-alkyl or halo-(C 2 -C 6 )-alkenyl;

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

W* is COOH or COOP;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2.

13. The method as claimed in claim 11 , in which

R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, vinyl, (C 2 -C 4 )-alkynyl, halo-(C 1 -C 4 )-alkyl or halo-(C 2 -C 4 )-alkenyl;

R 5 is methyl or ethyl,

R 6 is hydrogen or R 5 ;

R 7 is hydrogen or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine;

R 8 is R 7 ;

W* is COOH or COOP;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, or chlorine,

or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, cyano and C 1 -C 4 )-alkoxy;

X 3 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

X 5 is hydrogen, fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

m is 0, 1, 2 or 3;

n is 0, 1 or 2.

14. The method as claimed in claim 13 , in which

X 5 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine.

15. A method for preparing a herbicidally active 3-phenylisoxazoline-5-carboxamide and/or 3-phenylisoxazoline-5-thioamide comprising employing a 3 phenylisoxazoline derivative of formula (Ia)

in which

R 1 and R 2 together with the carbon atom to which they are bonded form a saturated or partly or fully unsaturated three-, four- or five-membered ring formed from q carbon atoms and p oxygen atoms;

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or S(O) n R 5 ,

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

W* is COOH, COOY, CN or CHO;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2;

p is 0 or 1;

q is 3, 4 or 5.

16. The method as claimed in claim 15 , in which

R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 1 -C 4 )-alkyl or halo-(C 2 -C 4 )-alkenyl;

R 5 is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

W* is COOH or COOP;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,

or (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,

m is 0, 1, 2, 3, 4 or 5;

n is 0, 1 or 2.

17. The method as claimed in claim 15 , in which R 1 and R 2 are each hydrogen,

R 3 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, vinyl, (C 2 -C 4 )-alkynyl, halo-(C 1 -C 4 )-alkyl or halo-(C 2 -C 4 )-alkenyl;

R 5 is methyl or ethyl,

R 6 is hydrogen or R 5 ;

R 7 is hydrogen or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine;

R 8 is R 7 ;

W* is COOH or COOP;

X 2 , X 4 and X 6 are each independently hydrogen, fluorine, or chlorine,

or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, cyano and (C 1 -C 4 )-alkoxy;

X 3 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

X 5 is hydrogen, fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;

m is 0, 1, 2 or 3;

n is 0, 1 or 2.

18. The method as claimed in claim 17 , in which

X 5 is fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine.

19. A method for controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of formula (I) as claimed in claim 1 to the one or more plants and/or a site of unwanted vegetation.

20. A method for controlling one or more unwanted plants, comprising applying an effective amount of the composition as claimed in claim 5 to the one or more unwanted plants and/or site of unwanted vegetation.

21. A method for controlling one or more unwanted plants in one or more crops of one or more useful plants, comprising applying an effective amount of the compound as claimed in claim 2 to the one or more unwanted plants and/or site of unwanted vegetation.

22. The method as claimed in claim 21 , wherein the one or more useful plants are one or more transgenic useful plants.

23. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 1.1.462, in which

R 1 and R 2 are each hydrogen,

R 3 is methyl;

W* is COOH;

X 2 , X 4 and X 6 are each independently hydrogen; and

X 3 and X 5 are each independently fluorine.

24. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 1.1.519, in which

R 1 and R 2 are each hydrogen,

R 3 is methyl;

W* is COOH;

X 2 , X 4 and X 6 are each independently hydrogen; and

X 3 and X 5 are each independently chlorine.

25. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 1.1.580, in which

R 1 and R 2 are each hydrogen,

R 3 is methyl;

W* is COOH;

X 2 , X 4 and X 6 are each independently hydrogen;

X 3 is trifluoromethyl; and

X 5 is bromine.

26. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 1.3.4, in which

R 1 and R 2 are each hydrogen,

R 3 is 1-chlorovinyl;

W* is COOH;

X 4 , X 5 and X 6 are each independently hydrogen; and

X 3 is fluorine.

27. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 1.3.470, in which

R 1 and R 2 are each hydrogen,

R 3 is vinyl;

W* is COOH;

X 2 , X 4 and X 6 are each independently hydrogen; and

X 3 and X 5 are each independently fluorine.

28. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 2.1.33, in which

R 1 and R 2 are each hydrogen,

R 3 is methyl;

W* is COOP;

X 2 , X 4 , X 5 and X 6 are each independently hydrogen;

X 3 is acetyl; and

Y is ethyl.

29. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 2.2.472, in which

R 1 and R 2 are each hydrogen,

R 3 is difluoromethyl;

W* is COOP;

X 2 , X 4 and X 6 are each independently hydrogen;

X 3 and X 5 are each independently fluorine; and

Y is ethyl.

30. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 2.2.527, in which

R 1 and R 2 are each hydrogen,

R 3 is chloromethyl;

W* is COOP;

X 2 , X 4 and X 6 are each independently hydrogen;

X 3 and X 5 are each independently chlorine; and

Y is ethyl.

31. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 2.3.475, in which

R 1 and R 2 are each hydrogen,

R 3 is vinyl;

W* is COOP;

X 2 , X 4 and X 6 are each independently hydrogen;

X 3 is chlorine;

X 5 is fluorine; and

Y is methyl.

32. The 3-phenylisoxazoline derivative as claimed in claim 1 , which is compound 2.6.546, in which

R 1 and R 2 are each hydrogen,

R 3 is methyl;

W* is COOP;

X 2 , X 4 and X 6 are each independently hydrogen;

X 3 and X 5 are each independently chlorine; and

Y is (ethyl propanoate)-3-yl.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2015

From: KUHN, BIRGIT; WILLMS, LOTHAR; FRENZEL, THOMAS; HAAF, KLAUS BERNHARD; LINDELL, STEPHEN DAVID; DIETRICH, HANSJOERG; SCHMUTZLER, DIRK; GATZWEILER, ELMAR; ROSINGER, CHRISTOPHER HUGH

To: BAYER CROPSCIENCE AG

Reel/Frame 035614/0678 →

Priority Claims (1)

EP 12185768 · Sep 25, 2012 · regional

Continuity (1)

Related Publication 20150245615A1 · Sep 3, 2015