PATENT ABSTRACT
A Δ 2  -1,2,4-triazolin-5-one derivative represented by the following general formula (I), a process for manufacturing thereof, a herbicidal composition comprising it as an active ingredient, and a use of it as a herbicide: ##STR1## wherein R is a hydrogen atom, a univalent alkali metal atom, an unsubstituted quaternary ammonium salt, a substituted quaternary ammonium salt having at least one C 1  -C 4  alkyl group as a substituent, an unsubstituted-alkyl group having 1 to 6 carbon atoms, a C 1  -C 6  substituted-alkyl group having at least one halogen atom as a substituent, a cycloalkyl group having 3 to 6 carbon atoms, a C 1  -C 3  substituted-alkyl group having a cyano group as a substituent, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having to 2 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkylthioalkyl group having to 2 to 8 carbon atoms, an alkylsulfinylalkyl group having 2 to 6 carbon atoms, an alkylsulfonylalkyl group having 2 to 6 carbon atoms, an alkoxyalkoxyalkyl group having 3 to 8 carbon atoms, a hydroxycarbonylalkyl group having 2 to 3 carbon atoms, an alkoxycarbonylalkyl group having 3 to 6 carbon atoms, an unsubstituted-benzyl group, a substituted-benzyl group having at least one substituent selected from the group consisting of halogen atoms and alkyl groups having 1 to 3 carbon atoms, or a phenethyl group; R 1  is a haloalkyl group having 2 to 5 carbon atoms; and X is a halogen atom.

PATENT DESCRIPTION
This is a division of application Ser. No. 845,867, filed Mar, 29, 1986. 
    
    
     BACKGROUND OF THE INVENTION 
     Field of the Invention 
     This invention relates to Δ 2  -1,2,4-triazolin-5-one derivatives represented by the general formula (I): ##STR2## (wherein R is a hydrogen atom, a univalent alkali metal atom, an unsubstituted quaternary ammonium salt, a substituted quaternary ammonium salt having at least one C 1  -C 4  alkyl group as a substituent, an unsubstituted-alkyl group having 1 to 6 carbon atoms, a C 1  -C 6  substituted-alkyl group having at least one halogen atom as a substituent, a cycloalkyl group having 3 to 6 carbon atoms, a C 1  -C 3  substituted-alkyl group having a cyano group as a substituent, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an alkylthioalkyl group having 2 to 8 carbon atoms, an alkylsulfinylalkyl group having 2 to 6 carbon atoms, an alkylsulfonylalkyl group having 2 to 6 carbon atoms, an alkoxyalkoxyalkyl group having 3 to 8 carbon atoms, a hydroxycarbonylalkyl group having 2 to 3 carbon atoms, an alkoxycarbonylalkyl group having 3 to 6 carbon atoms, an unsubstituted-benzyl group, a substituted-benzyl group having at least one substituent selected from the group consisting of halogen atoms and alkyl groups having 1 to 3 carbon atoms, or a phenethyl group; R 1  is a haloalkyl group having 2 to 5 carbon atoms; and X is a halogen atom), a process for production thereof, and uses thereof. 
     DESCRIPTION OF THE PRIOR ART 
     The present inventors have found that compound represented by the above general formula (I) are useful as agricultural chemicals, in particular, herbicides. 
     Compounds similar to the compounds of this invention are disclosed in Japanese Patent Kokai (Laid-open) No. Sho 57-181069 (1982), U.S. Pat. No. 4,318,731, U.S. Pat. No. 4,398,943, U.S. Pat. No. 4,404,019, WO85/01637 and WO85/04307. For example, U.S. Pat. No. 4,318,731 discloses a compound represented by the formula, ##STR3## wherein, R 1  is a C 1  -C 4  alkyl; R 2  is a hydrogen atom, a C 1  -C 4  alkyl group, or a C 2  -C 4  alkenyl group; and X is a hydroxy group, a C 1  -C 4  alkyl group, a C 1  -C 6  alkyloxy group, an alkyloxyalkyloxy group of which two alkyls may be same as or different from each other and each alkyl is of C 1  -C 4 , a C 2  -C 4  alkenyloxy, or an alkyloxycarbonyl-alkyloxy group of which two alkyls may be same as or different from each other and each alkyl is of C 1  -C 4  ; U.S. Pat. No. 4,398,943 discloses a compound represented by the formula, ##STR4## wherein R 1  is an alkyl group; R 2  is an alkynyl group, a halomethyl group, or a haloethyl group; and X is an alkoxy group, an alkenyloxy group, an alkoxy-alkoxy group, an alkynyloxy group, a hydroxy group, a halomethyloxy group, or a haloethyloxy group; and U.S. Pat. No. 4,404,019 discloses a compound represented by the formula, ##STR5## wherein R is a C 1  -C 4  alkyl group, a C 3  -C 4  alkenyl group or a C 3  -C 4  cycloakyl group, X is a chlorine atom or a bromine atom and Y is a hydrogen atom or a C 1  -C 4  alkoxy group, which is useful as a herbicide. 
     Those compounds, however, can not be considered as suitable herbicides from the viewpoints of the dosage and their effects. Furthermore, WO 85/01637 discloses a compound represented by the following formula, ##STR6## in which X 1  and X 2  are independently selected from halogen, haloalkyl, and alkyl; 
     W is oxygen or sulfur; 
     R is a three- to eight-membered ring heterocyclic group of one or two, same or different, ring heteroatoms selected from oxygen, sulfur, and nitrogen or an alkyl radical substituted with said heterocyclic group, said heterocyclic group being unsubstituted or substituted with one or more substituents selected from halogen, alkyl, and haloalkyl, or said heterocyclic group being adjoined to a benzene ring at two adjacent ring carbon atoms to form a benzo-heterocycle bicyclic group, said sulfur heteroatom being present in divalent form, S-oxide form, or S-dioxide form; 
     R 1  is alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, or a group of the formula -alkyl-Y-R 3  ; 
     R 2  is halogen, alkyl, cyanoalkyl, haloalkyl, arylalkyl, or a group of the formula -alkyl-Y-R 3  ; 
     R 3  is alkyl, alkenyl, or alkynyl; and 
     Y is oxygen or S(O) r  in which r is 0 to 2; however, the compound disclosed needs a relatively high dosage for the control of the undersirable weeds and does not have sufficient selectivites between the useful crops and the undersible weeds. WO85/04307 discloses also a similar compound represented by the following formula, ##STR7## in which R is a radical selected from 2-propynyl, 1-methylethyl-2-propynyl, methoxymethyl, 2-propenyl, and 1-methyl-2-methoxyethyl. The compound disclosed, however, kills useful crops in addition to weeds if it is used at a relatively high dosage. On the other hand, sufficient controlling effects of weeds can not be expected if it is used at a relatively lower dosage at which it still gives certain but evident damages on the crops. That is, the compound fails to show sufficient selectivities between the useful crops and weeds. Therefore, there is still a strong demand for a herbicide capable of controlling weeds without causing substantial damages on crops at a lower dosage. While, the present inventors have found that the compounds of this invention disclosed in neither those prior arts nor in any literatures can meet such demand. 
     Additionally, the present inventors have found that surprisingly, the compounds of this invention exhibit excellent herbicidal activities in a lower dosage and have lower phytotoxicities as compared with the compounds disclosed in the above-mentioned prior art references, whereby this invention has been accomplished. 
     An object of the present invention is to provide a compound having excellent herbicidal activities and only low phytotoxicities. 
     A further object of the present invention is to provide a herbicidal composition comprising an effective amount of a compound having excellent herbicidal activities and high crop safety represented by said general formula (I), and suitable inert carrier. 
     A further object of the present invention is to provide a herbicidal composition comprising said compound which is very useful not only as a pre-emergence treatment type herbicide, but also as a post-emergence treatment type herbicide for upland crops. A further object of the present invention is to provide a method of treating said compound as herbicide for upland crops. 
     Further objects of the invention will become apparent from the description of the invention which follows. 
     Preferable examples of the substituent R of the compounds represented by the general formula (I) include, for example, hydrogen atom; univalent alkali metal atoms such as Na, K and the like; quaternary ammonium salts of ammonium, mono-, di-, tri- or tetramethylammonium, mono-, di-, tri- or tetraethylammonium, mono-, di-, tri- or tetrapropylammonium, mono-, di-, tri- or tetrabutylammonium, and the like; alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, and the like; substituted-alkyl groups having halogen atoms as the substituents such as chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl, chlorobutyl, bromobutyl, chloropentyl, bromopentyl, chlorohexyl, bromohexyl, and di-, tri- or polyhaloalkyl thereof and the like; cycloalkyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, and the like; substituted alkyl groups having a cyano group as the substituent such as cyanomethyl, cyanoethyl, cyanopropyl, and the like; alkenyl groups such as ethenyl, 2-propenyl, 1-methylpropenyl, 1,1-dimethylpropenyl, 2-butenyl, pentenyl, hexenyl, and the like; alkynyl groups such as ethynyl, 2-propynyl, 1-methylpropynyl, 1,1-dimethylpropynyl, 2-butynyl, pentynyl, hexynyl, and the like; alkoxyalkyl groups such as methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl, methoxybutyl, ethoxybutyl, methoxypentyl, and the like; alkylthioalkyl groups such as methylthiomethyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl, pentylthiomethyl, hexylthiomethyl, heptylthiomethyl, methylthioethyl, ethylthioethyl, propylthioethyl, butylthioethyl, pentylthioethyl, hexylthioethyl, methylthiopropyl, ethylthiopropyl, propylthiopropyl, butylthiopropyl, pentylthiopropyl, methylthiobutyl, ethylthiobutyl, propylthiobutyl, butylthiobutyl, methylthiopentyl, ethylthiopentyl, propylthiopentyl, methylthiohexyl, ethylthiohexyl, methylthioheptyl, and the like; alkylsulfinylalkyl groups such as methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, butylsulfinylmethyl, pentylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylethyl, propylsulfinylethyl, butylsulfinylethyl, methylsulfinylpropyl, ethylsulfinylpropyl, propylsulfinylpropyl, methylsulfinylbutyl, ethylsulfinylbutyl, methylsulfinylpentyl, and the like; alkylsulfonylalkyl groups such as methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, butylsulfonylmethyl, pentylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl, propylsulfonylethyl, butylsulfonylethyl, methylsulfonylpropyl, ethylsulfonylpropyl, propylsulfonylpropyl, methylsulfonylbutyl, ethylsulfonylbutyl, methylsulfonylpentyl, and the like; alkoxyalkoxyalkyl groups such as methoxymethoxymethyl, ethoxymethoxymethyl, propoxymethoxymethyl, butoxymethoxymethyl, pentyloxymethoxymethyl, hexyloxymethoxymethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propoxyethoxyethyl, butoxyethoxyethyl, and the like; hydroxycarbonylalkyl groups such as hydroxycarbonylmethyl, hydroxycarbonylethyl, and the like; alkoxycarbonylalkyl groups such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propoxycarbonylethyl, and the like; a benzyl group; substituted benzyl groups such as chlorobenzyl groups having the substituent in the o-, m-or p-position, bromobenzyl groups having the substituent in the o-, m-or p-position, ethylbenzyl groups having the substituent in the o-, m- or p-position, propylbenzyl groups having the substituent in the o-, m-or p-position, and the like; an α-methylbenzyl group; a phenethyl group; etc. As a preferable substituent for R 1 , there can be exemplified haloalkyl groups such as 2-chloro-1,1,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 2,2,2-trifluoroethyl, 3-chloropropyl, 3-bromopropyl, 3-fluoropropyl, 2,2-difluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, 4-chlorobutyl, 4-fluorobutyl, 5-chlorobutyl, 5-fluorobutyl, and the like. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     As to a process for producing the compound represented by the general formula (I) of this invention, it can be produced, for example, by the following process: ##STR8## wherein R, R 1  and X have the same meanings as defined above, and Z is a halogen atom. 
     That is to say, the compound of the general formula (I) can be obtained by reacting a compound represented by the general formula (II) with a compound represented by the general formula (III) in the presence of an inert solvent. 
     As the inert solvent used in the reaction of this invention, any one may be used so long as it does not inhibit the progress of such a rection greatly. There can be exemplified, for example, aromatic hydrocarbons such as benzene, toluene, xylene and the like; aliphatic hydrocarbons such as n-hexane, cyclohexane and the like; alcohols such as methanol, ethanol, propanol, glycol and the like; ketones such as acetone, methyl ethyl ketone, cyclohexanone and the like; lower fatty acid esters such as ethyl acetate and the like; ethers such as tetrahydrofuran, dioxane and the like; lower fatty acid amides such as dimethylformamide, dimethylacetamide and the like; water; dimethylsulfoxide; etc. 
     These solvents are used alone or as a mixture thereof. 
     As the base usable in this invention, there can be exemplified, for example, inorganic bases such as sodium carbonate, sodium hydride, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydroxide, potassium hydroxide, alcoholates of alkali metals and the like; and organic bases such as pyridine, trimethylamine, triethylamine, diethylaniline, 1,8-diazabicyclo-[5,4,0]-7-undecene and the like. 
     The reaction of this invention can be carried out at a temperature properly selected, for example, in the range of 0° C. to 150° C. 
     Although the reaction of the compounds in each reaction path is an equimolar reaction, either of the compounds may be added in a slight excess. 
     The reaction time is selected preferably in the range of 0.5 to 48 hours. 
     After completion of the reaction, the desired compound can be collected by treating the reaction product by a conventional method. 
     The compound of the general formula (I) can be produced also according to the following formulas: ##STR9## wherein R, R 1  and X have the same meanings as defined above, and R 4  is a hydroxyl group or a halogen atom. 
     That is to say, the compound of the general formula (I) can be obtained by reacting a compound represented by the general formula (I-a) with the corresponding alcohol. 
     A compound of the general formula (I) in which R is a lower alkylsulfinylalkyl group or a lower alkylsulfonylalkyl group can be obtained also by oxydizing a compound of the general formula (I) in which R is a lower alkylthioalkyl group by using a suitable oxidizing agent. 
     Typical examples of the compounds of the general formula (I) are as shown in Table 1. 
     General formula (I): ##STR10## 
     
                                           TABLE 1__________________________________________________________________________CompoundNo.   R            R.sup.1                    X Physical properties__________________________________________________________________________1     H            CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.52002     H            CF.sub.2 CHClF                    Cl                      NMR: δ.sub.TMS.sup.CDCl 3 (ppm)                      1.65 (d, 3H), 2.40                      (t, 3H), 4.70 (q,                      1H), 6.95 (s, 1H),                      7.50 (s, 1H), 6.70-                      7.80 (m, 1H),                      9.00 (s, 1H)3     H            CF.sub.2 CHF.sub.2                    F n.sub.D.sup.24 1.50794     H            CF.sub.2 CClF                    F m.p. 107.8° C.5     H            CH.sub.2 CF.sub.3                    F m.p. 180.9° C.6     Na           CF.sub.2 CHF.sub.2                    Cl                      m.p. 141.8° C.7     Na           CF.sub.2 CHF.sub.2                    F m.p. 178.9° C.8     Na           CF.sub.2 CHClF                    F m.p. 145.8° C.9     K            CF.sub.2 CHF.sub.2                    Cl                      m.p. 201.4° C.10    K            CF.sub.2 CHF.sub.2                    F m.p. 103.3° C.11    (n-C.sub.4 H.sub.9).sub.2 NH.sub.2              CF.sub.2 CHF.sub.2                    Cl                      m.p. 192.8° C.12    (n-C.sub.4 H.sub.9).sub.2 NH.sub.2              CF.sub.2 CHF.sub.2                    F m.p. 171.0° C.13    CH.sub.3     CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.507214    CH.sub.3     CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.526215    CH.sub.3     CF.sub.2 CHF.sub.2                    F n.sub.D.sup.23 1.497716    C.sub.2 H.sub.5              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.23 1.503917    C.sub.2 H.sub.5              CH.sub.2 CF.sub.3                    Cl                      n.sub.D.sup.22 1.515018    C.sub.2 H.sub.5              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.24 1.489119    C.sub.2 H.sub.5              CH.sub.2 CF.sub.3                    F n.sub.D.sup.19.5 1.503020    C.sub.2 H.sub.5              CF.sub.2 CHClF                    F n.sub.D.sup.22 1.506221    n-C.sub.3 H.sub.7              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.23 1.499822    s-C.sub.4 H.sub.9              CF.sub.2 CHClF                    F n.sub.D.sup.23 1.498523    n-C.sub.6 H.sub.13              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.23 1.494024    n-C.sub.6 H.sub.13              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.483225    Cl(CH.sub.2).sub.2              CF.sub.2 CHF.sub. 2                    Cl                      n.sub.D.sup.24 1.516126    Cl(CH.sub.2).sub.2              CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.525327    Cl(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.18 1.504928    Br(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.522929    Br(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.509230    Br(CH.sub.2).sub.2              CF.sub.2 CHClF                    F n.sub.D.sup.23 1.519431    Cl(CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.513932    Cl(CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    F m.p. 48.5° C.33    Cl(CH.sub.2).sub.3              CF.sub.2 CHClF                    F n.sub.D.sup.23 1.510234    Cl(CH.sub.2).sub.3              CH.sub.2 CF.sub.3                    F m.p. 89.3°  C.35    Br(CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.521136    Br(CH.sub.2).sub.3              CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.529337    Br(CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.508838    Cl(CH.sub.2).sub.4              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.513539    Cl(CH.sub.2 ).sub.4              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.18 1.501240    Cl(CH.sub.2).sub.4              CF.sub.2 CHClF                    F n.sub.D.sup.23 1.508941              CF.sub.2 CHF.sub.2                    F m.p. 62.5° C.42  ##STR11##   CF.sub.2 CHClF                    F n.sub.D.sup.22 1.510243  ##STR12##   CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.505844  ##STR13##   CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.526845  ##STR14##   CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.496546  ##STR15##   CH.sub.2 CF.sub.3                    F n.sub.D.sup.19.5 1.505947    NCCH.sub.2 CH.sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.507548    NCCH.sub.2 CH.sub.2              CF.sub.2 CHF.sub.2                    F m.p. 83.8° C.49    CH.sub.2CHCH.sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.508450    CH.sub.2CHCH.sub. 2              CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.526251    CH.sub.2CHCH.sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.496452    CH.sub.2CHCH.sub.2              CH.sub.2 CF.sub.3                    F n.sub.D.sup.19.9 1.512253    CHCCH.sub.2  CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.512654    CHCCH.sub.2  CF.sub.2 CHF.sub.2                    F n.sub.D.sup.23 1.502555    CHCCH.sub.2  CF.sub.2 CHClF                    F n.sub.D.sup.22 1.513056    CH.sub.3 O(CH.sub.2).sub.2              CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.523057    CH.sub.3 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.19 1.493958    CH.sub.3 CH.sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.499059    CH.sub.3 CH.sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.487560    CH.sub.3 CH.sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHClF                    F n.sub.D.sup.22 1.502261    n-C.sub.4 H.sub.9 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.494462    n-C.sub.4 H.sub.9 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.23 1.484963    CH.sub.3 S(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.522264    CH.sub.3 S(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.18 1.512865    CH.sub.3 CH.sub.2 S(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.519766    CH.sub.3 CH.sub.2 S(CH.sub.2).sub.2              CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.532667    i-C.sub.3 H.sub.7 S(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.24 1.514568    i-C.sub.4 H.sub.9 S(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.25 1.502269    C.sub.2 H.sub.5 S(CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.25 1.506170    n-C.sub.4 H.sub.9 S(CH.sub.2).sub.3              CF.sub.2 CHClF                    F n.sub.D.sup.23 1.510371    CH.sub.3 SO(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.25 1.519572    i-C.sub. 4 H.sub.9 SO(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.25 1.503873    CH.sub.3 CH.sub.2 SO.sub.2 (CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.25 1.506174    i-C.sub.4 H.sub.9 SO.sub.2 (CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.25 1.502275    C.sub.2 H.sub.5 SO.sub.2 (CH.sub.2).sub.3              CF.sub.2 CHF.sub.2                    F m.p. 122.3°  C.76    CH.sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.28 1.498277    CH.sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHF.sub.2                    F n.sub.D.sup.24 1.488078    CH.sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.2              CF.sub.2 CHClF                    F n.sub.D.sup.22 1.500579  ##STR16##   CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.19 1.502780  ##STR17##   CF.sub.2 CHF.sub.2                    F n.sub.D.sup.23 1.491881  ##STR18##   CF.sub.2 CHClF                    F n.sub.D.sup.23 1.498982  ##STR19##   CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.25 1.532583  ##STR20##   CF.sub.2 CHClF                    Cl                      n.sub.D.sup.23 1.538984  ##STR21##   CF.sub.2 CHF.sub.2                    F m.p. 91.6° C.85  ##STR22##   CF.sub.2 CHF.sub.2                    Cl                      m.p. 119.3° C.86  ##STR23##   CH.sub.2 CF.sub.3                    Cl                      n.sub.D.sup.22 1.543387  ##STR24##   CF.sub.2 CHF.sub.2                    F n.sub.D.sup.18 1.532988  ##STR25##   CF.sub.2 CHClF                    F n.sub.D.sup.23 1.538689  ##STR26##   CF.sub.2 CHF.sub.2                    F n.sub.D.sup.26 1.520090  ##STR27##   CF.sub.2 CHF.sub.2                    Cl                      n.sub.D.sup.25 1.528291  ##STR28##   CF.sub.2 CHF.sub.2                    F n.sub.D.sup.23 1.5203__________________________________________________________________________ 
    
     The compound of the general formula (II) can be synthesized by the following reaction path: ##STR29## wherein R 1 , Z and X are as defined above; each of R 2  and R 3  is a lower alkyl group; A is an oxygen atom or a sulfur atom; and Z 1  &#39;s which may be the same or different are halogen atoms. 
     In detail, the compound of the general formula (II) can be obtained by reacting a compound represented by the general formula (X) with a compound represented by the general formula (IX) with heating in an inert solvent, either isolating or not isolating the resulting compound represented by the general formula (VIII), subjecting this compound to ring closure reaction in the presence of a base to convert the same into a compound represented by the general formula (VII), reacting said compound (VII) with a halide represented by the general formula (V) or (VI) to obtain a compound represented by the general formula (IV), and reacting said compound (IV) with hydrogen bromide. 
     In producing the compound of the general formula (II) from the compound of the general formula (IV), hydrogen iodide or an alkyl thiolate may be used in place of hydrogen bromide. 
     Examples of this invention are given below not by way of limitation but by way of illustration. 
    
    
     EXAMPLE 1 
     4-(2-Chloro-1,1,2-trifluoroethyl)-1-{[2,4-dichloro-5-(1-methoxycarbonyl)ethoxy]phenyl}-3-methyl-Δ 2  -1,2,4-triazolin-5one (Compound No. 14) ##STR30## 
     In 50 ml of methanol was dissolved 0.62 g (0.011 mole) of KOH, and 3.6 g (0.01 mole) of 4-(2-chloro-1,1,2-trifluoroethyl)-1-(2,4-dichloro-5-hydroxyphenyl)-3-methyl-Δ 2  -1,2,4-triazolin-5-one was added to the resulting solution to be converted into its potassium salt. Then, 1.83 g (0.011 mole) of methyl α-bromopropionate was added, and the resulting mixture was refluxed with heating for 3 hours. After completion of the reaction, the reaction mixture was poured into ice water, and the resulting mixture was extracted with ether, after which the extract was concentrated to obtain 4.0 g of the desired compound: n D   23  1.5262, yield 88.9%. 
     EXAMPLE 2 
     1-[4-Chloro-5-(1-ethoxycarbonyl)ethoxy-2-fluorophenyl]-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one (Compound No. 18) ##STR31## 
     In 150 ml of acetone were suspended 9.0 g (0.026 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one, 7.9 g (0.044 mole) of ethyl α-bromopropionate and 9.0 g of potassium carbonate, and the resulting suspension was refluxed with heating for 2 hours. After completion of the reaction, the reaction suspension was cooled to room temperature. Then, the insoluble materials were removed by filtation, after which the filtrate was concentrated and the residue was purified by column chromatography to obtain 9.22 g of the desired compound. 
     Physical properties: n D   24  1.4891, yield 79.3%. 
     EXAMPLE 3 
     1-{5-[1-(3-Chloropropoxycarbonyl)ethoxy]-2,4-dichlorophenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one (Compound No. 31) ##STR32## 
     In 40 ml of anhydrous dimethylsulfoxide was dissolved 1.8 g (0.0051 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one, and 0.3 g (0.0053 mole) of powdered potassium hydroxide was added to the resulting solution. The mixture thus obtained was stirred for 30 minutes, after which 1.0 g (0.0053 mole) of 3-chloropropyl α-chloropropionate was added, and the reaction was carried out at 80° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into ice water, and the reaction product was extracted therefrom with diethyl ether. The extract was washed with water and dried. Then, the diethyl ether was removed by distillation to obtain 2.3 g of the desired compound: n D   24  1.5139, yield 89%. 
     EXAMPLE 4 
     1-{4-Chloro-5-[1-(3-chloropropoxycarbonyl)ethoxy]-2-fluorophenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one (Compound No. 32) ##STR33## 
     In 50 ml of N,N-dimethylformamide was suspended 0.52 g (0.0037 mole) of potassium carbonate, and 1.17 g (0.0034 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one was added to the resulting suspension. The resulting mixture was stirred at room temperature for 30 minutes, after which 0.85 g (0.0034 mole) of 3-chloroporpyl α-bromopropionate was added, and the reaction was carried out at 50° C. for 3 hours. After completion of the reaction, the reaction mixture was adjusted to room temperature and poured into ice water, and the reaction product was extracted therefrom with diethyl ether. The extract was washed with water and dried. Then, the diethyl ether was removed by distillation to obtain an oily substance. The oily substance obtained was purified by a silica gel column chromatography (ether : n-hexane=1:2) and allowed to stand at room temperature to obtain 1.36 g of the desired product as crystals: m.p. 48.5° C., yield 82%. 
     EXAMPLE 5 
     4-(2-Chloro-1,1,2-trifluoroethyl)-1-{2,4-dichloro-5-[1-((2-ethylthio)ethoxycarbonyl)ethoxy]phenyl}3-methyl-Δ 2  -1,2,4-triazolin-5-one (Compound No. 66) ##STR34## 
     In 30 ml of tetrahydrofuran was suspended 0.15 g (0.0037 mole) of 60% NaH, and 1.26 g (0.0034 mole) of 4-(2-chloro-1,1,2-trifluoroethyl)-1-(2,4-dichloro-5-hydroxyphenyl)-3-methyl)-Δ 2  -1,2,4-triazolin-5-one was added to the resulting suspension. The mixture thus obtained was stirred for 30 minutes, after which 0.89 g (0.0037 mole) of (2-ethylthio)ethyl α-bromopropionate was added, and the resulting mixture was refluxed with heating for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then poured into ice water, and the reaction product was extracted therefrom with diethyl ether. The extract was washed with water and dried. Then, the diethyl ether was removed by distillation, and the residue was purified by dry column chromatography to obtain 1.33 g of the desired compound: n D   23  1.5326, yield 75%. 
     EXAMPLE 6 
     1-{4-Chloro-5-[1-(4-chlorobenxzyloxycarbonyl)ethoxy]-2-fluorophenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one (Compound No. 87) ##STR35## 
     To 50 ml of methyl ethyl ketone were added 1.75 g (0.0051 mole) of 1-(4-chloro-1-fluoro-5-hydroxyphenyl)-3-methyl-4-(1,1,2,2,-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one, 1.5 g of potassium carbonate and 1.27 g (5.6 m moles) of 4-chlorobenzyl α-bromopropionate, and the resulting mixture was refluxed with heating for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the insoluble materials were removed by filtration, and the filtrate was concentrated, after which the residue was purified by dry column chromatography to obtain 1.87 g of the desired compound: n D   18  1.5329, yield 68%. 
     EXAMPLE 7 
     Sodium 1-{2,4-dichloro-5-[3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-on-1-yl]phenoxy}propionate (Compound No. 6) ##STR36## 
     In 30 ml of methanol was dissolved 4.32 g (0.01 mole) of 1-{2,4-dichloro-5-[1-hydroxycarbonyl)ethyoxy]phenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  1,2,4-triazolin-5-one, and 2 ml of an aqueous solution of 0.4 g (0.01 mole) of NaOH was added to the resulting solution. The solution thus obtained was stirred at room temperature for 30 minutes, after which the solvent was removed by distillation, and the crystals thus obtained were washed with ether and then dried to obtain 4.53 g of the desired compound: m.p. 141.8° C., yield 100%. 
     EXAMPLE 8 
     1-{2,4-Dichloro-5-[1-(2-methylsulfinyl)ethoxycarbonyl]ethyoxyphenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one (Compound No. 71) ##STR37## 
     In 100 ml of methylene dichloride was dissolved 5.05 g (0.01 mole) of 1-{2,4-dichloro-5-[1-(2-methylthio)ethoxycarbonyl]ethoxyphenyl}-3-methyl-4-(1,1,2,2-tetrafluoroethyl)-Δ 2  -1,2,4-triazolin-5-one, and 2.0 g (0.0106 mole) of m-chloroperbenzoic acid was added. The resulting mixture was subjected to reaction at room temperature for 5 hours, after which the reaction mixture was poured into ice water, and the methylene chloride layer was treated by a conventional method to obtain 48 g of the desired compound: n D   25  1.5195, yield 92.1%. 
     The Δ 2  -1,2,4-triazolin-5-one derivatives represented by the general formula (I) of this invention are capable of controlling annual and perennial weeds grown in paddy fields, for example, barnyard grass (Echinochloa crus-galli Beauv., an annual weed of Gramineae family which is a typical strongly injurious weed grown in paddy fields), monochoria (Monochoria vaginalis Presl, a strongly injurious annual weed of Pontederiaceae family grown in paddy fields), smallflower umbrellaplant (Cyperus difformis L., and injurious annual weed of Cyperaceae family grown in paddy fields), water nutgrass Cyperus serotinus Rottb., a typical injurious perennial weed of Cyperaceae family grown in paddy fields, and also grown in swamps and waterways), arrowhead (Sagittaria pygmaea Mig., an injurious perennial weed of Alismataceae family, grown in paddy fields, swamps and ditches), bulrush (Scirpus juncoids Roxb. var Hotarui Ohwi, a perennial weed of Cyperaceae family, grown in paddy fields, swamps and ditches); and annual and perennial weeds grown in upland fields and orchards, for example, wild oats (Avena fatua L., an annual weed of Gramineae family, grown in plains, waste lands and upland fields), mugwort (Artemisia princeps Pamp., a perennial weed of Compositae family, grown in cultivated and uncultivated fields), large crabgrass (Digitaraia adscendcue Henr., an annual weed of Gramineae family which is a typical strongly injurious weed grown in upland fields and orchards), curly dock (Rumex japonicus Houttuyn, a perennial weed of Polygonaceae family, grown in upland fields and on roadsides), umbrella sedge (Cyperus iria L., an annual weed of Cyperaceae family, grown in upland fields and on roadsides), redroot pigweed (Amaranthus varidis L., an annual weed of Amaranthaceae family grown in upland fields, vacant lands and roadsides), and cocklebur (Xanthium strumarium L., an annual weed of Compositae family, strongly injurious to soybeans). 
     Since, the triazolin-5-one derivatives represented by the above general formula (I) exhibit excellent controlling effects against weeds of both pre-and post-emergence stages, they are useful, for example, as herbicides for soil treatment before and after seeding (planting), for soil treatment in the growth period, for foliar treatment before seeding (planting), for foliar treatment in the growth period of useful upland crops such as soybeans, cotton, corns and the like. Furthermore, the compounds of this invention are useful as herbicides applying at the pre-emegence stage and the post-emergence stage of weeds in paddy fields, moreover, they are useful as herbicides to control general weeds grown in for example, mowed fields, paddy fields and upland fields in fallow, ridges between paddy fields, agricultural pathways, waterways, pasture, graveyards, parks, roads, playgrounds, unoccupied areas around buildings, reclaimed lands, railways and forests. Herbicidal treatments of such areas are carried out most effectively and economically when weeds are not emergent but not necessarily be done prior to the emergence of weeds. 
     For applying the compounds of the present invention as herbicides, they are generally formulated, according to conventional procedures for preparing agricultural compositions, into a form convenient to use. 
     That is to say, said compounds are mixed with suitable inert carriers and, if necessary, further mixed with adjuvants, in a suitable ratio, and through dissolution, dispersion, suspension, mechanical mixing, impregnation, adsorption or adhesion, to make to mixture into a suitable form of composition, e.g., suspensions, emulsifiable concentrates, solutions, wettable powders, dusts, granules or tablets. 
     The inert carriers usable in this invention may be either solid or liquid. As materials usable as the solid carriers, there can be examplified, for example, vegetable powders such as soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobaco stalks, powdered walnut shell, bran, powdered cellulose, and extraction residues of vegetables; fibrous materials such as paper, corrugated paperboard, and waste cloths; synthetic polymers such as powdered synthetic resins; inorganic or mineral products such as clays (e.g., kaolin, bentonite and acid clay), talc products (e.g., talc and pyrophyllite), silica products [e.g., diatomaceous earth, silica sand, mica and white carbon (a highly dispersed synthetic silicic acid, also called as finely pulverized hydrated silica or hydrated silicic acid, and some commercially available products contain calcium silicate as the major component)], activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, and calcium phosphates; chemical fertilizers such as ammonium sulfate, ammonium phosphates, ammonium nitrate, urea, and ammonium chloride, and farmyard manures. These solid carriers may be used alone or as a mixture thereof. Materials usable as the liquid carriers are selected from those which are solvents for the active ingredients and those which are non-solvnet but can disperse the active ingredients with the aid of adjuvants. They include, for example, the following materials, which may be used alone or as a mixture thereof: water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, and ethylene glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone), ethers (e.g., ethyl ether, dioxane, cellosolves, dipropyl ether, and tetraphydrofuran), aliphatic hydrocarbons (e.g., gasoline and mineral oils), aromatic hydrocarbons (e.g., benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene), halogenated hydrocarbones (e.g., dichloroethane, chlorinated benzenes, chloroform and carbon tetrachloride), esters (e.g., ethyl acetate, dibutyl phthalate, diisopropyl phthanate, and dioctyl phthalate), acid amides (e.g., dimethylformamide, diethylformamide, and dimethylacetamide), and nitriles (e.g., acetonitrile), and dimethyl sulfoxide. 
     As the adjuvants, the following can be examplified. These adjuvants are used depending on purposes. In some cases, two or more of the adjuvants are simultaneously used. In some other cases, no adjuvant is used at all. For the purpose of emulsification, dispersion, solubilization and/or wetting of the active ingredients, there can be used furface active agents, for example, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates, and higher alcohol sulfate esters. For the purpose of stabilizing the dispersion, tackification and/or agglomeration of the active ingredients, the following materials may be use, for example, casein, gelatin, starch, alginic acid, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine root oil, rice bran oil, bentonite and ligninsulfonates. 
     For the purpose of improving the flowability of the solid compositions, it is recommendable to use waxes, stearates, alkyl phosphates, etc. 
     As to peptizers for dispersible compositions, it is also recommendable to use naphthalenesulfonic acid condensation products, condensed phosphates, etc. 
     It is also possible to add anti-foaming agents, for example, a silicone oil. 
     The content of the active ingredients in the herbicidal composition may be adjusted depending on the applications. In general, it is suitably 0.5 to 20% by weight for preparing a powdered or granulated product, and 0.1 to 50% by weight for preparing an emulsifiable concentrate or a wettable powder product. 
     For destroying various weeds, inhibiting their growth, or protecting useful plants from the injury caused by these weeds, the herbicidal composition of the present invention is applied in a weed-destroying dosage or a weed growth inhibiting dosage as such or after being properly diluted with or suspended in water or in other suitable medium, to the soil or the foliage of weeds in the area where the emergence or growth of weeds is undesirable. 
     The amount of the herbicidal composition of the present invention used is varied depending on various factors, for example, the purpose of application, the objective weeds, the emergence or growth state of weeds and crops, the emergence tendency of weeds, weather, environmental conditions, the type of herbicidal formulations, the way of application, the type of the field to be treated, and the time of application and others. 
     When the herbicidal composition of this invention is applied alone as a selective herbicide, it is suitable, for example, to select the dosage of the compound of this invention in the range of 0.1 to 500 g per 10 ares. On the other hand, when the herbicidal composition of this invention is applied together with other herbicides, the dosage of the compound of this invention can be selected in a still smaller dosage range when it is taken into consideration that said composition is often effective in a smaller dosage than when it is used alone. 
     Herbicidal composition of the present invention is especially valuable for the pre-emergence treatment and initial emergence stage treatment of upland fields and for the control of weeds at pre-emergence stage and post-emergence stage in paddy fields. In order to expand both spectrum of controllable weed species and the period of time when effective applications are possible or to reduce the dosage, the herbicidal composition of the present invention can be used in combination with other herbicides, and this usage is within the scope of the present invention. For example, herbicidal composition of the present invention can be used in combination with one or more of the following herbicides: phenoxy fatty acid type herbicides, for example, 2,4-PA (e.g., ethyl (2,4-dichlorophenoxy)acetate), MCP (e.g., ethyl (2-methyl-4-chlorophenoxy)acetate, sodium (2-methyl-4-chlorophenoxy)acetate, and allyl (2-methyl-4-chlorophenoxy)acetate), MCPB (ethyl (2-methyl-4-chlorophenoxy)butyrate), and Diclofop-methyl (methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate); diphenyl ether type herbicides, for example, NIP (2,4-dichlorophenyl-4&#39;-nitrophenyl ether), CNP (2,4,6-trichlorophenyl-4&#39;-nitrophenyl ether), Chlomethoxynil (2,4-dichlorophenyl-3&#39;-methoxy-4&#39;-nitrophenyl ether), Acifluorgen [5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid and its salts], and Fluazifop-butyl (butyl (±)-2-[4-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenoxy]propionate); triazine type herbicides, for example, CAT (2-chloro-4,6-bis(ethylamino)-s-triazine), Prometryne (2-methylthio-4,6-bis(isopropylamino)-s-triazine, Simetryne (2-methylthio-4,6-bis(ethylamino)-s-triazine), and Metribuzin (4-amino-6-tert-butyl-3-methylthio-1,2,4-tirazin-5(4H)-one); carbamate type herbicides, for example, Molinate (s-ethyl hexahydro-1H-azepine-1-carbothioate), MCC (methyl N-(3,4-dichlorophenyl)carbamate), IPC (isopropyl N-(3-chlorophenyl)carbamate), and Benthiocarb (s-(4-chlorobenzyl)dimethylthiocarbamate); toluidine type herbicides, for example, Triefluraline (α,α, α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) and Pendimethaline (N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine); Acid amide type herbicides, for example, DCPA (3,4-dichloropropionanilide), Butachlor (2-chloro-2&#39;,6&#39;-diethyl-N-(butoxymethyl)-acetanilide), Alachlor (2-chloro-2&#39;,6&#39;-diethyl-N-(methoxyethyl)acetanilide), Metolachlor (2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide), and Pretilachlor (2-chloro-2&#39;,6&#39;-diethyl-N-(2-propoxyethyl)acetanilide); and other types of herbicides, for example, DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea), Bentazon (3-isopropyl-(1H)-2,1,3-benzothiazin-4(3H)-one-2,2-dioxide), Pyrazolate (4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate), Pyrazoxyfen (1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-phenacyloxypyrazol), and MY-71 (4-(2,4-dichloro-3-methylbenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate). 
     Some test examples and preparation examples are given below not by way of limitation but by way of illustration. 
     Test Example 1 
     Effect on paddy field weeds of pre-emergence stage 
     Pots (1/10,000 - are) ) were filled with soil to simulate a paddy field, and planted with seeds of barnyard grass, monochoria, umbrella plant, and bulrush, and with tubers of arrowhead, respectively, which are all injurious weeds grown in paddy, fields, and the seeds and tubers were conditioned so as to be in preemergence stage. 
     The soil in the pot was treated with each of the active ingredients (the compounds listed in Table 1) formulated to given concentration of liquid, by spraying. After 21 days, the percent control of weed growth compared with that on the untreated plot was observed and the herbicidal activity was determined according to the following criterion: 
     Criterion for determining herbicidal activity 
     
         ______________________________________Degree of    Percent control ofherbicidal   weed growthactivity     (%)______________________________________5            1004            90-993            80-892            70-791            Less than 70______________________________________ 
    
     The results obtained are shown in Table 2. 
     
                                           TABLE 2__________________________________________________________________________   Amount of   active  Effect of pre-emergence treatmentCompound   ingredient           Barnyard      UmbrellaNo.     g/are   grass Monochoria                         plant Bulrush                                     Arrowhead__________________________________________________________________________1       30      5     5       5     5     5   3       4     5       5     5     52       30      5     5       5     5     5   3       4     5       5     5     53       30      5     5       5     5     5   3       5     5       5     5     54       30      5     5       5     5     5   3       5     5       5     5     55       30      5     5       5     5     5   3       5     5       5     5     56       30      5     5       5     5     5   3       5     5       5     5     57       30      5     5       5     5     5   3       5     5       5     5     58       30      5     5       5     5     5   3       5     5       5     5     59       30      5     5       5     5     5   3       5     5       5     5     510      30      5     5       5     5     5   3       4     5       5     4     411      30      5     5       5     5     5   3       5     5       5     5     512      30      5     5       5     5     5   3       5     5       5     4     513      30      5     5       5     5     5   3       5     5       5     5     514      30      5     5       5     5     5   3       5     5       5     5     515      30      5     5       5     5     5   3       5     5       5     5     516      30      5     5       5     5     5   3       5     5       5     5     517      30      5     5       5     5     5   3       5     5       5     5     518      30      5     5       5     5     5   3       5     5       5     5     519      30      5     5       5     5     5   3       5     5       5     5     520      30      5     5       5     5     5   3       5     5       5     5     521      30      5     5       5     5     5   3       5     5       5     5     522      30      5     5       5     5     5   3       5     5       5     5     523      30      5     5       5     5     5   3       5     5       5     5     524      30      5     5       5     5     5   3       5     5       5     5     525      30      5     5       5     5     5   3       5     5       5     5     526      30      5     5       5     5     5   3       5     5       5     5     527      30      5     5       5     5     5   3       5     5       5     5     528      30      5     5       5     5     5   3       5     5       5     5     529      30      5     5       5     5     5   3       5     5       5     5     530      30      5     5       5     5     5   3       5     5       5     5     531      30      5     5       5     5     5   3       4     5       5     5     532      30      5     5       5     5     5   3       5     5       5     5     533      30      5     5       5     5     5   3       5     5       5     5     534      30      5     5       5     5     5   3       5     5       5     5     535      30      5     5       5     5     5   3       5     5       5     5     536      30      5     5       5     5     5   3       5     5       5     5     537      30      5     5       5     5     5   3       5     5       5     5     538      30      5     5       5     5     5   3       5     5       5     5     539      30      5     5       5     5     5   3       5     5       5     5     540      30      5     5       5     5     5   3       5     5       5     5     541      30      5     5       5     5     5   3       5     5       5     5     542      30      5     5       5     5     5   3       5     5       5     5     543      30      5     5       5     5     5   3       5     5       5     5     544      30      5     5       5     5     5   3       5     5       5     5     545      30      5     5       5     5     5   3       5     5       5     5     546      30      5     5       5     5     5   3       5     5       5     5     547      30      5     5       5     5     5   3       5     5       5     4     548      30      5     5       5     5     5   3       5     5       5     5     549      30      5     5       5     5     5   3       5     5       5     4     550      30      5     5       5     5     5   3       5     5       5     5     551      30      5     5       5     5     5   3       5     5       5     5     552      30      5     5       5     5     5   3       5     5       5     5     553      30      5     5       5     5     5   3       4     5       5     5     554      3-      5     5       5     5     5   3       5     5       5     5     555      30      5     5       5     5     5   3       5     5       5     5     556      30      5     5       5     5     5   3       5     5       5     5     557      30      5     5       5     5     5   3       5     5       5     5     558      30      5     5       5     5     5   3       5     5       5     5     559      30      5     5       5     5     5   3       5     5       5     5     560      30      5     5       5     5     5   3       5     5       5     5     561      30      5     5       5     5     5   3       5     5       5     5     562      30      5     5       5     5     5   3       5     5       5     5     563      30      5     5       5     5     5   3       4     5       4     4     564      30      5     5       5     5     5   3       5     5       5     5     565      30      5     5       5     5     5   3       4     5       4     4     566      30      5     5       5     5     5   3       5     5       5     5     567      30      5     5       5     5     5   3       4     4       4     4     568      30      5     5       5     5     5   3       5     5       5     5     569      30      5     5       5     5     5   3       5     5       5     5     570      30      5     5       5     5     5   3       5     5       5     5     571      30      5     5       5     5     5   3       5     5       5     5     572      30      5     5       5     5     5   3       5     5       5     5     573      30      5     5       5     5     5   3       5     5       5     5     574      30      5     5       5     5     5   3       5     5       5     5     575      30      5     5       5     5     5   3       5     5       5     5     576      30      5     5       5     5     5   3       4     5       5     5     577      30      5     5       5     5     5   3       5     5       5     5     578      30      5     5       5     5     5   3       5     5       5     5     579      30      5     5       5     5     5   3       5     5       5     5     580      30      5     5       5     5     5   3       5     5       5     5     581      30      5     5       5     5     5   3       5     5       5     5     582      30      5     5       5     5     5   3       5     5       5     5     583      30      5     5       5     5     5   3       5     5       5     5     584      30      5     5       5     5     5   3       5     5       5     5     585      30      5     5       5     5     5   3       5     5       5     5     586      30      5     5       5     5     5   3       5     5       5     5     587      30      5     5       5     5     5   3       5     5       5     5     588      30      5     5       5     5     5   3       5     5       5     5     589      30      5     5       5     5     5   3       5     5       5     5     590      30      5     5       5     5     5   3       5     5       5     5     591      30      5     5       5     5     5   3       5     5       5     5     5Compound A   30      5     5       5     5     5   3       3     4       4     3     3Compound B   30      4     5       5     4     5   3       1     4       5     1     3Compound C   3       3     4       4     3     3__________________________________________________________________________ As reference Compound A, Compound 7 (1(2,4-dichloro-5-((1-ethoxycarbonyl)-ethoxy)phenyl)-4-difluoromethyl-3-mthyl-Δ.sup.21,2,4-triazolin-5-one) disclosed in Japanese Patent Koka No. 57181069 (1982) was tested, respectively. .sup.*1 Compound B, Compound No. 62 1[2,4dichloro-5-(1-ethoxycarbonyl)ethoxyphenyl4-ethyl-3-methyl-Δ.su.2 1,2,4triazolin-5-one disclosed in U.S. Pat. No. 4318731 .sup.*2 Compound C, Compound No. 5 1(2,4-dichloro-5-isopropoxyphenyl)-4-difluoromethyl-3-methyl-Δ.sup.1,2,4-triazolin-5-one disclosed in U.S. Pat. No. 4398943 
    
     Test Example 2 
     Effect on paddy field weeds of post-emergence stage 
     Pots (1/10,000 - are) were filled with soil to simulate a paddy field and grown with each of injurious weeds of the following leaf age. In addition, young seedings of rice plant (cultivar: &#34;Nihonbare&#34;) of the 2.5 leaf age were transplanted to the soil on the day before the treatment with each of the present herbicides, and treated with the herbicides. After 21 days, the herbicidal effect and the degree of crop injury to the rice plant were evaluated by comparing the results with those on the untreated plot. 
     
         ______________________________________Species of weed tested           Leaf age of the weed______________________________________Barnyard grass  1Monochoria      2-3Umbrella plant  1-2Bulrush         2-3Arrowhead       3Water nutgrass  1-2______________________________________ 
    
     The criterion for judging the degree of crop injury was as follows: 
     H: High (including withering) 
     M: Medium 
     L: Low 
     N: None 
     The criterion for judging the herbicidal activity was the same as in Test Example 1. The results obtained are shown in Table 3. 
     
                                           TABLE 3__________________________________________________________________________   Amount of   active  Effect of Post-emergence treatment CropCompound   ingredient           Barnyard                 Mono-                      Umbrella    Arrow-                                        Water injuryNo.     g/are   grass choria                      plant Bulrush                                  head  nutgrass                                              Rice__________________________________________________________________________1       30      5     5    5     5     5     5     L   3       3     5    5     4     4     4     N2       30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     N3       30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L4       30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     N5       30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L6       30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N7       30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L8       30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L9       30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N10      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     N11      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     N12      30      5     5    5     5     5     5     L   3       5     5    5     4     4     4     N13      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L14      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L15      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L16      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L17      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L18      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L19      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L20      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L21      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L22      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L23      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L24      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L25      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L26      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     L27      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     N28      30      5     5    5     5     5     5     L   3       4     5    5     5     4     5     L29      30      5     5    5     5     5     5     L   3       5     5    5     4     5     4     N30      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L31      30      5     5    5     5     5     5     L   3       3     5    5     4     5     5     L32      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L33      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L34      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L35      30      5     5    5     5     5     5     L   3       4     5    5     5     4     5     L36      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L37      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L38      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     L39      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L40      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     L41      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L42      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L43      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L44      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N45      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L46      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L47      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     N48      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     L49      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L50      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     N51      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L52      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L53      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L54      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L55      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L56      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N57      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L58      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L59      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L60      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L61      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L62      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     N63      30      5     5    5     5     5     5     L   3       4     5    5     4     3     5     L64      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L65      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     L66      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L67      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     N68      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     L69      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L70      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L71      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N72      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L73      30      5     5    5     5     5     5     L   3       4     5    5     4     5     5     N74      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L75      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L76      30      5     5    5     5     5     5     L   3       3     5    5     4     4     5     N77      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L78      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L79      30      5     5    5     5     5     5     L   3       4     4    5     4     5     5     N80      30      5     5    5     4     5     5     L   3       4     5    5     4     5     5     N81      30      5     5    5     5     5     5     L   3       5     5    5     5     5     5     L82      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     L83      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L84      30      5     5    5     5     5     5     L   3       4     5    5     4     4     5     N85      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L86      30      5     5    5     5     5     5     L   3       4     5    5     5     5     5     L87      30      5     5    5     5     5     5     L   3       5     5    5     5     5     4     L88      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L89      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     L90      30      5     5    5     5     5     5     L   3       4     4    5     4     5     5     L91      30      5     5    5     5     5     5     L   3       5     5    5     4     5     5     LCompound A   30      5     5    5     5     5     5     L   3       2     4    4     2     3     2     LCompound B   30      3     3    3     2     3     2     N   3       1     1    1     1     1     1     NCompound C   3       2     4    4     2     3     2     L__________________________________________________________________________ 
    
     Test Example 3 
     Effect on upland field weeds of pre-emergence stage 
     Polyethylene vats, having 10×20×5 cm (depth) size, were filled with soil and seeded with oats, barnyard grass, large crabgrass, redroot pigweed, mugwort, curly dock, umbrella sedge and cocklebur, respectively, which were all upland field weeds, and the seeds were covered with soil. 
     The soil was treated with each active ingredient formulated to a given concentration of liquid, by spraying. After 21 days, the herbicidal effect was evaluated by comparing the results with those on the untreated plot. 
     The criterion for judging the herbicidal activity was the same as in Test Example 1. The results obtained are shown in Table 4. 
     
                                           TABLE 4__________________________________________________________________________  Amount of        Effect of Pre-emergence treatment  active        LargeCompound  ingredient           Barnyard                crab-                    Redroot   Curly                                  UmbrellaNo.    (g/are)        Oats           grass                grass                    pigweed                         Mugwort                              dock                                  sedge                                       Cocklebur__________________________________________________________________________1      30    5  5    5   5    5    5   5    5  3     5  4    4   5    5    4   5    52      30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    43      30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    54      30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    4   5    55      30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    56      30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    57      30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    58      30    5  5    5   5    5    5   5    5  3     4  4    4   5    4    5   4    59      30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    510     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    511     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    512     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    513     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    514     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    515     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    516     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    417     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    518     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    519     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    520     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    521     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    522     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    523     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    4   5    424     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    525     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    426     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    527     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    528     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    4   5    429     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    530     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    531     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    4   5    532     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    533     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    534     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    535     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    536     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    537     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    538     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    4   5    539     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    540     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    541     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    542     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    543     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    544     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    545     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    546     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    547     30    5  5    5   5    5    5   5    5  3     4  4    4   5    5    5   5    548     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    549     30    5  5    5   5    5    5   5    5  3     3  5    5   5    5    5   5    550     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    551     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    552     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    553     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    454     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    555     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    556     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    557     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    558     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   4    559     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    560     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    561     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    562     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    563     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    464     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    565     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    566     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    567     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    468     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    569     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    570     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    571     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    572     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    573     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    574     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    575     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    576     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    477     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    578     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    579     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    580     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    581     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    582     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    583     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    5   5    584     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    585     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    4   5    586     30    5  5    5   5    5    5   5    5  3     3  4    5   5    5    5   5    587     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    588     30    5  5    5   5    5    5   5    5  3     4  5    5   5    5    5   5    589     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    590     30    5  5    5   5    5    5   5    5  3     4  4    5   5    5    4   5    591     30    5  5    5   5    5    5   5    5  3     5  5    5   5    5    5   5    5Compound A  30    2  4    4   5    5    5   5    4  3     1  2    3   5    4    3   4    2Compound B  30    2  2    4   5    5    4   5    3  3     1  1    2   4    3    2   5    1Compound C  3     2  3    3   5    4    3   4    1__________________________________________________________________________ 
    
     Test Example 4 
     Effect on upland field weeds of post-emergence stage 
     Polyethylene vats, having 10×20×5 cm (depth) size, were filled with soil and seeded with the injurious weeds shown below and soybean seeds, respectively, and the seeds were covered with soil. The weeds and soybean were cultivated respectively to the following leaf ages and then treated with each active ingredient at a given dosage. 
     After 21 days, the herbicidal effect on the weeds and the degree of corp injury to the soybean were evaluated by comparing the results with those on the untreated plot. 
     
         ______________________________________Species of test plant           Leaf age______________________________________Oats            2Large crabgrass 2Redroot pigweed 1Mugwort         1Curly dock      2Umbrella sedge  1Cocklebur       1Soybean         First trifoliate age______________________________________ 
    
     The criteria for judging the herbicidal activity and crop injury were the same as in Test Examples 1 and 2, respectively. The results obtained are shown in Table 5. 
     
                                           TABLE 5__________________________________________________________________________Amount of   Herbicidal effect of post-emergence treatment active   Large                     CropCompound ingredient          crab-              Redroot                   Mug-                       Curly                           Umbrella                                Cock-                                    injuryNo.   (g/are)       Oats          grass              pigweed                   wort                       dock                           sedge                                lebur                                    Soybean__________________________________________________________________________1     30    5  5   5    5   5   5    5   N 3     3  3   5    5   4   5    4   N2     30    5  5   5    5   5   5    5   N 3     3  4   5    5   5   5    5   N3     30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N4     30    5  5   5    5   5   5    5   N 3     3  4   4    5   5   5    5   N5     30    5  5   5    5   5   5    5   N 3     3  4   5    5   4   5    4   N6     30    5  5   5    5   5   5    5   N 3     4  4   5    5   4   5    5   N7     30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    4   N8     30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    4   N9     30    5  5   5    5   5   5    5   N 3     4  4   5    5   4   5    5   N10    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    4   N11    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N12    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    4   N13    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N14    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N15    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N16    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N17    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N18    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N19    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N20    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N21    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N22    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N23    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N24    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N25    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N26    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N27    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N28    30    5  5   5    5   5   5    5   L 3     3  4   5    5   4   5    5   N29    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N30    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N31    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N32    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N33    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N34    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N35    30    5  5   5    5   5   5    5   L 3     4  5   5    5   4   5    5   N36    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N37    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N38    30    5  5   5    5   5   5    5   L 3     4  4   5    5   4   5    5   N39    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N40    30    5  5   5    5   5   5    5   N 3     3  4   5    5   5   5    5   N41    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N42    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N43    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N44    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N45    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N46    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N47    30    5  5   5    5   5   5    5   N 3     4  4   5    5   4   5    5   N48    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N49    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N50    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N51    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N52    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N53    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N54    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   L55    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N56    30    5  5   5    5   5   5    5   N 3     3  4   5    5   5   5    5   N57    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N58    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   L59    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N60    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N61    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N62    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N63    30    5  5   5    5   5   5    5   L 3     4  4   5    5   4   5    5   N64    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N65    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N66    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N67    30    5  5   5    5   5   5    5   N 3     4  4   5    5   4   5    5   N68    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N69    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N70    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N71    30    5  5   5    5   5   5    5   N 3     3  4   5    5   4   5    5   N72    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N73    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N74    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N75    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N76    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N77    30    5  5   5    5   5   5    5   L 3     5  5   5    5   5   5    5   N78    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N79    30    5  5   5    5   5   5    5   L 3     4  4   5    5   5   5    5   N80    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   4    5   N81    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N82    30    5  5   5    5   5   5    5   L 3     4  5   5    5   5   5    5   N83    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N84    30    5  5   5    5   5   5    5   N 3     5  5   5    5   5   5    5   N85    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N86    30    5  5   5    5   5   5    5   N 3     3  4   5    5   5   5    5   N87    30    5  5   5    5   5   5    5   N 3     5  4   5    5   5   5    5   N88    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   N89    30    5  5   5    5   5   5    5   N 3     4  4   5    5   5   5    5   N90    30    5  5   5    5   5   5    5   N 3     3  4   5    5   5   5    5   N91    30    5  5   5    5   5   5    5   N 3     4  5   5    5   5   5    5   NCompound 30    3  5   5    5   5   5    4   LA     3     2  3   4    3   3   3    2   LCompound 30    4  2   5    4   4   5    4   NB     3     1  1   3    3   1   1    1   NCompound 3     2  3   4    3   2   3    2   L__________________________________________________________________________ 
    
     Preparation Example 1 
     A wettable powder composition was prepared by mixing uniformly and grinding the following ingredients: 
     
         ______________________________________Compound No. 1          50 PartsMixture of Clay and white                   45 Partscarbon (in which clayis contained as the majorcomponent)Polyoxyethylene nonylphenyl                    5 Partsether______________________________________ 
    
     Preparation Example 2 
     A granular composition was prepared by mixing uniformly and grinding the following ingredients, sufficiently kneading the mixture with a suitable amount of water, and granulating the kneaded mixture: 
     
         ______________________________________Compound No. 7     5 PartsMixture of bentonite              90 Partsand clayCalcium ligninsulfonate              5 Parts______________________________________ 
    
     Preparation Example 3 
     An emulsifiable concentrate was prepared by mixing uniformly the following ingredients: 
     
         ______________________________________Compound No. 31      50 PartsXylene               40 PartsMixture of polyoxyethylene                10 Partsnonylphenyl ether andcalcium alkylbenzenesulfonate______________________________________