Use of n-arylamidine-substituted trifluoroethyl sulphoxide derivatives for controlling pests by watering, droplet application, dip application, soil injection or by treating seed

Patent metadata

Field	Value
Publication number	US-11058114-B2
Application number	US-201515301347-A
Country	US
Kind code	B2
Filing date	Mar 31, 2015
Priority date	Apr 4, 2014
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

The present invention relates to the use of compounds of the formula (I)

in which R 1 , R 2 , R 3 , n, X and Y have the meanings given in the description, for controlling animal pests, in particular insects and/or spider mites and/or nematodes, by drenching the soil, by drip application to the soil, by immersing roots, tubers or bulbs, or by soil injection or for treating seed.

First claim

The invention claimed is:

1. A method for controlling animal pests with one or more of N-arylamidine-substituted trifluoroethyl sulphoxide derivatives of formula (I)

where
n represents the number 1,
X represents fluorine, chlorine, bromine, or iodine,
Y represents (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl,
R 2 represents hydrogen, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl, and
R 1 and R 3 together with the atoms to which they are attached represent the group

where the arrow points to the remainder of the molecule,
wherein the compound of the formula (I) is its R enantiomer, with respect to the chiral sulphur atom, or is a mixture of the R enantiomer and the S enantiomer in which the proportion of the R enantiomer is at least 55% by weight, based on the enantiomer mixture,
comprising drenching soil, applying by drip application to the soil, immersing roots, tubers or bulbs in soil or an artificial growth substrate, or applying by soil injection with the derivative of formula (I) to thereby control the animal pests.

2. A method according to claim 1 , wherein
X and Y represent the following combinations X/Y: F/methyl or Cl/methyl, and
R 1 and R 3 together with the atoms to which they are attached represent the group

where the arrow points to the remainder of the molecule.

3. A method according to claim 1 , wherein
X and Y represent the following combinations X/Y: F/methyl or Cl/methyl,
R 2 represents hydrogen, methyl, ethyl, (2,2)-difluoroethyl or (2,2,2)-trifluoroethyl, and
R 1 and R 3 together with the atoms to which they are attached represent the group

where the arrow points to the remainder of the molecule.

4. A method according to claim 1 , wherein the compound of the formula (I) is its R enantiomer.

5. A method according to claim 1 , wherein the compound of the formula (I) is a mixture of the S enantiomer and the R enantiomer in which the proportion of the R enantiomer is at least 55% by weight, based on the enantiomer mixture.

6. A method according to claim 1 , where the plant treated is grown in an artificial growth substrate.

7. A method according to claim 1 , where the plant treated is planted in a closed system.

8. A method according to claim 1 , where the plants treated are selected from the group consisting of
vegetables, optionally fruiting vegetables or inflorescences, optionally bell peppers, chilies, tomatoes, aubergines, cucumbers, pumpkins, courgettes, broad beans, runner beans, dwarf beans, peas, artichokes, maize;
leafy vegetables, optionally head-forming lettuce, chicory, endives, various types of cress, rocket, lamb's lettuce, iceberg lettuce, leeks, spinach, Swiss chard;
tuber, root or stem vegetables, optionally celeriac/celery, beetroot, carrots, radishes, horseradish, beets for human consumption scorzonera, asparagus, palm shoots, bamboo shoots;
bulb vegetables, optionally onions, leek, fennel, garlic;
Brassica vegetables, optionally cauliflower, broccoli, kohlrabi, red cabbage, white cabbage, curly kale, Savoy cabbage, Brussel sprouts, Chinese cabbage;
citrus, optionally oranges, grapefruits, tangerines, lemons, limes, seville oranges, kumquats, satsumas;
pome fruit, optionally apples, pears or quinces;
stone fruit, optionally peaches, nectarines, cherries, plums, quetsch, apricots, almonds, pistachios, olives;
grapevines, hops, tea or tropical crops, in particular mangoes, papayas, figs, pineapples, dates, bananas, durians, kaki fruit, coconuts, cacao, coffee, avocados, lychees, maracujas, guavas, almonds or nuts, optionally hazelnuts, walnuts, pistachios, cashew nuts, para nuts, pecan nuts, butternuts, chestnuts, hickory nuts, macadamia nuts, peanuts;
soft fruit, optionally redcurrants, gooseberries, raspberries, blackberries, blueberries, strawberries, cranberries, including American cranberries, kiwi fruit;
cut flowers, optionally roses, carnations, gerbera , lilies, marguerites, chrysanthemums, tulips, narcissi, anemones, poppies, amaryllis, dahlias, azaleas, mauves;
bedding plants, pot plants or perennials, optionally roses, Tagetes , violas, geraniums, fuchsias, hibiscus, chrysanthemums, busy lizzies, cyclamen, African violet, sunflowers, begonias;
bushes or conifers, optionally ficus, rhododendron , firs, spruces, pines, including umbrella pines, yews, juniper, oleander;
spices, optionally aniseed, chili pepper, paprika, pepper, vanilla, majoram, thyme, cloves, juniper berries, cinnamon, tarragon, coriander, saffron, ginger;
cotton; and
soya beans.

9. A method according to claim 1 , wherein the animal pests are insects and/or spider mites and/or nematodes.

10. A method according to claim 1 , where X and Y represent one of the following combinations X/Y: F/methyl, Cl/methyl, Br/methyl, F/ethyl, Cl/ethyl, or Br/ethyl.

11. A method according to claim 1 , wherein the compound is of formula

12. A method according to claim 4 , wherein the compound is of formula

13. A method according to claim 5 , wherein the compound is of formula

14. A method according to claim 1 , comprising drenching soil with the derivative of formula (I).

15. A method according to claim 11 , comprising drenching soil with the derivative of formula

Assignees

• Bayer Cropscience Ag

Inventors

• Alig Bernd
• Cerezo-Galvez Silvia
• Fischer Reiner
• Köhler Adeline
• Hahn Julia Johanna
• Lösel Peter
• Malsam Olga

Classifications

• A01N37/52 Primary

  containing [IMAGE cpc-sch-A01N-0939.gif] groups, e.g. carboxylic acid amidines · CPC title

• A01N41/10 Primary

  Sulfones; Sulfoxides · CPC title

• A01N43/36

  five-membered rings · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title