MX2008008174A - Insecticidal and miticidal mixtures of bifenthrin and cyano-pyrethroids - Google Patents
Insecticidal and miticidal mixtures of bifenthrin and cyano-pyrethroidsInfo
- Publication number
- MX2008008174A MX2008008174A MXMX/A/2008/008174A MX2008008174A MX2008008174A MX 2008008174 A MX2008008174 A MX 2008008174A MX 2008008174 A MX2008008174 A MX 2008008174A MX 2008008174 A MX2008008174 A MX 2008008174A
- Authority
- MX
- Mexico
- Prior art keywords
- cyano
- cypermethrin
- bifenthrin
- insecticidal
- insects
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 230000000749 insecticidal Effects 0.000 title claims abstract description 71
- 239000005874 Bifenthrin Substances 0.000 title claims abstract description 37
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 title claims abstract description 37
- 230000003129 miticidal Effects 0.000 title claims abstract description 4
- 239000002728 pyrethroid Substances 0.000 claims abstract description 18
- 241000238631 Hexapoda Species 0.000 claims description 40
- 239000005946 Cypermethrin Substances 0.000 claims description 24
- KAATUXNTWXVJKI-UHFFFAOYSA-N Cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 14
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 10
- -1 tralometrine Chemical compound 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 6
- 239000005895 Esfenvalerate Substances 0.000 claims description 5
- 230000000240 adjuvant Effects 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 5
- 229960005424 cypermethrin Drugs 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000005892 Deltamethrin Substances 0.000 claims description 3
- OWZREIFADZCYQD-NSHGMRRFSA-N Deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 3
- 229960002483 decamethrin Drugs 0.000 claims description 3
- QQODLKZGRKWIFG-QSFXBCCZSA-N Cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 2
- FJDPATXIBIBRIM-UHFFFAOYSA-N Cyphenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-UHFFFAOYSA-N 0.000 claims description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N Fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 2
- INISTDXBRIBGOC-UHFFFAOYSA-N Fluvalinate Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C(C(C)C)NC1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-UHFFFAOYSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-BWHPXCRDSA-N [cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-BWHPXCRDSA-N 0.000 claims description 2
- 230000003197 catalytic Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229960001591 cyfluthrin Drugs 0.000 claims description 2
- 239000001187 sodium carbonate Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 claims 1
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- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention is directed to novel insecticidal and/or miticidal compositions comprising bifenthrin and a cyano-pyrethroid. The compositions exhibit an unexpected increase in insecticidal activity as compared to the insecticidal activity of the individual components.
Description
INSECTICIDES AND MYTICIDES OF BIFENTRI N A AND CYANO-PIRETROIDES
FIELD OF THE INVENTION The present invention relates to the field of insecticides. In particular, the invention provides novel insecticidal compositions comprising bifenthrin and cyano-pyrethroids that exhibit unexpected insecticidal activity. BACKGROUND OF THE INVENTION It is well known that insects in general can cause significant damage, not only to crops grown in agriculture, but also, for example, to structures and grass where the damage is caused by insects that are born in the soil, such as termites and white larvae. Such damage can result in the loss of millions of dollars of value related to the established crop, turf or structure. Insecticides and acaricides are useful for controlling insects and mites, which, distinctly, would cause significant damage to crops, such as wheat, corn, soybeans, potatoes and cotton to name a few. For the protection of the crop it is desirable to use effective chemical insecticides and acaricides, which can control insects and mites without damaging the crops, and which have no harmful effects for mammals and other living organisms. For commercial agricultural use, it would be beneficial to combine insecticides that have different spectra of activity and
residual effectiveness to take advantage of each individual insecticide property. Mixtures containing two or more insecticides have been practiced in the art to benefit the insecticidal properties of the individual components. For example, US Patent 3,899,586 discloses an insecticidal and / or acaricidal composition obtained by mixing N- (3,4,5,6-tetrahydrophthalimide) -methyl chrysanthemate with 3- (2,2-dichlorovinyl) -2.2 5- (2-propynyl) furfuryl dimethylcyclopropanecarboxylate. Brief Description of the Invention In accordance with the present invention, it has been found that a novel insecticidal composition comprising bifenthrin and a cyano-pyrethroid shows an unexpected increase in insecticidal activity as compared to the insecticidal activity of the individual components. The present invention is also directed to a novel insecticidal composition comprising bifenthrin and a cyano-pyrethroid in admixture with at least one expander acceptable for agriculture or adjuvant. Detailed Description of the Invention In accordance with the present invention, it has been found that a novel insecticidal composition containing bifenthrin and a cyano-pyrethroid exhibits an unexpected increase in insecticidal activity as compared to the insecticidal activity of the individual components. The present invention is also directed to a novel insecticidal composition comprising
bifenthrin and a cyano-pyrethroid in admixture with at least one expander or adjuvant acceptable for agriculture. Synthetic pyrethroids that contain a cyano group (cyano-pyrethroids) are very potent insecticides, for example, zera-cypermethrin is an insecticide that acts in a potent and rapid way, which controls a large spectrum of chewing, sucking and flying insects. In addition to chewing, sucking and flying insects, pyrethroid bifenthrin is also active against a number of key mite pests and shows a longer residual activity than zeta-cypermethrin. It has now been discovered that by combining these two potent insecticides, an unexpected increase in insecticidal activity is observed in some insect species. In addition to being very potent insecticides that act quickly, cyano-pyrethroids often cause skin irritation in mammals. By using a mixture containing less bifenthrin and less cyano-pyrethroid to obtain superior insecticidal activity for the insecticide compound alone, an ecological benefit and for the safety of mammals is realized. Specifically, one aspect of the present invention is directed to an insecticidal composition comprising bifenthrin and a cyano-pyrethroid. Another aspect of the present invention is directed to an insecticidal composition comprising bifenthrin and a cyanopyrethroid, in admixture with at least one extender or adjuvant.
acceptable in agriculture. Another aspect of the present invention relates to methods for controlling insects by applying an insect-effective amount of a composition as set forth in a location of crops such as, without limitation, cereals, cotton, vegetables, and fruits, or other areas in where the insects are present or are expected to be present. The term "bifenthrin" means 2-methylbiphenyl-3-ylmethyl (Z) - (1 RS) -c / 's-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2-cyclopropanecarboxylate , 2-dimethyl. The term "cyano-pyrethroid" means an insecticide pyrethroid containing a cyano group. The cyano-pyrethroid is selected from the group consisting of, but is not limited to: acrinatrin which is (S) -a-cyano-3-phenoxybenzyl (Z) - (1 R) -c / 's-2,2 -dimethyl-3- [2- (2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl) vinyl] cyclopropanecarboxylate, cycloprotrine, which is (RS) -a-cyano-3-phenoxybenzyl (RS) -2,2-dichloro -1 - (4-ethoxyphene) cyclop clothing noca rboxi lato], deltamethrin [(S) -a-cyano-3-phenoxybenzyl (1 R) -c s-3- (2,2-dibromovinil) -2,2 -dimethylcyclopropanecarboxylate, tralometrine, which is (S) -a-cyano-3-phenoxybenzyl (1R) -c / 's-2,2-dimethyl-3 - [(RS) -1, 2, 2,2- tetrabromoethyl] cyclopropanoca rboxi lato, fenvalerate, which is (RS) -a-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate, cyfluthrin, which is (RS) -a- cyano-4-fluoro-3-
phenoxybenzyl (1 RS) -c s-frans-3- (2,2-dichlorovinyl) -2,2-dimethylcycloprocarboxylate, beía-cyfluthrin, which is a reaction mixture comprising the enantiomeric pair (R) -a- cyano-4-fluoro-3-phenoxybenzyl (1S) -c / 's-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and (S) -a-cyano-4-fluoro-3-phenoxybenzyl (1 R) -c / s-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate in a range of 1: 2 with the enantiomeric (R) -acyano-4-fluoro-3-phenoxybenzyl couple (1 S) -trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and (S) -acyano-4-fluoro-3-phenoxybenzyl (1R) -rrans-3- (2, 2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate flucytrinate, which is (RS) -a-cyano-3-phenoxybenzyl (S) -2- (4-difluoromethoxyphenyl) -3-methylbutyrate, a / fa-cypermethrin, which is a racemate comprising (S) -a-cyano-3-phenoxybenzyl (1 R) -c s-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and (R) -a-cyano-3- phenoxybenzyl (1 S) -c / 's-3- (2,2-dichloro inyl) -2,2-dimethylcyclopropanecarboxylate, oera-cypermetr ina, which is a reaction mixture comprising two enantiomeric pairs in a range of about 2: 3 (S) -acyano-3-phenoxybenzyl (1 R) -c s-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and (R) -a -cyano.-3-phenoxybenzyl (15) -c / 's-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate with (S) -a -cyano-3-phenoxybenzyl (1R) -frans-3- (2,2-dichloro-ynyl) -2,2-dimethylcyclopropanecarboxylate and (R) -
acyano-3-phenoxybenzyl (1S) - tra ns-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, phthaefa-cypermethrin, which is a mixture of 1: 1 of enantiomers (R) -acyano-3-phenoxybenzyl (1S) -frans-3- (2,2-dirchlorovinyl) -2,2-dimethylcyclopropanecarboxylate and (S) -a-cyano-3 -phenoxybenzyl (1R) -rnes-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, zeta-cypermethrin, which is (R, S) -a-cyano-3-phenoxybenzyl- (1 RS) -c / 's-fra / 7s-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, which was enriched in the isomers 1R-cis-S and 1R-trans-S, cyphenothrin, the which is (R, S) -a-cyano-3-phenoxybenzyl- (1 R) -c / 's-frans-2,2-dimethyl-3- (2-methylprop-1-enyl) -cyclopropanecarboxylate, cyhalothrin, which is (R, S) -a-cyano-3-phenoxybenzyl- (Z) - (1 RS) -c / s -3- (2-chloro-3,3,3-trifluoropropentyl) -2,2-dimethylcyclopropanecarboxylate , / amfada-cyhalothrin, which is a reaction product that comprises equal amounts of (S) -a-cyano-3-phenoxybenzyl- (Z) - (1 R) -c s-3- (2-chloro-3 , 3,3-trifluorophenyl) - 2) 2-dimethylcyclopropanecarboxylate and (R) -acyano-3-phenoxybenzyl- (Z) - (1S) -c / 's-3- (2-chloro-3,3,3-trifluoropropenyl) -2, 2- dimethylcyclopropanecarboxylate, esfenvalerate, which is (S) -acyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate, fluvalinate, which is CRSJ-α-cyano-3-phenoxybenzyl N- (2-
chloro-a, a, a-trifluoro-p-tolyl) -DL-valine, and fenpropatrine, which is (f? SJ-a-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate. Particular form of zera-cypermethrin is (RS) -a-cyano-3-phenoxybenzyl- (1 RS) -c / 's-frans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, which has has been enriched in the 1R-c / sS and 1R-rrans-S isomers by the processes described in U.S. Patent Nos. 5,164,411; 5,028,731 and 4,997, 970. A more preferred form of zera-cypermethrin is the mixture of isomer prepared by the process described in U.S. Patent No. 4,997,970 which begins with a cis / trans mixture of cypermethrin with a catalytic amount of tricaprylammonium chloride (Aliquat®336, Aldrich Chemical Co.) and sodium carbonate in n-heptane. Subsequent isolation procedure produces zeta-cypermethrin which contains a small amount, usually 0.6% to 1.3% of the catalyst.The range of active ingredient of bifent rina (Al, for its acronym in English) to cyano-pyrethroid Al can be from 1/99 to 99/1. Preferably the range of bifenthrin Al to cyano-pyrethroid Al is from 1/4 to 4/1 .. More preferably the range is from 1/3 to 3/1. The present composition is effective against various insect pests and / or mite plates. Pests of insects and mites to which the present invention is applied are: Homoptera, which includes, for example, aphids, grasshoppers,
cicadas, white flies and woodlice; Lepidoptera, which includes, for example, butterflies, moths and green flies; Coleoptera, which includes, for example, beetles and weevils; and Acariña, which includes, for example, mites and ticks. The insecticidal compositions can be applied either aerosol diluted with water, or powders, or granules to the areas in which the suppression of insects is desired. These formulations may contain at least 0.1%, 0.1% or 0.5% and at most 95% or more by weight of active ingredient. Powders are active ingredient mixtures that flow freely with finely divided solids such as talc, natural clays, diatoms, flours such as walnut shells and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for toxics.; these finely divided solids have an average particle size of at least 50 microns. A typical typical powder formulation is one that contains 1.0 parts or less of the insecticidal compound and 99.0 parts of talc. The humidifying powders, as well as useful formulations for insecticides, are in the form of finely divided particles which are easily dispersed in water or other dispersant. Humidifier dust is ultimately applied to the place where insect control is needed either as a dry powder or as an emulsion in water or another liquid. Typical carriers for humidifying powders include Fuller's earth, clays
bailona, silicas and other high adsorbents, humid inorganic diluents easily. Humidifying powders are usually prepared to contain about 5-80% active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of humidifying, dispersing and emulsifying agent to facilitate dispersion. For example, a useful humidifying powder formulation contains 80.0 parts of insecticidal compound, 17.9 parts of Palmetto clay and 1.0 parts of sodium lignosulfonate and 0.3 parts of sulfonated aliphatic polyester as humidifying agents. The humidifying agent and / or oil would often be added to a tank mix to facilitate foliar dispersion of the plants. Other useful formulations for insecticidal applications are emulsified concentrates (EC), which are homogeneous liquid dispersible dispersions in water or other dispersant, and may consist entirely of an insecticidal compound and an emulsified liquid or solid agent, or may also contain a carrier liquid, such as xylene, heavy aromatic naphthas or other non-volatile organic solvents-For insecticidal application, these concentrates are dispersed in water or other liquid carrier and normally applied as an aerosol to the area to be treated. The percentage by weight of essential active ingredient may vary according to the manner in which the composition is to be applied, but in
General comprises 0.5 to 95% active ingredient per weight insecticidal composition. Fluid formulations and concentrated aqueous emulsion formulations (EW) are similar to EC, except that the active ingredient is suspended in a liquid carrier, usually water. Fluid materials, such as ECC, may include one or more surfactants, and typically contain active ingredients in the range of 0.5 to 95%, frequently from 10% to 50%, by weight of the composition. For application, the fluid materials can be diluted in water or another liquid vehicle, and are normally applied as an aerosol to the area to be treated. Typically the humidifying, dispersing and emulsifying agents used in agricultural formulations include, but are not limited to, alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyether alkylaryl alcohols; highly sulphonated alcohols, polyethylene oxides; sulphonated animal and vegetable oils; sulfonated oil; fatty acid esters of polyhydric alcohols and ethylene oxide addition products as esters; and the product of addition of long chain mercatants and ethylene oxide. Many other types of useful surface active agents are commercially available. The surface active agents, when used, usually comprise from 1 to 15% by weight of the composition.
Other useful formulations include suspensions of active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents. Still other useful formulations for insecticidal applications include simple solutions of active ingredient in a solvent in which it is completely soluble in the desired concentration, such as acetone, alkylated naphthalenes, xylene or other organic solvents. Granular formulations, in which the toxins are carried in relative ordinary particles, are of particular utility for aerial distribution or for penetration into the litter of crops covered. Pressurized aerosols, typically aerosols where the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling solvent dispersing carrier can also be used. Granules soluble in water or dissolving in water flow freely, do not contain dust, and dissolve easily in water or are miscible in water. When used by farmers on farms, granular formulations, emulsified concentrates, aqueous emulsions, solutions, etc. they can be diluted with water to obtain an active ingredient in the range of 0.1% or 0.2% to 1.5% or 2%. The insecticidal formulations may further comprise additional components such as an antifreeze agent, an antifoaming agent and / or a biocide.
The compositions of the present invention are further illustrated by the examples below. The examples serve only to illustrate the invention and should not be construed as limiting since the modifications left by this invention would be obvious to those skilled in the art. All these modifications are considered to be within the scope of the invention as defined in the claims. The term "ambient temperature" as used herein means any suitable temperature found in a laboratory or any other place of work, and is generally no more below 15 ° C and not more than 30 ° C.
EXAMPLE 1 This example illustrates a protocol for the preparation of a 2/1 range of bifenthrin to concentrate emulsified zera-cypermethrin formulation. To 42.32 grams of Aromatic 200 ND (available from ExxonMobile Chemicals) was added 8.34 grams of melted bifenthrin (95.9% active ingredient) and 11.11 grams of zefa-cypermethrin (36% active ingredient, prepared by the process described in the North American patent). 4,997,970). The mixture was stirred at room temperature with a mechanical stirrer until a homogeneous solution was formed, at the same time 2.52 grams of a branched dodecylbenzene sulfonate salt (Agnique ABS 70AE, available from Cognis Corporation), 0.28
grams of polyethylene glycol monooleate (Agnique PEG 400MO, available from Cognis Corporation), 0.84 grams of ethoxylated castor oil (Agnique CSO-36, available from Cognis Corporation), 1.96 grams of ethoxylated castor oil (Agnique CSO-25, available from Cognis Corporation), 20.00 grams of severely light refined solvent and heavy paraffinic oil (Sunspray 6N, available from Sunoco, Inc.) and 0.08 grams of acetic acid were added. When the addition is complete, stirring was continued for 10 minutes to obtain a yellowish homogeneous solution. The candidate insecticidal composition was evaluated for activity in foliar evaluations against the tobacco worm (Heliothis virescens [Fabricius]), Colorado potato beetle (Leptinotarsa decemlineata [Say]), bollworm (Helicoverpa be fBoddie) cotton aphid ( Aphis qossv] P // [Glover1) and the red common spider (Tetranychus urticae [Koch]). Each test includes controls in which the formulation or test solution minus the active ingredient were applied. In tests against the tobacco worm, the first 7 to 10 days actual leaves of cotton plant (Gossypium hirsutium) were immersed in the test solution of the test formulations to obtain application intervals such as 10 ppm of active ingredients, bifenthrin and zefa-cypermethrin (prepared by the process described in the North American patent
4,997, 970). The test formulations were dissolved in distilled water containing 10% acetone and 0.25% non-ionic detergent [an octylphenolpoly (ethylene glycol ether) x, available from Roche Applied Science as Triton X-100] at appropriate concentrations. The treated plants were transferred to a cover where they were kept until the leaves dried. Each leaf was placed in a separate plastic Petri dish (100 x 20mm), which contained a paper moistened with water. Five second stage tobacco worms were placed in a Petri dish, taking care not to cause injuries. The plastic caps were placed in each of the dishes, which were kept for 72 hours at 25 ° C, 50% relative humidity with photo period of 12 hours with light and 12 hours in darkness. At the end of 72 hours of the exhibition period, the dishes were opened, and live and dead insects were counted. The insects were classified as "dead" when they failed to right themselves when they were moved. Using the insect count, the activity of the chemical test was expressed in the percentage of control. The percentage of control is derived from the total number of dead insects (TD) compared to the total number of insects (TI) in the test:
% Control = - x 100. TI In tests with the Colorado potato beetle, the
6-8 inch tall leaves of tomato plants (Lycopersicon lycoper) were immersed in the test solutions of the test formulations to obtain application intervals as high as 1000 ppm of active ingredients. The test formulations were dissolved in distilled water containing 10% acetone and 0.25% non-ionic detergent [an octylphenol-poly (ethylene glycol ether) x, available from Roche Apllied Science as Triton X-100], for appropriate concentrations. The treated plants were transferred to a covered place where they were kept until the leaves dried. For tests in which the active ingredients were not formulated, ie the technical active ingredient was used, the solution of the test compound was stored. For example, a 100 ppm storage solution can be made by dissolving 4 milligrams of test compound in 4 ml of acetone and adding the solution to 36 ml of an aqueous Triton X-100 solution (one drop of Triton X-100 dissolved in 100 ml. of distilled water). Subsequent dilutions can be made by adding distilled water containing 10% acetone and 0.25% Triton X-100. The treated tomato plants were removed from their pots by cutting the stem just above the soil line. Each cut plant was placed in an 8 oz. Individual paper cup. Ten Colorado potato beetles were placed in each paper cup, careful not to cause
wounds An opaque plastic lid was placed in each cup, for a period of 72 hours and maintained at 25 ° C, 50% relative humidity with a photo-period of 12 light hours and 12 dark hours. At the end of the 72-hour display period, cups were opened and live and dead insects were counted. Using the count of the insects, the activity of the test chemistry was expressed in the percentage control. The percent control is derived from the total number of dead insects (TD) compared to the total number of insects (TI) in the test:
TD% Control = 100. YOU
In tests with the corn worm, a one-inch diameter leaf disc cut from cotton plant leaves (Gossipium hirsutum) were immersed in the test solutions of the test formulations to obtain application intervals as high as 1000 ppm. active ingredients. The test formulations were dissolved in distilled water containing 10% acetone and 0.25% nonionic detergent [an octylphenolpoly (ethylene glycol ether) x, available from Roche Apllied Science as Triton X-100], in appropriate concentrations. The cotton wicks, 0.5 inches in diameter by 2 inches in length, were cleaned with distilled water and placed in the wells of a 32-well tray (available from Rearing Tray
Bio-Fit 32, from C-D International, Pittman, New Jersey), one wick per well. The treated leaf discs were placed on top of the cotton wicks, one leaf disc per wick, and the back tray was brought to a covered place until the leaf discs had dried. Each disc was infested with an acorn worm of a second and third condition, replicated 16 times per application interval, and a lid was placed on the tray. The trays were kept in a growth chamber for 96 hours at 25 ° C, 50% relative humidity and a photo-period of 12 hours / 12 hours dark. For tests in which the active ingredients were not formulated, ie the technical active ingredient was used; a storage solution of the test compound was used. For example, a 100 ppm storage solution was made by dissolving 4 milligrams of the test compound in 4 ml of acetone and adding the solution to 36 ml of an aqueous Triton X-100 solution (one drop of Triton X-100 dissolved in 100 ml. of distilled water). Subsequent dilutions can be made by adding distilled water containing 10% acetone and 0.25% Triton X-100. At the end of the 96-hour display period, the tray was opened, and dead and alive insects were counted. Insects were classified as "dead" if they failed to show movement when tested. Using the insect count, the activity of the test chemicals was expressed in the
percentage control. The percent control is derived from the total number of dead insects (TD) compared to the total number of insects (TI) in the test:
% Control = - x 100. TI
In proof against the cotton aphid, the 6 to 8 inch tall leaves of tomato leaves (Lycopersicon Ivcooer) were infested with approximately 50 cotton aphids by placing leaf cuttings from a cotton aphid colony that is a host of a plant of tomato. After approximately 12 hours the newly infested tomato leaves were immersed in the test solutions of the test formulations to obtain application intervals as high as 1000 ppm of active ingredients. The test formulations were dissolved in, and diluted if necessary, with distilled water containing 10% acetone and 0.25% nonionic detergent [an octyl phenol poly (ethylene glycol ether) x, available from Roche Apllied Science as Triton X-100], in appropriate concentrations. After the treatment, a parafilm paper box was placed around the stem of each test plant, covering the soil of each pot to catch the dead aphids that fall from the plants. The treated plants were transferred to a covered place where they were kept until the leaves dried. Once dried, the plants in the pots were placed in a tray that
It contains at least one inch of water. The plants were placed too far apart to prevent aphids from moving between the plants. The trays were kept in a chamber for 72 hours at 25 ° C, 50% relative humidity and photo-period of 14 light hours / 10 hours dark. For tests in which the active ingredients were not formulated, ie the technical active ingredient was used; A storage solution of the test compound was made. For example, a 100 ppm storage solution was made by dissolving 4 milligrams of the test compound in 4 ml of acetone and adding the solution to 36 ml of Triton X-100 aqueous solution (one drop of Triton X-100 dissolved in 100 ml of distilled water). Subsequent dilutions can be made by adding distilled water containing 10% acetone and 0.25% Triton X-100. At the end of the 72-hour display period, dead and live insects were counted. The insects were classified as "dead" if they were colorless, or brown or dissected. Using the insect count, the activity of the test chemical was expressed in the percent control. The percentage control is derived from the total number of dead insects (TD) compared to the total number of insects (TI) in the test.
% Control = - x 100. TI
In tests with red spiders, the leaves of 3 to 4 inch tall pinto bean plants (Phaseolus vulgaris) were infested with approximately 50 to 75 adult red spiders by placing leaf cuttings from a common spider colony red host of a bean plant I paint on the upper surface of the leaves of the test plant. After about 1 hour, the newly infested leaves were immersed in test solutions of the test formulations to obtain application intervals as high as 1000 ppm of active ingredients. The test formulations were dissolved in, and diluted if necessary, with distilled water containing 10% acetone and 0.25% non-ionic detergent [an octylphenolpoly (ethylene glycol ether) x, available from Roche Apllied Science as Triton X-100], in appropriate concentrations. The treated plants were transferred to a covered place where they were kept until the leaves had dried. Once dried, the potted plants were placed in a tray containing at least one inch of water. The plants were placed too spaced to prevent common spiders from moving between the plants. The trays were kept in a growth chamber for 96 hours at 25 ° C, 50% relative humidity and a photo-period of 14 light hours / 10 hours dark. For tests in which the active ingredients were not formulated, ie the active technical ingredient was used; a storage solution
Test compound was elaborated. For example, a 100 ppm storage solution was made by dissolving 4 milligrams of the test compound in 4 ml of acetone and adding the solution to 36 ml of an aqueous solution Triton X-100 (one drop of Triton X-100 dissolved in 100 ml. of distilled water). Subsequent dilutions can be elaborated by adding distilled water containing 10% acetone and 0.25% Triton X-100. At the end of the 96-hour display period, numbers of dead and live insects were counted. Insects were classified as "dead" if they did not show movement when tested. Using the insect counts, the chemical activity test was expressed in percent control. The percent control is derived from the total number of dead insects (TD) compared to the total number of insects (TI) in the test:
TD% Control = - 100. TI The insecticidal activity information of the tobacco worm at selected intervals of application of this test is shown in Table 2. The information on the insecticidal activity of the Colorado potato beetle at selected intervals of application of this test is shown in Table 3. Tables 2 and 3 also contain insecticidal results from individually tested formulations of bifenthrin (Capture 2EC®, available from FMC Corporaion), and zeta-
cypermethrin (Mustang Max 0.8EC®, available from FMC Corporation) as well as the control of control test results. For all cases reported in Tables 2 and 3, the test insecticidal formulation contains,% by weight of all components in the total formulation and (grams); 15.00% (19.45 grams) bifenthrin / zera-cypermethrin (bifenthrin / zea-cypermethrin range provided in the table, 7.00% (5.60 grams) of the surfactant mixture, 25.00% (20.00 grams) of Sunspray 6N, 52.90% (42.32) grams) of Aromatic 200, and 0.10% (0.08 grams) of acetic acid The surfactant mixture comprises 3.15% (2.52 grams) of Agnique ABS70AE, 0.35% (0.28 grams) of Agnique PEG 400 MO, 1.05% (0.84 grams) of Agnique CSO-36, and 2.45% (1.96 grams) of Agnique CSO-25. The numbers in bold indicate that a beneficial insecticidal effect was observed when compared with the individual compounds.
Table 2 Tobacco worm (Heliothis virescens [Fabricus)] Insecticidal activity of Bifenthrin and zefa-cypermethrin (prepared according to the procedure described in U.S. Patent 4,997,970).
Range Concentration Concentration Percent Concentration Bifenthrin / zeta- Treatment Total bifenthrin Mortality zeta- Cypermethrin (ppm) Cypermethrin (ppm) (ppm)
Capture 1/0 10.0 0 10.0 100 2EC® Capture 1/0 5.4 0 5.4 95 2EC® Capture 1/0 3.0 0 3.0 35 2EC® Capture 1/0 1.0 0 1.0 20 2EC® Mustang Max 0/1 0 10.0 10.0 90 0.8 EC® Mustang Max 0/1 0 5.4 5.4 65 0.8EC® Mustang Max 0/1 0 3.0 3.0 40 0.8EC® Mustang Max 0/1 0 1.0 1.0 30 0.8EC® Bifen / zeia 2/1 6.7 3.3 10.0 95
Bifen / zeía. 2/1 3.6. 1.8 5.4 90
Bifen / zeía 2/1 2.0 1.0 3.0 80
Bifen / zeía 2/1 0.7 0.3 1.0 55
Bifen / zeía 1/1 5.0 5.0 10.0 90
Bifen / zeta 1/1 2.7 2.7 5.4 85
Bifen / zeía 1/1 1.5 1.5 3.0 70
Bifen / zeía 1/1 .05 .05 1.0 40
Bifen / zeía 1/2 3.3 6.7 10.0 100
Bifen / zeia 1/2 1.8 3.6 5.4 90
Bifen / zeía 1/2 1.0 2.0 3.0 75
Bifen / zeía 1/2 0.3 0.7 1.0 35
Bifen / zeía 1/3. 2.5 7.5 10.0 90
Bifen / zeta 1/3 1.4 4.1 5.4 79
Bifen / zeía 1/3 0.8 2.3 3.0 85
Bifen / zeta 1/3 0.3 0.8 1.0 65
Bifen / zeía 1/4 2.0 8.0 10.0 100
Bifen / zeía 1/4 1.1 4.3 5.4 95
Bifenzeía 1/4 0.6 2.4 3.0 85
Bifen / zeía 1/4 0.2 0.8 1.0 56 Control - 0 0 0 0
As set forth in Table 2, the bifenthrin and zera-cypermethrin test formulations in total concentrations of 3.0 ppm and slower-provided improved control of the tobacco worm when compared to the individually tested formulations of bifenthrin (Capture
2EC®, available from F C Corporation), and zefa-cypermethrin (Mustang Max 0.8EC®, available from FMC Corporation). One skilled in the art would expect blends of bifenthrin and zeta-cypermethrin, at lower than normal ranges, to exhibit insecticidal activity equivalent to the individual insecticidal compounds. At intervals of 3.0 ppm and below, the novel formulated mixture showed up to twice the insecticidal activity of the insecticidal compounds in the ranges and is within insecticidal activity of the commercially suggested ranges between 5.4 ppm and 10.0 ppm.
Table 3 Adult Colorado potato beetle (Leptinotarsa decemlineata \ Say) Insecticidal activity of bifenthrin and zeta-cypermethrin (prepared by the process described in US Patent No. 4,997,970).
Concentration Range Concentration Concentration Percentage
Treatment Bifenthrin / Bifenthrin zeta- Total Mortality zeta .. (PPm) Cipe rmethrin (ppm) Cypermethrin (ppm)
Capture 1/0 10.0 2EC® 0 10.0 35
Mustang Max 0/1 0 10.0 10.0 30 0.8EC® Bifeo / zeta 2/1 6.7 3.3 10.0 90
Bifen / zcfa 1/1 5.0 5.0 10.0 95
Bifen / zeto 1/2 3.3 6.7 10.0 70
BifenJzeta 1/3 2.5 • 7.5 10.0 70
Bifenzeta 1/4 2.0 8.0 10.0 65
Control - 0 0 0 0
As stated in Table 3, the formulations of
Bifenthrin and zeta-cypermethrin test, at a total concentration of 10.0 ppm, provided better control of the Colorado potato beetle compared to the individually tested formulations of bifenthrin (Capture 2EC®, available from FMC Corporation) and zefa-cypermethrin (Mustang Max 0.8EC®, available from FMC Corporation). One skilled in the art would expect the mixture of bifenthrin and zeta-cypermethrin to exhibit the equivalent insecticidal activity with the individual insecticidal compounds. In the tested ranges of 10.0 ppm, the insecticidal activity of the novel formulated mixture exhibited two or three times of insecticidal activity of the individual insecticidal compounds.
The Colorado Colorado potato beetle activity information at selected application intervals in which the technical active ingredients were not formulated but were dissolved as described above is provided in Table 4. The numbers in bold and italic indicated that A beneficial insecticidal effect was observed when compared with the individual compounds.
Table 4 Adult Colorado potato beetle (Leptinotarsa decemlineata [Say]), Insecticidal activity of Bifenthrin and Cyano-pyrethroids
to. % mortality for esfenvalerate and bifenthrin is the average of the two tests. Information on the insecticidal activity of the bollworm at selected application intervals in which the technical active ingredients were dissolved as described above is provided in Table 5. L.
Numbers in bold and in italics indicated that a beneficial insecticidal effect was observed when compared with individual compounds. Table 5 Acorn worm. (Heliothis zearBoddiel). Insecticidal activity of bifenthrin and cyano-pyrethroid.
The information on the insecticidal activity of cotton aphid at selected application intervals in which the active ingredients were dissolved as described above is provided in Table 6. The numbers in bold and italic indicate beneficial insecticidal effect that was observed when it was compared with individual compounds.
Table 6 Cotton Aphid (Aphis qossv, jP // fGlover1). Insecticidal activity of Bifentrina and Ciano pyrethroids
* NT (for its acronym in English) = Not Tested a.% Mortality for esfenvalerate and bifenthrin is the average of tests.
The information of the miticidal activity of the red spider in
Selected ranges of application in which the active ingredients were dissolved as described above are provided in Table 7. The numbers in bold and italic indicate beneficial insecticidal effect that was observed when compared with individual compounds.
Table 7 Red spider (Tetranychus urticae KochT). Insecticidal activity of Bifentrina and cyano-pyrethroids
* NT = Not Tested While that invention has been described with emphasis on the preferred embodiments, it would be understood by those skilled in the art that variations of the preferred embodiments may be utilized and that it is intended that the invention be practiced distinctly as described herein. . Accordingly, the invention includes all modifications that are within the spirit and scope of the invention as defined in the claims that follow.
Claims (7)
- CLAIMS 1. An insecticidal or miticidal composition comprising bifenthrin and a cyano-pyrethroid selected from the group consisting of acrinatrin, cycloprothrine, deltamethrin, tralometrine, fenvalerate, cyfluthrin, oper-cyfluthrin, flucythrinate, alpha-cypermethrin, / befa-cypermethrin, fefa-cypermethrin, zeta-cypermethrin, cyphenothrin, cyhalothrin, / ambda-cyhalothrin, esfenvalerate, fluvalinate and fenpropathrin.
- 2. A composition according to claim 1, wherein the range of bifenthrin to cyano-pyrethroid is from 1/99 to 99/1.
- 3. A composition according to claim 1, wherein the cyano-pyrethroid is selected from deltamethrin, cylfutrin, a / r "a-cypermethrin, zefa-cypermethrin, / ambdacylarothrin and esfenvalerate. with claim 1, wherein the cyano-pyrethroid is zefa-cypermethrin 5. A composition according to claim 4, wherein the zefa-cypermethrin is (R, S) -a-cyano-3-phenoxybenzyl- (1) RS) -c / 's-frarts-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate which has been enriched with 1R-C / SS isomers and 1 R-trans-S by reaction of 55/45 cis / trans mixture of cypermethrin with a catalytic amount of tricaprylammonium chloride and sodium carbonate in n-heptane. 6. A composition according to claim 1, further comprising an acceptable adjuvant and agricultural adjuvant. A method for controlling unwanted insects or mites comprising applying a composition according to claim 1, to a place where insects or mites are present or expected to be present.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US60/752,979 | 2005-12-22 |
Publications (1)
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MX2008008174A true MX2008008174A (en) | 2008-10-03 |
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