RU2809600C2 - Method of combating pests of potato plants - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: method of controlling invertebrate pests of potato plants, plant propagation material from attack or infection by invertebrate pests includes the stage of contacting the plant, its parts, propagation material, plant locus, pests, their food resources, distribution or propagation sites with a pesticide effective amount compounds of formula IR-1

or a salt thereof, or a composition containing a compound of formula IR-1 or a salt thereof, and one or more other admixed components of the mixture selected from pesticide active compounds, in weight ratios of from 10,000:1 to 1:10,000.

EFFECT: proposed method of controlling invertebrate pests of potato plants has a wide spectrum of action and provides effective protection against re-infection.

18 cl, 6 tbl, 2 ex

Description

The invention relates to a method for controlling invertebrate pests of sugar cane, citrus, rapeseed, and potato plants, includes the stage of contacting the plant, its parts, material for its propagation, pests, their food resources, places of distribution or places of reproduction with one or more compounds formula I

or its tautomers, enantiomers, diastereomers or salts.

The compound of formula I is very useful for methods of controlling and/or suppressing invertebrate pests.

In addition, it has been found that mixtures of the compound of formula (I) with other agriculturally active ingredients, such as insecticides, fungicides or nematicides, are particularly suitable for methods of controlling and/or suppressing invertebrate pests.

The compound of formula (I) is present in two enantiomeric forms I-R-1 and I-S-1, as shown below.

The compound of formula (I) is present in mesoionic forms. These forms can be expressed in different isoelectronic formulas, each having formal positive and negative charges on different atoms (as shown below). The present invention covers all representative isoelectronic structures of the compound of formula I.

The compounds of formula I-R-1 and I-S-1 are also present in mesoionic forms similar to the compound of formula I as shown above.

The invention relates to a method in which the compound of formula (I) itself and its stereoisomers, salts, enantiomers or N-oxides, especially its enantiomers, and mixtures thereof are used.

The term "non-racemic compound (I)" refers to a compound of formula (I) wherein its R- and S-enantiomers are not present in equal amounts.

The term "racemic compound of formula (I)" refers to a compound of formula (I) wherein its R- and S-enantiomers are present in equal amounts.

The term "enantiomeric excess" indicates the excess of an enantiomer in a mixture of enantiomers, and is calculated using the following formula:

ee: enantiomeric excess

m ₁ : fraction of enantiomer 1

m ₂ : fraction of enantiomer 2

As used herein and unless otherwise indicated, the term "enantiomer" means each individual optically active form of a compound of the invention.

As used herein, the term “in enantiomeric excess” refers to a mixture of enantiomers where the enantiomer to which the term “enantiomeric excess” applies is present in enantiomeric excess over the other enantiomer, preferably in an amount of at least 60%, preferably at least 80%, more preferably at least 95%, most preferably at least 98% of the mixture of enantiomers. For example, the term "compound of formula I with an enantiomeric excess of compound I-R-1" refers to a compound of formula I wherein compound I-R-1 is present in an amount of enantiomeric excess over compound I-S-1, preferably in an amount of at least 60%, preferably by at least 80%, more preferably at least 95%, most preferably at least 98%.

Potato is a tuber crop grown from the perennial plant Solanum tuberosum. Potato tubers are specialized stems of the potato plant that form just below the surface of the soil. It is grown in more than 125 countries and consumed almost daily by more than a billion people. Hundreds of millions of people in developing countries depend on potatoes for their survival. Potatoes are the fourth most consumed food crop in the world after rice, wheat and corn. However, the potato crop is susceptible to attack by invertebrate pests such as thrips, leafhoppers, aphids, tuberous moths, etc. Due to different conditions, the yield and quality of potatoes can be affected by various pests, causing economic losses.

Many citrus species are cultivated throughout the world. Of these species, sweet oranges (C. sinensis) and tangerines (C. reticulata) and, to a more limited extent, grapefruits (C. paradise), lemons (C. limon) and limes (C. aurantifolia) are widely grown throughout the world. hybrids of tangelo (mandarin X grapefruit) and tangor (mandarin X sweet orange) (Rajput and Haribabu, 1993). Like most fruits, citrus fruits are a low-calorie food, a good source of carbohydrates and fiber, low in sodium and fat, and an excellent source of vitamin C. Citrus phytochemicals have potentially beneficial properties, such as antioxidant, anticancer, and cholesterol-lowering properties (Tian et al., 2001). The fruit crops are widely grown and sold as fresh fruit. However, citrus plants are susceptible to attack by arthropod pests such as leaf miners, aphids, psyllids, flies, weevils, etc., which cause damage to the crop, resulting in large economic losses.

The rapeseed crop Brassica napus is a winter or spring annual crop of the Brassica family. It is also known as rapeseed and oilseed rape. Canola is a genetic variation of canola developed through traditional breeding by Canadian plant breeders. Rapeseed refers to mustard, cabbage, broccoli, cauliflower and turnips. Rapeseed is grown primarily for its oil. Canola is also useful as a cover crop and annual forage crop. It provides good ground cover in winter to prevent soil erosion, produces large amounts of biomass, suppresses weed growth and can improve tillage with its root system. Rapeseed is produced throughout the world, particularly in China, Canada, Europe and India. Rapeseed oil is very important in vegetable oils due to its high oil content, about 40%. Oilseed rape is in third place with 15% of world production, indicating the high value of the seeds as a source of oil and animal feed. The increase in global vegetable oil production is largely dependent on increased production of palm oil, oilseed rape and soybeans (source: FAO). Rapeseed is susceptible to attack by a number of insect pests, the most important of which are flea beetles, Phyllotreta sp and Psylloides sp, rapeseed flower beetle, Meligethes sp, cabbage flea beetle, seed beetles, Ceutorhynchus sp and Bertha worm, Mamestra sp. To ensure a healthy harvest, it is very important to protect crops from harmful damage in the early stages, such as cotyledons and true leaves. Seed treatments have been used to control major oilseed rape pests such as flea beetles, cabbage stem flea beetles, potato aphids, etc. The damage caused by rapeseed flower beetles is during the flowering phase of crops, and the most vulnerable stage is green-yellow beetles. Because of the widespread pyrethroid resistance of these flea beetles and the importance of honey bees as pollinators, there is a continuing need for effective, bee-safe products to control these pests.

Sugarcane is another important crop with potential for sugar, ethanol, biofuel and feed production. Global sugar demand is the main driver of sugarcane agriculture, with sugarcane accounting for 80% of all sugar produced. The stem is an integral part of the sugarcane plant and after harvesting it is crushed and crushed by rollers to extract the sugar. Sugarcane is currently grown in different regions of the world. Major sugarcane growing countries include Brazil, India, China, Thailand, USA and Mexico. Sugarcane can be attacked by many pests, examples of such pests are termites, Odontotermes sp, shoot moth, Chilo sp, Diatraea sp, weevils, Sphenophorus sp, rhizome borer, Migdolus sp, pennies, Mahanarva sp. In Brazil, burning drill flour after harvesting sugar cane is prohibited due to environmental concerns. Consequently, the pennies, Mahanarva sp, have now become an important pest of sugarcane in Brazil. The larvae feed on roots and directly affect photosynthesis and other metabolic processes of sugarcane plants, thereby affecting the quality and quantity of the crop. There are currently several options available to control this pest, but there is an ongoing need to find an effective product to control sugarcane pests.

Although many insecticides are known, pests pose a significant threat to sugarcane, citrus, rapeseed and potato crops, and thus there is a need to find alternative insecticides capable of controlling pests of sugarcane, citrus, rapeseed and potato plants. A more effective insecticide is preferred.

The mesoionic compound of formula I exhibiting overall pesticidal activity has been previously described. WO 2014167084 describes mesoionic pyridinium compounds, their preparation and their use as pest control agents.

However, their surprisingly excellent applicability in sugarcane, citrus, rapeseed and potato plants/crops, as well as their unusual activity against pests of sugarcane, citrus, rapeseed or potato crops, especially in combination with other agricultural active ingredients, have not been previously described.

The compound of formula I according to the invention can be prepared analogously to the methods described in WO 2014/167084. The preparation of the compounds of formula (I) above may result in their being obtained in the form of isomeric mixtures. If desired, they can be separated by the usual methods for this purpose, such as crystallization or chromatography, as well as on an optically active adsorbate, to obtain pure isomers.

Agronomically acceptable salts of compound I can be prepared in the usual manner, for example by reaction with an acid of the anion in question.

Compounds of formula (I) can be prepared analogously to the methods described by Holyoke et al. in WO 2009/099929 (Scheme 1) from suitably substituted compounds (III).

Scheme 1

Compounds (III) can be prepared by methods described, for example, by Brian R. Dixon et al in US Pat. No. 6,353,006, for example, 2-chloroethanamines like compound (V), and similar methods with suitably substituted reagents.

Scheme 2

The 2-chloroethanamine compounds (V) are in turn available, for example, by reduction of sulfinyl imines, as illustrated in Denolf, Bram et al, Journal of Organic Chemistry, 72(9), 3211-3217; 2007.

Scheme 3

Compounds (VII) are prepared from α-halogen ketones, which are well known to those skilled in the art.

A compound of formula I with enantiomeric excess/enantiomeric purity I-R-1 can be prepared by a process comprising at least the following steps:

(A) reacting a compound of formula III,

Where

W is halogen, O-n-toluenesulfonyl, O-methanesulfonyl, or O-trifluoromethanesulfonyl;

with M ² OR ^AC , where M ² is selected from lithium, sodium, potassium, aluminum, barium, cesium, calcium and magnesium; R ^AC represents C(=O)-C ₁ -C ₄ -alkyl;

to obtain a compound of formula IV,

where Het and R ^AC have the meanings specified herein;

(B) hydrolyzing a compound of formula IV, as defined herein, in the presence of an acid or base to obtain a compound of formula V,

where Het has the meaning specified for the compound of formula IV;

(B) reacting a compound of formula V with X ² SO ₂ NH ₂ where X ² is a halogen,

to obtain the compound of formula VI

(C) hydrogenation of a compound of formula VI,

in the presence of a hydrogenation catalyst MXLn,

Where

M is a transition metal from group VIII - group XII of the periodic table;

X represents an anion;

Ln is Ln1 or Ln2,

Where

Ln1 is a chiral ligand of the formula Ln1

Where

C* represents an asymmetric carbon atom of the S or R configuration;

R ¹⁰ represents OH or NH-SO ₂ -R ¹¹ ; Where

R ¹¹ is aryl, unsubstituted or substituted with halogen, C ₁ -C ₁₀ -alkyl, C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyl, SO ₃ H, or SO ₃ Na,

or

C ₁ -C ₁₀ -perfluoroalkyl, or R ¹³ R ¹⁴ N where R ¹³ and R ¹⁴ independently represent C ₁ -C ₁₀ -alkyl, unsubstituted or substituted with C ₆ -C ₁₀ -aryl, or R ¹³ and R ¹⁴ represent C ₆ -C ₁₀ -cycloalkyl;

R ¹² independently represents aryl or a C ₆ -C ₁₀ -cycloalkyl ring, where the ring is unsubstituted or independently substituted with halogen, C ₁ -C ₁₀ -alkyl, C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyl , SO ₃ H, or SO ₃ Na, or both R ¹² are attached to each other to form a 3-6 membered carbocyclic ring or a 5-10 membered partially unsaturated carbocyclic ring;

Ln2 is a chiral phosphorus ligand;

and the hydrogen source is selected from a) a mixture of N(R) ₃ , where R is H or C ₁ -C ₆ -alkyl, and HCOOH, b) HCOONa, and c) a mixture of isopropyl alcohol, and t-BuOK or t-BuONa or t-BuOLi;

to obtain a compound of formula VII

Where

C* represents an asymmetric carbon atom of the S or R configuration;

(D) reacting a compound of formula VII,

Where

C* represents an asymmetric carbon atom of the S or R configuration;

with CH ₃ NCS;

in the presence of a base,

to obtain a compound of formula VIII,

(E) reacting a compound of formula VIII as described herein with a compound of formula IX

Where

LG is a leaving group selected from halogen, OR ^u or SR ^u ; Where

R ^u represents halogen, C ₁ -C ₆ -alkyl or aryl, which is unsubstituted or substituted with halogen;

to obtain the compound of Formula I in enantiomeric excess as described herein.

However, although it is known that mesoionic compounds and their combined use with other insecticides have demonstrated activity against certain crop-damaging insect pests, none of these documents disclose the acceptable effectiveness of a compound of formula I or a compound of formula (I) with an enantiomeric excess of the compound I-R- 1 or compound IR-1, and some of their selected mixtures with other pesticide active compounds against typical pests of sugar cane, citrus, rapeseed and potatoes; preferably in relation to genetically modified plants, preferably by impregnation or foliar application.

The present invention further relates to and includes the following embodiments:

- a method for suppressing or controlling invertebrate pests of sugarcane, citrus, rapeseed and potato plants, infestation, or infection by invertebrate pests, where the method includes contacting said pest or its food resources, distribution site or breeding site with a compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1 as defined above and below herein, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess compounds of formula I-R-1 or compound I-R-1;

- a method for suppressing or controlling invertebrate pests of sugarcane, citrus, rapeseed and potato plants, infestation, or infection by invertebrate pests, where the method includes treating or contacting the plant, plant propagation material and growing plants of sugarcane, citrus, rapeseed and potato , or soil, material, surface, space, area or water where plants, plant propagation material are stored or the plant grows (plant locus), with a pesticidal effective amount of a compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compounds I-R-1, as defined above and below herein, or a composition containing at least one compound of formula (I) or compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compound I-R-1 ;

- a method of protecting a sugar cane, citrus, rapeseed and potato plant from invertebrate pests, which includes contacting the sugar cane, citrus, rapeseed and potato plant, invertebrate pests, or their food resources, distribution site or breeding site with a pesticide effective amount of a compound of the formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 as defined above, or a composition containing at least one compound of formula (I), or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compound I-R-1 as defined above and below herein;

- a method for protecting sugar cane, citrus, rapeseed and potato plants, their plant propagation material and/or growing sugar cane, citrus, rapeseed and potato plants from attack or infestation by invertebrate pests, which includes treating or contacting the plant, propagation material plants and growing sugarcane, citrus, rapeseed and potato plants, or the soil, material, surface, space, area or water where the plant, plant propagation material is stored or the plant grows (plant locus), with a pesticidal effective amount of a compound of formula (I ) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1 as defined above and below herein, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compound I-R-1;

- Use of a compound of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1, or a compound I-R-1, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric an excess of a compound of formula I-R-1 or compound I-R-1, for protecting a growing sugarcane, citrus, rapeseed, or potato plant, plant propagation material from attack or infestation by invertebrate pests of sugarcane, citrus, rapeseed, and potato plants;

- The use of compounds of formula (I), or non-racemic compounds of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compound I-R-1, for controlling invertebrate pests of sugarcane, citrus, rapeseed or potato plants.

In addition, the present invention relates to and includes the following embodiments:

- a method of suppressing or controlling invertebrate pests of potato plants, infestation, or infection by invertebrate pests, where the method includes contacting said pest or its food resources, distribution site or breeding site with a compound of formula (I) or a compound of formula (I) with an enantiomeric an excess of a compound of formula I-R-1 or a compound I-R-1 as defined above and below herein, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1;

- a method of suppressing or controlling invertebrate pests of potato plants, infestation, or infection by invertebrate pests, where the method includes treating or contacting plants, plant propagation material and growing potato plants, or soil, material, surface, space, area or water, wherein the plants, plant propagation material are stored or the plant grows (plant locus), with a pesticidal effective amount of a compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1 as defined above and below herein, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1;

- a method of protecting potatoes from invertebrate pests, which includes contacting invertebrate pests of potato plants, or their food resources, distribution site or breeding site with a pesticidal effective amount of a compound of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R -1 as above, or a composition containing at least one compound of formula (I) or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R -1 as specified above and below herein;

- a method of protecting potato plants, their plant propagation material and/or growing potato plants from attack or infestation by invertebrate pests, which includes treating or bringing into contact the plants, plant propagation material and growing potato plants, or soil, material, surface, space , area or water where plants, plant propagation material are stored or the plant grows (plant locus), with a pesticidal effective amount of a compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1, as defined above and below herein, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1;

- The use of compounds of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1, or a compound I-R-1, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric an excess of a compound of formula I-R-1 or compound I-R-1, to protect a growing potato plant, plant propagation material from attack or infestation by invertebrate pests of potato plants;

- The use of compounds of formula (I), or non-racemic compounds of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1, or a composition containing at least one compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or compound I-R-1, for controlling invertebrate pests of potato plants,

In one embodiment of the invention, the compound of formula I is non-racemic;

In another embodiment of the invention, the compound of formula I is compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 55% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 60% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 65% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 70% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 75% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 80% of compound I-R-1;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 85% of compound I-R-1;

In a preferred embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 90% of compound I-R-1;

In another preferred embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 95% of compound I-R-1;

In another preferred embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 98% of compound I-R-1;

In another preferred embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of at least 99% of compound I-R-1;

In one embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥55% to ≤100% and compound I-S-1 is present in an amount from ≤45% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥60% to ≤100% and compound I-S-1 is present in an amount from ≤40% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥65% to ≤100% and compound I-S-1 is present in an amount from ≤35% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥70% to ≤100% and compound I-S-1 is present in an amount from ≤30% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥75% to ≤100% and compound I-S-1 is present in an amount from ≤25% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥80% to ≤100% and compound I-S-1 is present in an amount from ≤20% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥85% to ≤100% and compound I-S-1 is present in an amount from ≤15% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥90% to ≤100% and compound I-S-1 is present in an amount from ≤10% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥95% to ≤100% and compound I-S-1 is present in an amount from ≤5% to ≥0%;

In another embodiment of the invention, compounds of formula (I) refer to a compound of formula (I) with an enantiomeric excess of compound I-R-1, wherein compound I-R-1 is present in an amount of from ≥98% to ≤100%, preferably ≥99% to ≤100 %, and compound I-S-1 is present in an amount of ≤2% to ≥0%, preferably ≤1% to ≥0%;

The terms "compound of formula I", "compound(s) I", "compound of formula I-R-1", or "compound of formula I with an enantiomeric excess of compound I-R-1", and the terms "compound(s) for methods in accordance with (this ) invention", "compound(s) in accordance with the present invention", or wherein all compounds used in the methods and applications in accordance with the present invention include the compounds described herein, as well as their known stereoisomers, salts, tautomers or its N-oxides (including a polymorphic crystalline form, co-crystal or solvate of a compound or a stereoisomer, salt, tautomer or N-oxide thereof).

The compounds of the invention may be amorphous or may exist in different crystalline states (polymorphs), which may have different macroscopic properties, such as stability, or exhibit different biological properties, such as activity. The present invention relates to amorphous and crystalline compounds in accordance with the invention, to mixtures of different crystalline states of the corresponding compounds in accordance with the invention, as well as their amorphous or crystalline salts.

The compounds of the invention may be amorphous or may exist in one or more different crystalline states (polymorphs), which may have different macroscopic properties, such as stability, or exhibit different biological properties, such as activity. The present invention relates to amorphous and crystalline compounds in accordance with the invention, mixtures in different crystalline states of the corresponding compounds in accordance with the invention, as well as their amorphous or crystalline salts.

The salts of the compounds according to the invention are preferably agriculturally and/or veterinarily acceptable salts, preferably agriculturally acceptable salts. They can be formed in the usual manner, for example by reacting the compound with an acid of the anion in question, if the compounds according to the invention have basic functionality, or by reacting the acidic compounds according to the invention with a suitable base.

Agriculturally useful salts of the compounds according to the invention include in particular the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the pesticidal action of the compounds according to the invention.

Suitable cations are in particular ions of alkali metals, preferably Li, Na and K, alkaline earth metals, preferably Ca, Mg and Ba, and transition metals, preferably Mn, Cu, Zn and Fe, as well as ammonium (NH ₄ ⁺ ) and substituted ammonium, in which from one to four H atoms are replaced by C ₁ -C ₄ -alkyl, C ₁ -C ₄ -hydroxyalkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, phenyl or benzyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethyl ammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethyl mmonium, in addition , phosphonium ions, sulfonium ions, preferably tri(C ₁ -C ₄ -alkyl)sulfonium, and sulfoxonium ions, preferably tri(C ₁ -C ₄ -alkyl)sulfonium.

The anions of suitable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and C ₁ -C ₄ -alkanoic acid anions, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds according to the invention with an acid of the appropriate anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term "N-oxide" includes any compound of the present invention that contains at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.

The term "genetically modified plant" refers to a plant in which the genetic material has been altered in a way that does not occur naturally through mating and/or natural recombination.

Additional preferred embodiments of the present invention are described below.

In one preferred embodiment of the invention, the plants/crops are selected from the family Roaceae, for example sugarcane, the family Rutaceae, for example citrus, the family Brassicaceae, for example rapeseed, and the family Solanaceae, for example potatoes;

In another preferred embodiment of the invention, the plants/crops are selected from sugar cane, citrus, rapeseed and potatoes;

In another preferred embodiment of the invention, the plants/crops are selected from citrus, rapeseed and potato;

In another preferred embodiment of the invention, the plants/crops are selected from sugar cane, rapeseed and potatoes;

In another preferred embodiment of the invention, the plants/crops are selected from sugar cane, citrus fruits and potatoes;

In another preferred embodiment of the invention, the plants/crops are selected from sugar cane, citrus and rapeseed;

In another preferred embodiment of the invention, the plants/crops are sugar cane;

In another preferred embodiment of the invention, the plants/crops are citrus; preferably plants selected from oranges, tangerines, lemons, grapefruit, pomelo and lime;

In another preferred embodiment of the invention, the plants/crops are rapeseed;

In another preferred embodiment of the invention, the plants/crops are potatoes;

In the context of the present invention, invertebrate pests are animal pests that are found in sugar cane, citrus fruits, rapeseed and potatoes. Invertebrate pests include insects, mites and nematodes, especially insects. Invertebrate pests known in sugarcane, citrus, canola and potato plants include, but are not limited to:

Abacarus sacchari, Acigona steniellus, Aleurolobus barodensis, Cavelerius excavatus, Ceratovacuna lanigera, Chilo sp, such as Chilo auricillus, Chilo infescatellus, Chilo partellus, Chilo saccharifagus indicus, Chilo terrenellus, Chilo tumidicostalis, Conoderus sp, Coptotermes heimi, Diaprepes abbreviatus, Dia traea sp , such as Diatraea saccharalis, Elasmopalpus sp, such as Elasmopalpus lignosellus, Eldana saccharina, Emmalocera depresella, Fulmekiola serrata, Haplothrips sp, Hoplolaimus indicus, Leptodictya tabida, Mahanarva sp, such as Mahanarva fimbriolata, Melanaphis sacchari, Melanaspis glomerata, Melanasp is glomerate, Melanotus Communis, Meloidogyne Javanica, Metamasius Hemipterous, Migdolus SP, such as Migdolus Fryanus, Miscrotermes Obesi, Myasmia Trapezalis, Odontotermes SP, such as Odontomes Assmuthi, O Wallon ENSIS, O. Obesus, Oligonychus Stickneyl, Schizotetranychus SP, Perkinsiella Saccharicida, Perkinsiella Vastatrix, P vitiensis, Pipersia sacchari, Polyocha depressella, Pratylenchus spp, Pyrilla purpusilla, Rhabdoscelus obscurus, Rotylenchulus reniformis, Saccharosydne saccharivora, Schistocerca americana, Scirpophaga excerptalis, Sesamia grisescens, Sesamia inferens, Sipha flava, Sphenophorus sp, such like Sphenophorus levis, Tomarus subtropicus, Trinervitermes bifomis, Tryporyza nivella, Agrotis ipsilon, Athalia rosae, Autographia californica, Brevicoryne brassicae, Ceutorhynchus sp, such as Ceutorhynchus assimilis, Ceutorhynchus napi, Ceutorhynchus obstrictus, Ceutorhynchus pallidactylus, Ceutorhynchus picitarsis, Ceutorhynchus quadridens, Con Tarinia nasturtii, Dasineura brassicae, Delia brassicae, Dicestra trifoli, Entomoscelis americana, Lygus spp., Mamestra sp, such as Mamestra configurata, Meligethes sp, such as Meligethes aeneus, Meligethes viridescens, Phyllotreta spp, Phyllotreta cruciferae, Phyllotreta memorum, Phyllotreta undulata, Phyllotreta diademata,, Phyllotreta striolata, Ph ytomyza rufipes , Pieris sp., Plutella xyloStella, Psylliodes sp, such as Psylliodes chrysocephala, Psylliodes punctulata, Vanessa cardui, Aleurothrixus floccosus, Amorbia cuneana, Anacamptodes fragilaria, Aonidiella aurantii, Aonidiella citrina, Aphis sp, such as Aphis fabae, Aphis frangulae, Aphis nasturt ii ,Aphis gossypii, Aphis spiraecola, Archips argyrospilam, Argyrotaenia (=citrana) franciscana, Brevipalpus sp, such as Brevipalpus lewisi, Caliothrips fasciatus, Cantareus asperses, Ceroplastes floridensis, Chrysomphalus aonidum, Coccus hesperidum, Coccus pseudomagnoliarum, Dialeurodes citri, Diaphorina citri, Diaprepes abbreviates, Egira (Xylomyges) curialis, Empoasca sp, such as Empoasca fabae, Empoasca devastans, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eriophyes sheldoni, Eutetranychus banksi, Forficula auricularia, Frankliniella spp, Heliothrips haemorrhoidalis, Homalodisca vitripennis, Icerya purchase, Lepidosaphes beckii, Lepidosaphes gloveri, Leptoglossus zonatus, Marmara gulosa, Melanoplus devastator, Microcentrum retinerve, Naupactus (Asynonychus) godmani, Oedalenotus enigma, Orgyia vetusta, Ostrinia nubilalis, Panonychus sp, such as Panonychus citri, Papilio zelicaon, Parabemisia myricae, Parlatoria pergandii, Phyllocnistis citrella, Phyllocoptruta oleivora, Pinnaspisas pidistrae, Planococcus citri, Platynota stultana, Polyphagotarsonemus latus, Pseudococcus spp, Pyroderces rileyi, Saissetia neglecta, Saissetia oleae, Scirtothrips sp, Scudderia furcate, Siphoninus phillyreae, Spodoptera exigua, Tetranychus sp, such as Tetranychus kanzawai, Tetranychus urticae, Toxoptera aurantii, Trichoplusia ni, Unaspis citri, COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanicola, Agriotes sp such as Agriotes lineatus, Agriotes obscurus, Amphimallon solstitialis, Amrasca devastans, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera sp such Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Epitrix spp., Heliothis zea, Henosepilachna vigintioctomaculata, Heterodera spp., Holotrichia oblita, Leptinotarsa sp, such as Leptinotarsa decemlineata, Limonius sp, such as Limonius canus, Limonius californicus , Ctenicera pruinina, Liriomyza spp, Macrosiphum sp, such as Macrosiphum euphorbiae, Macrosteles fascifrons, Meloidogyne hapla, Meloidogyne chitwoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus ornatus, Pemphigus sp., Peridroma saucia, Phthorimaea spp, Phthorimaea operculella Pratylenchus penetrans, P. neglectus, Paratrichodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Rhopalosiphum ruflabdominalis, Russelliana solanicola Tuthill, Smynthurodes betae, Spodoptera eridania, Spodoptera frugiperda, Spodoptera litura, Ceratitis capitata.

Preferred pests are: Abacarus sacchari, Acigona steniellus, Aleurolobus barodensis, Cavelerius excavatus, Ceratovacuna lanigera, Chilo sp such as Chilo auricillus, Chilo infescatellus, Chilo saccharifagus indicus, Chilo terrenellus, Chilo tumidicostalis, Conoderus sp, Coptotermes heimi, Diaprepes abbreviatus Eldana saccharina, Emmalocera depresella, Fulmekiola serrata, Haplothrips sp, Hoplolaimus indicus, Leptodictya tabida, Mahanarva sp, such as Mahanarva fimbriolata, Melanaphis sacchari, Melanaspis glomerata, Melanaspis glomerate, Melanotus communis, Meloidogyne javanica, Metamasius hemipterous, Migdolus sp, such as Migdolus fryanus , Miscrotermes obesi, Myasmia trapezalis, Odontotermes sp, such as Odontotermes assmuthi, O wallonensis, O. obesus, Oligonychus stickneyl, Schizotetranychus sp, Perkinsiella saccharicida, Perkinsiella vastatrix, P. vitiensis, Pipersia sacchari, Polyocha depressella, Pratylenchus spp, Pyrilla purpusilla , Rhabdoscelus obscurus, Rotylenchulus reniformis, Saccharosydne saccharivora, Schistocerca americana, Scirpophaga excerptalis, Sesamia grisescens, Sipha flava, Sphenophorus sp, such as Sphenophorus levis, Tomarus subtropicus, Trinervitermes bifomis, Tryporyza nivella, Agrotis ipsilon, Athalia rosae , Autographia californica, Brevicoryne brassicae, Ceutorhynchus sp, such as Ceutorhynchus assimilis, Ceutorhynchus napi, Ceutorhynchus obstrictus, Ceutorhynchus pallidactylus, Ceutorhynchus picitarsis, Ceutorhynchus quadridens, Contarinia nasturtii, Dasineura brassicae, Delia brassicae, Dicestra trifoli, Entomoscelis americana, Lygus spp. , Mamestra sp, such as Mamestra configurata, Meligethes sp, such as Meligethes aeneus, Meligethes viridescens, Phyllotreta spp, Phyllotreta cruciferae, Phyllotreta memorum, Phyllotreta undulata, Phyllotreta diademata,, Phyllotreta striolata, Phytomyza rufipes, Pieris sp., Plutella xyloStella, Psylliodes sp, such as Psylliodes chrysocephala, Psylliodes punctulata , Vanessa cardui, Aleurothrixus floccosus, Amorbia cuneana, Anacamptodes fragilaria, Aonidiella aurantii, Aonidiella citrina, Aphis sp, such as Aphis fabae, Aphis frangulae, Aphis nasturtii, Aphis gossypii, Aphis spiraecola, Archips argyrospilam, Argyrotaenia (=citrana) franciscan a, Brevipalpus sp such as Brevipalpus lewisi, Caliothrips fasciatus, Cantareus asperses, Ceroplastes floridensis, Chrysomphalus aonidum, Coccus hesperidum, Coccus pseudomagnoliarum, Dialeurodes citri, Diaphorina citri, Diaprepes abbreviates, Egira (Xylomyges) curialis, Empoasca sp such as Empoasca fabae, Em poasca devastans , Eotetranychus sexmaculatus, Eotetranychus yumensis, Eriophyes sheldoni, Eutetranychus banksi, Forficula auricularia, Frankliniella spp, Heliothrips haemorrhoidalis, Homalodisca vitripennis, Icerya purchase, Lepidosaphes beckii, Lepidosaphes gloveri, Leptoglossus zonatus, Marmara gulosa, Melanoplus devast ator, Microcentrum retinerve, Naupactus (Asynonychus) godmani, Oedaleonotus enigma, Orgyia vetusta, Ostrinia nubilalis, Panonychus sp, such as Panonychus citri, Papilio zelicaon, Parabemisia myricae, Parlatoria pergandii, Phyllocnistis citrella, Phyllocoptruta oleivora, Pinnaspisas pidistrae, Planococcus citri, Platynota stultana, Polyphagotars onemus latus, Pyroderces rileyi, Saissetia neglecta, Saissetia oleae, Scirtothrips sp, Scudderia furcate, Siphoninus phillyreae, Spodoptera exigua, Tetranychus sp, such as Tetranychus kanzawai, Tetranychus urticae, Toxoptera aurantii, Trichoplusia ni, Unaspis citri, COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanic ola, Agriotes sp. , such as Agriotes lineatus, Agriotes obscurus, Amphimallon solstitialis, Amrasca devastans, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera sp, such as Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Epitrix spp., He liothis zea , Henosepilachna vigintioctomaculata, Heterodera spp., Holotrichia oblita, Leptinotarsa sp, such as Leptinotarsa decemlineata, Limonius sp, such as Limonius canus, Limonius californicus, Ctenicera pruinina, Liriomyza spp, Macrosiphum sp, such as Macrosiphum euphorbiae, Meloidogyne hapla, Meloidogyne chi twoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus ornatus, Pemphigus sp., Peridroma saucia, Phthorimaea spp, Phthorimaea operculella, Pratylenchus penetrans, P. neglectus, Paratricodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Russelliana solanicola Tuthill, Smynthurodes be tae Spodoptera eridania, Spodoptera litura, and Ceratitis capitata.

In a more preferred embodiment of the invention, the invertebrate pests are selected from Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp, Mahanarva sp, Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp., Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora and Ceratitis capitata, Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Macrosiphum sp, Aphis sp, and Phthorimaea sp.

Also in a more preferred embodiment of the invention, the invertebrate pests are selected from Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp, Mahanarva sp, Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp., Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora and Ceratitis capitata, Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Aphis sp, and Phthorimaea sp.

In a preferred embodiment of the invention, the pests are selected from Mahanarva fimbriolata, Meligethes aeneus, Phyllotreta striolata, Diaphorina citri, and Leptinotarsa decemlineata;

In one preferred embodiment of the invention, the plant is sugar cane, and the invertebrate pests are selected from Abacarus sacchari, Acigona steniellus, Aleurolobus barodensis, Cavelerius excavatus, Ceratovacuna lanigera, Chilo auricillus, Chilo infescatellus, Chilo partellus, Chilo saccharifagus indicus, Chilo terrenellus, Chilo tumidicostalis, Conoderus sp, Coptotermes heimi, Diaprepes abbreviatus, Diatraea saccharalis, Elasmopalpus lignosellus, Eldana saccharina, Emmalocera depresella, Fulmekiola serrata, Haplothrips sp, Hoplolaimus indicus, Leptodictya tabida, Mahanarva fimbriolata, Melanaphis sacchari, Melanaspis glomerata, Melanaspis glomerate, Melanotus communis , Meloidogyne javanica, Metamasius hemipterous, Migdolus fryanus, Miscrotermes obesi, Myasmia trapezalis, Odontotermes assmuthi, O wallonensis, O. obesus, Oligonychus stickneyl, Schizotetranychus sp, Perkinsiella saccharicida, Perkinsiella vastatrix, P. vitiensis, Pipersia sacchari, Polyocha de pressella, Pratylenchus spp. , Pyrilla purpusilla, Rhabdoscelus obscurus, Rotylenchulus reniformis, Saccharosydne saccharivora, Schistocerca americana, Scirpophaga excerptalis, Sesamia grisescens, Sesamia inferens, Sipha flava, Sphenophorus levis, Tomarus subtropicus, Trinervitermes bifomis, and Tryporyza nivella; preferably the pest is Mahanarva fimbriolata;

In another preferred embodiment of the invention, the plant is sugar cane and the invertebrate pests are selected from Abacarus sacchari, Acigona steniellus, Aleurolobus barodensis, Cavelerius excavatus, Ceratovacuna lanigera, Chilo auricillus, Chilo infescatellus, Chilo saccharifagus indicus, Chilo terrenellus, Chilo tumidicostalis, Conoderus sp, Coptotermes heimi, Diaprepes abbreviatus, Eldana saccharina, Emmalocera depresella, Fulmekiola serrata, Haplothrips sp, Hoplolaimus indicus, Leptodictya tabida, Mahanarva fimbriolata, Melanaphis sacchari, Melanaspis glomerata, Melanaspis glomerate, Melanotus communis, Meloidogyne javanica, Metamasius hemipterous, Migdolus fryanus, Miscrotermes obesi, Myasmia trapezalis, Odontotermes assmuthi, O wallonensis, O. obesus, Oligonychus stickneyl, Schizotetranychus sp, Perkinsiella saccharicida, Perkinsiella vastatrix, P. vitiensis, Pipersia sacchari, Polyocha depressella, Pratylenchus spp, Pyrilla purpusilla, Rhabdoscelus obscurus , Rotylenchulus reniformis, Saccharosydne saccharivora, Schistocerca americana, Scirpophaga excerptalis, Sesamia grisescens, Sipha flava, Sphenophorus levis, Tomarus subtropicus, Trinervitermes bifomis, and Tryporyza nivella; preferably the pest is Mahanarva fimbriolata;

In a more preferred embodiment of the invention, the plant is sugarcane and the invertebrate pests are selected from Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp and Mahanarva sp.; more preferably the pest is Mahanarva fimbriolata;

In another preferred embodiment of the invention, the plant is rapeseed and the invertebrate pests are selected from Agrotis ipsilon, Athalia rosae, Autographia californica, Brevicoryne brassicae, Ceutorhynchus assimilis, Ceutorhynchus napi, Ceutorhynchus obstrictus, Ceutorhynchus pallidactylus, Ceutorhynchus picitarsis, Ceutorhynchus quadridens, Contar inia nasturtii, Dasineura brassicae, Delia brassicae, Dicestra trifoli, Entomoscelis americana, Lygus spp., Mamestra configurata, Meligethes aeneus, Meligethes viridescens, Phyllotreta cruciferae, Phyllotreta memorum, Phyllotreta undulata, Phyllotreta diademata, Phyllotreta spp, Phyllotreta striolata , Phytomyza rufipes, Pier is sp. , Plutella xylostella, Psylliodes chrysocephala, Psylliodes punctulata, and Vanessa cardui; preferably the pest is Meligethes aeneus or Phyllotreta striolata;

In a more preferred embodiment of the invention, the plant is rapeseed and the invertebrate pests are selected from Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp; more preferably the pest is Meligethes aeneus or Phyllotreta striolata;

In another preferred version of the invention, the plant is citrus fruits, and invertebrate pests are selected from Aleurothrixus Floccosus, Amorbia Cuneana, Anacamptodes Fraglaria, Auranella aurantii, Aonidiella Citrina, Aphis Gossypii, Aphis, Aphis Spiraecola, Archips Argyrospilam, Argyrotaenia (= Citrana) Franciscana, Brevipalpus Lewisi E otetranychus yumensis, Eriophyes sheldoni, Eutetranychus banksi, Forflcula auricularia, Frankliniella spp, Heliothrips haemorrhoidalis, Homalodisca vitripennis, leery a purchase, Lepidosaphes beckii, Lepidosaphes gloveri, Leptoglossus zonatus, Marmara gulosa, Melanoplus devastator, Microcentrum retinerve, Naupactus (Asynonychus) godmani, Oedaleonotus enigma, Orgyia vetusta, Ostrinia nubilalis , Panonychus citri, Papilio zelicaon, Parabemisia myricae, Parlatoria pergandii, Phyllocnistis citrella, Phyllocoptruta oleivora, Pinnaspisas pidistrae, Planococcus citri, Platynota stultana, Polyphagotarsonemus latus, Pseudococcus spp, Pyroderces rileyi, Saissetia neglecta, Saissetia oleae, Scirtothrips sp, Scudderia furcate, Siphoninus phillyreae, Spodoptera exigua, Tetranychus kanzawai, Tetranychus urticae, Tetranychus urticae, Toxoptera aurantii, Trichoplusia ni, and Unaspis citri; preferably the pest is Diaphorina citri;

In another preferred embodiment of the invention, the plant is a citrus fruit and the invertebrate pests are selected from Aleurothrixus floccosus, Amorbia cipeapa, Anacamptodes fragilaria, Aonidiella aurantii, Aonidiella citrina, Aphis gossypii, Aphis spiraecola, Archips argyrospilam, Argyrotaenia (=citrana) franciscana, Brevipalpus le wisi E otetranychus yumensis, Eriophyes sheldoni, Eutetranychus banksi, Forflcula auricularia, Frankliniella spp, Heliothrips haemorrhoidalis, Homalodisca vitripennis, leery a purchase, Lepidosaphes beckii, Lepidosaphes gloveri, Leptoglossus zonatus, Marmara gulosa, Melanoplus devastator, Microcentrum retinerve, Naupactus (Asynonychus) godmani, Oedaleonotus enigma, Orgyia vetusta, Ostrinia nubilalis , Panonychus citri, Papilio zelicaon, Parabemisia myricae, Parlatoria pergandii, Phyllocnistis citrella, Phyllocoptruta oleivora, Pinnaspisas pidistrae, Planococcus citri, Platynota stultana, Polyphagotarsonemus latus, Pyroderces rileyi, Saissetia neglecta, Saissetia oleae, Scirtothrips sp, Scudderia furcate, Siphoninus phillyreae, Spodoptera exigua, Tetranychus kanzawai, Tetranychus urticae, Tetranychus urticae, Toxoptera aurantii, Trichoplusia ni, and Unaspis citri; preferably the pest is Diaphorina citri;

In a more preferred embodiment of the invention, the plant is a citrus fruit and the invertebrate pests are selected from Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora, and Ceratitis capitata; more preferably the pest is Diaphorina citri;

In one embodiment of the invention, the plant or seed is/is a potato, and the pests are selected from COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanicola, Agriotes lineatus, Agriotes obscurus, Agrotis ipsilon, Amphimallon solstitialis, Amrasca devastans, Aphis fabae, Aphis frangulae, Aphis gossypii, Aphis nasturtii, Aphis spiraecola, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Empoasca devastans, Empoasca fabae, Epitrix spp., He liothis zea, Henosepilachna vigintioctomaculata , Heterodera spp., Holotrichia oblita, Leptinotarsa decemlineata, Limonius canus, Limonius californicus, Ctenicera pruinina, Liriomyza spp, Macrosiphum euphorbiae, Macrosteles fascifrons, Meloidogyne hapla, Meloidogyne chitwoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus or natus, Pemphigus sp. ., Peridroma saucia, Phthorimaea operculella, Phthorimaea spp, Pratylenchus penetrans, P. neglectus, Paratrichodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Rhopalosiphum rufiabdominalis, Russelliana solanicola Tuthill, Smynthurodes betae, Spodoptera eridania, Spodoptera frugi perda, and Spodoptera litura; preferably the pest is Leptinotarsa decemlineata;

In another embodiment of the invention, the plant or seed is/is a potato, and the pests are selected from COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanicola, Agriotes lineatus, Agriotes obscurus, Agrotis ipsilon, Amphimallon solstitialis, Amrasca devastans, Aphis fabae, Aphis frangulae , Aphis gossypii, Aphis nasturtii, Aphis spiraecola, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Empoasca devastans, Empoasca fabae, Epitrix spp., Heliothis ze a, Henosepilachna vigintioctomaculata, Heterodera spp., Holotrichia oblita, Leptinotarsa decemlineata, Limonius canus, Limonius californicus, Ctenicera pruinina, Liriomyza spp, Macrosiphum euphorbiae, Meloidogyne hapla, Meloidogyne chitwoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus ornatus, Pemphigus sp., Per. idroma saucia , Phthorimaea operculella, Phthorimaea spp, Pratylenchus penetrans, P. neglectus, Paratrichodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Russelliana solanicola Tuthill, Smynthurodes betae, Spodoptera eridania, and Spodoptera litura; preferably the pest is Leptinotarsa decemlineata;

In a more preferred embodiment of the invention, the plant is a potato and the invertebrate pests are selected from Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Macrosiphum sp, Aphis sp, and Phthorimaea sp; more preferably the pest is Leptinotarsa decemlineata;

Also in a more preferred embodiment of the invention, the plant is a potato, and the invertebrate pests are selected from Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Aphis sp, and Phthorimaea sp; more preferably the pest is Leptinotarsa decemlineata;

Also in a more preferred embodiment of the invention, the plant is potato, rapeseed, sugarcane, or citrus, and the invertebrate pests are selected from Phyllotreta striolata, Leptinotarsa decimlineata, Mahanarva sp., Diaphorina sp., Meligethes aeneus, and Leptinotarsa decemlineata;

The methods and applications according to the invention are the control and/or prevention of pest infestation of sugarcane, citrus, rapeseed and potato plants, and propagation material of sugarcane, citrus, rapeseed and potato plants.

In general, the pests are listed above. Preferably, the methods and uses of the present invention are used against pests that are resistant to other insecticides, for example, pyrethroid insecticides. Expected sensitivity can be measured using, for example, a strain that has not previously been exposed to insecticides.

In one embodiment of the invention, the method includes applying to plants, crops and/or plant propagation material of sugar cane, citrus, rapeseed and potatoes, a compound in accordance with the invention, where the method is to control and/or prevent pest infestation.

In another embodiment of the invention, the method includes applying compounds formula I, where the method is to control and/or prevent pest infestation.

In another embodiment of the invention, the method comprises applying to sugarcane, citrus, rapeseed and potato plants, crops and/or plant propagation material, in particular citrus plants, citrus crops and/or citrus plant propagation material, a compound of formula I, wherein the method is to control and/or prevent pest infestation.

In another embodiment of the invention, the method comprises applying to sugarcane, citrus, rapeseed and potato plants, crops and/or plant propagation material, in particular rapeseed plants, rapeseed crops and/or rapeseed plant propagation material, a compound of formula I, wherein the method is to control and/or prevent pest infestation.

In another embodiment of the invention, the method comprises applying to sugarcane, citrus, rapeseed and potato plants, crops and/or plant propagation material, in particular potato plants, potato crops and/or potato plant propagation material, a compound of formula I, wherein the method is to control and/or prevent pest infestation.

In another embodiment, the invention provides the use of the compounds of the invention for the control of pests that are resistant to one or more insecticides, preferably pyrethroids, neonicotinoids and organophosphates, and more preferably pyrethroid insecticides.

The compounds that are applied in the methods according to the invention can be applied to sugar cane, citrus, rapeseed and potato plants, including genetically modified plants.

The compounds that are applied in the methods according to the invention are used on sugarcane, citrus, rapeseed and potato plants to control any of the following pests: Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp, Mahanarva sp , Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp., Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora and Ceratitis capitata, Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Macrosiphum sp, Aphis sp, and Phthorimaea sp.

Also, the compounds that are applied in the methods according to the invention are used on sugarcane, citrus, rapeseed and potato plants to control any of the following pests: Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp, Mahanarva sp, Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp., Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora and Ceratitis capitata, Leptinotarsa sp, Limonius sp, Agriotes sp , Empoasca sp, pysllids, Bactericera sp, Myzus sp, Aphis sp, and Phthorimaea sp.

The compounds according to the invention are preferably used on sugarcane plants to control any of the following pests: Odontotermes sp, Chilo sp, Diatraea sp, Sphenophorus sp, Migdolus sp and Mahanarva sp.; more preferably the pest is Mahanarva fimbriolata; and in particular Mahanarva sp are the preferred target pests.

The compounds according to the invention are preferably applied to rapeseed plants, preferably canola, to control any of the following pests: Phyllotreta sp, Psylliodes sp, Meligethes sp, Ceutorhynchus sp and Mamestra sp.; and in particular Phyllotreta sp and Meligethes sp are the preferred target pests.

The compounds according to the invention are preferably applied to citrus fruits, preferably oranges, tangerines, lemons, grapefruits, pomelo and limes, to control any of the following pests: Diaphorina citri, Tetranychus sp, Panonychus sp, Brevipalpus sp, Phyllocnistis citrella, Aonidiella aurantii, Phyllocoptruta oleivora and Ceratitis capitata; more preferably the pest is Mahanarva fimbriolata; and in particular Diaphorina citri are the preferred target pests.

The compounds according to the invention are preferably used on potato plants to control any of the following pests: Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Macrosiphum sp, Aphis sp, Phthorimaea sp; and in particular Leptinotarsa sp are the preferred target pests.

Also, the compounds according to the invention are preferably applied to potato plants to control any of the following pests: Leptinotarsa sp, Limonius sp, Agriotes sp, Empoasca sp, pysllids, Bactericera sp, Myzus sp, Aphis sp, Phthorimaea sp; and in particular Leptinotarsa sp are the preferred target pests.

In some embodiments, the invention relates to methods and applications wherein a compound of formula (I) is administered by an application method that corresponds in each case to one row of Table 1.

In some embodiments, the invention relates to methods and applications wherein a compound of formula (I) as component I and at least one admixture component as described below are applied in an application method that corresponds in each case to one line of Table 1.

The present invention also relates to a mixture of at least one compound of the present invention with at least one admixture component, as defined hereinafter. Preferred are binary mixtures of one compound of the present invention as component I with one admixture component, as defined hereinafter as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, especially preferably from 10:1 to 1:10. In such binary mixtures, components I and II can be used in equal amounts, or an excess of component I or an excess of component II can be used.

The admixed components of the mixture may be selected from pesticides, in particular insecticides, nematicides and acaricides, fungicides, herbicides, plant growth regulators, fertilizers and the like. Preferred admixture components of the mixture are insecticides, nematicides and fungicides.

As stated above, in one embodiment, the pesticide compound of formula (I) can be combined and used in a mixture with at least another active compound II used in agriculture, such as another insecticidal active or fungicidal active agent. In another In an embodiment of the invention, the pesticide compound of formula (I) can be combined and used in mixture with more than one other active compound used in agriculture. Thus, the pesticide compound of formula (I) can be combined and used in mixture with more than one other insecticide and/or more than one fungicide.

For example, a pesticide compound of formula (I) can be combined and used in mixture with one, two, three or four other agriculturally active compounds/mixture ingredients selected from pesticides, in particular insecticides, nematicides and acaricides, fungicides, herbicides, growth regulators plants, fertilize. Preferred admixture components are insecticides, nematicides and fungicides.

Pesticides/pesticide-active compounds with which mixtures according to the invention can be used and with which potential synergistic effects can be obtained, such pesticides are, for example, described in WO 2014/167084.

One skilled in the art is familiar with such compounds and knows which compounds are active against a particular target organism.

In a further embodiment, the invention relates to mixtures containing a compound of formula (I) as described above, in particular compound I-R-1 and at least one compound II, which is a meta-aldehyde, in particular granular meta-aldehyde.

The present invention relates to a mixture of at least one compound I or a non-racemic compound of formula (I) or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R-1 or a compound I-R-1, in accordance with the present invention, as component I with at least at least one admixed component of mixture II, as indicated above. In one embodiment of the invention, the invention relates to binary mixtures of one component I with one admixed component of the mixture II as component II, as described above.

Preferred weight ratios for such binary mixtures are from 10,000:1 to 1:10,000, preferably from 7000:1 to 1:7000, also preferably from 5000:1 to 1:5000, also preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, also more preferably from 70:1 to 1:70, particularly preferably from 25:1 to 1:25, also particularly preferably from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I or an excess of component II may be used.

In the mixtures of the present invention, the ingredients can be used sequentially or in combination with each other, if necessary also added only immediately before use (tank mix). For example, the plant(s) may be sprayed with Compound II either before or after treatment with Compound I.

Insecticidal compositions for use typically contain from 0.001 to 95 wt. %, preferably from 0.1 to 45 wt. %, and more preferably from 1 to 25 wt. % of at least one repellent and/or insecticide.

Ready-to-use preparations contain compounds active against parasites, preferably ectoparasites, in concentrations of 10 ppm. up to 80 wt. %, preferably from 0.1 to 65 wt. %, more preferably from 1 to 50 wt. %, most preferably from 5 to 40 wt. %.

Preparations that are diluted before use contain compounds that act against ectoparasites in concentrations ranging from 0.5 to 90 wt. %, preferably from 1 to 50 wt. %.

The compounds of the invention can be used in the methods of the present invention in mixtures with fertilizers (eg nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable types of formulations include fertilizer granules. The mixtures preferably contain up to 25 wt. % in accordance with the invention.

An additional admixture component may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complementary activity (eg, increasing the speed of action or overcoming the repellent) of the compounds in accordance with the invention; or help overcome or prevent the development of resistance to individual components. The specific additional active ingredient will depend on the intended use of the composition.

The compounds of the invention can be mixed with soil, peat or other root media to protect plants from seed-borne, soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxane and dodecylimidazole.

The invention also relates to agrochemical compositions containing an auxiliary substance and at least one compound according to the present invention or a mixture thereof.

The agrochemical composition contains a pesticide effective amount of a compound of the present invention or a mixture thereof. The term "pesticidal effective amount" is defined below.

The compounds of the present invention or mixtures thereof can be formulated into conventional types of agrochemical compositions, for example, solutions, emulsions, suspensions, dusting powders, powders, pastes, granules, compacts, capsules and mixtures thereof. Examples for composition types are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg CS, ZC), pastes, lozenges , wettable or dusting powders (e.g. WP, SP, WS, DP, DS), pressed products (e.g. BR, TV, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal preparations (eg LN), as well as gel formulations for treating plant propagation materials such as seeds (eg GF). These and additional types of compositions are defined in the "Catalog of pesticide formulation types and international coding system", Technical Mono-graph No. 2, 6th ed. May 2008, CropLife International.

The compositions are prepared in a known manner as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples of suitable excipients are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration aids, protective colloids, adhesives, thickeners, wetting agents, repellents , attractants, eating stimulants, compatibilizers, bactericides, antifreezes, antifoaming agents, dyes, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as oil fractions with a medium to high boiling point, for example kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acid; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, for example silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, for example, grain flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

Suitable surfactants include surfactants such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants may be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration aid, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International ed., or North American ed.).

Suitable anionic surfactants are alkali, alkaline earth metal or ammonium sulfonate salts, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkyl phenols sulfonates, alkoxylated aryl phenols sulfonates, condensed naphthalene sulfonates, dodecyl and tridecyl benzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are esters of phosphoric acid. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkyl phenol ethoxylates.

Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1-50 equivalents. For alkoxylation, ethylene oxide and/or propylene oxide can be used, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose-glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are type A-B or type A-B-A block polymers, which contain polyethylene oxide and polypropylene oxide blocks, or type A-B-C, which contain alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or comb-shaped polymers of polyacids. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds that have little or no pesticidal activity and which improve the biological effectiveness of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils and other excipients. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates and silicates.

Suitable bactericides are derivatives of bronopol and isothiazolinone, such as alkyl isothiazolinones and benzisothiazolinones.

Suitable antifreezes include ethylene glycol, propylene glycol, urea and glycerin.

Suitable antifoaming agents include silicones, long chain alcohols and fatty acid salts.

Suitable dyes (eg red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic dyes (eg, iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg, alizarin, azo, and phthalocyanine dyes).

Suitable tackifiers or binders are polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples of composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of compound I according to the invention and 5-15 wt% of a wetting agent (for example, alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (for example, alcohols) to 100 wt%. The active substance dissolves when diluted with water.

ii) Dispersible concentrates (DC)

5-25% wt. compound I in accordance with the invention and 1-10 wt% of a dispersant (for example, polyvinylpyrrolidone) are dissolved in an organic solvent (for example, cyclohexanone) to 100 wt%. When diluted with water, a dispersion is formed.

iii) Emulsifiable concentrates (EC)

15-70% wt. compound I in accordance with the invention and 5-10% by weight, emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (for example, an aromatic hydrocarbon) to 100% of the mass. When diluted with water, an emulsion is formed.

iv) Emulsions (EW, EO, ES)

5-40% wt. compounds I according to the invention and 1-10% by weight, emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight. a water-insoluble organic solvent (eg, an aromatic hydrocarbon). This mixture is added to water up to 100% wt. using an emulsifying device and bring to a homogeneous emulsion. When diluted with water, an emulsion is formed.

v) Suspensions (SC, OD, FS)

In a ball mill with a stirrer, 20-60% by weight, compounds I in accordance with the invention are crushed with the addition of 2-10% by weight. dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), 0.1-2% by weight. thickener (for example, xanthan gum) and water up to 100% wt. to obtain a thin suspension of the active substance. When diluted with water, a stable suspension of active substances is formed. For the FS type of composition, up to 40% by weight of a binder (for example, polyvinyl alcohol) is added.

vi) Water dispersible granules and water soluble granules (WG, SG)

50-80% wt. compounds I according to the invention are finely ground with the addition of dispersants and wetting agents (eg sodium lignosulfonate and alcohol ethoxylate) to 100% by weight and obtained in the form of water-dispersible or water-soluble granules using technical equipment (eg extrusion, spray tower , fluidized bed). When diluted with water, a stable dispersion or solution of active substances is formed.

vii) Water dispersible powders and water soluble powders (WP, SP, WS)

50-80% wt. compounds I in accordance with the invention are ground in a rotor-stator mill with the addition of 1-5% wt. dispersants (for example, sodium lignosulfonate), 1-3% wt. wetting agents (for example, alcohol ethoxylate) and a solid carrier, for example, silica gel, up to 100 wt%. When diluted with water, a stable dispersion or solution of active substances is formed.

viii) Gel (GW, GF)

In a ball mill with a stirrer, 5-25% wt. compounds I in accordance with the invention are crushed with the addition of 3-10% of the mass. dispersants (for example, sodium lignosulfonate), 1-5% wt. thickener (for example, carboxymethylcellulose) and water up to 100% wt. to obtain a thin suspension of the active substance. When diluted with water, a stable suspension of the active substance is formed.

ix) Microemulsion (ME)

5-20% wt. compounds I in accordance with the invention are added to 5-30% of the mass. organic mixture of solvent (for example, fatty acid dimethylamide and cyclohexanone), 10-25% by weight. mixtures of surfactants (eg alcohol ethoxylate and arylphenol ethoxylate), and water up to 100%. This mixture is stirred for 1 hour to spontaneously obtain a thermodynamically stable microemulsion.

x) Microcapsules (CS)

Oil phase containing 5-50% wt. compound I according to the invention, 0-40% wt. water-insoluble organic solvent (for example, an aromatic hydrocarbon), 2-15 wt%. acrylic monomers (eg methyl methacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50% by weight of compound I according to the invention, 0-40% by weight. a water-insoluble organic solvent (eg, an aromatic hydrocarbon), and an isocyanate monomer (eg, eg, diphenylmethene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (eg, polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is 1-10% by weight. % Mass. refers to general CS composition.

xi) Dust-like powders (DP, DS)

1-10% wt. compounds I in accordance with the invention are finely ground and thoroughly mixed with a solid carrier, for example, finely ground kaolin, up to 100 wt%.

xii) Granules (GR, FG)

0.5-30% wt. compounds I in accordance with the invention are finely ground and combined with a solid carrier (for example, silicate) up to 100 wt%. Granulation is achieved by extrusion, spray drying or fluidized bed.

xiii) Ultra Low Volume (UL) Liquids

1-50% wt. compounds I according to the invention are dissolved in an organic solvent, for example an aromatic hydrocarbon, up to 100% by weight.

Types of compositions i) to xi) may optionally contain additional excipients, such as 0.1-1 wt%. bactericides, 5-15% wt. antifreeze, 0.1-1% wt. antifoam agents 0.1-1% wt. dyes.

Agrochemical compositions typically contain between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight, of active substance. The active substances are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Various types of oils, wetting agents, adjuvants, fertilizers, or trace elements, and other pesticides (eg, herbicides, insecticides, fungicides, growth regulators, antidotes) may be added to the active substances or to compositions that contain them, as a premix or, if necessary, substances not for immediate use (tank mixture). These agents may be mixed with the compositions of the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition in accordance with the present invention, typically from a pre-use preparation device, a backpack sprayer, a spray tank, a spray unit, or an irrigation system. Typically, the agrochemical composition is diluted with water, buffer, and/or other excipients to the desired concentration for use, thereby obtaining ready-to-use spray solutions or agrochemical compositions in accordance with the present invention. Typically, from 20 to 2000 liters, preferably from 50 to 400 liters of ready-to-use spray solution are used per hectare of agricultural suitable area.

According to one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a two- or three-component mixture, can be mixed by the user himself in the spray tank and, if necessary, additional excipients can be added.

In a further embodiment, either the individual components of the composition in accordance with the present invention or partially pre-mixed components, for example, components containing the compounds of the present invention and/or admixed components of the mixture as defined above, can be mixed by the user in the spray tank, and, in If necessary, additional excipients and additives can be added.

In a further embodiment, either the individual components of the composition in accordance with the present invention or partially pre-mixed components, for example, components containing compounds of the present invention and/or admixed components of the mixture as defined above, can be used together (for example, in the case of a reservoir mixture ) or sequentially.

The compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds or soil or water in which plants grow, from attack or infestation by invertebrate pests. Therefore, the present invention also relates to a plant protection method which includes contacting crops, plants, plant propagation materials such as seeds or soil or water in which plants grow, for protection against attack or infestation by invertebrate pests, with a pesticide an effective amount of a compound of the present invention.

The compounds of the present invention are also suitable for use in the suppression or control of invertebrate pests. Therefore, the present invention also relates to a method for suppressing or controlling invertebrate pests, which includes contacting invertebrate pests, their habitat, breeding sites or food resources or crops, plants, plant propagation materials such as seeds, or soil, or area, material or environment in which invertebrate pests grow or may grow, with a pesticidal effective amount of a compound of the present invention.

The compounds of the present invention are effective both upon contact and when ingested. In addition, the compounds of the present invention can be used at any and all stages of development, such as eggs, larvae, pupae, and adults.

The compounds of the present invention may be used as such or in compositions containing them as defined above. In addition, the compounds of the present invention can be used together with an admixture component as defined above, or in the form of compositions containing said mixtures, as defined above. The components of said mixture can be applied simultaneously, together or separately or sequentially, which means immediately one after the other, thereby creating the mixture "in situ" on the desired site, for example, a plant, and the sequence of application, in the case of separate application, is usually not has no effect on the result of control values.

Application can be made both before and after pest infestation of crops, plants, plant propagation materials such as seeds, soil or area, material or environment.

Suitable applications include, but are not limited to, soil treatment, seed treatment, in-furrow application, and foliar application. Soil treatment methods include soaking the soil, drip irrigation (applying drops to the soil), dipping roots, tubers or bulbs, or injecting into the soil. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. In-furrow application typically includes the steps of creating a furrow in the cultivated land, seeding the furrow with seed, applying a pesticide active compound to the furrow, and closing the furrow. Foliar application refers to the application of a pesticide active compound to the foliage of plants, for example, using spray equipment. When applied to foliage, it may be useful to modify pest behavior through the use of pheromones in combination with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to one of ordinary skill in the art and are publicly available from pheromone and chemical signal databases such as http://www.pherobase.com.

The use of the compounds according to the invention is preferably carried out in relation to sugar cane, citrus, rapeseed or potato crops. Application can be carried out before infection or in the presence of a pest. Application of the compounds according to the invention can be carried out according to any of the usual application methods, for example foliar application, drench application, soil application, in-furrow application, etc.

Pest control can be accomplished by foliar application or by drenching, which is the preferred application mode according to the invention.

In another preferred embodiment of the invention, the application method is impregnation or foliar method;

In another preferred embodiment of the invention, the application method is impregnation;

In another preferred embodiment of the invention, the application method is foliar;

In another preferred embodiment of the invention, the compounds according to the invention are applied to sugar cane, citrus, rapeseed, or potato crops by soil application or drenching;

In another preferred embodiment of the invention, the plant is sugar cane and the method of application is impregnation;

In another preferred embodiment of the invention, the plant is rapeseed and the application method is foliar;

In another preferred embodiment of the invention, the plant is a citrus fruit and the application method is drenching or foliar application;

In another preferred embodiment of the invention, the plant is a citrus fruit and the method of application is impregnation;

In another preferred embodiment of the invention, the plant is a citrus fruit and the application method is foliar;

In another preferred embodiment of the invention, the plant is a potato and the application method is foliar;

As used herein, the term "contacting" includes both direct contact (applying compounds or compositions directly to the pest animal or plant, typically the foliage, stems or roots of the plant) and indirect contact (applying compounds/compositions to a locus, i.e. i.e. place of distribution, place of mass reproduction, plant, seeds, soil, area, material or environment in which the pest grows or may grow, animal pests or plants).

The term "animal pest" includes arthropods, gastropods and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects that are of particular importance to crops are commonly referred to as crop pests.

The compounds of the invention, or pesticide compositions containing them, can be used to protect growing plants and crops from attack or infestation by animal pests, especially pests of sugar cane, citrus, rapeseed or potato plants, by contacting the plant/crop with a pesticidal effective amount compounds according to the invention. The term "crop" refers to both cultivated and harvested crops.

The compounds according to the invention can be used in combination with an attractant. An attractant is a chemical substance that causes insects to migrate to the site of application. For the control of stink bugs, it may be advantageous to apply the compound according to the invention with an attractant, especially when the application is foliar. Pests are often close to the ground and applying an attractant can encourage the plant to migrate towards the active ingredient.

Suitable attractants include glucose, sucrose, salt, glutamate, citric acid, soybean oil, peanut oil and soymilk. Of particular interest are glutamate and citric acid, with citric acid being preferred.

The attractant may be premixed with the compound of the invention prior to use, for example as a ready-mix or tank mix, or by simultaneous or sequential application to plants. Suitable rates of attractants are, for example, 0.02 kg/ha - 3 kg/ha.

The compounds according to the invention are preferably used to control pests of sugarcane, citrus, rapeseed or potato plants at an application rate of 1-500 g/ha, preferably 10-100 g/ha.

The term "crop" refers to both growing and harvested crops.

The term "plant" includes grains, such as durum and other wheat, rye, barley, triticale, oats, rice or corn (feed corn and sweet corn/sweet and field corn); beets, such as sugar beets or fodder beets; fruits such as pome, stone and soft fruits such as apples, pears, plums, peaches, nectarines, almonds, cherries, papaya, strawberries, raspberries, blackberries or gooseberries; legumes such as beans, lentils, peas, alfalfa or soybeans; oilseeds such as rapeseed (canola), turnip, mustard, olives, sunflowers, coconut, cocoa beans, castor beans, oil palms, groundnuts or soybeans; Cucurbitaceae, such as pumpkins, pumpkins, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as eggplant, spinach, lettuce (such as iceberg lettuce), endive, cabbage, asparagus, cabbage, carrots, onions, garlic, leeks, tomatoes, potatoes, squash or bell peppers; bay plants such as avocado, cinnamon or camphor; energy plants and raw material plants such as corn, rapeseed, soybeans, sugar cane or oil palms; tobacco; nuts, such as walnuts; pistachios; coffee; tea; bananas; grapes (table grapes and wine grapes); hop; sweet leaf (also called stevia); natural rubber plants or ornamental and forest plants such as flowers (eg carnations, petunias, geraniums/pelargoniums, tricolor violets and impatiens), shrubs, broadleaf trees (eg poplars) or evergreens such as conifers; eucalyptus; turf; grass for lawns; grass, such as grass for animal feeding or grass for ornamental purposes. Preferred plants include potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, canola, legumes, sunflowers, coffee or sugar cane; fruits; grape; ornamental plants; or vegetables such as cucumbers, tomatoes, beans or pumpkins.

The term "plant" should be understood to include genetically modified plants that have been modified either by breeding, or by mutagenesis or genetic engineering, or a combination thereof.

Plants that have been modified by mutagenesis or genetic engineering and of particular commercial importance include, for example, alfalfa, rapeseed (e.g. oilseed rape), beans, cloves, chicory, cotton, eggplant, eucalyptus, flax, lentils, corn , melon, papaya, petunia, plum, poplar, potato, rice, soybeans, pumpkin, sugar beets, sugar cane, sunflowers, sweet peppers, tobacco, tomatoes and grains (e.g. wheat), in particular maize, soybeans, cotton, wheat and rice In plants that have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the plant's genetic material. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A, cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1, and ppo5. Mutagenesis, or integration of one or more genes, is performed to improve certain properties of a plant. Such properties, also known as traits, include abiotic stress tolerance, growth/yield modification, disease resistance, herbicide tolerance, insect resistance, modified product quality and pollination control. Of these properties, herbicide tolerance, such as imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular value. Several plants have been rendered tolerant to herbicides by mutagenesis, such as Clearfield® oilseed rape tolerant to imidazolinones such as imazamox. Alternatively, genetic engineering techniques have been used to make plants such as soybeans, cotton, corn, beets and oilseed rape tolerant of herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® ( glufosinate). In addition, resistance to insects is important, in particular resistance to insects that belong to the order lepidopteran and resistance to insects that belong to the order coleopteran. Insect resistance is usually achieved by modifying plants by integrating the cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and encoding the corresponding Bt toxins. Genetically modified insect-resistant plants are commercially available under trade names including WideStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, and Intacta®. Plants can be modified by mutagenesis or genetic engineering, either for a single trait (single traits) or for a combination of traits (packaged traits). Packaged traits, such as the combination of herbicide tolerance and insect resistance, are becoming increasingly important. In general, all relevant modified plants in combination with single or stacked traits, as well as detailed information on mutagenized or integrated genes and related events, are available on the websites of the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http http://www.isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http://cera-gmc.org/GMCropDatabase).

The compounds according to the invention are suitable for use on any sugarcane, citrus, rapeseed and potato plants, including those that have been genetically modified to provide resistance to active ingredients such as herbicides, or to produce biologically active compounds that control with plant infestation by pests.

In a further preferred embodiment of the invention, transgenic sugarcane, citrus, rapeseed and potato plants and varieties of these plants obtained by genetic engineering methods are treated, if necessary in combination with conventional methods (Genetically Modified Organisms) and parts thereof. In particular, plants of cultivars that are in each case commercially available or in use are treated in accordance with the invention. Plant cultivars are plants that have new properties (“traits”) that have been obtained through conventional breeding, mutagenesis, or recombinant DNA methods.

These can be varieties, bio- or genotypes. Depending on the plant species or plant variety, its location and growing conditions (soil, climate, growing season, nutrition), the treatment according to the invention can also lead to super-additive “synergistic” effects.

Thus, for example, reduced application rates and/or expanded spectrum of activity and/or increased activity of substances and compositions that can be used in accordance with the invention, better plant growth, increased resistance to high or low temperatures, increased resistance to drought, water or salt content in the soil, increased flowering, easier harvesting, faster ripening, higher yield, higher quality and/or higher nutritional value of harvested products, better storage stability and/or processing ability of harvested products are possible, which exceeds the expected effects.

Preferred transgenic sugarcane, citrus, rapeseed and potato plants or varieties of these plants (obtained by genetic engineering) to be treated in accordance with the invention include all plants that, as a result of genetic modification, have received genetic material that imparts particularly advantageous properties. to these plants.

Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought, water or soil salts, improved flowering quality, easier harvesting, faster ripening, higher yield, higher quality and/ or higher nutritional value of the harvested crop, better storage stability and/or processing ability of the harvested crop.

Additional and particularly noted examples of such traits are improved plant protection from animal and microbial pests such as insects, mites, pathogenic fungi, bacteria and/or viruses, as well as increased plant tolerance to certain herbicidal active compounds.

Surprisingly, it has been found that the pesticidal activity of the compounds of the present invention can be enhanced by the insecticidal trait of the modified plant. In addition, the compounds of the present invention have been found to be useful for preventing insect resistance to insecticidal traits or for controlling pests that have already become resistant to the insecticidal traits of the modified plant. In addition, the compounds of the present invention are useful for controlling pests against which the insecticidal trait is not effective, so that additional insecticidal activity can be advantageously used.

The term "plant propagation material" refers to all the generative parts of a plant, such as seeds and vegetative plant material such as cuttings and tubers (eg potatoes), that can be used to propagate the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, shoots and other plant parts. Seedlings and young plants that are to be transplanted after germination or emergence from the soil may also be included. These plant propagation materials can be treated prophylactically with a plant protection compound either during or before planting or transplanting.

The term "seed" covers the seeds and vegetative shoots of plants of all kinds, including, but not limited to, true seeds, parts of seed tubers, root shoots, corms, bulbs, fruits, tubers, grains, cuttings, cuttings and the like. and means, preferably, actual seeds.

In general, "pesticidally effective amount" means the amount of active ingredient necessary to achieve an observable effect on growth, including the effects of necrosis, death, developmental arrest, prevention and removal, destruction or otherwise reduction in the occurrence and activity of the target organism. The pesticidally effective amount may vary for different compounds/compositions used in the invention. The pesticidally effective amount of the compositions will also vary depending on prevailing conditions, such as the desired pesticidal effect and duration, weather, target species, locus, route of application, and the like.

In the case of soil treatment, furrow application or application to an insect habitat or nest, the amount of active ingredient is from 0.0001 to 500 g per 100 m ² , preferably from 0.001 to 20 g per 100 m ² .

For use in the treatment of crop plants, for example when applied to leaves, the application rate of the active ingredients of the present invention may be from 0.0001 g to 4000 g per hectare, for example from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare. hectare, preferably 1 g to 100 g per hectare, more desirably 10 g to 50 g per hectare, for example 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or from 40 to 50 g per hectare.

The compounds of the present invention are also suitable for use in seed treatments to protect seeds from insect pests, in particular from soil-borne insect pests, and the emerging roots and shoots of seedlings against soil-borne pests and foliar insects. Therefore, the present invention also relates to a method for protecting seeds from insects, in particular from soil insects, and the roots and shoots of seedlings from insects, in particular from soil and foliar insects, the method comprising treating the seeds before sowing and/or after germination with a compound of the present inventions. It is preferable to protect the roots and shoots of seedlings. It is more preferable to protect the shoots of seedlings from piercing and sucking insects, gnawing insects and nematodes.

The term "seed treatment" includes all relevant seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting, and in-furrow application methods. Preferably, the application of the active compound by seed treatment is carried out by spraying or by dusting the seeds before sowing the plants and before germination of the plants.

The present invention also includes seeds containing or coated with an active compound. The term "coated and/or containing" generally means that the active ingredient is substantially on the surface of the propagation product upon application, although more or less of the ingredient may penetrate into the propagation product depending on the method of application. When said propagation product is planted (transplanted), it can absorb the active ingredient.

In addition, the active compound can also be used to treat the seeds of plants that have been modified by mutagenesis or genetic engineering and that are, for example, tolerant to the action of herbicides or fungicides or insecticides. Such modified plants are described in detail above.

The concentrations of the active substance in the ready-to-use formulations, which can be obtained after two to tenfold dilution, are preferably from 0.01 to 60 wt. %, more preferably from 0.1 to 40 wt. %.

Preferably, the FS formulation is used to treat the seeds. Typically, an FS formulation may contain 1-800 g/L active ingredient, 1-200 g/L surfactant, 0-200 g/L antifreeze, 0-400 g/L binder, 0-200 g/L pigment and up to 1 liter of solvent, preferably water.

Particularly preferred FS formulations of the compounds of the present invention for seed treatment typically contain from 0.1 to 80 wt. % (1-800 g/l) of active ingredient, from 0.1 to 20 wt. % (1-200 g/l) of at least one surfactant, for example, 0.05-5 wt. % wetting agent and from 0.5 to 15 wt. % dispersing agent, up to 20 wt. %, for example, from 5 to 20% antifreeze, from 0 to 15 wt. %, for example 1-15 wt. % pigment and/or coloring matter, from 0 to 40 wt. %, for example 1-40 wt. % binder (tackifier/adhesive), optionally up to 5 wt. %, for example from 0.1 to 5 wt. % thickener, optionally 0.1 to 2% antifoam agent, and optionally a preservative such as a biocide, antioxidant or the like, for example, in an amount of 0.01 to 1 wt. % and filler/carrier up to 100 wt. %.

Examples:

The present invention is illustrated in more detail by the following example, without limitation.

The compound of formula (I) was prepared in a manner similar to that disclosed in WO 2014/167084.

The compound of formula I-R-1 was prepared by the method described herein in the specification.

Analytical data for Compound I (racemic) and I-R-1 are presented in Table 2 below.

Test compound I-R-1 used in the biological examples below contains ≥95% enantiomeric excess unless otherwise stated.

1. Colorado potato beetle, Leptinotarsa decimlineata:

Foliar Application: Field tested. The plots were arranged in 5-m rows in 4 replicates. Compound I-R-1 was applied. Forage damage assessments were conducted 6, 15 and 20 days after application for the entire site. Values followed by the same letter within each assessment date are not significantly different (α=0.05) using LSD.

Conclusion: Compound I-R-1 showed good efficacy against L. decimlineata when applied foliarly in terms of reducing feed damage (Table 3).

Since mesoionic compounds are also described in WO2014/167084 as pest control agents, the following compounds, disclosed as C-6 and C-19 in WO 2014/167084, were prepared in accordance with the methods presented in WO 2014/167084.

2. Colorado potato beetle (CPB, Leptinotarsa decemlineata) Submersible biotest (foliar method) with potato plants

Serial dilutions of TGAI are carried out in a 0.01% solution of a 50:50 kinetic solvent (acetone: H2O). For a potato plant, the true leaves are cut from the plant, processed by dipping into a bowl with an acetone-resistant plastic liner, and placed in a glass flask filled with stem water to prevent dehydration of the leaves. The leaves are air dried in a fume hood and transferred to Petri dishes pre-soaked with filter paper moistened with 2.5 ml of water. Leaves were inoculated with five 2nd instar CPVs per plate. 6 repetitions/treatment and one rate (100 ppm)/test analogue. Petri dishes are kept for 5 days after infection at 250°C, 50% relative humidity and a 14/10 light/dark cycle in a walk-through chamber. Both food damage and mortality from SRS were assessed in plants.

Results:

From the following Tables 5 and 6, everything indicated that both C-6 and C-19 at 100 ppm. turned out to be inactive against CPB according to the immersion assay in potato plants. Both Compound I and Compound I-R-1 at 100 ppm. were active.

Claims (34)

1. A method for controlling invertebrate pests of potato plants, infestation or infection by invertebrate pests, which includes the stage of contacting the plant, its parts, material for its propagation, plant locus, pests, their food resources, distribution or propagation sites with a pesticide effective amount compounds of formula I-R-1 or its salts. 2. The method according to claim 1, where the compound of formula I-R-1 is applied by foliar or impregnation method. 3. Method according to claim 1 or 2, wherein the compound of formula I-R-1 is applied by foliar application. 4. Method according to claim 1 or 2, wherein the compound of formula I-R-1 is applied by impregnation. 5. A method for controlling invertebrate pests of potato plants, which includes the stage of contacting the plant, its parts, material for its propagation, pests, their food resources, place of distribution or places of propagation with a composition containing a compound of formula I-R-1 or a salt thereof, and one or more other admixed components of the mixture selected from pesticide active compounds, in mass ratios from 10,000:1 to 1:10,000. 6. The method according to claim 5, where the composition is applied by the foliar method or by impregnation. 7. Method according to claim 5 or 6, where the composition is applied by foliar method. 8. Method according to claim 5 or 6, where the composition is applied by impregnation. 9. A method of protecting potato plants, plant propagation material from attack or infection by invertebrate pests, which includes the stage of bringing the plant, its parts, propagation material, plant locus, pests, their food resources, distribution or propagation sites into contact with a pesticide effective amount of compound of formula I-R-1 or a salt thereof, or a composition containing a compound of formula I-R-1 or a salt thereof, and one or more other admixed components of the mixture selected from pesticide active compounds, in mass ratios from 10,000:1 to 1:10,000. 10. The method of claim 9, wherein the compound of formula I-R-1 as defined in claim 9 or the composition as defined in claim 9 is applied by a foliar or infiltration method. 11. The method of claim 9 or 10, wherein the compound of formula I-R-1 as defined in claim 9 or the composition as defined in claim 9 is applied by a foliar method. 12. The method of claim 9 or 10, wherein the compound of formula I-R-1 as defined in claim 9 or the composition as defined in claim 9 is applied by impregnation. 13. Method according to any one of paragraphs. 1-12, where invertebrate pests are selected from COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanicola, Agriotes lineatus, Agriotes obscurus, Agrotis ipsilon, Amphimallon solstitialis, Amrasca devastans, Aphis fabae, Aphis frangulae, Aphis gossypii, Aphis nasturtii, Aphis spiraecola, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Empoasca devastans, Empoasca fabae, Epitrix spp., Heliothis zea, Henosepilachna vigintioctomaculata, Heterodera spp., Hol otrichia oblita, Leptinotarsa decemlineata, Limonius canus, Limonius californicus, Ctenicera pruinina, Liriomyza spp., Macrosiphum euphorbiae, Macrosteles fascifrons, Meloidogyne hapla, Meloidogyne chitwoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus ornatus, Pemphigus sp., Peridroma saucia, Phthorimaea operculella , Phthorimaea spp. ., Pratylenchus penetrans, P. neglectus, Paratrichodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Rhopalosiphum rufiabdominalis, Russelliana solanicola Tuthill, Smynthurodes betae, Spodoptera eridania, Spodoptera frugiperda, Spodoptera litura. 14. Method according to any one of paragraphs. 1-12, where the plant is a genetically modified plant. 15. Use of a compound of formula I-R-1 or a salt thereof, or a composition containing a compound of formula I-R-1 or a salt thereof, and one or more other admixed components of the mixture selected from pesticide active compounds, in mass ratios from 10,000:1 to 1:10,000, for controlling pests of potato plants. 16. Use of a compound of formula I-R-1 or a salt thereof, or a composition containing a compound of formula I-R-1 or a salt thereof, and one or more other admixed components of the mixture selected from pesticide active compounds, in mass ratios from 10,000:1 to 1:10,000, for protecting growing potato plants, plant propagation material from attack or infestation by invertebrate pests of potato plants. 17. Application according to claim 15 or 16, where the invertebrate pests are selected from COL: Elateridae, Amrasca biguttula biguttula, Acizzia solanicola, Agriotes lineatus, Agriotes obscurus, Agrotis ipsilon, Amphimallon solstitialis, Amrasca devastans, Aphis fabae, Aphis frangulae, Aphis gossypii, Aphis nasturtii, Aphis spiraecola, Aulacorthum circumflexum, Aulacorthum solani, Autographa californica, Bactericera nigricornis, Bactericera cockerelli, Bemisia argentifolii, Circulifer tennelus, Diabrotica speciosa, Empoasca devastans, Empoasca fabae, Epitrix spp., Heliothis zea, Henosepilachna vigint ioctomaculata, Heterodera spp., Holotrichia oblita, Leptinotarsa decemlineata, Limonius canus, Limonius californicus, Ctenicera pruinina, Liriomyza spp, Macrosiphum euphorbiae, Macrosteles fascifrons, Meloidogyne hapla, Meloidogyne chitwoodi, M. incognita, Monomorium pharaonic, Myzus ascalonicus, Myzus ornatus, Pemphigus sp., Peridroma saucia, Phthorimaea operculella, Phthorimaea spp., Pratylenchus penetrans, P. neglectus, Paratrichodorus sp., Pseudoplusia includens, Rhopalosiphoninus latysiphon, Rhopalosiphum ruflabdominalis, Russelliana solanicola Tuthill, Smynthurodes betae, Spodoptera eridania, Spodoptera frugiperda, Spodoptera litura. 18. Use according to claim 15 or 16, where the plant is a genetically modified plant.