# US 2019/0166833 A1 · Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods

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- Number: US 2019/0166833 A1
- Document ID: US20190166833A1
- Status: Published application
- Kind: A1
- Application number: 16/270,684
- Filed: 2019-02-08
- Published: 2019-06-06
- Earliest claimed: 2013-10-18
- Assignees: BASF Agrochemical Products B.V.
- Applicants: BASF Agrochemical Products B.V.
- Inventors: Tatjana SIKULJAK; Markus GEWEHR; Anil MENON
- Web page: https://patentgrep.com/patent/US20190166833A1

## CPC

- A01N 25/00: Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N 37/22: the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N 37/46: N-acyl derivatives
- A01N 43/22: rings with more than six members
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/88: six-membered rings with three ring hetero atoms
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/30: Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
- A01N 51/00: Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
- A01N 57/16: containing heterocyclic radicals
- A01N 57/28: 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 present invention relates to agricultural methods and the use of an insecticidal active carboxamide derivative in seed treatment and soil application methods. The insecticidal carboxamide derivative is highly suitable alone or in combination with other active agricultural ingredients for controlling animal pests such as insects and/or spider mites and/or nematodes by treating the soil/growth substrate by drenching or drip application or dipping or soil injection.

## Claims

### Claim 1

A method for controlling or combating animal pests in soil or plant propagation material comprising applying directly or indirectly to the plant or to plant propagation material by drenching the soil, by drip application onto the soil, by soil injection, by dipping or by treatment of seeds, a composition comprising an agriculturally active compound of formula (I):
or a tautomer, an enantiomer, a diastereomer or a salt thereof,
wherein the compound of formula (I) is combined with, or is applied together with, at least one other agriculturally active compound selected from the group of insecticides or fungicides consisting of epoxiconazole, triticonazole, thiophanta-methyl, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, acephate, trifumezopyrim, bifenthrin, cypermethrin, alpha-cypermethrin, tefluthrin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 (1,2,4-triazol-1-yl)pentan-2-ol, 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol or 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, and N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide and an active of Bacillus firmus.

### Claim 2 (depends on 1)

The method of claim 1, wherein in the active compound I of formula (I) is combined and/or applied together with more than one other agriculturally active compound selected from the group of insecticides and/or fungicides.

### Claim 3 (depends on 2)

The method of claim 2, wherein a third active compound is the fungicide Pyraclostrobin.

### Claim 4 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is Epoxiconazole.

### Claim 5 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is Triticonazole.

### Claim 6 (depends on 2)

The method of claim 2, wherein the at least one other agriculturally active compound is Metaxalyl.

### Claim 7 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is Thiophanate-methyl.

### Claim 8 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is selected from the group consisting of 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1(1,2,4-triazol-1-yl)pentan-2-ol, 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol, 2-[4-(4-chlorophenoxy)-2-(trifluorometh¬yl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol or 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol .

### Claim 9 (depends on 2)

The method of claim 2, wherein a third active compound is an insecticide selected from the group consisting of acephate, chlorpyrifos, fipronil, methiocarb, thiodicarb, lamba-cyhalothrin, cypermethrin, alpha-cypermethrin, bifenthrin, tefluthrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, thiacloprid, thiamethoxam, abamectin, emamectin, flubendiamide, chlorantraniliprole, cyantraniliprole, triflumezopyrim, spinosad, sulfoxaflor, Clariva®, Votovio® and actives on basis of Bacillus firmus.

### Claim 10 (depends on 2)

The method of claim 2, wherein a third active compound is a neonicotinoid insecticide selected from acetamiprid, clothianidin, imidacloprid, thiacloprid or thiamethoxam.

### Claim 11 (depends on 2)

The method of claim 2, wherein a third active compound is dinotefuran.

### Claim 12 (depends on 1)

The method of claim 1, wherein the active compound is abamectin or emamectin.

### Claim 13 (depends on 2)

The method of claim 2 wherein a third active compound is fipronil.

### Claim 14 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is an insecticide selected from the group consisting of bifenthrin, cypermethrin, alpha-cypermethrin or tefluthrin.

### Claim 15 (depends on 2)

The method of claim 2, wherein the at least one other agriculturally active compound is cyantraniliprole.

### Claim 16 (depends on 2)

The method of claim 2, wherein the at least one other agriculturally active compound is chlorantraniliprole.

### Claim 17 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is an insecticide selected from the group consisting of N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide or N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide.

### Claim 18 (depends on 2)

The method of claim 2, wherein a third active compound is spinosad.

### Claim 19 (depends on 2)

The method of claim 2, wherein a third active compound is chlorpyrifos.

### Claim 20 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is acephate.

### Claim 21 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is triflumezopyrim.

### Claim 22 (depends on 2)

The method of claim 2, wherein a third active compound is thiomethoxam.

### Claim 23 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is an active on basis of Bacillus firmus.

### Claim 24 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is Votivo® (Bacillus firmus strain 1-1582).

### Claim 25 (depends on 1)

The method of claim 1, wherein the at least one other agriculturally active compound is Clariva®.

### Claim 26 (depends on 1)

The method of claim 1, wherein the plant or the plant propagation material to be treated is grown in an artificial growth substrate.

### Claim 27 (depends on 26)

The method of claim 26, wherein the artificial growth substrate is selected from rock wool, glass wool, quartz saned, gravel, expanded clay and vermiculite.

### Claim 28 (depends on 1)

The method of claim 1, wherein the plant or plant propagation material to be treated is planted or growing in a closed system.

### Claim 29 (depends on 1)

The method of claim 1, wherein the compound of formula (I) is applied by drip irrigation.

### Claim 30 (depends on 1)

The method of claim 1, wherein the compound of formula (I) is applied with drip application systems.

### Claim 31 (depends on 1)

The method of claim 1, wherein the compound of formula (I) is applied by soil injection.

### Claim 32

A method for protection of plant propagation material comprising contacting the plant propagation material with a pesticidally effective composition comprising an agriculturally active compound of formula (I):
or a tautomer, an enantiomer, a diastereomer or a salt thereof,
wherein the compound of formula (I) is combined with, or is applied together with, at least one other agriculturally active compound selected from the group of insecticides or fungicides consisting of epoxiconazole, triticonazole, thiophanta-methyl, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, acephate, trifumezopyrim, bifenthrin, cypermethrin, alpha-cypermethrin, tefluthrin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 (1,2,4-triazol-1-yl)pentan-2-ol, 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol or 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, and N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, and an active of Bacillus firmus;
wherein the plant propagation material are seeds of transgenic plant.

### Claim 33 (depends on 32)

A method according to claim 32, wherein the compound(s) is applied in an amount of from 0.1 g to 100 kg per 100 kg of plant propagation material.

### Claim 34 (depends on 32)

A method according to claim 32, wherein the plant roots and shoots resulting from the treated seeds are protected.

### Claim 35 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are applied by drenching the soil.

### Claim 36 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are applied by drip irrigation.

### Claim 37 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are applied by soil injection.

### Claim 38 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are applied with drip application systems.

### Claim 39 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are used in in-furrow applications.

### Claim 40 (depends on 32)

A method according to claim 32, wherein the active compound(s) is/are used in T-Band applications.

### Claim 41

Seed treated with a composition comprising an agriculturally active compound of formula (I):
or a tautomer, an enantiomer, a diastereomer or a salt thereof,
and at least one other agriculturally active compound selected from the group of insecticides or fungicides consisting of epoxiconazole, triticonazole, thiophanta-methyl, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, acephate, trifumezopyrim, bifenthrin, cypermethrin, alpha-cypermethrin, tefluthrin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 (1,2,4-triazol-1-yl)pentan-2-ol, 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 242-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol or 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)¬phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide, and N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide and an active of Bacillus firmus, in an amount of from 0.1 g to 10 kg per 100 kg of seeds.