Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

• This invention pertains to the general field of insecticides and relates particularly to a method for controlling soil-borne insects, especially those insects, such as southern corn rootworm, which spend a major portion of their larval life in the soil, i.e., soil-borne insects, by applying to the soil certain fluorinated phenylmethyl esters of 3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2-dimeth lcyclopropanecar- boxylic acid.
• U.S. Patent 4,332,815 discloses a broad class of perhaloalkylvinylcyclopropanecarboxylates described as having excellent insecticidal activity against Lepidoptera and Homoptera. The patent illustrates that these compounds have superior contact and foliar activity, but is silent as to any activity these com ⁇ pounds may have against soil-borne insects.
• European Patent Application, publication number 10879 Al, discloses certain fluorinated phenylmethyl esters, especially tetrahalophenyl and pentahalo- phenyl, of perhaloalkylvinylcyclopropanecarboxylic acids as "fumigant insecticides.”
• the application discloses the use of the compounds for control of soil insects and demonstrates efficacy of tetrahalophenyl- methyl and pentahalophenylmethyl compounds.
• the data reported for the mono- or difluorophenyl- methyl compounds of the present invention show these compounds essentially inactive against Diabrotica balteata, a rootworm which spends its larval life in soil.
• this invention provides a method for controlling soil-borne insects which comprises applying to the soil in which plants • are or are about to be planted from about 0.2 to about 8 parts by weight of one or more compounds of this invention, especially 2-fluorophenylmethyl or 2,6-di- fluorophenylmethyl 3-(2-chloro-3,3,3-trifluoro-1-pro- penyl)-2,2-dimethylcyclopropanecarboxylate, per million parts by weight of soil.
• the compounds employed in this invention and cer ⁇ tain intermediates therefore exist as cis and trans geometrical isomers, the carboxy and the substituted vinyl groups at the 1- and 3-positions of the cyclo- propane ring are either cis or trans with respect to each other.
• Preparation of such compounds will usually yield a mixture of cis and trans isomers, designated cis,trans, in which the ratio of cis to trans may vary over a wide range.
• positions 1 and 3 of the cyclopropane ring are asymmetric carbon atoms, there are also 4 optical isomers which may be designated 1R, cis; IS, cis; 1R, trans; and IS, trans.
• the compounds of this invention may also exist as E or Z isomers or as mixtures of E and Z isomers, designated E, Z, depending on the spatial relationship of substituents on the -carbon of the vinyl group to those on the ⁇ -carbon of the vinyl group.
• the inven ⁇ tion embodies and includes all compounds in which the carboxy and substituted vinyl groups at the 1- and
• 3-positions of the cyclopropane ring are cis or trans, or a mixture of cis and trans configuration with respect to each other; the cis isomers, particularly the lR,cis isomers are generally preferred. Similarly, the individual E and Z isomers, as well as the mixtures, are also contemplated by and within the scope of the present invention.
• the compounds may be prepared by various methods known to those skilled in the art including those described in U.S. Patent 4,332,815, incorporated here ⁇ in by reference.
• a convenient method for preparing the compounds is from a compound of formula II
• the active com ⁇ pound is applied by incorporating a formulation there ⁇ of into the soil in which agricultural crops have been or will be planted, that is, the locus of infesta- tion. This may be achieved by broadcasting the formu ⁇ lation over the planted area or the area to be planted or by banding the application in the root zone where plants have been or are to be planted. It will be readily apparent where the latter method is employed that an amount of formulation sufficient to supply an insecticidally effective concentration of active ingredient in the soil must be applied to the root zone.
• a suitable use rate for this purpose is in the range of 0.1 to about 5 kg/ha of active ingredient, preferably 0.2 to 1.5 kg/ha.
• Typical formulations for use in the method ⁇ f the invention include the active ingredient in combination with an agriculturally acceptable carrier or extender, preferably with a surface active agent, and optionally with other active ingredients.
• Suitable formulations include granules of various sizes, dusts, wettable powders, emulsifiable concentrates, solutions, disper ⁇ sions, and the like, with the choice depending upon the environmental factors at the situs of infestation and the method of application selected.
• a typical formulation may vary widely in concentration of the active ingredient depending upon the additives and carriers used and the desired mode of application. Thus active ingredient may be present at a concen- tration of 0.1% to 99.5% by weight of the formula- tion.
• An agriculturally acceptable carrier may com ⁇ prise about 99.5% by weight to as low as 0.5% by weight of the formulation.
• Compatible surface active agents if employed in the formulation, may be present at various concentrations, suitably in the range of 1% to 30% by weight of the formulation.
• the formulation may be used as such or diluted to a desired use dilution with a diluent or carrier suit ⁇ able for facilitating dispersion of the active ingre- dominant.
• concentration of the active ingredient in dilution for the application may be in the range of about 0.0001 to about 10% by weight, with lower con ⁇ centrations particularly useful when the diluent is water.
• the compounds of the invention were subjected to a filter paper test and also were incorporated in soil and tested for activity against third instar southern corn rootworm larvae by the general method of G. R. Sutter, J. Econ. Entom. , Vol 75(3), 4 * 89-91 (1982), incorporated herein by reference.
• EXAMPLE 1 Filter Paper Test In the filter paper test a compound of the inven ⁇ tion was dissolved in acetone/water to give a test solution containing the specified concentration of test chemical. A 100 mm diameter filter paper was placed in a disposable, plastic, 100 mm x 15 mm petri dish and 2.5 ml of the test solution was poured onto the filter paper. After excess water had evaporated (1 - 1.5 hours), ten 3rd or 4th instar larvae were placed on the damp filter paper and the petri dish was covered. Two replicates of the test were carried out for each compound. Twenty-four hours after infesta ⁇ tion the dead and moribund larvae were counted, and percent kill was determined. Results are reported in Table 1. TABLE 1
• Table 1 shows that at the low concentration of 1 part per million the compounds of this invention are effective in killing the larvae of two different insect species that spend their larval life in the soil.
• Soil Incorporation Test A stock solution of each test compound was pre ⁇ pared by dissolving 4.8 mg in 10 ml of acetone and diluting with 90 ml of acetone/water (1:9). The addi ⁇ tion of -5 ml of this stock solution to 30 g of air- dried, clay loam soil in a 3-oz plastic cup provided a concentration of 8 ppm of the test compound in the soil. Serial dilution of the stock solution was used to obtain concentrations of the test compound in soil of 4, 2, 1, 0.5, 0.25, and 0.125 ppm. In all cases 5 ml of a solution having the required concentration was added to 30 g of soil.
• the treated soil was allowed to stand uncovered in a hood for 0.5 hour to evaporate the acetone. Before infesting the soil with southern corn rootworm larvae, the soil was mixed thoroughly. Two three-day-old corn sprouts and ten early third-stage (9-10 days old) southern corn root- worm larvae were placed in the cup which was then covered with a plastic lid, and held in a closed plastic bag. After storage at 74-78°F for 48 hours, the mortality of the larvae was determined by removing the cup from the plastic bag, removing the cover, and placing the contents of each cup in a modified Berlese polyethylene funnel fitted with an 18-mesh screen. The funnels were placed over containers of an aqueous detergent solution.
• Incandescent lights (100 watts) were placed 36 cm above the soil samples. The heat from these lights slowly dried the soil which caused larvae that had not been affected by the test compound to emerge from the soil and drop into the detergent solution. Larvae that did not emerge were judged to be dead. The percent mortality was determined in this manner for each concentration. Duplicate tests were run at each concentration. Since the results of the soil incorporation test may differ somewhat from day to day owing to factors which cannot be controlled, e.g. the precise develop- ment and state of health of the larvae used in the test, a reference compound effective against soil insects is included in each soil incorporation test, as is a blank with insects, but no active ingredient.
• RP Relative potency
• Table 2 demonstrates the effi- cacy of certain compounds of this invention and also illustrates determination of relative potency.
• the reference compound is ( 2-methyl [ 1, 1 ⁇ -biphenyl ]-3- yl)methyl cis-3-(2-chloro-3, 3,3-trifluoro-l-pro- penyl)-2, 2-dimethylc clopropanecarboxylate.
• the relative potencies of the mono- and difluoro- phenylmethyl esters of this invention are presented in Table 3.
• soil-borne insects that may be controlled by the compounds of the invention include: Japanese beetle (Popillia japonica Newman) , black cutworm (Agrotis ipsilon) , Oregon wireworm (Melanotus oregonensis) , corn wireworm (Melanotus communis) , Gulf wireworm (Conoderus amplicollis) , southern potato wireworm (Conoderus falli), and Prairie grain wireworm (Ctenicera aeripenni destructor) .

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Dentistry (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Toxicology (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1985
  • 1985-10-01 BR BR8506967A patent/BR8506967A/pt unknown
  • 1985-10-01 HU HU855033A patent/HUT41236A/hu unknown
  • 1985-10-01 WO PCT/US1985/001898 patent/WO1986002238A1/en not_active Application Discontinuation
  • 1985-10-01 EP EP19850905156 patent/EP0197115A4/de not_active Withdrawn
  • 1985-10-01 AU AU49525/85A patent/AU564889B2/en not_active Ceased
  • 1985-10-01 JP JP60504542A patent/JPS61501709A/ja active Pending
  • 1985-10-06 IL IL76595A patent/IL76595A/xx unknown
  • 1985-10-08 GR GR852434A patent/GR852434B/el unknown
  • 1985-10-08 AR AR85301877A patent/AR247656A1/es active
  • 1985-10-08 CN CN85107462A patent/CN1009417B/zh not_active Expired
• 1986
  • 1986-06-09 BG BG075271A patent/BG51231A3/bg unknown
  • 1986-06-09 DK DK269286A patent/DK269286D0/da not_active Application Discontinuation
  • 1986-06-10 KR KR1019860700343A patent/KR870700285A/ko not_active Application Discontinuation

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