EP2175723A1

EP2175723A1 - Use of tetramic acid derivatives for controlling viruliferous vectors

Info

Publication number: EP2175723A1
Application number: EP08773542A
Authority: EP
Inventors: Reiner Fischer; Konrad Kemper; Jürgen KÜHNHOLD; Xavier Alain Marie Van Waetermeulen; Francisco Leonel Junior Lozano
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2007-07-03
Filing date: 2008-06-20
Publication date: 2010-04-21
Also published as: US20100249121A1; JP2010531824A; WO2009003597A1; EP2011394A1; AU2008271633A1; CN101686677A; ZA201000012B; KR20100040861A; TW200917959A; MX2009013708A; BRPI0813785A2

Abstract

The invention relates to the use of tetramic acid derivatives per se and of active substance combinations that consist of known tetramic acid derivatives and other known insecticidal substances for controlling insect-transmitted viroses.

Description

Use of tetramic acid derivatives for controlling virus-transmitting vectors

The present invention relates to the use of tetramic acid derivatives alone and also of active compound combinations which consist of known tetramic acid derivatives on the one hand and other known insecticidal active compounds on the other hand, for controlling by vectors (insects) transmitted viruses.

It is already known that certain cyclic ketoenols possess herbicidal, insecticidal and acaricidal properties. The effectiveness of these substances is good, but leaves at low application rates in some cases to be desired.

Known with insecticidal and / or acaricidal action are lH-3-aryl-pyrrolidine-2,4-dione derivatives (WO 98/05638) and their cis isomers (WO 04/007448).

Also known are mixtures of compounds from WO 98/05638 with other insecticides and / or acaricides: WO 01/89300, WO 02/00025, WO 02/05648, WO 02/17715, WO 02/19824, WO 02/30199, WO 02/37963, WO 05/004603, WO 05/053405, WO 06/089665, DE-A-10342673, WO 2008/006516. However, the effect of these mixtures is not always satisfactory.

It has now been found that both the compounds of the formulas (I-1) or (1-2)

(1-1) (I-2)

both compounds are known from WO 04/007448 as well as drug combinations containing the compounds (1-1) or (1-2) and at least one agonist or antagonist of acetylcholine receptors, in particular a compound of the following formulas

Imidacloprid (Al) is known from EP-A-OO 192060

and or

Acetamiprid (A2) known from WO 91/04965

and or

Thiamethoxam (A3) is known from EP-A-00580553

and or

Nitenpyram (A4) is known from EP-A-00302389 and or

Thiacloprid (A5) is known from EP-A-00235725 and / or

Dinotefuran (A6) is known from EP-A-00649845

and or

Clothianidin (A7) is known from EP-A-00376279 and / or

Imidaclothiz (A8) is known from EP-A-OO 192060 particularly well suited for preventing virus spread in crops such as soya, cotton, beets, corn, rice, potatoes, tobacco, cereals, tropical fruits, vegetables and ornamental plants.

Growth regulating insecticides, such as the compounds of formulas (1-1) and (1-2), are generally slow in acting and have no killing effect on adult animals.

Due to the delayed onset, an application for virus control was not expected. It is quite surprising that the compounds of the formulas (I-1) and (1-2) are suitable despite the delayed onset of action for the virus control in which they control the virus-transmitting vectors. Virus-transmitting vectors are understood as meaning those insects which transmit plant pathogenic viruses, such as e.g. White flies, cicadas,

Thrips, spider mites and aphids.

Furthermore, it is surprising that the effect of the active ingredient combinations on the virus spread is much higher than the sum of the effects of the individual active ingredients. There is an unpredictable true synergistic effect and not just an effect supplement.

Preference is given to combinations of active substances containing the compound of the formula (I-1) and at least one active substance from the group of agonists or antagonists of acetylcholine receptors.

Also preferred are combinations of active substances containing the compound of the formula (I-2) and at least one active substance selected from the group of agonists or antagonists of acetylcholine receptors.

Of particular interest are the following combinations: (1-1) + (Al), (1-1) + (A2), (I-)

1) + (A3), (M) + (A4), (1-1) + (A5), (M) + (A6), (M) + (A7), (M) + (A8), ( 1-2) + (Al), (I-

2) + (A2), (1-2) + (A3), (1-2) + (A4), (1-2) + (A5), (1-2) + (A6), (1- 2) H- (A7), (1-2) + (A8).

The active ingredient combinations may also contain other fungicidal, acaricidal or insecticidal Zumischkomponenten beyond.

If the active ingredients in the active ingredient combinations in certain weight ratios are present, the improved effect is particularly clear. However, the weight ratios of the active ingredients in the drug combinations in a relatively large

Range can be varied. In general, the combinations according to the invention contain Active compounds of the formula (I-1) or (1-2) and the mixing partner in the preferred and particularly preferred mixing ratios given in the table below:

* the mixing ratios are based on weight ratios. The ratio is to be understood as the active substance of the formula (I-1): Mixture partner or formula (I-2): Mixture partner

The active compound combinations but also the compounds of the formulas (I-1) or (1-2) alone are suitable for good plant tolerance and favorable toxicity to the warmblood for preventing virus spread in soybeans, corn, rice, beets, cereals (wheat, barley, rye, oats , Triticale), tobacco, cotton, vegetables, tropical fruits, potatoes and ornamental plants.

Plant viruses with circular single-stranded DNA are preferably so-called gemini viruses such as, for example, Bean Golden Mosaic Virus (BGMV), Cassava Latend Virus (CLV), Tomato Golden Mosaic Virus (TGMV), Maize Streak Virus (MSV), Tomato Spotted Wilt Virus (TSWV), Tobacco Mosaic Virus (TMV), Tomato Mosaic Virus (ToMV), Potato Yellow Mosaic Virus (PYMV), Tomatoe Yellow Leaf Curl Virus (TYLCV), Barley Yellow Dwarf Virus (BYDV), Beet Mosaic Virus (BtMV), Beet Yellow Virus (BYV), Beet Western Yellow Virus (BWYV). The only generally described cultures to be protected are differentiated and specified below. For example, fruit vegetables and inflorescences are understood to mean vegetables, for example peppers, hot peppers, tomatoes, aubergines, cucumbers, pumpkins, courgettes, field beans, runner beans, beans, peas, artichokes, corn;

but also leafy vegetables, such as lettuce, chicory, endives, kraken, ruffians, lamb's lettuce, iceberg lettuce, leeks, spinach, chard;

tubers, root and stem vegetables, such as celery, beetroot, carrots, radishes, horseradish, salsify, asparagus, turnips, palm sprouts, bamboo shoots, as well as onion vegetables, such as onions, leeks, fennel, garlic;

and cabbage, such as cauliflower, broccoli, kohlrabi, red cabbage, cabbage, kale, savoy cabbage, Brussels sprouts, Chinese cabbage.

For example, wheat, barley, rye, oats, triticale, but also maize, millet and rice are understood to be used in cereal crops;

furthermore wine and tropical crops, such as mangoes, papayas, figs, pineapples, dates, bananas, durians, kakis, coconuts, cocoa, coffee, avocados, lychees, passion fruits, guavas,

almonds and nuts such as hazelnuts, walnuts, pistachios, cashews, Brazil nuts, pecans, butternuts, chestnuts, hickory nuts, macadamia nuts, peanuts,

in addition, soft fruits such as currants, gooseberries, raspberries, blackberries, blueberries, strawberries, cranberries, kiwis, cranberries.

In terms of application, ornamental plants are understood to be annual and perennial plants, e.g. Cut flowers such as roses, carnations, gerberas, lilies, daisies, chrysanthemums, tulips, daffodils, anemones, poppies, amyrillis, dahlias, azaleas, mallows,

but also eg bedding plants, potted plants and perennials, such as roses, marigolds, pansies, geraniums, fuchsias, hibiscus, chrysanthemums, hard-bitten lits, cyclamen, southern violets, sunflowers, begonias, furthermore shrubs and conifers such as ficus, rhododendron, spruce, fir, pine, yew, juniper, pine, oleander.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment according to the invention of the plants and plant parts with the active ingredient is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagation material, in particular in seeds, further by single or multi-layer wrapping.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" is explained above.

It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects. Thus, for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of harvested products that go beyond the actual expected effects.

The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or machinability of Emteprodukte. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryΙA (b), CryΙA (c), CryllA, CryHIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants"). As traits, the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR) are also particularly emphasized. Systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), MI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.

The active compound combinations or the active compounds (1-1) and (1-2) can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates - Trate, drug-impregnated natural and synthetic substances and Feinstverkapselungen in polymeric substances.

These formulations are prepared in a known manner, e.g. by mixing the active compound with extenders, ie liquid solvents and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.

Suitable extenders include, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified can), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).

In the case of using water as an extender, e.g. also organic

Solvent can be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes,

Chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or

Paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as

Dimethylformamide and dimethyl sulfoxide, as well as water.

Suitable solid carriers are:

e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations. Other additives may be mineral and vegetable oils.

Dyes such as inorganic pigments, eg, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and Trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%, and additionally preferably extenders and / or surface-active agents.

The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

The application is done in a custom forms adapted to the application forms.

applications

example 1

7.5 m ² plots of "Jumbo" tomatoes are treated in three replicates against the virus-borne vector Bemisia argentifolii, which is administered with a motor-driven backpack syringe, with the active ingredients (1-2) (240 SC) in one Tank mix with 0.186% ai soy oil Natur'Loleo (OL 930) and the commercial standard imidacloprid (200 SC) applied at the indicated application rates Four applications are carried out at intervals of 7 days each with a water application rate of 300 l, 300 l, 500 1 and 600 l / ha.

The evaluation takes place 25 days after the fourth treatment by scoring the virus attack with the Tomatoe Yellow Leaf Curl Virus (TYLCV) on the plants.

In the control, 11.7 out of 15 plants were infected with TYLCV. Example 2

7.5 m ² plots of tomatoes of the "Jumbo" variety are treated in 3 replications against the virus-borne vector Bemisia argentifolii.The application is carried out with a compressed air-driven backpack syringe, the active ingredient being (1-2) (240 SC) in one Tank mix with 0.186% ai soybean oil (Natur'Loleo) (930 OL) and the commercial standard imidacloprid (200 SC) at the indicated rates of application, three applications at intervals of 7 days each.The water application rates are 300 l / ha, 400 l / ha and 600 l / ha.

The evaluation takes place 14 days after the third treatment by scoring the virus attack with the Tomatoe Yellow Leaf Curl Virus (TYLCV) on the plants.

All 18 plants in the control were infested with TYLCV.

Example 3

12 m ² plots of "Carioca" bush beans are treated in three replications against the virus-borne vector Bemisia argentifolii, which is applied with a compressed air-driven backpack syringe, using the active substance Example (1-2) (240 SC) in a tank mix 0.186% ai soybean oil (Natur'L Oleo) (930 OL) and the commercial standard imidacloprid (200 SC) at the indicated rates of application.There are three applications at intervals of 7 days.The amount of water used is 300 l / ha.

The evaluation takes place 16 days after the first treatment, by scoring the virus attack with the Bean Golden Mosaic Virus (BGMV) on the plants. - -

All 10 plants in the control were infected with the BGMV.

The listed plants can also be treated particularly advantageously according to the invention with the active ingredient mixture. The preferred ranges given above for the mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the mixtures specifically mentioned in the present text.

The good action for controlling virus-transmitting vectors of the active ingredient combinations is evident from the examples below. While the individual active ingredients have weaknesses in effect, the combinations show an effect that goes beyond a simple action summation.

A synergistic effect is always present in the case of various active ingredients if the effect of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.

The expected effect for a given combination of two drugs can be found in S.R. Colby, Weeds 15 (1967), 20-22) are calculated as follows:

If

X means the degree of control, expressed in% of the untreated control, when using the active substance A in an application rate of m g / ha or in a concentration of m ppm,

Y means the degree of control, expressed in% of the untreated control, when using the active substance B in an application rate of ng / ha or in a concentration of n ppm, and E means the degree of control, expressed in% of the untreated control, when using the active compounds A and B at application rates of m and ng / ha or in a concentration of m and n ppm,

then

E = X + Y-

If the actual level of control is greater than calculated, the combination is over-additive in its control, i. there is a synergistic effect. In this case, the degree of control actually observed must be greater than the expected kill rate (E) value calculated from the above formula.

After the desired time, the control is determined in%. 100% means that no plants were infected with viruses; 0% means that all plants were infected with viruses.

Example 4

7.5 m ² plots of "Jumbo" tomato tomatoes are treated in three replicates against the virus-borne vector Bemisia argentifolii using a compressed-air sprayer, using a tank mix of active ingredient (1-2) (SC 240) and imidacloprid (SC 200 ) compared to the active ingredient (1-2) (SC 240) alone in the indicated application rates with 0.186% ai soybean oil (Natur'L Oleo) (OL 930) as tank mix and imidacloprid (SC 200) solo applied four applications at intervals of 7 days each with a water application rate of 300 l / ha, 300 l / ha, 500 l / ha and 600 l / ha. The evaluation takes place 25 days after the treatment, by the virus infestation with the Tomato-Spotted- Wilt virus (TSWV) scored on the plants.

In the control, 3.3 out of 15 plants were infected with the TSWV.

Claims

- Patent claims

1. Use of compounds of the formulas (I-1) or (1-2)

(1-1) (I-2)

for controlling insect-borne viroses.

2. Use of compound of formula (1-1) according to claim 1.

3. Use of compound of formula (1-2) according to claim 1.

4. Use of active compound combinations containing the compounds of the formulas (I-1) or (1-2) and at least one agonist or antagonist of acetylcholine receptors for controlling insect-borne viroses.

5. Use of active compound combinations according to claim 4 containing at least one of the following compounds: Al, A2, A3, A4, A5, A6, A7, A8.

6. Use of compounds according to Claim 1 or of active compound combinations according to Claim 4 for combating insect-borne viroses in soya,

Cotton, beets, corn, rice, potatoes, tobacco, cereals, tropical fruits, vegetables or ornamental plants.

7. Use of compounds according to claim 1 or of active compound combinations according to claim 4 for controlling insect-borne viroses in vegetables.

8. Use of compounds according to claim 1 or of active compound combinations according to claim 4 for the control of transmitted by the whitefly virus.