Abstract:
There is disclosed a herbicidal composition comprising as active ingredients a herbicidally effective amount of (a) an iminothiazoline compound of the formula: ##STR1## wherein R 1  is halogen, halo(C 1  -C 2 )alkyl, halo(C 1  -C 2 )alkoxy or halo(C 1  -C 2 )alkylthio; R 2  is C 1  -c 2  alkyl, chroline, bromine or iodine; R 3  is C 1  -C 6  alkyl, C 3  -C 6  cycloalkyl, C 3  -C 6  cycloalkoxy or C 1  -C 6  alkoxy, all of which are optionally substituted with at least one substituent selected from halogen, C 1  -C 2  alkyl and C 1  -C 2  alkoxy; R 4  is hydrogen or halogen; and (b) at least one of herbicidal triazine compounds, herbicidal uracil compounds, herbicidal urea compounds, herbicidal dinitro aniline compounds, norflurazon, dimethazon, imazaquin and imazethapyr. Also disclosed is a method for controlling undesired weeds by use of the herbicidal composition.

Description:
FIELD OF THE INVENTION 
     The present invention relates to a herbicidal composition. More particularly, it relates to a herbicidal composition comprising an iminothiazoline compound and at least one of particular herbicidal compounds. 
     BACKGROUND OF THE INVENTION 
     A great number of chemical substances having a herbicidal activity have been used for herbicidal agents to exterminate or control the vegetation of undesired weeds in agricultural and non-agricultural fields. However, there are many kinds of weeds and their growth extends over a long period of time, so that most of the conventional herbicidal agents have an effect only on the specific kinds of weeds. Accordingly, there is a great demand on herbicidal agents capable of exerting a strong herbicidal activity against a wide variety of weeds without any material phytotoxicity to crop plants. 
     By the way, no-till cultivation has recently been developed for saving labor work, extending a cultivation period and preventing loss in weight of soil. For this reason, there also is a great demand on herbicidal agents capable of exerting a distinct herbicidal activity in foliar treatment, maintaining a prolonged herbicidal efficacy in soil treatment and showing a prominent selectivity between crop plants and weeds. 
     OBJECTS OF THE INVENTION 
     The present inventors have intensively studied herbicidal agents and found that a highly enhanced herbicidal activity against a wide variety of weeds in agricultural and non-agricultural fields can be attained by the combined use of particular herbicidal compounds. 
     SUMMARY OF THE INVENTION 
     The present invention provides a herbicidal composition comprising as active ingredients a herbicidally effective amount of (a) an iminothiazoline compound of the formula: ##STR2## wherein R 1  is halogen, halo(C 1  -C 2 )alkyl, halo(C 1  -C 2 )alkoxy or halo(C 1  -C 2 )alkylthio; R 2  is C 1  -C2 alkyl, chroline, bromine or iodine; R 3  is C 1  -C 6  alkyl, C 3  -C 6  cycloalkyl, C 3  -C 6  cycloalkoxy or C 1  -C 6  alkoxy, all of which are optionally substituted with at least one substituent selected from halogen, C 1  -C 2  alkyl and C 1  -C 2  alkoxy; R 4  is hydrogen or halogen (hereinafter referred to as compound (I)); and (b) at least one of herbicidal triazine compounds, herbicidal uracil compounds, herbicidal urea compounds, herbicidal dinitro aniline compounds, norfrurazon, dimetazon, imazaquin and imazetapia (hereinafter referred to as compound (II)). 
     DETAILED DESCRIPTION OF THE INVENTION 
     The herbicidal composition of the present invention is characterized by the combined use of compounds (I) and (II). In comparison with the separate use of each of these compounds, this combined use provides remarkable enhancement of the herbicidal potency, so that they may be used at a smaller dosage. Further, the weed-control spectrum is widely enlarged. Thus, a clear and definite herbicidal effect is observed in the combined use, and the herbicidal composition can be used with high safety for no-till cultivation of crop plants such as cotton, soybean, corn, wheat, barley and rice plant. 
     The herbicidal composition of the present invention can exterminate or control a variety of weeds, of which examples are broad-leaved weeds such as common puslane (Portulaca oleracea), common chickweed (Stellaria media), common lambsquarters (Chenopodium album), redroot pigweed (Amaranthus retroflexus), radish (Raphanus sativus), wild mustard (Sinapis arvensis), shepherdspurse (Capsella bursa-pastoris), hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), veivetleaf (Abutilon theophrasti), prickly sida (Sida spinosa), field pansy (Viola arvensis), catchweed bedstraw (Galium aparine), ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), field bindweed (Convolvulus arvensis), purple deadnettle (Lamium purpureum), henbit (Lamium amplexicaure), jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), persian speedwell (Veronica persica), common cooklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata) and corn marigold (Chrysanthemum segetum). Examples of Graminaceous weeds include Japanese millet (Echinochloa frumentacea), barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), yellow foxtail (Setaria glauca), southern crabgrass (Digitaria ciliaris), large crabgrass (Digitaria sanguinalis), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), oats (Avena sativa), wild oats (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), giant foxtail (Setaria faberi), fall panicum (Panicum dichotomiflorum), shattercane ( Sorghum bicooor) and bermudagrass (Cynodon dactylon). It should be noted that the herbicidal composition of the present invention have the advantage of exhibiting no material chemical injury to various agricultural crops such as corn, wheat, barley, soybean, cotton and rice plant (particularly, to cotton, soybean, corn, wheat and barley when compound (II) is a triazine compound or urea compound; to cotton or soybean when compound (II) is norfrurazon, dimetazon, imazaquin or imazetapia; and to cotton, rice plants or soybean when compound (II) is a dinitro aniline compound). 
     The compound (I) can be produced according to the process as described in EP-A-0446802. Examples of compound (II) are described by Imamura et al., &#34;Short Review of Herbicides and PGRs 1991&#34;, 188-211, 174, 268, 170, 172, 180-183 and 54-91 (1990), such as atrazine, cyanazine, prometryne, metribuzin, simazine, simetryne, ametryne, metamitron (preferably atrazine, cyanazine, prometryne, metribuzin) as triazine compounds; isoprocil, bromacil, lenacil as an uracil compound; fenuron, monuron, monolinuron, buturon, diuron, linuron, metoxuron, chlorotoluron, isoproturon, fluometuron as urea compounds; trifluralin, benefin, pendimethalin, oryzalin, ethalfluralin, prodiamine as dinitro aniline compounds; norflurazon, dimethazone, imazaquin and imazethapyr. 
     However, the combined use of compounds (I) and (II) has never been attempted. 
     Among various kinds of compound (I), preferred are those wherein R 1  is halo(C 1  -C 2 )alkyl, more preferably trifluoromethyl; those wherein R 2  is C 1  -C 2  alkyl, more preferably methyl; those wherein R 3  is C 1  -C 6  alkoxy, C 1  -C 6   alkyl or halo(C 1  -C 6 )alkyl, more preferably C 1  -C 6  alkyl substituted with fluorine, more preferably methyl substituted with fluorine, more preferably difluoromethyl or trifluoromethyl; and those wherein R 4  is hydrogen or fluorine at the para position, more preferably hydrogen. The proportion of compounds (I) and (II) as the active ingredients in the herbicidal composition of the present invention may vary within a considerable broad range. In general, however, herbicidal triazine compounds as compound (II) can be used in an amount of about 0.1 to 100 parts by weight, preferably of about 0.2 to 50 parts by weight, more preferably of about 0.5 to 30 parts by weight; norflurazon, dimetazon, imazaquin or imazethapyr as compound (II) can be used in an amount of about 0.1 to 100 parts by weight, preferably of about 0.2 to 50 parts by weight, more preferably of about 0.3 to 30 parts by weight; herbicidal uracil compounds as compound (II) can be used in an amount of about 0.5 to 100 parts by weight, preferably of about 0.8 to 30 parts by weight, more preferably of about 1 to 20 parts by weight; herbicidal urea compounds as compound (II) can be used in an amount of about 0.1 to 100 parts by weight, preferably of about 0.5 to 50 parts by weight, more preferably of about 0.8 to 30 parts by weight; herbicidal dinitro aniline compounds as compound (II) can be used in an amount of about 0.5 to 100 parts by weight, preferably of about 0.8 to 50 parts by weight, more preferably of about 1  to 30 parts by weight, all to one part by weight of compound (I). 
     For the practical usage of the herbicidal composition of the present invention, it is usually formulated with conventional solid or liquid carriers or diluents as well as surface active agents, or other auxiliary agents into conventional formulations such as emulsifiable concentrates, wettable powders, suspensions, flowables, granules and water-dispersible granules. 
     These formulations contain the active ingredients at a total content of from about 0.5% to 90% by weight, preferably from about 1% to 80% by weight. 
     Examples of the solid carrier or diluent are fine powders or granules of kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceos earth, calcite, walnut shell powders, urea, ammonium sulfate and synthetic hydrous silica. As the liquid carrier or diluent, there may be exemplified aromatic hydrocarbons (e.g., xylene, methylnaphthalene), alcohols (e.g., isopropanol, ethylene glycol, ethoxyethanol), ketones (e.g., acetone, cyclohexanone, isophorone), vegetable oil, (e.g., soybean oil, cotton seed oil), dimethylsulfoxide, N,N-dimethylformamide, acetonitrile and water. 
     The surface active agent used for emulsification, dispersing or spreading may be of any type, for instance, either anionic or non-ionic. Examples of the surface active agent include alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, phosphates of polyoxyethylenealkylaryl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters and polyoxyethylene sorbitan fatty acid esters. Examples of the auxiliary agent include ligninsulfonates, sodium alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose) and PAP (isopropyl acid phosphate). 
     The herbicidal composition thus formulated in any suitable formulation is useful for pre-emergence or post-emergence control of undesired weeds by soil or foliar treatment. These treatments include application to the soil surface prior to or after planting, incorporation into the soil prior to planting or transplanting, and the like. The foliar treatment may be effected by spraying the herbicidal composition over the top of plants. It may also be applied directly to the weeds if care must be taken to keep the chemical off the crop foliage. 
     The dosage of the active ingredients may vary depending on the active ingredient species, mixing ratio, formulation used, prevailing weather conditions, prevailing season, mode of application, soil involved, crop and weed species, and the like. Usually, however, the total dosage of the active ingredients is (a) from about 100 to 4000 grams, preferably from 150 to 3000 grams, more preferably from 200 to 2000 grams per hectare, when herbicidal triazine compounds, urea compounds and dinitro aniline compounds are used; (b) from 100 to 20,000 grams, preferably from 150-5000 grams, more preferably 200-2000 grams per hectare, when herbicidal uracil compounds are used; and (c) from 50 to 3000 grams, preferably 100 to 2500 grams, more preferably 150 to 2000 grams per hectare, when norfluazon, dimethazone, imazaquin and imazethapyr are used. The herbicidal composition formulated in the form of an emulsifiable concentrate, wettable powder, suspensions, flowable or water-dispersible granules may usually be employed by diluting it with water at a volume of about 100 to 1000 liters per hectare, if necessary, with addition of an auxiliary agent such as a spreading agent. The herbicidal composition formulated in the form of granules may usually be applied as such without dilution. 
     Examples of the spreading agent include, in addition to the surface active agents as noted above, polyoxyethylene resin acid (ester), ligninsulfonate, abietylenic acid salts, dinaphthylmethandisulfonate and paraffin. 
     The herbicidal composition of the present invention is useful as a herbicide to be employed for paddy field, crop field, orchards, pasture land, lawns, forests and non-agricultural fields. Furthermore, it may be applied in combination with insecticides, acaricides, nematocides, fungicides, other herbicides, plant growth regulators, fertilizers, soil improvers and the like. 
     The present invention will be explained in more detail by way of Reference Examples, Formulation Examples and Test Examples, to which however the invention is not limited in any way. 
     Practical embodiments for production of compound (I) are illustrated in the following examples. 
    
    
     REFERENCE PREPARATION EXAMPLE 1 
     To 2-imino-3-[(3-trifluoromethyl)phenyl]-5-methylthiazoline hydrochloride (7.2 g) in ethyl acetate (100 ml), added were triethylamine (7.4 g) and trifluoroacetic acid anhydride (5.2 g) with stirring at room temperature, and stirring was continued for 3 hours. The residue was washed with water (50 ml) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a crystalline residue which was recrystallized from isopropanol to afford 2-[(trifluoroacetyl)imino]-3-[(3-trifluoromethyl)phenyl]-5-methylthiazoline (Compound No. 46) (7.5 g). m.p., 128.1° C. 
     REFERENCE PREPARATION EXAMPLE 2 
     A mixture of 2-imino-3-[(3-trifluoromethyl)phenyl]-5-methylthiazoline hydrochloride (0.42 g), triethylamine (2.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.8 g) and difluoroacetic acid (0.75 g) in chloroform (10 ml) was refluxed for 8 hours. After cooling, the residue was washed with aqueous hydrochloric acid and aqueous potassium carbonate, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 2-[(difluoroacetyl)imino]-3-[(3-trifluoromethyl)phenyl]-5-methylthiazoline (Compound No. 55) (0.3 g). m.p., 117.9° C. 
     REFERENCE PREPARATION EXAMPLE 3 
     A solution of 2-[(ethoxycarbonyl)imino]-3-[(3-trifluoromethyl)phenyl]thiazoline (0.5 g) and N-iodosuccinimide (0.4 g) in chloroform (30 ml) was refluxed for 20 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.1 g of 2-[(ethoxycarbonyl)imino]-3-[(3-trifluoromethyl)phenyl]-5-iodothiazoline (Compound No. 38). 
     In the same manner as above, various kinds of compounds (I) as shown in Table 1 were obtained. 
     
                       TABLE 1______________________________________ ##STR3##Compound                                 m.p.No.      R.sup.1 R.sup.2 R.sup.3    R.sup.4                                    (°C.)______________________________________ 1       CF.sub.3            CH.sub.3                    OC.sub.2 H.sub.5                               H    115.5 2       CF.sub.3            C.sub.2 H.sub.5                    OC.sub.2 H.sub.5                               H    97.1 3       CF.sub.3            CH.sub.3                    OCH.sub.3  H    136.8 4       CF.sub.3            CH.sub.3                    O-i-C.sub.3 H.sub.7                               H    126.0 5       CF.sub.3            C.sub.2 H.sub.5                    O-i-C.sub.3 H.sub.7                               H    91.8 6       CF.sub.3            CH.sub.3                    O-n-C.sub.3 H.sub.7                               H    91.1 7       CF.sub.3            CH.sub.3                     ##STR4##  H    134.0 8       CF.sub.3            CH.sub.3                     ##STR5##  H    155.7 9       CF.sub.3            CH.sub.3                    OCH.sub.2 CH.sub.2 OCH.sub. 3                               H    103.010       CF.sub.3            CH.sub.3                    OCH.sub.2 CH(CH.sub.3).sub.2                               H    101.611       CF.sub.3            CH.sub.3                    OCH(CH.sub.3)C.sub.2 H.sub.5                               H    107.812       CF.sub.3            C.sub.2 H.sub.5                    OCH.sub.3  H    141.413       CF.sub.3            C.sub.2 H.sub.5                    CH.sub.2 CH(CH.sub.3).sub.2                               H    116.314       CF.sub.3            CH.sub.3                     ##STR6##  H    132.615       CF.sub.3            CH.sub.3                    CH.sub.2 C(CH.sub.3).sub.3                               H    123.116       OCF.sub.3            CH.sub.3                    OC.sub.2 H.sub.5                               H    102.117       OCF.sub.3            CH.sub.3                    O-i-C.sub.3 H.sub.7                               H    120.018       CF.sub.3            C.sub.2 H.sub.5                     ##STR7##  H    111.719       CF.sub.3            C.sub.2 H.sub.5                    O-n-C.sub.3 H.sub.7                               H    75.720       CF.sub.3            CH.sub.3                    i-C.sub.3 H.sub.7                               H    139.621       CF.sub.3            CH.sub.3                    n-C.sub.4 H.sub.9                               H    122.622       OCF.sub.3            C.sub.2 H.sub.5                    O-i-C.sub.3 H.sub.7                               H    63.623       CF.sub.3            CH.sub.3                     ##STR8##  H    100.324       CF.sub.3            CH.sub.3                    C(CH.sub.3).sub.3                               H    94.725       CF.sub.3            CH.sub.3                    CH.sub.2 CH(CH.sub.3).sub.2                               H    92.426       CF.sub.3            CH.sub.3                    CH(CH.sub.3)CH.sub.2 CH.sub.3                               H    58.327       CF.sub.3            Br      OC.sub.2 H.sub.5                               H    136.828       CF.sub.3            Cl      OC.sub.2 H.sub.5                               H    138.229       CF.sub.3            Br      O-i-C.sub.3 H.sub.7                               H    106.030       CF.sub.3            Br      OCH.sub.3  H    106.831       CF.sub.3            Br      n-C.sub.3 H.sub.7                               H    141.432       CF.sub.3            Br      O-n-C.sub.4 H.sub.9                               H    104.933       F       Br      OC.sub.2 H.sub.5                               H    172.434       Br      Br      OC.sub.2 H.sub.5                               H    155.435       Cl      Br      OC.sub.2 H.sub.5                               H    147.736       CF.sub.3            Br      OC.sub.6 H.sub.5                               H    137.737       CF.sub.3            Br      O-n-C.sub.3 H.sub.7                               H    107.038       CF.sub.3            I       OC.sub.2 H.sub.5                               H    121.639       CF.sub.3            CH.sub.3                    CH.sub.2 CH.sub.2 Cl                               H    155.240       CF.sub.3            CH.sub.3                    C.sub.2 H.sub.5                               H    164.641       CF.sub.3            CH.sub.3                    C.sub.3 H.sub.7                               H    111.042       CF.sub.3            C.sub.2 H.sub.5                    CH.sub.3   H    87.843       CF.sub.3            C.sub.2 H.sub.5                    C.sub.2 H.sub.5                               H    117.544       CF.sub.3            C.sub. 2 H.sub.5                    n-C.sub.3 H.sub.7                               H    119.045       CF.sub.3            C.sub.2 H.sub.5                    i-C.sub.3 H.sub.7                               H    96.646       CF.sub.3            CH.sub.3                    CF.sub.3   H    128.147       CF.sub.3            C.sub.2 H.sub.5                    CF.sub.3   H    92.048       CF.sub.3            Br      CF.sub.3   H    113.249       CF.sub.3            CH.sub.3                    C.sub.2 F.sub.5                               H    98.550       CF.sub.3            C.sub.2 H.sub.5                    C.sub.2 F.sub.5                               H    94.151       CF.sub.3            CH.sub.3                    C.sub.3 F.sub.7                               H    61.752       OCF.sub.3            CH.sub.3                    CH.sub.3   H    150.853       OCF.sub.3            CH.sub.3                    CF.sub.3   H    104.754       CF.sub.3            C.sub.2 H.sub.5                     ##STR9##  H    98.355       CF.sub.3            CH.sub.3                    CHF.sub.2  H    117.956       CF.sub.3            CH.sub.3                    CH.sub.2 F H    135.757       CF.sub.3            C.sub.2 H.sub.5                    CHF.sub.2  H    96.358       CF.sub.3            CH.sub.3                    CH.sub.3   4-F  179.059       CF.sub.3            CH.sub.3                    CF.sub.3   4-F  119.460       CF.sub.3            CH.sub.3                    i-C.sub.3 H.sub.7                               4-F  133.261       CF.sub.3            CH.sub.3                    O-i-C.sub.3 H.sub.7                               4-F  130.862       CF.sub.3            CH.sub.3                    CF.sub. 3  6-F  144.763       CF.sub.3            CH.sub.3                    O-i-C.sub.3 H.sub.7                               6-F  158.564       CF.sub.3            CH.sub.3                    CH.sub.3   4-Cl 187.965       CF.sub.3            CH.sub.3                    CF.sub.3   4-Cl 134.266       CF.sub.3            CH.sub.3                     ##STR10## 4-Cl 166.267       CF.sub.3            CH.sub.3                    CHF.sub.2  4-F  139.968       CF.sub.3            C.sub.2 H.sub.5                    CH.sub.3   4-F  131.469       CF.sub.3            C.sub.2 H.sub.5                    CF.sub.3   4-F  84.670       CF.sub.3            C.sub.2 H.sub.5                    CHF.sub.2  4-F  117.0______________________________________ 
    
     Practical embodiments for preparation of the composition are illustrated in the following Formulation Examples wherein parts are by weight. 
     FORMULATION EXAMPLE 1 
     Eight parts of compound (I), 40 parts of prometryn, atrazine, dimetazon, imazetapia, diuron, fenuron, linuron, chlorotoluron, trifluralin, benefin or prodiamine, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 47 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 2 
     Twelve parts of compound (I), 12 parts of metribuzin or bromacil, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 70 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to obtain a suspension. 
     FORMULATION EXAMPLE 3 
     Three tenths parts of compound (I), 9 parts of cyanazine, norflurazon, isoproturon, trifluralin or pendimethalin, 2 parts of calcium ligninsulfonate, 1 part of synthetic hydrated silica and 30 parts of bentonite and 57.7 parts of kaolin clay are well mixed while being powdered. The mixture is then kneaded with water, granulated and dried to obtain granules. 
     FORMULATION EXAMPLE 4 
     Thirty four parts of compound (I), 17 parts of metribuzin, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 44 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 5 
     One and a half parts of compound (I), 45 parts of prometryn or bromacil, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 48.5 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 6 
     Twenty parts of compound (I), 6 parts of imazaquin, 3 parts of polyoxyethlene sorbitan monooleate, 3 parts of CMC and 68 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to obtain a suspension. 
     FORMULATION EXAMPLE 7 
     Fourty parts of compound (I), 8 parts of imazatapyr, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 47 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 8 
     Six parts of compound (I), 30 parts of norflurazon, 2 parts of calcium ligninsulfonate, 1 part of synthetic hydrated silica and 30 parts of bentonite and 31 parts of kaolin clay are well mixed while being powdered. The mixture is then kneaded with water, granulated and dried to obtain granules. 
     FORMULATION EXAMPLE 9 
     One part of compound (I), 50 parts of norfrurazon, fluometuron or trifluralin, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 44 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 10 
     Seven parts of compound (I), 42 parts of bromacil, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 46 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 11 
     A half part of compound (I), 10 parts of bromacil, 2 parts of calcium ligninsulfonate, 1 part of synthetic hydrated silica and 30 parts of bentonite and 56.5 parts of kaolin clay are mixed well while being powdered. The mixture is then kneaded with water, granulated and dried to obtain granules. 
     FORMULATION EXAMPLE 12 
     Twenty five parts of compound (I), 20 parts of lenacil, trifluralin, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurysulfate and 50 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 13 
     One part of compound (I), 30 parts of isoprocil, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 64 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 14 
     Fifteen parts of compound (I), 12 parts of fluometuron, 3 parts of polyoxyetylene sorbitan monooleate, 3 parts of CMC and 67 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to obtain a suspension. 
     FORMULATION EXAMPLE 15 
     Thirty parts of compound (I), 15 parts of diuron, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 50 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     FORMULATION EXAMPLE 16 
     Eight parts of compound (I), 20 parts of trifluralin, oryzalin or ethalfluralin, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 66 parts of water are mixed and pulverized until the particle size becomes less than 5 microns to obtain a suspension. 
     FORMULATION EXAMPLE 17 
     Fourteen parts of compound (I), 14 parts of trifluralin, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 47 parts of synthetic hydrated silica are well mixed while being powdered to obtain a wettable powder. 
     The practical herbicidal activity of the composition of the invention will be explained in further detail with reference to the following Test Examples wherein the growth controlling percentage (%) was determined by weighing the aerial parts of the test plants (fresh weight) and making calculation according to the following equation: ##EQU1## 
     TEST EXAMPLE 1 
     Vats (33 cm×23 cm×11 cm) were filled with upland field soil, and the seeds of the test plants (except for cotton) were sowed therein in 1 to 2 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with a water, and the dilution was sprayed onto the soil surface by means of an automatic sprayer at a spray volume of 1000  liters per hectare. Thereafter, the soil surface (to 4 cm depth) was well mixed and the seeds of cotton were sowed in 2 cm depth. The test plants were grown in a green house for 28 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 2. 
     
                                           TABLE 2__________________________________________________________________________Activeingre-dient           Phyto-               Herbicidal activityTest  dosage       Mixing           toxicity               Bermuda-                     Fall Goose-                              Hemp Commoncompound (g/ha)       ratio           Cotton               grass panicum                          grass                              sesbania                                   cocklebur__________________________________________________________________________Promet-  500  --  none                75    25   0   85   5ryn   1000  --  none                97    80   50  90   94 2000  --  none               100    95   80  95   98Compound 100 + 500       1:5 none               100   100  100 100   71No. 4 + 100 + 1000        1:10           none               100   100  100 100  100Promet- 200 + 500         1:2.5           none               100   100  100 100   98ryn   200 + 1000       1:5 none               100   100  100 100  100Compound 100 + 1000        1:10           none               100   100  100 100  100No. 55 + 200 + 1000       1:5 none               100   100  100 100  100Promet-ryn__________________________________________________________________________ 
    
     TEST EXAMPLE 2 
     Concrete containers (40 cm×35 cm) were filled with upland field soil, and the seeds of the test plants were sowed therein in 1 to 3 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 430 liters per hectare. The test plants treated with the test compositions as described above were grown outdoors for 52 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 3. 
     
                                           TABLE 3__________________________________________________________________________Activeingre-dient           Phyto-                Herbicidal activityTest  dosage       Mixing           toxicity                Southern                     Giant                         Slender                              Jimson-compound (g/ha)       ratio           Soybean                crabgrass                     foxtail                         amaranth                              weed__________________________________________________________________________Metri- 200   --  none  10   10 65   30buzin 400   --  none  50   25 95   30Compound 200 + 200       1:1 none 100  100 95   85No. 4 + 200 + 400       1:2 none 100  100 100  100Metri-buzin__________________________________________________________________________ 
    
     TEST EXAMPLE 3 
     The test plants in Table 4, which had been treated with the test compositions in Table 4 in the same manner as in Test Example 2, were grown outdoors for 29 days, and herbicidal activity and phytotoxicity were examined. The results are shown in Table 4. 
     
                                           TABLE 4__________________________________________________________________________Activeingre-            Herbicidal activityTest dient    Phyto-                      Blackcom- dosage     Mixing         toxicity             Johnson-                  Giant                      Morning-                           Velvet-                                Slender                                     night-pound(g/ha)     ratio         Corn             grass                  foxtail                      glories                           leaf amaranth                                     shade__________________________________________________________________________Cyana- 600 --  none              0    0   0    0    0    85zine 1200 --  none             65    80  98   75   0   100Com- 40 + 600     1:15         none             70   100 100  100  100  100pound80 + 600     1:7.5         none             93   100 100  100  100  100No. 46 +Cyana-zine__________________________________________________________________________ 
    
     TEST EXAMPLE 4 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 m 2 ) each. Seeds of the test plants in Table 5 were sowed therein in 4 to 5 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 236 liters per hectare. Thereafter, the test plants were grown outdoors for 51 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 5. 
     
                                           TABLE 5__________________________________________________________________________  Active  ingre-  dient       Phyto-                   Herbicidal activityTest   dosage Mixing              toxicity                   Johnson-                        Giant                             Slendercompound  (g/ha) ratio              Corn grass                        foxtail                             amaranth__________________________________________________________________________Cyana-  500   --   none 20   13   13zine   1000   --   none 60   27   15  2000   --   none 67   73   40Compound  200 + 500         1:2.5              none 100  100  100No. 4 +  200 + 1000         1:5  none 100  100  100Cyana-zine__________________________________________________________________________ 
    
     TEST EXAMPLE 5 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 m 2 ) each. Seeds of the test plants in Table 6 were sowed therein in 1 to 7 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil sur±ace by means of a small hand sprayer at a spray volume of 236 liters per hectare. Thereafter, the test plants were grown outdoors for 44 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 6. 
     
                                           TABLE 6__________________________________________________________________________  Active  ingre-  dient      Phyto-                  Herbicidal activityTest   dosage        Mixing             toxicity                  Velvet-                        Slender                             Palecompound  (g/ha)        ratio             Soybean                  leaf  amaranth                             smartweed__________________________________________________________________________Metri- 250   --   none  87    7    77buzin  500   --   none 100   30    92Compound  100 + 250        1:2.5             none 100   95   100No. 4 +  200 + 250        1:1.25             none 100   95   100Metri-buzin__________________________________________________________________________ 
    
     TEST EXAMPLE 6 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 m 2 ) each. Seeds of the test plants in Table 6 (except for cotton) were sowed therein in 1 to 7 cm depth. A designated amount of the test composition formulated in a wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 236 liters per hectare. Thereafter, the soil surface (to 7-8 cm depth) was well mixed and the seeds of cotton were sowed therein in 5 to 7 cm depth, the test plants were grown outdoors for 27 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 7. 
     
                                           TABLE 7__________________________________________________________________________  Active  ingre-  dient     Phyto-                Herbicidal activityTest   dosage        Mixing            toxicity                Goose-                    Southern                         Prickly                             Commoncompound  (g/ha)        ratio            Cotton                grass                    crabgrass                         side                             purslane__________________________________________________________________________Promet-   500  --  none                0    0   20   0ryn    1000  --  none                0    13  20   30Compound  100 + 500        1:5 none                83  100  100 100No. 46 +Promet-ryn__________________________________________________________________________ 
    
     TEST EXAMPLE 7 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 m 2 ) each. Seeds of the test plants in Table 8 (except for cotton) were sowed therein in 1 to 7 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water containing a spreading agent, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 236 liters per hectare. Thereafter, the soil surface (to 7-8 cm depth) was well mixed and the seeds of cotton were sowed therein in 5 to 7 cm depth, the test plants were grown outdoors for 27 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 8. 
     
                                           TABLE 8__________________________________________________________________________Activeingre-dient           Phyto-                Herbicidal activityTest  dosage       Mixing           toxicity                Slender                     Prickly                         Common                              Sickle-compound (g/ha)       ratio           Cotton                amaranth                     side                         purslane                              pod__________________________________________________________________________Norflu-  750  --  none  17   58  33   13razon 1500  --  none  23   92  90   67Compound 200 + 750        1:3.75           none 100  100 100  100No. 4 +Norfru-razonCompound 100 + 750       1:7.5           none 100  100 100  100No. 46 +Norfru-razonCompound 100 + 750       1:7.5           none 100  100 100  100No. 55 +Norfru-razon__________________________________________________________________________ 
    
     TEST EXAMPLE 8 
     The test plants in Table 9 were treated with the test compositions in Table 9 and grown in the same manner as in Test Example 2. The herbicidal activity and phytotoxicity were examined. The results are shown in Table 9. 
     
                                           TABLE 9__________________________________________________________________________  Active  ingre-  dient     Phyto-                 Herbicidal activityTest   dosage        Mixing            toxicity                 Quack-                     Johnson-                          Southern                               Slendercompound  (g/ha)        ratio            Soybean                 grass                     grass                          crabgrass                               amaranth__________________________________________________________________________Dimethazone  400   --  none 10  60   50   40  800   --  none 80  90   50   75Compound  200 + 400        1:2 none 100 100  100  100No. 4 +Dimetazone__________________________________________________________________________ 
    
     TEST EXAMPLE 9 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 cm 2 ) each. Seeds of the test plants in Table 10 were sowed therein in 4 to 8 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 236 liters per hectare. Thereafter, the test plants were grown outdoors for 44 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 10. 
     
                                           TABLE 10__________________________________________________________________________Activeingre-dient           Phyto-               Herbicidal activityTest  dosage       Mixing           toxicity                Giant                    Southern                         Morning-                              Jimson-compound (g/ha)       ratio           Soybean                foxtail                    crabgrass                         glories                              weed__________________________________________________________________________Imazaquin  70   --  none 50   7   50   40 140   --  none 68   43  67   67 280   --  none 85   52  82   82Compound 100 + 70       1:0.7           none 100 100  100  100No. 4 + 100 + 140       1:1.4           none 100 100  100  100Imazaquin__________________________________________________________________________ 
    
     TEST EXAMPLE 10 
     Sandy plowed fields were turned up and, after border builiding, plotted into blocks of 3 m 2  (1×3 m 2 ) each. Seeds of the test plants in Table 11 were sowed therein and cultivated outdoors for 41 days. A designated amount of the test composition formulated in a wettable powder as in Formulation Example 1 was diluted with water containing a spreading agent, and the dilution was sprayed over the foliage of the test plants by means of a small hand sprayer at a spray volume of 236 liters per hectare. At the time of the treatment, the test plants had 9-24 cm in height and 3.5-8 leaves. Thereafter, the test plants were grown outdoors for 43 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 11. 
     
                                           TABLE 11__________________________________________________________________________Activeingre-          Herbicidal activity dient     Persian  Lambs-  CommonTest  dosage       Mixing           speed-               Common                    quar-                        Curly                            chick-                                 Slender                                      Asiaticcompound (g/ha)       ratio           well               purslane                    ters                        dock                            weed amaranth                                      dayflower__________________________________________________________________________Bromacil 1200  --   53  88   70  75 10   43    80 2400  --   88 100   90  98 10   53   100Compound 100 + 1200       1:12           100 100  100 100 70   97   100No. 46 + 200 + 1200       1:6 100 100  100 100 100  100  100Bromacil__________________________________________________________________________ 
    
     TEST EXAMPLE 11 
     Concrete containers (40 cm×35 cm) were filled with upland field soil, and the seeds of the test plants in Table 12 were sowed therein in 1 to 3 cm depth. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 658 liters per hectare. The test plants treated with the test compositions as described above were grown outdoors for 30 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 12. 
     
                                           TABLE 12__________________________________________________________________________ Active ingre- dient     Phyto-               Herbicidal activityTest  dosage       Mixing           toxicity               Prickly                   Velvet-                        Goose-                            Southern                                 Bermuda-compound (g/ha)       ratio           Cotton               side                   leaf grass                            crabgrass                                 grass__________________________________________________________________________Fluome-  500  --  none               0   0    0   60   35turon 1000  --  none               30  0    55  70   50Compound  50 + 500        1:10           none               70  100  100 100  100No. 46 + 100 + 500       1:5 none               100 100  100 100  100Fluome-turonCompound 100 + 500       1:5 none               100 100  100 100  100No. 55 +Fluome-turon__________________________________________________________________________ 
    
     TEST EXAMPLE 12 
     Concrete containers (40 cm×35 cm) were filled with upland field soil, and the seeds of the test plants in Table 13 were sowed therein, and cultivated outdoors for 29 days. A designated amount of the test composition formulated in an wettable powder as in Formulation Example 1 was diluted with water containing a spreading agent, and the dilution was sprayed over the foliage of the test plants by means of a small hand sprayer at a spray volume of 658 liters per hectare. At the time of the treatment, the test plants had 1-3 cm in height and 1-2 leaves. Thereafter, the test plants were grown outdoors for 39 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 13. 
     
                                           TABLE 13__________________________________________________________________________ Active ingre-   Herbicidal activity dient        Common   Purple                           Catch-                                PersianTest  dosage      Mixing          Ladys-              chick-                   Field                       dead-                           weed speed-compound (g/ha)      ratio          thumb              weed pansy                       nettle                           bedstraw                                well__________________________________________________________________________Isopro-  500 --   60  50  10   0   0    0turon 1000 --  100 100  25  15   0    0Compound 63 + 500      1:8 100 100  90  80  80   100No. 4 +Isopro-turonCompound 63 + 500      1:8 100 100  100 100 90   100No. 46 +Isopro-turon__________________________________________________________________________ 
    
     TEST EXAMPLE 13 
     The test plants in Table 14 were treated with the test compositions in Table 14 and grown in the same manner as in Test Example 10. The herbicidal activity and phytotoxicity were examined. The results are shown in Table 14. 
     
                                           TABLE 14__________________________________________________________________________ Active ingre-    Herbicidal activity dient     Persian               Lambs-       CommonTest  dosage       Mixing           speed-               quar-                   Slender                        Ladys-                            chick-compound (g/ha)       ratio           well               ters                   amaranth                        thumb                            weed__________________________________________________________________________Diuron 1200  --   23  85  83   40  10 2400  --   48  87  97   78  93Compound 100 + 1200       1:12           100 100 100  100 100No.46 + 200 + 1200       1:6 100 100 100  100 100Diuron__________________________________________________________________________ 
    
     TEST EXAMPLE 14 
     The test plants in Table 14, which had been treated with the test compositions in Table 15 in the same manner as in Test Example 5, were grown outdoors for 27 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 15. 
     
                                           TABLE 15__________________________________________________________________________ Active ingre-        Herbicidal activity dient     Phyto-               Barn-Test  dosage       Mixing           toxicity               yard-                   Johnson-                        Morning-                             Slender                                  Sickle-compound (g/ha)       ratio           Cotton               grass                   grass                        glories                             amaranth                                  pod__________________________________________________________________________Fluome-  750  --  none                70  67   65   85  53turon 1500  --  none                80  80   97   92  68Compound 200 + 750       1:3.75           none               100 100  100  100  85No. 4 +Fluome-turonCompound  50 + 750       1:15           none               100 100  100  100  90No. 46 + 100 + 750       1:7.5           none               100 100  100  100  95Fluome-turon__________________________________________________________________________ 
    
     TEST EXAMPLE 15 
     The test plants in Table 16, which had been treated with the test composition in Table 16 in the same manner as in Test Example 5, were grown outdoors for 35 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 16. 
     
                                           TABLE 16__________________________________________________________________________ Active ingre-    Herbicidal activity dient         Catch-                    Persian CommonTest  dosage       Mixing           Downy               weed speed-                        Field                            chick-compound (g/ha)       ratio           brome               bedstraw                    well                        pansy                            weed__________________________________________________________________________Isopro- 1000  --  55  0    27  0   47turon 2000  --  62  0    50  0   87Compound 125 + 1000       1:8 90  100  100 100 97No. 4 +Isopro-turon__________________________________________________________________________ 
    
     TEST EXAMPLE 16 
     The test plants in Table 17 were treated with the test compositions in Table 17 and grown in the same manner as in Test Example 6. The herbicidal activity and phytotoxicity were examined. The results are shown in Table 17. 
     
                                           TABLE 17__________________________________________________________________________ Active ingre- dient     Phyto-               Herbicidal activityTest  dosage       Mixing           toxicity               Goose-                   Southern                        Slender                             Prickly                                 Commoncompound (g/ha)       ratio           Cotton               grass                   crabgrass                        amaranth                             side                                 purslane__________________________________________________________________________Triflu- 375   --  none                17  73   0    17  48ralin 750   --  none                50  95   27   25  75Compound 100 + 375       1:3.75           none               100 100  100  100 100No. 46 +Triflu-ralinCompound 100 + 375       1:3.75           none               100 100  100  100 100No. 55 +triflu-ralin__________________________________________________________________________ 
    
     The biological data of Compound (I) as a herbicide will be illustrated in the following Reference Test Example wherein the phytotoxicity to crop plants and the herbicidal activity on weeds were determined by visual observation as to the degree of germination as well as the growth inhibition and rated with an index 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the numeral &#34;0&#34; indicating no material difference as seen in comparison with the untreated plants and the numeral &#34;10&#34; indicating the complete inhibition or death of the test plants. The compound number in the biological data corresponds to that shown in Table 18. 
     REFERENCE TEST EXAMPLE 1 
     Cylindrical plastic pots (diameter, 10 cm; height, 10 cm) were filled with upland field soil, and the seeds of japanese millet, tall morningglory and velvetleaf were sowed therein and covered with soil. A designated amount of the test compound formulated in an emulsifiable concentrate, which was obtained by well mixing of 5 parts of compound (I), 15 parts of &#34;Toxanone P8L&#34; (a commercial surface active agent; Sanyo Kasei K.K.) and 80 parts of cyclomexanon, was diluted with water, and the dilution was sprayed onto the soil surface by means of a small hand sprayer at a spray volume of 1000 liters per hectare. The test plants were grown in a greenhouse for 20 days, and the herbicidal activity was examined. The results are shown in Table 18. 
     
                       TABLE 18______________________________________        Herbicidal activity                        TallCompound Dosage    Japanese  morning-                                Velvet-No.      (g/ha)    millet    glory   leaf______________________________________1        2000      9         9       10    500       9         7       92        2000      9         10      10    500       7         7       73        2000      10        9       10    500       9         7       84        2000      10        10      10    500       10        10      10    125       10        10      85        2000      10        10      10    500       9         10      8    125       8         9       --6        2000      10        10      10    500       10        10      --7        2000      9         10      10    500       9         8       --8        2000      8         9       --    500       7         8       --9        2000      10        10      10    500       10        10      --10       2000      10        10      9    500       10        9       --11       2000      10        10      1012       2000      10        9       1013       2000      10        10      9    500       10        10      914       2000      10        10      10    500       10        10      --15       2000      10        10      10    500       9         9       --16       2000      10        9       7    500       10        8       --17       2000      10        10      10    500       10        10      1018       2000      10        10      --    500       10        10      --19       2000      10        10      --    500       10        7       --20       2000      10        10      10    500       10        9       1021       2000      10        9       --    500       10        9       --22       2000      10        10      10    500       10        9       9    125       9         9       823       2000      10        10      10    500       10        10      10    125       9         9       824       2000      10        10      --    500       9         9       --25       2000      10        10      8    500       10        10      726       2000      10        10      8    500       10        9       727       2000      9         10      10    500       9         --      1028       2000      9         7       8    500       9         --      729       2000      9         10      9    500       9         10      730       2000      10        10      10    500       9         8       1031       2000      10        10      --32       2000      9         10      7    500       7         8       --36       2000      --        10      1037       2000      10        10      10    500       10        10      10    125       7         8       738       2000      9         10      10    500       8         9       1039       2000      10        10      9    500       10        7       740       2000      10        10      10    500       10        8       741       2000      10        10      10    500       10        10      --42       2000      10        10      10    500       10        10      943       2000      10        10      10    500       10        10      944       2000      10        10      10    500       10        10      945       500       10        10      946       500       10        10      10    125       10        10      1047       500       10        10      10    125       10        10      1048       500       9         9       9    125       8         8       849       500       9         10      950       500       10        10      8    125       9         7       751       2000      7         9       952       500       10        10      1053       500       10        10      10    125       9         10      754       2000      10        10      955       500       10        10      10    125       10        10      1056       500       10        10      10    125       9         9       757       500       10        10      10    125       9         10      1058       2000      10        10      7    500       10        10      759       2000      10        10      10    500       10        10      1060       2000      10        10      10    500       10        10      1061       2000      10        10      10    500       10        10      1062       2000      7         7       764       2000      9         10      765       500       9         10      1066       500       7         8       767       500       10        10      10    125       9         10      968       500       9         9       869       500       9         9       870       500       9         9       10    125       8         8       8______________________________________