Methods for enhancing residual inhibition of mites and prolongation of plants protection against infection with mites

FIELD: organic chemistry, agriculture.

SUBSTANCE: method involves carrying out a seasonal single treatment of plant leaves with asymmetrical derivative of 4,6-bis-(aryloxy)pyrimidine of the formula: wherein X means chlorine atom (Cl), nitro- or cyano-group. Invention provides enhancing the long-term time of plants protection.

EFFECT: enhanced effectiveness and valuable properties of compounds.

6 cl, 6 tbl

 

PREREQUISITES TO the CREATION of INVENTIONS

Mites cause huge economic losses of fruit plants and agricultural crops. In particular, mites consume citrus fruits and fleshy pome fruits, eating leaves and ripening fruits.

To combat infestations of mites plants are treated several times during the growing season commercial miticides (acaricides). Despite the repeated application of commercial acaricides available at the present time, there is still damage to plants caused by infestations of mites. Accordingly, research continues in the search for new and more effective acaricide funds that do not require multiple applications to protect plants from infection by ticks.

Some pyrimidine compounds that are useful as acaricide funds, are described in WO 94/02470. However, this publication does not disclose any residual acaricidal activity.

Therefore, the purpose of this invention is the provision of a method for improving or increasing residual suppression of ticks.

The purpose of this invention is the provision of a method of extending the protection of plants against infection by ticks.

These and other objectives of this invention will become more apparent from the detailed description below.

BRIEF OP is a DESCRIPTION of the INVENTION

This invention provides methods of increasing residual suppression of mites and renewal of plant protection from infestations of mites by applying to the foliage of plants susceptible to infestation by mites, acaricide effective amount of an asymmetric compound 4,6-bis(aryloxy)pyrimidine.

DETAILED description of the INVENTION

The present invention provides a method for improving residual suppression of mites which comprises applying to the foliage of plants susceptible to infestation by mites, acaricide effective amount of an asymmetric compound 4,6-bis(aryloxy)pyrimidine having the structural formula I

where X denotes Cl, nitro or cyano.

This invention also provides a method of extending the protection of plants from infestation of mites which comprises applying to the foliage of plants acaricide effective amount of an asymmetric compound 4,6-bis(aryloxy)pyrimidine of formula I.

Unbalanced connections 4,6-bis(aryloxy)pyrimidine of the present invention and the corresponding symmetric analogues of them are described in WO 94/02470. This publication discloses only the evaluation of acute (not residual) actions miticides. It has been unexpectedly discovered that when biologically equivalent to an acute dose (e.g., size LC99connections feast is Medina applied to plants, unbalanced connections 4,6-bis(aryloxy)pyrimidine of the present invention are significantly more effective for residual suppression of mites than the corresponding symmetric pyrimidine analogues.

Thus, seasonal protection against infections mites successfully can be achieved by only applying a single-ended connection 4,6-bis(aryloxy)pyrimidine of the present invention. Very favorable is that seasonal protection from one application of the asymmetric compound 4,6-bis(aryloxy)pyrimidine of the present invention significantly reduces the load on the environment related to the use of common acarida that require multiple applications to protect plants from infection by ticks.

In the preferred embodiment of the present invention unbalanced connection 4,6-bis(aryloxy)pyrimidine is 4-[(4-chloro-α,α,α-Cryptor-m-tolyl)oxy]-6-[α,α,α,4 titrator-m-tolyl) oxy]pyrimidine.

The compounds of formula I of this invention are particularly useful for residual suppression of herbivorous mites, including, but not limited to, Tetranychidae such as Tetranychus urticae, Tetranychus pacificus, Tetranychus kanzawai, Panonychus ulmi, Panonychus citri and Oligonychus pratensis; Tarsonemidae such as Phytonemus pallidus and Polyphagotarsonemus latus; Eriophyidae such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni, and Tenuipalidae, such as Brevipalpus phoenicis. In particular, asymmetric connections 4,6-bis(aryloxy)pyrimidine of the present invention is particularly useful for residual suppression Tetranychus urticae, Panonychus ulmi, Panonychus citri and Brevipalpus phoenicis.

Plants that are protected from infestations of mites for long periods of compounds of formula I of this invention include, but are not limited to, citrus plants, such as orange, grapefruit, lemon and lime; fruit with fleshy pome fruits such as Apple, pear and kiwi; culture stone fruits, such as avocado, peach, cherry, Fig, olive and mango; wine fruit crops such as grapes, strawberries and raspberries; nut crops such as almond, pecan, walnut, pistachio, cashew, hazel, chestnut, macadamia and Brazil nuts; field crops such as cotton, corn, soybeans, wheat, pumpkin, and watermelon; ornamental plants, such as flowering plants and shrubs; coffee and tea. Unbalanced connections 4,6-bis(aryloxy)pyrimidine of the present invention is particularly useful for the protection of citrus plants and pome fruit crops from infestations of mites for long periods.

To ensure long lasting residual suppression of mites, fruit and ornamental plants are usually treated with a liquid, preferably aqueous, dispersion, to whom I contains from about 1 to 100 g/HL (grams per hectoliter), preferably from 5 to 25 g/HL unbalanced connections 4,6-bis(aryloxy)pyrimidine of formula I. In practice, the variance is usually applied to the fruit or ornamental plants until runoff.

Unbalanced connections 4,6-bis(aryloxy)pyrimidine of the present invention is also useful for extending the residual suppression of mites on field crops when applied to culture sufficient to provide a dose of from about 0.01 to 1.0 kg/ha, preferably from about 0.08 to 0.3 kg/ha of active ingredient.

The term "foliage"as used here includes, but is not limited to, leaves, buds, fruits, stems, shoots, branches and/or flowers of plants. The term "fruit tree", as used here, includes, but is not limited to, citrus plants, pome fruit, stone fruit, wine, fruit and nut crops. The term "ornamental plant", as used here, includes, but is not limited to, flowering plants and shrubs. The term "field culture", as used here, includes, but is not limited to this, and vegetable crops such as pumpkin and watermelon, and row crops such as cotton, corn, soybeans and wheat.

Unbalanced connections 4,6-bis(aryloxy)pyrimidine of the present invention can be prepared in finished form in the form of emulsifiable to the of centreton, flowable concentrates or wettable powders, which are diluted with water or other suitable polar solvent, usually at the point of use, and then applied in the form of diluted funds for spraying. Unsymmetrical 4,6-bis(aryloxy)pyrimidines can also be prepared in the form of dry compacted granules, granular preparations, Farrukh Dustov, gustovich concentrates, suspension concentrates, microemulsions and the like. Such form of preparations or compositions of this invention include asymmetric connection 4,6-bis(aryloxy)pyrimidine of the present invention (or combinations thereof) in a mixture with one or more agronomically acceptable inert solid or liquid carriers.

To facilitate further understanding of the invention, the following examples are presented primarily for illustrating more specific details. Scope of the invention should not be considered limited to these examples, and it covers the full essence of what is defined in the claims.

EXAMPLE 1

Assessment of residual acaricidal activity against bimaculated spider mites in greenhouse

The leaves of Lima bean dip in 50% acetone experienced solutions. Every experienced solution contains the estimated connection in the quantity for the next 2 times the value of LC 99for bimaculated spider mite. Used here, the value of LC99is the concentration of compounds in common. per million, which kills 99 percent of bimaculated spider mites when assessing acute dose. By using the values LC99provide biologically equivalent to acute doses of the tested compounds at the beginning of the evaluation. Then the plants are allowed to dry, placed in trays with a bottom moisture, placed in a greenhouse and kept under light for 14 hours per day. The plants are then divided into samples at 0, 3 and 7 days after treatment. In each period of sampling the relevant plants are removed from the greenhouse and infect 50-60 bimaculated spider mites per leaf. After three days determine the number of adult ticks and assess the mortality of mites. The results are summarized in Table 1.

Evaluated compounds identified below. The data in Table 1 presents the number of connections for compounds of the invention and letter connections for connections comparison.

As can be seen from Table 1, the asymmetric compound 4,6-bis(aryloxy)pyrimidine of the present invention are surprisingly more effective when residual suppression bimaculated spider mites than the corresponding symmetric counterparts. This is especially unexpected re is the query result, since the original plants used biologically equivalent to an acute dose.

EXAMPLE 2

Assessment in open soil residual acaricidal activity

Residual suppression of some species of herbivorous mites on fruit and citrus trees are assessed in conditions of open ground by applying an aqueous mixture containing 5 or 15 g/HL of the test compounds, the leaves of plants by using a hose with a spray volume of from about 1000 to 2000 l/ha (i.e. before draining). The water mixture is produced by adding the appropriate quantity emulsifiable concentrate of the test compound to the water. In this evaluation emulsifiable concentrate contains 9.7 wt./wt.% the test compounds to 3.5 wt./wt.% TOXIMUL®3403F (mixture of anionic/nonionic detergents supplied by Stepan Company, Northfield, Illinois), 3.5 wt./wt.% TOXIMUL®3404F (mixture of anionic/nonionic detergents supplied from Stepan Company), and 83.3 wt./wt.% AROMATIC®200 (aromatic hydrocarbon solvent supplied by EXXON Chemicals Americas, Houston, Texas).

After application the plants are checked approximately weekly for the presence of live mites. Then evaluate the residual activity of the tested compounds by comparing the number of mites on the treated versus untreated plants. The results are summarize in the Table is izah II-VI. In Tables II-VI compounds identified by number or letter designation of the compound, as in Example 1.

As you can see from the data of Tables II-VI, single-ended connection 4,6-bis(aryloxy)pyrimidine of the present invention (4-[(4-chloro-α,α,α-Cryptor-m-tolyl)oxy]-6-[(α,α,α,4 titrator-m-tolyl)oxy]pyrimidine) provides a significantly higher level of residual suppression leprosula mite (calling lepros citrus), red Clasica and European red fruit mite than active pyrimidine analogue (4,6-bis[α,α,α,4 titrator-m-tolyl)oxy]pyrimidine).

TABLE IV
Evaluation of the application in the conditions of open ground pyrimidines against Brevipalpus phoenicis (leprosy mite) on the orange-Assessment 3
ProcessingDose (g/HL)The percentage of suppression of mites

Days after processing
7356090124
Connection 1158910010010098
from what retene 595100989880
Symmetric15971001009871
connection5969495720

TABLE V
Evaluation of the application in the conditions of open ground pyrimidines against Panonychus citri (red clasic) orange
ConnectionDoseThe percentage of suppression of mites
(g/HL)Days after processing
72130
Compound 1 of the invention15999794
Symmetric158885
connection
TABLE VI
Evaluation of the application in the conditions of open ground pyrimidines against Panonychus ulmi (red fruit mite) on Apple
ProcessingDose (g/HL)The percentage of suppression of mites

Days after processing
2142136
Connection 11597999794
inventions577929464
Symmetric1590939678
connection5777086

1. The way to increase residual suppression of mites, which includes a one-time seasonal processing of foliage plants, susceptible mites, acaricide effective amount of an asymmetric compound 4,6-bis(aryloxy)pyrimidine having the structural formula I

where X denotes C1, nitro or cyano.

2. The method according to p. 1, in which the compound is 4-[(4-chloro-(α,α,α-Cryptor-m-tolyl)oxy]-6-[(α,α,α,4 titrator-m-tolyl)oxy]pyrimidine.

3. The method according to p. 1, in which the plant is selected from the group consisting of citrus plants, pome fruit, stone fruit crops, wine fruit crops, nut crops, field crops, ornamental plants, coffee and tea.

4. The method according to p. 1, in which the plant is a fruit or ornamental plant, and the compound is applied to the foliage of plants in a dose of from about 1 to 100 g/chief

5. The method according to p. 1, in which the plant is a field crop, and the compound is applied to the foliage of plants in a dose of from about 0.01 to 1.0 kg/ha

6. The method according to p. 1, in which ticks are selected from the group consisting of Tetranychus urticae, Panonychus ulmi, Panonychus citri and Brevipalpus phoenicis.



 

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