JPS61501709A - Methods for controlling soil insects - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Methods for controlling soil insects The present invention relates to the general field of insecticides, and more particularly to 3.(2-chloride). lo-3,3,3-)lifluoro-1-propenyl)-2,2-dimethylcyclo Applying fluorinated phenylmethyl esters with propanecarboxylic acid to the soil soil insects, especially southern corn, which spends the majority of its larval stage in the soil. - Concerning methods for controlling insects such as rootworms, that is, soil insects.

U.S. Pat. No. 4,332,815 discloses that Excellent insecticide against Homoptera (Tera) and Homoptera (Iomoptera) A wide class of behaloalkyl and nylcyclo compounds have been described as active. It reveals propane carboxylates. This patent covers these compounds exemplify that these compounds have excellent contact and foliar activity; It is silent about any activity it has against insects.

European Patent Application Publication No. 10879 AI is for perhaloalkyl and nylcyclo Fluorinated phenylmethyl esters with propanecarboxylic acids, especially tetrahalogens. Lophenyl and pentahalophenyl esters clarified as “fumigated insecticides” I have to. This application discloses the use of compounds for the control of soil insects. of tetrahalophenylmethyl and pentahalophenylmethyl compounds. It has proven its effectiveness. However, the mono- or difluorophenyl methylation of the present invention The data reported here for compounds indicate that these compounds survive their larval stages in soil. Diabrotica balteata (Diabrotica balteata), a rootworm that spends a lot of time ica balteata). .

U.S. Patent Application No. 589,622, filed March 14, 1984, is 2.4.6-) Lifluorophenylmethyl 3.(2-chloro -3,3,3-)lifluoro-1-propenyl)・2,2-dimethylcyclopro The use of pancarboxylate is disclosed, but along with the European patent application mentioned above. That disclosure discloses that the mono- or difluorophenyl methyl esters of the present invention are This does not suggest to the person skilled in the art a significantly higher activity against soil insects.

The above-mentioned European patent encompasses the claims of U.S. Pat. No. 4,332,815. Certain cis-3-(2-chloro-3,3,3-tri- Fluoro-1-propenyl)-2゜2-dimethylcyclopropanecarboxylate 2-fluorophenylmethyl and 2,6-cyfluorophenylmethyl Ester compounds are found in the southern corn rootworm (Diabrotica un). Dekuinbunktata・Yatsudi　°　°°°) It has now been discovered that eel exhibits amazing activity against soil insects.

According to the above, the present invention provides a method for controlling soil insects, and this method Add 1 million parts by weight of soil to the soil where plants are or will be planted. from about 0.2 to about 8% of one or more compounds of the invention, especially 2-fluorophores. phenylmethyl or 2,6-cyfluorophenylmethyl 3-(2-chloro-3,3 ,3-)lifluoro-1-propenyl)-2,2-dimethylcyclopropancar including applying boxylate.

These compounds have the general structure shown in the formula ■ (in the formula, n is 1 or 2) .

Accordingly, the compounds used in the present invention and certain intermediates thereof may have cis and trans configurations. It exists as chemical isomers, and the carboxy and 3-positions of the cyclopropane ring The substituted vinyl groups are cis or trans with respect to each other. *a of such compounds is It usually produces a mixture of cis and trans isomers, called cis and trans; The ratio of transformers to transformers can vary over a wide range.

Since the 1 and 3 positions of the cyclopropane ring are asymmetric carbon atoms, there are 4 optical isomers. They are named IR lance IS cis, IR) lance, and Is) lance.

The compounds of the present invention have a substituent on the α-carbon of the vinyl group and a substituent on the β-carbon of the vinyl group. Depending on the spatial relationship with the substituents, E or Z isomers, or E, designated as E, Z and 2 isomeric mixtures.

Significant differences in the level of insecticidal activity between the cis and trans isomers indicate that Known for its chloropropane carboxylate technology. A given synthetic cyclopropyl As between cis and trans isomers of carboxylates, cis isomers are always is often more active than trans, and more active than cis, trans mixtures. It is active.

Similar activity differences may occur for the E and 2 isomers.

Unless a contrary intention is expressed, the present invention covers the l- and 3- The carboxy and substituted vinyl groups at the - position are mutually cis or trans, or cis and to It exemplifies and includes all compounds that are a mixture of lance configurations, and cis configurations. Similarly, the individual E and Z isomers are generally preferred, especially the IR lance isomers. as well as mixtures are also contemplated within the scope of this invention.

The compounds are described in U.S. Pat. No. 4,332, which is incorporated herein by reference. , 815, by various methods known to those skilled in the art, including those described in It is made by

A convenient method for preparing compounds of the following formula is compound C, where R is hydroxy, lower alkoxy or halogen], 2-fluorobenzyl or 2,6-cyfluoro Reactions with compounds containing benzyl alcohol residues, e.g. Sometimes by reaction with the alcohol itself.

Compound v! J2-Fluorophenylmenarcissu-3-(2-chloro-3,3,3- ) Lifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxy The rate (compound A) was obtained as an oil.

The NMR spectrum was consistent with the assigned structure. δ(COCl5=TMS) 1.32 (s-68) + 2.08 (te 2H), 5.21 (s, 2H) .

6.83-7.63 (■, 5H).

Analysis: C111H15CIF402: Calculation M: C54, 81, H4, 28 Measured value: C55,06, H4,53 Compound 2,6-cyfluorophenylmenarcissu-3-(2-chloro-3,3,3 -trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxy The sylate (compound B) was obtained as an oil.

The NMR spectrum was consistent with the specified structure* (CDCI317MS) 1 ．． 28 (S, 6H), 2.04 (t, 2H), 5.24 (S, 2 H), 6.731.56 (m, 4H).

Analysis: Cl6HI4CIF502 Calculation f! : C52,12; H3,8 3 Measured value: C52,76; H4,10 In the method of the present invention, the active compound is applied. To do this, apply the prescription to the soil where crops are planted or will be planted, i.e. Contaminates areas where insect damage occurs. This involves spraying a prescription drug on the planting area or its planned area. or the root zone of the area where the crop is planted or will be planted. This is achieved by When using the latter method, an insecticidal effective concentration of the active ingredient is A sufficient amount of the formulation must be applied to the root zone to supply the soil. It will be obvious that the usage rate suitable for this purpose is between o, i and about 5 kg/ha, preferably in the range of 0.2 to 1.5 kg/ha.

Typical formulations used in the method of the invention include the active ingredients in an agriculturally acceptable carrier. body or filler, preferably in combination with a surfactant, and optionally other active ingredients. Contain things. Suitable formulations include granules of various sizes, powders, wettable powders, and concentrated emulsions. , solutions, dispersants, etc., and their selection depends on the environmental factors of the location where insect damage occurs and the selected application. Varies depending on usage. Typical formulations include 9, excipients and carriers used, and Depending on the mode of application, the active ingredient concentration varies over a wide range. Therefore, the active ingredient is a prescription drug. It may be present in a concentration of 0.1z to 99.5% by weight. Agriculturally acceptable carrier can be contained in the formulation from about 99.5χ to about 0.5wt2. compatible table If surfactants are used in the formulation, they should be added appropriately to the I! or 30 It may be present in various concentrations ranging from weight 2.

Use the formulation as is or add a suitable diluted product to facilitate dispersion of the active ingredient. Dilute with diluent or carrier to desired working dilution. Active ingredient concentration at application dilution ranges from about 0.0001 to about 10% by weight, with lower concentrations when the diluent is water. Concentrations are particularly useful.

Compounds of the present invention are described by G.R. Sala, Inc., which is incorporated herein by reference. G, R, 5utter, J, Ec.

In the general method of Entoi, Vol. 75(3), pp. 489-91 (1982) Third instar corn rootworm larvae were subjected to filter paper test and mixed with soil. It was tested for activity against.

Example I L section x1 In the filter paper test, when the compound of the invention is dissolved in acetone/water, A test solution containing the test chemicals was obtained. Use of 100 m + w x 15 mm Place filter paper with a diameter of 100 mm in 9 disposable plastic pots, and add 2.5 mm of test liquid. 1 was poured onto filter paper. After excess water has evaporated (1-1,5 hours), wet filter paper Third or fourth instar larvae were placed on top and the Petri dish was covered. for each compound The test was conducted in duplicate. 24 hours after introducing the larvae, the larvae are dead or dying. The insecticidal rate was determined by counting the number of larvae. The results are shown in Table 1. paper exam A 90 100 2F 8 100 100 2F, 6F C90953F 0 65 30 4F 2 100 100 2F, 4F F　100　100　2F, 5F G95 100 3F, 4F a) Southern corn root worm (Diabrotica undequinbuncta) Data Holdi Diabroticound & Cimpunctata h owardi) b) Pan-dead cucumber beetle striped cucumber beetle (b) anded cucumber beetle, Diabrotica baltea Diabrotica balteata) C) Compound H is 2,4,6-do Lifluorophenylmenarcissu-3-(2-chloro-3,3,3-)lifluoro -1-propenyl)-2,2-dimethylcyclopropanecarboxylate, U.S. Patent Application No. 589, 622 filed March 14, 1984 It's hardware.

Table 1 shows two types of compounds of the present invention that spend their larval stage in the soil at a low concentration of 100%. It has been shown to be effective in killing the larvae of different insect species. of these species There was no activity at substantially higher concentrations than in European Patent Application Publication No. These results were particularly unexpected in light of the report in No. 10879 AI.

911 x1 The stock solution of each test compound was prepared by dissolving 4.8 vaz in acetone 101 and adding acetone/ It was prepared by diluting it with 90 ml of water (1:9).

5 of this stock solution in 30 g of air-dried clay loam in a 3-ounce plastic cup. The addition of 1 provides 8 ppo+ of the test compound in the soil. Serial dilution of stock solution 4.2.1.0.5.0.25 and 0.125 of the test compound in soil The concentration in ppm was obtained. In either case, 30 g of soil is mixed with liquid 51 having the required concentration. added to. Place the treated soil in the hood, uncovered, to allow the acetone to evaporate. The mixture was left for 0.5 hour.

The soil was thoroughly mixed before releasing Southern corn rootworm larvae into the soil.

Two 3-day-old corn sprouts (corn 5 sprouts) larvae and their third stage. 10 early stage (9-10 days old) southern corn rootworm larvae in a cup and stored in a sealed plastic bag with a plastic lid. 74 After storing for 48 hours at -78″F (23.3–25.6°C), remove the cup from the plastic Remove from the bag, remove the cover, and strain the contents of each cup through an 18-mesh sieve. The mortality rate of the larvae was measured by placing them in a modified Burlys polyethylene funnel. Ta. The funnel was placed over a container of aqueous detergent solution. Soil test with incandescent light (100 watts) It was placed 36 cm above the plate.

The heat from these lights dries the soil, and larvae unaffected by the test compound will It came out of the soil and fell into the detergent solution. Larvae that do not emerge are dead. It was determined that Mortality was determined in this manner for each concentration. each concentration and were also tested in duplicate.

The results of soil contamination tests may be affected by factors that cannot be controlled, such as the exact development of the larvae used in the test. Contains no active ingredients as there may be some variation from day to day due to health conditions In addition to a blank test using only insects, a control compound effective against soil insects was added to each soil test. included. Enter the original data of each compound into the computer and perform a blank test using the program. The zero-order test compound corrected for and calculated the LC5fi of the compound in that test. The class was compared to a reference standard from the same study to determine relative potency. Relative potency (RP) is It is defined as the ratio of the LCso of the control compound to the LCso of the test compound. This way In this way, compounds evaluated at different times can be compared accurately.

Table 2 demonstrates the efficacy of certain compounds of the invention and also provides information on determining relative potency. It shows.

The test results recorded in Table 2 show that Compounds A and B were It has an unexpectedly high initial activity level against root worms and It is significantly more effective against southern corn rootworm than Oro analogs. Which indicates that.

Table 2 Fluorophenylmenarcissus 3-(2-chloro-3゜3.3-tri Fluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate Soil insecticidal activity of southern corn rootworms 1 and J Layout and ML phantom I elbow FtL] I ■ [lI note! 4, Oppm 100-95- to.

2.0 85 90 95 too 85 851.0 75 80 90 9 5 85 750.5 To 75 85 60 TO700, 2565458 5402540 0,125-35-10-35 LCso (ppm) 0.27 0.38 0.14 0.450.4 0.3 T-ya- *) The control compound is (2-methyl[l,1″-biphenyl]-3-yl)methyl cis-3-(2-chloro-3,313-)lifluoro-l-bropenyl)-2, 2-dimethylcyclopropanecarboxylate.

The relative potency of mono- and difluorophenyl methyl esters is shown in Table 3.

No. L Table 1 Control compound 1 a〉Diabrotica undequinbunctata hawadi.

b) In Ei', 3-(2-chloro-3,3,3-trifluoro-1-propenylate) The cis/trans ratio of -2,2-dimethylcyclopropanecarboxylate is It is 75/25. B contains more than 98% cis isomer.

Other soil insects that can be controlled by the compounds of the present invention include: Ma Popillia japonica (Bobilia japonica Newman) ca Newan), Black Cutworm (Agelothiis epsilon A) grotisipsilon), Oregon wireworm (Melanotus ole) Melanotus oregonensis), corn wirewort (Melanotus communis coa + munis).

Gulf wireworm (Conoderus ambricoris) plicollis), Southern Potato Wireworm (Conodelus) 7sC onoderus fallD, and Braley Grain Wireworm (Quick). Ctenicera aeripenn i destructor) *International search report

Claims (6)

[Claims] 1. Add mono- or diphenyl to the soil where plants are or will be planted. fluorophenylmethyl 3-(2-chloro-3,3,3-trifluoro-1-bro from the group consisting of (benyl)-2,2-dimethylcyclobrobancarboxylates control of soil insects comprising applying an insecticidal effective amount of one or more selected compounds; division. 2. The carboxylate is fluorophenyl methyl alcohol or 2,6-di The claimed invention is an ester of fluorophenyl methyl alcohol. The method described in Scope No. 1. 3. The compound is 2-fluorophenylmethyl 3-(2-chloro-3,3,3-tri Fluoro-1-brobenyl)-2,2-dimethylcyclobrobancarboxylate 3. The method according to claim 2, characterized in that: 4. The active ingredient is 2,6-difluorophenylmethyl 3-(2-chloro-3,3, 3-trifluoro-1-brobenyl)-2,2-dimethylcyclobrobancarbo The method according to claim 1, characterized in that it is a xylate. 5. Predominantly cis or predominantly 1R, cis isomer of the active ingredient, or mixtures thereof Method according to claim 1, characterized in that it is used. 6. A claim characterized in that the active ingredient is applied at a rate of 0.1 to 5 kg/ha. The method described in item 1 of the scope of the request.