# US 8,785,350 B2 · Herbicidal compositions for tolerant or resistant soybean crops

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,785,350 B2
- Document ID: US8785350B2
- Status: Granted
- Kind: B2
- Application number: 13/473,935
- Filed: 2012-05-17
- Published: 2013-01-24
- Granted: 2014-07-22
- Earliest claimed: 2011-05-20
- Assignees: Bayer Intellectual Property GmbH
- Applicants: Erwin Hacker; Hansjörg Dietrich; Klaus Trabold; Elmar Gatzweiler; Frank Ziemer
- Inventors: Erwin Hacker; Hansjörg Dietrich; Klaus Trabold; Elmar Gatzweiler; Frank Ziemer
- Web page: https://patentgrep.com/patent/US8785350B2

## CPC

- A01N 57/20: containing acyclic or cycloaliphatic radicals
- 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

## Abstract

The invention provides herbicide combinations and provides for the use of herbicide combinations for control of weeds in soybean and leguminous species, wherein the particular herbicide combination comprises (A) a herbicide from the group of compounds of the formula (A1) in which Z is hydroxyl, —NHCH(CH3)CONHCH(CH3)COOH or —NHCH(CH3)CONHCH[CH2CH(CH3)2]COOH, or esters or salts thereof, (B) a herbicide of the formula (B1) in which X is N or CH and R is CO2H or a herbicide-active derivative, and the soybean and leguminous species are tolerant to the herbicides (A) and (B) present in the combination, optionally in the presence of safeners.

## Claims

### Claim 1

A herbicide combination capable of being used for control of weeds in soybean and/or leguminous species, said herbicide combination comprising:
(A) a herbicide selected from the group consisting of compounds of formula (A1)
in which Z is hydroxyl, —NHCH(CH3)CONHCH(CH3)COOH or —NHCH(CH3)CONHCH[CH2CH(CH3)2]COOH,
and/or esters and/or salts thereof,
(B) a herbicide of formula (B1)
in which R is CO2H and/or a herbicide-active derivative,
(C) a herbicide selected from the group consisting of trifluralin (C1.1), metribuzin (C1.2), clomazone (C1.3), pendimethalin (C1.4), metolachlor/S-metolachlor (C1.5), flumetsulam (C1.6), dimethenamid/dimethenamid-p (C1.7), alachlor (C1.8), sulfentrazone (C1.10), ethalfluralin (C1.11), norflurazon (C1.13), flumioxazin (C1.15), imazapyr/imazapyr-isopropylammonium (C1.16), imazamox/imazamox-ammonium (C1.17), imazaquin/imazaquin-ammonium (C1.18), carfentrazone (C.1.20), imazethapyr/imazethapyr-ammonium (C.1.21), dicamba (C.1.22), mesotrione (C.1.23), pyrasulfutole (C.1.26), tembotrione (C.1.27), isoxaflutole (C.1.28), sulcotrione (C.1.29), bentazone (C2.2), thifensulfuron (C2.3), oxyfluorfen (C2.4), lactofen (C2.5), fomesafen (C2.6), flumiclorac (C2.7), acifluorfen and the sodium salt thereof (C2.8), 2,4-DB (C2.9), 2,4-D (C2.10) chlorimuron/chlorimuron-ethyl (C2.11), cloransulam/cloransulam-methyl (C2.12), diclosulam (2.13), oxasulfuron (C2.15), sethoxydim (C3.1), cycloxydim (C3.2), clethodim (C3.3), quizalofop-P and the ethyl or tefuryl ester thereof (C4.1), fenoxaprop-P and the ethyl ester thereof (C4.2), fluazifop-P and the butyl ester thereof (C4.3), haloxyfop/haloxyfop-P and the methyl or ethyl ester thereof (C4.4), propaquizafop (C4.5), and paraquat/paraquat dichloride (C5.1),
wherein said combination exhibits herbicide efficacy greater than expected for combinations of component (C) with mixture of components (A) and (B)
and wherein the soybean species is tolerant to the herbicides (A), (B), and (C) present in the combination.

### Claim 2 (depends on 1)

The herbicide combination as claimed in claim 1, wherein said herbicide combination comprises at least one further active ingredient selected from the group consisting of safeners, plant growth regulators, herbicides, fungicides and/or insecticides.

### Claim 3 (depends on 1)

The herbicide combination as claimed in claim 1, wherein said soybean species is tolerant to said herbicide combination in the presence of a safener.

### Claim 4 (depends on 1)

The herbicide combination as claimed in claim 1, wherein said component (C) is selected from the group consisting of clethodim, cycloxydim and fenoxaprop-P-ethyl.

### Claim 5 (depends on 1)

The herbicide combination as claimed in claim 1, wherein glufosinate-ammonium is present as component (A).

### Claim 6 (depends on 1)

The herbicide combination as claimed in claim 1, wherein said soybean species is additionally tolerant to 2,4-D, dicamba, imidazolinone, and/or to herbicides which inhibit acetolactate synthase (ALS), EPSP synthase and/or hydroxyphenylpyruvate dioxygenase (HPPD).

### Claim 7 (depends on 6)

The herbicide combination as claimed in claim 6, wherein said soybean species is tolerant to 2,4-D, dicamba, at least one sulfonylurea herbicide, at least one sulfonamide herbicide, glyphosate, mesotrione, bicyclopyrone, pyrasulfutole, tembotrione, sulcotrione, topramezone and/or isoxaflutole.

### Claim 8 (depends on 1)

The herbicide combination as claimed in claim 1, wherein component (B) is selected from
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (B1.0),
methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.1),
ethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.2),
n-propyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.3),
i-propyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.4),
n-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.5),
2-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.6),
tert-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.7),
allyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.8),
2-butoxyethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.9),
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid triethylammonium salt (B1.10) and
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid potassium salt (B1.11)
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid (B1.12)
methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.13)
ethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.14)
n-propyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.15)
i-propyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.16)
n-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.17)
2-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.18)
tert-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.19)
allyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.20)
2-butoxyethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.21)
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid triethylammonium salt (B1.22), and/or
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid potassium salt (B1.23).

### Claim 9 (depends on 8)

The herbicide combination as claimed in claim 8, wherein the active ingredient (B) is selected from 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (B1.0) and/or methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.1).

### Claim 10 (depends on 8)

The herbicide combination as claimed in claim 8, wherein said active ingredient (B) is selected from 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid (B1.12) and/or methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.13).

### Claim 11 (depends on 1)

The herbicide combination as claimed in claim 1, wherein the active ingredient (B) is methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.1).

### Claim 12 (depends on 1)

The herbicide combination as claimed in claim 1, wherein said component (C) is selected from the group consisting of trifluralin (C1.1), metribuzin (C1.2), clomazone (C1.3), pendimethalin (C1.4), metolachlor/S-metolachlor (C1.5), flumetsulam (C1.6), alachlor (C1.8), sulfentrazone (C1.10), norflurazon (C1.13), flumioxazin (C1.15), imazapyr/imazapyr-isopropylammonium (C1.16), imazamox/imazamox-ammonium (C1.17), imazaquin/imazaquin-ammonium (C1.18), carfentrazone (C1.20), imazethapyr (C1.21), dicamba (C1.22), mesotrione (C1.23), pyrasulfutole (C1.26), tembotrione (C1.27), sulcotrione (C1.29), bentazone (C2.2), thifensulfuron (C2.3), oxyfluorfen (C2.4), lactofen (C2.5), fomesafen (C2.6), flumiclorac (C2.7), acifluorfen and the sodium salt thereof (C2.8), 2,4-D (C2.10), chlorimuron/chlorimuron-ethyl (C2.11), cloransulam/cloransulam-methyl (C2.12), sethoxydim (C3.1), cycloxydim (C3.2), clethodim (C3.3), quizalofop-P and the ethyl or tefuryl ester thereof (C4.1), fenoxaprop-P and the ethyl ester thereof (C4.2), fluazifop-P and the butyl ester thereof (C4.3), haloxyfop/haloxyfop-P and the methyl or ethyl ester thereof (C4.4), propaquizafop (C4.5), and paraquat/paraquat dichloride (C5.1).

### Claim 13 (depends on 11)

The herbicide combination as claimed in claim 11, wherein said component (C) is selected from the group consisting of trifluralin (C1.1), metribuzin (C1.2), clomazone (C1.3), pendimethalin (C1.4), metolachlor/S-metolachlor (C1.5), alachlor (C1.8), sulfentrazone (C1.10), norflurazon (C1.13), flumioxazin (C1.15), imazamox/imazamox-ammonium (C1.17), carfentrazone (C1.20), dicamba (C1.22), mesotrione (C1.23), pyrasulfutole (C1.26), tembotrione (C1.27), sulcotrione (C1.29), bentazone (C2.2), thifensulfuron (C2.3), oxyfluorfen (C2.4), lactofen (C2.5), fomesafen (C2.6), flumiclorac (C2.7), acifluorfen and the sodium salt thereof (C2.8), 2,4-D (C2.10), chlorimuron/chlorimuron-ethyl (C2.11), cloransulam/cloransulam-methyl (C2.12), and clethodim (C3.3).

### Claim 14 (depends on 1)

A method of controlling weeds in soybean and/or leguminous species, comprising applying a combination as claimed in claim 1.

### Claim 15

An active ingredient composition comprising glufosinate-ammonium and, as active ingredient (B), a compound selected from:
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (B1.0),
methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.1),
ethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.2),
n-propyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.3),
i-propyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.4),
n-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.5),
2-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.6),
tert-butyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.7),
allyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.8),
2-butoxyethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.9),
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid triethylammonium salt (B1.10) and
4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid potassium salt (B1.11)
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid (B1.12)
methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.13)
ethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.14)
n-propyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.15)
i-propyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.16)
n-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.17)
2-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.18)
tert-butyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.19)
ally 16-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.20)
2-butoxyethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.21) and
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid triethylammonium salt (B1.22) and/or
6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid potassium salt (B1.23),
and as active ingredient (C), a herbicide selected from the group consisting of trifluralin (C1.1), metribuzin (C1.2), clomazone (C1.3), pendimethalin (C1.4), metolachlor/S-metolachlor (C1.5), flumetsulam (C1.6), dimethenamid/dimethenamid-p (C1.7), alachlor (C1.8), sulfentrazone (C1.10), ethalfluralin (C1.11), norflurazon (C1.13), flumioxazin (C1.15), imazapyr/imazapyr-isopropylammonium (C1.16), imazamox/imazamox-ammonium (C1.17), imazaquin/imazaquin-ammonium (C1.18), carfentrazone (C.1.20), imazethapyr/imazethapyr-ammonium (C.1.21), dicamba (C.1.22), mesotrione (C.1.23), pyrasulfutole (C.1.26), tembotrione (C.1.27), isoxaflutole (C.1.28), sulcotrione (C.1.29), bentazone (C2.2), thifensulfuron (C2.3), oxyfluorfen (C2.4), lactofen (C2.5), fomesafen (C2.6), flumiclorac (C2.7), acifluorfen and the sodium salt thereof (C2.8), 2,4-DB (C2.9), 2,4-D (C2.10) chlorimuron/chlorimuron-ethyl (C2.11), cloransulam/cloransulam-methyl (C2.12), diclosulam (2.13), oxasulfuron (C2.15), sethoxydim (C3.1), cycloxydim (C3.2), clethodim (C3.3), quizalofop-P and the ethyl or tefuryl ester thereof (C4.1), fenoxaprop-P and the ethyl ester thereof (C4.2), fluazifop-P and the butyl ester thereof (C4.3), haloxyfop/haloxyfop-P and the methyl or ethyl ester thereof (C4.4), propaquizafop (C4.5), and paraquat/paraquat dichloride (C5.1),
wherein said combination exhibits herbicide efficacy greater than expected for combinations of component (C) with mixture of components (A) and (B)
and wherein the soybean species is tolerant to the herbicides (A), (B), and (C) present in combination.

### Claim 16 (depends on 15)

The active ingredient composition as claimed in claim 15, wherein said active ingredient (B) is selected from 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (B1.0) and/or methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate (B1.1).

### Claim 17 (depends on 15)

The active ingredient composition as claimed in claim 15, wherein said active ingredient (B) is selected from 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid (B1.12) and/or methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate (B1.13).

### Claim 18 (depends on 15)

The active ingredient composition as claimed in claim 15, further comprising a safener.