WO2013165793A1 - Synergistic pesticidal compositions - Google Patents
Synergistic pesticidal compositions Download PDFInfo
- Publication number
- WO2013165793A1 WO2013165793A1 PCT/US2013/038122 US2013038122W WO2013165793A1 WO 2013165793 A1 WO2013165793 A1 WO 2013165793A1 US 2013038122 W US2013038122 W US 2013038122W WO 2013165793 A1 WO2013165793 A1 WO 2013165793A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- insecticides
- methyl
- spp
- mmol
- synergistic composition
- Prior art date
Links
- 0 *CC(*)CN=O Chemical compound *CC(*)CN=O 0.000 description 6
- XMEGDAGGGYFBNY-UHFFFAOYSA-N CS(Cc1ccc(C(F)(F)F)nc1)(=NC#N)=O Chemical compound CS(Cc1ccc(C(F)(F)F)nc1)(=NC#N)=O XMEGDAGGGYFBNY-UHFFFAOYSA-N 0.000 description 2
- NIIQNXLCSFHRAX-BEDCHXNXSA-N CC(/C(/C)=C/C=C(/C(F)(F)Cl)\N=C)SC Chemical compound CC(/C(/C)=C/C=C(/C(F)(F)Cl)\N=C)SC NIIQNXLCSFHRAX-BEDCHXNXSA-N 0.000 description 1
- VFHZKNHYCFKIBL-UHFFFAOYSA-N CC(c1ccc(C(F)(F)Cl)nc1)/S(/C)=N/C Chemical compound CC(c1ccc(C(F)(F)Cl)nc1)/S(/C)=N/C VFHZKNHYCFKIBL-UHFFFAOYSA-N 0.000 description 1
- PHBHUOZUNYIUKS-UHFFFAOYSA-N CC(c1ccc(C(F)(F)Cl)nc1)SC Chemical compound CC(c1ccc(C(F)(F)Cl)nc1)SC PHBHUOZUNYIUKS-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N CC(c1ccc(C(F)(F)F)nc1)S(C)(=NC#N)=O Chemical compound CC(c1ccc(C(F)(F)F)nc1)S(C)(=NC#N)=O ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- UWPUFAJHIFVDNX-UHFFFAOYSA-N CC(c1ccc(C(F)(F)[F]F)nc1)S(C)(=NC#N)=O Chemical compound CC(c1ccc(C(F)(F)[F]F)nc1)S(C)(=NC#N)=O UWPUFAJHIFVDNX-UHFFFAOYSA-N 0.000 description 1
- QCBQMAKHLNEBHQ-UHFFFAOYSA-N CC(c1cnc(C(F)(F)Cl)cc1)Cl Chemical compound CC(c1cnc(C(F)(F)Cl)cc1)Cl QCBQMAKHLNEBHQ-UHFFFAOYSA-N 0.000 description 1
- IGCCRIYCQYUIPO-UHFFFAOYSA-N CCC(c1ccc(C(F)(F)F)nc1)S(C)(=NC)=O Chemical compound CCC(c1ccc(C(F)(F)F)nc1)S(C)(=NC)=O IGCCRIYCQYUIPO-UHFFFAOYSA-N 0.000 description 1
- AFWGCIRTNPZRMP-UHFFFAOYSA-N N#CN=S(CCC1)(C1c(cn1)ccc1Cl)=O Chemical compound N#CN=S(CCC1)(C1c(cn1)ccc1Cl)=O AFWGCIRTNPZRMP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01V—GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS
- G01V1/00—Seismology; Seismic or acoustic prospecting or detecting
- G01V1/003—Seismic data acquisition in general, e.g. survey design
- G01V1/005—Seismic data acquisition in general, e.g. survey design with exploration systems emitting special signals, e.g. frequency swept signals, pulse sequences or slip sweep arrangements
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01V—GEOPHYSICS; GRAVITATIONAL MEASUREMENTS; DETECTING MASSES OR OBJECTS; TAGS
- G01V1/00—Seismology; Seismic or acoustic prospecting or detecting
- G01V1/24—Recording seismic data
Definitions
- the present application is related to the field of pesticides and their use in controlling pests.
- Insects are developing resistance to pesticides in current use. Hundreds of insect species are resistant to one or more pesticides. The development of resistance to some of the older pesticides, such as DDT, the carbamates, and the organophosphates, is well known. But resistance has even developed to some of the newer pesticides. Therefore, there is an acute need for new and/or improved pesticides.
- alkoxy means an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, 1-butoxy, 2-butoxy, isobutoxy, tert-butoxy, pentoxy, 2-methylbutoxy, 1, 1-dimethylpropoxy, hexoxy, heptoxy, octoxy, nonoxy, and decoxy.
- alkyl means an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, propyl, isopropyl, 1 -butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, nonyl, and decyl.
- halo means fluoro, chloro, bromo, and iodo.
- haloalkyl means an alkyl further consisting of, from one to the maximum possible number of, identical or different, halos, for example, fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, chloromethyl, trichloromethyl, and 1, 1,2,2-tetrafluoroethyl.
- Figure 1 is a bar graph illustrating LC50/90 Cotton Aphid values of different compositions.
- Figure 2 is a bar graph comparing expected and measured Cotton Aphid control rates.
- Pesticide compositions have been surprisingly discovered where one or more pesticide compounds of the following formula are synergistic with one or more herbicides.
- X represents N0 2 , CN or COOR 4 ;
- L represents a single bond or R 1 , S and L taken together represent a 5- or 6-membered ring;
- R 1 represents methyl or ethyl
- R 2 and R 3 independently represent hydrogen, methyl, ethyl, fluoro, chloro or bromo; n is an integer from 0-3;
- Y represents 6-halopyridin-3-yl, 6-(C 1 -C4)alkylpyridin-3-yl, 6-halo(C)-C4)
- R 4 represents C1 -C3 alkyl.
- step a of Scheme A sulfide of formula (A) is oxidized with meta- chloroperoxybenzoic acid (mCPBA) in a polar solvent below 0 °C to provide sulfoxide of formula (B).
- mCPBA meta- chloroperoxybenzoic acid
- dichloromethane is the preferred solvent for oxidation.
- step b of Scheme A sulfoxide (B) is iminated with sodium azide in the presence of concentrated sulfuric acid in an aprotic solvent under heating to provide sulfoximine of formula (C). In most cases, chloroform is the preferred solvent for this reaction.
- the nitrogen of sulfoximine (C) can be either cyanated with cyanogen bromide in the presence of a base, or nitrated with nitric acid in the presence of acetic anhydride under mildly elevated temperature, or carboxylated with alkyl (R 4 ) chloroformate in the presence of base such as 4-dimethylaminopyridine (DMAP) to provide N-substituted sulfoximine (la).
- base is required for efficient cyanation and carboxylation and the preferred base is DMAP, whereas sulfuric acid is used as catalyst for efficient nitration reaction.
- step a of Scheme B sulfide is oxidized with iodobenzene diacetate in the presence of cyanamide at 0 °C to give sulfilimine (F).
- the reaction can be carried out in a polar aprotic solvent like dichloromethane.
- step b of Scheme B the sulfilimine (F) is oxidized with MCPBA.
- a base such as potassium carbonate is employed to neutralize the acidity of mCPBA.
- Protic polar solvents such as ethanol and water are used to increase the solubility of the sulfilimine starting material and the base employed.
- the sulfilimine (F) can also be oxidized with aqueous sodium or potassium periodinate solution in the presence of catalyst ruthenium trichloride hydrate or similar catalyst.
- the organic solvent for this catalysis can be polar aprotic solvent such as dichloromethane, chloroform, or acetonitrile.
- (CR 2 R 3 ) group adjacent to the N-substituted sulfoximine function can be further alkylated or halogenated (R 5 ) in the presence of a base such as potassium hexamethyldisilamide
- base such as potassium tert- butoxide
- the corresponding appropriately substituted chloromethyl pyridine is treated with thiourea, hydrolyzed and subsequently alkylated with l -bromo-3-chloropropane under aqueous base conditions, and cyclized in the presence of a base like potassium tert-butoxide in a polar aprotic solvent such as tetrahydrofuran (THF).
- a base like potassium tert-butoxide in a polar aprotic solvent such as tetrahydrofuran (THF).
- step a of Scheme J which is similar to step b of Scheme A, sulfoxide is iminated with sodium azide in the presence of concentrated sulfuric acid or with O- mesitylsulfonylhydroxylamine in a polar aprotic solvent to provide sulfoximine.
- Chloroform or dichloromethane are the preferred solvents.
- step b of Scheme J similar to step c of Scheme A, the nitrogen of sulfoximine can be either cyanated with cyanogen bromide, or nitrated with nitric acid followed by treatment with acetic anhydride under refluxing conditions, or carboxylated with methyl chloro formate in the presence of base such as DMAP to provide N-substituted cyclic sulfoximine.
- Base is required for efficient cyanation and carboxylation and the preferred base is DMAP, whereas sulfuric acid is used as catalyst for efficient nitration reaction.
- the a-carbon of N-substituted sulfoximine can be alkylated with a heteroaromatic methyl halide in the presence of a base such as KHMDS or butyl lithium (BuLi) to give the desired N-substituted sulfoximines.
- a base such as KHMDS or butyl lithium (BuLi)
- the preferred halide can be bromide, chloride or iodide.
- the compounds of formula (lb) can be prepared by a first a-alkylation of sulfoxides to give a-substituted sulfoxides and then an imination of the sulfoxide followed by N-substitution of the resulting sulfoximine by using the steps c , a and b respectively as described above for Scheme J.
- the pesticide compositions disclosed herein include a cyanosulfoximine compound according to formula (I), non-limiting examples of which are hereinafter provided. It should be understood that these and other examples provided herein are for illustration purposes and are not to be construed as limiting the invention disclosed in this document to only the embodiments disclosed in these examples.
- sulfoximine (1) 50 mg, 0.19 mmol
- HMPA hexamethyl-phosphoramide
- THF tetrahydrofuran
- KHMDS potassium hexamethyldisilazane
- sulfoximine (2) is also referred to as [methyl(oxido) ⁇ l-[6- (trifluoromethyl)-3-pyridyl]ethyl ⁇ - ⁇ 6 -sulfanylidene]cyanamide, and the CAS name given to sulfoximine (2) is N-[methyloxido[l-[6-(trifluoromethyl)-3-pyridinil]ethyl] ⁇ 4 - sulfanylidene]cyanamide.
- Example IV [ 6-Chloropyridin-3-v ⁇ methyl methyl oxido- ⁇ 4 -sulfanylidene-cvanamide (4).
- [(6-Chloropyridin-3-yl)methyl](methyl)oxido- ⁇ 4 -sulfanylidenecyanamide (4) was prepared from 3-chloromethyl-6-chloropyridine via the same 3 step sequence outline in Example I.
- 2-(6-Chloropyridin-3-yl)-l-oxido-tetrahydro-lH- -thien-l-ylidenecyanamide (8) was prepared from 3-chloromethyl-6-chloropyridine according to the same five step sequence described in Example III. Product was a colorless gum and a 1 : 1 ratio of diastereomers.
- Diastereomer 1 IR (film) 3439, 3006, 2949, 2194 cm “1 ; ] H NMR (300 MHz, CDC1 3 ): ⁇ 8.4 (d, IH), 7.8 (dd, IH), 7.4 (d, IH), 4.6 (dd, IH), 3.6 (m, 2H), 2.4-2.7 (m, 4H); GC-MS: mass calcd for CioH traversClN 3 OS [M+H] + 256. Found 256.
- Diastereomer 2 IR (film) 3040, 2926, 2191 cm “1 ; ] H NMR (300 MHz, CDC1 3 ): ⁇ 8.4 (d, IH), 7.8 (dd, IH), 7.4 (d, IH), 4.7 (dd, IH), 3.8 (ddd, IH), 3.4 (m, IH), 2.8 (m, IH), 2.6 (m, 2H), 2.3 (m, IH); GC-MS: mass calcd for CioHnClN 3 OS [M+H] + 256. Found 256.
- methylmagnesium bromide in hexane (6.4 mL, 19 mmol) was added through a syringe. After the addition was over, the mixture was stirred at 0 °C for 5 hr and then at room temperature for 10 hr. The reaction was quenched slowly with 1 N citric acid aqueous solution at 0 °C and the resulting mixture was stirred at room temperature for 1 hr. The pH was adjusted back to pH 7 with saturated NaHC0 3 aqueous solution. The two phases were separated and the aqueous phase was extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over anhydrous Na 2 S04, filtered, and concentrated.
- the pesticide compositions disclosed herein include a herbicide with which a pesticide compound according to formula (I) is synergistic.
- the herbicide is an organophosphorus herbicide, non-limiting examples of which include amiprofos-methyl, amiprophos, anilofos, bensulide, bilanafos, butamifos, clacyfos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-P, glyphosate, huangcaoling, piperophos and shuangjiaancaolin.
- organophosphorus herbicide non-limiting examples of which include amiprofos-methyl, amiprophos, anilofos, bensulide, bilanafos, butamifos, clacyfos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-
- the herbicide is glufosinate. In another non-limiting form, the herbicide is glyphosate. It is also contemplated that mixtures of one or more of the foregoing organophosphorus herbicides could be included in the pesticide compositions disclosed herein.
- the pesticide compound according to formula (I) and the herbicide are generally present in the pesticide compositions disclosed herein in synergistically effective amounts. In one form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 0.2: 1 to 9200: 1.
- the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 2: 1 to 920: 1. In yet another form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 5: 1 to 400: 1. In still another form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 5:1 to 400:1. In another form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 10: 1 to 200: 1. In yet another form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 5: 1 to 40: 1. In still another form, the ratio by weight between the herbicide or a formulation including the herbicide and the pesticide is in the range of 70: 1 to 1 10: 1. However, it should be understood that alternative values for the ratio by weight between the herbicide and the pesticide are possible.
- an adjuvant may be optionally included with the pesticide and herbicide.
- the adjuvant is or includes an ammonium salt, such as ammonium sulfate.
- an ammonium salt such as ammonium sulfate.
- the ratio by weight between the adjuvant and the remaining composition components is in the range of 0.015: 1 to 700: 1. In another form, the ratio by weight between the adjuvant and the remaining composition components is in the range of 0.1 : 1 to 70: 1. In still another form, the ratio by weight between the adjuvant and the remaining composition components is in the range of 0.4: 1 to 30: 1. In yet another form, the ratio by weight between the adjuvant and the remaining composition components is in the range of 0.5: 1 to 6: 1. In another form, the ratio by weight between the adjuvant and the remaining composition components is in the range of 2: 1 to 12: 1. However, it should be understood that alternative values for the ratio by weight between the adjuvant and the remaining composition components are possible. Insecticidal Testing
- Compound A is also known as sulfoxaflor (sulfoximine (2)).
- Glyphosate resistant cotton plants (Gossypium hirsutum, cv 'DP493 ') were trimmed to 1 true leaf and infested with mixed stages of cotton aphid (CA) Aphis gossypii 24 h prior to application.
- CA cotton aphid
- Mixed developmental stage CA were infested onto the upper surface of each treated leaf by transferring infested foliage from an insectary colony.
- Each plant was infested with approximately equal numbers of CA based on visual estimation of aphid density on the infested material. Infested plants were held in the growth chamber (L:D 16:8 and 25°C).
- Glyphosate (Glyphomax Plus, Dow AgroSciences, LLC, Indianapolis, Indiana) was mixed with water at a rate equivalent to 32 oz/ Ac/20 gallons. This solution rate was 12.5 ml/L. This volume was subdivided into equal fractions and ammonium sulfate (AMS) was added to one fraction at a rate of 18 g/1. Additionally, a solution of AMS in pure water was generated ( 18 g/1). High rate Compound A concentrations were created by diluting Compound A technical material with acetone to achieve a 10 ppm solution.
- AMS ammonium sulfate
- compositions including Compound A, herbicide and AMS as5 were adapted for compositions including Compound A, herbicide and AMS as5 follows:
- Table 2 suggests that the increased activity of compositions including Compound A and the herbicide is indicative of synergy that is not present when imidacloprid was tested.
- the addition of AMS and herbicide to Compound A also resulted in a synergyistic improvement in activity.
- the three way mixture of imidacloprid with AMS and herbicide was not improved compared to imidacloprid alone.
- Glyphosate resistant cotton plants (Gossypium hirsutum, cv 'DP493') were trimmed to 1 true leaf and infested with mixed stages of cotton aphid (CA) Aphis gossypii 24 h prior to application.
- CA cotton aphid
- Mixed developmental stage CA were infested onto the upper surface of each treated leaf by transferring infested foliage from an insectary colony.
- Each plant was infested with approximately equal numbers of CA based on visual estimation of aphid density on the infested material. Infested plants were held in the growth chamber (L:D 16:8 and 25°C).
- Glyphosate (Durango®, Dow AgroSciences, LLC, Indianapolis, Indiana) was mixed with water at a rate equivalent to 15 ml/L (1.2 qt/Ac). All water used contained Tween® 20 (Sigma Aldrich, St. Louis, Missouri) adjuvant at a rate of 0.125% (V:V). A glyphosate free formulation of Durango® was prepared using these same mixing instructions. These formulated volumes were subdivided into equal fractions and AMS was added to one fraction of each at a rate of 18 g/1. Additionally, a solution of AMS in pure water was generated ( 18 g/1 ). High rate Compound A concentrations were created by diluting Compound A technical material with acetone to achieve a 10 ppm solution.
- the track sprayer was calibrated prior to applying the Compound A formulation using a blank glyphosate and AMS solution to deliver a spray volume of 200 L/Ha through a single, hollow cone nozzle (Spraying Systems XS-6, Glendale Heights, Illinois). Nozzle height above the canopy was held constant at ca. 30 cm. Plants were evaluated after 3 days from the time of infestation by counting all live cotton aphids on each plant. A full list of compounds and formulations used and test results is provided in TABLE 3. TABLE 3
- compositions having lower rates of the insecticide were not analyzed. Percent control for all treatments was calculated using the rep average for the untreated plants. Homogeneity of variance by compound was tested for measured percent control (actual) and Colby predicted values at the 0.2 g insecticide/Ha rate and these 5 data were found to have homogeneous variances (Levene's test, P »0.05). Results are:
- Glyphosate resistant cotton plants (Gossypium hirsutum, cv 'DP493') were trimmed to 1 true leaf and infested with mixed stages of cotton aphid (CA) Aphis gossypii 24 h prior to application.
- CA cotton aphid
- Mixed developmental stage CA were infested onto the upper surface of each treated leaf by transferring infested foliage from an insectary colony.
- Each plant was infested with approximately equal numbers of CA based on visual estimation of aphid density on the infested material. Infested plants were held in the growth chamber (L:D 16:8 and 25°C).
- Glufosinate (Liberty®, Bayer CropScience, Monheim am Rhein, Germany) was mixed with water at a rate equivalent to 5 ml/L (0.4 qt/Ac). All water used contained Tween® 20 adjuvant at a rate of 0.125% (V:V). These formulated volumes were subdivided into equal fractions and AMS was added to one fraction of each at a rate of 18 g/L. Additionally, a solution of AMS in pure water was generated (18 g/L). High rate Compound A
- concentrations were created by diluting Compound A technical material with acetone to achieve a 10 ppm solution. 0.2 ml of this acetone stock solution was added to either 19.8 ml of water, glufosinate solution or glufosinate and AMS solution to generate 1 ppm high rate Compound A concentrations. Successively lower concentrations were generated by serially diluting in 4-fold increments with either water, glufosinate solution or glufosinate and AMS solution as appropriate to achieve solutions concentrations of 0.25 and 0.0625 ppm. When applied through a track sprayer calibrated to 200 L/Ha these concentrations generated use rates of 0.2, 0.0625 and 0.015 g/Ha.
- the track sprayer was calibrated using a blank glufosinate and AMS solution to deliver a spray volume of 200 L/Ha through a single, hollow cone nozzle (Spraying Systems XS-6). Nozzle height above the canopy was held constant at ca. 30 cm. Plants were evaluated after 3 days from the time of infestation by counting all live cotton aphids on each plant. A full list of compounds and formulations used and test results is provided in TABLE 5.
- TABLE 6 contains the calculated Colby values for combinations of treatments as well as the outcome of statistical evaluations between predicted (Colby) and actual measured values. These T-test statistics were only calculated for the 0.2 and 0.05 g/Ha rates.
- the combination of glufosinate and imidacloprid was not different from the calculated additive values. These same trends were apparent when Compound A was applied with both glufosinate and AMS. In this case synergy between Compound A and 10 glufosinate and AMS was strongly indicated. No evidence of synergy was apparent when imidacloprid was combined with glufosinate and AMS.
- CA cotton aphid
- concentrations were created by diluting Compound A technical material with acetone to achieve a 20 ppm solution. 0.2 ml of this acetone stock solution was added to either 19.8 ml of water, glufosinate solution or glufosinate and AMS solution to generate 2 ppm high rate Compound A concentrations. Successively lower concentrations were generated by serially diluting in 4-fold increments with either water, glufosinate solution or glufosinate and AMS solution as appropriate to achieve solution concentrations of 0.5 and 0.125 ppm. When applied through a track sprayer calibrated to 200 L/Ha these concentrations generated use rates of 0.4, 0.1 and 0.025 g/Ha.
- the track sprayer was calibrated using a blank glufosinate and AMS solution to deliver a spray volume of 200L/Ha through a single, hollow cone nozzle (Spraying Systems XS-6). Nozzle height above the canopy was held constant at ca. 30 cm. Plants were evaluated after 3 days from the time of infestation by counting all live cotton aphids on each plant. A full list of compounds and formulations used and test results is listed in TABLE 7.
- TABLE 8 contains the calculated Colby values for combinations of treatments as well as the outcome of statistical evaluations between predicted (Colby) and actual measured values. Coapplication of Compound A and glufosinate did not have a synergistic effect based on a comparison with predicted additive activity. However, when Compound A was applied with glufosinate and AMS the activity was significantly increased.
- Glyphosate resistant cotton plants (Gossypium hirsutum, cv 'DP493 ') were trimmed to 1 true leaf and infested with mixed stages of cotton aphid (CA) Aphis gossypii lA h prior to application.
- CA cotton aphid
- Mixed developmental stage CA were infested onto the upper surface of each treated leaf by transferring infested foliage from an insectary colony.
- Each plant was infested with approximately equal numbers of CA based on visual estimation of aphid density on the infested material. Infested plants were held in the growth chamber (L:D 16:8 and 25°C).
- Bioefficacy tests were performed utilizing formultions of Compound A (Composition 1), Glyphosate (Roundup® Pro, The Scotts Company, LLC, Marysville, Ohio), a mixute of Compound A and Glyphosate (Composition 2), and water. Each of these formulations also included 0.03% Silwet® L-77 Surfactant (Helena Chemical Company, Collierville,
- composition 2 included a 1 : 1 ratio between Compound A and
- an amine function can form salts with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic, aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic, hydroxymethanesulfonic, and hydroxyethanesulfonic, acids.
- an acid function can form salts including those derived from alkali or alkaline earth metals and those derived from ammonia and amines.
- preferred cations include sodium, potassium, magnesium, and aminium cations.
- the salts are prepared by contacting the free base form with a sufficient amount of the desired acid to produce a salt.
- the free base forms may be regenerated by treating the salt with a suitable dilute aqueous base solution such as dilute aqueous NaOH, potassium carbonate, ammonia, and sodium bicarbonate.
- a pesticide is modified to a more water soluble form e.g. 2,4-dichlorophenoxy acetic acid dimethyl amine salt is a more water soluble form of 2,4-dichlorophenoxy acetic acid a well known herbicide.
- the compounds disclosed in this document can also form stable complexes with solvent molecules that remain intact after the non-complexed solvent molecules are removed from the compounds. These complexes are often referred to as "solvates”.
- Certain compounds disclosed in this document can exist as one or more stereoisomers.
- the various stereoisomers include geometric isomers, diastereomers, and enantiomers.
- the compounds disclosed in this document include racemic mixtures, individual
- stereoisomers, and optically active mixtures are stereoisomers, and optically active mixtures. It will be appreciated by those skilled in the art that one stereoisomer may be more active than the others. Individual stereoisomers and optically active mixtures may be obtained by selective synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional resolution procedures.
- compositions disclosed in this document can be used to control pests.
- compositions disclosed in this document can be used to control pests of the Phylum Nematoda.
- compositions disclosed in this document can be used to control pests of the Phylum Arthropoda.
- compositions disclosed in this document can be used to control pests of the Subphylum Chelicerata. In another embodiment, the compositions disclosed in this document can be used to control pests of the Class Arachnida.
- compositions disclosed in this document can be used to control pests of the Subphylum Myriapoda.
- compositions disclosed in this document can be used to control pests of the Class Symphyla.
- compositions disclosed in this document can be used to control pests of the Subphylum Hexapoda.
- compositions disclosed in this document can be used to control pests of the Class Insecta.
- compositions disclosed in this document can be used to control Coleoptera (beetles).
- a non-exhaustive list of these pests includes, but is not limited to, Acanthoscelides spp. (weevils), Acanthoscelides obtectus (common bean weevil), Agrilus planipennis (emerald ash borer), Agriotes spp. (wireworms), Anoplophora glabripennis (Asian longhorned beetle), Anthonomus spp. (weevils), Anthonomus grandis (boll weevil), Aphidius spp., Apion spp. (weevils), Apogonia spp. (grubs), Ataenius spretulus (Black Turgrass Ataenius), Atomaria linearis (pygmy mangold beetle), Aulacophore spp.,
- Bothynoderes punctiventris (beet root weevil), Bruchus spp. (weevils), Bruchus pisorum (pea weevil), Cacoesia spp., Callosobruchus maculatus (southern cow pea weevil), Carpophilus hemipteras (dried fruit beetle), Cassida vittata, Cerosterna spp, Cerotoma spp.
- Conoderus stigmosus Conotrachelus nenuphar (plum curculio), Cotinus nitidis (Green June beetle), Crioceris asparagi (asparagus beetle), Cryptolestes ferrugineus (rusty grain beetle), Cryptolestes pusillus (flat grain beetle), Cryptolestes turcicus (Turkish grain beetle), Ctenicera spp. (wireworms), Curculio spp. (weevils), Cyclocephala spp. (grubs),
- Cylindrocpturus adspersus (sunflower stem weevil), Deporaus marginatus (mango leaf- cutting weevil), Dermestes lardarius (larder beetle), Dermestes maculates (hide beetle), Diabrotica spp. (chrysolemids), Epilachna varivestis (Mexican bean beetle), Faustinus cubae, Hylobius pales (pales weevil), Hypera spp. (weevils), Hypera postica (alfalfa weevil), Hyperdoes spp. (Hyperodes weevil), Hypothenemus hampei (coffee berry beetle), Ips spp.
- compositions disclosed in this document can be used to control Dermaptera (earwigs).
- compositions disclosed in this document can be used to control Dictyoptera (cockroaches).
- Dictyoptera cockroaches
- a non-exhaustive list of these pests includes, but is not limited to, Blattella germanica (German cockroach), Blatta orientalis (oriental cockroach), Parcoblatta pennylvanica, Periplaneta americana (American cockroach), Periplaneta australoasiae (Australian cockroach), Periplaneta brunnea (brown cockroach), Periplaneta fuliginosa (smokybrown cockroach), Pyncoselus suninamensis (Surinam cockroach), and Supella longipalpa (brownbanded cockroach).
- the invention disclosed in this document can be used to control Diptera (true flies).
- a non-exhaustive list of these pests includes, but is not limited to, Aedes spp. (mosquitoes), Agromyza frontella (alfalfa blotch leafminer), Agromyza spp. (leaf miner flies), Anastrepha spp. (fruit flies), Anastrepha suspensa (Caribbean fruit fly), Anopheles spp. (mosquitoes), Batrocera spp. (fruit flies), Bactrocera cucurbitae (melon fly), Bactrocera dorsalis (oriental fruit fly), Ceratitis spp. (fruit flies), Ceratitis capitata
- Muscid flies Musca autumnalis (face fly), Musca domestica (house fly), Oestrus ovis (sheep bot fly), Oscinella frit (frit fly), Pegomyia betae (beet leafminer), Phorbia spp., Psila rosae (carrot rust fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple maggot), Sitodiplosis mosellana (orange wheat blossom midge), Stomoxys calcitrans (stable fly), Tabanus spp. (horse flies), and Tipula spp. (crane flies).
- compositions disclosed in this document can be used to control Hemiptera (true bugs).
- a non-exhaustive list of these pests includes, but is not limited to, Acrosternum hilare (green stink bug), Blissus leucopterus (chinch bug), Calocoris norvegicus (potato mirid), Cimex hemipterus (tropical bed bug), Cimex lectularius (bed bug), Dagbertus fasciatus, Dichelops furcatus, Dysdercus suturellus (cotton stainer), Edessa meditabunda, Eurygaster maura (cereal bug), Euschistus hews, Euschistus servus (brown stink bug), Helopeltis antonii, Helopeltis theivora (tea blight plantbug), Lagynotomus spp.
- compositions disclosed in this document can be used to control Homoptera (aphids, scales, whiteflies, leafhoppers).
- Homoptera aphids, scales, whiteflies, leafhoppers.
- a non-exhaustive list of these pests includes, but is not limited to, Acrythosiphon pisum (pea aphid), Adelges spp.
- adelgids Aleurodes proletella (cabbage whitefly), Aleurodicus disperses, Aleurothrixus floccosus (woolly whitefly), Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp. (leafhoppers), Aonidiella aurantii (California red scale), Aphis spp. (aphids), Aphis gossypii (cotton aphid), Aphis pomi (apple aphid), Aulacorthum solani (foxglove aphid), Bemisia spp.
- Rhapalosiphum spp. aphids
- Rhapalosiphum maida corn leaf aphid
- Rhapalosiphum padi oat bird-cherry aphid
- Saissetia spp. scales
- Saissetia oleae black scale
- Schizaphis graminum greenbug
- Sitobion avenae English grain aphid
- Sogatella furcifera white- backed planthopper
- Therioaphis spp. aphids
- Toumeyella spp. scales
- Toxoptera spp. aphids
- compositions disclosed in this document can be used to control Hymenoptera (ants, wasps, and bees).
- Hymenoptera insects, wasps, and bees.
- a non-exhaustive list of these pests includes, but is not limited to, Acromyrrmex spp., Athalia rosae, Atta spp. (leafcutting ants), Camponotus spp. (carpenter ants), Diprion spp. (sawflies), Formica spp. (ants), Iridomyrmex humilis (Argentine ant), Monomorium ssp., Monomorium minumum (little black ant), Monomorium pharaonis (Pharaoh ant), Neodiprion spp.
- compositions disclosed in this document can be used to control Isoptera (termites).
- a non-exhaustive list of these pests includes, but is not limited to, Coptotermes spp., Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus (Formosan subterranean termite), Cornitermes spp. (nasute termites),
- Cryptotermes spp. drywood termites
- Heterotermes spp. deert subterranean termites
- Heterotermes aureus Kalotermes spp.
- Kalotermes spp. drywood termites
- Incistitermes spp. drywood termites
- Macrotermes spp. fungus growing termites
- Marginitermes spp. drywood termites
- Microcerotermes spp. harvester termites
- Microtermes obesi Procornitermes spp.
- Reticulitermes speratus Reticulitermes tibialis, Reticulitermes virginicus
- compositions disclosed in this document can be used to control Lepidoptera (moths and butterflies).
- Lepidoptera moths and butterflies.
- a non-exhaustive list of these pests includes, but is not limited to, Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp.
- Carposina niponensis peach fruit moth
- Chilo spp. Chlumetia transversa (mango shoot borer), Choristoneura rosaceana (obliquebanded leafroller), Chrysodeixis spp.,
- Cnaphalocerus medinalis grass leafroller
- Colias spp. Conpomorpha cramerella, Cossus cossus (carpenter moth), Crambus spp. (Sod webworms), Cydia funebrana (plum fruit moth), Cydia molesta (oriental fruit moth), Cydia nignicana (pea moth), Cydia pomonella (codling moth), Darna diducta, Diaphania spp. (stem borers), Diatraea spp. (stalk borers), Diatraea saccharalis (sugarcane borer), Diatraea graniosella (southwester corn borer), Earias spp.
- Polychrosis viteana (grape berry moth), Prays endocarpa,Prays oleae (olive moth), Pseudaletia spp. (noctuid moths), Pseudaletia unipunctata (armyworm), Pseudoplusia includens (soybean looper), Rachiplusia nu, Scirpophaga incertulas, Sesamia spp.
- compositions disclosed in this document can be used to control Mallophaga (chewing lice).
- Mallophaga chewing lice
- a non-exhaustive list of these pests includes, but is not limited to, Bovicola ovis (sheep biting louse), Menacanthus stramineus (chicken body louse), and Menopon gallinea (common hen house).
- compositions disclosed in this document can be used to control Orthoptera (grasshoppers, locusts, and crickets).
- Orthoptera grasshoppers, locusts, and crickets.
- a non-exhaustive list of these pests includes, but is not limited to, Anabrus simplex (Mormon cricket), Gryllotalpidae (mole crickets), Locusta migratoria, Melanoplus spp.(grasshoppers), Microcentrum retinerve (angularwinged katydid), Pterophylla spp. (kaydids), chistocerca gregaria, Scudderia furcata (forktailed bush katydid), and Valanga nigricorni.
- compositions disclosed in this document can be used to control Phthiraptera (sucking lice).
- Phthiraptera sucing lice
- a non-exhaustive list of these pests includes, but is not limited to, Haematopinus spp. (cattle and hog lice), Linognathus ovillus (sheep louse), Pediculus humanus capitis (human body louse), Pediculus humanus humanus (human body lice), and Pthirus pubis (crab louse).
- compositions disclosed in this document can be used to control Siphonaptera (fleas).
- Siphonaptera fleas
- a non-exhaustive list of these pests includes, but is not limited to, Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea), and Pulex irritans (human flea).
- compositions disclosed in this document can be used to control Thysanoptera (thrips).
- thrips Thysanoptera
- a non-exhaustive list of these pests includes, but is not limited to, Frankliniella fusca (tobacco thrips), Frankliniella occidentalis (western flower thrips), Frankliniella shultzei Frankliniella williamsi (corn thrips), Heliothrips
- compositions disclosed in this document can be used to control Thysanura (bristletails).
- Thysanura bristletails
- a non-exhaustive list of these pests includes, but is not limited to, Lepisma spp. (silverfish) and Thermobia spp. (firebrats).
- compositions disclosed in this document can be used to control Acarina (mites and ticks).
- a non-exhaustive list of these pests includes, but is not limited to, Acarapsis woodi (tracheal mite of honeybees), Acarus spp. (food mites), Acarus siro (grain mite), Aceria mangiferae (mango bud mite), Aculops spp., Aculops lycopersici (tomato russet mite), Aculops pelekasi, Aculus pelekassi, Aculus convincedendali (apple rust mite), Amblyomma americanum (lone star tick), Boophilus spp.
- Dermatophagoides pteronyssinus house dust mite
- Eotetranycus spp. Eotetranychus carpini (yellow spider mite)
- Epitimerus spp. Eriophyes spp.
- Ixodes spp. ticks
- Tetranychus urticae twospotted spider mite
- Varroa destructor honey bee mite
- compositions disclosed in this document can be used to control Nematoda (nematodes).
- Nematoda nematodes
- a non-exhaustive list of these pests includes, but is not limited to, Aphelenchoides spp. (bud and leaf & pine wood nematodes), Belonolaimus spp. (sting nematodes), Criconemella spp. (ring nematodes), Dirofilaria immitis (dog heartwom), Ditylenchus spp. (stem and bulb nematodes), Heterodera spp. (cyst nematodes), Heterodera zeae (corn cyst nematode), Hirschmanniella spp.
- root nematodes Hoplolaimus spp. (lance nematodes), Meloidogyne spp. (root knot nematodes), Meloidogyne incognita (root knot nematode), Onchocerca volvulus (hook-tail worm), Pratylenchus spp. (lesion nematodes), Radopholus spp. (burrowing nematodes), and Rotylenchus reniformis (kidney-shaped nematode).
- compositions disclosed in this document can be used to control Symphyla (symphylans).
- Symphyla symphylans
- a non-exhaustive list of these pests includes, but is not limited to, Scutigerella immaculata.
- pesticides that can be employed beneficially in combination with the compositions disclosed in this document include, but are not limited to the following:
- cadusafos calcium arsenate, calcium polysulfide, camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorbenside, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlorethoxyfos, chlorfenapyr, chlorfenethol, chlorfenson, chlorfensulphide, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate, chloroform,
- chloromebuform chloromethiuron, chloropicrin, chloropropylate, chlorphoxim,
- chlorprazophos chlorpyrifos, chlorpyrifos methyl, chlorthiophos, chromafenozide, cinerin I, cinerin II, cismethrin, cloethocarb, clofentezine, closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate, coumaphos, coumithoate, crotamiton, crotoxyphos, cruentaren A&B, crufomate, cryolite, cyanofenphos, cyanophos, cyanthoate, cyclethrin, cycloprothrin, cyenopyrafen, cyflumetofen, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin, cyromazine, cy
- d-limonene dazomet, DBCP, DCIP, DDT, decarbofuran, deltamethrin, demephion, demephion O, demephion S, demeton, demeton methyl, demeton O, demeton O methyl, demeton S, demeton S methyl, demeton S methylsulphon, diafenthiuron, dialifos, diamidafos, diazinon, dicapthon, dichlofenthion, dichlofluanid, dichlorvos, dicofol, dicresyl, dicrotophos, dicyclanil, dieldrin, dienochlor, diflovidazin, diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate, dimethrin, dimethylvinphos, dimetilan, dinex, dinobuton, dinocap, dinocap 4, dinocap 6,
- ecdysterone emamectin, EMPC, empenthrin, endosulfan, endothion, endrin, EPN, epofenonane, eprinomectin, esfenvalerate, etaphos, ethiofencarb, ethion, ethiprole, ethoate methyl, ethoprophos, ethyl DDD, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, etofenprox, etoxazole, etrimfos, EXD,
- imicyafos imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isamidofos, isazofos, isobenzan, isocarbophos, isodrin, isofenphos, isoprocarb, isoprothiolane, isothioate, isoxathion, ivermectin
- jasmolin I jasmolin II
- jodfenphos juvenile hormone I, juvenile hormone II, juvenile hormone III
- naftalofos naled, naphthalene, nicotine, nifluridide, nikkomycins, nitenpyram, nithiazine, nitrilacarb, novaluron, noviflumuron,
- quassia quinalphos, quinalphos, quinalphos methyl, quinothion, quantifies, rafoxanide, resmethrin, rotenone, ryania,
- sabadilla schradan, selamectin, silafluofen, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulcofuron, sulfiram, sulfluramid, sulfotep, sulfur, sulfuryl fluoride, sulprofos,
- tau fluvalinate tau fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane, tetrachlorvinphos, tetradifon, tetramethrin, tetranactin, tetrasul, theta cypermethrin, thiacloprid, thiamethoxam, thicrofos, thiocarboxime, thiocyclam, thiodicarb, thiofanox, thiometon, thionazin, thioquinox, thiosultap, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, trans
- vamidothion vamidothion, vamidothion, vaniliprole, vaniliprole,
- any combination of the above pesticides can be used.
- compositions disclosed in this document may also be used with antimicrobials, bactericides, defoliants, safeners, synergists, algaecides, attractants, desiccants, pheromones, repellants, animal dips, avicides, disinfectants, semiochemicals, and molluscicides (these categories not necessarily mutually exclusive) for reasons of economy, and synergy.
- compositions disclosed in this document can be used with other compounds such as the ones mentioned under the heading "Mixtures” to form further synergistic mixtures where the mode of action of the compositions in the mixtures are the same, similar, or different.
- mode of actions include, but are not limited to: acetyl choline esterase inhibitor; sodium channel modulator; chitin biosynthesis inhibitor; GABA-gated chloride channel antagonist; GABA and glutamate-gated chloride channel agonist; acetyl choline receptor agonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinic acetylcholine receptor; Midgut membrane disrupter; and oxidative phosphorylation disrupter.
- compositions described in this document may also be provided with
- phytologically-acceptable inert ingredients to provide or complement a carrier and can be formulated into, for example, baits, concentrated emulsions, dusts, emulsifiable concentrates, fumigants, gels, granules, microencapsulations, seed treatments, suspension concentrates, suspoemulsions, tablets, water soluble liquids, water dispersible granules or dry flowables, wettable powders, and ultra low volume solutions.
- baits concentrated emulsions, dusts, emulsifiable concentrates, fumigants, gels, granules, microencapsulations, seed treatments, suspension concentrates, suspoemulsions, tablets, water soluble liquids, water dispersible granules or dry flowables, wettable powders, and ultra low volume solutions.
- Pesticide compositions can be frequently applied as aqueous suspensions or emulsions prepared from concentrated formulations of such compositions.
- Such water-soluble, water- suspendable, or emulsifiable formulations are either solids, usually known as wettable powders, or water dispersible granules, or liquids usually known as emulsifiable concentrates, or aqueous suspensions.
- Wettable powders which may be compacted to form water dispersible granules, comprise an intimate mixture of the pesticide composition, a carrier, and surfactants.
- the carrier is usually chosen from among the attapulgite clays, the
- Effective surfactants which can comprise from about 0.5% to about 10% of the wettable powder, are found among sulfonated lignins, condensed naphthalenesulfonates, naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates, and nonionic surfactants such as ethylene oxide adducts of alkyl phenols.
- Emulsifiable concentrates comprise a convenient concentration of a pesticide composition dissolved in a carrier that is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers.
- Useful organic solvents include aromatics, especially xylenes and petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha.
- Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.
- Suitable emulsifiers for emulsifiable concentrates are chosen from conventional anionic and nonionic surfactants.
- Aqueous suspensions comprise suspensions of water-insoluble pesticide compositions dispersed in an aqueous carrier.
- Suspensions are prepared by finely grinding the pesticide composition and vigorously mixing it into a carrier comprised of water and surfactants.
- ingredients such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous carrier. It is often most effective to grind and mix the pesticide composition at the same time by preparing the aqueous mixture and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.
- Pesticide compositions may also be applied as granular formulations that are particularly useful for applications to the soil.
- Granular formulations contain the pesticide composition dispersed in a carrier that comprises clay or a similar substance.
- Such formulations are usually prepared by dissolving the pesticide composition in a suitable solvent and applying it to a granular carrier which has been pre-formed to the appropriate particle size, in the range of from about 0.5 to 3 mm.
- Such formulations may also be formulated by making a dough or paste of the carrier and pesticide composition and crushing and drying to obtain the desired granular particle size.
- Dusts containing a pesticide composition are prepared by intimately mixing the pesticide composition in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock, and the like. Dusts can be applied as a seed dressing, or as a foliage application with a dust blower machine.
- a suitable dusty agricultural carrier such as kaolin clay, ground volcanic rock, and the like. Dusts can be applied as a seed dressing, or as a foliage application with a dust blower machine.
- a pesticide composition in the form of a solution in an appropriate organic solvent, usually petroleum oil, such as the spray oils, which are widely used in agricultural chemistry.
- Pesticide compositions can also be . applied in the form of an aerosol formulation.
- the pesticide composition is dissolved or dispersed in a carrier, which is a pressure-generating propellant mixture.
- the aerosol formulation is packaged in a container from which the mixture is dispensed through an atomizing valve.
- Pesticide baits are formed when the pesticide composition is mixed with food or an attractant or both. When the pests eat the bait they also consume the pesticide composition. Baits may take the form of granules, gels, flowable powders, liquids, or solids. They may be used in or around pest harborages.
- Fumigants are pesticides that have a relatively high vapor pressure and hence can exist as a gas in sufficient concentrations to kill pests in soil or enclosed spaces.
- the toxicity of the fumigant is proportional to its concentration and the exposure time. They are characterized by a good capacity for diffusion and act by penetrating the pest's respiratory system or being absorbed through the pest's cuticle. Fumigants are applied to control stored product pests under gas proof sheets, in gas sealed rooms or buildings or in special chambers.
- Oil solution concentrates are made by dissolving a pesticide composition in a solvent that will hold the pesticide composition in solution.
- Oil solutions of a pesticide composition usually provide faster knockdown and kill of pests than other formulations due to the solvents themselves having pesticidal action and the dissolution of the waxy covering of the integument increasing the speed of uptake of the pesticide.
- Other advantages of oil solutions include better storage stability, better penetration of crevices, and better adhesion to greasy surfaces.
- Another embodiment is an oil-in-water emulsion, wherein the emulsion comprises oily globules which are each provided with a lamellar liquid crystal coating and are dispersed in an aqueous phase, wherein each oily globule comprises at least one compound which is agriculturally active, and is individually coated with a monolamellar or oligolamellar layer comprising: ( 1) at least one non-ionic lipophilic surface-active agent, (2) at least one non- ionic hydrophilic surface-active agent and (3) at least one ionic surface-active agent, wherein the globules having a mean particle diameter of less than 800 nanometers.
- compositions disclosed in this document can also contain other components.
- these components include, but are not limited to, (this is a non-exhaustive and non-mutually exclusive list) wetters, spreaders, stickers, penetrants, buffers, sequestering agents, drift reduction agents, compatibility agents, anti-foam agents, cleaning agents, rheology agents, stabilizers, dispersing agents and emulsifiers. A few components are described forthwith.
- a wetting agent is a substance that when added to a liquid increases the spreading or penetration power of the liquid by reducing the interfacial tension between the liquid and the surface on which it is spreading.
- Wetting agents are used for two main functions in agrochemical formulations: during processing and manufacture to increase the rate of wetting of powders in water to make concentrates for soluble liquids or suspension concentrates; and during mixing of a product with water in a spray tank to reduce the wetting time of wettable powders and to improve the penetration of water into water-dispersible granules.
- wetting agents used in wettable powder, suspension concentrate, and water-dispersible granule formulations are: sodium lauryl sulphate; sodium dioctyl sulphosuccinate; alkyl phenol ethoxylates; and aliphatic alcohol ethoxylates.
- a dispersing agent is a substance which adsorbs onto the surface of particles and helps to preserve the state of dispersion of the particles and prevents them from reaggregating.
- Dispersing agents are added to agrochemical formulations to facilitate dispersion and suspension during manufacture, and to ensure the particles redisperse into water in a spray tank. They are widely used in wettable powders, suspension concentrates and water- dispersible granules.
- Surfactants that are used as dispersing agents have the ability to adsorb strongly onto a particle surface and provide a charged or steric barrier to reaggregation of particles. The most commonly used surfactants are anionic, non-ionic, or mixtures of the two types.
- dispersing agents For wettable powder formulations, the most common dispersing agents are sodium lignosulphonates. For suspension concentrates, very good adsorption and stabilization are obtained using polyelectrolytes, such as sodium naphthalene sulphonate formaldehyde condensates. Tristyrylphenol ethoxylate phosphate esters are also used. Non-ionics such as alkylarylethylene oxide condensates and EO-PO block copolymers are sometimes combined with anionics as dispersing agents for suspension concentrates. In recent years, new types of very high molecular weight polymeric surfactants have been developed as dispersing agents.
- hydrophobic 'backbones' and a large number of ethylene oxide chains forming the 'teeth' of a 'comb' surfactant.
- These high molecular weight polymers can give very good long-term stability to suspension concentrates because the hydrophobic backbones have many anchoring points onto the particle surfaces.
- dispersing agents used in agrochemical formulations are: sodium lignosulphonates; sodium naphthalene sulphonate formaldehyde condensates; tristyrylphenol ethoxylate phosphate esters; aliphatic alcohol ethoxylates; alky ethoxylates; EO-PO block copolymers; and graft copolymers.
- An emulsifying agent is a substance which stabilizes a suspension of droplets of one liquid phase in another liquid phase. Without the emulsifying agent the two liquids would separate into two immiscible liquid phases.
- the most commonly used emulsifier blends contain alkylphenol or aliphatic alcohol with 12 or more ethylene oxide units and the oil- soluble calcium salt of dodecylbenzene sulphonic acid.
- a range of hydrophile-lipophile balance (“HLB”) values from 8 to 18 will normally provide good stable emulsions. Emulsion stability can sometimes be improved by the addition of a small amount of an EO-PO block copolymer surfactant.
- a solubilizing agent is a surfactant which will form micelles in water at
- the micelles are then able to dissolve or solubilize water-insoluble materials inside the hydrophobic part of the micelle.
- the types of surfactants usually used for solubilization are non-ionics: sorbitan monooleates; sorbitan monooleate ethoxylates; and methyl oleate esters.
- Surfactants are sometimes used, either alone or with other additives such as mineral or vegetable oils as adjuvants to spray-tank mixes to improve the biological performance of the pesticide on the target.
- the types of surfactants used for bioenhancement depend generally on the nature and mode of action of the pesticide. However, they are often non-ionics such as: alky ethoxylates; linear aliphatic alcohol ethoxylates; aliphatic amine ethoxylates.
- Organic solvents are used mainly in the formulation of emulsifiable concentrates, ULV formulations, and to a lesser extent granular formulations. Sometimes mixtures of solvents are used.
- the first main groups of solvents are aliphatic paraffinic oils such as kerosene or refined paraffins.
- the second main group and the most common comprises the aromatic solvents such as xylene and higher molecular weight fractions of C9 and CIO aromatic solvents. Chlorinated hydrocarbons are useful as cosolvents to prevent
- Thickeners or gelling agents are used mainly in the formulation of suspension concentrates, emulsions and suspoemulsions to modify the rheology or flow properties of the liquid and to prevent separation and settling of the dispersed particles or droplets.
- Thickening, gelling, and anti-settling agents generally fall into two categories, namely water- insoluble particulates and water-soluble polymers. It is possible to produce suspension concentrate formulations using clays and silicas. Examples of these types of materials, include, but are limited to, montmorillonite, e.g. bentonite; magnesium aluminum silicate; and attapulgite. Water-soluble polysaccharides have been used as thickening-gelling agents for many years. The types of polysaccharides most commonly used are natural extracts of seeds and seaweeds are synthetic derivatives of cellulose.
- guar gum examples include, but are not limited to, guar gum; locust bean gum; carrageenam; alginates; methyl cellulose; sodium carboxymethyl cellulose (SCMC); hydroxyethyl cellulose (HEC).
- SCMC carboxymethyl cellulose
- HEC hydroxyethyl cellulose
- Other types of anti-settling agents are based on modified starches, polyacrylates, polyvinyl alcohol and polyethylene oxide. Another good anti-settling agent is xanthan gum.
- anti-foam agents are often added either during the production stage or before filling into bottles.
- silicones are usually aqueous emulsions of dimethyl polysiloxane while the non-silicone anti-foam agents are water- insoluble oils, such as octanol and nonanol, or silica.
- the function of the anti- foam agent is to displace the surfactant from the air-water interface.
- the actual amount of a pesticide composition to be applied to loci of pests is not critical and can readily be determined by those skilled in the art. In general, concentrations from about 0.01 grams of pesticide per hectare to about 5000 grams of pesticide per hectare are expected to provide good control.
- the locus to which a pesticide is applied can be any locus inhabited by an pest, for example, vegetable crops, fruit and nut trees, grape vines, ornamental plants, domesticated animals, the interior or exterior surfaces of buildings, and the soil around buildings.
- Baits are placed in the ground where, for example, termites can come into contact with the bait. Baits can also be applied to a surface of a building, (horizontal, vertical, or slant, surface) where, for example, ants, termites, cockroaches, and flies, can come into contact with the bait.
- Systemic movement of pesticides in plants may be utilized to control pests on one portion of the plant by applying the pesticides to a different portion of the plant.
- control of foliar-feeding insects can be controlled by drip irrigation or furrow application, or by treating the seed before planting.
- Seed treatment can be applied to all types of seeds, including those from which plants genetically transformed to express specialized traits will germinate. Representative examples include those expressing proteins toxic to invertebrate pests, such as Bacillus thuringiensis or other insecticidal toxins, those expressing herbicide resistance, such as "Roundup Ready” seed, or those with "stacked” foreign genes expressing insecticidal toxins, herbicide resistance, nutrition-enhancement or any other beneficial traits.
- seed treatments with the compositions disclosed in this document can further enhance the ability of a plant to better withstand stressful growing conditions. This results in a healthier, more vigorous plant, which can lead to higher yields at harvest time.
- compositions disclosed in this document are suitable for controlling endoparasites and ectoparasites in the veterinary medicine sector or in the field of animal keeping.
- the compositions are applied here in a known manner, such as by oral administration in the form of, for example, tablets, capsules, drinks, granules, by dermal application in the form of, for example, dipping, spraying, pouring on, spotting on, and dusting, and by parenteral administration in the form of, for example, an injection.
- compositions disclosed in this document can also be employed advantageously in livestock keeping, for example, cattle, sheep, pigs, chickens, and geese. Suitable
- formulations are administered orally to the animals with the drinking water or feed.
- the dosages and formulations that are suitable depend on the species.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Remote Sensing (AREA)
- Physics & Mathematics (AREA)
- Acoustics & Sound (AREA)
- Environmental & Geological Engineering (AREA)
- Geology (AREA)
- General Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Geophysics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR112014026596A BR112014026596A2 (en) | 2012-04-30 | 2013-04-25 | synergistic pesticide composition |
MX2014013204A MX2014013204A (en) | 2012-04-30 | 2013-04-25 | Synergistic pesticidal compositions. |
CA2870031A CA2870031A1 (en) | 2012-04-30 | 2013-04-25 | Synergistic pesticidal compositions |
EP13785277.8A EP2844068A4 (en) | 2012-04-30 | 2013-04-25 | Synergistic pesticidal compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261640423P | 2012-04-30 | 2012-04-30 | |
US61/640,432 | 2012-04-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013165793A1 true WO2013165793A1 (en) | 2013-11-07 |
Family
ID=52145462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2013/038122 WO2013165793A1 (en) | 2012-04-30 | 2013-04-25 | Synergistic pesticidal compositions |
Country Status (7)
Country | Link |
---|---|
US (1) | US20130288897A1 (en) |
EP (1) | EP2844068A4 (en) |
AR (1) | AR090892A1 (en) |
BR (1) | BR112014026596A2 (en) |
CA (1) | CA2870031A1 (en) |
MX (1) | MX2014013204A (en) |
WO (1) | WO2013165793A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109187836A (en) * | 2018-09-21 | 2019-01-11 | 红河哈尼族彝族自治州农产品质量安全检验检测中心 | Overlap of peaks pesticide efficient analysis method out |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017015384A1 (en) | 2015-07-22 | 2017-01-26 | Conocophillips Company | Wavseis sourcing |
CN105481743B (en) * | 2015-11-25 | 2017-09-01 | 南阳师范学院 | A kind of method that sulfilimine is oxidized to sulfoximide |
EP3246313A1 (en) * | 2016-05-19 | 2017-11-22 | Solvay Sa | Process for the manufacture of 2-substituted-5-(1-methylthio)alkylpyridines |
AU2020351837A1 (en) * | 2019-09-26 | 2022-04-21 | Terramera, Inc. | Systems and methods for synergistic pesticide screening |
PE20241633A1 (en) | 2022-01-14 | 2024-08-09 | Enko Chem Inc | PROTOPORPHYRINOGEN OXIDASE INHIBITORS |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100168177A1 (en) * | 2008-12-26 | 2010-07-01 | Dow Agrosciences, Llc | Stable insecticide compositions |
US20100179099A1 (en) * | 2006-02-10 | 2010-07-15 | Loso Michael R | Insecticidal n-substituted (6-halooalkylpyridin-3-yl)-alkyl sulfoximines |
US20110160054A1 (en) * | 2008-08-28 | 2011-06-30 | Basf Se | Pesticidal Mixtures Comprising Cyanosulfoximine Compounds and Spinetoram |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI395736B (en) * | 2006-11-08 | 2013-05-11 | Dow Agrosciences Llc | Heteroaryl (substituted) alkyl n-substituted sulfoximines as insecticides |
AU2009243775B2 (en) * | 2008-05-07 | 2015-05-14 | Bayer Intellectual Property Gmbh | Synergistic active ingredient combinations |
WO2010040623A1 (en) * | 2008-10-08 | 2010-04-15 | Syngenta Participations Ag | Pesticidal combinations containing sulfoxaflor |
EP2223598A1 (en) * | 2009-02-23 | 2010-09-01 | Bayer CropScience AG | Insecticidal compounds with improved effect |
HUE028573T2 (en) * | 2010-02-19 | 2016-12-28 | Dow Agrosciences Llc | Synergistic herbicide/insecticide composition containing certain pyridine carboxylic acids and certain insecticides |
-
2013
- 2013-04-25 BR BR112014026596A patent/BR112014026596A2/en not_active IP Right Cessation
- 2013-04-25 CA CA2870031A patent/CA2870031A1/en not_active Abandoned
- 2013-04-25 WO PCT/US2013/038122 patent/WO2013165793A1/en active Application Filing
- 2013-04-25 MX MX2014013204A patent/MX2014013204A/en unknown
- 2013-04-25 EP EP13785277.8A patent/EP2844068A4/en not_active Withdrawn
- 2013-04-25 US US13/870,096 patent/US20130288897A1/en not_active Abandoned
- 2013-04-29 AR ARP130101464A patent/AR090892A1/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100179099A1 (en) * | 2006-02-10 | 2010-07-15 | Loso Michael R | Insecticidal n-substituted (6-halooalkylpyridin-3-yl)-alkyl sulfoximines |
US20110160054A1 (en) * | 2008-08-28 | 2011-06-30 | Basf Se | Pesticidal Mixtures Comprising Cyanosulfoximine Compounds and Spinetoram |
US20100168177A1 (en) * | 2008-12-26 | 2010-07-01 | Dow Agrosciences, Llc | Stable insecticide compositions |
Non-Patent Citations (1)
Title |
---|
See also references of EP2844068A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109187836A (en) * | 2018-09-21 | 2019-01-11 | 红河哈尼族彝族自治州农产品质量安全检验检测中心 | Overlap of peaks pesticide efficient analysis method out |
Also Published As
Publication number | Publication date |
---|---|
AR090892A1 (en) | 2014-12-17 |
MX2014013204A (en) | 2015-05-20 |
US20130288897A1 (en) | 2013-10-31 |
CA2870031A1 (en) | 2013-11-07 |
EP2844068A1 (en) | 2015-03-11 |
EP2844068A4 (en) | 2015-11-11 |
BR112014026596A2 (en) | 2017-06-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8349815B2 (en) | Synergistic pesticidal mixtures | |
EP2166851B1 (en) | Increasing plant vigor | |
WO2008130651A2 (en) | Diarylisoxazolines | |
WO2009134224A1 (en) | Synergistic pesticidal mixtures | |
WO2009111309A1 (en) | Pesticides | |
US8445500B2 (en) | Pesticidal compositions | |
US20130288897A1 (en) | Synergistic pesticidal compositions | |
US20130065912A1 (en) | Pesticidal compositions | |
AU2008350261B2 (en) | Synergistic pesticidal mixtures |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13785277 Country of ref document: EP Kind code of ref document: A1 |
|
DPE1 | Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101) | ||
ENP | Entry into the national phase |
Ref document number: 2870031 Country of ref document: CA |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: MX/A/2014/013204 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013785277 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112014026596 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112014026596 Country of ref document: BR Kind code of ref document: A2 Effective date: 20141023 |