N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition

Abstract

.DELTA.'-Tetrahydrophthalimides having a substituted oxy group at 3-position and, if necessary, a halogen atom at 4-position and/or at 2-position of phenyl group as N-substituent have excellent herbicidal activity and are useful as selective herbicides.

Description

BACKGROUND OF THE INVENTION

The present invention relates to novel N-substituted tetrahydrophthalimides and herbicidal compositions thereof.

N-substituted aryl-.DELTA.'-tetrahydrophthalimide derivatives having herbicidal activity have been reported.

For example, Japanese Examined Patent Publication No. 11940/1973 (U.S. Pat. No. 3,878,224 and U.S. Pat. No. 3,984,435 and West German Unexamined Patent Publication No. 2,165,651) discloses N-substituted-.DELTA.'-tetrahydrophthalimide which is represented by the general formula ##STR1## wherein R may be an aryl or aralkyl as phenyl optionally substituted with 1 to 5 halogen atoms; hydroxy, alkoxy, nitro, cyano, thiocyanno, carboxy, halogenated alkyl, alkyl, phenyl and OCH.sub.2 A (wherein A is phenyl or naphthyl) group and the like may also be substituted therein. N-(4-chloro-3-methoxyphenyl)-.DELTA.'-tetrahydrophthalimide and N-(4-bromo-3-methoxyphenyl)-.DELTA.'-tetrahydrophthalimide are described as the exemplified compounds having the formula wherein R is a halogen- and alkoxy-substituted phenyl group.

U.S. Pat. No. 4,001,272 and U.S. Pat. No. 4,032,326 disclose herbicidal 2-substituted aryl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones of the following formula: ##STR2## wherein X is Cl, Br or F and Y is H or F.

Degree of these compounds are highly affected by minor changes of a kind, a number or a position of substituents in the structure. Thus, it is difficult to predict herbicidal effects of novel compounds in view of similarity of chemical structures.

The inventors have studied novel tetrahydrophthalimides as an active ingredient of a herbicidal composition and have found that the specific novel N-aryl-3,4,5,6-tetrahydrophthalimides having H or a halogen atom at 2-position, a halogen atom at 4-position and a specific substituent at 5-position have excellent herbicidal effect.

SUMMARY OF THE INVENTION

The present invention is to provide novel N-substituted 3,4,5,6-tetrahydrophthalimides which are represented by the general formula ##STR3## wherein X and Y respectively represent hydrogen or a halogen atom; ##STR4## or --CN; R.sup.1 represents hydrogen atom or an alkyl, phenyl or a substituted phenyl group; R.sup.2 represents hydrogen atom or an alkyl group; R.sup.3 represents hydrogen atom or an alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkoxyalkoxyalkoxyalkyl, alkylthioalkyl, cycloalkyl, aralkyl, phenyl, .gamma.-butyrolactone group which can be substituted by methyl group or salt moiety; R.sup.4 represents an alkyl, alkoxycarbonylalkyl or benzyl group; R.sup.5 represents hydrogen atom or methyl group; R.sup.6 represents methyl or phenyl group; R.sup.7 and R.sup.8 can be the same or different and respectively represent hydrogen atom, an alkyl, alkenyl, alkynyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, substituted phenyl, heterocyclic ring, alkoxy, alkenyloxy, amino, mono-substituted amino, di-substituted amino, alkanesulfonyl, benzenesulfonyl, substituted benzenesulfonyl or cycloalkyl group or ##STR5## can form a heterocyclic ring which can have --O--; and m and n respectively represent an integer of 1 to 3.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The compounds having the formula (I) of the present invention are novel compounds. The typical compounds as herbicides can be the compounds having the formula (I) wherein X represents Cl, Br, I or H; preferably Cl, Br or H; Y represents H, F or Cl, preferably H or Cl (especially X is Cl, Br or H when Y is H; and X is Cl when Y is Cl); A represents ##STR6## R.sup.1 represents H or a C.sub.1-10 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl, preferably a C.sub.1-7 alkyl group such as methyl, ethyl n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, n-hexyl or n-heptyl group; R.sup.1 represents phenyl or substituted phenyl group such as chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl group, preferably substituted phenyl group such as chlorophenyl, bromophenyl, dichlorophenyl, and methylchlorophenyl group; R.sup.2 represents hydrogen atom or a C.sub.1-4 alkyl group such as methyl, ethyl propyl or butyl group preferably H or methyl group; n represents an integer of 1 to 3, preferably R.sup.1 and R.sup.2 are hydrogen atoms when n is an integer of 2 or 3.

When B is ##STR7## R.sup.3 represents H or a C.sub.1-12 straight or branched alkyl group preferably a C.sub.1-6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, 3-methylbutyl, 2,3-dimethylpropyl and n-hexyl group; a C.sub.2-5 alkenyl group such as vinyl, allyl, methallyl, 2-butenyl and 3-methyl-2-butenyl group preferably C.sub.3-4 alkenyl group; a C.sub.2-5 alkynyl group such as propargyl, butynyl, and 1,1-dimethylpropargyl group preferably C.sub.3-4 alkynyl group; a C.sub.1-5 haloalkyl group having one to four of chloro, bromo, iodo or fluoro groups preferably a C.sub.2-4 haloalkyl group having 1 to 4 halogen atoms such as fluoroethyl, chloroethyl, bromoethyl, dichloroethyl, dibromoethyl, trifluoroethyl, trichloroethyl, chloropropyl, bromopropyl, dichloropropyl, dibromopropyl, tetrafluoropropyl, chlorobutyl or bromobutyl; a C.sub.3-4 haloalkenyl group having 1 to 3 halogen atoms (Br, I, F, or Cl), preferably a C.sub.3 haloalkenyl group having 1 to 3 chlorine atoms such as chloroallyl, dichloroallyl or trichloroallyl group; a C.sub.2-4 cyanoalkyl such as cyanomethyl, cyanoethyl, or cyanopropyl group; a C.sub.2-4 hydroxyalkyl group such as hydroxyethyl, hydroxypropyl and hydroxybutyl group; alkoxyalkyl, alkoxyalkoxyalkyl or alkoxyalkoxyalkoxyalkyl group having 1 to 3 of C.sub.1-7 alkoxy groups and a C.sub.1-5 alkyl group preferably a C.sub.3-6 alkoxyalkyl group such as methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, ethoxypropyl and propoxypropyl group; a C.sub.5-8 alkoxyalkoxyalkyl group such as methoxyethoxyethyl, ethoxyethoxyethyl, propoxyethoxyethyl, butoxyethoxyethyl and methoxypropoxypropyl group; a C.sub.7-10 alkoxyalkoxyalkoxyalkyl group such as methoxyethoxyethoxyethyl, ethoxyethoxyethoxyethyl, propoxyethoxyethoxyethyl, butoxyethoxyethoxyethyl and methoxypropoxypropoxypropyl group; a C.sub.3-8 alkylthioalkyl group such as methylthioethyl, ethylthioethyl, propylthioethyl, butylthioethyl and pentylthioethyl group; a C.sub.4-8 cycloalkyl group preferably a C.sub.4-7 cycloalkyl group such as cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl group; a C.sub.7-9 aralkyl group such as benzyl, chlorobenzyl, bromobenzyl, methylbenzyl, .alpha.-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, phenethyl, methylphenethyl and phenylpropyl group; phenyl group; .gamma.-butyrolactone group which can be substituted by methyl group and R.sup.3 can be salt moiety such as alkali metals and alkaline earth metals such as Na, K and Ca; and ammonium groups having 0 to 4 alkyl groups having a total carbon atom content of 1 to 9 such as ammonium, methylammonium, ethylammonium, propylammonium, butylammonium, pentylammonium, hexylammonium, dimethylammonium, diethylammonium, dipropylammonium, dibutylammonium, trimethylammonium, triethylammonium, tripropylammonium, tetramethylammonium and tetraethylammonium group.

When B is ##STR8## R.sup.4 represents a C.sub.1-12 alkyl group preferably a C.sub.1-10 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, sec-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl group; a C.sub.3-6 alkoxycarbonylalkyl group such as methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl and butoxycarbonylmethyl group and benzyl group.

When B is ##STR9## R.sup.7 and R.sup.8 can be the same or different and respectively represent H or a C.sub.1-10 straight or branched alkyl group preferably a C.sub.1-7 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, n-hexyl and n-heptyl group; a C.sub.2-5 alkenyl group preferably a C.sub.3-4 alkenyl group such as allyl, methallyl and 2-butenyl group; a C.sub.2-5 alkynyl group such as propargyl, 2-butynyl and 1,1-dimethylpropargyl group, preferably C.sub.3-4 alkynyl group; a C.sub.2-6 haloalkyl group preferably a C.sub.2-4 haloalkyl group such as chloroethyl, chloropropyl and chlorobutyl group; a C.sub.2-6 hydroxyalkyl group preferably a C.sub.2-4 hydroxyalkyl group such as hydroxyethyl, hydroxypropyl and hydroxybutyl group; phenyl group; substituted phenyl group such as chlorophenyl, bromophenyl, methylphenyl and methoxyphenyl group especially phenyl, chlorophenyl, methylphenyl or methoxyphenyl group; a 5- or 6-membered heterocyclic ring group having at least one nitrogen atom such as pyridyl, pyrimidyl, triazinyl, thiazolyl, oxazolyl, diazolyl and triazolyl group; a C.sub.1-6 alkoxy group preferably a C.sub.1-4 alkoxy group such as methoxy, ethoxy, propoxy and butoxy group; a C.sub.2-4 alkenyloxy group such as vinyloxy, allyloxy, methallyloxy and 2-butenyloxy; amino group; mono-substituted amino group such as methylamino and phenylamino group; di-substituted amino group such as dimethylamino group; a C.sub.1-4 alkanesulfonyl group such as methanesulfonyl, ethanesulfonyl, propanesulfonyl and butanesulfonyl group; benzenesulfonyl group; substituted benzenesulfonyl group such as toluenesulfonyl, chlorobenzenesulfonyl and methoxybenzenesulfonyl group; and ##STR10## can form a heterocyclic ring group which can have --O-- as a 5- to 7-membered heterocyclic group such as pyrolidino, piperidino, morpholino, and hexahydroazepino group especially the 6-membered heterocyclic group such as piperidino or morpholino group. B can be ##STR11##

The compounds having the formula (I) can be various isomers such as optical isomers, diastereoisomers, and Z-E isomers. These isomers and mixtures are included in the definition of the present invention. These isomers are usually obtained in the form of a mixture thereof. In the examples, mixtures of the isomers are formed otherwise specified.

These isomers can be separated by various processes such as asymmetric synthesis, optical resolution and various chromatography such as column chromatography, thin layer chromatography and high speed liquid chromatography.

For example, the following compounds (I) are obtained in the form of isomers. ##STR12## The compounds (a) can be optical isomers when R.sup.1 is other than hydrogen atom or when D has asymmetric carbon atom in the case of R.sup.1 is H. ##STR13## The compounds (b) can be Z-E isomers. ##STR14##

The compounds (c) have two asymmetric carbon atoms to give diastereoisomers.

The compounds having the formula (I) can be produced by the following processes:

Process (1) ##STR15## wherein X, Y, A and B are the same as defined in the formula (I) and Z represents a halogen atom.

The reaction is carried out in a solvent such as acetone, ethyl methyl ketone, benzene, toluene, acetonitrile, tetrahydrofuran, and N,N-dimethylformamide in the presence of a base such as sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide or a fluoride such as potassium fluoride, cesium fluoride and tetra n-butyl ammonium fluoride in the presence or absence of an iodide such as sodium iodide and potassium iodide at 0.degree. to 150.degree. C.

Process (2) ##STR16##

The reaction of the tetrahydrophthalic anhydride with the aniline is carried out in the absence or presence of a solvent such as acetic acid, toluene, dioxane, methanol and water at 60.degree. to 200.degree. C.

Process (3)

The compounds having the formula (I) wherein B is ##STR17## can be produced by the following reaction. ##STR18## wherein D is OR.sup.3 (R.sup.3 is other than hydrogen atom), --SR.sup.4, ##STR19## preferably D is methoxy or ethoxy group. The compounds (I') can be produced by the process (1) or (2).

The hydrolysis can be carried out by the following conditions:

(i) in a solvent such as water, water-methanol, water-ethanol and dioxane in the presence of an acid such as hydrochloric acid and sulfuric acid at 0.degree. to 120.degree. C. or in a solvent such as formic acid and acetic acid in the presence of methanesulfonic acid and p-toluenesulfonic acid at 80.degree. to 180.degree. C.;

(ii) in a solvent such as N,N-dimethylformamide, N-methyl-2-pyrolidone, 2,4,6-collidine, 2,6-lutidine and pyridine, in the presence of lithium hydroxide, lithium bromide, lithium iodide and sodium iodide at 100.degree. to 200.degree. C.

(iii) in a solvent such as water, water-methanol, water-ethanol, water-dioxane and water-acetone in the presence of sodium hydroxide, potassium hydroxide and barium hydroxide at -20.degree. C. to 150.degree. C. After the reaction, the solvent is distilled off and the reaction is carried out in a solvent such as acetic acid, dilute hydrochloric acid and dilute hydrochloric acid-dioxane at 50.degree. to 200.degree. C.

Process (4)

When B has ##STR20## group in the formula (I), the compounds can be effectively produced by the following process. ##STR21## wherein D is --OR.sup.3, --SR.sup.4, ##STR22##

The reaction can be carried out in the absence of a solvent or in the presence of a solvent such as benzene, toluene, methyl chloride, chloroform, carbon tetrachloride, tetrahydrofuran, N,N-dimethylformamide, acetonitrile and pyridine in the presence of a reagent of thionyl chloride, phosphorous oxychloride, ethyl chlorocarbonate and N,N-dicyclohexylcarbodiimide in the presence or absence of a base such as triethylamine and N,N-diethylaniline at -20.degree. C. to 150.degree. C.

The carboxylic acid derivatives used as the starting material in the process are converted into intermediates such as acid chlorides, mixed acid anhydrides and acid anhydrides by the reaction of the reagent. The intermediates are converted into the object compounds by the reaction with a reagent such as alcohols, thiols and amines. The intermediates can be isolated in the process.

When A is ##STR23## group and B has ##STR24## group in the formula (I), the compounds can be effectively produced by the following process. ##STR25## wherein Z represents a halogen atom such as Cl, Br or I.

The reaction is carried out in a solvent such as acetone, ethyl methyl ketone, benzene, toluene, acetonitrile, tetrahydrofuran and N,N-dimethylformamide in the presence of a base such as sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide in the presence or absence of sodium iodide or potassium iodide at 0.degree. to 150.degree. C. The reaction may be performed through the following intermediate. ##STR26##

Process (6) ##STR27## wherein E represents OR.sup.3 and R.sup.3 is a salt moiety.

The reaction for production of the salt is carried out in a solvent such as water, water-methanol, water-ethanol, benzene, toluene and tetrahydrofuran at -20.degree. C. to 150.degree. C. The alkaline compounds used in the reaction can be an alkali or alkaline earth metal hydroxide such as sodium hydroxide, potassium hydroxide and calcium hydroxide; an alkali hydride such as sodium hydride and potassium hydride; an alkali metal such as metallic sodium and potassium, ammonia and mono-, di- or tri-alkylamine.

The processes for producing the compounds (I) of the present invention will be illustrated by certain examples which are provided for purposes of illustration only and are not intended to be limiting the present invention.

EXAMPLE 1

Production of N-[4-bromo-3-(1-ethoxycarbonylbutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 15.0 g. of N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 12.0 g. of ethyl .alpha.-bromovalerate, 7.7 g. of potassium carbonate, 2.5 g. of potassium iodide and 50 ml. of acetone was refluxed with stirring for 3 hours and then, the reaction mixture was cooled to room temperature and the salt was separated by a filtration. The filtrate was concentrated under a reduced pressure and 2N-HCl was added to the residue to crystallize the product. The crystal was separated by a filtration and washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate: n-hexane of 1:3) to obtain 17.6 g. of Compound No. 90 shown in table 1.

EXAMPLE 2

Production of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.88 g. of 1.52 g. of cyclohexane-1,2-dicarboxylic anhydride 2.88 g. of 4-bromo-3-(1-ethoxycarbonylethyloxy)aniline (n.sub.D.sup.25 =1.5590) and 10 ml. of acetic acid was refluxed with stirring for 2 hours and the reaction mixture was cooled to room temperature and water was added. The precipitate was separated by a filtration and was recrystallized from a mixture of benzene-cyclohexane to obtain 3.89 g. of Compound No. 18 shown in Table 1.

EXAMPLE 3

Production of N-[2,4-dichloro-5-(1-carboxyethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 14.4 g. of N-[2,4-dichloro-5-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 3.40 g. of methanesulfonic acid and 35 ml. of 86% formic acid was refluxed with stirring for 15 hours and the reaction mixture was cooled to room temperature and water was added and the product was extracted with ethyl acetate. The extract was concentrated under a reduced pressure and the oily product was admixed with n-hexane and was triturated to obtain the crystals. The product was recrystallized from benzene-cyclohexane to obtain 8.7 g. of Compound No. 11 shown in Table 1.

EXAMPLE 4

Production of N-[4-bromo-3-(1-carboxyethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 1 g. of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 5 g. of lithium iodide and 120 ml. of anhydrous N,N-dimethylformamide was heated with stirring in nitrogen gas flow at 140.degree. C. for 1.5 hours and the reaction mixture was cooled to room temperature and 2N-HCl was added and the product was extracted with ether. The extract was concentrated under a reduced pressure and the residue was recrystallized from a mixture of benzene-cyclohexane to obtain 0.72 g. of Compound No. 10 shown in Table 1.

EXAMPLE 5

Production of N-[4-bromo-3-(1-carboxyethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 4.7 g. of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 15 ml. of methanol and 4 ml. of 40% aqueous solution of sodium hydroxide was refluxed with stirring for 1 hour and the solvent was distilled off under a reduced pressure. The residue was mixed with 0.4 g. of cyclohexane-1,2-dicarboxylic anhydride and 20 ml. of glacial acetic acid and the mixture was refluxed with stirring for 3 hours and the reaction mixture was poured into 1 liter of water to precipitate the product. The precipitate was separated by a filtration and washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 8:1) to obtain 3.8 g. of Compound No. 10 shown in Table 1.

EXAMPLE 6

Production of N-(4-bromo-3-methoxycarbonylmethyloxy)phenyl-3,4,5,6-tetrahydrophthalimide

A mixture of 1.5 g. of N-(4-bromo-3-carboxymethyloxy)phenyl-3,4,5,6-tetrahydrophthalimide and 15 ml. of methanol was stirred at room temperature and HCl gas was bubbled for 0.5 hour and the solvent was distilled off and the residue was recrystallized from cyclohexane to obtain 1.5 g. of Compound No. 2 shown in Table 1.

EXAMPLE 7

Production of N-[4-bromo-3-(1-propylmercaptocarbonylpropyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.0 g. of N-[4-bromo-3-(1-carboxypropyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 2.5 ml. of thionyl chloride was refluxed for 1.5 hours and excess thionyl chloride was distilled off and the residue was dissolved in 10 ml. of toluene. The solution was admixed with a solution of 0.45 g. of 1-propanethiol and 0.60 g. of triethylamine in 5 ml. of toluene and the mixture was stirred at room temperature for 2 hours and then refluxed with stirring for 0.5 hour. The reaction mixture was cooled to room temperature and the precipitate was separated by a filtration and the filtrate was concentrated under a reduced pressure. The resulting oily product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:4) to obtain 2.26 g. of Compound No. 65 shown in Table 1.

EXAMPLE 8

Production of N-[4-bromo-3-(1-phenacyloxycarbonylbutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.11 g. of N-[4-bromo-3-(1-carboxybutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 11.19 g. of phenacyl bromide, 0.64 g. of potassium fluoride and 10 ml. of acetonitrile was refluxed with stirring for 8.5 hours and the reaction mixture was cooled and the precipitate was separated by a filtration. The filtrate was concentrated under a reduced pressure and the residue was purified by a chromatography on a column of silica gel (developing solvent of benzene) to obtain 2.20 g. of Compound No. 141 shown in Table 1.

EXAMPLE 9

Production of N-[4-bromo-3-(1-methoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A solution of 2.5 g. of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide in 30 ml. of methanol was prepared and HCl gas was bubbled at room temperature for 0.5 hour and then, the reaction mixture was kept for one night. The precipitate was separated by a filtration and washed with methanol to obtain 2.21 g. of Compound No. 16 shown in Table 1.

EXAMPLE 10

Production of N-[4-chloro-3-(1-ethoxycarbonylpropen-1-yloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 4.0 g. of N-(4-chloro-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 4.7 g. of ethyl 2,3-dibromobutyrate, 2.4 g. of potassium carbonate and 35 ml. of acetone was refluxed with stirring for 6 hours and the precipitated salt was separated by a filtration. The filtrate was concentrated under a reduced pressure and 2N-HCl was added to the residue to obtain a crude crystal. The product was washed with water and dried and purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 3:7) to obtain 5.2 g. of Compound No. 158 shown in Table 1.

EXAMPLE 11

Production of sodium salt of N-[4-bromo-3-(1-carboxybutyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

To a solution of 2.11 g. of N-[4-bromo-3-(1-carboxybutyloxy)phenyl]-3,4,5,6-tetrahyrophthalimide in 20 ml. of anhydrous benzene, 0.12 g. of sodium hydride was added. After generation of hydrogen was ceased, the solvent was distilled off to obtain 2.18 g. of Compound No. 84 shown in Table 1.

EXAMPLE 12

Production of diisopropylamine salt of N-[4-chloro-3-(1-carboxylpentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 1.18 g. of N-[4-chloro-3-(1-carboxypentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 0.33 g. of diisopropylamine and 8 ml. of benzene was heated at 80.degree. C. for 5 minutes and kept at room temperature for one night. The precipitate was separated by a filtration to obtain 1.15 g. of Compound No. 171 shown in Table 1.

EXAMPLE 13

Production of N-[4-bromo-3-cyanomethoxyphenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 1.0 g. of chloroacetonitrile, 2.2 g. of potassium iodide and 25 ml. of acetone was stirred at room temperature for 1 hour and then, 3.5 g. of N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide and 1.8 g. of potassium carbonate were added and the mixture was refluxed with stirring for 5 hours. The solvent was distilled off under a reduced pressure and 2N-HCl was added to the residue to precipitate the product. The precipitate was separated by a filtration and washed with water and dried and recrystallized from ethanol to obtain 2.7 g. of Compound No. 229 shown in Table 1.

Compounds Nos. 227,228 and 230 to 238 were respectively produced by the similar process.

EXAMPLE 14

Production of N-[4-chloro-3-cyanomethoxyphenyl]-3,4,5,6-tetrahydrophthalimide

A mixture of 1.52 g. of cyclohexane-1,2-dicarboxylic anhydride, 1.83 g. of 4-chloro-3-cyanomethoxyaniline (melting point 89.degree.-90.degree. C.) and 8 ml. of acetic acid was refluxed with stirring for 2.5 hours. The solvent was distilled off under a reduced pressure and then, water was added to obtain a crude crystal. The product was recrystallized from methanol to obtain 2.83 g. of Compound No. 228 shown in Table 1.

EXAMPLE 15

Production of N-[[4-chloro-3-[1-(propylcarbamoyl)propoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.00 g. of N-[4-chloro-3-(1-carboxypropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 5 ml. of thionyl chloride was refluxed with stirring for 1 hour and excess thionyl chloride was distilled off under a reduced pressure. The product was dissolved in 10 ml. of toluene and a mixture of 0.36 g. of n-propylamine, 0.6 g. of triethylamine and 5 ml. of toluene was added and the mixture was stirred at room temperature for 2 hours. Chloroform was added and the resulting organic phase was washed with water and dried and the product was purified by a chromatography on a column of silica gel (developing solvent:chloroform) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 1.62 g. of Compound No. 286 shown in Table 1.

Compounds Nos. 239, 244, 246, 248 to 256, 258, 262, 267, 271, 273, 275 to 277, 281, 283, 287 to 290. 292, 293, 295, 296, 298, 299, 301, 305 to 312, 317, 321, 324 to 326, 329 to 332 and 234 were respectively produced by the similar process.

EXAMPLE 16

Production of N-[[4-chloro-3-[1-(dimethylcarbamoyl)propoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.0 g. of N-[4-chloro-3-(1-carboxypropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 5 ml. of thionyl chloride was refluxed with stirring for 1 hour and excess thionyl chloride was distilled off under a reduced pressure. The residue was dissolved in 10 ml. of tetrahydrofuran and a mixture of 0.55 g. of 50% aqueous solution of dimethylamine, 0.6 g. of triethylamine and 5 ml. of tetrahydrofuran was added and the mixture was stirred at room temperature for 2 hours. Chloroform was added and the resulting organic phase was washed with water and dried and the residue was purified by a chromatography on a column of silica gel (developing solvent of chloroform) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 1.39 g. of Compound No. 297 shown in Table 1.

Compounds Nos. 263 to 265, 268, 270, 278, 300, 314, 327 and 328 were respectively produced by the similar process.

EXAMPLE 17

Production of N-[[4-chloro-3-[1-(dimethylcarbamoyl)butoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 2.20 g. of N-[4-chloro-3-(1-carboxybutoxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 5 ml. of thionyl chloride was refluxed with stirring for 1 hour and excess thionyl chloride was distilled off under a reduced pressure. The residue was dissolved in 10 ml. of tetrahydrofuran and a mixture of 1.3 g. of 50% aqueous solution of dimethylamine and 5 ml. of tetrahydrofuran was added and the resulting organic phase was washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent of chloroform) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 1.33 g. of Compound No. 313 shown in Table 1.

Compounds Nos. 241, 243, 269, 284, 285, 302, 304, 315, 316, 322 and 323 were respectively produced by the similar process.

EXAMPLE 18

Production of N-[[4-chloro-3-[1-(tosylcarbamoyl)pentyloxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 1.57 g. of N-[4-chloro-3-(1-carboxypentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide and 4 ml. of thionyl chloride was refluxed with stirring for 1 hour and excess thionyl chloride was distilled off under a reduced pressure. The residue was dissolved in 5 ml. of tetrahydrofuran and a mixture of 0.82 g. of p-toluenesulfonamide 0.23 g. of 50% sodium hydride and 10 ml. of tetrahydrofuran was added and the mixture was stirred at room temperature for 1 hour. Benzene was added and the resulting organic phase was washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent of chloroform) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 1.28 g. of Compound No. 335 shown in Table 1.

Compounds Nos. 279, 280 and 333 were respectively produced by the similar process.

EXAMPLE 19

Production of N-[[4-chloro-3-[1-(phenylcarbamoyl)propoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 1.52 g. of cyclohexane-1,2-dicarboxylic anhydride, 3.05 g. of N-phenyl-.alpha.-(5-amino-2-chlorophenoxy)butyramide (melting point of 78.degree. to 80.degree. C.) and 10 ml. of acetic acid was refluxed with stirring for 2 hours and the reaction mixture was cooled to room temperature and water was added to obtain a crude crystal. The product was recrystallized from a mixture of ethyl acetate and n-hexane to obtain 3.86 g. of Compound No. 294 shown in Table 1.

EXAMPLE 20

Production of N-[[4-chloro-3-[1-(ethylcarbamoyl)ethoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

(i) Production of ethyl .alpha.-(2-chloro-5-nitrophenoxy)propionate

A mixture of 17.4 g. of 2-chloro-5-nitrophenol, 19.0 g. of ethyl .alpha.-bromopropionate, 15.2 g. of potassium carbonate and 85 ml. of acetone was refluxed with stirring for 3.5 hours and the solvent was distilled off. 2N-HCl was added to the residue to obtain a crude crystal. The product was separated by a filtration and washed with water and dried and recrystallized from n-hexane to obtain 27.4 g. of the object compound (melting point of 46.degree. to 46.5.degree. C.).

(ii) Production of N-ethyl .alpha.-(2-chloro-5-nitrophenoxy)propionamide

A mixture of 2.74 g. of ethyl .alpha.-(2-chloro-5-nitrophenoxy)propionate, 0.77 g. of 70% aqueous solution of ethylamine and 15 ml. of ethanol was kept at room temperature for one night. The precipitate was separated by a filtration and recrystallized from a mixture of benzene-cyclohexane to obtain 2.5 g. of the object compound (melting point of 148.degree. to 149.degree. C.).

(iii) Production of N-[[4-chloro-3-[1-(ethylcarbamoyl)ethoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

In 15 ml. glacial acetic acid, 1.5 g. of N-ethyl-.alpha.-(2-chloro-5-nitrophenoxy)propionamide was reduced in the presence of a catalyst of 5% Pd/C. The catalyst was separated by a filtration. To the resulting N-ethyl-.alpha.-(5-amino-2-chlorophenoxy)propionamide, 0.83 g. of cyclohexane-1,2-dicarboxylic anhydride was added and the mixture was refluxed with stirring for 2 hours.

The reaction mixture was cooled to room temperature and water was added to obtain a crude crystal. The product was recrystallized from isopropanol to obtain 1.4 g. of Compound 242 shown in Table 1.

Compound No. 240 was produced by the similar process.

EXAMPLE 21

Production of N-[[4-bromo-3-[1-(diallylcarbamoyl)ethoxy]phenyl]]-3,4,5,6-tetrahydrophthalimide

A mixture of 8.5 g. of .alpha.-bromopropionyl chloride, 4.0 g. of sodium bicarbonate and 40 ml. of ether was cooled with ice and a solution of 4.0 g. of diallylamine in 10 ml. of ether was added dropwise and the mixture was stirred at room temperature for 1 hour.

The reaction mixture was washed with water and dried and the solvent was distilled off to obtain 3.8 g. of N,N-diallyl .alpha.-bromopropionamide. The product was admixed with 3.5 g. of N-(4-bromo-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 2.2 g. of potassium carbonate, 1.8 g. of potassium iodide and 50 ml. of acetone.

The mixture was refluxed with stirring for 3 hours. The resulting salt was separated by a filtration. The filtrate was distilled off under a reduced pressure. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:1) to obtain 2.8 g. of Compound No. 274 shown in Table 1.

Compounds Nos. 247 and 266 were respectively produced by the similar process.

The structures of all of the compounds shown in Table 1 were confirmed by IR spectrum and/or 'H-NMR spectrum.

TABLE 1__________________________________________________________________________ ##STR28##X Y OAB m.p. or n.sub.D__________________________________________________________________________1 Br H OCH.sub.2COOH mp 178-179.degree. C.2 Br H OCH.sub.2COOCH.sub.3 mp 140-143.degree. C.3 Cl Cl OCH.sub.2COOCH.sub.3 mp 141-142.degree. C.4 Cl H OCH.sub.2COOC.sub.2 H.sub.5 mp 105-107.degree. C.5 Br H OCH.sub.2COOC.sub.2 H.sub.5 mp 105-106.degree. C.6 Cl Cl OCH.sub.2COOC.sub.2 H.sub.5 mp 119.5-120.degree. C.7 Br H OCH.sub.2COOC.sub.3 H.sub.7n mp 83-84.degree. C.8 Br H OCH.sub.2COOCH.sub.2 CH.sub.2 OH mp 89-91.degree. C.9 Cl H ##STR29## mp 171-173.degree. C.10 Br H ##STR30## mp 189-191.degree. C.11 Cl Cl ##STR31## mp 155-156.degree. C.12 Br H ##STR32## amorphous solid13 Br H ##STR33## amorphous solid14 Br H ##STR34## amorphous solid15 Br H ##STR35## mp 157-162.degree. C.16 Br H ##STR36## mp 138-139.degree. C.17 Cl H ##STR37## mp 99-101.degree. C.18 Br H ##STR38## mp 109-110.degree. C.19 Cl Cl ##STR39## mp 121-122.degree. C.20 Cl H ##STR40## mp 64-66.degree. C.21 Br H ##STR41## mp 82-84.degree. C.22 Cl H ##STR42## mp 83.5-84.degree. C.23 Br H ##STR43## mp 91-92.degree. C.24 Cl H ##STR44## mp 114-114.5.degree. C.25 Br H ##STR45## mp 108-109.degree. C.26 Cl H ##STR46## mp 49.5-50.5.degree. C.27 Br H ##STR47## mp 67.5-68.5.degree. C.28 Br H ##STR48## mp 64-65.degree. C.29 Cl H ##STR49## n.sub.D.sup.15 1.547830 Cl H ##STR50## mp 103.5-104.5.degree. C.31 Br H ##STR51## mp 108-109.degree. C.32 Cl H ##STR52## mp 47.5-49.5.degree. C.33 Br H ##STR53## mp 58- 59.degree. C.34 Br H ##STR54## mp 83-84.5.degree. C.35 Cl H ##STR55## mp 57-58.degree. C.36 Cl H ##STR56## mp 42-43.degree. C.37 Br H ##STR57## mp 149-150.degree. C.38 Cl H ##STR58## mp 72-72.5.degree. C.39 Br H ##STR59## mp 51-53.degree. C.40 Cl H ##STR60## n.sub.D.sup.15 1.541041 Br H ##STR61## n.sub.D.sup.15 1.550342 Cl H ##STR62## n.sub.D.sup.15 1.540043 Br H ##STR63## n.sub.D.sup.14 1.549244 Br H ##STR64## n.sub.D.sup.25 1.539545 Cl H ##STR65## mp 93-93.5.degree. C.46 Cl H ##STR66## mp 92-93.degree. C.47 Br H ##STR67## mp 80-82.degree. C.48 Br H ##STR68## n.sub.D.sup.14 1.573849 Cl H ##STR69## mp 85-85.5.degree. C.50 Br H ##STR70## mp 117-119.degree. C.51 Br H ##STR71## mp 159-159.5.degree. C.52 Br H ##STR72## mp 159-160.degree. C.53 Br H ##STR73## mp 94-95.degree. C.54 Cl Cl ##STR74## mp 109-110.degree. C.55 Cl H ##STR75## mp 157-159.degree. C.56 Br H ##STR76## mp 173-174.degree. C.57 Br H ##STR77## mp 107-108.degree. C.58 Cl H ##STR78## mp 78-79.degree. C.59 Br H ##STR79## mp 58-60.degree. C.60 Cl H ##STR80## mp 70-73.degree. C.61 Br H ##STR81## mp 92-95.degree. C.62 Cl H ##STR82## mp 55-56.degree. C.63 Br H ##STR83## mp 63-64.degree. C.64 Cl H ##STR84## n.sub.D.sup.27 1.570365 Br H ##STR85## mp 65-66.degree. C.66 Cl H ##STR86## mp 50-51.degree. C.67 Br H ##STR87## mp 77.5-78.5.degree. C.68 Cl H ##STR88## n.sub.D.sup.22 1.561369 Cl H ##STR89## mp 49-50.degree. C.70 Br H ##STR90## mp 52-53.5.degree. C.71 Br H ##STR91## mp 55- 57.degree. C.72 Cl H ##STR92## n.sub.D.sup.24.5 1.522573 Br H ##STR93## mp 60-61.degree. C.74 Cl H ##STR94## n.sub.D.sup.25 1.541075 Br H ##STR95## n.sub.D.sup.25 1.533076 Cl H ##STR96## mp 47.5-48.5.degree. C.77 Br H ##STR97## mp 89-92.degree. C.78 Br H ##STR98## amorphous solid79 Cl H ##STR99## mp 95.5-97.degree. C.80 Br H ##STR100## mp 92-94.degree. C.81 Br H ##STR101## mp 157.5-158.degree. C.82 Cl H ##STR102## mp 134.5-136.degree. C.83 Br H ##STR103## mp 136-137.degree. C.84 Br H ##STR104## amorphous solid85 Br H ##STR105## amorphous solid86 Br H ##STR106## amorphous solid87 Cl H ##STR107## mp 72.5-74.5.degree. C.88 Br H ##STR108## mp 79-81.degree. C.89 Cl H ##STR109## mp 91.5-93.5.degree. C.90 Br H ##STR110## mp 104-105.degree. C.91 Cl H ##STR111## mp 67-70.degree. C.92 Br H ##STR112## mp 66-67.degree. C.93 Cl H ##STR113## mp 66-68.degree. C.94 Br H ##STR114## mp 81.5-83.degree. C.95 Cl H ##STR115## mp 79-83.degree. C.96 Br H ##STR116## mp 70-72.degree. C.97 Cl H ##STR117## mp 78-79.degree. C.98 Br H ##STR118## mp 79-80.degree. C.99 Cl H ##STR119## mp 46.5-48.degree. C.100 Br H ##STR120## mp 49.5-51.5.degree. C.101 Cl H ##STR121## n.sub.D.sup.26.5 1.5225102 Br H ##STR122## n.sub.D.sup.26.5 1.5171103 Cl H ##STR123## n.sub.D.sup.26.5 1.5231104 Br H ##STR124## n.sub.D.sup.26.5 1.5250105 Cl H ##STR125## n.sub.D.sup.22 1.5402106 Cl H ##STR126## mp 58-59.5.degree. C.107 Br H ##STR127## mp 52.5-55.5.degree. C.108 Cl H ##STR128## n.sub. D.sup.28 1.5485109 Br H ##STR129## n.sub.D.sup.28 1.5471110 Br H ##STR130## mp 66-68.degree. C.111 Cl H ##STR131## n.sub.D.sup.21 1.5502112 Br H ##STR132## n.sub.D.sup.21 1.5582113 Cl H ##STR133## mp 83-85.degree. C.114 Br H ##STR134## mp 65-67.degree. C.115 Cl H ##STR135## mp 66.5-69.degree. C.116 Br H ##STR136## mp 61.5-63.degree. C.117 Cl H ##STR137## mp 61.5-63.degree. C.118 Br H ##STR138## mp 70.5-72.degree. C.119 Cl H ##STR139## mp 75.5-76.5.degree. C.120 Br H ##STR140## mp 76-78.degree. C.121 Cl H ##STR141## mp 83.5-86.degree. C.122 Br H ##STR142## mp 83-86.degree. C.123 Cl H ##STR143## mp 69-72.degree. C.124 Br H ##STR144## mp 71-73.5.degree. C.125 Br H ##STR145## n.sub.D.sup.24.5 1.5220126 Br H ##STR146## n.sub.D.sup.25.5 1.5560127 Br H ##STR147## n.sub.D.sup.25 1.5435128 Br H ##STR148## n.sub.D.sup.25 1.5445129 Br H ##STR149## mp 91-92.degree. C.130 Br H ##STR150## mp 51-52.degree. C.131 Br H ##STR151## mp 94.5-95.5.degree. C.132 Cl H ##STR152## mp 104-107.degree. C.133 Br H ##STR153## mp 112-114.degree. C.134 Cl H ##STR154## mp 84-87.degree. C.135 Br H ##STR155## mp 89-92.degree. C.136 Cl H ##STR156## mp 105- 107.degree. C.137 Br H ##STR157## mp 97-99.degree. C.138 Br H ##STR158## amorphous solid139 Br H ##STR159## mp 101-102.5.degree. C.140 Br H ##STR160## n.sub.D.sup.24.5 1.5551141 Br H ##STR161## mp 130.5-131.degree. C.142 Br H ##STR162## n.sub.D.sup.22 1.5464143 Cl H ##STR163## mp 173-174.degree. C.144 Br H ##STR164## mp 188-190.degree. C.145 Br H ##STR165## mp 100-101.degree. C.146 Cl H ##STR166## mp 68-70.degree. C.147 Br H ##STR167## mp 69-71.5.degree. C.148 Cl H ##STR168## mp 67.5-69.degree. C.149 Br H ##STR169## mp 58-60 .degree. C.150 Cl H ##STR170## n.sub.D.sup.27 1.5359151 Br H ##STR171## n.sub.D.sup.27.5 1.5424152 Cl H ##STR172## n.sub.D.sup.27 1.5241153 Br H ##STR173## n.sub.D.sup.27.5 1.5423154 Cl H ##STR174## n.sub.D.sup.28 1.5248155 Br H ##STR175## n.sub.D.sup.28 1.5360156 Cl H ##STR176## n.sub.D.sup.25 1.5518157 Br H ##STR177## n.sub.D.sup.25 1.5583158 Cl H ##STR178## n.sub.D.sup.27 1.5653159 Br H ##STR179## mp 68-76.degree. C.160 Cl H OCH.sub.2 CH.sub.2CH.sub.2 COOH mp 154-157.degree. C.161 Br H OCH.sub.2 CH.sub.2 CH.sub.2 COOH mp 156-158.degree. C.162 Cl H OCH.sub.2 CH.sub.2 CH.sub.2COOC.sub.2 H.sub.5 mp 74-76.degree. C.163 Br H OCH.sub.2 CH.sub.2 CH.sub.2COOC.sub.2 H.sub.5 mp 79-80.degree. C.164 Cl Cl OCH.sub.2 CH.sub.2 CH.sub.2COOC.sub.2 H.sub.5 mp 94-95.degree. C.165 Br H OCH.sub.2 CHCHCOOH mp 145-148.degree. C.166 Cl H OCH.sub.2 CHCHCOOC.sub.2 H.sub.5 mp 110-111.degree. C.167 Br H OCH.sub.2 CHCHCOOC.sub.2 H.sub.5 mp 121-122.degree. C.168 Cl Cl OCH.sub.2 CHCHCOOC.sub.2 H.sub.5 mp 154-156.degree. C.169 Cl H ##STR180## mp 102-104.5.degree. C.170 Br H ##STR181## mp 106-110.degree. C.171 Cl H ##STR182## mp 147-151.degree. C.172 Cl H ##STR183## amorphous solid173 Cl H ##STR184## n.sub.D.sup.28 1.5479174 Br H ##STR185## n.sub.D.sup.28 1.5573175 Cl H ##STR186## mp 77-78.degree. C.176 Br H ##STR187## mp 97-98.degree. C.177 Br H ##STR188## n.sub.D.sup.22 1.5700178 Cl H ##STR189## mp 61.5-63.degree. C.179 Br H ##STR190## mp 79.5-82.degree. C.180 Cl H ##STR191## mp 55.5- 57.degree. C.181 Br H ##STR192## mp 63.5- 65.5.degree. C.182 Cl H ##STR193## n.sub.D.sup.28 1.5305183 Br H ##STR194## n.sub.D.sup.28 1.5398184 Cl H ##STR195## n.sub.D.sup.28 1.5285185 Br H ##STR196## n.sub.D.sup.28 1.5376186 Br H ##STR197## n.sub.D.sup.22 1.5590187 Br H ##STR198## mp 68.5-71.degree. C.188 Br H ##STR199## mp 75-76.degree. C.189 Cl H ##STR200## n.sub.D.sup.14 1.5305190 Br H ##STR201## n.sub.D.sup.14 1.5413191 Cl H ##STR202## mp 175.5-178.degree. C.192 Br H ##STR203## mp 174-176.degree. C.193 Br H ##STR204## mp 139-139.5.degree. C.194 Cl H ##STR205## mp 97-98.degree. C.195 Br H ##STR206## mp 116-119.degree. C.196 Cl H ##STR207## mp 100.5-103.degree. C.197 Br H ##STR208## mp 82-82.5.degree. C.198 Cl H ##STR209## amorphous solid 199 Cl H ##STR210## mp 106.5-107.5.degree. C.200 Br H ##STR211## mp 108-108.5.degree. C.201 Br H ##STR212## mp 98-98.5.degree. C.202 Br H ##STR213## mp 104.5-105.5.degree. C.203 Br H ##STR214## mp 93-94.degree. C.204 Br H ##STR215## n.sub.D.sup.25 1.5515205 Br H ##STR216## mp 105-106.degree. C.206 Cl H ##STR217## n.sub.D.sup.27 1.5823207 Br H ##STR218## mp 111.5-113.degree. C.208 Br H ##STR219## amorphous solid209 Cl H ##STR220## mp 112-114.degree. C.210 Cl H ##STR221## mp 127-129.degree. C.211 Cl H ##STR222## mp 116-117.degree. C.212 Br H ##STR223## mp 130-131.5.degree. C.213 Cl H ##STR224## mp 120-121.degree. C.214 Br H ##STR225## mp 140-151.degree. C.215 Br H ##STR226## mp 53-57.degree. C.216 Cl H OCH.sub.2COOH mp 174-175.degree. C.217 Cl H OCH.sub.2 COOC.sub.4 H.sub.9n mp 56-57.degree. C.218 Br H OCH.sub.2COOC.sub.4 H.sub.9n mp 51-53.degree. C.219 Cl H OCH.sub.2COOC.sub.5 H.sub.11n mp 68-69.degree. C.220 Cl H ##STR227## n.sub.D.sup.21 1.5516221 Br H ##STR228## amorphous solid222 H H OCH.sub.2COOC.sub.2 H.sub.5 mp 78-79.degree. C.223 H H ##STR229## mp 62-64.degree. C.224 H H ##STR230## mp 94-95.degree. C.225 H H ##STR231## mp 43-44.degree. C.226 H H OCH.sub.2 CH.sub.2 CH.sub.2COOC.sub.2 H.sub.5 mp 48-49.degree. C.227 H H OCH.sub.2 CN mp 135-136.degree. C.228 Cl H OCH.sub.2 CN mp 123-125.degree. C.229 Br H OCH.sub.2 CN mp 149-150.degree. C.230 Cl H ##STR232## mp 96-98.degree. C.231 Br H ##STR233## mp 120-121.degree. C.232 Cl Cl ##STR234## mp 141.5-142.degree. C.233 Br H ##STR235## mp 76-81.degree. C.234 Cl H OCH.sub.2 CH.sub.2 CH.sub.2 CN mp 89-90.degree. C.235 Cl H ##STR236## mp 79-80.degree. C.236 Br H ##STR237## mp 88-89.degree. C.237 Cl H ##STR238## n.sub.D.sup.25 1.5491238 Br H ##STR239## n.sub.D.sup.25 1.5598239 Cl H OCH.sub.2 CONHC.sub.3 H.sub.7n mp 225-230.degree. C.240 Cl H ##STR240## mp 163.5-164.5.degree. C.241 Br H ##STR241## mp 180-181.degree. C.242 Cl H ##STR242## mp 166-166.5.degree. C.243 Br H ##STR243## mp 159-161.degree. C.244 Cl H ##STR244## mp 116.5-117.degree. C.245 Br H ##STR245## mp 116-117.degree. C.246 Cl Cl ##STR246## mp 145-146.degree. C.247 Br H ##STR247## mp 118-120.degree. C.248 Br H ##STR248## mp 111-112.degree. C.249 Br H ##STR249## mp 112-113.degree. C.250 Br H ##STR250## mp 186.5-187.degree. C.251 Cl H ##STR251## mp 110-112.degree. C.252 Br H ##STR252## mp 105-106.degree. C.253 Cl H ##STR253## mp 120-121.degree. C.254 Br H ##STR254## mp 120.5-121.degree. C.255 Cl H ##STR255## mp 172-173.degree. C.256 Br H ##STR256## mp 167-168.5.degree. C.257 Br H ##STR257## mp 114-115.degree. C.258 Br H ##STR258## mp 178.5-179.5.degree. C.259 Br H ##STR259## mp 95-98.degree. C.260 Cl H ##STR260## mp 163-164.degree. C.261 Br H ##STR261## mp 187-188.degree. C.262 Cl Cl ##STR262## mp 126-127.degree. C.263 Cl H ##STR263## mp 162-162.5.degree. C.264 Cl H ##STR264## mp 145-145.5.degree. C.265 Cl H ##STR265## mp 138-139.5.degree. C.266 Br H ##STR266## mp 152-154.degree. C.267 Cl H ##STR267## mp 78-82.degree. C.268 Cl H ##STR268## mp 121.5-122.5.degree. C.269 Br H ##STR269## mp 135-136.degree. C.270 Cl Cl ##STR270## mp 116-117.degree. C.271 Br H ##STR271## mp 118-119.degree. C.272 Br H ##STR272## mp 88.5-89.5.degree. C.273 Br H ##STR273## n.sub.D.sup.25.5 1.5549274 Br H ##STR274## mp 99-100.degree. C.275 Br H ##STR275## mp 51-54.degree. C.276 Br H ##STR276## mp 129.5-130.degree. C.277 Br H ##STR277## mp 121-122.degree. C.278 Cl H ##STR278## mp 124-125.degree. C.279 Cl H ##STR279## mp 97.5-98.5.degree. C.280 Cl H ##STR280## mp 109-109.5.degree. C.281 Br H ##STR281## mp 131-132.degree. C.282 Br H ##STR282## mp 63-67.degree. C.283 Br H ##STR283## mp 108-110.degree. C.284 Cl H ##STR284## mp 202.5-204.degree. C.285 Br H ##STR285## mp 199-200.degree. C.286 Cl H ##STR286## mp 148.5-149.degree. C.287 Br H ##STR287## mp 143.5-144.5.degree. C.288 Br H ##STR288## mp 124-125.degree. C289 Br H ##STR289## mp 155.5-156.5.degree. C.290 Cl H ##STR290## mp 136.5-138.degree. C.291 Br H ##STR291## mp 127-128.5.degree. C.292 Cl H ##STR292## mp 122-130.degree. C. decomp.293 Br H ##STR293## mp 152-154.5.degree. C.294 Cl H ##STR294## mp 142-144.degree. C.295 Br H ##STR295## mp 148-149.degree. C.296 Br H ##STR296## mp 181-183.degree. C.297 Cl H ##STR297## mp 101-102.degree. C.298 Br H ##STR298## mp 113.5-114.5.degree. C.299 Cl H ##STR299## mp 97-98.degree. C.300 Cl H ##STR300## mp 130-130.5.degree. C.301 Br H ##STR301## mp 144-145.5.degree. C.302 Cl H ##STR302## mp 183.5-185.5.degree. C.303 Cl H ##STR303## mp 213.5-215.5.degree. C.304 Br H ##STR304## mp 218.5-219.5.degree. C.305 Br H ##STR305## mp 185-186.degree. C.306 Cl H ##STR306## mp 121.5-122.degree. C.307 Cl H ##STR307## mp 182.5-183.degree. C.308 Cl H ##STR308## mp 161-162.degree. C.309 Br H ##STR309## mp 160.5-161.degree. C.310 Cl H ##STR310## mp 156-158.degree. C.311 Cl H ##STR311## mp 135-136.5.degree. C.312 Br H ##STR312## mp 157-158.degree. C.313 Cl H ##STR313## mp 132-133.degree. C.314 Br H ##STR314## mp 92-93.degree. C.315 Cl H ##STR315## mp 186-187.degree. C.316 Br H ##STR316## mp 203-204.degree. C.317 Br H ##STR317## mp 124.5-125.5.degree. C.318 Cl H ##STR318## mp 115.5-116.5.degree. C.319 Br H ##STR319## mp 168-169.degree. C.320 Br H ##STR320## mp 165-166.degree. C.321 Br H ##STR321## amorphous solid322 Cl H ##STR322## mp 172-173.5.degree. C.323 Br H ##STR323## mp 157-158.degree. C.324 Cl H ##STR324## mp 172.5-174.degree. C.325 Br H ##STR325## mp 168-169.degree. C.326 Cl H ##STR326## mp 193.5-195.degree. C.327 Cl H ##STR327## mp 65-68.degree. C.328 Br H ##STR328## mp 186-188.degree. C.329 Br H ##STR329## mp 170.5-171.degree. C.330 Br H ##STR330## mp 186.5-187.degree. C.331 Br H ##STR331## mp 123.5-125.5.degree. C.332 Cl H ##STR332## mp 165-167.degree. C.333 Br H ##STR333## mp 167-168.degree. C.334 Br H ##STR334## mp 173.5-175.degree. C.335 Cl H ##STR335## mp 171-173.degree. C.336 Cl H ##STR336## mp 127.5-129.degree. C.337 Br H ##STR337## mp 121-122.5.degree. C.338 Cl H ##STR338## mp 87-88.degree. C.339 Br H ##STR339## mp 130-131.degree. C.340 Cl H ##STR340## mp 124-125.5.degree. C.341 Cl H ##STR341## mp 143-144.degree. C.342 Br H ##STR342## mp 128-129.5.degree. C.343 Cl H ##STR343## mp 92.5-93.5.degree. C.344 Br H ##STR344## mp 100-101.degree. C.345 Cl H ##STR345## mp 96.5-97.5.degree. C.346 Br H ##STR346## mp 88.5-89.degree. C.347 Cl H ##STR347## mp 144-145.degree. C.348 Br H ##STR348## mp 108-109.degree. C.349 Br H ##STR349## mp 130-131.degree. C.350 Cl H ##STR350## mp 136-137.degree. C.351 Cl H ##STR351## mp 112-113.5.degree. C.352 Cl H ##STR352## mp 73-75.degree. C.353 Br H ##STR353## mp 113.5-114.5.degree. C.354 Cl Cl ##STR354## mp 131-132.5.degree. C.355 Cl H ##STR355## mp 153.5-155.degree. C.356 Br H ##STR356## mp 152-153.5.degree. C.357 Cl H ##STR357## mp 104-105.degree. C.358 Cl H ##STR358## mp 138-139.degree. C.359 Cl H ##STR359## mp 92.5-93.degree. C.360 Cl H ##STR360## mp 108-110.degree. C.361 Br H ##STR361## mp 117.5-119.5.degree. C.362 Cl H ##STR362## mp 79.5-80.5.degree. C.363 Br H ##STR363## mp 100.5-101.5.degree. C.364 Cl H ##STR364## mp 135-136.degree. C.365 Cl H ##STR365## mp 84-85.degree. C.366 Br H ##STR366## mp 95-96.5.degree. C.367 Cl H ##STR367## mp 116-117.5.degree. C.368 Br H ##STR368## amorphous solid369 Cl H ##STR369## mp 104-105.degree. C.370 Br H ##STR370## mp 105.5-106.5.degree. C.371 Cl H ##STR371## mp 156-158.degree. C.372 Br H ##STR372## mp 158-160.degree. C.373 Cl H ##STR373## mp 125-127.degree. C.374 Cl H ##STR374## mp 142.5-144.degree. C.375 Br H ##STR375## mp 120.5-122.degree. C.376 Cl H ##STR376## mp 140-141.degree. C.377 Br H ##STR377## mp 109.5-110.degree. C.378 Cl H ##STR378## mp 123-124.degree. C.379 Br H ##STR379## mp 126.5-128.degree. C.380 Cl H ##STR380## mp 95-95.5.degree. C.381 Br H ##STR381## mp 102.5-103.5.degree. C.382 Cl H ##STR382## mp 101-102.degree. C.383 Br H ##STR383## mp 104.5-105.5.degree. C.384 Cl H ##STR384## mp 106-107.degree. C.385 Br H ##STR385## amorphous solid386 Cl H ##STR386## mp 94.5-95.5.degree. C.387 Cl Cl ##STR387## mp 107-108.degree. C.388 Br H ##STR388## mp 133-134.degree. C.389 Br H ##STR389## mp 126-127.degree. C.390 Cl H ##STR390## mp 83-84.5.degree. C.391 Cl H ##STR391## mp 85-86.degree. C.392 Cl H ##STR392## mp 94.5-95.degree. C.393 Cl H ##STR393## mp 99-100.degree. C.394 Cl H ##STR394## mp 95-96.degree. C.395 Cl H ##STR395## mp 101-102.degree. C.396 Cl H ##STR396## mp 112.5-113.degree. C.397 Cl H ##STR397## mp 81- 82.degree. C.398 Cl H ##STR398## amorphous solid399 Cl H ##STR399## mp 187.5-189.degree. C.400 Cl H ##STR400## mp 159-160.degree. C.401 Br H ##STR401## mp 130-131.degree. C.402 Cl Cl ##STR402## mp 149-150.degree. C.403 Cl H ##STR403## mp 156-158.degree. C.404 Cl H ##STR404## mp 122.5-124.degree. C.405 Br H ##STR405## mp 169-170.degree. C.406 Cl H ##STR406## mp 167-168.degree. C.407 Cl H ##STR407## mp 141-141.5.degree. C.408 Br H ##STR408## mp 138-139.degree. C.409 Cl Cl ##STR409## amorphous solid410 Cl H ##STR410## mp 127.5-128.5.degree. C.411 Br H ##STR411## mp 134.5-135.degree. C.412 Cl H ##STR412## n.sub.D.sup.25 1.5526413 Cl H ##STR413## mp 76-78.degree. C.414 Br H ##STR414## amorphous solid415 Cl H ##STR415## mp 104.5-106.degree. C.416 Cl Cl ##STR416## amorphous solid417 Cl H ##STR417## mp 92-93.5.degree. C.418 Br H ##STR418## mp 96-97.degree. C.419 Br H ##STR419## mp 108-109.5.degree. C.420 Br H ##STR420## mp 187.5-188.5.degree. C.421 Cl H ##STR421## mp 115-116.5.degree. C.422 Br H ##STR422## mp 151-152.5.degree. C.423 Cl H ##STR423## mp 141-142.degree. C.424 Br H ##STR424## mp 156-157.degree. C.425 Br H ##STR425## mp 155.5-156.5.degree. C.426 Br H ##STR426## mp 81-83.degree. C.427 Br H ##STR427## mp 99-100.degree. C.428 Br H ##STR428## mp 93.5-95.degree. C.429 Br H ##STR429## amorphous solid430 Cl H ##STR430## mp 101.5-102.degree. C.431 Br H ##STR431## mp 158-159.degree. C.432 Br H ##STR432## mp 157-159.degree. C.433 Br H ##STR433## mp 82-83.5.degree. C.434 Cl H ##STR434## mp 87.5-89.degree. C.__________________________________________________________________________

The following compounds are also included as the compounds (I) of the present invention; N-[4-chloro-3-(2-cyanoethoxy)phenyl]-3,4,5,6-tetrahydrophthalimide, N-[4-bromo-3-(2-cyanoethoxy)phenyl]-3,4,5,6-tetrahydrophthalimide, N-[4-chloro-3-(1-cyanopropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide, N-[4-bromo-3-(3-cyanopropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide, N-[4-chloro-3-(1-cyanopentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, and N-[4-bromo-3-(1-cyanopentyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide.

The following compounds are especially preferable as herbicides used in upland.

The compounds having the formula (I) wherein X is Cl; Y is H and A is ##STR435## and B is ##STR436## and (R.sup.7)' is H, methyl or methoxy group and (R.sup.8)' is a C.sub.1-4 alkyl, a C.sub.1-4 alkoxy, allyl or propargyl group.

The following compounds are also preferable as herbicides used in upland. The compounds having the formula (I) wherein X is Br; Y, A and B are defined above. The following compounds are also useful.

The compounds having the formula (I) wherein X is Cl; B is CN; and Y and B are defined above; or X is Br; B is CN and Y and B are defined above.

These compounds are Compounds Nos. 278, 290, 300, 355, 356, 360, 363, 377, 378, 382, 384, 393, 401, 408, 411, 230, 231, 233 and 235.

The following compounds are especially preferable as herbicides used in paddy field.

The compounds having the formula (I) wherein X is Br or Cl; Y is H; A is ##STR437## B is ##STR438## and (R.sup.3)' is a C.sub.1-4 alkyl group; or B is ##STR439## and (R.sup.4)' is a a C.sub.2-3 alkyl group; or B is ##STR440##

These compounds are Compounds Nos. 60, 61, 87, 90, 95, 96, 93, 94, 99, 100, 195, 259, 317, 349, 405 and 422.

The compounds (I) can be used as herbicides without an adjuvant. Thus, the compounds (I) are usually used in a form of herbicidal compositions such as an emulsifiable concentrate, a wettable powder, a dust, a granule and a tablet which can be prepared by admixing the active ingredient with a suitable inert liquid or solid carrier and another adjuvant such as suitable surfactants.

Suitable liquid carriers include toluene, xylene, methyl naphthalene, cyclohexane, butanol, glycol, dimethylsulfoxide, dimethylformamide, acetone, methyl isobutyl ketone, animal or vegetable oils, fatty acid, fatty acid esters and water.

Suitable solid carriers include clay, kaolin clay, talc, bentonite, diatomaceous earth, silica, calcium carbonate, soybean powder, wheat powder, other plant powder etc.

It is also possible to incorporate the other agricultural chemical such as agricultural fungicides, insecticides, nematocides, and the other herbicides, plant growth regulators, soil improvers and fertilizers.

It is also possible to incorporate a suitable adjuvant such as a spreader, an emulsifier, a wet spreader and a sticker for improving the herbicidal effect.

Suitable amounts of the active ingredient and the adjuvants in the herbicidal compositions of the present invention are as follows.

______________________________________ (% by weight) Active Other ingredient Surfactant Carrier additive______________________________________Wettable powder 5 to 80 2 to 20 10 to 93 0 to 5Flowable 5 to 60 5 to 30 10 to 90 0 to 20Granule 1 to 20 2 to 10 70 to 97 0 to 5Emulsifiable 5 to 80 5 to 30 10 to 90 0 to 5concentrate______________________________________

A dose of the compound (I) as the herbicide is depending upon a kind of the compound, a kind of weed, a season and method of the application and a kind of soil and is usually in a range of 2 to 80 g./are.

The compounds (I) as the herbicide of the present invention can be applied in flooded soil treatment at preemergence or in treatments at growth period, and impart excellent herbicidal activity to annual weeds and perennial weeds and have low phytotoxicity to transplanted rice seedling which are remarkably preferable as herbicide in paddy field. In the soil treatment at preemergence and the foliage and soil treatment in upland, the compounds of the present invention impart excellent herbicidal activity to annual weeds and perennial weeds and high residual effect. The phytotoxicity to crop plants is remarkably low, even though it is applied at high concentration.

The compounds as a herbicide of the present invention are used for controlling the following weeds.

______________________________________Scientific name (American name)______________________________________Dicotyledonous weeds:Ipomoea spp. (morningglories)Galium aparine (bedstraw)Stellaria media (common chickweed)Galinsoga ciliata (hairy galinsoga)Chenopodium album var. controrubrumChenopodium album (lambsquarters)Abutilon theophrasti (velvetleaf)Brassica kaber var. pinnatifida (wild mustard)Capsella bursa-pastoris (shepherdspurse)Rumex japonicusPolygonum persicaria (ladysthumb)Portulaca aleracea (common purslane)Amaranthus lividus (livid amaranth)Ambrosia artemisifolia (common ragweed)Rotala indica (toothcup)Lindernia procumbensEclipta prostrataBidens tripartitaDopatrium junceumElatine triandraPolygonum thunbergiiMonocotyledonous weeds:Echinochloa crus-galli (barnyard grass)Digitaria sanguinalis (large crabgrass)Eleusine indica (goosegrass)Setaria viridis (green foxtail)Poa annua (annual bluegrass)Alopecurus aequalis (water foxtail)Cynodon dactylon (bermudagrass)Agropyron repens (quackgrass)Cyperus microiriaCyperus difformisEleocharis kuroguwai (water chestnut)Eleocharis acicularis (slender spikerush)Scirpus juncoides (hardstem bulrush)Cyperus serotinusScirpus maritimusMonochoria vaginalisSagitaria pygmaeaAlisma canaliculatumSagitaria trifolia______________________________________

The compounds as a herbicide of the present invention can be used as selective herbicides in the cultivation of the following crops.

______________________________________Dicotyledonous crops:Glycine max (soybean)Gossypium indicum (cotton)Beta vulgaris (sugar beet)Helianthus annuus (sunflower)Pisum sativum (pea)Solanum tuberosum (potato)Cucumis sativus (cucumber)Monocotyledonous crops:Oryza sativa (rice)Triticum aestivum (wheat)Hordoum vulgare (barley)Avena fatua (oat)Secale cereale (rye)Zea mays (corn)Saccharum officinarum (sugar cane)______________________________________

The application of the compounds as a herbicide of the present invention is not only to the aforementioned plants but also to the other plants by the same manner.

The herbicides and herbicidal compositions of the present invention will be further illustrated by certain examples for preparations and herbicidal experimental tests which are provided for purposes of illustration only and are not intended to be limiting the present invention.

In the preparations and the experiments, the term "part" means "parts by weight" and Compound numbers correspond to Compounds shown in Table 1. As references, the following compounds are also used.

Reference A: N-(3-methoxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide Reference B: N-(3-methoxy-4-bromophenyl)-3,4,5,6-tetrahydrophthalimide Reference C: 2,4,6-trichlorophenyl-4'-nitrophenyl ether Reference D: S-(2-chlorobenzyl)-N,N-diethylthiol-carbamate Reference E: 3-(3,4-dichlorophenyl)-1,1-dimethylurea Reference F: 2,4-dichlorophenyl-4'-nitrophenyl ether Reference G: 3,4-dichloropropionic anilide

Wettable powder

Compound shown in Table 1--50 parts Carplex #80 (Shionogi Seiyaku K.K.)--15 parts N,N-kaolin clay (Tsuchiya Kaolin K.K.)--30 parts Sorpol 8070 (Toho Kagaku K.K.) (higher alkyl sulfate surfactant)--5 parts

The components were uniformly mixed and ground to obtain a wettable powder containing 50% of the active ingredient.

Granule

Compound shown in Table 1--5 parts Clay (Nippon Talc K.K.)--38 parts Bentonite (Hojunyoko K.K.)--55 parts Aerol CT-1 (Toho Kagaku K.K.) (succinate type surfactant)--2 parts

The components were mixed with water and kneaded and granulated by a granulating machine and dried at 60.degree. C. for 2 hours to obtain a granule containing 5% of the active ingredient.

Emulsifiable concentrate

Compound shown in Table 1--30 parts Xylene--30 parts Dimethylformamide--25 parts

The compound was dissolved into the mixed solvent and then, 15 parts of polyoxyethylene type surfactant (Sorpol 3005X: Toho Kagaku K.K.) was admixed to obtain an emulsifiable concentrate containing 30% of the active ingredient.

In the tests, the following weeds were used and the weeds are shown by the following symbols.

Barnyardgrass (Echinochloa crus-galli): B.G. Tooth cup (Rotala indica): T.C. Narrowleaf waterplantain (Alisma canaliculatum): N.W. Hardstem bulrush (Scirpus juncoides): H.B. Crabgrass (Digitaria songuinalis (L.) Scop): C.G. Ladys thumb (Polygonum persicaria): L.T. Lambsguarter (Chenopoduim album L.): L.A. Sawa millet (Echinochloa frumentacea): S.M.

Test A

(i) Flooded paddy field test for preemergence of paddy weeds

Each pot of 1/2500 are filled with paddy diluvium soil and manured (fertilizer application) and seeds of Barnyardgrass, Tooth cup, Hardstem bulrush, and Narrowleaf waterplantain were sown. The seeds were mixed well in the upper layer having a thickness of 2 cm and the pot was flooded in a depth of about 3 cm. Next day, each wettable powder containing each of Compounds of the present invention and Reference Compounds as the active ingredient was diluted with water and the diluted solution was applied so as to give each dose (40, 20, 10 or 5 g./are) of the active ingredient by a drop treatment under the flooded surface.

For three days after the treatment, a leaching loss of water was given at a rate of 3 cm/day and the pot was kept in a greenhouse.

Twenty one days after the treatment, survival quantities of the plants were measured to find herbicidal effects to weeds. The results are shown in Table 2. Herbicidal effects are rated by the following equation and ratings. ##EQU1##

______________________________________Herbicidaleffect rating Y (%)______________________________________0 0-51 5-302 30-503 50-704 70-905 90-100______________________________________

In tables, "Dose" means "dose of active ingredient" (g/are).

Test B

In accordance with the experiment of Test A, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 3.

Test C

In accordance with the experiment of Test A, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 4.

TABLE 2______________________________________ Dose of active ingredient Herbicidal EffectCompound No. (g/a) B.G. T.C. N.W. H.B.______________________________________1 40 5 5 5 5 20 5 5 5 5 10 4 5 5 52 40 5 5 5 5 20 4 5 5 5 10 4 5 5 53 40 5 5 5 5 20 4 5 5 5 10 4 5 4 44 40 5 5 5 5 20 5 5 5 5 10 4 5 5 55 40 5 5 5 5 20 5 5 5 5 10 5 5 5 46 40 5 5 5 5 20 4 5 5 5 10 4 5 4 47 40 5 5 5 5 20 5 5 5 5 10 3 5 5 48 40 4 5 5 5 20 4 5 5 5 10 4 5 5 49 40 5 5 5 5 20 4 5 5 5 10 4 5 5 410 40 5 5 5 5 20 4 5 5 5 10 4 5 5 311 40 5 5 5 5 20 4 5 5 4 10 4 5 5 312 40 5 5 5 5 20 5 5 5 4 10 4 5 5 413 40 5 5 5 5 20 5 5 5 5 10 4 5 4 414 40 5 5 5 5 20 5 5 5 5 10 4 5 5 415 40 5 5 5 5 20 5 5 5 5 10 5 5 5 516 20 5 5 5 5 10 5 5 5 5 5 5 5 5 517 20 5 5 5 5 10 5 5 5 5 5 5 5 5 418 20 5 5 5 5 10 5 5 5 5 5 5 5 5 519 20 5 5 5 5 10 5 5 5 5 5 4 5 5 520 20 5 5 5 5 10 5 5 5 5 5 4 5 5 521 20 5 5 5 5 10 5 5 5 5 5 5 5 5 522 20 5 5 5 5 10 5 5 5 5 5 5 5 5 523 20 5 5 5 5 10 5 5 5 5 5 5 5 5 524 20 5 5 5 5 10 5 5 5 5 5 5 5 5 525 20 5 5 5 5 10 5 5 5 5 5 5 5 5 526 40 5 5 5 5 20 5 5 5 5 10 5 5 5 527 20 5 5 5 5 10 5 5 5 5 5 5 5 5 528 40 5 5 5 5 20 5 5 5 5 10 4 5 5 529 40 5 5 5 5 20 5 5 5 5 10 5 5 5 530 40 5 5 5 5 20 5 5 5 5 10 5 5 5 531 40 5 5 5 5 20 5 5 5 5 10 3 5 5 432 40 5 5 5 5 20 5 5 5 5 10 5 5 5 533 40 5 5 5 5 20 5 5 5 5 10 5 5 5 534 40 5 5 5 5 20 5 5 5 4 10 5 5 5 435 40 5 5 5 5 20 5 5 5 5 10 5 5 5 536 40 5 5 5 5 20 4 5 5 5 10 3 5 4 337 40 5 5 5 5 20 5 5 5 5 10 5 5 5 438 40 5 5 5 5 20 5 5 5 4 10 5 5 5 439 40 5 5 5 5 20 5 5 5 5 10 5 5 5 440 20 5 5 5 5 10 5 5 5 5 5 5 5 5 541 40 5 5 5 5 20 5 5 5 5 10 4 5 5 442 40 5 5 5 5 20 5 5 5 5 10 4 5 5 443 40 5 5 5 5 20 5 5 5 4 10 4 5 5 544 20 5 5 5 5 10 5 5 5 5 5 5 5 5 545 20 5 5 5 5 10 5 5 5 5 5 5 5 5 546 20 5 5 5 5 10 5 5 5 5 5 5 5 5 547 40 5 5 5 5 20 5 5 5 5 10 5 5 5 448 20 5 5 5 5 10 5 5 5 4 5 5 5 5 449 40 5 5 5 5 20 5 5 5 4 10 3 5 4 350 40 5 5 5 5 20 5 5 5 5 10 5 5 5 351 40 5 5 5 4 20 4 5 5 4 10 4 5 4 352 40 4 5 5 5 20 4 5 5 5 10 3 5 5 353 20 5 5 5 5 10 5 5 5 5 5 5 5 5 554 40 5 5 5 5 20 5 5 5 5 10 5 5 5 455 40 5 5 5 5 20 4 5 5 5 10 4 5 5 356 40 5 5 5 5 20 4 5 5 5 10 3 5 5 357 20 5 5 5 5 10 5 5 5 5 5 5 5 5 558 20 5 5 5 5 10 5 5 5 5 5 5 5 5 559 20 5 5 5 5 10 5 5 5 5 5 5 5 5 560 20 5 5 5 5 10 5 5 5 5 5 5 5 5 461 20 5 5 5 5 10 5 5 5 5 5 5 5 5 562 20 5 5 5 5 10 5 5 5 5 5 5 5 5 563 40 5 5 5 5 20 5 5 5 5 10 5 5 5 364 40 5 5 5 5 20 5 5 5 5 10 5 5 5 464 40 5 5 5 5 20 5 5 5 4 10 4 5 4 366 40 5 5 5 5 20 5 5 5 4 10 4 5 5 467 40 5 5 5 5 20 5 5 5 5 10 5 5 5 368 40 5 5 5 5 20 5 5 5 5 10 5 5 5 569 40 5 5 5 5 20 5 5 5 4 10 5 5 5 470 40 5 5 5 5 20 5 5 5 5 10 4 5 5 471 40 5 5 5 5 20 5 5 5 4 10 5 5 5 372 40 5 5 5 5 20 4 5 5 4 10 3 5 4 373 40 5 5 5 4 20 5 5 5 5 10 5 5 5 474 40 5 5 5 5 20 5 5 5 5 10 5 5 5 475 40 5 5 5 5 20 5 5 5 5 10 5 5 5 476 40 5 5 5 4 20 5 5 5 4 10 3 5 5 477 40 5 5 5 4 20 5 5 5 4 10 4 5 5 478 40 5 5 5 4 20 4 5 5 4 10 4 5 4 379 40 5 5 5 5 20 5 5 5 4 10 5 5 5 480 40 5 5 5 5 20 5 5 5 5 10 4 5 5 381 40 5 5 5 5 20 4 5 5 4 10 4 5 4 382 40 5 5 5 5 20 5 5 5 5 10 5 5 5 483 40 5 5 5 5 20 4 5 5 5 10 3 5 5 384 40 5 5 5 5 20 5 5 5 5 10 4 5 5 485 40 5 5 5 5 20 5 5 5 5 10 5 5 5 486 40 5 5 5 5 20 5 5 5 5 10 4 5 5 587 20 5 5 5 5 10 5 5 5 5 5 5 5 5 588 20 5 5 5 5 10 5 5 5 5 5 5 5 5 589 20 5 5 5 5 10 5 5 5 5 5 5 5 5 590 20 5 5 5 5 10 5 5 5 5 5 5 5 5 591 20 5 5 5 5 10 5 5 5 5 5 5 5 5 592 20 5 5 5 5 10 5 5 5 5 5 5 5 5 593 20 5 5 5 5 10 5 5 5 5 5 5 5 5 594 20 5 5 5 5 10 5 5 5 5 5 5 5 5 595 40 5 5 5 5 20 4 5 5 4 10 4 5 4 396 40 5 5 5 4 20 4 5 5 4 10 3 5 5 397 40 5 5 5 5 20 5 5 5 5 10 5 5 5 498 40 5 5 5 5 20 5 5 5 4 10 4 5 5 599 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5100 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5150 40 5 5 5 5 20 5 5 5 4 10 4 5 5 4151 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3152 40 5 5 5 5 20 5 5 5 5 10 3 5 5 4153 40 5 5 5 5 20 4 5 5 5 10 4 5 4 3154 40 4 5 5 5 20 4 5 5 5 10 4 5 5 4155 40 4 5 5 5 20 4 5 5 4 10 3 5 5 4156 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4157 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4158 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4159 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4160 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4161 40 5 5 5 5 20 4 5 5 5 10 3 5 5 3162 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5163 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5164 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4165 40 5 5 5 5 20 4 5 5 4 10 4 5 5 4166 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4167 40 5 5 5 5 20 5 5 5 5 10 5 5 5 3168 40 5 5 5 5 20 4 5 5 4 10 4 4 4 3169 40 5 5 5 5 20 4 5 5 5 10 4 5 4 3170 40 5 5 5 5 20 4 5 5 4 10 3 5 5 4171 40 5 5 5 5 20 5 5 5 4 10 4 5 5 4172 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4173 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5174 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5175 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5176 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5177 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4178 40 5 5 5 5 20 5 5 5 5 10 4 5 5 4179 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4180 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3181 40 5 5 5 5 20 4 5 5 4 10 4 5 5 3182 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4183 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4184 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3185 40 5 5 5 5 20 5 5 5 4 10 4 5 5 3186 40 5 5 5 5 20 4 5 5 4 10 3 5 4 3187 40 5 5 5 5 20 5 5 5 5 10 5 5 5 3188 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4189 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4190 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5191 40 5 5 5 5 20 5 5 5 4 10 3 4 5 3192 40 5 5 5 4 20 4 5 5 4 10 4 5 4 3193 40 5 5 5 5 20 4 5 5 4 10 3 5 4 3194 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5195 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4196 40 5 5 5 5 20 4 5 5 5 10 3 5 5 4197 40 5 5 5 5 20 4 5 5 4 10 4 5 4 3198 40 5 5 5 5 20 4 5 5 4 10 3 5 4 3199 40 4 5 5 5 20 4 5 5 4 10 4 5 5 3200 40 5 5 5 5 20 4 5 5 4 10 3 5 5 4Reference A 40 5 5 5 5 20 4 4 4 4 10 3 3 4 2Reference B 40 5 5 5 5 20 3 5 4 3 10 3 3 3 3Reference C 20 5 5 2 4 10 4 4 1 2 5 2 3 0 0Reference D 40 5 4 2 5 20 4 3 0 4 10 1 2 0 2Non-treatment 0 0 0 0 0______________________________________ TABLE 3______________________________________ Dose of active ingredient Herbicidal EffectCompound No. (g/a) B.G. T.C. N.W. H.B.______________________________________227 40 5 5 5 5 20 4 5 5 5 10 4 5 5 4228 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5229 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5230 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5231 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5232 40 5 5 5 5 20 5 5 5 5 10 4 5 5 4233 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4234 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5235 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5236 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4237 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5238 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5Reference A 40 5 5 5 5 20 4 4 5 4 10 3 4 3 3Reference B 40 5 5 5 5 20 4 5 4 4 10 3 4 3 2Reference C 20 5 5 3 3 10 4 5 1 0 5 2 4 0 0Reference D 40 5 4 2 5 20 4 4 0 4 10 1 2 0 3Non-treatment -- 0 0 0 0______________________________________ TABLE 4______________________________________ Dose of active ingredient Herbicidal EffectCompound No. (g/a) B.G. T.C. N.W. H.B.______________________________________239 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4240 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5241 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5242 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5243 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4244 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5245 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4246 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4247 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4248 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4249 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4250 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4251 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5252 40 5 5 5 5 20 5 5 5 4 10 4 5 5 4253 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4254 20 5 5 5 5 10 5 5 5 4 5 5 5 5 4255 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4256 40 5 5 5 5 20 5 5 5 5 10 4 5 5 4257 20 5 5 5 5 10 5 5 5 4 5 4 5 5 4258 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4259 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5260 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3261 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3262 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5263 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5264 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4265 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5266 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5267 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4268 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5269 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5270 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4271 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4272 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5273 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5274 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5275 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4276 40 5 5 5 5 20 5 5 5 5 10 5 5 5 5277 40 5 5 5 5 20 5 5 5 5 10 4 5 5 4278 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5279 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5280 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4281 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5282 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4283 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4284 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4285 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5286 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4287 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4288 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5289 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4290 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5291 40 5 5 5 5 20 5 5 5 4 10 4 5 5 4292 40 5 5 5 5 20 5 5 5 5 10 4 5 5 3293 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4294 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5295 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4296 40 5 5 5 5 20 4 5 5 5 10 4 5 5 3297 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5298 40 5 5 5 5 20 5 5 5 5 10 5 5 5 4299 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4300 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5301 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5302 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4303 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4304 40 5 5 5 5 20 5 5 5 5 10 4 5 5 4305 40 5 5 5 5 20 4 5 5 5 10 4 5 5 4306 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4307 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4308 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5309 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5310 40 5 5 5 5 20 5 5 5 4 10 5 5 5 4311 40 5 5 5 5 20 4 5 5 4 10 4 5 5 4312 40 5 5 5 5 20 5 5 5 4 10 4 5 5 4313 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4336 20 5 5 5 5 10 4 5 5 4 5 4 5 5 4337 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5338 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4339 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5340 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5341 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5342 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4343 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5344 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5345 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5346 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5347 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5348 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5349 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5350 20 5 5 5 5 10 4 5 5 4 5 4 5 4 3351 20 5 5 5 4 10 5 5 5 4 5 3 5 4 3352 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4353 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5354 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5355 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5356 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5357 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5358 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5359 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5360 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5361 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4362 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5363 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5364 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4365 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4366 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5367 20 5 5 5 5 10 5 5 5 5 5 5 5 5 3368 20 5 5 5 5 10 5 5 5 5 5 5 5 5 3369 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5370 20 5 5 5 5 10 5 5 5 5 5 4 5 5 5371 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5372 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5373 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4374 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4375 20 5 5 5 5 10 5 5 5 5 5 4 5 5 3376 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4377 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5378 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5379 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4380 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5381 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5382 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5383 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5384 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5385 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4386 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4387 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5388 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5389 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5390 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5391 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5392 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4393 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5394 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5395 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5396 20 5 5 5 5 10 5 5 5 4 5 5 5 5 4397 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4398 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5399 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5400 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5401 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5402 20 5 5 5 5 10 5 5 5 5 5 4 5 5 4403 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5404 20 5 5 5 5 10 5 5 5 5 5 5 5 5 4405 20 5 5 5 5 10 4 5 5 5 5 4 5 4 3406 20 5 5 5 5 10 5 5 5 5 5 4 5 4 4407 20 5 5 5 5 10 5 5 5 5 5 5 5 5 3408 20 5 5 5 5 10 5 5 5 5 5 5 5 5 5Reference A 40 5 5 5 5 20 4 4 5 4 10 3 3 3 2Reference B 40 5 5 5 5 20 4 5 4 4 10 2 3 3 2Reference C 20 5 5 3 4 10 4 5 1 2 5 2 3 0 0Reference D 40 5 4 2 5 20 4 3 0 4 10 1 2 0 3Non-treatment -- 0 0 0 0______________________________________

Test D

Phytotoxicity test for rice seedlings

Each Wagner pot of 1/5,000 was filled with paddy diluvium soil and manured (fertilizer application) and puddled with suitable water and two rice seedlings of 2.6 leaf stage (Sasanishiki, height of 14.3 cm: good seedling) were transplanted in a depth of about 2 cm, and the pot was flooded in a depth of 1.5 cm.

One or seven days after the transplantation, each granule containing each of Compounds of the present invention and Reference Compound was fallen on the flooded surface at each dose (40, 20 or 10 g/are) of the compound.

For three days after the treatment, a leaching loss of water was given at a rate of 3 cm/day and the pot was kept in greenhouse.

Twenty one days after the treatment, phytotoxicities of the compounds to rice seedlings were observed. The results are shown in Table 5.

The phytotoxicities were rated as follows. ##EQU2##

______________________________________Rating ofphytotoxicity Y(%)______________________________________0 0-51 5-102 10-203 20-404 40-605 60-100______________________________________

Test E

In accordance with the experiment of Test D, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 6.

Test F

In accordance with the experiment of Test D, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 7.

TABLE 5______________________________________ Dose of active Phytotoxicity to rice seedling ingredient one day after 7 days afterCompound No. (g/a) transplantation transplantion______________________________________1 40 1 0 20 0 0 10 0 02 40 0 0 20 0 0 10 0 03 40 0 0 20 0 0 10 0 04 40 2 0 20 0 0 10 0 05 40 2 1 20 0 0 10 0 06 40 0 0 20 0 0 10 0 07 40 1 0 20 0 0 10 0 08 40 0 0 20 0 0 10 0 09 40 0 0 20 0 0 10 0 010 40 0 0 20 0 0 10 0 011 40 1 0 20 0 0 10 0 012 40 1 0 20 0 0 10 0 013 40 0 0 20 0 0 10 0 014 40 1 0 20 0 0 10 0 015 40 2 0 20 0 0 10 0 016 40 1 0 20 0 0 10 0 017 40 1 1 20 0 0 10 0 018 40 1 0 20 0 0 10 0 019 40 0 0 20 0 0 10 0 020 40 1 0 20 0 0 10 0 021 40 1 1 20 0 0 10 0 022 40 2 0 20 0 0 10 0 023 40 0 0 20 0 0 10 0 024 40 0 0 20 0 0 10 0 025 40 1 0 20 0 0 10 0 026 40 1 0 20 0 0 10 0 027 40 1 0 20 0 0 10 0 028 40 1 0 20 0 0 10 0 029 40 1 0 20 0 0 10 0 030 40 1 0 20 0 0 10 0 031 40 0 0 20 0 0 10 0 032 40 1 1 20 0 0 10 0 033 40 0 0 20 0 0 10 0 034 40 0 0 20 0 0 10 0 035 40 2 0 20 0 0 10 0 036 40 0 0 20 0 0 10 0 037 40 1 0 20 0 0 10 0 038 40 0 0 20 0 0 10 0 039 40 0 0 20 0 0 10 0 040 40 1 0 20 0 0 10 0 041 40 0 0 20 0 0 10 0 042 40 0 0 20 0 0 10 0 043 40 0 0 20 0 0 10 0 044 40 1 1 20 0 0 10 0 045 40 1 0 20 0 0 10 0 046 40 1 0 20 0 0 10 0 047 40 0 0 20 0 0 10 0 048 40 0 0 20 0 0 10 0 049 40 0 0 20 0 0 10 0 050 40 1 0 20 0 0 10 0 0151 40 0 0 20 0 0 10 0 0152 40 0 0 20 0 0 10 0 0153 40 1 1 20 0 0 10 0 0154 40 1 0 20 0 0 10 0 0155 40 0 0 20 0 0 10 0 0156 40 0 0 20 0 0 10 0 0157 40 0 0 20 0 0 10 0 0158 40 0 0 20 0 0 10 0 0159 40 1 0 20 0 0 10 0 0160 40 0 0 20 0 0 10 0 0161 40 0 0 20 0 0 10 0 0162 40 1 0 20 0 0 10 0 0163 40 0 0 20 0 0 10 0 0164 40 1 0 20 0 0 10 0 0165 40 0 0 20 0 0 10 0 0166 40 1 0 20 0 0 10 0 0167 40 0 0 20 0 0 10 0 0168 40 0 0 20 0 0 10 0 0169 40 0 0 20 0 0 10 0 0170 40 0 0 20 0 0 10 0 0171 40 0 0 20 0 0 10 0 0172 40 1 0 20 0 0 10 0 0173 40 0 0 20 0 0 10 0 0174 40 1 0 20 0 0 10 0 0175 40 2 0 20 0 0 10 0 0176 40 1 1 20 0 0 10 0 0177 40 1 0 20 0 0 10 0 0178 40 0 0 20 0 0 10 0 0179 40 1 0 20 0 0 10 0 0180 40 0 0 20 0 0 10 0 0181 40 0 0 20 0 0 10 0 0182 40 0 0 20 0 0 10 0 0183 40 1 0 20 0 0 10 0 0184 40 0 0 20 0 0 10 0 0185 40 0 0 20 0 0 10 0 0186 40 0 0 20 0 0 10 0 0187 40 1 0 20 0 0 10 0 0188 40 1 1 20 0 0 10 0 0189 40 1 0 20 0 0 10 0 0190 40 1 0 20 0 0 10 0 0191 40 0 0 20 0 0 10 0 0192 40 0 0 20 0 0 10 0 0193 40 0 0 20 0 0 10 0 0194 40 1 0 20 0 0 10 0 0195 40 1 0 20 0 0 10 0 0196 40 0 0 20 0 0 10 0 0197 40 0 0 20 0 0 10 0 0198 40 0 0 20 0 0 10 0 0199 40 0 0 20 0 0 10 0 0200 40 0 0 20 0 0 10 0 0201 40 0 0 20 0 0 10 0 0202 40 0 0 20 0 0 10 0 0203 40 1 0 20 0 0 10 0 0204 40 0 0 20 0 0 10 0 0205 40 1 0 20 0 0 10 0 0206 40 0 0 20 0 0 10 0 0207 40 0 0 20 0 0 10 0 0208 40 0 0 20 0 0 10 0 0209 40 0 0 20 0 0 10 0 0210 40 0 0 20 0 0 10 0 0211 40 0 0 20 0 0 10 0 0212 40 1 0 20 0 0 10 0 0213 40 0 0 20 0 0 10 0 0214 40 0 0 20 0 0 10 0 0215 40 0 0 20 0 0 10 0 0Reference A 40 2 2 20 1 0 10 0 0Reference B 40 2 1 20 1 1 10 0 0Reference C 40 3 2 20 2 0 10 0 0Reference D 40 4 2 20 2 1 10 0 0Non- 40 0 0Treatment 20 10______________________________________ TABLE 6______________________________________ Dose of active Phytotoxicity to rice seedling ingredeient one day after 7 days afterCompound No. (g/a) transplantation transplantation______________________________________227 40 0 0 20 0 0 10 0 0228 40 1 1 20 0 0 10 0 0229 40 1 0 20 0 0 10 0 0230 40 2 0 20 0 0 10 0 0231 40 1 0 20 0 0 10 0 0232 40 1 0 20 0 0 10 0 0233 40 0 0 20 0 0 10 0 0234 40 1 0 20 0 0 10 0 0235 40 0 0 20 0 0 10 0 0236 40 1 0 20 0 0 10 0 0237 40 1 0 20 0 0 10 0 0238 40 0 0 20 0 0 10 0 0Reference A 40 2 2 20 1 0 10 0 0Reference B 40 2 1 20 0 0 10 0 0Reference C 20 3 2 10 2 0 5 0 0Reference D 40 4 2 20 2 0 10 0 0Non-treatment -- 0 0______________________________________ TABLE 7______________________________________ Dose of active Phytotoxicity to rice seedling ingredient one day after 7 days afterCompound No. (g/a) transplantation transplantation______________________________________239 40 1 0 20 0 0 10 0 0240 40 1 1 20 0 0 10 0 0241 40 2 1 20 0 0 10 0 0242 40 1 0 20 0 0 10 0 0243 40 0 0 20 0 0 10 0 0244 40 1 0 20 0 0 10 0 0245 40 0 0 20 0 0 10 0 0246 40 0 0 20 0 0 10 0 0247 40 1 0 20 0 0 10 0 0248 40 0 0 20 0 0 10 0 0249 40 0 0 20 0 0 10 0 0250 40 0 0 20 0 0 10 0 0251 40 1 0 20 0 0 10 0 0252 40 0 0 20 0 0 10 0 0253 40 1 0 20 0 0 10 0 0254 40 0 0 20 0 0 10 0 0255 40 0 0 20 0 0 10 0 0256 40 0 0 20 0 0 10 0 0257 40 0 0 20 0 0 10 0 0258 40 1 0 20 0 0 10 0 0259 40 1 1 20 0 0 10 0 0260 40 0 0 20 0 0 10 0 0261 40 0 0 20 0 0 10 0 0262 40 2 0 20 0 0 10 0 0263 40 1 0 20 0 0 10 0 0264 40 0 0 20 0 0 10 0 0265 40 1 0 20 0 0 10 0 0266 40 1 0 20 0 0 10 0 0267 40 1 0 20 0 0 10 0 0268 40 0 0 20 0 0 10 0 0267 40 1 0 20 0 0 10 0 0270 40 1 0 20 0 0 10 0 0271 40 0 0 20 0 0 10 0 0272 40 1 0 20 0 0 10 0 0273 40 2 1 20 0 0 10 0 0274 40 1 0 20 0 0 10 0 0275 40 0 0 20 0 0 10 0 0276 40 0 0 20 0 0 10 0 0277 40 0 0 20 0 0 10 0 0278 40 1 0 20 0 0 10 0 0279 40 1 1 20 0 0 10 0 0280 40 0 0 20 0 0 10 0 0281 40 0 0 20 0 0 10 0 0282 40 0 0 20 0 0 10 0 0283 40 0 0 20 0 0 10 0 0284 40 0 0 20 0 0 10 0 0285 40 1 0 20 0 0 10 0 0286 40 0 0 20 0 0 10 0 0287 40 0 0 20 0 0 10 0 0288 40 1 1 20 0 0 10 0 0313 40 0 0 20 0 0 10 0 0314 40 1 0 20 0 0 10 0 0315 40 0 0 20 0 0 10 0 0316 40 0 0 20 0 0 10 0 0317 40 1 0 20 0 0 10 0 0318 40 0 0 20 0 0 10 0 0319 40 0 0 20 0 0 10 0 0320 40 1 0 20 0 0 10 0 0321 40 0 0 20 0 0 10 0 0322 40 0 0 20 0 0 10 0 0323 40 1 1 20 0 0 10 0 0324 40 0 0 20 0 0 10 0 0325 40 0 0 20 0 0 10 0 0326 40 1 0 20 0 0 10 0 0327 40 1 1 20 0 0 10 0 0328 40 0 0 20 0 0 10 0 0329 40 0 0 20 0 0 10 0 0330 40 0 0 20 0 0 10 0 0331 40 1 0 20 0 0 10 0 0332 40 0 0 20 0 0 10 0 0333 40 0 0 20 0 0 10 0 0334 40 1 0 20 0 0 10 0 0335 40 0 0 20 0 0 10 0 0336 40 0 0 20 0 0 10 0 0337 40 0 0 20 0 0 10 0 0338 40 1 0 20 0 0 10 0 0339 40 0 0 20 0 0 10 0 0340 40 0 0 20 0 0 10 0 0341 40 1 0 20 1 0 10 0 0342 40 1 0 20 0 0 10 0 0343 40 1 1 20 0 0 10 0 0344 40 2 0 20 0 0 10 0 0345 40 1 1 20 0 0 10 0 0346 40 2 1 20 0 0 10 0 0347 40 1 1 20 1 0 10 0 0348 40 1 1 20 0 0 10 0 0349 40 1 0 20 0 0 10 0 0350 40 1 0 20 0 0 10 0 0351 40 0 0 20 0 0 10 0 0352 40 0 0 20 0 0 10 0 0353 40 1 0 20 0 0 10 0 0354 40 1 0 20 1 0 10 0 0355 40 1 0 20 0 0 10 0 0356 40 0 0 20 0 0 10 0 0357 40 1 0 20 0 0 10 0 0358 40 1 1 20 0 0 10 0 0359 40 1 0 20 0 0 10 0 0360 40 2 0 20 0 0 10 0 0361 40 1 0 20 0 0 10 0 0362 40 1 0 20 0 0 10 0 0363 40 1 0 20 0 0 10 0 0364 40 1 0 20 0 0 10 0 0365 40 2 1 20 0 0 10 0 0366 40 1 1 20 0 0 10 0 0367 40 0 0 20 0 0 10 0 0368 40 1 0 20 0 0 10 0 0369 40 1 1 20 0 0 10 0 0370 40 1 0 20 0 0 10 0 0371 40 0 0 20 0 0 10 0 0372 40 0 0 20 0 0 10 0 0373 40 1 0 20 0 0 10 0 0374 40 0 0 20 0 0 10 0 0375 40 1 0 20 0 0 10 0 0376 40 1 0 20 0 0 10 0 0377 40 2 1 20 0 0 10 0 0Reference A 40 2 1 20 1 1 10 0 0Reference B 40 1 1 20 1 0 10 0 0Reference C 40 3 2 20 2 1 10 0 0Reference D 40 4 2 20 2 1 10 0 0Non-treatment -- 0 0______________________________________

Test G

Up-land soil treatment test

Each plastic pot of 1/2,500 are was filled with black volcano ash soil and manured and seeds of wheat, corn, soybean, and cotton were sown and were covered with the soil in a depth of 2 to 3 cm and seeds of weeds of Large crabgrass, Ladys thumb and Lambsquarter were mixed in the covered soil layer. Each wettable powder containing each of Compounds of the present invention and Reference Compound was diluted with water and the solution was sprayed uniformly on the surface of the soil at a dose (40, 20 or 10 g/are) of the compound by a small size power pressurized spray.

Twenty days after the treatment, herbicidal effects were observed and phytotoxicities to the crop plants were also observed. The results are shown in Table 8.

The herbicidal effects are rated as those of Test A and the phytotoxicities to crop plants are rated as those of Test C.

Test H

In accordance with the experiment of Test G, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 9.

Test I

In accordance with the experiment of Test G, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 10.

TABLE 8______________________________________Doseof Phytotoxicity to crop plantsComp. Comp. Herbicidal effect Soy-No. (g/a) C.G. L.T. L.A. Wheat Corn bean Cotton______________________________________25 40 5 5 5 0 0 0 0 20 5 4 5 0 0 0 0 10 4 4 5 0 0 0 026 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 3 4 0 0 0 027 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 028 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 4 0 0 0 029 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 4 0 0 0 030 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 4 5 0 0 0 031 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 032 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 033 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 034 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 035 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 036 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 4 0 0 0 037 40 5 5 5 0 0 0 0 20 5 4 5 0 0 0 0 10 4 4 5 0 0 0 038 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 039 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 040 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 041 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 042 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 5 0 0 0 043 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 5 0 0 0 044 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 045 40 5 4 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 5 0 0 0 046 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 047 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 4 0 0 0 048 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 049 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 050 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 051 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 3 4 0 0 0 052 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 5 0 0 0 053 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 054 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 055 40 5 4 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 056 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 3 5 0 0 0 057 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 5 0 0 0 058 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 059 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 060 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 5 5 0 0 0 061 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 3 5 0 0 0 062 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 063 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 064 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 065 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 3 4 0 0 0 066 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 067 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 3 5 0 0 0 068 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 069 40 5 5 5 0 0 0 0 20 3 5 5 0 0 0 0 10 3 4 5 0 0 0 070 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 071 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 072 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 073 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 074 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 3 5 0 0 0 075 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 076 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 0105 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 0106 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0107 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0108 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 0109 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0110 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 0111 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0112 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 0113 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0114 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0115 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 5 0 0 0 0116 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0117 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0118 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0119 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 5 0 0 0 0120 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 3 5 0 0 0 0121 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 4 0 0 0 0122 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0123 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0124 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0125 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 0Ref. A 40 5 5 5 2 0 0 1 20 4 4 5 0 0 0 0 10 3 4 4 0 0 0 0Ref. B 40 5 5 5 2 0 0 0 20 4 4 5 0 0 0 0 10 2 4 4 0 0 0 0Ref. E 40 5 5 5 4 3 1 2 20 5 5 5 2 1 0 2 10 3 3 4 0 0 0 0Ref. F 40 5 5 5 3 2 1 2 20 4 4 4 1 0 0 0 10 2 2 3 0 0 0 0Non- 0 0 0 0 0 0 0treat-ment______________________________________ TABLE 9______________________________________Doseof Phytotoxicity to crop plantsComp. Comp. Herbicidal effect Soy-No. (g/a) C.G. L.T. L.A. Wheat Corn bean Cotton______________________________________228 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0229 40 5 5 5 2 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0230 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0231 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0232 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0233 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0234 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0235 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0236 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0Ref. A 40 5 5 5 2 0 0 0 20 4 4 5 0 0 0 0 10 3 3 4 0 0 0 0Ref. B 40 5 5 5 1 0 0 1 20 4 4 4 0 0 0 0 10 3 4 4 0 0 0 0Ref. E 40 5 5 5 4 2 1 2 20 5 5 5 2 1 0 1 10 3 4 4 0 0 0 0Ref. F 40 5 5 5 3 1 2 1 20 4 4 4 1 0 0 0 10 2 3 3 0 0 0 0Non- -- 0 0 0 0 0 0 0treat-ment______________________________________ TABLE 10______________________________________Doseof Phytotoxicity to crop plantsComp. Comp. Herbicidal effect Soy-No. (g/a) C.G. L.T. L.A. Wheat Corn bean Cotton______________________________________258 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 0259 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0260 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 0261 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 3 5 0 0 0 0262 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0263 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 4 5 0 0 0 0264 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0265 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0266 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0267 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0268 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0269 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0270 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0271 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0272 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0273 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0274 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0275 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0276 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0277 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 5 0 0 0 0278 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0279 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0280 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0281 40 5 5 5 2 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0282 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0283 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0284 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0285 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0286 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0287 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0288 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0289 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0290 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0291 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0292 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 5 0 0 0 0293 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0294 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0295 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0296 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 5 0 0 0 0297 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0298 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0299 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0300 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0301 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0302 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0303 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0304 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0305 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0306 40 5 5 5 1 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0307 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0308 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0309 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0310 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0311 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0312 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0313 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0338 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0339 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 5 0 0 0 0340 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 5 0 0 0 0341 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0342 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0343 40 5 5 5 1 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0344 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0345 40 5 5 5 1 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0346 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0347 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 4 5 0 0 0 0348 40 5 5 5 1 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0349 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0350 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0351 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 4 5 0 0 0 0352 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0353 40 5 5 5 1 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0354 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0355 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0356 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 0357 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0358 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0359 40 5 5 5 0 0 1 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0360 40 5 5 5 1 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0361 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0362 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0363 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0364 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0365 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0366 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0367 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 5 0 0 0 0368 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 3 4 5 0 0 0 0369 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0370 40 5 5 5 1 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0371 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 3 5 0 0 0 0372 40 5 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 4 4 5 0 0 0 0373 40 5 5 5 0 0 0 0 20 5 4 5 0 0 0 0 10 3 4 5 0 0 0 0374 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0375 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0376 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 4 5 0 0 0 0377 40 5 5 5 1 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0378 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0388 40 4 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 3 5 4 0 0 0 0389 40 5 5 5 1 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0390 40 5 5 5 1 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0391 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0392 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0393 40 5 5 5 1 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0394 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0395 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0396 40 5 5 5 0 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0397 40 5 5 5 0 0 1 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0398 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0399 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0400 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0401 40 5 5 5 1 0 1 0 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0402 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 4 5 0 0 0 0403 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0404 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 4 5 0 0 0 0405 40 4 5 5 0 0 0 0 20 4 4 5 0 0 0 0 10 3 4 5 0 0 0 0406 40 5 5 5 0 0 0 0 20 4 5 5 0 0 0 0 10 4 5 5 0 0 0 0407 40 5 5 5 0 0 0 0 20 5 5 5 0 0 0 0 10 4 5 5 0 0 0 0409 40 5 5 5 0 0 0 1 20 5 5 5 0 0 0 0 10 5 5 5 0 0 0 0Ref. A 40 5 5 5 2 0 0 1 20 4 4 4 1 0 0 0 10 2 3 4 0 0 0 0Ref. B 40 5 5 5 2 0 0 0 20 4 4 5 0 0 0 0 10 3 2 4 0 0 0 0Ref. E 40 5 5 5 4 3 1 2 20 5 5 5 3 1 0 1 10 3 4 3 0 0 0 0Ref. F 40 5 5 5 3 1 1 1 20 4 4 4 1 0 1 0 10 2 2 4 0 0 0 0Non- -- 0 0 0 0 0 0 0treat-ment______________________________________

Test J

Foliage treatment test

Each polyethylene pot was filled with black volcano ash soil and manured and seeds of Sawa millet, Large Crabgrass and Radish were respectively sown in each pot. The pot was kept in a greenhouse. When Sawa millet and Large crabgrass were grown to 2 leaf stage and Radish to 1 leaf stage, each solution prepared by diluting each emulsifiable concentrate containing each of Compounds of the present invention and Reference Compounds, at a concentration of 0.5, 0.25 or 0.125%, was sprayed at a rate of 10 liter per are by a small power pressurized sprayer and the pot in the greenhouse was observed.

Fifteen days after the treatment, herbicidal effects were observed. The results are shown in Table 11.

The herbicidal effects are rated as those of Test A.

Test K

In accordance with the experiment of Test J, each herbicidal effect of each of Compounds of the present invention and Reference Compounds was tested. The results are shown in Table 12.

Test L

In accordance with the experiment of Test J, each test was carried out by using the compounds shown in Table 1. The results are shown in Table 13.

TABLE 11______________________________________Compound Concentration Herbicidal effectNo. % S.M. C.G. Radish______________________________________1 0.5 4 5 5 0.25 4 5 5 0.125 3 3 52 0.5 4 5 5 0.25 4 4 5 0.125 3 3 53 0.5 5 5 5 0.25 4 5 5 0.125 4 4 54 0.5 4 5 5 0.25 4 4 5 0.125 3 3 55 0.5 5 5 5 0.25 5 5 5 0.125 4 4 56 0.5 4 5 5 0.25 4 4 5 0.125 4 3 37 0.5 4 5 5 0.25 4 4 5 0.125 3 3 48 0.5 4 5 5 0.25 4 4 5 0.125 4 4 59 0.5 5 5 5 0.25 5 5 5 0.125 5 5 510 0.5 5 5 5 0.25 4 5 5 0.125 4 4 511 0.5 5 5 5 0.25 5 5 5 0.125 4 5 512 0.5 5 5 5 0.25 5 5 5 0.125 5 5 513 0.5 5 5 5 0.25 5 5 5 0.125 5 5 514 0.5 5 5 5 0.25 5 5 5 0.125 5 5 515 0.5 5 5 5 0.25 5 5 5 0.125 5 5 516 0.5 5 5 5 0.25 4 5 5 0.125 4 5 517 0.5 5 5 5 0.25 5 5 5 0.125 5 5 518 0.5 5 5 5 0.25 5 5 5 0.125 4 5 519 0.5 4 5 5 0.25 4 4 5 0.125 3 3 520 0.5 5 5 5 0.25 4 5 5 0.125 4 4 521 0.5 4 5 5 0.25 4 4 5 0.125 4 4 522 0.5 5 5 5 0.25 5 5 5 0.125 5 5 523 0.5 5 5 5 0.25 4 5 5 0.125 4 4 524 0.5 5 5 5 0.25 4 4 5 0.125 3 4 425 0.5 5 5 5 0.25 4 5 5 0.125 4 4 526 0.5 5 5 5 0.25 5 5 5 0.125 5 5 527 0.5 5 5 5 0.25 5 5 4 0.125 4 5 428 0.5 5 5 5 0.25 4 5 5 0.125 3 4 529 0.5 5 5 5 0.25 5 5 5 0.125 5 5 530 0.5 4 5 5 0.25 4 5 5 0.125 3 4 531 0.5 4 5 5 0.25 4 5 5 0.125 4 4 532 0.5 5 5 5 0.25 5 5 5 0.125 4 5 533 0.5 5 5 5 0.25 5 5 4 0.125 4 5 434 0.5 4 5 5 0.25 4 4 4 0.125 4 4 435 0.5 5 5 5 0.25 5 5 5 0.125 5 5 536 0.5 5 5 5 0.25 4 4 5 0.125 3 4 437 0.5 5 5 5 0.25 4 5 5 0.125 4 4 438 0.5 5 5 5 0.25 5 5 5 0.125 5 5 539 0.5 5 5 5 0.25 5 5 5 0.125 4 5 440 0.5 5 5 5 0.25 5 5 5 0.125 5 5 541 0.5 5 5 5 0.25 5 5 5 0.125 5 5 542 0.5 5 5 5 0.25 5 5 5 0.125 5 5 543 0.5 5 5 5 0.25 5 5 5 0.125 5 5 544 0.5 5 5 5 0.25 5 5 5 0.125 5 5 545 0.5 5 5 5 0.25 4 5 5 0.125 4 4 446 0.5 5 5 5 0.25 4 5 5 0.125 4 4 447 0.5 4 5 5 0.25 4 5 5 0.125 3 4 548 0.5 5 5 5 0.25 5 5 5 0.125 4 5 549 0.5 5 5 5 0.25 4 5 4 0.125 4 4 450 0.5 5 5 5 0.25 4 5 4 0.125 3 4 490 0.5 5 5 5 0.25 4 5 5 0.125 4 4 491 0.5 4 5 5 0.25 4 5 5 0.125 3 4 592 0.5 5 5 5 0.25 4 5 5 0.125 3 4 493 0.5 4 5 5 0.25 4 5 5 0.125 3 4 494 0.5 4 5 5 0.25 4 4 4 0.125 4 4 495 0.5 4 5 5 0.25 4 4 5 0.125 3 3 496 0.5 4 5 5 0.25 4 4 5 0.125 4 4 497 0.5 5 5 5 0.25 4 4 5 0.125 3 4 498 0.5 4 5 5 0.25 4 4 5 0.125 4 4 499 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5100 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5101 0.5 5 5 5 0.25 4 5 5 0.125 4 5 5102 0.5 5 5 5 0.25 4 5 5 0.125 4 4 4103 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5104 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5105 0.5 4 5 5 0.25 4 4 5 0.125 3 3 5106 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5107 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5108 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5109 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5110 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5111 0.5 4 5 5 0.25 4 4 5 0.125 4 4 5112 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5113 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5114 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5115 0.5 4 5 5 0.25 4 5 5 0.125 3 4 5116 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5117 0.5 5 5 5 0.25 4 5 5 0.125 3 3 5118 0.5 4 5 5 0.25 4 4 5 0.125 4 4 5119 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5120 0.5 4 5 5 0.25 4 4 5 0.125 4 4 5190 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5191 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5192 0.5 5 5 5 0.25 5 5 4 0.125 5 5 4193 0.5 5 5 5 0.25 4 5 5 0.125 4 4 4194 0.5 5 5 5 0.25 5 5 4 0.125 4 4 4195 0.5 4 5 5 0.25 4 4 4 0.125 4 4 4196 0.5 4 5 5 0.25 4 4 4 0.125 4 4 4197 0.5 5 5 5 0.25 4 4 5 0.125 3 4 4198 0.5 5 5 5 0.25 4 5 5 0.125 3 3 4199 0.5 4 5 5 0.25 4 4 4 0.125 3 4 4200 0.5 5 5 5 0.25 4 4 5 0.125 3 4 4201 0.5 5 5 5 0.25 4 5 4 0.125 3 4 4202 0.5 5 5 5 0.25 4 4 5 0.125 3 4 4203 0.5 4 5 5 0.25 4 4 5 0.125 4 4 4204 0.5 5 5 5 0.25 5 5 5 0.125 4 5 4205 0.5 5 5 5 0.25 4 4 5 0.125 3 4 4Reference A 0.5 4 5 5 0.25 3 4 5 0.125 1 2 3Reference B 0.5 5 5 5 0.25 3 4 4 0.125 2 2 3Reference G 0.5 5 5 4 0.25 4 5 3 0.125 3 2 3Non-treatment -- 0 0 0______________________________________ TABLE 12______________________________________Compound Concentration Herbicidal effectNo. % S.M. C.G. Radish______________________________________228 0.5 5 5 5 0.25 4 5 5 0.125 4 5 5229 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5230 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5231 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5232 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5233 0.5 5 5 5 0.25 5 5 5 0.125 4 4 4234 0.5 5 5 5 0.25 5 5 5 0.125 3 4 4235 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5236 0.5 5 5 5 0.25 4 5 5 0.125 4 3 5Reference A 0.5 5 5 5 0.25 4 4 5 0.125 2 3 3Reference B 0.5 5 5 5 0.25 3 4 4 0.125 3 3 4Reference G 0.5 5 5 4 0.25 5 5 4 0.125 2 3 2Non-treatment -- 0 0 0______________________________________ TABLE 13______________________________________Compound Concentration Herbicidal effectNo. % S.M. C.G. Radish______________________________________239 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5240 0.5 5 5 5 0.25 5 5 5 0.125 3 5 5241 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5242 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5243 0.5 5 5 5 0.25 5 5 5 0.125 5 4 5244 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5245 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5246 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5247 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5248 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5249 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5250 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5251 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5252 0.5 4 5 5 0.25 4 5 5 0.125 3 4 5253 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5254 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5255 0.5 5 5 5 0.25 5 5 5 0.125 4 4 5256 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5257 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5258 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5259 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5260 0.5 4 5 5 0.25 4 4 5 0.125 4 4 5261 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5262 0.5 5 5 5 0.25 4 4 5 0.125 4 4 5263 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5308 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5309 0.5 5 5 5 0.25 4 4 5 0.125 4 4 5310 0.5 4 5 5 0.25 4 5 5 0.125 3 3 5311 0.5 4 5 5 0.25 4 4 5 0.125 3 3 5312 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5313 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5314 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5315 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5316 0.5 5 5 5 0.25 4 4 5 0.125 3 3 5317 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5318 0.5 4 5 5 0.25 4 4 5 0.125 3 3 5319 0.5 4 5 5 0.25 4 4 5 0.125 3 4 5320 0.5 4 5 5 0.25 4 5 5 0.125 4 3 5321 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5322 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5323 0.5 5 5 5 0.25 5 4 5 0.125 3 4 5324 0.5 4 5 5 0.25 4 4 5 0.125 4 4 4325 0.5 4 5 5 0.25 4 4 5 0.125 3 3 5326 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5327 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5328 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5388 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5389 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5390 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5391 0.5 5 5 5 0.25 4 5 5 0.125 4 5 5392 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5393 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5394 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5395 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5396 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5397 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5398 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5399 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5400 0.5 4 5 5 0.25 4 4 5 0.125 3 4 5401 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5402 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5403 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5404 0.5 5 5 5 0.25 4 5 5 0.125 4 5 5405 0.5 4 5 5 0.25 4 5 5 0.125 3 4 5406 0.5 4 5 5 0.25 3 4 5 0.125 3 4 5407 0.5 5 5 5 0.25 5 5 5 0.125 3 4 5408 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5409 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5410 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5411 0.5 5 5 5 0.25 5 5 5 0.125 3 5 5412 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5413 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5414 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5415 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5416 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5417 0.5 5 5 5 0.25 5 5 5 0.125 4 5 5418 0.5 5 5 5 0.25 3 5 5 0.125 3 4 5419 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5420 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5421 0.5 4 5 5 0.25 4 5 5 0.125 3 4 5422 0.5 4 5 5 0.25 4 5 5 0.125 3 4 5423 0.5 5 5 5 0.25 5 5 5 0.125 5 5 5424 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5425 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5426 0.5 5 5 5 0.25 4 5 5 0.125 3 5 5427 0.5 4 5 5 0.25 4 5 5 0.125 4 4 5428 0.5 5 5 5 0.25 4 5 5 0.125 3 4 4429 0.5 4 5 5 0.25 4 5 5 0.125 3 4 4430 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5431 0.5 5 5 5 0.25 4 4 5 0.125 3 4 5432 0.5 5 5 5 0.25 4 4 5 0.125 3 4 4433 0.5 5 5 5 0.25 4 5 5 0.125 4 4 5434 0.5 5 5 5 0.25 4 5 5 0.125 3 4 5Reference A 0.5 5 5 5 0.25 4 4 5 0.125 1 2 3Reference B 0.5 5 5 5 0.25 3 4 4 0.125 1 3 3Reference G 0.5 5 5 4 0.25 4 5 4 0.125 3 3 2Non-treatment -- 0 0 0______________________________________

Claims

1. A method of controlling weeds in the cultivation of a crop plant by applying a herbicidally effective amount of an N-(3-substituted oxyphenyl)-3,4,5,6-tetrahydrophthalimide of the formula: ##STR441## wherein X and Y each represent hydrogen or halogen; ##STR442## or --CN; R.sup.1 is hydrogen or C.sub.1-10 alkyl, phenyl chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is hydrogen or a C.sub.1-12 straight or branched alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, C.sub.1-5 haloalkyl, C.sub.3-4 haloalkenyl, C.sub.2-4 cyanoalkyl, C.sub.2-4 hydroxyalkyl, C.sub.3-6 alkoxyalkyl, C.sub.5-8 alkoxyalkoxyalkyl, C.sub.7-10 alkoxyalkoxyalkoxyalkyl, C.sub.3-8 alkylthioalkyl, C.sub.4-8 cycloalkyl, C.sub.7-9 aralkyl, chlorobenzyl, bromobenzyl, phenyl, .gamma.-butyrolactone optionally substituted by methyl, an alkali metal cation, an alkaline earth metal cation, ammonium cation, or an ammonium cation having 1 to 4 alkyl substituents, wherein the total carbon atom content of the ammonium cation is 1 to 9 carbon atoms; R.sup.4 is C.sub.1-12 alkyl, C.sub.3-6 alkoxycarbonylalkyl or benzyl; R.sup.5 is hydrogen or methyl; R.sup.6 is methyl or phenyl; R.sup.7 and R.sup.8 can be the same or different and each is hydrogen, C.sub.1-10 branched or straight chain alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, C.sub.2-6 haloalkyl, C.sub.2-6 hydroxyalkyl, alkoxyalkyl, aralkyl, phenyl, chlorophenyl, bromophenyl, methylphenyl, methoxyphenyl, pyrimidine, thiazole, pyridine, C.sub.1-6 alkoxy, C.sub.2-4 alkenyloxy, amino, methylamino, phenylamino, dimethylamino, C.sub.1-4 alkanesulfonyl, benzenesulfonyl, toluenesulfonyl, chlorobenzenesulfonyl, methoxybenzenesulfonyl or cyclohexyl; and ##STR443## wherein R.sup.7 and R.sup.8 together form a piperidine, or optionally together with an oxygen form a morpholine, isoxazolidine, or tetrahydroisoxazine ring; and m and n each represent an integer of 1 to 3.

2. The method of claim 1, wherein said weeds are controlled in the cultivation of a crop plant selected from the group consisting of soybean, cotton, sugar beat, sunflower, peas, potatoes, cucumbers, rice, wheat, barley, oats, rye, corn and sugar cane.

3. The method of claim 1, wherein in said tetrahydrophthalimide compound, group X is chlorine and group Y is hydrogen.

4. The method of claim 1, wherein in said tetrahydrophthalimide compound, group X is bromine and group Y is hydrogen.

5. The method of claim 1, wherein in said tetrahydrophthalimide compound, A represents --CHR.sup.1 --; R.sup.1 represents H, C.sub.1-10 alkyl or phenyl; B represents --CONR.sup.7 R.sup.8 ; R.sup.7 and R.sup.8 each represent H, C.sub.1-10 branched or straight chain alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, C.sub.2-6 haloalkyl, C.sub.2-6 hydroxyalkyl, methoxyethyl, benzyl, phenyl, chlorophenyl, bromophenyl, methylphenyl, methoxyphenyl, pyrimidine, thiazole, pyridine, C.sub.1-6 alkoxy, C.sub.2-4 alkenyloxy, amino, methylamino, phenylamino, dimethylamino, C.sub.1-4 alkanesulfonyl, benzenesulfonyl, toluenesulfonyl, chlorobenzenesulfonyl, methoxybenzenesulfonyl, or cyclohexyl; and ##STR444## wherein R.sup.7 and R.sup.8 together form a piperidine, or optionally together with an oxygen form a morpholine, isoxazolidine, or tetrahydroisoxazine ring.

6. The method of claim 5, wherein in said tetrahydrophthalimide compound, R.sup.1 represents a C.sub.1-4 alkyl group; R.sup.7 represents H, a C.sub.1-7 alkyl or a C.sub.1-4 alkoxy group; R.sup.8 represents a C.sub.1-7 alkyl, a C.sub.1-4 alkoxy, a C.sub.2-4 haloalkyl, a C.sub.2-4 hydroxyalkyl, phenyl, aralkyl, a C.sub.3-4 alkenyl or a C.sub.3-5 alkynyl group.

7. The method of claim 6, wherein in said tetrahydrophthalimide compound, R.sup.1 represents a C.sub.1-4 alkyl group; R.sup.7 represents H, a C.sub.1-7 alkyl or a C.sub.1-4 alkoxy group; R.sup.8 represents a C.sub.1-7 alkyl, a C.sub.1-4 alkoxy, a C.sub.3-4 alkenyl, a C.sub.3-5 alkynyl or benzyl group.

8. The method of claim 7, wherein in said tetrahydrophthalimide compound, X represents Cl or Br; Y represents H; R.sup.1 represents a C.sub.1-3 alkyl group; R.sup.7 represents H, methyl or methoxy group; R.sup.8 represents a C.sub.1-4 alkyl, a C.sub.1-4 alkoxy, allyl, propargyl or benzyl group.

9. The method of claims 1, 3 or 4, wherein in said tetrahydrophthalimide compound, ##STR445## R.sup.1 represents hydrogen or C.sub.1-10 alkyl, phenyl, chlorophenyl, bromophenyl, dichlorophenyl, methylchlorophenyl, methylphenyl or nitrophenyl; R.sup.2 represents hydrogen or C.sub.1-14 alkyl; R.sup.3 represents hydrogen, C.sub.1-12 straight or branched alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, C.sub.1-5 haloalkyl, C.sub.3-4 haloalkenyl, C.sub.2-4 cyanoalkyl, C.sub.2-4 hydroxyalkyl, C.sub.3-6 alkoxyalkyl, C.sub.5-8 alkoxyalkoxyalkyl, C.sub.7-10 alkoxyalkoxyalkoxyalkyl, C.sub.3-8 alkylthioalkyl, C.sub.4-8 cycloalkyl, C.sub.7-9 aralkyl, chlorobenzyl, bromobenzyl, phenyl, .gamma.-butyrolactone optionally substituted by methyl, an alkali metal cation, an alkaline earth metal cation, ammonium cation or an ammonium cation containing from 1 to 4 alkyl groups, wherein the total carbon atom content of the ammonium cation is 1 to 9 carbon atoms; R.sup.4 represents C.sub.1-12 alkyl, C.sub.3-6 alkoxycarbonylalkyl or benzyl; R.sup.5 represents hydrogen of methyl; R.sup.6 represents methyl or phenyl; and n and m are each an integer of 1 to 3.

10. The method of claim 9, wherein in said tetrahydrophthalimide compound, group A represents --CHR.sup.1 --, wherein R.sup.1 represents a C.sub.1-4 alkyl or phenyl group; B represents --COOR.sup.3 or --COSR.sup.4 ; R.sup.3 represents a C.sub.1-6 alkyl group; and R.sup.4 represents a C.sub.1-10 alkyl group.

11. The method of claim 10, wherein in said tetrahydrophthalimide compound, group R.sup.3 represents a C.sub.1-4 alkyl group; and R.sup.4 represents a C.sub.2-3 alkyl group.

12. The method of claims 1, 3 or 4, wherein in said tetrahydrophthalimide compound, group A represents --(CHR.sup.1).sub.n --; R.sup.1 represents H or an alkyl group; n is an integer of 1 to 3 and B represents CN.