# US 9,516,880 B2 · Herbicidal and fungicidal 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides

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- Number: US 9,516,880 B2
- Document ID: US9516880B2
- Status: Granted
- Kind: B2
- Application number: 14/430,066
- Filed: 2013-09-23
- Published: 2015-09-03
- Granted: 2016-12-13
- Earliest claimed: 2012-09-25
- Assignees: Bayer CropScience AG
- Applicants: Bayer Cropscience AG
- Inventors: Klaus Bernhard Haaf; Lothar Willms; Hansjoerg Dietrich; Elmar Gatzweiler; Christopher Hugh Rosinger; Dirk Schmutzler; Ulrike Wachendorff-Neumann; Marie-Claire Grosjean-Cournoyer; Helene Lachaise; Philippe Rinolfi; Stephane Brunet
- Web page: https://patentgrep.com/patent/US9516880B2

## CPC

- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61P 17/00: Drugs for dermatological disorders
- A61P 31/10: Antimycotics
- C07D 261/04: having one double bond between ring members or between a ring member and a non-ring member
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Herbicidally and fungicidally active 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides of the formula (I) are described. In this formula (I), X, X2 to X6, R1 to R4 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

### Claim 1

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide and/or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide of the formula (I) and/or a salt thereof
in which
R1 and R2 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, or (C1-C4)-alkyl or (C1-C4)-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine and cyano,
or
R1 and R2 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;
R3 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C1-C4)-alkoxy and hydroxyl,
R4 is hydrogen, cyano,
or (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-alkenyl or (C3-C8)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl and (C1-C6)-alkoxy,
A is a bond or a divalent unit from the group consisting of
R10, R11, R12, R13, R14 and R15 are each independently
hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R8, CONR6R8, R5, or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,
or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;
Y is oxygen or sulfur;
X is hydrogen, cyano, hydroxyl, X1,
or
(C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR7, X1, OX1, NHX1, S(O)nR5, SO2NR6R7, SO2NR6COR8, CO2R8, CONR6R8, COR6, CONR8SO2R5, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, OCONR6R8, OCSNR6R8, POR9R9 and C(R6)═NOR8,
or
X, A and R4 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring containing, as well as this nitrogen atom, k carbon atoms, n oxygen atoms, p sulfur atoms and p elements from the group consisting of NR7 and NCOR7 as ring atoms, where one carbon atom bears p oxo groups;
X1 is a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring which is formed from r carbon atoms, s nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by s radicals from the group consisting of R6, R6a, R8 and R9, where the sulfur atoms and carbon atoms bear n oxo groups;
or X1 is phenyl substituted by m radicals from the group consisting of R6, R6a, R8 and R9;
X2, X4 and X6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,
or (C1-C4)-alkyl, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy or (C1-C4)-alkylcarbonyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C4)-alkoxy;
X3 and X5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF5, CONR8SO2R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)═NOR8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, OCONR6R8, OSO2R5, S(O)nR5, SO2NR6R8, OSO2NR6R8,
or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,
or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;
R5 is (C1-C6)-alkyl or (C3-C6)-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;
R6 is hydrogen or R5;
R6a is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nR5, or (C1-C6)-alkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy;
R7 is hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy;
R8 is R7,
R9 is (C1-C3)-alkyl or (C1-C3)-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.

### Claim 2 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1,
in which
R1 and R2 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, or (C1-C4)-alkyl or (C1-C4)-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine and cyano,
or
R1 and R2 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;
R3 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, (C1-C4)-alkoxy and hydroxyl,
R4 is hydrogen, cyano,
or (C1-C8)-alkyl or (C3-C8)-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl and (C1-C6)-alkoxy;
A is a bond or a divalent unit from the group consisting of
R10, R11, R12, R13, R14 and R15 are each independently
hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R8, CONR6R8, R5,
or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,
or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;
Y is oxygen or sulfur;
X is hydrogen, cyano, hydroxyl, X1,
or
(C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR7, X1, OX1, NHX1, S(O)nR5, SO2NR6R7, SO2NR6COR8, CO2R8, CONR6R8, COR6, CONR8SO2R5, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, OCONR6R8, OCSNR6R8, POR9R9 and C(R6)═NOR8,
or
X, A and R4 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring containing, as well as this nitrogen atom, k carbon atoms, n oxygen atoms, p sulfur atoms and p elements from the group consisting of MC and NCOR7 as ring atoms, where one carbon atom bears p oxo groups;
X1 is a ring, substituted by s radicals from the group consisting of R6, R6a, R8 and R9, from the group consisting of
or X1 is phenyl substituted by m radicals from the group consisting of R6, R6a, R8 and R9;
X2, X4 and X6 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,
or (C1-C4)-alkyl, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C4)-alkynyloxy or (C1-C4)-alkylcarbonyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C4)-alkoxy;
X3 and X5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, SF5, CONR8SO2R5, CONR6R8, COR6, CO2R8, CONR6R8, C(R6)═NOR8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, OCONR6R8, OSO2R5, S(O)nR5, SO2NR6R8, OSO2NR6R8,
or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano,
or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;
R5 is (C1-C6)-alkyl or (C3-C6)-cycloalkyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;
R6 is hydrogen or R5;
R5a is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nR5, or (C1-C6)-alkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy;
R7 is hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy;
R8 is R7,
R9 is (C1-C3)-alkyl or (C1-C3)-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;
s is 0, 1, 2, 3 or 4.

### Claim 3 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1,
in which
R1 and R2 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, or (C1-C4)-alkyl substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine and cyano;
R3 is (C1-C4)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (C1-C2)-alkoxy, A is a bond or a divalent unit from the group consisting of CH2, CH2CH2, CHCH3, CH2CH2CH2, CH(CH2CH3), CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C(iPr)CH3, CH(CH2iPr)CH2, CH2CH═CH, C(CH3)2C≡C, CH(CF3)CH2, CH(CH3)CH2O, CH2CH2O, CH(cPr)CH2O, CH(CH2OCH3),CH(CH2CH2SCH3), CH(COOH), CH(COOCH3), CH(COOH)CH2, CH(COOCH3)CH2, CH2COH(CF3), CH(CONHCH3), CH(CONHCH3)CH2 and CH2CH2CONHCH2;
R4 is hydrogen or (C1-C8)-alkyl;
Y is oxygen or sulfur;
X is hydrogen, cyano, hydroxyl, X1,
or
(C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl each substituted by m radicals from the group consisting of fluorine, chlorine, cyano, hydroxyl, OR7, X1, OX1, NHX1, S(O)nR5, CO2R8, CONR6R8, CONR8SO2R5 and POR9R9;
X1 is a ring, substituted by s radicals from the group consisting of R6, R6a, R8 and R9, from the group consisting of
or X1 is phenyl substituted by m radicals from the group consisting of R6, R6a, R8 and R9;
X2, X4 and X6 are each independently hydrogen, fluorine, or chlorine,
or (C1-C4)-alkyl or (C1-C4)-alkoxy each substituted by m radicals from the group consisting of fluorine, chlorine, cyano and (C1-C4)-alkoxy;
X3 and X5 are each independently hydrogen, fluorine, chlorine, bromine, cyano,
or (C1-C6)-alkyl substituted by m radicals from the group consisting of fluorine and chlorine,
or (C1-C6)-alkoxy substituted by m radicals from the group consisting of fluorine and chlorine;
R5 is methyl or ethyl;
R6 is hydrogen or R5;
R6a is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nR5, or (C1-C6)-alkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano and (C1-C2)-alkoxy;
R7 is hydrogen or (C1-C6)-alkyl substituted by m radicals from the group consisting of fluorine and chlorine;
R8 is R7,
R9 is (C1-C3)-alkoxy;
m is 0, 1, 2 or 3;
n is 0, 1 or 2;
s is 0, 1, 2, 3 or 4.

### Claim 4 (depends on 1)

A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) and/or salt as claimed in claim 1.

### Claim 5 (depends on 4)

The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.

### Claim 6 (depends on 4)

The herbicidal composition as claimed in claim 4, comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 7)

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

### Claim 9 (depends on 6)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

A compound of the formula (I) and/or salt as claimed in claim 1 capable of being used for controlling one or more unwanted plants.

### Claim 12 (depends on 10)

The method as claimed in claim 10, wherein the compound of the formula (I) and/or salt is used for controlling one or more unwanted plants in one or more crops of one or more useful plants.

### Claim 13 (depends on 12)

The method as claimed in claim 12, wherein the useful plants are one or more transgenic useful plants.

### Claim 14 (depends on 1)

A fungicidal composition, comprising a fungicidally active amount of at least one compound of the formula (I) and/or salt as claimed in claim 1.

### Claim 15 (depends on 14)

The fungicidal composition as claimed in claim 14 in a mixture with one or more formulation auxiliaries.

### Claim 16 (depends on 14)

The fungicidal composition as claimed in claim 14, comprising at least one further pesticidally active compound selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

### Claim 17 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1, in which
X2, X4, X6, R1, R2, and R4 each represent hydrogen;
R3 represents methyl; and
Y represents oxygen.

### Claim 18 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1, in which
X2 is hydrogen;
X3 is hydrogen;
X4 is hydrogen;
X5 is cyano;
X6 is hydrogen;
R1 is hydrogen;
R2 is hydrogen;
R3 is methyl;
R4 is hydrogen;
Y is oxygen;
A is a bond; and
X is cyclopropyl.

### Claim 19 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1, which is the compound 1.20-5 wherein
X2 is hydrogen;
X3 is chlorine;
X4 is hydrogen;
X5 is chlorine;
X6 is hydrogen;
R1 is hydrogen;
R2 is hydrogen;
R3 is methyl;
R4 is hydrogen;
Y is oxygen;
A-X is isopropyl.

### Claim 20 (depends on 1)

A 5-oxy-substituted 3-phenylisoxazoline-5-carboxamide or 5-oxy-substituted 3-phenylisoxazoline-5-thioamide and/or salt as claimed in claim 1, which is the compound 1.20-210
X2 is hydrogen;
X3 is chlorine;
X4 is hydrogen;
X5 is chlorine;
X6 is hydrogen;
R1 is hydrogen;
R2 is hydrogen;
R3 is methyl;
R4 is hydrogen;
Y is oxygen;
A-X is