A METHOD FOR THE CONTROL OF GALIUM APARINE

Abstract: Disclosed herein is a method of controlling undesirable vegetation which comprises the application to the locus desired of a herbicidal composition comprising a herbicide selected from the group consisting of S-benzyl dipropyl­ thiocarbamate, S-benzyl 2,5-dimethylpiperidine-1-­ carbothioate, S-benzyl methyl isopropyl thiocarbamate, S-­ benzyl propyl allyl thiocarbamate, S-benzyl ethyl cyclohexyl thiocarbamate, s-benzyl ethyl-sec-butyl thiocarbamate, S-(4-­ chlorobenzyl) dipropyl thiocarbamate, and S-benzyl iso­ propylsec-butyl thiocarbamate.

Description: HERBICIDAL COMPOSITIONS AND METHOD OF CONTROLLING WEEDS Cross Reference to Related Applications This application is a continuaton-in-part application of application Serial No. 557,993, filed December 5, 1983. Background of the Invention The protection of crops fran weeds and other vegetation which inhibit crop growth is a constantly recurring Elroblem in agriculture. To help combat this problem researchers in the field of synthetic chem- istry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature ard a large num ber are in commercial use. One such class of compounds is the thiolcarbamates. Thiolcarba- mates in general are disclosed as herbicides in U.S. Patent Nos. 3,185,720 (Tilles et al., May 25, 1965), 3,198,786, (Tilles et al., August 3, 1965) and 2,913,327 (Tilles et al, November 17, 1959). The present invention resides in the discovery that certain S-benzyl thiolcarbamates have exceptional herbicidal activity for use in connection with weed pests which grow among oilseed rape, sugarbeets, barley and wheat crops. Prior Art The preferred S-benzyl thiolcarbanates are disclosed as suitable for use as herbicides in U.S. Patent Nos. 3,144,475 (Harman, et al., August 11, 1964), 2,992,091, (Harman et al., July 11, 1961) and 3,207,775, (September 21, 1965). Description of the Invention It has now been discovered that control of undesirable vegetation among oil seed rape, sugarbeet, barley and wheat crop plants is exhibited by compositions comprising an S4enzyl thiolcarbamate of the formula EMI2.1 in which X is hydrogen or chlorine; and R1 and R2 are independently selected fran the group consisting of C1-C6 alkyl, alienyl, alkyl substituted C5-C7 cyclo alkyl, C5-C7 cycloalkyl, and S-C1-C6 alkyl. The terms "alkyl" and "alkenyl" are used herein to denote both straight-chain and branched chain groups. Examples of alkyl groups in- clude methyl, ethyl, n-propyl, isopmpyl, n-butyl, sec-butyl, isobutyl, etc. Examples of alkenyl groups include vinyl, allyl, 2-butenyl, iso- butenyl, etc. All carbon atan ranges are inclusive of their upper and lower limits. Examples of thiolcarbamates useful in the present invention are: S4enzyl dipropyl thiocarabmate, S-benzyl 2,5-dimethyl piperidine-1 carbothioate, S-benzyl methyl isopropyl thiolcarbamate, Senzyl propyl allyl thiolcarbamate, S-benzyl ethyl cyclohexyl thiolcarbamate, S-benzyl ethyl sec butyl thiolcarbamate, S-(4-chlorobenzyl) dipropyl thiolcarba- mate, and S-benzyl isopropyl-sec-butyl thiolcarbamate. These and other thiolcarbamates within the scope of this invention can be prepared by the procedures described in the patents mentioned above as in U.S. Patent Nos. 2,913,327, 3,185,720, and 3,198,786. Preferred thiolcarbamates are those in which X is hydrogen, and R1 and R2 are independently selected fran the group consisting of C1-C4 alkyl and cyclohexyl. Particularly preferred thiolcarinates are those in which X is hydrogen and R1 is propyl and R2 is propyl. While the above mentioned thiolcarbamate compounds have some herbicidal activity against a wide variety of weed species, they are particularly efficient and effective against those weed species appearing in and around oilseed rape, sugarbeets, barley and wheat. Accordingly, therefore, the method of this invention is a method of controlling undesirable weed pests in the presence of oilseed rape, sugarbeet, barley and wheat crop plants which comprises applying to the locus desired a herbicide composition comprising an S-benzyl thiolcarbamate of the formula EMI3.1 in which X is hydrogen or chlorine; and R1 and R2 are independently selected from the group consisting of C1-c6 alkyl, alkenyl, alkyl substituted C5-C7 cyclo alkyl, C5-C7 cycloalkyl, and S{51 C6 alkyl. The herbicide can be applied in either pre-emergent or postemergent techniques. By pre-emergent it is meant prior to the eruption of plant or weed species from the soil, and by post-emergent it is meant subsequent to the eruption of plant or weed species from the soil. The term "herbicide" is used herein to denote a compound which controls or modifies the growth of plants. The term "herbicidally effec- tive amount" is used to indicate the quantity of such a compound or caribi- nation of such oompounds which is capable of producing a controlling or modifying effect. Controlling or modifying effects include all deviations from natural development, for example: killing, retardation, leaf burn, dwarfing and the like. The term "plants" is used to include all postemergent vegetation, ranging from seedlings to established vegetation. Application rates will depend upon the weeds to be controlled and the degree of control desired. In general, the compositions of this invention are most efficiently employed at a rate of 0.01 to 50 pounds per acre (0.0011 to 56 kilograms per hectare) of the active ingredients, preferably 0.1 to 25 pounds per acre (0.11 to 28 kilograms per hectare). The following examples provide further illustrations demonstrating the herbicidal response of the present compositions. a sand soil is amended with 75 ppn Captan and 50 ppm 17-17-17 fertilizer. One thousand eighty or 1960 cu an aluminum pans (flats) are filled with soil to a depth of about 5 an. Seeds, or some- times botanical parts capable of vegetatively reproducing, are placed in furrows, and covered with soil. The soil is leveled and tamped firm. Monocots and dicots are usually seeded in separate flats. Particular species may vary somewhat from test to test. Weed species are those common to Europe, and ones which occur frequently in wheat, barley, sugarbeet and oilseed rape fields. Abbreviations used for plant species are given below. Common Name Botanical Name Abbreviation winter barley Hordeum vulgare L. BARL bedstraw Galium aparine L. BDSW blackgrass Alopecurus myosuroides Huds. BKGR wild buceat Polygonum convolvulus L. annual bluegrass Poa annua L. cocoon chickweed Stellaria media (L.) Cyrillo canTon lambsquarter Cherpodium album L. CIAM wild mustard Sinapis arvensis L. wild oats Avena fatua L. WOAT oilseed rape Brassica napus L. RAPE perennial ryegrass Lolium perenne L. purslane Portulaca oleracea L. PURS ivyleaf speedwell Veronica hederaefolia L. ILSW sugarbeet Beta vulgaris SUGA winter wheat Triticum aestivum L. L. WHEA Flats to be treated with a preemergence spray are seeded the day prior to, or on the day of, treatment. Flats to be treated with a postemergence spray are placed in a greenhouse after seeding, and watered from overhead. These flats are maintained until the first true leaf tissue of the seedlings appears. Spray treatments are then made at this time. A 1:1 ratio of acetone:water is added to technical grade ccm- pounds to form a spray solution. A 60 ml solution is commonly used. Only water is used to dilute formulated products. Polyoxyethylene sorbitan nnnolaurate (Tween 20e) is routinely added to the acetone at a concentra- tion of 1%. Spray solutions are delivered to the soil surface or foliage by use of a linear spray table operated at 30 psi pressure. Flats are ine diately placed in a greenhouse after spraying. Preemergence flats are watered frcm overhead. Foliage of postemergence flats is not dosed with water so as to maintain placement of the chemical. Greenhouse air temperatures may range from 15eC to 24 C. Whitewash is maintained on the glazing year around. The whitewash reduces the light intensity from the sun by about one-half. A cool and shady environment is maintained in the greenhouse in order to simulate climatic conditions of Western Europe. No supplemental lighting is employed. Two to three weeks after treatment, each row of seedlings or plants is visually rated for growth injury or control due to all factors. Untreated flats of seedlings are used for comparison and their growth is considered zero percent injury. One hundred percent injury or growth control is equivalent to complete kill. The compounds appearing in the following tables are identified as follows: Compound 1 - S-benzyl dipropylthiocarbanate Compound 2 - S-benzyl 2,5-dimethylpiperidine-1-carbothioate Compound 3 - S-benzyl methyl isopropyl thiocarbamate Compound 4 - S-benzyl propyl allyl thiocarbamate Compound 5 - S-benzyl ethyl cyclohexyl thiocarbamate CompOund 6 - S-benzyl ethyl-sec-butyl thiocarbamate CompOund 7 - S-(4-chlorobenzyl) dipropyl thiocarbamate Compound 8 - S-benzyl isopropyl-sec-butyl thiocarbamte TABLE I PREEMERGENCE HERBICIDE TEST RESULTS Application Rate: 4 pounds per acre Percent Growth Control Test Grasses Broadleaves Crops Compound BKGR ABLG PRGR WOAT AVE. BDSW CLAM WBUC CCHW WMUS AVE. SUGA BARL WHEA 1 90 75 95 87 100 100 100 100 60 10 20 2 90 0 90 60 95 95 0 63 20 10 0 3 85 90 80 85 100 95 70 88 60 0 0 4 90 0 95 62 100 100 100 100 80 0 75 5 100 100 90 95 96 0 20 10 0 10 95 6 100 100 100 95 99 10 0 5 0 20 20 6 95 95 95 95 95 0 90 100 100 97 0 0 10 7 95 95 90 95 94 100 100 100 0 10 20 8 100 95 95 95 96 0 0 0 0 0 95 TABLE II POSTMERGENCE HERBICIDE TEST RESULTS Application Rate: 4 pounds per acre Percent Growth Control Test Grasses Broadleaves Crops Compound BKGR ABLG PRGR WOAT AVE. BDSW CLAM WBUC CCHW WMUS AVE. SUGA BARL WHEA 1 80 85 90 85 100 100 100 100 100 85 70 2 10 0 20 10 20 95 20 45 20 20 10 3 0 0 0 0 0 40 0 13 0 20 10 4 10 40 40 30 40 90 70 67 30 30 0 5 100 40 40 80 65 100 100 100 100 100 0 0 6 50 40 40 30 40 100 100 100 100 100 0 0 6 60 30 30 25 36 25 100 100 100 81 100 0 0 7 90 40 30 40 50 100 100 85 95 100 0 0 8 95 30 30 40 49 0 0 0 0 0 0 0 Blanks indicate species not tested. TABLE III PREEMERGENCE HERBICIDE TEST RESULTS Test Application Percent Growth Control Compound Rate (1b/A) BKGR ABLG PRGR WOAT AVE WMUS CCHW ILSW BDSW CLAM AVE SUGA BARL WHEA RAPE 1 1/4 40 0 0 80 30 80 90 95 10 0 0 0 1/2 60 10 55 85 53 90 100 95 20 0 0 0 1 90 35 85 90 75 90 100 95 100 0 0 45 2 100 90 95 95 95 100 100 100 100 0 0 85 1 1/4 0 0 0 80 20 0 30 15 0 0 0 0 1/20 0 0 85 24 0 35 18 0 0 0 0 1 10 50 95 90 80 20 100 60 20 0 0 15 2 85 80 95 90 89 40 100 70 35 0 0 25 2 1/2 10 20 75 35 0 0 0 0 0 0 1 50 60 90 68 0 0 0 0 0 0 2 90 95 100 95 0 0 0 0 0 0 3 1/2 0 0 0 0 0 0 0 0 0 0 1 20 60 75 52 0 0 0 80 0 0 2 40 85 85 70 0 0 0 85 0 0 4 1 40 55 95 63 10 0 0 2 75 90 95 86 20 0 20 4 95 95 95 95 10 0 25 5 1 0 0 90 30 0 0 20 2 20 20 95 45 0 0 0 6 1/4 25 0 0 70 24 0 100 0 33 0 0 0 1/2 65 0 90 95 63 0 100 20 40 0 0 0 1 100 100 100 100 100 0 100 25 42 0 100 100 <RTI ID=8.1> TABLE III (continued) Test Application Percent Growth Control Compound Rate (1b/A) BKGR ABLG PRGR WOAT AVE WMUS CCHW ILSW BDSW CLAM AVE SUGA BARL WHEA RAPE 6 1/4 75 95 95 90 85 90 88 35 0 0 1/2 80 100 100 100 95 50 100 75 40 20 25 1 85 100 100 100 96 70 100 85 45 25 30 2 100 100 100 100 100 100 100 100 100 30 35 7 1/2 10 0 25 40 19 0 0 0 0 0 0 1 65 0 85 85 59 0 0 0 0 0 0 2 95 0 95 95 71 100 90 0 63 0 0 8 1/2 25 30 80 95 54 0 100 50 0 0 0 1 2 80 0 95 95 67 0 100 50 0 0 0 TABLE IV POSTMERGENCE HERBICIDE TEST RESULTS Test Application Percent Growth control Compound Rate (1b/A) BKRG ABLG PRGR WOAT AVE WMUS WBUC CCHW ILSW BDSW PURS CLAM AVE SUGA BARL WHEA 2 1/2 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 3 1/2 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 4 1 20 25 30 25 0 0 0 0 0 0 2 55 40 50 48 100 0 0 0 0 0 4 65 50 60 58 100 0 50 0 0 0 5 1 0 0 45 15 100 0 50 0 0 0 2 0 0 65 22 100 98 99 0 0 0 6 1/4 60 25 15 0 25 0 0 0 0 0 0 0 0 1/2 75 60 25 35 49 0 0 15 0 4 0 0 0 1 90 95 30 40 64 0 0 9 0 23 0 0 0 2 20 25 15 25 21 0 0 100 0 25 0 0 0 6 1/4 90 80 80 80 83 15 0 0 5 0 0 0 1/2 95 95 85 90 91 95 0 0 32 25 0 0 1 95 95 85 95 93 90 15 0 35 35 0 0 2 100 100 100 95 99 100 20 0 40 40 0 0 7 1/2 0 0 0 20 5 75 0 20 32 0 0 0 1 70 45 75 90 70 95 0 50 48 0 0 0 2 85 65 95 95 85 80 0 65 48 0 0 0 8 1/2 0 0 15 20 9 0 0 0 0 0 0 0 1 2 0 0 45 55 25 0 0 0 0 0 0 0 x3LE V PREEMERGENCE ONLY Test Application Percent Growth Control Compound Rate (1b/A) F* TP G I TR WOAT BKGR ABLG PRGR AVE. BDSW 4 1/2 0 0 0 0 0 80 30 0 40 38 0 1 0 0 0 0 0 90 90 0 65 61 0 2 0 0 0 0 0 95 100 0 80 69 85 * F = "Flanders" winter wheat TP = "Top" winter wheat G = "Gerbel" winter barley I = "IGRI" winter barley TR = "Triumph" spring barley The compositions of the present invention show activity as herbicides in controlling the growth of undesirable vegetation when applied to such vegetation in pre- and post-emergence application. The compositions are generally embodied in formulations which contain inert or occasionally active ingredients or diluent carriers in addition to the active compounds. Examples of such ingredients or carriers are water, organic solvents, surface active agents, oil, water-in-oil emulsions, wetting agents, dispersing agents, and emulsifying agents. The herbicidal formulations generally take the form of wettable powders, solutions or emuls ifiable concentrates. Wettable powders are finely divided compositions comprising a particulate carrier impregnated with the herbicidal compound and additionally containing one or more surface active agents. The surface active agent promotes rapid dispersion of the powder in aqueous medium to form stable, sprayable suspensions. A wide variety of surface active agents can be used, for example, long chain fatty alcohols and alkali metal salts of the sulfated fatty alcohols; salts of sulfonic acid; esters of long chain fatty acids; and polyhyric alcohols, in which the alcohol groups are free, anega-substituted polyethylene glycols of relatively long chain length. The herbicidal compositions can also be applied to the foliage in the fonn of a solution in a suitable solvent. Solvents frequently used in herbicidal forrmilations include kerosene, fuel oil, xylene, petroleum fractions with boiling ranges above xylene, and aranatic petroleun fractions rich in methylated napothalenes. The most preferred formulations are emulsifiable concentrates which consist of an oil solution of the herbicide alone with an emulsifying agent. Prior to use, the concentrate is diluted with water to form a suspended emulsion of oil droplets. The emulsifiers used are usually a mixture of anionic and nonionic surfactants. Other additives such as spreading agents and stickers can be included in the emulsifiable concentrate. The formulations described above can be applied to the soil prior to emergence of vegetation, or to vegetation sought to be controlled in any conventional manner after the vegetation has emerged from the soil. The vegetation can be in any stage of development after emergence, ranging from seedlings to fully grown plants. Application can be achieved by any conventional technique such as the use of ground spraying equipment or aircraft-mounted sprayers. Various other application techniques will be apparent to one skilled in the pesticide art. Other herbicide compounds can be used to form mixtures in conjunction with the S-benzyl thiocarbamates of this invention. These include certain S-halobenzyl thiocarbamates such as are described in U.S. Patent 3,846,115, and U.S. Patent 3,582,314. Additionally, compounds such as methyl-2-[((4,6dimethoxypyrimidine-2-yl)aminocarbonyl)aminosulfinyl methyl]benavate such as is manufactured by the DuPont Coopt, Wilmington, Delaware under the designation DPX-F5384 can be used, as wel1 as 2,4Hi- chlorophenoxy acetic acid, commonly known as 2,4-D, and 2-methyl-4-chlorophenoxy acetic acid, commonly known as MCPA and sold by the tradename Weedone MCPA ester by the Union Carbide Company, Boundbrook, New Jersey.

Claims: WHAT IS CLAIMED IS: 1. A herbicidal composition comprising a herbicide selected from the group consisting of S-benzyl dipropylthiocarbamate, S-benzyl 2,5 dimethylpiperidine-l -carbothioate, S-benzyl methyl isopropyl thiocarba- mate, S-benzyl propyl allyl thiocarbamate, S-benzyl ethyl cyclohexyl thio carbonate, S-benzyl ethyl-sesbutyl thiocarbamate, S-(4-chlorobenzyl) dipropyl thiocarbamate, and S-benzyl isopropyl-sec-butyl thiocarbamate. 2. The position of Claim 1 wherein the herbicide is s-benzyl dipropylthiocarbamate. 3. A method of controlling undesirable vegetation which com- prises the application to the locus desired of a herbicidal composition comprising a herbicide selected from the group consisting of S4enzyl dipropylthiocarbamate, S-benzyl 2,5dimethylpiperidine-1-cabothioate, S-benzyl methyl isopropyl thiocarbanate, S-benzyl propyl allyl thiocarbamate, S-benzyl ethyl cyclohexyl thiocarbanate, S-benzyl ethyl-secbutyl thiocartbamate, S-(4chlorobenzyl) dipropyl thiocarmate, and S-benzyl isopropylsec-butyl thiocarbamate. 4. The method of Claim 3 wherein the herbicide is S-benzyl dipropylthiocarbamate. 5. A herbicidal composition wising a mixture of a herbicide selected fran the group consisting of S-benzyl dipropylthiocarbamate, S-benzyl 2, 5-dimethylpiperidine-1 -carfthioate, S -benzyl methyl isopropyl thiocarbamate, S4enzyl propyl allyl thiocarbamate, S-benzyl ethyl cycle hexyl thiocarbamate, S-benzyl ethyl-secbutyl thiocarbamate, S-(4-chlorobenzyl) dipropyl thiocarbamate, and S-bezyl isopropyl-secbutyl thiocarbamate and an inert diluent carrier. 6. A herbicidal composition comprising a mixture of a herbicide selected from the group consisting of S-benzyl dipropylthiocarbamate, S-benzyl 2,5-dimethylpiperidine-1-cabothioate, S-benzyl methyl isopropyl thiocarbamate, S-benzyl propyl allyl thiocarbanate, S-benzyl ethyl cyclohexyl thiocarbamate, S-benzyl ethyl-secbutyl thiocarbamate, S-(4-chloro benzyl) dipropyl thiocarbamate, and S-benzyl isopropyl-sec-butyl thiocar bamate and an inert diluent carrier, together with at least one other herbicide selected fran the group consisting of S-halobenzyl thiocarbamate, methyl-2-[((4,6-dimethoxypyridine-2-yl)aminocarbonyl)aminosul finyl-methyl] benzoate, 2,4-dichlorophenow acetic acid and 2-methyl-4chlorophenoxy acetic acid.

Inventors: MOJICA, ELLEN YURCAK
Applicants: STAUFFER CHEMICAL COMPANY
Application year: 1984
Main classification: A01N47
IPC codes: A01N47