USH806H - Herbicidal clomazone compositions and methods of use tolerant to corn and other crops - Google Patents

Herbicidal clomazone compositions and methods of use tolerant to corn and other crops Download PDF

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USH806H
USH806H US07/074,383 US7438387A USH806H US H806 H USH806 H US H806H US 7438387 A US7438387 A US 7438387A US H806 H USH806 H US H806H
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clomazone
corn
seeds
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David W. Keifer
John M. Tymonko
Earl D. Felix
William A. Van Saun
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FMC Corp
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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 one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Abstract

Synergistic herbicidal effect is obtained in the application of clomazone together with reduction in the rate of clomazone, by combining clomazone with a photosystem II (PS-II) inhibiting herbicide such as atrazine, cyanazine or linuron. Crops such as corn and other gramineous plants are rendered more tolerant to clomazone and to combinations of clomazone with a PS-II inhibiting herbicide by treatment of the crops or crop seeds with a safener such as 1,8-naphthalic anhydride.

Description

TECHNICAL FIELD

This invention relates to the control of undesirable vegetation encountered in the cultivation of various plant species, particularly agronomic gramineous crops.

BACKGROUND OF THE INVENTION

The compound 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, hereinafter referred to by the common name "clomazone", is a potent herbicide as evidenced by its ability to control, for full growing seasons and at low application rates in soybean stands, a broad spectrum of grasses and broadleaf weeds that compete with soybeans. As with many herbicides, however, clomazone is not as quickly metabolized by some crops, trees and ornamentals as it is by soybeans. Such intolerance can result temporarily in unsightly yellowing or whitening of the plants unless precautions are taken to prevent or minimize exposure. These precautions include control of surface spraying to forestall drift to adjacent fields planted with low tolerance crops, incorporation into soil during tillage to avoid volatilization due to high temperature and/or moisture, rotation to sensitive crops after specified periods of time following application of clomazone, and thorough cleaning of spray tanks to avoid contaminating other chemicals.

Although good agronomy dictates use of one or more of the foregoing practices at all times, it will be evident that measures that will permit reduction in rates of application of clomazone or which otherwise will increase the tolerance of desirable plants to clomazone without substantial diminution of herbicidal efficacy against weeds, will greatly expand the usefulness of clomazone and ultimately result in lower cost. For example, because corn is sensitive to clomazone, clomazone cannot be used to combat weeds in corn stands. To prevent carryover, fields treated with clomazone cannot be rotated to corn for at least nine months after application of clomazone. Other gramineous crops are similarly disadvantaged.

In this specification the term "crops" includes not only agronomic crops but plants of all kinds, and the term "gramineous" includes both cereal and non-cereal grassy crops, such as corn, wheat, oats, barley, rice, cotton, sorghum and sugar cane.

SUMMARY OF THE INVENTION

It has now been found, in one aspect of the invention, that by combining clomazone treatment and treatment with one or more photosystem II (hereafter abbreviated "PS-II") inhibiting herbicides, the rate of clomazone application may be substantially reduced without loss of herbicidal activity, accompanied by substantially improved tolerance towards gramineous crops heretofore damaged by clomazone, such as corn. The discovery thereby opens up applicability of clomazone to control of weeds in crops other than soybeans, such as corn, sorghum, sugar cane, barley, wheat, oats, cotton, lima beans and other gramineous crops.

In another aspect of the invention, the protection of corn and other gramineous crops is maximized by treatment with a safener prior to exposure to clomazone alone or with a PS-II inhibiting herbicide.

In still another aspect, specific PS-II inhibiting herbioides, selected from one or more of triazine and urea herbicides, including mixtures thereof, are synergistically combined with clomazone either by admixture prior to application, or by separate application. Both clomazone and the co-herbicide, when combined, thereby become effective at lower rates of application for weed control in a variety of crops including gramineous crops such as corn.

DETAILED DESCRIPTION

Clomazone is described in U.S. Pat. No. 4,405,357 issued Sept. 30, 1983 to J. H. Chang, specifically Example 16 thereof. PS-II inhibiting herbicides are a well known class of herbicides characterized by ability to inhibit the conversion of light energy into chemical energy during the process of photosynthesis in the chloroplast. This inhibiting action has also been described as the blocking of electron transport in the photosystem II pathway to photosynthesis. Herbicidal activity of the PS-II inhibiting type is in contrast to herbicidal action characterized by direct or indirect interference with synthesis of the carotenoid protectants of chlorophyll. Herbicides which operate by the latter mechanism are also known as "bleaching herbicides". PS-II inhibiting herbicides and the bleaching herbicides are discussed and described in various publications including C. Feldtke, Biochemistry and Physiology of Herbicide Action, Springer-Verlag (New York 1982), 202 pages, particularly pages 18-51 and 99-111. The latter text is incorporated herein by reference.

Unlike the well-known bleaching herbicides, clomazone is, in addition to being a bleaching herbicide, an inhibitor of the synthesis of chlorophyll.

As apparent from the Feldtke text, pages 18-51, PSII inhibiting herbicides include the following classes of compounds: ureas, anilides, s-triazines, as-triazinones, uracils, biscarbamates, pyridazinones, hydroxybenzonitriles, nitrophenols, benzimidazoles, quinoids, and miscellaneous compounds not classifiable by structure. All of these compounds are believed to be useful as co-herbicides with clomazone in the present invention. Of the PS-II inhibitors the triazines and ureas are preferred to date, as represented by cyanazine, atrazine and linuron.

The PS-II inhibiting herbicide and clomazone are formulated and applied in accordance with procedures standard in herbicidal treatments as modified by the labels established for each of the active ingredients and by the discoveries of the present invention. Generally, the herbicides are applied in dilute form with an agriculturally acceptable, relatively inert, solid or liquid carrier. Since, as is well known, the formulation and mode of application of a herbicide may affect activity in a given application, the herbicides may be formulated separately or in admixture as emulsifiable concentrates (EC's), as granules preferably of relatively large particle size, as wettable powders, as solutions or suspensions, or in other forms.

To obtain the benefits of the invention, the amount of the PS-II inhibiting herbicide will be in excess of the amount of clomazone, on the order of two to three times by weight as much, or more, of the PS-II inhibiting herbicide as clomazone. Optimum ratios are routinely determined for the particular PS-II inhibiting herbicide selected for combination with clomazone. For example, it has been found that in the case of atrazine, the ratio of atrazine to clomazone should be at least about 2:1 by weight but may range as high as about 15:1 by weight or more. Keeping in mind such ratios, the herbicides may be formulated singly or in admixture to contain between about 0.01% and 95% by weight active ingredient, the balance being a carrier (one or more) together, in some formulations, with a surface active agent. Typically, the carrier will comprise about 4-98% by weight of the formulation and a surface active agent about 1-15% by weight.

Emulsifiable concentrates are homogeneous liquid or paste compositions dispersible in water or other dispersant, and may consist entirely of a compound of this invention with a liquid or solid emulsifying agent, or may also contain an agriculturally acceptable liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile and other non-volatile organic solvents. For example, a useful emulsifiable concentrate formulation, designated "4EC' because it contains four pounds of active ingredient per gallon of concentrate (0.479 kg/liter), contains 53.01 parts of clomazone, 6.0 parts of a blend of alkylnaphthalenesulfonate and polyoxyethylene ethers and emulsifiers, 1.0 part of epoxidized soybean oil as stabilizer, and as solvent 39.99 parts of petroleum distillate having a high flash-point.

Granular formulations are particularly useful for aerial distribution. Useful granular formulations may be of several types. Impregnated granules are those wherein the active ingredient is applied to large particles of an absorbent carrier, such as an attapulgite or kaolin clay, corncobs, expanded mica, normally in the form of a solution in a solvent. Surface-coated granules may be produced by spraying the molten active ingredient onto the surface of a generally nonabsorbent particle or by spraying on a solution of active ingredient in a solvent. The core may be water-soluble such as sand, marble chips or coarse talc. Particularly useful is a granule wherein a wettable powder is applied as a surface coating to a sand or other insoluble particle such that the wettable powder may be dispersed on contact of the granule with moisture. Granules may be produced by agglomeration of dusts or powders by compaction rollers, by extrusion through a die or by use of a granulating disc. Granular formulations may vary widely in concentration, with useful formulations containing as little as 0.5% or as much as 95% of active ingredient.

Wettable powders, also useful formulations for preemergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersants. The wettable powder is ultimately applied to the soil as a finely divided dry material or as an emulsion in water or other liquid. Typical carriers for wettable powders include fuller's earth, kaolin clays, silicas and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5% to 80% of active ingredient, depending on the absorbability of the active ingredient and on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.

Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, for example, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; polyethylene oxides; sulfonated oils, fatty acid esters of polyhydric alcohols; and other types of surface active agents, many of which are available commerce.

As indicated, the PS-II inhibiting herbicide may be incorporated into the same formulation with clomazone or may be separately formulated in the same manner as clomazone.

The formulations may be applied without further dilution or as dilute solutions, emulsions or suspensions in water or other suitable diluent. The compositions may be applied to the area wherein control is desired, prior to emergence in the case of agronomic gramineous to crops, by spraying onto the surface of the soil in the case of liquid compositions or by distribution from mechanical equipment in the case of solids. It may be preferable to blend clomazone formulation into the upper layer of soil by cultivation.

The active herbicidal compounds of the invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, and other agricultural chemicals. In applying the active compounds of this invention, whether formulated alone or with other agricultural chemicals, an effective amount of each active ingredient is employed. The amount constituting an effective amount is variable, depending on the ratio of PS-II inhibiting herbicide to clomazone and other factors such as the type of soil, the expected pattern of rainfall or irrigation, the plant species to be controlled, and the gramineous crop, if any, to be grown. Generally, a uniform application of from about 0.01 to about 0.5 kilograms per hectare of clomazone will be employed, more preferably, from 0.06 to 0.4 kilograms per hectare. The PS-II inhibiting herbicide rate of application in the case of atrazine may range from about 0.04 to about 2.0 kilograms per hectare, more preferably about 0.3 to 1.5 kilograms per hectare. The same or other rates may be used for other PS-II inhibiting herbicides. Generally, the rate of application in the field will be about 2 to 4 times that in the greenhouse.

Crops protected by appropriate rates of application of the combined treatment include gramineous crops such as sorghum, sugar cane, and corn (field, sweet, popcorn). Protection is further enhanced, particularly in the case of certain corn hybrids or other desirable plants sensitive to clomazone, by application of a safener (also known as an antidote). A safener effective for this purpose is 1,8-naphthalic anhydride (hereafter sometimes abbreviated as "NA"). Other safeners are described in the literature such as K.K. Hatzios, Herbicide Antidotes: Development, Chemistry, and Mode of Action, Advances In Agronomy, vol. 36, 265-315, Academic Press, 1983; and C. Parker, Herbicide Antidotes--A Review, Pestic. Sci., 14,440-48 (1983). These articles are incorporated herein by reference. The safener is applied in the same manner as a herbicide, i.e., formulated as an emulsifiable concentrate, wettable powder, granules, suspension or a solution. The safener may be applied as a coating to crop seed or seed of other desirable plants, preemergently to the locus of a plant to be protected or, in some cases, to the plant itself. Preferably, the safener is applied prior to exposure to clomazone. Safening amounts will vary according to the gramineous plant to be protected, soil conditions, and the rate of application of clomazone. For corn seed, about 0.05% to 1.5% by weight, preferably about 0.1% to 0.5% by weight, on weight of seed is effective.

Herbicidal Evaluation

The herbicidal compositions of the invention were evaluated in a laboratory greenhouse as described below. Atrazine was evaluated as a representative PS-II inhibiting herbicide. In a first series of tests (Series A, Tables 1 and 2) the tolerance to clomazone of various crops was studied relative to treatment with 1,8-naphthalic anhydride. In a second series of tests (Series B, Tables 3, 3A and 4) the effect of combined treatments with clomazone and atrazine was studied, again relative to protection with 1,8-naphthalic anhydride.

The formulations in the Series B tests were as follows where the clomazone formulation was a 4.0 lb/gal emulsifiable concentrate (identified below as "4 EC") and the atrazine formulation was an 80% wettable powder (identified as "80 WP").

______________________________________             % wt/wt______________________________________Clomazone (88.9% technical)               52.40Emulsifier A        5.60Emulsifier B        1.40Carrier/diluent     40.60______________________________________

Emulsifier A is a blend of the anionic calcium salt of dodecyl benzene sulfonate and a nonionic 30 molar ethylene oxide condensation product of nonylphenol. Emulsifier B is a nonionic paste of 100% polyalkylene glycol ether. The carrier/diluent is a refined xylene with a high flash point.

An 80% wettable powder (80 WP) formulation of atrazine was used. A typical 80 WP formulation is the following:

______________________________________              % wt/wt______________________________________Atrazine (technical) 80.00Base                 20.0096.00% carrier/diluent 2.00% wetting/dispersing agent 2.00% dispersing agent______________________________________

The wetting/dispersing agent is powdered sodium alkylnaphthalene sulfonate. The dispersing agent is highly purified sodium lignosulfonate. The carrier/diluent is kaolin clay.

A. Improved Tolerance of Crops to Clomazone by Safening

Seeds of field corn (Zea mays) were treated with 1,8-naphthalic anhydride in the following manner.

An appropriate amount of tap water was placed in a low-shear, three-paddled mixer and, with mixing, an amount of the sticker sodium carboxyl methyl cellulose to provide a 2% (wt/wt) solution was added slowly to avoid the formation of agglomerates. The appropriate amount of field corn seeds needed for the test were placed in a clean rotating drum mixer, and the required amount of the aqueous sticker solution to provide a 2% (wt/wt) application of the sticker to the seeds was slowly added. The seed-sticker combination was rotated until the seeds were thoroughly wetted. Aliquots of the seed-sticker combination were then rotated with the required amounts of 1,8-naphthalic anhydride to provide concentrations of 0.5, 1.0, and 1.5% (wt/wt). The process was repeated with seeds of sweet corn, sorghum (Sorghum vulgare), barley (Hordeum vulgare), spring and winter wheat (Triticum aestivum), oats (Avena sativa), cotton (Gossypium hirsutum), lima beans (Phaseolus lunatus), and the weeds morningglory (Ipomoea spp), and wild cane (Saccharum spontaneum).

Clomazone was tested with the seeds as treated above and with untreated seeds in a standard preemergence herbicidal evaluation as follows.

Two disposable fiber flats (8 cm×15 cm×25 cm) for each rate of application of clomazone were filled to an approximate depth of 6.5 cm with a steam-pasteurized sterilized sandy loam soil. The soil was leveled and impressed with a template that provided eight evenly spaced furrows in each flat that were 13 cm long and 0.5 cm deep. The treated seeds of the appropriate test plant species were planted in the furrows of the flats. The eight row template was again employed to firmly press the seeds into place. A topping soil prepared by mixing equal portions of sand and sandy loam soil was placed uniformly on top of each flat to a depth of approximately 0.5 cm.

In the standard preemergence herbicidal evaluation clomazone was tested as solutions of 1:1 water:acetone. The test solutions were prepared by dissolving the appropriate amount of technical clomazone in the 1:1 acetone:water solvent to give a solution of the highest rate of application needed for the test. Aliquots of this solution were serial diluted with 1:1 acetone:water to provide solutions of the lower rates of application. The test solutions of clomazone were sprayed onto the surface of the soil in the disposable fiber flats to provide rates of application of 2.0 kg/ha and submultiples thereof to 0.0625 kg/ha. The low rate of application was sprayed first so as not to contaminate the spray equipment. Flats of seeds not treated with 1,8-naphthalic anhydride were also sprayed in an identical manner. In addition, flats of seeds treated with 1,8-naphthalic anhydride and not sprayed with clomazone were also included in the tests. The treated and untreated flats were placed in a greenhouse where they were watered regularly at the soil surface for a period of 21 days. At this time the phytotoxicity of clomazone to the plants from the treated and untreated seeds was recorded. Individual plant species were examined for percent kill and a vigor rating of 1 to 5 was assigned to the surviving plants, a vigor rating of 5 signifying no chemical injury. An injury rating using the percent kill and the vigor rating for each plant species in the tests was calculated using the formula set forth in the footnotes to Table 1 (appended).

Utilizing the injury ratings calculated, the increased tolerance of the test plants from seeds safened with 1,8-naphthalic anhydride as compared to the test plants from unsafened seeds was calculated in terms of percent reduction of injury using the formula set forth in the footnotes to Table 1 (appended).

Two tests were conducted to ascertain the tolerance to clomazone of certain plant species grown from seeds safened with 1,8-naphthalic anhydride using the methods described above.

In test 1, clomazone was applied at rates of 2.0 kg/ha, 1.0 kg/ha, 0.5 kg/ha and 0.25 kg/ha in a preemergence manner to soil containing the seeds of sweet and field corn, sorghum, barley, wheat, oats, cotton and lima beans both untreated and treated with 0.5% (wt/wt) and 1.0% 1,8-naphthalic anhydride. The test results (Table 1 appended) show that tolerance of both field and sweet corn to clomazone was increased at all rates of application of clomazone and at both concentrations of 1,8-naphthalic anhydride applied to the seeds. The best tolerance of corn to clomazone appeared to be at the application rates of 0.25-1.0 kg/ha to seeds treated with 1.0% (wt/wt) 1,8-naphthalic anhydride. Injury to the corn under these conditions was reduced by 52 to 100% (100% being completely tolerant).

The tolerance of wheat, barley, and sorghum to clomazone was increased when the seeds were treated with both 0.5% and 1.0% 1,8-naphthalic anhydride. However, the improved tolerance occurred only at the lowest application rate of clomazone (0.25 kg/ha).

The tolerance of oats, cotton, and lima beans to clomazone was least affected by treatment of their seeds with 1,8-naphthalic anhydride.

In test 2, clomazone was applied at rates of 2.0 kg/ha, 1.0 kg/ha, 0.5 kg/ha, 0.25 kg/ha, 0.125 kg/ha and 0.0625 kg/ha in a preemergence manner to soil containing the seeds of field and sweet corn, sorghum, barley, spring and winter wheat, morningglory, and wild cane untreated and treated with 0.5% (wt./wt), 1.0%, and 1.5% 1,8-naphthalic anhydride. The test results (Table 2 appended) show that tolerance of both field and sweet corn to clomazone was increased at all rates of application of clomazone and at all concentrations of 1,8-naphthalic anhydride applied to the seeds. The best tolerance of corn to clomazone appeared to be at the application rates of 0.0625-0.5 kg/ha regardless of the concentration of 1,8-naphthalic anhydride applied to the seeds. Injury to the corn was reduced 100% at the clomazone application rates of 0.0625 kg/ha and 0.125 kg/ha on seeds treated with either 0.5%, 1.0% or 1.5% 1,8-naphthalic anhydride.

Tolerance of winter and spring wheat to clomazone was improved by the seed treatments, but not to the extent of the improvement in the tolerance of corn.

There was no evidence of phytotoxicity to the seeds or plants grown from these seeds when 1,8-naphthalic anhydride was used as a seed treatment.

B. Reduced clomazone Rate by Combined Herbicide Treatment of Safened and Unsafened Corn

Clomazone was tested at application rates of 0, 0.01, 0.04, 0.08, and 0.32 kg/ha alone and in combination with atrazine at application rates of 0, 0.04, 0.15, 0.3, and 1.2 kg/ha on corn whose seeds were optionally treated with 1,8-naphthalic anhydride. The corn seed for the portion of the test requiring treatment with 1,8-naphthalic anhydride was processed in the following manner:

Seeds, 200 grams each, of two commercial corn hybrids, Funks* 4522 and Pioneer®3732, were placed in 32 oz wide-mouth, screw-lid glass jars. Into each glass jar was also placed 1.0 gram of technical grade 1,8-naphthalic anhydride. The lids were placed on each jar and the jars were rolled on their sides at 160 rpm for 20 minutes on a machine with rubber rollers. The resultant seeds were uniformly coated with 0.5% (wt/wt) 1,8-naphthalic anhydride.

A series of stock solutions containing clomazone or atrazine were prepared in the following manner:

From a clomazone 4 EC formulation 7.6 grams was dissolved with mixing in 160 mL of distilled water. An 80 mL aliquot of this solution was removed and set aside for use as the 0.32 kg/ha rate of application of clomazone. The remaining 80 mL aliquot was diluted with an additional 80 mL of water. The 160 mL solution was mixed and divided into two 80 mL aliquots. One 80 mL aliquot was discarded since the 0.16 kg/ha rate was not used in this test. The remaining 80 mL aliquot was diluted as described above to provide solutions for the 0.08 and the 0.04 kg/ha rate of application of clomazone. One additional solution was prepared by dissolving 0.239 gram of the formulation of clomazone as described above in 160 mL of water to provide the 0.01 kg/ha rate of application of clomazone.

From an atrazine 80 WP formulation a solution for a 1.2 kg/ha rate of application was prepared by dissolving 17.09 grams of the formulated material in 160 mL of distilled water. The solutions for the 0.3, 0.15, and the 0.04 kg/ha rates of application of atrazine were prepared by dissolving 4.27 grams of the formulated atrazine in 160 mL of distilled water. The solution was divided into two 80 mL aliquots and serially diluted as described above.

The appropriate test solutions as described above were used to prepare spray solutions for the chemical application. Thus, 4.0 mL of each of the clomazone solutions or 4.0 mL of each of the atrazine solutions were pipetted into Erlenmeyer flasks. The volume of each was brought to 80 mL by the addition of distilled water to provide the spray solutions of clomazone or atrazine at the rates of application described. The spray solutions for the combination tests of clomazone and atrazine were also prepared in the same manner; that is by combining 4.0 mL of the appropriate clomazone test solution with 4.0 mL of the appropriate atrazine solution and diluting to 80 mL with distilled water.

To establish the herbicide test, plastic flats (36 cm×13 cm×6.5 cm) were filled to an approximate depth of 4.0 cm with a steam-pasteurized loam soil, and the soil was leveled in the flats. A moving belt spray machine was calibrated to deliver at the rate of 30 gallons of spray solution per acre, at a spray pressure of 43 PSI through a nozzle delivering a fine spray. Into this spray machine were placed six of the above flats of soil. The spray reservoir was filled with one of the 80 mL spray solutions prepared above. The spray machine applied the spray solution to the surface of the soil in the flats and then delivered the flats to a chamber where the solvent evaporated. This process was repeated until all the spray solutions had been applied to a group of six flats of soil.

The groups of six flats that had been treated with one spray solution were dumped together into a five gallon metal can that was mounted at an angle on a rotating base and which contained a stationary paddle. The soil was thoroughly mixed by rotating the metal can for three minutes. Six 250 mL beakers of soil were removed and set aside for later use in covering the seeds. The remaining soil was evenly divided and placed back into the six original flats.

The soil in the flats was leveled and pressed with a template that provided eight evenly spaced furrows in the flat that were 10 cm long and about 0.5 cm deep. Seeds of the following species were placed in this order in the respective furrows, with the corn being either treated or untreated with 1,8-naphthalic anhydride as described above: field corn (Zea mays) Funk's hybrid 4522, field corn (Zea mays) Pioneer hybrid 3732, pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), lambsquarter (Chenopodium album), crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis) and barnyardgrass (Echinochloa crusgalli). The eight row template was used again to press the seeds firmly into the soil at the bottom of the furrow. The soil which had been set aside after the soil mixing operation was now used to cover the seeds in the flats. Care was taken to match the topping soil with the flats that contained the same herbicide treatment from which that soil had been removed. One 250 mL beaker of soil was spread over each flat, leveled and pressed firmly down.

The flats were divided into three sets of replicate treatments, and placed in the greenhouse grouped by replicate and arranged within those groupings according to a series of randomly generated numbers. At that time the flats were thoroughly watered from the top and were subsequently surface watered three times per day. Two weeks after planting, phytotoxicity of each of the herbicide combinations was evaluated separately for each species by a visual judgement of percent kill.

The test results are set forth in Tables 3 and 3A (appended), from which it is readily apparent that the tolerance of corn to clomazone, at rates of application of clomazone that would otherwise be damaging, can be greatly increased by the treatment of the corn seeds with 1,8-naphthalic anhydride. For example, at an application rate of 0.32 kg/ha of clomazone, the injury to corn was reduced by 74% when the corn seeds were treated with 0.5% (wt/wt) of 1,8-naphthalic anhydride.

Readily apparent, also, is that when clomazone is applied in combination with atrazine a better, broader spectrum of weed control in corn plots is realized than when either of the two herbicides are applied alone. For example, at an application rate of 0.08 kg/ha, clomazone alone controls 64% and 75% of the broadleaf and grass weed species, respectively. At an application rate of 0.04 kg/ha, atrazine alone controls 24% and 8% of the broadleaf and grass weed species, respectively. However, when a combination of clomazone and atrazine (each at the same rates of application as the individual applications) was applied, the control of broadleaf weed species was increased to 81% and the control of grass weed species was increased to 92%.

The synergism of this effect was verified by subjecting the weed injury data to analysis by Limpel's formula as set forth in the footnote to Table 4. Limpel's formula is discussed in "Weed Control Dimethylchloroterephthalate Alone and In Certain Combinations," Limpel et al, Proc. NEWCC, 16, 48-53 (1962).

When the observed weed injury exceeds the weed injury which would have been expected using Limpel's formula, synergism is demonstrated. Thus, at an application rate of 0.08 kg/ha of clomazone in combination with 0.15 kg/ha of atrazine, Limpel's formula would predict 73% mean broadleaf weed injury and 77% mean grass weed injury. In reality the combination of clomazone and atrazine at the aforementioned rates of application caused 81% mean broadleaf weed injury and 92% mean grass weed injury. As shown in Table 4 (appended) combinations of clomazone and atrazine at other rates of application are also synergistic when subjected to Limpel's formula.

The synergistic effect as evidenced above allows lower rates of application of a combination of clomazone and atrazine than would be equally efficacious if these two herbicides were used individually.

                                  TABLE 1__________________________________________________________________________Increased Tolerance of Crops to Clomazone Using SeedsTreated with 1,8-Naphthalic Anhydride (NA)Test 1                          Percent Reduction of        Injury* to crops  Injury* to crops grown        grown from seeds  from seeds treated        treated with 0.5%                 Injury* to                          with NA as compared Rate of        (wt/wt) and 1.0%                 crops grown                          to crops grown fromCrop  Application        (wt/wt) NA                 from seeds not                          seeds not treatedSpecies of Clomazone        0.5% 1.0%                 treated with NA                          0.5%  1.0%__________________________________________________________________________Field corn 0.25 kg/ha        12    0   63      81    100Sweet corn    0    0   63      100   100Sorghum      55   12   93      41    87Barley       12   12   48      75    75Wheat        48   12   96      50    88Oats         30   12   12      0     0Cotton       12   12   12      0     0Lima beans   12   100  0       0     0Field corn 0.5 kg/ha        12   12  100      88    88Sweet corn   12   12   99      88    88Sorghum      100  98  100      0     2Barley       99   89   95      0     6Wheat        99   100 100      1     0Oats         78   48   78      0     38Cotton       21   99   99      79    0Lima beans   12   63   12      0     0Field corn 1.0 kg/ha        25   12  100      75    88Sweet corn   48   12  100      52    88Sorghum      100  100 100      0     0Barley       100  99  100      0     1Wheat        100  100 100      0     0Oats         100  99  100      0     1Cotton       100  100 100      0     0Lima beans   12   100  70      83    0Field corn 2.0 kg/ha        90   78  100      10    12Sweet corn   90   85  100      10    15Sproghum     100  100 100      0     0Barley       100  100 100      0     0Wheat        100  100 100      0     0Oats         100  100 100      0     0Cotton       100  100 100      0     0Lima beans   95   63   70      0     10__________________________________________________________________________ *Injury = percent kill + X(100 - percent kill) X = Vigor 1 = 1    Vigor 2 = 0.75    Vigor 3 = 0.25    Vigor 4 = 0.12    Vigor 5 = 0 ##STR1##

                                  TABLE 2__________________________________________________________________________Increased Tolerance of Crops and Weeds to ClomazoneUsing Seeds Treated with 1,8-Naphthalic Anhydride (NA)Test 2                            Percent Reduction                            of Injury** to Plants         Injury* to plants  grown from seeds         grown from seeds   treated with NA as         treated with                   Injury* to                            compared to plants  Rate of         0.5% (wt/wt)                   plants grown                            grown from seedsCrop   Application         1.0% and 1.5% NA                   from seeds not                            seeds not treatedSpecies  of Clomazone         0.5%            1.0%               1.5%                   treated with NA                            0.5%                                1.0%                                   1.5%__________________________________________________________________________Field corn  0.0625 kg/ha         0  0  0   40       100 100                                   100Sweet corn    0  0  0   12       100 100                                   100Sorghum       12 25 12  12       0   0  0Barley        12 25 25  12       0   0  0Sp-Wheat      12 12 12  25       52  52 52W-Wheat       12 12 12  25       52  52 52Morningglory  12 25 12  12       0   0  0Wild cane     0  12 12  12       100 0  0Field corn  0.125 kg/ha         0  0  0   70       100 100                                   100Sweet corn    0  0  0   38       100 100                                   100Sorghum       25 12 48  93       73  87 48Barley        78 78 78  48       0   0  0Sp-Wheat      48 55 70  70       31  21 0W-Wheat       48 25 55  78       38  68 29Morningglory  12 85 12  12       0   0  0Wild cane     12 12 38  25       52  53 0Field corn  0.250 kg/ha         12 12 0   100      88  88 100Sweet corn    12 12 12  83       86  86 86Sorghum       98 55 63  100      2   45 37Barley        85 85 85  85       0   0  0Sp-Wheat      85 85 55  99       14  14 44W-Wheat       85 85 55  99       14  14 44Morningglory  12 55 85  12       0   0  0Wild cane     12 70 55  99       88  20 44Field corn  0.5 kg/ha         12 12 12  100      88  88 88Sweet corn    12 12 12  83       86  86 86Sorghum       98 98 100 100      2   2  0Barley        100            100               98  85       0   0  0Sp-Wheat      85 85 98  99       14  14 1W-Wheat       70 85 98  99       29  14 1Morningglory  56 47 85  70       20  33 0Wild cane     25 100               98  100      0   2  0Field corn  1.0 kg/ha         65 25 25  100      35  75 75Sweet corn    38 25 48  100      62  75 52Sorghum       99 100               100 100      1   0  0Barley        98 100               100 100      2   0  0Sp-Wheat      98 98 100 100      2   0  0W-Wheat       100            100               100 100      0   0  0Morningglory  65 78 85  99       34  21 14Wild cane     99 100               100 100      1   0  0Field corn  2.0 kg/ha         88 90 90  100      12  10 10Sweet corn    95 100               100 100      5   0  0Sorghum       100            100               100 100      0   0  0Barley        100            100               100 100      0   0  0Sp-Wheat      100            100               100 100      0   0  0W-Wheat       100            100               100 100      0   0  0Morningglory  70 99 99  100      30  1  1Wild cane     98 100               100 100      2   0  0__________________________________________________________________________ *Injury  same as Table 1 **Percent reduction of injury  same as Table 1

                                  TABLE 3__________________________________________________________________________Efficacy of Clomazone in Combination with Atrazine on Corn Using SeedTreatedwith 1,8-Naphthalic Anhydride (NA) and Untreated Seeds      Corn Seeds             Percent KillRate of Rate of      Treated with             Corn.sup.1                 Green                                            Barn-Appln. of Appln. of      0.5% NA             Funks                 Pioneer   Velvet-                                Lambs-                                    Crab-                                        Fox-                                            yard-Clomazone Atrazine      No Yes G4522                 3732 Pigweed.sup.2                           Leaf quarter                                    grass                                        tail                                            Grass__________________________________________________________________________0 kg/ha 0 kg/ha      X      0   0    0    1    0   0   0   0         X   0   00.01  0    X      0   0    1    38   0   35  19  19         X   0   00.04  0    X      15  0    46   74   37  66  67  69         X   11  00.08  0    X      91  6    46   89   58  69  67  88         X   3   20.32  0    X      99  98   57   98   96  90  92  98         X   35  160     0.04 X      0   0    8    59   4   12  7   7         X   0   00     0.15 X      0   0    13   38   90  79  63  82         X   0   00     0.3  X      0   0    100  94   97  85  70  84         X   0   00     1.2  X      0   0    97   99   99  98  93  95         X   0   00.01  0.04 X      0   0    4    72   9   50  27  33         X   0   00.01  0.15 X      0   0    79   87   93  82  66  68         X   0   00.01  0.3  X      0   0    94   99   100 93  77  83         X   0   00.01  0.2  X      0   0    100  99   100 98  95  97         X   0   00.04  0.04 X      2   0    8    72   16  82  75  79         X   0   00.04  0.15 X      2   0    74   99   95  90  78  84         X   0   00.04  0.3  X      42  24   99   100  99  93  89  95         X   3   20.04  1.2  X      20  2    89   99   100 99  97  98         X   0   00.08  0.04 X      50  5    55   89   99  95  88  92         X   0   00.08  0.15 X      83  5    99   100  100 97  92  90         X   1   00.08  0.3  X      48  3    98   99   100 95  87  93         X   0   00.08  1.2  X      87  37   100  100  99  97  99  98         X   2   00.32  0.4  X      100 100  100  100  100 100 100 100         X   84  500.32  0.15 X      99  94   100  100  100 100 100 100         X   53  500.32  0.3  X      99  98   98   100  100 100 100 100         X   50  330.32  1.2  X      99  98   100  100  100 100 100 100         X   23  8__________________________________________________________________________ .sup.1 The percent kill of corn is derived from the average of three replicates. .sup.2 The percent kill of the weed species is derived from the average o six replicates, three from flats containing corn seeds treated with NA an three from flats containing corn seeds not treated with NA.

                                  TABLE 3A__________________________________________________________________________Summary of Efficacy of Clomazone in Combination with Atrazine on CornUsing Seeds Treated with 1,8-Naphthalic Anhydride (NA) And UntreatedSeedsRate of  Rate of        Corn Seeds Treated                  Percent KillApplication  Application        with 0.5% NA                  Mean Corn.sup.1                         Mean Broadleaf.sup.2                                  Mean Grass.sup.3of Clomazone  of Atrazine        No   Yes  Injury Weed Injury                                  Weed Injury__________________________________________________________________________0 kg/ha  0 kg/ha        X         0      0        0             X    00.01   0     X         0      13       24             X    00.04   0     X         8      52       67             X    00.08   0     X         49     64       75             X    20.32   0     X         99     83       93             X    260      0.04  X         0      24       8             X    00      0.15  X         0      47       75             X    00      0.3   X         0      97       80             X    00      1.2   X         0      98       95             X    00.01   0.04  X         0      29       36             X    00.01   0.15  X         0      86       72             X    00.01   0.3   X         0      98       84             X    00.01   1.2   X         0      99       97             X    00.04   0.04  X         1      32       79             X    00.04   0.15  X         1      89       84             X    00.04   0.3   X         24     99       92             X    20.04   1.2   X         11     96       98             X    00.08   0.04  X         28     81       92             X    00.08   0.15  X         44     100      93             X    10.08   0.3   X         26     99       92             X    00.08   1.2   X         62     100      98             X    10.32   0.04  X         100    100      100             X    670.32   0.15  X         97     100      100             X    520.32   0.3   X         99     99       100             X    420.32   1.2   X         99     100      100             X    16__________________________________________________________________________ .sup.1 The mean corn injury is the average of the percent kill of both varieties of corn from Table 3. .sup.2 The mean broadleaf weed injury is the average of the percent kill of the pigweed, velvetleaf, and lambsquarter from Table 3. .sup.3 The mean grass weed injury is the average of the percent kill of the crabgrass, green foxtail, and the barnyardgrass from Table 3.

              TABLE 4______________________________________Synergistic Herbicidal Activity From Combinationsof Clomazone with Atrazine           Percent Kill                 Mean Broadleaf                             Mean GrassRate of Appl'n     Rate of Appl'n                 Weed Injury Weed Injuryof Clomazone     of Atrazine O.sup.1 E.sup.2                               O.sup.1                                     E.sup.2______________________________________0.01 kg/ha     0 kg/ha     13            240         0.04        24             80.01      0.04        29      34     36*  300.01      0           13      240         0.15        47      750.01      0.15         86*    54    72    810.01      0           13            240         0.3         97            800.01      0.3         98      97    84    950.01      0           13            240         1.2         98            950.01      1.2         99      98    97    960.04      0           52            670         0.04        24             80.04      0.04        32      64     79*  700.04      0           52            670         0.15        47            750.04      0.15         89*    79    84    920.4       0           52            670         0.3         97            800.04      0.3         99      99    92    930.04      0           52            670         1.2         98            950.04      1.2         96      99    98    980.08      0           64            750         0.04        24             80.08      0.04         81*    73     92*  770.08      0           64            750         0.15        47            750.08      0.15        100*    81    93    940.08      0           64            750         0.3         97            800.08      0.3         99      99    92    950.08      0           64            750         1.2         98            950.08      1.2         100     99    98    990.32      0           83            930         0.04        24             80.32      0.04        100*    87    100*  940.32      0           83            930         0.15        47            750.32      0.15        100*    91    100   980.32      0           83            930         0.3         97            800.32      0.3         99            100   990.32      0           83            930         1.2         98            950.32      1.2         100     100   100   100______________________________________ .sup.1 O is the observed mean broadleaf and mean grass injury data from Table 3A .sup.2 E is the expected results for combinations of clomazone and atrazine based on the response for each herbicide alone derived from Limpel's formula, namely: ##STR2## where X is the observed mean injury when one the the herbicides is used alone. Y is the observed mean injury when the other herbicide is used alone *When the observed results exceed the result which would have been expected, synergism is demonstrated.

Claims (5)

We claim:
1. A method of controlling undesirable vegetation in the locus of a gramineous crop while minimizing injury to the crop, which comprises applying, to seed of the crop or the locus thereof an antodotally effective amount of a safener against injury from the clomazone, and applying to the locus of the crop a herbicidally effective amount of clomazone.
2. The method of claim 1 wherein the crop is corn.
3. The method of claim 1 wherein the safener is 1 8-naphthalic anhydride.
4. The method of claim 1 wherein the safener is 1,8-naphthalic anhydride and the safener is applied to seed of the crop.
5. The method of claim 4 wherein the crop is corn.
US07/074,383 1987-07-16 1987-07-16 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops Abandoned USH806H (en)

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US07/074,383 USH806H (en) 1987-07-16 1987-07-16 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
ZW6788A ZW6788A1 (en) 1987-07-16 1988-05-23 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
IT2088088A IT1217797B (en) 1987-07-16 1988-06-07 The herbicidal compositions based on clomazone and methods of use implicanto a greater tolerance in the case of crops of corn and other crops
FR8808878A FR2618053A1 (en) 1987-07-16 1988-06-30 Process for controlling weeds in a graminaceous plant field and composition for implementing it
ZA885152A ZA8805152B (en) 1987-07-16 1988-07-15 Herbicidal clomazone compositions and methods of use tolerant to corn and other crops
BR8803594A BR8803594A (en) 1987-07-16 1988-07-18 A method for controlling undesirable vegetation and herbicidal composition

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US9247735B2 (en) * 2011-01-19 2016-02-02 Rotam Agrochem International Company Limited Crop plant-compatible herbicidal compositions containing herbicides and safeners

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US4909831A (en) * 1989-02-06 1990-03-20 Fmc Corporation Safening of crops against a triazolinone herbicide with 1,8-naphthalic anhydride
US5527762A (en) * 1990-12-12 1996-06-18 Zeneca Limited Antidoting herbicidal 3-isoxazolidinone compounds
EP0561970B1 (en) * 1990-12-12 1995-01-18 Zeneca Inc. Antidoting herbicidal 3-isoxazolidinone compounds
AT249141T (en) * 1993-02-18 2003-09-15 Basf Ag mixtures herbicides
WO2000003592A2 (en) * 1998-07-16 2000-01-27 Aventis Cropscience Gnbh Herbicidal agents with substituted phenoxysulfonylureas
AU2015218838B2 (en) * 2014-02-23 2018-03-22 Fmc Corporation Use of 3-isoxazolidinones compounds as selective herbicides

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DK251184A (en) * 1983-05-27 1984-11-28 Lilly Co Eli Combination product for use in water as herbicide and algicide
DE3519453A1 (en) * 1985-05-31 1986-12-04 Bayer Ag Herbicidal compositions comprising photosynthesis-inhibitor-type herbicides in combination with vinyl azoles
DE3540919A1 (en) * 1985-11-19 1987-05-21 Bayer Ag Herbicidal composition containing photosynthesis-inhibitor-type herbicides in combination with cyclic urea derivatives

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US9247735B2 (en) * 2011-01-19 2016-02-02 Rotam Agrochem International Company Limited Crop plant-compatible herbicidal compositions containing herbicides and safeners

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