ITTO20070281A1 - HERBICIDE COMPOSITION - Google Patents

Description

DESCRIPTION of the industrial invention entitled: "Herbicidal composition",

DESCRIPTION

Technical field

The present invention relates to a herbicidal composition and a herbicidal process.

Background technique

Numerous herbicides are currently available on the market and are widely used. There is however a wide variety of weeds to control and their growth lasts a long time. For this reason, herbicides with superior herbicidal activity, a broad spectrum of weed control, long-term effects and crop safety are in demand.

Description of the Invention The present invention provides a composition and process for controlling a wide variety of weeds with superior herbicidal effect without phytotoxicity to crops.

The invention precisely provides a herbicidal composition which contains N- (7-fluoro-3, 4-dihydro-3-oxo-4-prop-2-yl-2H-14-benzoxadin-6-yl) cyclohex-1-en -1,2-dicarboxamide (flumioxazine) and a compound represented by the formula (I):

(THE)

(compound [I]) as an active ingredient, wherein the ratio of flumioxazine to compound [I] is 1: 0.01-1: 100.

It also provides a herbicidal process which includes the application of flumioxazine and compound [I] to weeds or soil in a location where weeds grow or can grow, where the weight ratio of flumioxazine to compound [I] is 1: 0.01-1: 100.

Flumioxazine [chemical name: N- {7-fluoro-3,4-dihydro-3-oxo-4-prop-2-yl-2H-1, 4-benzoxadin-6-yl) cyclohex-1-en-1 , 2-dicarboxamide] is a herbicidal compound described in Crop Protection Handbook Vol. 89 (2003), Meister Publishing Company, ISBN: 1-892829-06-1, p. C-236. It can be prepared by a known preparation process, and flumioxazine-containing formulations are available on the market.

Compound [I] can be prepared with a known preparation process described in USP 2005-0032650A.

The herbicidal composition of the present invention comprises flumioxazine and compound [I] as active ingredients and the ratio of flumioxazine to compound [I] in the herbicidal composition is 1: 0.01-1: 100, preferably 1: 0.1-1: 20, more preferably 1: 0.2-1: 10 by weight.

The herbicidal composition exhibits herbicidal activity against a wide variety of weeds, and can therefore be used to effectively control a wide variety of weeds in crop fields, vegetable crops, woodlands or uncultivated land. Furthermore, it does not cause significant phytotoxicity for useful plants.

The present invention also provides a process for controlling weeds which comprises the joint or simultaneous application of flumioxazine and compound [I] to weeds or soil in a location where weeds grow or can grow, where the ratio of flumioxazine to compound [I] is from 1: 0.01 to 1: 100, preferably from 1: 0.1 to 1:20, more preferably from 1: 0.2 to 1:10 by weight.

The process can be used to control weeds, especially in farmland, vegetable crops, woodland or uncultivated land.

Examples of crops of the present invention include crops of edible products such as peanuts, soybeans, corn, wheat and barley; feed crops such as sorghum and oats; industrial crops such as cotton and sugar plantations such as sugar cane. Examples of vegetables affected by the present invention include Solanaceae crops such as aubergines, tomatoes, green pepper, red pepper and potato; Cucurbits such as cucumbers, pumpkins, squashes, watermelons and melons; Brassicaceae such as horseradish, turnip, horseradish, kohlrabi, Chinese cabbage, kale, Indian mustard, broccoli and cauliflower; Composites such as burdock, fior d'oro, artichoke and lettuce; Liliaceae such as porraccina, onion, garlic and asparagus; Umbelliferae such as carrot, parsley, celery and parsnip; Chenopodiacee such as spinach and chard; Lamiaceae such as perilla, mint, basil and lavender; strawberries; sweet potato; yam and taro. Woodland examples include orchards, tea plantations, blackberry crops, coffee plantations, banana plantations, palm plantations, gardens, ornamental trees, nurseries, forests, and gardens. Examples of fruit trees include apple, pear, Japanese pear, Japanese quince, and quince; Stone fruit such as peach, plum, peach, Japanese apricot, cherry, apricot and plum; citrus fruits such as satsuma orange, orange, lemon, lime and pineapple; chestnut, walnut, avellana, almond, pistachio, cashew and macadamia nut trees; berries such as blueberries, cranberry, blackberry and raspberry; grape; persimmon; olive and medlar. Examples of uncultivated land of the present invention include playgrounds, wasteland, railroad embankments, parks, parking lots, roadsides, dry river beds, land below power lines, construction land, and industrial land.

Examples of weeds include:

Polygonaceae such as Polygonurn convolvulus, Polygnum lapathifolium, Polygonurn pensyhnicuin, Polygonum persicaria, Rumex crispus, Rumex obtusifolius and Polygonum cuspidatuxn;

Portulacaceae such as Portulaca oleracea;

Caryophyllaceae such as Stellaria media;

Chenopodiacee such as Chenopodium album and Kochia scoparia;

Amarantaceae such as Amaranthus retroflexus and Amaranthus hybridus;

Crucifers such as Raphanus raphanistrum, Sinapis arvensìs and Capsella bursa pastoris;

Legumes such as Sesbania exaltata, Cassia obtusifolia, Desmodium tortuosum, Trifolium repens, Pueraria lobata and Vicia angustifolia;

Malvaceae such as Abutilon theophrasti and Sida spinosa;

Violaceous such as Viola arvensis and Viola tricolor; Rubiaceae such as Galium aparine;

Convolvolaceae such as Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacea var. integriuscula, I-pomoea lacunose and Convolvulus arvensis;

Labiates such as Lamium purpureum and Lamium amplexicaule;

Solanaceae such as Datura stramonium and Solanum nigrum;

Scrofolariacee such as Veronica persica and Veronica hederaafolia;

Composites such as Xanthium pensylvanicum, Helìanthus annuus, Matricaria inodora, Chrysanthemum segetum, Matricaria matricarioides, Ambrosia artemisiifolla, Ambrosia trifida, Erigeron Canadensis, Artemisia princes and Solidago altissima;

Borraginaceae such as Myosotis arvensis;

Asclepiaclaceae such as Asclepias syriaca;

Euphorbiacee such as Euphorbia helioscopia and Euphorbia maculata;

Geraniacee such as Geranium carolinense and Erodium cicutarium;

Grasses such as Echinochloa crus-galli, Setaria viridis, Setaria faberi, Digitaria sanguinalis, Eleusine indica, Poa annnua, Alopecurus myosuroides, Avena fatue, Sorghum halepense, Agropyron repens, Bromus tectorum, Cynodone dactylon, Panlorum texorghare, Panloricum dichotomif multiflorum;

Commelinaceae such as Commelina communis and Commelina benghalensis;

Equisetaceae such as Eguisetum arvense; And

Cyperaceae such as Cyperus iria, Cyperus rotundus and Cyperus esculentus.

The herbicidal composition can be formulated as emulsifiable concentrates, wettable powders, suspension concentrates, granules and so on by mixing a solid vehicle or a liquid vehicle and optionally surfactants and the other additives of the formulation. These formulations generally contain from about 0.1 to 90% by weight, preferably from 1 to 80% by weight of the total amount of flumioxazine and compound [I].

Examples of solid vehicle used for formulating the composition of the invention include fine powders and granules of clays such as kaolinite, diatomaceous earth, synthetic hydrated silica, Fubasami clay, bentonite and terra alba; talc; other inorganic minerals such as sericite, quartz powder, sulfur powder, activated carbon and calcium carbonate; and chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea. Examples of liquid carriers include water, alcohols such as methanol and ethanol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, ethylbenzene and methylnaphthalene; non-aromatic hydrocarbons such as hexane, cyclohexane and kerosene; esters such as ethyl acetate and buffalo acetate; nitriles such as acetonitrile and isobutyronitrile, ethers such as dioxane and diisopropyl ethers; acid amides such as dimethylformamide and dimethylacetamide; halogenated hydrocarbons such as dichloroethane and trichlorethylene.

Examples of surfactant used for the formulation include esters of alkylsulfates, alkylsulfonate, alkylaryl sulphonate, alkylaryl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol ethers, esters of polyvalent alcohols and derivatives of sugar alcohols. Examples of other formulation aids include adhesive and dispersing agents such as casein, gelatin; polysaccharides (such as starch, gum arabic, cellulose derivatives, alginic acid); lignin derivatives; bentonite; and water-soluble synthetic polymers (such as polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid); and stabilizers such as PAP (isopripyl acid phosphate), BHT (2,6-tert-butyl-4-methylphenol), BHA (2- / 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fat and fatty acid ester.

The herbicidal composition can also be prepared by mixing each formulation after the addition of the active ingredients with the above procedure.

The herbicidal composition obtained can be applied as such for the herbicidal method of the present invention. It can also be diluted with water or the like, and then the dilution applied to the soil or plant. It can be envisaged to increase the herbicidal effect by using the herbicidal composition of the invention in conjunction with another herbicide. Furthermore, the herbicidal composition can be used with insecticides, fungicides, plant growth regulators, fertilizers, protectors, soil improving agents, and so on.

The dose of the herbicide composition or the procedure depends on the mixing ratio of flumioxazine and compound [I] as active ingredients, climatic conditions, types of formulation, time of application, methods of application, places of application, plants and crops to be treated, and it is normally from 1 to 1000 g of total quantity of active ingredient per hectare. When the formulation is an emulsifiable concentrate, wettable powder, suspendable concentrate, the indicated quantity is normally diluted with about 100 to 20001 of water per hectare and applied. Furthermore, when the composition of the invention is applied to plants by foliar treatment, it is envisaged to increase the herbicidal effect against weeds by adding an additive to the dilution of the composition of the invention.

Examples

In what follows the present invention is explained with examples in detail. Examples of wording are given. In the following examples part (parts) means part (parts) by weight.

Formulation example 1

25 parts of flumioxazine, 25 parts of compound [I], 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrated silica are well pulverized and mixed to obtain a wettable powder.

Formulation example 2

70 parts of flumioxazine, 14 parts of compound [I], 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and 11 parts of synthetic hydrated silica are well pulverized and mixed to obtain a wettable powder.

Formulation example 3

14 parts of flumioxazine, 70 parts of compound [I], 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and 11 parts of synthetic hydrated silica are well pulverized and mixed to obtain a wettable powder.

Formulation example 4

10 parts of flumioxazine, 5 parts of compound [I], 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and 80 parts of synthetic hydrated silica are well pulverized and mixed to obtain wettable powder.

Formulation example 5

20 parts of flumioxazine, 20 parts of compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of carboxy methylcellulose (CMC) and 54 parts of water are mixed and wet pulverized to obtain particles with a diameter of 5 μ or less to form a suspendable concentrate.

Formulation example 6

50 parts of flumioxazine, 10 parts of compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of carboxyethylcellulose (CMC) and 34 parts of water are mixed and wet pulverized to obtain particles with a diameter of 5 μ or less to form a concentrate suspendable.

Formulation example 7

5 parts of flumioxazine, 25 parts of compound [I], 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of carboxyethylcellulose (CMC) and 64 parts of water are mixed and wet pulverized to obtain particles with a diameter of 5 μ or less to form a concentrate suspendable.

Formulation example 8

4 parts of flumioxazine, 2 parts of compound [I], 3 parts of polyxyethylene sorbitan monooleate, 3 parts of carboxymethylcellulose (CMC) and 88 parts of water are mixed and wet pulverized to obtain particles with a diameter of 5 μ or less to form a suspendable concentrate.

Formulation example 9

One part of flumioxazine, one part of compound [I], 0.5 parts of Neocol YSK (sodium dialkylsulfosuccinate ester produced by Dai-ichi Kogyo Seiyaku Co., Ltd.), 2 parts of Toxanon GR31A (anionic polycarboxylate surfactant produced by Sanyo Chemical Industries, Ltd.), 30 parts of Kunigel VI (bentonite produced by Kumìnime Industries Co., Ltd.) and 65.5 parts of calcium carbonate are introduced into a small mixer, mixed, kneaded, granulated with an extruder ( RG-5M manufactured by Kikusui Seisakusho, Ltd.) and dried in a fluidized bed dryer (MDB-400 manufactured by Fuji Paudal Co., Ltd.), and then filtered with 16-48 mesh to obtain granules.

Biological tests are now being provided.

Basis of evaluation

Herbicidal activity is evaluated at 11 levels using indices from 0 to 10, represented by 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, where a score of "0" indicates that there is no or small difference in the degree of growth between treated and untreated plants at the time of observation and a score of "10" indicates that the treated plants die or their growth is totally inhibited . Herbicide values of "7", "8", "9" and "10" indicate excellent herbicidal activity, and "6" or less indicates insufficient herbicidal activity. Phytotoxicity against crops is evaluated with the indications "no damage", "modest", "medium" or "severe", in which "no damage" indicates that no damage was found or very little damage, "modest" indicates that the damage is light, "medium" indicates that the damage is medium and "severe" indicates that the damage is severe.

Test example 1

Plastic pots, each with a diameter of 18 cm and a height of 14 cm, were filled with dry soil and then wheat and javone were sown. On the surface of the soil of the aforementioned pots, flumioxazine granules (granules containing 0.25% of fumioxazine, commercial name: Broad Star, produced by Valent U.S.A.), granules containing the compound were manually applied in the quantity indicated in table 1 [I] (prepared using one part of compound [X], 0.5 parts of Neocol YSK, 2 parts of Toxanon GR31A, 30 parts of Kunigel V1 and 66.5 parts of calcium carbonate according to formulation example 9) , and a mixture of flumioxazine granules with the granules containing the compound [I].

The treated plants were kept in the greenhouse. Herbicidal activity and phytotoxicity against the crop were examined 48 days after treatment. The results are shown in Table 1.

As can be seen in test example 1, an excellent herbicidal effect was obtained synergistically in the area treated with the composition of the invention with respect to the area treated with flumioxazine or the compound [I] alone. Furthermore, no damage is found in wheat.

Test example 2

Plastic pots each having a diameter of 9 cm and a height of 7 cm were filled with dry soil, then peanuts were sown. The next day a mixture of flumioxazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, produced by Valent U.S.A.) and emulsifiable concentrate containing the compound [I] (prepared by dissolving compound [I] with acetone containing Tween 20 (surfactant, sorbitanmonolaurate polyglycol ether)) diluted with a suitable quantity of water.

The treated plants were kept in the greenhouse. Herbicidal activity and phytotoxicity against the crop were evaluated 21 days after treatment. The results are shown in Table 2.

As can be seen in Test Example 2, the composition of the invention does not cause damage or causes little damage to the peanuts.

Test example 3

Plastic pots with a width of 32 cm, a depth of 22 cm and a height of 8 were filled with dry soil and a tuber of yellowhammer was sown. The following day, flumioxazine WDG (water dispersible granules containing 51% flumioxazine, commercial name: Valor SX, produced by Valent U.S. A.), emulsifiable concentrate containing the compound [I ] (prepared by dissolving compound [I] with acetone containing Tween 20 (surfactant, polyglycol ether sorbitanmonolaurate)} and the mixture was diluted with the indicated amount of water.

The treated plants were kept in the greenhouse. Herbicidal activity and phytotoxicity against the crop were examined 21 days after treatment. The results are shown in Table 3.

As can be seen in Test Example 3, an excellent synergistic herbicidal effect was obtained in the area treated with the composition of the invention with respect to the area treated with flumioxazine alone or with compound [Ij.

Test example 4

Plastic pots, each having a width of 32 cm, a depth of 22 cm and a height of 8 cm, were filled with dry soil, then tomato seedlings were transplanted and dogwood and common amaranth were sown. The following day a mixture of flumioxazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, produced by Valent U.S.A.) and emulsifiable concentrate containing the compound [I] (prepared by dissolving compound [I] with acetone containing Tween 20 (surfactant, polyglycol ether sorbitanmonolaurate)) diluted with the indicated amount of water.

The treated plants were kept in the greenhouse. Herbicidal activity and phytotoxicity against vegetables were examined 21 days after treatment. The results are shown in Table 4.

As can be seen in Test Example 4, an excellent herbicidal effect was obtained in the area treated with the composition of the invention. Furthermore, no damage was found on the tomatoes.

Test example 5

Plastic pots each having a width of 17 cm, a depth of 12 cm and a height of 7 cm were filled with dry soil, then cucumbers were transplanted and sown giavone, black nightshade and common porcelain. The following day, a mixture of flumioxazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, produced by Valent U.S.A,) and emulsifiable concentrate containing the compound was evenly applied on the ground with a small sprayer. [I] (prepared by dissolving compound [I] with acetone containing Tween 20 (surfactant, sorbitanmonolaurate polyglycol ether)), diluted with an indicated amount of water.

The treated plants were kept in the greenhouse. Herbicidal activity and phytotoxicity against vegetables were examined 21 days after treatment. The results are reported in table 5.

As can be seen in Test Example 5, an excellent herbicidal effect was obtained in the area treated with the composition of the invention. Furthermore, no harm was found for the cucumbers.

Test example 6

Plastic pots each having a diameter of 21 cm and a height of 20 cm were filled with dry soil, then potatoes were planted and sown giavone, sanguinella and veronica. The following day, a mixture of flumioxazine granules (granules containing 0.25% flumioxazine, trade name: Broad Star, produced by Valent U.S.A.), granules containing 0.9% compound [I] (prepared according to the example of formulation 9) and a mixture of flumioxazine granules with the granules containing compound [I].

Herbicidal activity and phytotoxicity against the vegetable were examined 14 days after treatment. The results are shown in table 6.

As can be seen in Test Example 6, an excellent herbicidal effect was obtained synergistically in the area treated with the composition of the invention. Furthermore, no damage was found to the potato.

Test example 7

Plastic containers having a width of about 46 cm, a depth of about 31 cm and a height of about 26 cm are filled with dry soil and vines (variety: Delaware) were planted in them, then giavone, sanguinella and common amaranth. On the surface of the ground of the aforementioned plastic pots, a mixture of flumioxazine granules (granules containing 0.25% flumoxazine, commercial name: Broad Star, produced by Valent U.S.A.) and granules containing flumoxazine was manually applied in the indicated quantity. 0.9% of compound [I] (prepared according to the example of formulation 9).

Herbicidal activity and phytotoxicity against grapevine were examined 14 days after treatment. The results are shown in table 7.

As can be seen in Test Example 7, an excellent herbicidal effect was ensured in the area treated with the composition of the invention. Furthermore, no damage was found to the grapes.

Test example 8

A plastic container having a width of about 46 cm, a depth of about 31 era and a height of about 26 cm was filled with dry soil and a chestnut tree (Gin-yose variety) was planted, then they were sown giavone, sanguinella and common amaranth, on the surface of the soil of the aforementioned plastic pot, a mixture of flumioxazine granules (granules containing 0.25% flumioxazine, commercial name: Broad Star, produced by Valent U.S.A.) and granules containing 0.9% of the compound [I] (prepared according to the example of formulation 9).

Herbicidal activity and phytotoxicity against chestnut were examined 14 days after treatment. The results are shown in table 8.

As can be seen in Test Example 8, an excellent herbicidal effect was obtained in the area treated with the composition of the invention. Furthermore, no damage was observed for the chestnut tree.

The present invention makes it possible to control various weeds with low doses in cultivated land, vegetable land, woodland, uncultivated land and so on.

Claims (9)

CLAIMS 1. Herbicidal composition comprising N— (7— fluoro-3,4-dihydro-3-oxo-4-prop-2-yl-2H-1,4-benzoxadin-6-yl) cyclohex-1-en-1 , 2-dicarboxamide (flumioxazine) and a compound represented by the formula (I): (compound [I]) as an active ingredient, wherein the weight ratio of flumioxazine to compound [I] is 1: 0.01-1: 100. 2. Herbicidal composition according to claim 1, wherein the weight ratio of flumioxazine to compound [I] is 1: 0.1-1: 20. 3. Herbicidal composition according to claim 1, wherein the weight ratio of flumioxazine to compound [I] is 1: 0.2-1: 10. 4. A process for controlling weeds which includes the application of N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-inyl-2H-1,4-benzoxadin-6-yl) cyclohex-l-en-1,2-dicarboxamide and the compound represented by formula (1} together or simultaneously with weeds or soil in a place where weeds grow or can grow, where the ratio of flumioxazine to compound [I ] is 1: 0.01 to 1: 100. 5. Process for controlling weeds according to claim 4, wherein the weight ratio of flumioxazine to compound [I] is 1: 0.1-1: 20. 6. Process for controlling weeds according to claim 4, wherein the weight ratio of flumioxazine to compound [I] is from 1: 0.2 to 1:10. A method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are in cultivated land, in a vegetable crop, in a wood or in uncultivated land. A method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are in cultivated land. A method for controlling weeds according to claim 4, 5 or 6, wherein the weeds are found in wheat fields.