EP2007201A2 - Use of 3-(2,4,6-trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylene- 3-dihydrofuran-2-one for controlling diptera from the cecidomyiidae family - Google Patents

Abstract

The invention relates to the use of 3-(2,4,6-trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylene-?<SUP>3</SUP>-dihydrofuran-2-one for controlling insects from the cecidomyiidae family.

Description

Use of 3- (2,4,6-trimethylphenyl) -4-neopentane-carbonyl-γ-5,5-tetramethylene-Δ3-dihydrofuran-2-one for the control of dipterans of the family Cecidomviidae

The present application relates to the use of 3- (2,4,6-trimethylphenyl) -4-neopentyl-carbonyloxy-5,5-tetramethylene-Δ ³ -dihydrofuran-2-one for the control of insects from the family Cecidomyiidae.

The compound 3- (2,4,6-trirnethylphenyl) -4-neopentylcarbonyloxy-5,5-tetramethylene-Δ ³ -dihydro-furan-2-one is known from EP-A-0 528 156.

Furthermore, it is known that under certain conditions spirodiclofen shows an ovicidal activity against psyllids. However, the time of application is very limited (De Maeyer et al., BCPC Conference (2002), Vol. 1, 65-72).

It is also known from EP-A-0 528 156 that 3- (2,4,6-trimethylphenyl) -4-neopentylcarbonyl-oxy-5,5-tetramethylene-Δ ³ -dihydrofuran-2-one is insecticidal. Furthermore, an effect against whiteflies WO 00/42850 and against Psylliden WO 06/002824 was known.

Surprisingly, it has now been found that 3- (2,4,6-trimethylphenyl) -4-neopentylcarbonyloxy-5,5-tetramethylene-Δ ³ -dihydrofuran-2-one is particularly well suited for controlling insects from the family Cecidomyiidae.

The present invention accordingly relates to the use of 3- (2,4,6-trimethylphenyl) -4-neopentylcarbonyloxy-5,5-tetramethylene-Δ ³ -dihydrofuran-2-one for controlling insects from the family Cecidomyiidae.

3- (2,4,6-trimethylphenyl) -4-neopentylcarbonyloxy-5 _{s-tetramethylene-5-Δ} ³ -dihydrofuran-2-one has the following formula (I):

(I) The compound of formula (I) may preferably be used for controlling insects of the genera Contarinia spp., Diplosis spp., Orseolia spp., Dasyneura spp., Cecidomya spp. be used. Examples include the following species: Contarina lycopersici, Contarinia maculipennis, Contarinia humuli, Contarina johnsoni, Contarinia tritici, Contarinia pisi, Contarina sorghicola, Contaria medicaginis, Contarinia mali, Contarinia okadai, Dasyneura brassicae, Haplodiplosis equestris, Sitodiplosis mosellana, Diplosis mori, Thecodiplosis japonensis, Prodiplosis vaccinii, Prodiplosis longifila, Asphondylia sesame, Orseolia spp., Dasineura afϊinis, Dasineura mali.

In principle, the compound of formula (I) can be used in a variety of cultures, preferably in citrus (eg limonene, grapefruit, oranges), pome fruit (eg apple, pear), vegetables (eg tomato, eggplant, beans, pepper), potatoes , Alfadfa, cotton, spices, berry fruits (eg blueberries).

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 variety rights. Plant parts are understood to mean all aboveground and underground 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 become. The plant parts also include crops and vegetative and generative propagation material, such as 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, spreading, injecting and propagating material, in particular in seeds, further by single or multilayer coating.

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, which may be obtained by genetic engineering, optionally in Combination with conventional methods were obtained (Genetic Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" has been 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 effort levels and / or extensions of the activity spectrum and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness 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 the harvested products, which exceed 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 drought or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the emmentaries , higher shelf life and / or workability of the harvested products. 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 are particularly raised the increased defense of plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a), CryIA (b), CryΙA (c ), CryllA, CryEIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter "Bt plants"). Traits also highlight the increased resistance of plants against fungi, bacteria and viruses by systemic induced resistance (SAR), 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 herbicidal 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), IMI® (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 ingredient of the formula (I) can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, active substance-impregnated natural and synthetic substances, and Very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, for example 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. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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, and 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 fumed 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 carboxymethyl cellulose, natural and synthetic powdery, granular or latex-containing 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, e.g. 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.

The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%, and besides preferably, streaking agents 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 application forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. The application is done in a custom forms adapted to the application forms.

Preparation of the compound of the formula (D:

5.45 g (20 mmol) of 3- (2,4,6-trimethylphenyl) -4-hydroxy-5,5-tetramethylene-Δ ³ -dihydrofuran-2-one (known from EP-A-0 528 156) are dissolved in 80 ml of dichloromethane initially charged, 3.04 g (30 mmol) of triethylamine and then added dropwise at 0-10 ⁰ C, a solution of 3.50 g (26 mmol) of 3,3-dimethylbutyryl chloride in 20 ml of dichloromethane.

After 2 hours, an additional 0.50 g (5 mmol) of triethylamine and 0.40 g (3 mmol) of acid chloride are added and stirred at room temperature for a further 16 hours.

For working up, it is washed twice with 10% citric acid and twice with 1N sodium hydroxide solution, the organic phase is dried with sodium sulfate and concentrated.

Further purification of the crude product is achieved by trituration with petroleum ether, suction and drying.

Yield: 4.50 g of white solid (61% of theory) of melting point: 98.degree.

Example A

Pest: Prodiplosis longuifila

Plant: paprika

The compound of formula (I) (240 SC) is applied at a rate of 144 g ai / ha with a water application rate of 500 l / ha compared to Provado Combi (SC 112.5), Confidor (SC 350) and Sevin (80 WSP) tested at the indicated rates.

The spraying is done by means of a hand-operated-back device.

The experiment is carried out in plots of about 50 m ^ and three repetitions. There are two applications at intervals of one week.

The evaluation takes place 4, 7 and 9 days after the treatment by scoring the killing of the larvae on the fruits.

Compound Application rate% of effeciency from bort g / ha 4 days 7 days 9 days

Compound of the 144 79.7 85.6 83.7 Formula (I)

Confidor 140 79.1 82.3 73.5

Provado 157 77.7 85.1 86.2

Sevin 1600 72.3 59.1 55.6

Claims

claim

Use of the compound of the formula (I)

for controlling insects of the family Cecidomyiidae.