Abstract:
Disclosed herein is herbicidal composition comprising a derivative of 1,2,4-triazole as an active ingredient, represented by the general formula (I): ##STR1## wherein R 1  represents a hydrogen atom, a halogen atom or a C 1  -C 2 ) alkyl group; R 2  represents a hydrogen atom, a halogen atom, a (C 1  -C 2 ) alkyl group fluoromethyl group (--CH 2  F),3,3,3-trifluoropopyl group, methoxy group, cyano group, methoxymethyl group, methylthio group, methoxycarbonyl group or isopropoxycarbonyl group and R 3  represents a thiocarbamoyl group or a group represented by the general formula (II): ##STR2## wherein R 4  represents a hydrogen atom, a (C 1  -C 2 ) alkyl group or a hydroxy (C 1  -C 2 ) alkyl group and R 5  represents a hydrogen atom, a C 1  -C 2 ) alkyl group, halogeno (C 1  -C 2 ) alkyl group, hydroxy (C 1  -C 2 ) alkyl group, cyanomethyl group, acetyl group, halogenoacetyl group, methoxyacetyl group, amino group, phenyl group, methoxy group, hydroxyl group, (C 2  -C 3 ) alkenyl group, halogeno (C 2  -C 3 ) alkenyl group, isopropylcarbonyl group, methylthiocarbamoyl group or 2-methoxyethyl group, the proviso that R 2  is not a hydrogen atom, halogen atom or (C 1  -C 2 ) alkyl group when both of R 4  and R 5  represent hydrogen atoms, and herbicidally acceptable carrier(s) or diluent(s).

Description:
This application is a continuation of application Ser. No. 487,742 filed Apr. 22, 1983, abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates to a herbicidal composition comprising a derivative of 1,2,4-triazole as an active ingredient, represented by the general formula (I): ##STR3## wherein R 1  represents a hydrogen atom, a halogen atom or a (C 1  -C 2 ) alkyl group; R 2  represents a hydrogen atom, a halogen atom, a (C 1  -C 2 ) alkyl group, fluoromethyl group (--CH 2  F), 3,3,3-trifluoropropyl group, methoxy group, cyano group, methoxymethyl group, methylthio group, methoxycarbonyl group or isopropoxycarbonyl group and R 3  represents a thiocarbamoyl group or a group represented by the general formula (II): ##STR4## wherein R 4  represents a hydrogen atom, a (C 1  -C 2 ) alkyl group or a hydroxy (C 1  -C 2 ) alkyl group and R 5  represents a hydrogen atom, a (C 1  -C 2 ) alkyl group, halogeno (C 1  -C 2 ) alkyl group, hydroxy (C 1  -C 2 ) alkyl group, cyanomethyl group, acetyl group, halogenoacetyl group, methoxyacetyl group, amino group, phenyl group, methoxy group, hydroxyl group, (C 2  -C 3 ) alkenyl group, halogeno (C 2  -C 3 ) alkenyl group, isopropylcarbonyl group, methylthiocarbamoyl group or 2-methoxyethyl group, with the proviso that R 2  is not a hydrogen atom, halogen atom or (C 1  -C 2 ) alkyl group when both of R 4  and R 5  represent hydrogen atoms, and herbicidally acceptable carrier(s) or diluent(s). 
     The present inventors have studied for finding a compound showing an excellent activity in selectively controlling weeds such as Echinochloa crus-galli, Poa annua, Chenopodium album, Cardamine flexuosa, Portulaca orelacea, etc. without any phytotoxicity to crop plants such as rice, wheat and maize, and as a result, they have found that a derivative of 1,2,4-triazole, represented by the general formula(I) shows an excellent herbicidal activity for practically controlling the weeds, and have been attained to the present invention. 
     DETAILED DESCRIPTION OF THE INVENTION 
     The compounds according to the present invention represented by the general formula(I) show herbicidal activity to broad-leaved plants and graminaceous plants, and exhibit excellent herbicidal activity, particularly to the broad-leaved weeds such as Portulaca oleracea, Chenopodium album, Stellaria media, Cardamine flexuosa, etc. in various weed-control tests such as seed germination test, soil-treatment test and foliar application test, etc. without causing any phytotoxicity to useful plants such as Oryza sativa, Triticum aestivum, Zea mais, etc. The field of application of the compounds according to the present invention (hereinafter referred to as the present compound) covers the application on arable lands such as paddy fields, ordinary crop fields, orchards, etc. and on growing the flowering plants. 
     The present compounds are synthesizable according to some of the reactions shown by the following reaction formulae (a) to (d). 
     (1) In the case where R 3  represents ##STR5## and R 5  represents a hydrogen atom, a (C 1  -C 2  ) alkyl group, halogeno (C 1  -C 2 ) alkyl group, hydroxy (C 1  -C 2 ) alkyl group, cyanomethyl group, amino group, phenyl group, methoxy group, hydroxyl group, (C 2  -C 3 ) alkenyl group, halogeno (C 2  -C 3 ) alkenyl group, isopropylcarbonyl group or 2-methoxyethyl group, the present compound is conveniently synthesizable by at first reacting a suitable amino derivative (III) to a derivative of 4-phenylhydrazono-2-phenyloxazoline-5-one (IV) in acetone or dioxane and cyclizating the thus obtained compound (V) by the use of hydrochloric acid as are shown in the reaction formula(a). 
     Reaction formula(a): ##STR6## 
     (2) In the case where R 3  represents ##STR7## and R 5  represents acetyl group, halogenoacetyl group, or methoxyacetyl group, the present compound is easily synthesized by acylating a derivative of 1,2,4-triazole(VI) with an acid chloride or an acid anhydride in an inert solvent such as benzene or toluene as is shown in the following reaction formula(b). 
     Reaction formula(b): ##STR8## 
     (3) In the case where R 3  represents a thiocarbamoyl group, the present compound is synthesized by reacting a cyano derivative of 1,2,4-triazole(VII) with hydrogen sulfide in methanol in which ammonia has been absorbed as shown in the following reaction formula(c). 
     Reaction formula(c): ##STR9## 
     (4) In the case where R 3  represents a group ##STR10## and R 5  represents a methythiocarbamoyl group, the present compound is synthesized by reacting a derivative of 1,2,4-triazole(VIII) with N-methylthiourea in a solvent such as benzene and toluene as is shown in the following reaction formula(d). 
     Reaction formula(d): ##STR11## 
     The concrete examples of the present compounds and their physicochemical properties are shown in Table 1. 
     
                                           TABLE 1__________________________________________________________________________                                       MeltingNo. of Substituents in General formula (I)   Point                                            Yieldcompound R.sup.1     R.sup.2  R.sup.3       Appearance (°C.)                                            (%)__________________________________________________________________________1     H   H        CONHCH.sub.3  pale yellow cryst.                                       158-159                                            63.52     H   3-CH.sub.3              CONHCH.sub.3  colorless cryst.                                       135-136                                            61.73     H   3-CH.sub.3              CONHC.sub.6 H.sub.5                            pale yellow cryst.                                       204-206                                            66.74     H   3-CH.sub.3              CONHCH.sub.2 CH.sub.2 Cl                            colorless cryst.                                       126-128                                            64.65     H   3-CH.sub.3              CONHCH.sub.2 CH.sub.2 OH                            colorless cryst.                                       102-104                                            63.26     H   3-CH.sub.3              CONHCH.sub.2 CN                            pale brown vis..sup.1 liq..sup.2                                       --   61.37     H   3-CH.sub.3              CONHOH        pale brown cryst.                                       155-158                                            64.68     H   3-CH.sub.3              CONHNH.sub.2  pale yellow cryst.                                       52-55                                            62.79     H   3-CH.sub.3              CONHOCH.sub.3 colorless cryst.                                       133-135                                            67.210    H   3-CH.sub.3              CON(CH.sub.3).sub.2                            colorless cryst.                                       130-131                                            63.011    H   3-CH.sub.3              CON(CH.sub.2 CH.sub.2 OH).sub.2                            pale brown cryst.                                       114-116                                            70.312    3-CH.sub.3     4-CH.sub.3              CONHCH.sub.3  colorless cryst.                                       150-152                                            69.113    3-CH.sub.3     4-CH.sub.3              CONHCH.sub.2 CH.sub.2 OH                            pale brown cryst.                                       107-109                                            74.014    3-CH.sub.3     4-CH.sub.3              CONHOH        pale brown vis. liq.                                       --   7315    3-CH.sub.3     4-CH.sub.3              CONHOCH.sub.3 pale yellow cryst.                                       147-149                                            58.716    3-CH.sub.3     4-CH.sub.3              CON(CH.sub.3).sub.2                            colorless cryst.                                       175-176                                            66.017    2-CH.sub.3     3-Cl     CONHCH.sub.3  colorless cryst.                                       195-196                                            72.018    2-CH.sub.3     3-Cl     CONHCH.sub.2 CH.sub.2 Cl                            colorless cryst.                                       140-141                                            61.319    2-CH.sub.3     3-Cl     CONHCH.sub.2 CH.sub.2 OH                            pale yellow cryst.                                        98-101                                            63.720    H   H        CONHCOCCl.sub.3                            colorless cryst.                                       162-163                                            63.621    H   H        CONHCOCF.sub.3                            colorless cryst.                                       125-127                                            42.022    H   3-CH.sub.3              CONHCOCH.sub.3                            colorless crtst.                                       142-144                                            59.723    H   3-CH.sub.3              CONHCOCH.sub.2 OCH.sub.3                            colorless cryst.                                       128-130                                            60.024    H   3-CH.sub.3              CONHCOCH.sub.2 Cl                            colorless cryst.                                       126-128                                            61.325    H   3-CH.sub.3              CONHCOCHCl.sub.2                            colorless cryst.                                       168-170                                            73.026    H   3-CH.sub.3              CONHCOCCl.sub.3                            colorless cryst.                                       161-162                                            75.027    2-CH.sub.3     3-Cl     CONHCOCCl.sub.3                            colorless cryst.                                       186-188                                            55.028    H   3-CH.sub.3              CON(CH.sub.3)(COCH.sub.3)                            colorless cryst.                                       127-128                                            65.029    H   3-CH.sub.3               ##STR12##    colorless cryst.                                       149-150                                            67.230    H   3-CH.sub.2 F              CONH.sub.2    colorless cryst.                                       137-138                                            5531    H   3-OCH.sub.3              CONH.sub.2    pale orange cryst.                                       132-134                                            4732    H   3-CH.sub.2 OCH.sub.3              CONH.sub.2    colorless cryst.                                       124-126                                            6333    H   3-SCH.sub.3              CONH.sub.2    pale brown cryst.                                       167-168                                            6434    H   3-CN     CONH.sub.2    pale orange cryst.                                       195-196                                            5635    H   3-COOCH.sub.3              CONH.sub.2    pale brown cryst.                                       169-170                                            7036    H   3-COOCH(CH.sub.3).sub.2              CONH.sub.2    colorless cryst.                                       170-172                                            5937    H   3-CH.sub.2 CH.sub.2 CF.sub.3              CONH.sub.2    pale yellow cryst.                                       176-177                                            6338    5-CH.sub.3     2-OCH.sub.3              CONH.sub.2    colorless cryst.                                       212-213                                            6739    H   3-CH.sub.3              CSNH.sub.2    pale yellow cryst.                                       154-156                                            2240    H   3-CH.sub.2 CH.sub.2 CF.sub.3               ##STR13##    colorless cryst.                                       148-150                                            7541    4-CH.sub.3     3-CH.sub.3               ##STR14##    colorless cryst.                                       154-156                                            5442    3-Cl     2-CH.sub.3               ##STR15##    colorless cryst.                                       160-162                                            6543    H   3-CH.sub.3               ##STR16##    colorless cryst.                                       170-171                                            6644    4-CH.sub.3     3-CH.sub.3               ##STR17##    colorless cryst.                                       129-131                                            4145    H   3-CH.sub.3               ##STR18##    colorless cryst.                                       126-128                                            9046    H   3-CH.sub.3               ##STR19##    colorless cryst.                                       185-187                                            5247    H   3-CH.sub.3               ##STR20##    pale orange cryst.                                       102-104                                            4048    H   3-CH.sub.3               ##STR21##    colorless cryst.                                       139-140                                            5649    H   3-CH.sub.3               ##STR22##    colorless cryst.                                       118-119                                            3250    H   3-CH.sub.3               ##STR23##    colorless cryst.                                       63-65                                            2351    H   3-CH.sub.3               ##STR24##    colorless oil                                       --   46__________________________________________________________________________ 
    
     Of the attached drawings, FIGS. 1 to 51 show the infrared absorption spectrum of Compounds Nos. 1 to 51 according to the present invention, respectively. 
    
    
     The following are the synthetic examples of some of the present compounds, the number of each compound corresponding to that shown in Table 1. 
     SYNTHETIC EXAMPLE 1 
     Synthesis of Compound No. 2 
     In 30 ml of acetone, 2.8 g (0.01 mol) of 4-(3-methylphenylhydrazono)-2-phenyloxazoline-5-one (represented by Formula(IV), wherein R 1  represents a hydrogen atom and R 2  represents a methyl group at 3-position) was suspended, and after adding 1.0 g (0.013 mol) of aqueous 40% solution of methylamine to the suspension, the mixture was heated under a reflux condenser for 30 min. After cooling the reaction mixture, 1.5 ml of conc. hydrochloric acid was added to the reaction mixture drop by drop, and then the mixture was again heated under a reflux condenser for 5 min. After cooling the mixture, the mixture was added into 300 ml of water. The thus separated solid substance was collected by filtration and recrystallized from aqueous ethanolic solution (ethanol:water=10:2 by volume) to obtain 1.8 g of colorless crystals melting at 135° to 136° C. in a yield of 61.7%. 
     SYNTHETIC EXAMPLE 2 
     Synthesis of Compound No. 3 
     In 30 ml of dioxan, 2.8 g (0.01 mol) of 4-(3-methylphenylhydrazono)-2-phenyloxazoline-5-one (represented by Formula (IV), wherein R 1  represents a hydrogen atom and R 2  represents a methyl group at 3-position) was added, and after further adding 1.3 g (0.013 mol) of aniline to the mixture, the whole system was heated under a reflux condenser for 4 hours. After cooling the reaction mixture, 1.5 ml of conc. hydrochloric acid was added drop by drop to the mixture, and after further heating the mixture for 5 min. at 40° C. and cooling the mixture, the mixture was added into 50 ml of water. The thus separated solid substance was collected by filtration and recrystallized from a mixture of 40 ml of ethanol and 20 ml of dioxan to obtain 2.4 g of pale yellow crystals melting at 204° to 206° C. in a yield of 66.7%. 
     SYNTHETIC EXAMPLE 3 
      Synthesis of Compound No. 7 
     In 20 ml of dioxan, 2.8 g (0.01 mol) of 4-(3-methylphenylhydrazono)-2-phenyloxazoline-5-one (represented by formula (IV), wherein R 1  represents a hydrogen atom and R 2  represents a methyl group at 3-position) was added, and after adding 0.9 g (0.013 mol) of hydroxylamine hydrochloride to the mixture at a room temperature, 3 ml of aqueous solution containing 0.5 g (0.013 mol) of sodium hydroxide was added to the mixture drop by drop. Then, the mixture was heated for 30 min. under a reflux condenser. After an additional heating for 5 min. at 40° C., the reaction mixture was cooled and then was added into 200 ml of water. The thus separated solid substance was collected by filtration and washed with a mixture of acetone and water to obtain 1.9 g of pale brown crystals melting at 155° to 158° C. in a yield of 64.6%. 
     SYNTHETIC EXAMPLE 4 
     Synthesis of Compound No. 26 
     In 50 ml of toluene, 2.8 g (0.01 mol) of 1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxamide (represented by Formula(VI), wherein R 5  and R 2  represent a hydrogen atom, respectively and R 1  represents a methyl group at 3-position) was suspended, and after adding 2.2 g (0.012 mol) of trichloroacetyl chloride to the suspension, the mixture was heated for 2 hours under a reflux condenser. After condensing the reaction mixture, the residue was washed with a small amount of ethanol to obtain 2.5 g of colorless crystals melting at 161° to 162° C. in a yield of 75.0%. 
     SYNTHETIC EXAMPLE 5 
     Synthesis of Compound No. 23 
     In the same manner as in Synthetic Example 4 except for adding 1.3 g (0.012 mol) of methoxyacetyl chloride instead of 2.2 g (0.012 mol) of trichloroacetyl chloride, 2.1 g of colorless crystals melting at 128° to 130° C. was obtained in a yield of 60%. 
     SYNTHETIC EXAMPLE 6 
     Synthesis of Compound No. 42 
     In 100 ml of methanol to which gaseous ammonia had been absorbed, 5.2 g (0.02 mol) of 1-(3-methylphenyl)-3-cyano-5-phenyl-1,2,4-triazole (represented by Formula(VII) wherein R 1  is a hydrogen atom and R 2  is a methyl group at 3-position) was dissolved, and a reaction was carried out while blowing gaseous H 2  S into the solution at 40° to 50° C. for 20 min. After condensing the reaction mixture under a reduced pressure, the condensate was washed with a mixture of hexane and acetone and the residue was recrystallized from a mixture of 30 ml of toluene and 10 ml of hexane to obtain 1.3 g of pale yellow crystals melting at 154° to 156° C. in a yield of 22%. 
     SYNTHETIC EXAMPLE 7 
     Synthesis of Compound No. 43 
     In 30 ml of acetic anhydride, 3.6 g (0.01 mol) of 1-3-(3,3,3-trifluoropropyl)phenyl-5-phenyl-1,2,4-triazole-3-carboxamide was heated under a reflux condenser to react for 2 hours. After condensing the reaction mixture under a reduced pressure, the residue was recrystallized from a mixture of 30 ml of toluene and 10 ml of hexane to obtain 3.0 g of colorless crystals melting at 148° to 150° C. in a yield of 75%. 
     SYNTHETIC EXAMPLE 8 
     Synthesis of Compound No. 49 
     In 50 ml of toluene, 3.0 g (0.01 mol) of 1-(3-methylphenyl)-5-phenyl-1,2,4-triazole-3-carboxylic amide chloride was added, and after adding 0.9 g (0.01 mol) of N-methylthiourea to the mixture, the whole system was heated under a reflux condenser to react for 1 hour. After condensing the reaction mixture under a reduced pressure, the condensate was washed with acetone and recrystallized from toluene to obtain 1.8 g of colorless crystals melting at 185° to 187° C. in a yield of 52%. 
     FORMULATION EXAMPLE 1 
     Preparation of a Wettable Powder 
     The following components were mixed and pulverized to be a wettable powder, and it was applied after diluting with water: 
     50 parts by weight of Compound No. 3, 
     5 parts by weight of a ligninsulfonate, 
     3 parts by weight of an alkylsulfonate and 
     42 parts by weight of diatomaceous earth. 
     FORMULATION EXAMPLE 2 
     Preparation of a Wettable Powder 
     The following components were mixed and pulverized to be a wettable powder, and it was applied after diluting with water: 
     50 parts by weight of Compound No. 32, 
     5 parts by weight of a ligninsulfonate, 
     3 parts by weight of an alkylsulfonate and 
     42 parts by weight of diatomaceous earth. 
     FORMULATION EXAMPLE 3 
     Preparation of an Emulsifiable Concentrate 
     The following components were uniformly mixed together to be an emulsifiable concentrate, and it was applied after diluting with water to be an emulsion: 
     25 parts by weight of Compound No. 10, 
     65 parts by weight of xylene and 
     10 parts by weight of polyoxyethylene alkyl aryl ether. 
     FORMULATION EXAMPLE 4 
     Preparation of a Granular Composition 
     The following components were uniformly mixed, and after adding water to the mixture and kneading the whole system, it was processed into granular form by an extruding granulator and dried to be a granular composition: 
     8 parts by weight of Compound No. 12, 
     40 parts by weight of bentonite, 
     45 parts by weight of clay and 
     7 parts by weight of a ligninsulfonate. 
     EXAMPLE 1 
     Herbicidal Test by Application of Candidate Herbicides onto Soil before Germination of Seeds sown therein 
     After packing a planter of the dimensions of 650×210×200 mm with garden soil in a crop field condition, sowing a predetermined amount of the seeds of plants to be tested thereon and covering the seeds with soil, each of the aqueous dilutions containing the respective compounds in an amount corresponding to 50 g/are of the surface of the soil in the planter was uniformly sprayed onto the surface of the soil. Then, the planter was kept in a glass house under the predetermined conditions for 25 days, and then the state of the plants in the planter was observed, and the herbicidal effect was evaluated by the following standards: 
     
         ______________________________________Standards      Result of observation______________________________________0              without any herbicidal effect1              herbicidal effect of 20%2              herbicidal effect of 40%3              herbicidal effect of 60%4              herbicidal effect of 80%5              herbicidal effect of 100%.______________________________________ 
    
     Test results are shown in Table 2. 
     
                       TABLE 2______________________________________Herbicidal Test Results of Example 1                     Crop plantsCompound Weeds (refer to footnote)                     (refer to footnote)No.      1     2     3   4    5   6   1   2   3    4   5______________________________________ 1       1     0     3   5    5   5   0   0   0    4   3 2       2     0     5   5    5   5   0   0   0    2   2 3       1     1     4   4    5   5   0   0   0    2   2 4       1     0     5   5    5   5   0   0   0    0   1 5       0     0     4   5    5   5   0   0   0    0   2 6       2     2     5   5    5   5   0   0   0    3   3 7       1     1     4   3    5   5   0   0   0    2   2 8       0     0     4   4    5   5   0   0   0    3   2 9       1     0     4   3    5   5   0   0   0    0   110       1     0     5   4    5   5   0   0   0    0   111       0     0     4   3    3   3   0   0   0    2   112       3     4     5   5    5   5   0   0   0    2   213       3     0     5   4    5   5   0   0   0    3   214       1     0     5   5    5   5   0   0   0    4   315       3     0     3   4    5   5   0   0   0    2   116       2     0     5   5    4   5   0   0   0    1   317       1     0     5   5    4   5   0   0   0    0   318       0     0     3   4    3   4   0   0   0    0   119       1     0     4   3    5   5   0   0   0    1   220       2     3     5   5    5   5   0   0   0    5   521       2     3     5   5    5   5   0   0   0    4   422       3     4     5   5    5   5   0   0   0    4   523       2     2     5   5    5   5   0   0   0    3   524       2     5     5   5    5   5   0   0   1    2   525       1     5     5   5    5   5   0   0   0    5   526       4     5     5   5    5   5   0   1   0    3   527       1     3     4   5    5   5   0   0   2    1   228       1     1     4   3    5   5   0   0   0    2   229       0     0     4   3    3   3   0   0   0    2   1                                 0   0   0    5   330       3     3     5   5    5   5   0   0   0    5   431       1     1     4   4    5   5   0   0   0    4   432       2     2     4   4    4   5   0   0   0    4   333       1     1     4   4    5   4   0   0   0    4   434       2     2     4   4    5   4   0   0   0    4   435       2     2     4   5    4   5   0   0   0    4   436       1     1     4   4    4   4   0   0   0    4   337       2     3     5   5    4   5   0   0   0    4   4    1     2     4   4    5   5   0   0   0    3   338       1     2     4   4    4   4   0   0   0    3   3    1     1     4   4    4   5   0   0   0    3   339       3     3     5   5    5   5   0   0   0    5   440       1     2     5   5    4   5   0   0   0    4   341       3     3     5   5    5   4   0   0   0    4   442       2     3     5   5    5   4   0   0   0    4   343       1     2     4   5    4   4   0   0   0    4   344       5     5     5   5    5   5   1   2   1    5   545       3     3     5   5    5   5   1   1   1    4   446       2     2     4   4    5   5   0   0   0    4   447       1     1     4   5    4   5   0   0   0    4   348       1     1     4   5    5   4   0   0   0    4   349       1     1     4   5    4   5   0   0   0    4   450       1     1     4   4    5   4   0   0   0    4   451       1     1     4   4    4   4   0   0   0    3   3Control  0     0     0   0    0   0   0   0   0    0   0______________________________________ Note: Name of Weed and Crop Plant Weed 1: Echinochloa crusgalli- Weed 2: Poa annua- Weed 3: Chenopodium album- Weed 4: Cardamine flexuosa- Weed 5: Portulaca oleracea- Weed 6: Stellaria media- Crop plant 1: Rice plant Crop plant 2: Wheat Crop plant 3: Maize  Crop plant 4: Cucumber Crop plant 5: Tomato 
    
     EXAMPLE 2 
     Herbicidal Test by Application of Candidate Herbicide onto Plants at their initial stage of growing 
     Each predetermined amount of the seeds of the plants to be tested was sown onto the soil in the same manner as in Example 1, and when the plants reached to their 1 to 2 leaf-stage, each of the aqueous dilutions containing the respective compounds in an amount corresponding to 50 g/are of the surface of the soil in the planter was uniformly sprayed onto the foliage and the surface of the soil. The planter was kept thereafter in a glass house controlled under predetermined conditions for 25 days and then the state of the plants was observed and the herbicidal effect of each compound was evaluated on the same standard shown in Example 1. The results are shown in Table 3. 
     As are seen in Tables 2 and 3, almost all the present compounds showed excellent herbicidal activity, particularly to the board-leaved weeds as Chenopodium album, Cardamine flexuosa, Portulaca orelacea and Stellaria media when applied to their seeds in the soil or at the initial stage of foliar development thereof, without giving any serious phytotoxicity to crop plants such as rice, wheat and maize. 
     
                       TABLE 3______________________________________Herbicidal Test Results of Example 2: (Foliar Application)Compound Weeds            Crop plantsNo.      1     2     3   4    5   6   1   2   3    4   5______________________________________ 1       2     2     5   5    5   5   0   0   0    4   3 2       4     3     5   5    5   5   0   0   0    1   2 3       2     1     4   5    5   5   0   0   0    2   2 4       2     2     5   5    5   5   0   0   0    0   1 5       0     0     4   5    5   5   0   0   0    0   2 6       1     1     5   5    5   5   0   0   0    3   3 7       0     0     4   5    5   5   0   0   0    2   2 8       0     1     2   5    2   5   0   0   0    0   2 9       2     1     4   3    5   5   0   0   0    1   110       3     2     5   4    5   5   0   0   0    1   111       0     1     2   4    4   5   0   0   0    0   012       3     2     5   5    5   5   0   0   0    0   213       2     1     5   5    5   5   0   0   0    1   314       3     0     4   5    5   5   0   0   0    2   415       3     0     4   3    5   5   0   0   0    1   316       2     1     5   5    5   5   0   0   0    3   317       0     0     5   4    5   5   0   0   0    1   218       0     0     4   3    3   5   0   0   0    0   219       3     0     4   2    3   5   0   0   0    2   420       1     2     5   5    5   5   0   0   1    5   521       2     2     5   5    5   5   0   0   0    4   422       1     1     5   5    5   5   0   0   0    3   523       2     3     5   5    5   5   0   0   0    3   524       3     1     5   5    5   5   0   0   0    2   525       1     2     5   5    5   5   0   0   0    5   526       3     5     5   5    5   5   0   1   3    3   527       2     5     5   5    5   5   0   0   3    4   328       0     1     2   5    2   5   0   0   0    0   229       0     1     2   4    4   5   0   0   0    1   2    1     3     5   5    5   5   0   0   0    4   430       2     2     5   5    5   5   0   0   0    5   531       0     1     5   5    4   4   0   0   0    4   332       1     1     4   4    4   4   0   0   0    4   433       0     0     4   5    4   4   0   0   0    3   334       1     2     4   4    4   5   0   0   0    4   335       0     1     4   4    4   4   0   0   0    4   336       0     0     4   4    4   4   0   0   0    4   337       2     3     5   5    5   4   0   0   0    4   4    0     1     4   4    4   4   0   0   0    3   338       0     0     4   4    4   4   0   0   0    3   3    1     0     4   4    4   4   0   0   0    3   339       2     3     5   5    5   5   0   0   0    5   440       1     2     5   5    5   4   0   0   0    4   341       3     3     5   5    5   5   0   0   0    4   442       2     2     5   5    5   5   0   0   0    4   443       0     1     4   5    4   4   0   0   0    4   344       4     5     5   5    5   5   1   2   1    4   445       3     3     5   5    5   5   1   1   0    4   446       2     2     4   4    4   4   0   0   0    4   447       1     1     4   5    4   4   0   0   0    3   348       0     0     4   5    5   4   0   0   0    3   349       0     0     4   4    4   4   0   0   0    3   350       0     0     4   4    4   4   0   0   0    3   351       0     0     4   4    4   4   0   0   0    3   3Control  0     0     0   0    0   0   0   0   0    0   0______________________________________ Note: Names of weeds and crop plants are the same as in Table 2.