IP Library › Granted Patent US 9,078,442

Granted Patent B2

US 9,078,442 · App. 14/006,280 · Granted Jul 14, 2015

Herbicidally and fungicidally active 3-phenylisoxazoline-5-carboxamides and 3-phenylisoxazoline-5-thioamides

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Quick Facts

Patent No.: US 9,078,442
App. No.: 14/006,280
Granted: Jul 14, 2015
Kind: B2

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Abstract

3-Phenylisoxazoline-5-carboxamides and 3-phenylisoxazoline-5-thioamides of the formula (I) and their use as herbicides and fungicides are described. In this formula (I), X, X 2 to X 6 , R 1 to R 4 are radicals such as hydrogen, halogen and organic radicals such as substituted alkyl. A is a bond or a divalent unit. Y is a chalcogen.

Claims (222)

1. A 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide of formula (I) and/or a salt thereof

in which

R 1 and R 2 independently of one another are each hydrogen, fluorine, chlorine, bromine, iodine, cyano, or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy substituted by in each case m radicals selected 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 attached form a saturated, partially or fully unsaturated three-, four- or 5-membered ring which is constructed of 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 substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 4 )-alkoxy and hydroxy,

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

R 4 is hydrogen, cyano,

or (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C 1 -C 6 )-alkoxy;

A is a bond or a divalent unit from the group consisting of

R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are each independently of one another hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, CO 2 R 8 , CONR 6 R 8 , R 5 , or (C 1 -C 6 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy 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 of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 2 )-alkoxy,

Y is oxygen or sulfur;

X is hydrogen, cyano, hydroxy, X 1 ,

(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, OR 7 , X 1 , OX 1 , NHX 1 , S(O) n R 5 , SO 2 NR 6 R 7 , SO 2 NR 6 R 8 , CO 2 R 8 , CONR 6 R 8 , COR 6 , CONR 8 SO 2 R 5 , NR 6 R 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 , OCSNR 6 R 8 , POR 9 R 9 and C(R 6 )═NOR 8 ,

X, A and R 4 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which, in addition to this nitrogen atom, contains k carbon atoms, n oxygen atoms, p sulphur atoms and p elements selected from the group consisting of NR 7 and NCOR 7 as ring atoms, where a carbon atom carries p oxo groups;

X 1 is a 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring which is constructed of r carbon atoms, s nitrogen atoms, n sulphur atoms and n oxygen atoms and which is substituted by n radicals selected from the group consisting of R 6 , R 6a , R 8 and R 9 ;

X 2 , X 4 and X 6 independently of one another are each 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 of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 4 )-alkoxy;

X 3 is fluorine, chlorine, bromine, iodine, hydroxy, 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 of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxy and cyano,

X 5 is hydrogen or X 3 ;

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

R 6 is hydrogen or R 5 ;

R 6a is fluorine, chlorine, bromine, iodine, cyano, hydroxy, S(O) n R 5 or (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy or (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;

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 of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

k is 3, 4, 5 or 6;

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

p is 0 or 1;

q is 3, 4 or 5;

r is 1, 2, 3, 4 or 5;

s is 0, 1, 2, 3, or 4;

with the proviso that X 3 and X 4 are not both substituted or unsubstituted alkoxy.

2. A 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide and/or salt thereof of formula (I)

in which

R 4 is hydrogen, cyano,

or (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C 1 -C 6 )-alkoxy;

A is a bond or a divalent unit selected from the group consisting of

Y is oxygen or sulfur;

X is hydrogen, cyano, hydroxy, X 1 ,

X 1 is a ring, substituted by n radicals selected from the group consisting of R 6 , R 6a , R 8 and R 9 , said ring being selected from the group consisting of

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

X 3 is fluorine, chlorine, bromine, iodine, hydroxy, cyano, nitro, SF 5 , CONR 8 SO 2 R 5 , CONR 6 R 8 , COR 8 , 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 or X 3 ;

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

R 6 is hydrogen or R 5 ;

R 6a is fluorine, chlorine, bromine, iodine, cyano, hydroxy, S(O) n R 5 or (C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy or (C 2 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

k is 3, 4, 5 or 6;

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 X 3 and X 4 are not both substituted or unsubstituted alkoxy.

3. The 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide of formula (I)

and/or salt thereof in which

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

R 3 is fluorine, chlorine, cyano,

or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine and chlorine,

or (C 1 -C 6 )-alkylcarbonyl which is substituted by at least one m radical selected from the group consisting of fluorine and chlorine;

A is a bond or a divalent unit selected from the group consisting of CH 2 , CH 2 CH 2 , CHCH 3 , CH 2 CH 2 CH 2 , CH(CH 2 CH 3 ), CH(CH 3 )CH 2 , C(CH 3 ) 2 , C(CH 3 ) 2 CH 2 , C(iPr)CH 3 , CH(CH 2 iPr)CH 2 , CH 2 CH═CH, C(CH 3 ) 2 C≡C, CH(CF 3 )CH 2 , CH(CH 3 )CH 2 O, CH 2 CH 2 O, CH(cPr)CH 2 O, CH(CH 2 OCH 3 ), CH(CH 2 CH 2 SCH 3 ), CH(COOH), CH(COOCH 3 ), CH(COOH)CH 2 , CH(COOCH 3 )CH 2 , CH 2 COH(CF 3 ), CH(CONHCH 3 ), CH(CONHCH 3 )CH 2 and CH 2 CH 2 CONHCH 2 ;

R 4 is hydrogen or (C 1 -C 8 )-alkyl;

Y is oxygen or sulfur;

X is hydrogen, cyano, hydroxy, X 1 ,

(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, cyano, hydroxy, OR 7 , X 1 , OX 1 , NHX 1 , S(O) n R 5 , CO 2 R 8 , CONR 6 R 8 , CONR 8 SO 2 R 5 and POR 9 R 9 ;

X 1 is a ring, substituted by n radicals selected from the group consisting of R 6 , R 6a , R 8 and R 9 , said ring being selected from the group consisting of

X 2 , X 4 and X 6 independently of one another are each hydrogen, fluorine or chlorine, or (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy, each of which is substituted by m radicals selected 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 which is in each case substituted by m radicals selected from the group consisting of fluorine and chlorine;

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

X 5 is hydrogen or X 3 ;

R 5 is methyl or ethyl;

R 6 is hydrogen or R 5 ;

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

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkoxy;

m is 0, 1, 2 or 3;

n is 0, 1 or 2;

with the proviso that X 3 and X 4 are not both substituted or unsubstituted alkoxy.

4. A herbicidal composition which comprises a herbicidally effective amount of at least one compound of formula (I) and/or salt thereof as claimed in claim 1 .

5. The herbicidal composition as claimed in claim 4 , in a mixture with at least one formulation auxiliary.

6. The herbicidal composition as claimed in claim 4 , comprising at least one further pesticidally active compound selected from the group consisting of an insecticide, an acaricide, a herbicide, a fungicide, a safener and a growth regulator.

7. The herbicidal composition as claimed in claim 6 , comprising a safener.

8. The herbicidal composition as claimed in claim 7 , where the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifenethyl, cloquintocet-mexyl, benoxacor and dichlormid.

9. The herbicidal composition as claimed in claim 6 , comprising a further herbicide.

10. A 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide of formula (Ia)

in which

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or (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 substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 4 )-alkoxy and hydroxy,

R 4 is hydrogen, cyano, hydroxy,

or (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C 1 -C 6 )-alkoxy;

A is a bond or a divalent unit selected from the group consisting of

R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are each independently of one another hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, CO 2 R 8 , CONR 6 R 8 , R 5 ,

Y is oxygen or sulfur;

X is hydrogen, cyano, hydroxy, X 1 ,

(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, OR 7 , X 1 , OX 1 , NHX 1 , S(O) n R 5 , SO 2 NR 6 R 7 , SO 2 NR 6 R 8 , CO 2 R 8 , CONR 6 R 8 , COR 8 , CONR 8 SO 2 R 5 , NR 6 R 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 , OCSNR 6 R 8 , POR 9 R 9 and C(R 6 )═NOR 8 ,

X 1 is a 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring which is constructed of r carbon atoms, s nitrogen atoms, n sulphur atoms and n oxygen atoms and which is substituted by at least one n radical selected from the group consisting of R 6 , R 6a , R 8 and R 9 ;

or phenyl which is substituted by n radicals selected from the group consisting of R 6 , R 8 and R 9 ;

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

X 3 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, 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 ,

X 5 is hydrogen or X 3 ;

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

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

k is 3, 4, 5 or 6;

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;

r is 1, 2, 3, 4 or 5;

s is 0, 1, 2, 3 or 4;

capable of being used for controlling an unwanted plant.

11. A 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide of formula (Ia) capable of being used for controlling an unwanted plant

in which

R 3 is fluorine, chlorine, cyano, (C 1 -C 3 )-alkylcarbonyloxy or (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 substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 4 )-alkoxy and hydroxy,

R 4 is hydrogen, cyano, hydroxy,

or (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl substituted by in each case m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy and (C 1 -C 6 )-alkoxy;

A is a bond or a divalent unit selected from the group consisting of

R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are each independently of one another hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, CO 2 R 8 , CONR 6 R 8 , R 5 ,

Y is oxygen or sulfur;

X is hydrogen, cyano, hydroxy, X 1 ,

(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl substituted by in each case at least one m radical selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, X 1 , OX 1 , NHX 1 , S(O) n R 5 , SO 2 NR 6 R 7 , SO 2 NR 6 R 8 , CO 2 R 8 , CONR 6 R 8 , COR 8 , CONR 8 SO 2 R 5 , NR 6 R 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 , OCSNR 6 R 8 , POR 9 R 9 and C(R 6 )═NOR 8 ,

X 1 is a ring, substituted by n radicals selected from the group consisting of R 6 , R 6a , R 8 and R 9 , wherein the ring is selected from the group consisting of

or phenyl which is substituted by n radicals selected from the group consisting of R 6 , R 8 , and R 9 ;

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

X 5 is hydrogen or X 3 ;

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

R 6 is hydrogen or R 5 ;

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

k is 3, 4, 5 or 6;

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. A 3-phenylisoxazoline-5-carboxamide or 3-phenylisoxazoline-5-thioamide of formula (Ia)

capable of being used for controlling an unwanted plant in which

R 3 is fluorine, chlorine or cyano,

or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, each of which is substituted by m radicals from the group consisting of fluorine and chlorine,

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

R 4 is hydrogen, hydroxy or (C 1 -C 8 )-alkyl;

Y is O or S;

X is hydrogen, cyano, hydroxy, X 1 ,

(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, cyano, hydroxy, X 1 , OX 1 , NHX 1 , S(O) n R 5 , CO 2 R 8 , CONR 6 R 8 , CONR 8 SO 2 R 5 and POR 9 R 9 ;

X 1 is a ring, substituted by n radicals from the group consisting of R 6 , R 6a , R 8 and R 9 , wherein the the ring is selected from the group consisting of

or phenyl which is substituted by n radicals selected from the group consisting of R 6 , R 8 and R 9 ;

X 3 is hydrogen, fluorine, chlorine, bromine, cyano,

or (C 1 -C 6 )-alkyl which is in each case substituted by m radicals selected from the group consisting of fluorine and chlorine;

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

X 5 is hydrogen or X 3 ;

R 5 is methyl or ethyl;

R 6 is hydrogen or R 5 ;

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

R 8 is R 7 ;

R 9 is (C 1 -C 3 )-alkoxy;

m is 0, 1, 2 or 3;

n is 0, 1 or 2.

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

14. A compound of formula (I) and/or salt thereof as claimed in claim 1 , capable of being used for controlling an unwanted plant.

15. A compound of formula (I) and/or salt, capable of being used as claimed in claim 14 , wherein said compound of formula (I) is used for controlling an unwanted plant in a crop of a useful plant.

16. A compound of formula (I) and/or salt thereof capable of being used as claimed in claim 15 , wherein said useful plant is a transgenic useful plant.

17. A fungicidal composition which comprises a fungicidally effective amount of at least one compound of the formula (I) and/or salt thereof as claimed in claim 1 .

18. The fungicidal composition as claimed in claim 17 , in a mixture with at least one formulation auxiliary.

19. The fungicidal composition as claimed in claim 17 , comprising at least one further pesticidally active compound selected from the group consisting of an insecticide, an acaricide, a herbicide, a fungicide, a safener and a growth regulator.

Assignments (3)

NUNC PRO TUNC ASSIGNMENT Recorded Jul 4, 2023

From: BAYER INTELLECTUAL PROPERTY GMBH

To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT

Reel/Frame 064198/0823 →

CHANGE OF ADDRESS Recorded Jun 12, 2023

From: BAYER INTELLECTUAL PROPERTY GMBH

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 064021/0344 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2013

From: WILLMS, LOTHAR; SCHMITT, MONIKA H; FRENZEL, THOMAS; HAAF, KLAUS BERNHARD; HAEUSER-HAHN, ISOLDE; HEINEMANN, INES; GATZWEILER, ELMAR; ROSINGER, CHRISTOPHER HUGH; KEHNE, HEINZ; DITTGEN, JAN; FEUCHT, DIETER; HILLS, MARTIN JEFFREY; RINOLFI, PHILIPPE

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 031769/0962 →