URACIL DERIVATIVE

Abstract: Compounds represented by general formula (1), a process for the production thereof, a method of killing weeds or controlling their growth therewith, and a herbicide containing the same as the active ingredient. In formula (1), R¹ represents H, C₁ to C₃ alkyl or C₁ to C₃ haloalkyl; R² represents C₁ to C₆ haloalkyl; R³ represents H, C₁ to C₆ alkyl, C₁ to C₆ haloalkly, CH₂OH, halogen or nitro; R⁴ represents H or halogen; R⁵ represents H, halogen, nitro or cyano; X represents O or S; and Da and Db represent each independently H, C₁ to C₈ alkyl, C₁ to C₆ haloalkyl, C₃ to C₈ cycloalkyl, C₂ to C₈ alkenyl, etc., provided that the cases where both of Da and Db represent H, etc., are excluded. These compounds scarcely inflict chemical injury on crop and have a high herbicidal effect on various weeds even in small doses.

Description: This invention relates to a novel uracil derivative and a selective herbicide containing the derivative as an effective ingredient. Many herbicides have heretofore been used to protect important crops such as rice, soybean, wheat, corn, cotton, sugar, beet, etc. from weeds and to enhance the productivity of these important crops. These agents may be roughly classified into three classes depending on the application loci, i.e. agents for upland fields, agents for paddy fields and agents for non-cultivated fields. Each class can be further classified into soil incorporation treatment types, pre-emergence soil treatment types, a post-emergence treatment (foliar treatment) type, etc., depending on the method of application of the agents. In recent years, the global increase in population has meant that crop productivity influences the food economy in many countries. In addition it is inevitable that the form of conventional agriculture will alter towards the 21st century. Agricultural herbicides which can economically and efficiently kill or control the weeds which may be obstacles to crop cultivation are therefore becoming increasingly necessary. Such a herbicide must meet the following requirements: (1) it has a high herbicidal effect at low dosages (particularly in view of environmental protection, it is necessary to kill weeds by applying as little of the herbicide as possible); (2) it has a suitable residual effect (in recent years, it has become a problem that the agent remaining in soil for a long period damages succeeding crops, so it is important to show a suitable residual effect after application); (3) it promptly kills the weeds after application (a short period after chemical treatment the next crops can be seeded and transplanted). (4) its application frequency is low (for a person engaged in agriculture, it is important to make the frequency of complicated work for controlling weeds as low as possible). (5) its spectrum of controlling weeds is wide (it is desirable that the agent is capable of controlling weed species of different characteristics such as broad leaf weeds, grassy weeds, perennial weeds, etc.) (6) it can be applied by various methods (more potent herbicidal effects can be obtained by combining soil treatment effect, foliar treatment, etc.). (7) it does not damage the crops (an agent which can selectively kill weeds only is preferred in cultivated fields where crops and weeds co-exist). It has been known that specific uracil derivatives show herbicidal activity. For example, bromacil has been described in The Pesticide Manual, 8th Edition, p. 89, The British Crop Protection Council (1987), etc. as one of the herbicides having an uracil structure. It has also been known that aryl uracil derivatives have herbicidal activity. For example, such compounds are disclosed in JP-A-61-221178 (US-A-4,746,352, US-A-4,760,163)]; JP-A-63-41466 (US-A-4,859,229); and JP-A-63-107967 (US-A-4,812,164)]. EP-A-0408382 discloses uracil derivatives substituted by a haloalkyl group and a phenyl group, which have herbicidal activity. EP-A-0540023 discloses 1-phenyl-4-trifluoromethyluracil derivatives having herbicidal activity. Aryluracil derivatives are disclosed in, for instance, JP-A-54-147923 (US-A-4,266,056, US-A-4,338,318), WO/89-03825, US-A-4,927,451 and US-A-4,941,909. There has been a desire for aryl uracil compounds which promptly show a high effect against many kinds of weeds including perennial weeds in an extremely low application amount and which have a suitable residual effect and cause substantially no damage to important crops either by the soil treatment method or the foliar treatment method. Accordingly the present invention provides a uracil derivative of formula (I): wherein: R 1 is hydrogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl R 2 is C 1 -C 6 haloalkyl R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxymethyl, a halogen or nitro; R 4 is a hydrogen atom or a halogen; R 5 is a halogen, nitro or cyano; X is an oxygen atom; D a and D b each independently represents hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl C 3 -C 8 alkynyl, -L 2 -D 52 in which D 52 is hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 3 -C 8 cycloalkyl(C 1 -C 4 ) alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, Ar which is a phenyl group which is unsubstituted or substituted by one or two or more substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, a halogen, nitro, C 1 -C 4 alkoxy and C 1 -C 4 alkoxycarbonyl, -L 1 -Ar wherein Ar is as defined above and L 1 is a C 1 to C 6 alkyl chain, a C 2 to C 6 alkenyl chain or a C 2 to C 6 alkynyl chain each of which may be branched, or -L 1 -Het wherein L 1 is as defined above, Het is a pyridine or thiophene ring, and L 2 represents -C(O)-, -SO 2 -, -S(O)-, -S-, -C(O)O-, -C(O)S- or -C(O)C(O)O-, -L 3 -C(O)O-D 52 in which D 52 is C 1 -C 20 alkyl and L 3 is a C 1 -C 6 alkyl chain, -C(O)-ND 52 D 53 in which D 52 is hydrogen and D 53 is C 1 -C 8 alkyl or C 1 -C 6 alkylsulfonyl, =CD 54 -ND 52 D 53 in which D 52 and D 53 are C 1 -C 6 alkyl and D 54 is hydrogen, or alternatively D a and D b together with a nitrogen atom to which they are attached form a 3- to 8-membered ring represented by provided that the cases where (a) D a and D b both represent hydrogen, and where one of D a and D b represents -L 2 -D 52 (L 2 represents -SO 2 -, and D 52 represents C 1 -C 4 alkyl or C 1 -C 3 haloalkyl), and the other of D a and D b is hydrogen, C 1 -C 4 alkyl, C 2 -C 5 alkenyl, or C 3 -C 5 alkynyl; and (b) one of D a and D b is -L 2 -D 52 in which L 2 is -SO 2 - and D 52 is a C 1 -C 4 alkyl or C 1 -C 3 haloalkyl group; are excluded. Characteristic features in the structure of the compound of the present invention are to have a haloalkyl group at the 6-position of the uracil ring and to have a specific combination of R 4 , R 5 and N(D a )D b as the substituents on the benzene ring at the 3-position of the uracil ring. By having such a structure, the compound of the present invention has a permeation and translocation and very high herbicidal activity. As a result, the compound of the present invention has the advantage that it can be applied according to either the soil treatment or the foliar treatment against many kinds of weeds including the perennial weeds, that it can develop a high effect promptly even if applied in small quantities, and that it has a suitable residual effect. The compound of the present invention represented by the formula (1) may exist as a tautomer as shown below when the substituent R 1 is hydrogen, and the present invention embraces all of these tautomeric forms. As a general method for synthesizing an uracil derivative, the uracil skeleton can be synthesized by referring to the synthesis method described in, for example, A.R. Katritzky et al., Comprehensive Heterocyclic Chemistry, 3 , p. 57 (1984), etc. 3-Amino-4,4,4-trifluorocrotonate ester which is one of starting materials may be synthesized by referring to A.W. Lutz et al., Journal of Heterocyclic Chemistry, 9 , (3), p. 513 (1972), etc. Including the above methods, the compound of the present invention can be synthesized by, for example, the methods shown in Schemes 1 to 5. R 1 , R 2 , R 3 , R 4 , R 5 , X, D a and D b in Schemes 1 to 5 have the same meanings as described above, G 1 is C 1 -C 4 alkyl, G 2 is C 1 -C 4 alkyl or a phenyl group, and Hal is a halogen, a methanesulfonyloxy group or a paratoluenesulfonyloxy group. 1. Scheme 1 shows a method for preparing an uracil derivative (1) by reacting phenyliso(thio)cyanate (6) with β-aminoacrylate ester (5) to form an uracil derivative (1a) in a first step, and after isolation of the derivative (1a) or subsequently, without isolation, alkylating 1-position of the uracil ring in a second step. 1 ○ Reaction in the first step The compound (6) is generally used in an amount of 0.5 to 1.5 equivalent, preferably 0.8 to 1.2 equivalent based on the compound (5).The reaction may proceed without any solvent, but it is generally promoted by using a solvent. As the solvent, there may be mentioned aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; halogenated hydrocarbons such as chloroform, methylene chloride, etc.; ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, etc.; nitriles such as acetonitrile, isobutyronitrile, etc.; tertiary amines such as pyridine, N,N-diethylaniline, etc.; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, etc.; sulfur-containing compounds such as dimethylsulfoxide, sulfolane, etc.; water and their mixture, and preferably the aliphatic hydrocarbons, the aromatic hydrocarbons, the acid amides, the sulfur-containing compounds and their mixture.The reaction may proceed without any base, but generally a base in an amount of 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents based on the compound (5) is used. As the base, there may be mentioned nitrogen-containing organic bases such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane, etc.; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.; and metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc., and preferably sodium hydride, sodium hydroxide and potassium hydroxide.The reaction temperature is generally -70 to 200 °C, preferably -30 °C to the reflux temperature of the reaction mixture.The reaction time is generally 5 minutes to 72 hours, preferably 10 minutes to 12 hours.After the reaction is completed followed by acidifying with a mineral acid such as hydrochloric acid, etc., or an organic acid such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc., the derivative (1a) can be isolated. 2 ○ The second step The alkylating agent is used in an amount of 0.5 to 10 equivalents, preferably 0.8 to 5.0 equivalents based on the derivative (1a). As the alkylating agent, there may be mentioned alkylsulfates such as dimethylsulfate, diethylsulfate, etc.; and halogenated alkyls such as methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, methyl iodide, ethyl iodide, etc.The reaction may proceed without any solvent, but it is generally promoted by using a solvent. As the solvent, there may be mentioned aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; halogenated hydrocarbons such as chloroform, methylene chloride, etc.; ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, etc.; nitriles such as acetonitrile, isobutyronitrile, etc.; tertiary amines such as pyridine, N,N-diethylaniline, etc.; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, etc.; sulfur-containing compounds such as dimethylsulfoxide, sulfolane, etc.; water and their mixture, and preferably the aliphatic hydrocarbons, the aromatic hydrocarbons, the ethers, the ketones, the nitriles, the acid amides, the sulfur-containing compounds and their mixture.A base is generally used in an amount of 0.5 to 10 equivalents, preferably 0.8 to 3.0 equivalents based on the derivative (1a). As the base, there may be mentioned nitrogen-containing organic bases such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine; 1,4-diazabicyclo[2.2.2]octane, etc. and inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., and preferably the inorganic bases such as sodium hydride, potassium carbonate, etc. The reaction temperature is generally -30 to 150 °C, preferably -10 °C to the reflux temperature of the reaction mixture.The reaction time is generally 10 minutes to 96 hours, preferably 30 minutes to 48 hours. 2. Scheme 2 shows a method for preparing an uracil derivative (1) by reacting N-phenyl(thio)carbamate (7) with β-aminoacrylate ester (5) to form an uracil derivative (1a) in a first step, and after isolation of the derivative (1a) or subsequently, without isolation, alkylating 1-position of the uracil ring in a second step. 1 ○ Reaction in the first step The compound (7) is generally used in an amount of 0.5 to 1.5 equivalent, preferably 0.8 to 1.2 equivalent based on the compound (5).The reaction generaly requires a solvent. As the solvent, there may be mentioned aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; halogenated hydrocarbons such as chloroform, methylene chloride, etc.; ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, etc.; nitriles such as acetonitrile, isobutyronitrile, etc.; tertiary amines such as pyridine, N,N-diethylaniline, etc.; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, etc.; sulfur-containing compounds such as dimethylsulfoxide, sulfolane, etc.; alcohols such as methanol, ethanol, propanol, butanol, etc.; water and their mixture, and preferably the aliphatic hydrocarbons, the aromatic hydrocarbons, the acid amides, the sulfur-containing compounds and their mixture.A base is generally used in an amount of 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents based on the compound (5). As the base, there may be mentioned nitrogen-containing organic bases such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine, 1, 4-diazabicyclo[2.2.2]octane, etc.; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.; and metal alkylmercaptides such as sodium methylmercaptide, sodium ethylmercaptide, etc., and preferably the inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., and the metal alcoholates such as sodium methoxide, etc.The reaction temperature is generally 0 to 200 °C, preferably the room temperature to the reflux temperature of the reaction mixture.The reaction time is generally 10 minutes to 72 hours, preferably 30 minutes to 24 hours.After completion of the reaction followed by acidifying with a mineral acid such as hydrochloric acid, etc., or an organic acid such as acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc., the derivative (1a) can be isolated. 2 ○ The second step Alkylation can be carried out under the same reaction conditions as in the second step of Scheme 1. 3. Scheme 3 shows a method for preparing an uracil derivative (1) by reacting phenyliso(thio)cyanate (6) with N-alkyl-β-aminoacrylate ester (8) in one step and may be carried out under the same reaction conditions as in Scheme 1. 4. Scheme 4 shows a method for preparing an uracil derivative (1) by reacting N-phenyl(thio)carbamate (7) with N-alkyl-β-aminoacrylate ester (8) in one step and may be carried out under the same reaction conditions as in Scheme 2. 5. Scheme 5 shows a method for preparing an uracil derivative (1) by reacting D a -Hal (10) with an animo material (9) to form an uracil derivative (1b) in a first step, and after isolation of the derivative (1b) or subsequently, without isolation, reacting D b -Hal (11) with the derivative (1b) in a second step. 1 ○ Reaction in the first step The compound (10) is generally used in an amount of 0.3 to 10 equivalents, preferably 0.5 to 2.0 equivalents based on the compound (9). The reaction may proceed without any solvent, but it is generally promoted by using a solvent. As the solvent, there may be mentioned aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; halogenated hydrocarbons such as chloroform, methylene chloride, etc.; ethers such as diethyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, etc.; nitriles such as acetonitrile, isobutyronitrile, etc.; tertiary amines such as pyridine, N,N-diethylaniline, etc.; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, etc.; sulfur-containing compounds such as dimethylsulfoxide, sulfolane, etc., and their mixture.The reaction may proceed without any base, but generally a base in an amount of 0.3 to 10 equivalents based on the compound (9) is used. Also, it may be used in a very excess amount as a solvent. As the base, there may be mentioned nitrogen-containing organic bases such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]octane, etc.; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.; and metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc., and preferably the nitrogen-containing organic bases and the inorganic bases.The reaction temperature is generally -30 to 160 °C, preferably -10°C to 130°C. The reaction time is generally 10 minutes to 48 hours, preferably 30 minutes to 24 hours. 2. The second step The reaction can be carried out under the same conditions as in the first step of Scheme 5. The more preferred compounds are those represented by the formula (I) wherein, subject to the provisos: R 1 is methyl R 2 is trifluoromethyl; R 3 is hydrogen; R 4 is a hydrogen atom or a halogen; R 5 is a halogen; X is an oxygen atom; D a and D b each independently represents hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, -L 2- D 52 in which D 52 is hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 3 -C 8 cycloalkyl(C 1 -C 4 )alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 4 alkoxy (C 1 -C 4 ) alkyl, Ar (Ar is as defined above), -L 1 -Ar (Ar and L 1 are as defined above) -L 1 -Het (Het and L 1 are as defined above) and L 2 is as defined above, -L 3 -C(O)O-D 52 in which D 52 is C 1 -C 20 alkyl and L 3 is a C 1 -C 6 alkyl chain, -C(O)-ND 52 D 53 in which D 52 is hydrogen and D 53 is C 1 -C 8 alkyl or C 1 -C 6 alkylsulfonyl, or =CD 54 -ND 52 D 53 as defined above. The compounds of the present invention can be used in treatment methods either of a soil treatment or a foliar treatment, as herbicides for upland field, paddy field and non-cultivated field. The present invention accordingly further provides a herbicide comprising a suitable carrier and, as an effective ingredient, a uracil derivative of the invention as defined above. The invention also provides a method for killing weeds at a locus, or inhibiting their growth, which comprises applying thereto a uracil derivative of the invention or a herbicide of the invention as defined above. As subjective weeds of the compound of the present invention, there may be mentioned broad-leaved weeds such as Solanum nigrum , Datura nigrum , Abutilon theophrasti , Side spinosa , Ipomoea spps. of Ipomoea purpurea , Amaranthus lividus , Amaranthus vividis , Xanthium strumarium , Ambrosia artemisiaefolia , Helianthus annuus , Galinsoga ciliata , Cirsium arvense , Senecio vulgaris , Erigeron annus , Rorippa indica , Sinapis arvensis , Capsella Bursapastris , Polygonum Blumei , Polygonum convolvulus , Porthlaca oleracea , Chenopodium album , Chenopodium ficifolium , Kochias coparia , Stellaria media , Veronica persica , Commelina communis , Lamium amplexicaule , Lamium purpureum , Euphorbia supina , Euphorbia maculata , Galium aparine , Rubiaakane , Viola arvensis , Sesbania exaltata , Cassia obtusifolia and Bidens pilosa ; Graminaceous weeds such as Sorgham bicolor , Panicum dichotomiflorum , Sorphum halepense , Echinochloa crus-galli , Digitaria adscendens , A vena fatua , Eleusine indica , Setaria viridis and Alopecurus aequalis ; Cyperaceous weeds such as Cyperus rotundus ; and Alisma canaliculatum , Sagittaria trifolia , Sagittaria pygmaea , Cyperus difformis , Cyperus serotinus , Scirpus juncoides , Eleocharis kuroguwai , Lindemia pyxidaria , Monochoria Vaginalis , Potamogeton distinctus , Rotala indica and Echinochloa oryzicola . The compound of the present invention contains a compound which can be used safely to wheat, corn, barley, soybean, rice, cotton, sugar, beet, sorghum, etc. which are important crops. Also, the compound of the present invention is available as a defoliant. For applying the compound of the present invention as a herbicide, it may be generally applied by mixing with a suitable carrier such as a solid carrier, for example, clay, talc, bentonite, diatomaceous earth, white carbon, etc., or a liqiud carrier, for example, water, alcohols including isopropanol, butanol, benzyl alcohol and furfuryl alcohol, aromatic hydrocarbons including toluene and xylene, ethers including anisol, ketones including cyclohexanone and isophoron, esters including butyl acetate, acid amides including N-methylpyrrolidone, or halogenated hydrocarbons including chlorobenzene and the like. If desired, by adding a surfactant, an emulsifier, a dispersant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, an anticaking agent, a stabilizer, etc., it can be provided practically in an optional formulation such as a liquid formulation, an emulsifiable concentrate, a wettable powder, a dry flowable formulation, a flowable formulation, a dust, a granule, etc. The content of the compound of the present invention in the herbicide of the present invention may be an amount which develops the herbicidal activity and not particularly limited, but it is preferably 1 mg to 95 g per 100 g of the herbicide. If necessary, the compound of the present invention may be mixed with any other herbicides, various insecticides, plant growth regulators, synergists, etc., and applied, when the formulation is prepared or applied. Particularly, by mixing and applying with the other herbicides, a cost reduction by decreasing an applied dosage, an enlargement in weed control spectrum or an improvement in herbicidal activity due to synergistic effect of mixed agents can be expected. At this time, a plural known herbicides can be combined simultaneously. As a kind of a herbicide to be mixed with the compound of the present invention, there may be mentioned, for example, compounds described in Farm Chemicals Handbook, issued in 1990. When the compound of the present invention is applied to the soybean, particularly preferred agents to be mixed with the compound of the present invention are trifluralin, pendimethalin, alachlor, metolachlor, metribuzin, linuron, chlorimuron ethyl, imazaquin, imazethapyr, dinoseb, bifenox, clomazone, etc. When the compound of the present invention is mixed with the other agents, a mixing ratio (by weight) of the compound of the present invention to active components of the other agents is preferably 0.001 to 100 : 1 and a content proportion of the compound of the present invention in the mixed agents (herbicides) is preferably 1 mg to 95 g per 100 g of the herbicide. An applied dosage of the compound of the present invention may vary depending on a locus to be applied, a time to be applied, a method for application, cultivated crops, etc., but generally it is suitable in an amount of about 0.0001 to 10 kg, preferably about 0.001 to 5 kg of active component per hectare (ha). The compound of the present invention is a compound having the high herbicidal effect and the suitable residual activity with an extremely low dose, killing the weeds promptly after applying, having broad object of controllig the weeds, having many methods for application of agents, and showing substantially no chemical damage against the important crops. <Best mode for practicing the invention> In the following, the present invention will be explained in more detail by referring to Examples, but the present invention is not limited by the following Examples so long as not exceeding the gist of the invention. [Examples] [Example 1] Synthesis of 3-(4-chloro-2-fluoro-5-(2-thienylsulfonylamino)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-12) In 5 ml of pyridine was dissolved 0.32 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and then 0.19 g of 2-thiophensulfonyl chloride was added to the solution at 5 °C or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The solution was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.3 g of the desired compound as white crystal. [Example 2] Synthesis of 3-(4-chloro-2-fluoro-5-(2,3,4,5-tetrahydroisothiazol-1,1-dioxide-2-yl)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-15) In 5 ml of N,N-dimethylformamide was dissolved 0.25 g of 3-(4-chloro-2-fluoro-5-(3-chloropropansulfonylamino)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.08 g of anhydrous potassium carbonate was added thereto and the mixture was stirred at room temperature for 2 days. After removing N,N-dimethylformamide by distillation, the residue was dissolved in ethyl acetate, washed successively with water and a saturated saline solution, and dried over anhydrous sodium sulfate. By removing ethyl acetate by distillation, a crude product was obtained. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 3 : 2) to obtain 0.1 g of the desired compound as white crystal. [Example 3] Synthesis of 3-(4-chloro-2-fluoro-5-(O,O-diethylphosphorylamino)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-16) In 2 ml of pyridine was dissolved 0.50 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4 (1H,3H)-pyrimidinedione, and then 0.22 ml of diethylchlorophosphate was added dropwise thereto at 5 °C or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The solution was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.39 g of the desired compound as white crystal. [Example 4] Synthesis of 3-(4-chloro-2-fluoro-5-(methoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-22) In 5 ml of pyridine was dissolved 0.38 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and then 0.11 g of methyl chloroformate was added thereto at 5 °C or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The solution was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.28 g of the desired compound as white crystal. [Example 5] Synthesis of 3-(4-chloro-2-fluoro-5-(N-methyl)ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-24) After adding 0.38 g of 3-(4-chloro-5-ethoxycarbonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione to a suspension of 0.04 g of sodium hydride in tetrahydrofuran (10 ml), 0.06 ml of methyl iodide was added dropwise thereto. After 2 hours, ice-water was added thereto and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 5 : 2) to obtain 0.22 g of the desired compound as white crystal. [Example 6] Synthesis of 3-(5-acetylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-17) In 5 ml of benzene was dissolved 2.00 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.61 ml of anhydrous acetic acid was added thereto and the mixture was refluxed for one hour. Benzene was removed by distillation to obtain a crude product. This was washed with hexane to obtain 2.20 g of the desired compound as white crystal. [Example 7] Synthesis of 3-(4-chloro-2-fluoro-5-formylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-21) After stirring 0.080 g of formic acid and 0.180 g of anhydrous acetic acid at 60 °C for one hour, the mixture was cooled to 30 °C. To the mixture was added a mixture of 0.500 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione and 4 ml of chloroform, and the mixture was stirred for one hour. After refluxing for further one hour, 1.3 ml of formic acid was added to the mixture and the mixture was refluxed for one hour. The solvent was removed by distillation using a vacuum pump to obtain a crude product. This was washed with hexane and dried to obtain 0.510 g of the desired compound as brownish white crystal. [Example 8] Synthesis of 3-(4-chloro-5-ethoxalylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-35) In 5 ml of pyridine was dissolved 0.39 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.17 g of ethyl oxalyl chloride was added thereto at 5 °C or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The mixture was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.29 g of the desired compound as white crystal. [Example 9] Synthesis of 3-(4-chloro-2-fluoro-5-(3-methansulfonylureyen-1-yl)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-33) In 10 ml of dry tetrahydrofuran was dissolved 0.34 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.15 g of methylsulfonylisocyanate was added thereto and the mixture was stirred at 30-40 °C for 2 hours. After cooling by allowing to stand, precipitated crystals were collected by filtration and washed with n-hexane to obtain 0.28 g of the desired compound as white crystal. [Example 10] Synthesis of 3-(4-chloro-5-(2,6-dioxo-4-trifluoromethylpiperidin-1-yl)-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-40) To a solution of 0.50 g of 4-(N-(2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl)carbamoyl)-3-trifluoromethylbutyric acid and 7 ml of dry tetrahydrofuran was added dropwise 0.23 g of thionyl chloride at room temperature. After stirring for 2 hours under reflux, the temperature was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The resulting crude product was extracted with ethyl acetate, washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain 0.50 g of the desired compound as crystal. [Example 11] Synthesis of 4-(N-(2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl)carbamoyl)-3-trifluoromethylbutyric acid (Compound D-37) A mixture of 0.50 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 0.27 g of 3-trifluoromethylglutaric anhydride and 6 ml of toluene was stirred at 100 °C for one hour. After cooling to room temperature, the solvent was removed by distillation under reduced pressure to obtain 0.7 g of the desired compound as crystal. [Example 12] Synthesis of methyl 4-(N-(2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl)carbamoyl)-3-trifluoromethylbutyrate (Compound D-38) To a mixture of 0.20 g of 4-(N-(2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl)carbamoyl)-3-trifluoromethylbutyric acid, 0.06 g of potassium carbonate and 4 ml of N,N-dimetylformamide was added 0.05 g of methyl iodide at room temperature and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate and washed successively with water and a saturated saline solution, and dried over anhydrous sodium carbonate followed by removing ethyl acetate by distillation to obtain 0.44 g of the desired compound as crystal. [Example 13] Synthesis of 3-(5-(N-acetyl)propargylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-20) A mixture of 1.05 g of 3-(5-acetylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione and 9 ml of N,N-dimethylformamide was cooled to 0 °C, and 0.13 g of sodium hydride was added to the solution and the mixture was stirred until the temperature was increased to room temperature. Then, 0.33 g of propargyl bromide was added to the mixture and the mixture was stirred at room temperature for 2 days. The mixture was diluted with ethyl acetate and washed successively with water and a saturated saline solution, and dried over anhydrous sodium carbonate followed by removing ethyl acetate by distillation to obtain 0.93 g of the desired compound as crystal. [Example 14] Synthesis of 3-(4-chloro-2-fluoro-5-(N-methanesulfonyl)methoxycarbonylmethylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-13) In 5 ml of N,N-dimethylformamide was dissolved 0.50 g of 3-(4-chloro-2-fluoro-5-methanesulfonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.17 g of anhydrous potassium carbonate and 0.11 ml of methyl chloroacetate were added thereto and the mixture was stirred at room temperature overnight. After removing N,N-dimethylformamide by distillation, the residue was dissolved in ethyl acetate, washed successively with water and a saturated saline solution, and dried over anhydrous sodium sulfate. By removing ethyl acetate by distillation, a crude product was obtained. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 1 : 1) to obtain 0.19 g of the desired compound as colorless viscous oily product. [Example 15] Synthesis of 3-(4-chloro-5-(N-ethanesulfonyl)ethoxycarbonylmethylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-14) In 5 ml of N,N-dimethylformamide was dissolved 0.30 g of 3-(4-chloro-5-ethanesulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.03 g of 60 % sodium hydride and 0.10 g of ethyl chloroformate were added thereto and the mixture was stirred at room temperature for 4 days. After removing N,N-dimethylformamide by distillation, the residue was dissolved in ethyl acetate, washed successively with water and a saturated saline solution, and dried over anhydrous sodium sulfate. By removing ethyl acetate by distillation, a crude product was obtained. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 3 : 2) to obtain 0.10 g of the desired compound as white crystal. [Example 16] Synthesis of 3-(5-benzensulfinamino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-46) In 5 ml of pyridine was dissolved 0.34 g of 3-(3-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.19 g of benzenesulfinyl chloride was added thereto at 5 °C or lower. After reacting the mixture for one hour, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The reaction mixture was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 3 : 1) and recrystallized from n-hexane to obtain 0.03 g of the desired compound as white crystal. [Example 17] Synthesis of 3-(4-chloro-2-fluoro-5-trichloromethylthioaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-42) In 5 ml of N,N-dimethylformamide was dissolved 0.73 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.33 g of anhydrous sodium carbonate and 0.44 g of perchloromethylmercaptane were added thereto and the mixture was stirred at room temperature for 1.5 hours. After removing N,N-dimethylformamide by distillation, the residue was dissolved in ethyl acetate, washed successively with water and a saturated saline solution, and dried over anhydrous sodium sulfate. By removing ethyl acetate by distillation, a crude product was obtained. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 3 : 1) to obtain 0.79 g of the desired compound as colorless viscous oily product. [Example 18] Synthesis of 3-(4-chloro-2-fluoro-5-trichloromethanesulfinaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-43) In 10 ml of 70 % acetic acid was dissolved 0.29 g of 3-(4-chloro-2-fluoro-5-trichloromethylthioaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.14 g of pyridine-bromine complex was added thereto and the mixture was stirred at room temperature for one hour. After removing acetic acid by distillation, the residue was dissolved in ethyl acetate, washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and dried over anhydrous sodium sulfate. By removing ethyl acetate by distillation, a crude product was obtained. This was purified by a preparative thin layer chromatography (developing solvent hexane : ethyl acetate = 5 : 1) to obtain 0.05 g of the desired compound as white crystal. [Example 19] Synthesis of 3-(4-chloro-2-fluoro-5-(2-thenoylamino)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-45) In 5 ml of pyridine was dissolved 0.34 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.17 g of 2-thiophencarbonyl chloride was added thereto at 5 °C or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The solution was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.30 g of the desired compound as white crystal. [Example 20] Synthesis of 3-(4-chloro-2-fluoro-5-(N,N-dimethylmethylideneamino)phenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound D-44) In 2 ml of N,N-dimethylformamide was dissolved 0.40 g of 3- (5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.14 g of N,N-dimethylformamidedimethylacetal was added thereto. After reacting the mixture at 80 °C for 10 hours, N,N-dimethylformamide was removed by distillation to obtain 0.50 g of the desired compound as brownish viscous oily product. The compounds of the present invention synthesized in accordance with the above scheme or Examples including the compounds synthesized in the above Examples are shown in Tables 1 and 2 with their chemical structures and physical properties, respectively. in which Q 1 , Q 2 , Q 3 , Q 4 , Q 30 , Q 32 , Q 38 , Q 43 and Q 48 are as shown below. Compound No. 1 H-NMR δ (ppm) [solvent] Physical property D - 1 3.60 (3H, s), 6.35 (1H, s), 7.12 (1H, d, J=8Hz), 7.39-7.81 (7H, m) [CDC ℓ 3 ] Melting point 188-190°C D - 2 3.18 (3H, s), 3.53 (3H,s), 6.33 (1H, s), 7.05-7.83(7H, m) [CDCℓ 3 ] Melting point 148-150°C D - 3 3.54 (3H, s), 6.36 (1H, s), 6.93-7.29 (4H, m) , 7.62-7.88(3H,m) [CDCℓ 3 ] Melting point 190-192°C D - 4 3.52 (3H, s), 6.36 (1H, s), 6.98-7.80 (7H, m) [CDCℓ 3 ] Melting point 211-212°C D - 5 3.52 (3H, s), 3.77 (3H, s), 6.28 (1H, s), 6.70-7.16(4H, m), 7.48-7.69 (3H, m) [CDCℓ 3 ] Melting point 178-179°C D - 6 2.63 (3H, s), 3.52 (3H, s), 6.37 (1H, s), 6.90-7.80 (7H,m) [CDCℓ 3 ] Melting point 183-185°C D - 7 2.34 (3H, s), 3.52 (3H, s), 6.39 (1H, s), 6.87-7.72 (7H, m) [CDCℓ 3 ] Melting point 182-184°C D - 8 2.38 (3H, s), 3.57 (3H, s), 6.37 (1H, s), 7.08-7.33 (3H,m), 7.57-7.78 (4H,m) [CDCℓ 3 ] Melting point 194-195°C D - 9 3.54 (3H,s), 6.27 (1H, s), 7.01-7.25 (1H, m), 7.53-7.90 (6H,m) [CDCℓ 3 ] Glass-like oily product D - 10 3.56 (3H, s), 6.37 (1H, s), 7.02-8.80 (6H, m) [CDCℓ 3 ] Glass-like oily product D - 11 3.57 (3H,s), 6.29 (1H,s), 7.00-7.25 (2H,m) 7.57 - 8.25 (5H, m) [CDCℓ 3 ] Melting point 210-212°C D - 12 3.58 (3H,s), 6.30 (1H, s), 6.93-7.31 (3H,m), 7.45-7.82 (3H,m) [CDCℓ 3 ] Melting point 173-174°C D - 13 3. 11 (3H, s), 3. 53 (3H, s), 3.71(3H, s), 4.12 (2H, s), 6. 34 (1H, s), 7.41 (1H, d, J=9Hz), 7.80 (1H, d, J=7Hz) [CDC ℓ 3 ] Viscous oily product D - 14 1.36 (3H, t, J=7Hz), 1.43 (3H, t, J=7Hz), 3.51 (3H, s), 3. 80 (2H, q, J=7Hz), 4.27 (2H, q, J=7Hz), 6.21 (1H, s), 7.31 (1H, s), 7.47 (1H, d, J=2Hz) [CDCℓ 3 ] Melting point 155-157°C D - 15 2.52 (2H, q, J=6Hz), 3.12-3.19 (4H, m), 3.47 (3H, s), 6.19 (1H, s), 7.24 (1H, d, J=3Hz), 7.31 (1H, br s), 7.41 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 192-193°C D - 16 1.20 (6H, t, J = 7Hz), 3.38 (3H, s), 2.97 (4H, dq, J=7Hz), 5.41 (1H, d, J=7Hz), 6.12 (1H, s), 7.04 (1H, d, J=9Hz), 7.06 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 130-132°C D - 17 2.15 (3H,s), 3.47 (3H,s), 6.54 (1H,s), 7.70 (1H, d, J=9Hz), 7.90 (1H, d, J=8Hz), 9.56 (1H, br s) [d 6 -DMSO] Melting point 263-266°C D - 18 3.45 (3H, s), 6.2 (1H,s), 7.25 (1H, d, J=9Hz), 8.13 (1H,d,J=7Hz), 8.86 (1H,br s) [CDCℓ 3 ] Viscous oily product D - 19 3.44 (3H, s), 6.21 (1H, s), 7.22 (1H, d, J=9Hz), 8.04 (1H, d, J=7Hz), 8.44 (1H, br s) [CDCℓ 3 ] Melting point 144-145°C D - 20 1.87 (3H, s) , 2.20 (1H, t, J=2Hz), 3.53 (3H, s), 3.62-4.11 (1H, m), 4.78-5.21 (1H, m), 6.28 (1H, s), 7.28 (1H, d, J=7Hz), 7.35 (1H, d, J=10Hz) [CDCℓ 3 ] Melting point 169-171°C D - 21 3.42 (3H, s), 6.28 (1H, s), 7.34 (1H, d, 1=10Hz), 8.17 (1H, d, J =8Hz), 8.27 (1H, br s), 9.67 (1H, br s), [d 6 -DMSO] Melting point 268-270°C D - 22 3.51 (3H, s), 3.72 (3H, s), 6.30 (1H, H, s), 7.10 (1H, br s), 7.27 (1H, d, J=9Hz), 8. 18 (1H, d, J =7Hz) [CDCℓ 3 ] Melting point 136-138°C D - 23 1.26 (3H, t, J=7Hz), 3.37 (3H, s) , 4.16 (2H, q, J=7Hz), 6.45 (1H, s), 7.57 (1H, d, J=9Hz), 7.77 (1H, d, J=7Hz), 9.10 (1H, br s) [d 6 -DMSO] Melting point 153-155°C D - 24 1.16 (1H, t, J=7Hz), 3. 16 (3H, s) , 3. 49 (3H, s), 3. 51 (2H, q, J=7Hz), 6.24 (1H, s), 7.07 (1H, d, J=7Hz), 7.23 (1H, d, J=9Hz) [CDCℓ 3 ] Melting point 144-146°C D - 25 0.94 (3H, t, J=7Hz), 1.70 (2H, m), 3.47 (3H, s), 4.04 (2H, t, J=7Hz), 6.21 (1H, s), 6.95 (1H, br s), 7.14 (1H, d, J=9Hz), 8.06 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 152-154°C D - 26 0.98 (3H, t, J=6Hz), 1.18-1.73 (4H, m), 3.48 (3H, s), 4.12 (2H, t, J=6Hz), 6.25 (1H, s), 6.98(1H, br s), 7.16 (1H, d, J=9Hz), 8.11 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 117-118°C D - 27 0. 98 (6H, d, J=6Hz), 1.18 - 2. 25 (1H, m), 3.50 (3H, s), 3.91 (2H, d, J=6Hz), 6.24 (1H, s), 7.00 (1H, br s), 7. 18 (1H, d, J=9Hz), 8.11 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 129-131°C D - 28 3.50 (3H, s), 3.67 (2H, t, J= 6Hz) 4.38 (2H, t, J=6Hz), 6.24 (1H, s), 7.09 (1H, br s), 7.18 (1H, H, d, J=9H), 8.08 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 153-154°C D - 29 3.49 (3H, s), 4. 71 (2H, s), 6.22 (1H, s), 7.17 (1H, d, J=8Hz), 7. 22 (1H, br s), 8.00 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 158-161°C D - 30 3.36 (3H, s), 3.51(3H, s), 3.55-3.69 (2H, m), 4.20-4.40 (2H, m), 6.23 (1H, s), 7.10 (1H, br s), 7.16 (1H, d, J=9Hz), 8.07 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 119-120°C D - 31 2.97 (3H, s), 5.11 (2H, s), 6.23 (1H, s), 7.19 (1H, d, J=9Hz), 7.21 (1H, br s), 7.26 (5H, s), 8.11 (1H, d, J=7Hz) [CDCℓ 3 ] Glass-like oily product D - 32 3.48 (3H, s) , 6.21 (1H, s), 7.05-7.60 (7H, m), 8.20 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 158-160°C D - 33 3.22 (3H, s), 3.48 (3H, s), 6.23 (1H s) , 7.20 (1H, d, J=9Hz), 8.11 (1H, d, J=7Hz), 8.28 (1H, b r s) [d 6 -DMSO] Melting point 214-216°C D - 34 2.69 (3H, br d, J=3Hz), 3.54 (3H, s), 5.62 (1H,br s), 6.3 6 (1 H, 3), 7. 15 (1H, br s), 7.16 (1H, d, J=9Hz), 8.26 (1H, d, J=8Hz) [CDCℓ 3 ] Melting point 216-218°C D - 35 1.43 (3H, t, J=6Hz), 3.52 (3H, s), 4.38 (2H, q, J=6Hz), 6.23 (1H, s), 7.23 (1H, d, J=9Hz), 8. 34 (1H, d, J=7Hz), 9.29 (1H, br s) [CDC ℓ 3 ] Melting point 127-129°C D - 36 0.93-1.47 (3H, m), 2.42 (5H, br s), 3.54 (3H, s), 6.37 (1H, s) 7.38 (1H, d, J=9Hz), 7.97 (1H, s), 8.45 (1H, d, J = 7Hz), 9.57 (1H, br s) [CDCℓ 3 ] Glass-like oily product D - 37 2.45-3.81 (5H, m) , 3.46 (3H, s). 6.21 (1H, s), 7.10 (1H, d, J=9Hz), 7.93 (1H, d, J=10Hz), 8.14 (1H, br s) [CDC ℓ 3 ] Melting point 115-119°C D - 38 2. 47-2.94 (5H, m), 3.47 (3H, br s), 3.61 (3H, s), 6.21 (1H, s), 7.10 (1H, d, J=9Hz), 7.91 (1H, br s), 8.14 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 158-160°C D - 39 0.79-1.41 (3H, m), 2.00-3.23 (5H, m), 3.52 (3 H, s), 6.39 (1H, s), 7.16 (1H, d, J=7Hz), 7.46 (1H, d, J=9Hz), [CDCℓ 3 ] Melting point 161-165°C D - 40 2.69-3.35 (5H, m), 3. 46 (3H, s), 6.78 (1H, s), 7.21 (1H, d, J=7Hz), 7.43 (1H, d, J=9Hz) [d 6 -DMSO] Melting point 253-254°C D - 41 2.88 (4H, s), 3.42 (3H H, s), 6.39 (1H, s), 7.50 (1H, d, J=7Hz), 7.64 (1H, d, J=9Hz) [d 6 -DMSO] Melting point 158-161°C D - 42 3.50 (3H, s), 6.31 (1H, s), 6. 86 (1H, br s), 7.22 (1H, d, J=9Hz), 7.53 (1H, d, J=7Hz) [CDCℓ 3 ] Oily product D - 43 3.53 (3H, s), 6.32 (1H, s), 6.54 (1H, br s), 7.28 (1H, s), 7.44 (1H d, J=3Hz) [CDCℓ 3 ] Melting point 165-167°C D - 44 2.95 (6H, s), 3.46 (3H, s), 6.20 (1H, s), 6.63 (1H, d, J=7Hz), 7.13 (1H, d, J=9Hz), 7.31(1H, s) [CDCℓ 3 ] Viscous oily product D - 45 3.50 (3H, s), 6.25 (1H, s), 6.95-7.65 (4H, m), 8.10 (1H, br s) , 8.42 (1H d, J=7Hz) [CDCℓ 3 ] Melting point 1 4 8 - 1 5 0 °C D - 46 3.49 (3H, s) , 6.21 (1H, s) , 6.65 - 6.79 (9H, m) [CDC ℓ 3 ] Melitng point 220-222°C (decomposition) D - 47 1.29 (3H, t, J=7Hz), 2.42 - 3.81 (5H, m), 3.60 (3H, br s), 4.19 (2H, q, J=7Hz), 6.41 (1H, s), 7.25 (1H, d, J=10Hz), 8.20 (1H, br s) [CDCℓ 3 ] Melting point 73 - 75°C D - 48 3.54 (3H, s), 6.35 (1H, s), 6.80 - 7. 88 (8H, m), 8.99 (1H, br s) [d 6 - DMSO] Melting point 217 - 219°C D - 49 1.48 (3H, d, J=7Hz), 3.58 (3H, s), 4.51(2H, q, 1=7Hz), 6.35 (1H, s), 7.20(1H, d, J=9Hz), 7.47-8.01 (5H, s), 8.62 (1H, br. s) [CDCℓ 3 ] Melting point 175-177°C D - 50 2.34 (3H, s), 3.49 (3H, s), 6.21 (1H, s), 7.16 (1H, d, J=8Hz), 7.41 (1H, br s), 8.11(1H, d, J = 7Hz) [CDCℓ 3 ] Melting point 149-151°C D - 51 3.50 (3H, s), 5.15 (2H, s), 6.33 (1H, s) 6.80-7.51 (6H, m), 8. 23 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 142-144°C D - 52 3.50 (3H, s), 5.10 (2H, s), 6.25 (1H, s), 7.11-7.35 (6H, m), 8.11 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 134-136°C D - 53 2.31 (3H, s), 3.48 (3H, s), 5.54 (2H, s), 6. 20 (1H, s), 6.95 - 7.25 (6H, m), 8.08 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 142-143°C D - 54 1.00 (9H, s), 3.56 (3H, s), 3.86(2H, s), 6.37 (1H,s), 7.09(1H, br s), 7.20 (1H, d, J=9Hz), 8.22 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 150-152°C D - 55 3.54 (3H, s), 4.19 (2H, s), 6.34 (1H, s), 7.10-7.41 (6H, m), 8.07(1H,d, J=7Hz), 8.61 (1H, br s) [CDC ℓ 3 ] Melting point 192-193°C D - 56 3.59 (3H, s), 6.36 (1H, s), 7. 35-7.90 (3H, m) [d 6 -DMSO] Melting point 189-191°C D - 57 3.48 (3H, s), 6.50 (1H, s), 7.38 -7.90 (8H, m) [d 6 -DMSO] Melting point 211-223°C D - 58 3.56 (3H, s), 3.80 (3H, s), 6.36 (1H, s-), 6.75-7.66 (3H, m), 8.20 (1H, br s) [CDC ℓ 3 ] Melting point 130-132°C D - 59 3.48 (3H, s), 3.74 (3H, s), 6.44 (1H, s), 7.11-7.90 (3H,m) [d 6 -DMSO] Melting point 254-256°C D - 60 3.53 (3H, s), 3.79 (3H, s), 6.33 (1H, s), 7.38-7.68 (2H, m), 8.19 (1H, br s) [d 6 -DMSO] Melting point 183-185°C D - 61 1.30 (3H, t, J=7Hz), 3.51 (3H, br s), 4.21 (2H, q, J=7Hz) , 6.32 (1H, s), 7.09 (1H, br s), 7.44 (1H, d, J=8Hz), 8.20 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 147-149°C D-62 3.49 (3H, s), 6.32 (1H, s), 7.19-8.00 (7H, m) [CDCℓ 3 -DMSO-d 6 ] Melting point 205-207°C D - 63 3.51 (3H, s), 3.79 (3H, s), 5.10 (2H, s), 6.31 (1H, s), 6.78-7, 45 (6H, m), 8. 22 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 147-148°C D - 64 2.38 (3H, s), 3.57 (3H, s), 5.19 (2H, s), 6. 33 (1H, s), 7.11 - 7.4 0 (6H, m), 8.26 (1H, d, J=8Hz) [CDCℓ 3 ] Melting point 152-154°C D - 65 Melting point 119-121°C D - 66 3.52 (3H, s), 3. 73(3H, s), 6.27 (1H, s), 7.05 (1H, br s), 7.36 (1H, d, J=8Hz), 8.08 (1H, d, J =7Hz) [CDC ℓ 3 ] Melting point 114 - 116 °C D - 67 0.95 (3H, t, J=7Hz), 1.28-1.98(2H,m), 3.50 (3H,br s), 4.10 (2H,t,J=7Hz) 6.31 (1H,s),7.11 (1H,br s), 7.43 (1H,d,)=8Hz), 8.19 (1H,d, J=7Hz) [CDCℓ 3 ] Melting point 154-157°C 154-157°C D - 63 3.53 (3H,s), 3.79 (3H,s), 6.36 (1H,s), 6.75-8.20 (4H,m), [CDCℓ 3 ] Melting point 125-126°C D - 69 3.54 (3H,s), 5.11 (2H,s),6.31 (1H,s), 7.11-7.60 (7H,m), 8.20 (1H,d,J=7Hz) [CDCℓ 3 ] Melting point 110-112°C D - 70 1.23 (3H, t, J=7Hz), 2.63 (2H,q,J=7Hz), 3.54 (3H, s), 5.17 (2H, s), 6.36 (1H, s), 7.20-7.38 (6H, m), 8.29 (1H, d, J=7Hz), [CDCℓ 3 ] Melting point 131-133°C D - 71 1.32 (9H, s), 3.53 (3H, s), 5.16 (1H, s), 6.35 (1H, s), 7.17-7.46 (6H, m) 8.27 (1H, d, J=7Hz) [CDCℓ 3 ] Semi-solid D - 72 3.52 (3H, s), 5.23 (2H, s), 6. 34 (1H, s), 7.30-7.70 (6H, m), 8. 22 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 103-104°C D - 73 3.54 (3H, s), 5.27 (2H, s), 6.36 (1H, s), 7.20-7.70 (4H, m), 8.10-8.40 (3H, m) [CDCℓ 3 ] Glass-like D - 74 3.56 (3H, s), 5.32 (2H, s), 6.35 (1H, s), 7.20 - 7. 75 (5H, m), 8.27 (1H, d, J=7Hz), 8.69 (1H, d, J =5Hz) [CDCℓ 3 ] Glass-like D - 75 3.52 (3H, s), 5.34 (2H, s), 6.34 (1H, s), 6.88-7.45 (5H, m), 8.26 (1H, d, J=7Hz), [CDCℓ 3 ] Melting point 167-169°C D - 76 1.61 (3H, d, J=6Hz), 3.56 (3H, s), 5.89 (1H, q, J = 6Hz), 6.38 (1H, s), 7.12-7.55 (7H, m), 8.29 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 163-164°C D - 77 2.99 (2H, t, J=7Hz), 3.54 (3H, s), 4.39 (2H,t, J=7Hz), 6.35 (1H, s), 7.05-7.40 (7H, H, m), 8.20 (1H, d, J=8Hz) [CDCℓ 3 ] Melting point 87-88°C D - 78 3.56 (3H, s), 4.60 (2H, q, J=8Hz), 6.38 (1H, s), 7.36 (1H, d, J=9Hz), 7.38 (1H,br s), 8.19 (1H,d,J=7Hz) [CDCℓ 3 ] Melting point 164-165°C D - 79 1.76-2.26 (9H, m), 3.55 (3H,s) 4.15 (2H,d,J=6Hz), 6. 35(1H,s), 7.15(1H,br s), 7.39 (1H, d, J=9Hz), 8.26 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 116-118°C D - 80 1.74 (3H, d, J=5Hz), 3.35 (3H, s), 4.61 (2H, m), 5.59-5.88 (2H, m), 6.39 (1H, s), 7.18 (1H, br s), 7.34 (1H, d, J=9Hz), 8. 23 (1H, d, J=7Hz), [CDCℓ 3 ] Glass-like D - 81 3.52 (3H, s), 4.34 (2H, d, J=5Hz), 5.72 (1H, br s), 6.30 (1H, s), 6.99 (1H, br s), 7.08 (1H, d, J=9Hz), 7.20 (5H, s), 8. 33 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 165-167°C D - 82 3.60 (3H, s), 4.69 (2H, d, J=5Hz), 5.18-6.13 (3H, m), 6.41 (1H, s), 7.23 (1H, br s), 7.36 (1H, d, J=9Hz), 8.28 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 148-149°C D - 83 3.57 (3H, s), 4.87 (2H, d, J=6Hz), 6.32-6.12 (3H, m), 7.19-7.49 (7H, m), 8.27 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 114-116°C D - 84 3.56 (3H, s), 5. 25 (2H, s), 6.39 (1H, s), 7.15-8.71 (7H, m) [CDCℓ 3 ] Melting point 170-111°C D - 85 3.59 (3H, s), 5.22 (2H, s), 6.38 (1H, s), 7.12-7.51 (4H, m), 8.21 (1H, d, J=7Hz), 8.12 (2H, d, J =6Hz) [CDCℓ 3 ] Melting point 208-209°C D - 86 3.55 (3H, s), 5.21 (2H, s), 6.40(1H,s), 7.08-7.49 (5H, m), 8.30(1H,br s) [CDCℓ 3 ] Melting point 155-156°C D - 87 3.49 (3H, s), 5.36 (2H, s), 6.32 (1H, s), 7.21-8.03 (9H, m), 8.31 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 130-132°C D - 88 2.34 (3H, s), 3.50 (3H, s), 6.29 (1H, s), 6.92-7.55 (6H, m), 8.24 (1H, d, J =7Hz) [CDCℓ 3 ] Melting point 145-147°C D - 89 3.06 (3H, s), 3.53 (3H, s), 4.59 (2H, s) , 6.34 (1H, s), 6.90-7.40 (7H, m), 8.43 (1H, d, J=8Hz) [CDCℓ 3 ] Melting point 143-145°C D - 90 1.45-1.80 (6H, m), 3.28-3.64 (7H, m), 6.28 (1H, s), 7.00 (1H, br s), 7.29 (1H, d, J=9Hz), 8.39 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 99-100°C D - 91 3.50 (3H, s), 4.00 (3H, s), 6.35 (1H, s), 7.21 (1H, d, J=8Hz), 7.85 (1H, d, J=7Hz), 8.19 (1H, br s) [CDCℓ 3 ] Melting point 123-125°C D - 92 3.57 (3H, s), 4.39 (2H, s), 6.39 (1H, s), 6.78 (1H, br s), 7.28 (1H, d, J=9Hz), 7.30 (5H, s), 7.68 (1H, d, J=7Hz) [CDCℓ 3 ] Melting point 160-162°C D - 93 2.59 (3H, s), 3.50 (3H, s), 6.22 (1H, s), 7.20 (1H, d, J=8Hz), 7.91(1H, d, J=7Hz), 8.07 (1H, br s) [CDCℓ 3 ] Melting point 123-125°C D - 94 3.53 (3H, s), 5.54 (2H, s), 6.34 (1H, s), 7.32 (1H, d, J=9Hz), 7. 36(5H, s), 7.98 (1H, d, J=9Hz), 8.38 (1H, br s) [CDCℓ 3 ] Melting point 71-73°C D - 95 3.55 (3H,s), 3. 72(3H,s), 4.43 (2H, s), 6.35 (1H, s), 7.47 (1H, d, J=9Hz), 7.71 (1H, d, J=9Hz), 8.29 (1H, s) [CDCℓ 3 ] Melting point 152-154°C D - 96 3.46 (3H, s), 3.62 (2H, d, J=5Hz), 3. 74 (3H, s), 4.91 (1H, t, J=5Hz), 6.26 (1H, s), 6.35 (1H, d, J=7Hz), 7.22 (1H, d, J=9Hz) [CDCℓ 3 ] Glass-like D - 97 1.47 (3H, d, J=7Hz), 3.72 (3H, s), 3.79 (3H, s), 4.06 (1H, dq, J=7, 7Hz), 4.73 (1H, br s), 6.34 (1H, s), 6.45 (1H, d, J=7Hz), 7.26 (1H, d, J=9Hz) [CDCℓ 3 ] Viscous oily product D - 98 1.25 (3H, t, J=7Hz), 1.45 (3H, d, J=7Hz), 3.48 (3H, s), 4.15 (1H, dq, J=7,7Hz), 4.17 (2H, q, J=7Hz), 4.82 (1H, br s), 6.31 (1H, s), 6.45 (1H, d, J = 7Hz), 7.23 (1H, d, J=9Hz) [CDCℓ 3 ] Viscous oily product D - 99 D-100 D-101 D-102 D-103 D-104 The compounds of the present invention synthesized in accordance with the above scheme or Examples including the compounds synthesized in the above Examples are shown below, but the present invention is not limited by these. in which R 6 represent the following: (Abbreviations indicate respectively the meanings as shown below. Me: methyl group, Et: ethyl group, Ph: phenyl group, n-Bu: normal butyl group, s-Bu: secondary butyl group, i-Bu: iso butyl group, t-Bu: tertiary butyl group, n-Pr: normal propyl group, i-Pr: iso propyl group, n-Am: normal amyl group, t-Am: tertiary amyl group, n-Hex: normal hexyl group, c-Pr: cyclopropyl group, c-Bu: cyclobutyl group, c-pen: cyclopentyl group, c-Hex: cyclohexyl group) NHSO 2 -t-Am, NHSO 2 -n-Am, NHSO 2 -n-Hex, NHSO 2 CH 2 (CH 2 ) 6 Me, NHSO 2 CH 2 (CH 2 ) 8 Me, NHSO 2 CH 2 (CH 2 ) 10 Me, NHSO 2 CH 2 (CH 2 ) 12 Me, NHSO 2 CH 2 (CH 2 ) 14 Me, NHSO 2 CH 2 (CH 2 ) 16 Me, NHSO 2 CH=CH 2 , NHSO 2 CH 2 CH=CH 2 , NHSO 2 CH(Me)CH=CH 2 , NHSO 2 C(Me) 2 CH=CH 2 , NHSO 2 CH 2 C≡CH, NHSO 2 CH(Me)C≡CH, NHSO 2 C(Me) 2 C≡CH, NHSO 2 CH=CHPh, NHSO 2 (CF 2 ) 3 CF 3 , NHSO 2 (CF 2 ) 5 CF 3 , NHSO 2 (CF 2 ) 7 CF 3 , NHSO 2 CH 2 Si(Me) 3 , NHSO 2 CH 2 SO 2 Me, NHSO 2 CH 2 Ph, NHSO 2 CH 2 CH 2 Ph, NHSO 2 CH 2 -(2-F-Ph), NHSO 2 CH 2 -(3-F-Ph), NHSO 2 CH 2 -(4-F-Ph), NHSO 2 CH 2 -(2-Cℓ-Ph), NHSO 2 CH 2 -(3-Cℓ-Ph), NHSO 2 CH 2 -(4-Cℓ-Ph), NHSO 2 CH 2 -(2-Br-Ph), NHSO 2 CH 2 -(3-Br-Ph), NHSO 2 CH 2 -(4-Br-Ph), NHSO 2 CH 2 -(2-l-Ph), NHSO 2 CH 2 -(3-l-Ph), NHSO 2 CH 2 -(4-l-Ph), NHSO 2 CH 2 -(2-Me-Ph), NHSO 2 CH 2 -(3-Me-Ph), NHSO 2 CH 2 -(4-Me-Ph), NHSO 2 CH 2 -(2-MeO-Ph), NHSO 2 CH 2 -(3-MeO-Ph), NHSO 2 CH 2 -(4-MeO-Ph), NHSO 2 CH 2 -(2-NO 2 -Ph), NHSO 2 CH 2 -(3-NO 2 -Ph), NHSO 2 CH 2 -(4-NO 2 -Ph), NHSO 2 CH 2 -(2-MeOCO-Ph), NHSO 2 CH 2 -(3-MeOCO-Ph), NHSO 2 CH 2 -(4-MeOCO-Ph), NHSO 2 CH 2 -(2-CF 3 -Ph), NHSO 2 CH 2 -(3-CF 3 -Ph), NHSO 2 CH 2 -(4-CF 3 -Ph), NHSO 2 CH 2 -(2-CF 3 O-Ph), NHSO 2 CH 2 -(3-CF 3 O-Ph), NHSO 2 CH 2 -(4-CF 3 O-Ph), NHSO 2 NHCO 2 Me, NHSO 2 NHCO 2 Et, NHSO 2 NHCO 2 -n-Pr, NHSO 2 NHCO 2 -i-Pr, NHSO 2 OMe, NHSO 2 OEt, NHSO 2 O-i-Pr, NHSO 2 O-n-Pr, NHSO 2 OCH 2 Cℓ, NHSO 2 OSi(Me) 3 , NHSO 2 Ph, NHSO 2 -(2-F-Ph), NHSO 2 -(3-F-Ph), NHSO 2 -(4-F-Ph), NHSO 2 -(2-Cℓ-Ph), NHSO 2 -(3-Cℓ-Ph), NHSO 2 -(4-Cℓ-Ph), NHSO 2 -(2-Br-Ph), NHSO 2 -(3-Br-Ph), NHSO 2 -(4-Br-Ph), NHSO 2 -(2-l-Ph), NHSO 2 -(3-l-Ph), NHSO 2 -(4-l-Ph), NHSO 2 -(2-Me-Ph), NHSO 2 -(3-Me-Ph), NHSO 2 -(4-Me-Ph), NHSO 2 -(2-MeO-Pb), NHSO 2 -(3-MeO-Ph), NHSO 2 -(4-MeO-Ph), NHSO 2 -(4-Et-Ph), NHSO 2 -(4-n-Pr-Ph), NHSO 2 -(4-i-Pr-Ph), NHSO 2 -(4-n-Bu-Ph), NHSO 2 -(4-s-Bu-Ph), NHSO 2 -(4-i-Bu-Ph), NHSO 2 -(4-t-Bu-Ph), NHSO 2 -(4-t-Am-Ph), NHSO 2 -(4-n-Hex-Ph), NHSO 2 -(2-NO 2 -Ph), NHSO 2 -(3-NO 2 -Ph), NHSO 2 -(4-NO 2 -Ph), NHSO 2 -(2-MeOCO-Ph), NHSO 2 -(3-MeOCO-Ph), NHSO 2 -(4-MeOCO-Ph), NHSO 2 -(2-CF 3 -Ph), NHSO 2 -(3-CF 3 -Ph), NHSO 2 -(4-CF 3 -Ph), NHSO 2 -(2-CF 3 O-Ph), NHSO 2 -(3-CF 3 O-Ph), NHSO 2 -(4-CF 3 O-Ph), NHSO 2 -(4-CF 3 CF 2 O-Ph), NHSO 2 -(3-MeCO-Ph), NHSO 2 -(3-HOCO-Ph), NHSO 2 -(4-HOCO-Ph), NHSO 2 -(2,4-di-NO 2 -Ph), NHSO 2 -(4-Cℓ-3-NO 2 -Ph), NHSO 2 -(2-Me-5-NO 2 -Ph), NHSO 2 -(4-Cℓ-3-HOCO-Ph), NHSO 2 -(2-MeCONH-Ph), NHSO 2 -(3-MeCONH-Ph), NHSO 2 -(4-MeCONH-Ph), NHSO 2 -(2-NO 2 -4-CF 3 -Ph), NHSO 2 -(3,5-di-CF 3 -Ph), NHSO 2 -(4-(2,2-dichlorocyclopropyl)-Ph), NHSO 2 -(3-NO 2 -4-t-Bu-Ph), NHSO 2 -(4-(1-bromoethyl)-Ph), NHSO 2 -(2,5-di-MeO-Ph), NHSO 2 -(4-dimethylamino-3-NO 2 -Ph), NHSO 2 -(4-Cℓ-3-C F 3 -Ph), NHSO 2 -(2,4-di-Me-3-NO 2 -Ph), NHSO 2 -(2,4-di-Cℓ-5-Me-Ph) , NHSO 2 -(4-Cℓ-2, 5-di-Me-Ph), NHSO 2 -(2-Cℓ-6-Me-Ph), NHSO 2 -(3-Cℓ-4-MeO-Ph), NHSO 2 -(3-Cℓ-2-Me-Ph), NHSO 2 -(2-Cℓ-5-CF 3 -Ph), NHSO 2 -(2-Cℓ-4-CF 3 -Ph), NHSO 2 -(2-CN-Ph), NHSO 2 -(3-CN-Ph), NHSO 2 -(4-CN-Ph), NHSO 2 -(5-F-2-Me-Ph), NHSO 2 -(5-Cℓ-2-MeO-Ph), NHSO 2 -(2,4-di-i-Pt-Ph), NHSO 2 -(6-MeO-3-Me-Ph), NHSO 2 -(2,4-di-MeO-Ph), NHSO 2 -(3,4-di-MeO-Ph), NHSO 2 -(3,5-di-MeO-Ph), NHSO 2 -(2,5-di-MeO-Ph), NHSO 2 -(2,6-di-MeO -Ph), NHSO 2 -(2,3-di-MeO-Ph), NHSO 2 -(2,4-di-Cℓ-Ph), NHSO 2 -(3,4-di-Cℓ-Ph), NHSO 2 -(3,5-di-Cℓ-Ph), NHSO 2 -(2,5-di-Cℓ-Ph), NHSO 2 -(2,6-di-Cℓ-Ph), NHSO 2 -(2,3-di-Cℓ-Ph), NHSO 2 -(2,4,6-tri-Cℓ-Ph), NHSO 2 -(2,4-di-F-Ph), NHSO 2 -(3,4-di-F-Ph), NHSO 2 -(3,5-di-F-Ph), NHSO 2 -(2,5-di-F-Ph), NHSO 2 -(2,6-di-F-Ph), NHSO 2 -(2,5-di-Br-Ph), NHSO 2 -(3,4-di-Br-Ph), NHSO 2 -(2-Cℓ-4-F-Ph), NHSO 2 -(3-Cℓ-4-F-Ph), NHSO 2 -(pentafluoro-Ph), NHSO 2 -(pentamethyl-Ph), NHSO 2 -(2,4,6-tri-Me-Ph), NHSO 2 -(2,4,6-tri-i-Pr-Ph, NHSO 2 -(2,3,5,6-tetra-Me-Ph), NHSO 2 -(2,4-di-Me-Ph), NHSO 2 -(3,4-di-Me-Pb), NHSO 2 -(3,5-di-Me-Ph), NHSO 2 -(2,5-di-Me-Ph), NHSO 2 -(2,6-di-Me-Ph), NHSO 2 -(2,3-di-Me-Ph) , NHSO 2 -Q1, NHSO 2 -Q2, NHSO 2 -Q3, NHSO 2 -Q4,NHSO 2 -Q5, NHSO 2 -Q6, NHSO 2 -Q7, NHSO 2 -Q8, NHSO 2 -Q9, NHSO 2 -Q10, NHSO 2 -Q11, NHSO 2 -Q12, NHSO 2 -Q13, NHSO 2 -(3-CF 3 -Q1), NHSO 2 -(3-CON(Me) 2 -Q1), NHSO 2 -(2-Cℓ-Q2), NHSO 2 -(2-Cℓ-Q3) , NHSO 2 -(4,5-di-Br-Q4), NHSO 2 -(2,5-di-Cℓ-Q4), NHSO 2 -(4,5-di-Cℓ-Q4), NHSO 2 -(5-Cℓ-Q4), NHSO 2 -(5-Br-4-Cℓ-Q4), NHSO 2 -(4-Br-5-Cℓ-Q4), NHSO 2 -(3-Br-5-Cℓ-Q4), NHSO 2 -(7-Cℓ-Q5), NHSO 2 -(7-Me-Q5), NHSO 2 -(3, 5-di-Me-Q8), MHSO 2 -(3-M e-5-Cℓ-Q8), NHSO 2 -(3-Me-5-MeOCO-Q8), NHSO 2 -(4-MeOCO-Q9), NHSO 2 -(4-MeOCO-Q10), NHSO 2 -(2,4-di-Me-Q11), NHSO 2 -(3,5-di-Me-Q12), NHCOMe, N(COMe)Me, N(COMe)Et, N(COMe)-n-Pr, N(COMe)-i-Pr, N(COMe)CH 2 C≡CH, N(COMe)CH 2 CH=CH 2 , N(COMe) CH 2 Ph, NHCOEt, KHCO-n-Pr, NHCO-i-Pr, NHCO-n-Bu, NHCO-s-Bu , NHCO-i-Bu, NHCO-t-Bu, NHCOC(Me)=CH 2 , NHCOCH 2 CH=CH 2 , NHCOCH(Me)CH=CH 2 , NHCOC(Me) 2 CH=CH 2 , NHCOCH 2 C≡CH, NHCOCH(Me)C≡CH, NHCOC(Me) 2 C≡CH, NHCO-(cyclopropyl), NHCOCH(Me)-n-Bu , NHCOPh, NHCOCH 2 Ph, NHCOCH 2 Cℓ, NHCOCH 2 Br, NHCOCHCℓ 2 , NHCOCCℓ 3 , NHCOCF 3 , NHCOCH 2 COMe, NHCOCH 2 CH 2 CH 2 CO 2 H, NHCOCH 2 CH 2 CH 2 CO 2 Me, NHCOCH 2 CH(Me)CH 2 CO 2 H, NHCOCH 2 CH(Me)CH 2 CO 2 Me, NHCOCH 2 CH(CF 3 )CH 2 CO 2 H, NHCOCH 2 CH(CF 3 )CH 2 CO 2 Me, N(SO 2 Me)COC(Me)=CH 2 , N(SO 2 Me)COCH 2 CH=CH 2 , N(SO 2 Me)COCH(Me)CH=CH 2 , N(SO 2 Me)COC(Me) 2 CH=CH 2 , N(SO 2 Me)COCH 2 C≡CH, N(SO 2 Me)COCH(Me)C≡CH, N(SO 2 Me)COC(Me) 2 C≡CH, N(SO 2 Me)CO-(cyclopropyl), N(SO 2 Me)COCH (Me)-n-Bu, N(SO 2 Me)COPh, N(SO 2 Me)COCH 2 Ph, N(SO 2 Me)COCH 2 Cℓ, N(SO 2 Me)COCH 2 Br, N(SO 2 Me)COCHCℓ 2 , N(SO 2 Me)COCCℓ 3 , N(SO 2 Me)COCF 3 , N(SO 2 Me) COCH 2 COMe, N(SO 2 Me)COCH 2 CH 2 CH 2 CO 2 H, N(SO 2 Me)COCH 2 CH 2 CH 2 CO 2 Me, N(SO 2 Me)COCH 2 CH(Me)CH 2 CO 2 H, N(SO 2 Me)COCH 2 CH(Me)CH 2 CO 2 Me, N(SO 2 Me)COCH 2 CH(CF 3 )CH 2 CO 2 H, N(SO 2 Me)COCH 2 CH(CF 3 )CH 2 CO 2 Me, N(SO 2 Et)COC(Me)=CH 2 , N(SO 2 Et)COCH 2 CH=CH 2 , N(SO 2 Et)COCH (Me)CH=CH 2 , N(SO 2 Et)COC(Me) 2 CH=CH 2 , N(SO 2 Et)COCH 2 C≡CH, N(SO 2 Et)COCH(Me)C≡CH, N(SO 2 Et)COC(Me) 2 C≡CH, N(SO 2 Et)CO-(cyclopropyl), N(SO 2 Et)COCH(Me)CH 2 CH 2 CH 2 Me, N(SO 2 Et)COPh, N(SO 2 Et)COCH 2 Ph, N(SO 2 Et)COCH 2 Cℓ, N(SO 2 Et)COCH 2 Br, N(SO 2 Et)COCHℓ 2 , N(SO 2 Et)COCCℓ 3 , N(SO 2 Et)COCF 3 , N(SO 2 Et)COCH 2 COMe, N(SO 2 Et)COCH 2 CH 2 CH 2 CO 2 H, N(SO 2 Et)COCH 2 CH 2 CH 2 CO 2 Me, N(SO 2 Et)COCH 2 CH(Me)CH 2 CO 2 H, N(SO 2 Et)COCH 2 C(Me)CH 2 CO 2 Me, N(SO 2 Et)COCH 2 CH(CF 3 )CH 2 CO 2 H, N(SO 2 Et)COCH 2 CH(CF 3 )CH 2 CO 2 Me, NHCOH, N(COH)Me, N(COH)Et, N(COH)-n-Pr, N(COH)-i-Pr, N(COH)-n-Bu, N(COH)-s-Bu, N(COH)-i-Bu, N(COH)-t-Bu, N(COH)C(Me)= CH 2 , N(COH)CH 2 CH=CH 2 , N(COH)CH(Me)CH =CH 2 , N(COH)C(Me) 2 CH=CH 2 , N(COH)CH 2 C≡CH, N(COH)CH(Me)C≡CH, N(COH)C(Me) 2 C≡CH, N(COH)-(cyclopropyl), N(COH)CH(Me)-n-Bu, N(COH)Ph, N(COH)CH 2 Ph, N(COH)CH 2 Cℓ, N(COH)CH 2 Br, N(COH)CHCℓ 2 , N(COH)CCℓ 3 , N(COH)CF 3 , N(COH)CH 2 COMe, N(COH)CH 2 CH 2 CH 2 CO 2 H, N(COH)CH 2 CH 2 CH 2 CO 2 Me, N(COH)CH 2 CH(Me)CH 2 CO 2 H, N(COH)CH 2 CH(Me)CH 2 CO 2 Me, N(COH)CH 2 CH(CF 3 )CH 2 CO 2 H, N(COH)CH 2 CH(CF 3 )CH 2 CO 2 Me, N(COH)SO 2 Me, N(COH)SO 2 Et, N(COH)SO 2 -n-Pr, N(COH)SO 2 -i-Pr, N(COH)SO 2 -n-Bu, N(COH)SO 2 -s-Bu, N(COH)SO 2 -i-Bu, N(COH)SO 2 -t-Bu , N(SO 2 CF 3 ) 2 , NHCO 2 Me, NHCO 2 Et, NHCO 2 -n-Pr, NHCO 2 -i-Pr , NHCO 2 -n-Bu, NHCO 2 -s-Bu, NHCO 2 -i-Bu, NHCO 2 -t-Bu, N (Me)CO 2 Me, N(Me)CO 2 Et, N(Me)CO 2 -n-Pt, N(Me)CO 2 -i-Pr, N(Me)CO 2 -n-Bu, N(Me)CO 2 -s-Bu, N(Me)CO 2 -i-Bu, N(Me)CO 2 -t-Bu, N(Et) CO 2 Me, N(Et)CO 2 Et, N(Et) CO 2 -n-Pr, N(Et)CO 2 -i-Pr, N(Et)CO 2 -n-Bu, N(Et)CO 2 -s-Bu, N(Et)CO 2 -i-Bu , N(Et)CO 2 -t-Bu, N(SO 2 Me)CO 2 Me, N(SO 2 Me)CO 2 Et, N(SO 2 Me)CO 2 -n-Pr, N(SO 2 Me)CO 2 -i-Pr, N(SO 2 Me)CO 2 -n-Bu, N(SO 2 Me)CO 2 -s-Bu, N(SO 2 Me)CO 2 -i-Bu, N(SO 2 Me)CO 2 -t-Bu, N(SO 2 Et)CO 2 Me, N(SO 2 Et)CO 2 Et, N(SO 2 Et)CO 2 -n-Pr, N(SO 2 Et)CO 2 -i-Pr, N(SO 2 Et)CO 2 -n-Bu, N(SO 2 Et)CO 2 -s-Bu, N(SO 2 Et)CO 2 -i-Bu, N(SO 2 Et)CO 2 -t-Bu, NHCO 2 CH 2 -t-Bu, NHCO 2 -n-Am, NHCO 2 -n-Hex, NHCO 2 CH 2 (CH 2 ) 6 Me, NHCO 2 CH 2 (CH 2 ) 8 Me, NHCO 2 CH 2 (CH 2 ) 14 Me, NHCO 2 CH 2 (CH 2 ) 16 Me, NHCO 2 CH=CH 2 , NHCO 2 CH 2 CH=CH 2 , NHCO 2 CH(Me)CH=CH 2 , NHCO 2 C(Me) 2 CH=CH 2 , NHCO 2 CH 2 C≡CH, NHCO 2 CH(Me)C≡CH, NHCO 2 C(Me) 2 C ≡CH, NHCO 2 CH 2 Ph, N(Me)CO 2 CH=CH 2 , N(Me)CO 2 CH 2 CH=CH 2 , N(Me)CO 2 CH(Me)CH=CH 2 , N(Me)CO 2 C(Me) 2 CH=CH 2 , N(Me)CO 2 CH 2 C≡CH, N(Me)CO 2 CH(Me)C≡CH, N(Me)CO 2 C(Me) 2 C≡CH, N(Me)CO 2 CH 2 Ph, NHCO 2 CH=CHPh, NHCO 2 CF 3 , NHCO 2 CH 2 CF 3 , NHCO 2 CH (F)CF 3 , NHCO 2 (CF 2 ) 3 CF 3 , NHCO 2 (CF 2 ) 5 CF 3 , NHCO 2 (CF 2 ) 7 CF 3 , NHCO 2 CCℓ 3 , NHCO 2 CHCℓ 2 , NHCO 2 CH 2 Cℓ, NHCO 2 CH 2 CCℓ 3 , NHCO 2 CH 2 CH 2 Cℓ, NHCO 2 CH 2 CH 2 CH 2 Cℓ, NHCO 2 CH 2 CH(Cℓ)Me, NHCO 2 CH 2 CH 2 OMe, NHCO 2 CH 2 CH 2 OEt, NHCO 2 Pb, N(Me)CO 2 Ph, NHCO 2 -(2-F-Ph), NHCO 2 -(3-F-Ph), NHCO 2 -(4-F-Ph), NHCO 2 -(2-Cℓ-Ph), NHCO 2 -(3-Cℓ-Ph), NHCO 2 -(4-Cℓ-Ph), NHCO 2 -(2-Br-Ph), NHCO 2 -(3-Br-Ph), NHCO 2 -(4-Br-Ph), NHCO 2 -(2-l-Ph), NHCO 2 -(3-l-Ph), NHCO 2 -(4-l-Ph), NHCO 2 -(2-Me-Ph), NHCO 2 -(3-Me-Ph), NHCO 2 -(4-Me-Ph), NHCO 2 -(2-MeO-Ph), NHCO 2 -(3-MeO-Ph), NHCO 2 -(4-MeO-Ph), NHCO 2 -(4-Et-Ph), NHCO 2 -(4-n-Pr-Ph), NHCO 2 -(4-i-Pr-Ph), NHCO 2 -(4-n-Bu-Ph), NHCO 2 -(4-s-Bu-Ph), NHCO 2 -(4-i-Bu-Ph), NHCO 2 -(4-t-Bu-Ph), NHCO 2 -(4-t-Am-Ph), NHCO 2 -(4-n-Hex-Ph), NHCO 2 -(2-NO 2 -Ph), NHCO 2 -(3-NO 2 -Ph), NHCO 2 -(4-NO 2 -Ph), NHCO 2 -(2-MeOCO-Ph), NHCO 2 -(3-MeOCO-Ph), NHCO 2 -(4-MeOCO-Ph), NHCO 2 -(2-CF 3 -Ph), NHCO 2 -(3-CF 3 -Ph), NHCO 2 -(4-CF 3 -Ph), NHCO 2 -(2-CF 3 O-Ph), NHCO 2 -(3-CF 3 O-Ph), NHCO 2 -(4-CF 3 O-Ph), NHCO 2 -(4-CF 3 CF 2 O-Ph), NHCO 2 -(3-MeCO-Ph), NHCO 2 -(3-HOCO-Ph), NHCO 2 -(4-HOCO-Ph), NHCO 2 -(2,4-di-NO 2 -Ph), NHCO 2 -(4-Cℓ-3-NO 2 -Ph), NHCO 2 -(2-Me-5-NO 2 -Ph), NHCO 2 -(4-Cℓ-3-HOCO-Ph), NHCO 2 -(2-MeCONH-Ph), NHCO 2 -(3-MeCONH-Ph), NHCO 2 -(4-MeCONH-Ph), NHCO 2 -(2-NO 2 -4-CF 3 -Ph), NHCO 2 -(3,5-di-CF 3 -Ph), NHCO 2 -(4-(2,2-dichlorocyclopropyl)-Ph), NHCO 2 -(3-NO 2 -4-t-Bu-Ph), NHCO 2 -(4-(1-bromoethyl)-Ph), NHCO 2 -(2,5-di-MeO-Ph), NHCO 2 -(4-dimethylamino-3-NO 2 -Ph), NHCO 2 -(4-Cℓ-3-CF 3 -Ph), NHCO 2 -(2,4-di-Me-3-NO 2 -Ph), NHCO 2 -(2,4-di-Cℓ-5-Me-Ph), NHCO 2 -(4-Cℓ-2,5-di-Me-Ph), NHCO 2 -(2-Cℓ-6-Me-Ph), NHCO 2 -(3-Cℓ-4-MeO-Ph), NHCO 2 -(3-Cℓ-2-Me-Ph), NHCO 2 -(2-Cℓ-5-CF 3 -Ph), NHCO 2 -(2-Cℓ-4-C F 3 -Ph), NHCO 2 -(2-CN-Ph), NHCO 2 -(3-CN-Ph), NHCO 2 -(4-CN-Ph), NHCO 2 -(5-F-2-Me-Ph), NHCO 2 -(5-C ℓ -2-MeO-Ph), NHCO 2 -(2,4-di-i-Pr-Ph), NHCO 2 -(6-MeO-3-Me-Ph), NHCO 2 -(2,4-di-MeO-Ph), NHCO 2 -(3,4-di-MeO-Ph), NHCO 2 -(3,5-di-MeO-Ph), NHCO 2 -(2, 5-di-MeO-Ph), NHCO 2 -(2,6-di-MeO-Ph), NHCO 2 -(2, 3-di-MeO-Ph), NHCO 2 -(2,4-di-Cℓ-Ph), NHCO 2 -(3,4-di-Cℓ-Ph), NHCO 2 -(3,5-di-Cℓ-Ph), NHCO 2 -(2,5-di-Cℓ-Ph), NHCO 2 -(2,6-di-Cℓ-Ph), NHCO 2 -(2,3-di-Cℓ-Ph), NHCO 2 -(2,4,6-tri-Cℓ-Ph), NHCO 2 -(2,4-di-F-Ph), NHCO 2 -(3,4-di-F-Ph), NHCO 2 -(3, 5-d i-F-Ph), NHCO 2 -(2,5-di-F-Ph), NHCO 2 -(2,6-di-F-Ph), NHCO 2 -(2,5-di-Br-Ph), NHCO 2 -(3,4-di-Br-Ph), NHCO 2 -(2-Cℓ-4-F-Ph), NHCO 2 -(3-Cℓ-4-F-Ph), NHCO 2 -(pentafluoro-Ph), NHCO 2 -(pentamethyl-Ph), NHCO 2 -(2,4,6-tri-Me-Ph), NHCO 2 -(2,4,6-tri-i-Pr-Ph), NHCO 2 -(2,3,5,6-tetra-Me-Ph), NHCO 2 -(2,4-di-Me-Ph) , NHCO 2 -(3,4-di-Me-Ph), NHCO 2 -(3,5-di-Me-Ph) , NHCO 2 -(2,5-di-Me-Ph), NHCO 2 -(2,6-di-Me-Ph), NHCO 2 -(2,3-di-Me-Ph), NHCO 2 CH 2 -(2-F-Ph) , NHCO 2 CH 2 -(3-F-Ph), NHCO 2 CH 2 -(4-F-ph), NHCO 2 CH 2 -(2-Cℓ-Ph), NHCO 2 CH 2 -(3-Cℓ-Ph), NHCO 2 CH 2 -(4-Cℓ-Ph), NHCO 2 CH 2 -(2-Br-Ph), NHCO 2 CH 2 -(3-Br-Ph), NHCO 2 CH 2 -(4-Br-Ph) , NHCO 2 CH 2 -(2-l-Ph), NHCO 2 CH 2 -(3-l-Ph) , NHCO 2 CH 2 -(4-l-Ph), NHCO 2 CH 2 -(2-Me-Ph), NHCO 2 CH 2 -(3-Me-Ph), NHCO 2 CH 2 -(4-Me-Ph), NHCO 2 CH 2 -(2-MeO-Ph), NHCO 2 CH 2 -(3-MeO-Ph), NHCO 2 CH 2 -(4-MeO-Pb), NHCO 2 CH 2 -(4-Et-Ph), NHCO 2 CH 2 -(4-n-Pr-Ph), NHCO 2 CH 2 -(4-i-Pr-Ph), NHCO 2 CH 2 -(4-n-Bu-Ph), NHCO 2 CH 2 -(4-s-Bu-Ph), NHCO 2 CH 2 -(4-i-Bu-Ph), NHCO 2 CH 2 -(4-t-Bu-Ph), NHCO 2 CH 2 -(4-t-Am-Ph), NHCO 2 CH 2 -(4-n-Hex-Ph), NHCO 2 CH 2 -(2-NO 2 -Ph), NHCO 2 CH 2 -(3-NO 2 -Ph), NHCO 2 CH 2 -(4-NO 2 -Ph), NHCO 2 CH 2 -(2-MeOCO-Ph), NHCO 2 CH 2 -(3-MeOCO-Ph), NHCO 2 CH 2 -(3,4-di-M e-Ph), NHCO 2 CH 2 -(2,4-di-Me-Ph), NHCO 2 CH 2 -(4-MeOCO-Ph), NHCO 2 CH 2 -(2-CF 3 -Ph), NHCO 2 CH 2 -(3-CF 3 -Ph), NHCO 2 CH 2 -(4-CF 3 -Ph), NHCO 2 CH 2 -(2-CF 3 O-Ph), NHCO 2 CH 2 -(3-CF 3 O-Ph), NHCO 2 CH 2 -(4-CF 3 O-Ph), NHCO 2 CH 2 -(4-CF 3 CF 2 O-Ph), NHCO 2 CH 2 -(3-MeCO-Ph), NHCO 2 CH 2 -(3-HOCO-Ph), NHCO 2 CH 2 -(4-HOCO-Ph), NH(CO)SMe, NH(CO)SEt, NHCOCO 2 Me, NHCOCO 2 Et, NHCOCO 2 -n-Pr, NHCOCO 2 -i-Pr, NHCOCO 2 -n-Bu, NHCOCO 2 -s-Bu, NHCOCO 2 -i-Bu, NHCOCO 2 -t-Bu, NHCOCO 2 CH 2 Ph, NHCOCO 2 Ph, N(Me)COCO 2 Me, N(Me)COCO 2 Et, N(Me)COCO 2 -n-Pt, N(Me) COCO 2 -i-Pr, N(Me)COCO 2 -n-Bu, N(Me)COCO 2 -s-Bu, N(Me)COCO 2 -i-Bu, N(Me)COCO 2 -t-Bu, N(Me)COCO 2 CH 2 Ph, N(Me)COCO 2 Ph, N(Et)COCO 2 Me, N(Et)COCO 2 Et, N(Et)COCO 2 -n-Pr, N(Et)COCO 2 -i-Pr, N(Et)COCO 2 -n-Bu, N(Et)COCO 2 -s-Bu, N(Et)COCO 2 -i-Bu, N(Et)COCO 2 -t-Bu, M(Et) COCO 2 CH 2 Ph, N(Et)COCO 2 Ph, NHSCCℓ 3 , NHS(O)CCℓ 3 , NHS(O)Me, NHS(O)Et, NHS(O)-n-Pt, NHS(O)-i-Pr , NHS(O)-n-Bu, NHS(O)-s-Bu, NHS(O)-i-Bu, NHS(O)-t-Bu, NHS(O)CH 2 Ph, NHS(O)Ph, N(Me)SCCℓ 3 , N(Me)S(O)CCℓ 3 , N(Me)S(O)Me, N(Me)S(O)Et, N(Me)S(O)-n-Pr, N(Me)S(O)-i-Pr, N(Me)S(O)-n-Bu, N(Me)S(O)-s-Bu, N(Me)S(O)-i-Bu, N(Me)S(O)-t-Bu, N(Me)S(O)CH 2 Ph, N(Me)S(O)Ph, N(Et)SCCℓ 3 , N(Et)S(O)CCℓ 3 , N(Et)S(O)Me, N(Et)S(O)Et, N(Et)S(O)-n-Pr, N(Et)S(O)-i-Pr, N(Et)S(O)-n-Bu, N(Et)S (O)-s-Bu, N(Et)S(O)-i-Bu, N(Et)S(O)-t-Bu, N(Et)S(O)CH 2 Ph, N(Et)S(O)Ph, NHSO 2 NH 2 , NHSO 2 N(Me) 2 , NHSO 2 NHMe, NHSO 2 NH Et, NHSO 2 NH-n-Pr, NHSO 2 NH-i-Pr, NHSO 2 NH-n-Bu, NHSO 2 NHPh, NHSO 2 NH-(2-Cℓ-Ph), NHSO 2 NH-(3-Cℓ-Ph), NHSO 2 NH-(4-Cℓ-Ph), NHSO 2 NHCH 2 Ph, NHCSNH 2 , NHCON(Me) 2 , NHCON(Me)OMe, NHCONHMe, NHCONHEt, NHCONH-n-Pr, NHCONH-i-Pr, NHCONH-n-Bu, NHCONH-s-Bu, NHCONH-i-Bu, NHCONH-t-Bu, NHCONHCH 2 Ph, NHCONHPh, NHCON(Me)Ph, NHCON(OMe)Ph, N=C(OMe)N(Me) 2 , N=C(SMe)N(Me) 2 , NHCONHSO 2 Me, NHCONHSO 2 Et, NHCONHSO 2 -n-Pr, NHCONHSO 2 -i-Pr, NHCONHSO 2 -n-Bu, NHCONHSO 2 -s-Bu, NHCONHSO 2 -i-Bu, NHCONHSO 2 -t-Bu, NHCONHSO 2 CH 2 Ph, NHCONHSO 2 Ph, NHCONHSO 2 CF 3 , NHCSN(Me) 2 , NHCSN(Me)OMe, NHCSNHMe, NHCSNHEt, NHCSNH-n-Pr, NHCSNH-i-Pr, NHCSNH-n-Bu, NHCSNH-s-Bu, NHCSNH-i-Bu, NHCSNH-t-Bu, NHCSNHCH 2 Ph, NHCSNHPh, NHCONHCOMe, NHCONHCOEt, NHCONHCO-(2,6-di-Cℓ-Ph), NHCONHCO-(2,6-di-F-Ph), NHCSNHCO-(2,6-di-Cℓ-Ph), NHCSNHCO-(2, 6-ddi-F-Ph), N=CHN(Me) 2 , N=CHN(Et) 2 , N=CHN(Et)Me, N=CHN(Et)Ph, N=C(OMe)Ph, N=C(Me)Ph, -Q30, -(4-Me-Q30), -(4-CF 3 -Q30), -(4-Ph-Q30), -Q31, -Q32, -(4-Me-Q32), -(4-Me-Q33), -(4-H-Q33), - Q34, -(2,6-di-Me-Q34), -Q35, -(2,6-di-Me-Q35), -Q36, -(3-Me-Q36), -Q37, -Q38, -(3-Me-Q38), -(4-Me-Q38), -(5-Me-Q38), -Q39, -(3-Me-Q39), -(4-Me-Q39), -(5-Me-Q39), -(6 - Me-Q39), -(6-Me-Q40), -(6-H-Q40), -(6,3-di-Me-Q40), -(6,4-di-Me-Me-Q40), -(6,5-di-Me-Q40), -Q41, -Q42, -(2,5-di-Me-Q42), -Q43, -Q44, -(3,4-di-Me-Q44), -(3,4-di-Cℓ-Q44), -Q45, -Q46, -(4-H-Q47), -(4-Me-Q47), -(4-CH 2 CO 2 Me-Q47),-(4-CO 2 Me-Q47), NH-(4,6-di-MeO-Q14), NH-(4,6-di-Me-Q14), CONH-(4,6-di-MeO-Q14), CONH-(4,6-di-Me-Q14), NH-(5-CF 3 -3-Cℓ-Q1), NHP(O)(OMe) 2 , NHP(O)(OEt) 2 , NHP(O)(OEt)S-n-Pr, NHP(O)(OEt)SPh, NHP(O)(OEt)O-n-Pr, NHP(O)(O-i-Pr) 2 , NHP(O)(O-n-Pr) 2 , NHP(S)(OMe) 2 , NHP(S)(OEt) 2 , NHP(S)(OEt)S-n-Pr, NHP(S)(OEI)SPh, NHP(S)(OEt)O-n-Pr, NHP(S)(O-i-Pr) 2 , NHP(S)(O-n-Pr) 2 , NHP(O)(OMe)Me, NH P(O)(OEt)Me, NHP(O)(OEt)Ph, NHP(O)(O-i-Pr)Me, NHP(O)(O-n-Pr)Me, NHP (S)(OMe)Me, NHP (S)(OEt)Me, NHP (S)(OEt) Ph, NHP (S)(O-i-Pr)Me, NHP (S)(O-n-Pr)Me, NHP (O)(OMe)OH, NHP (O)(OEt)OH, NHCH 2 CO 2 H, NHCH 2 CO 2 Me, NHCH 2 CO 2 Et, NHCH 2 CO 2 -n-Pr, NHCH 2 CO 2 -i-Pr, NHCH 2 CO 2 -n-Bu, NHCH 2 CO 2 -s-Bu, NHCH 2 CO 2 -i-Bu, NHCH 2 CO 2 -t-Bu, NHCH 2 CO 2 -t-Am , NHCH 2 CO 2 -n-Am, NHCH 2 CO 2 -n-Hex, NHCH 2 CO 2 CH 2 (CH 2 ) 6 Me, NHCH 2 CO 2 CH 2 Ph, NHCH 2 CO 2 Ph, NHCH 2 CO 2 CH 2 CO 2 Me, NHCH 2 CO 2 CH 2 CO 2 Et, NHCH 2 CO 2 CH(Me)CO 2 Me, NHCH 2 CO 2 CH(Me)CO 2 Et, N(Me)CH 2 CO 2 Me, N(Me)CH 2 CO 2 Et, N(Et)CH 2 CO 2 Me, N(Et)CH 2 CO 2 Et, N(COMe)CH 2 CO 2 Me, N(COMe)CH 2 CO 2 Et, N(COPh)CH 2 CO 2 Me, N(COPh)CH 2 CO 2 Et, NHCH(Me)CO 2 H, NHCH(Me)CO 2 Me, NHCH(Me)CO 2 Et, NHCH(Me)CO 2 -n-Pr, NHCH(Me)CO 2 -i-Pr, NHCH(Me)CO 2 -n-Bu, NHCH(Me)CO 2 -s-Bu, NHCH(Me)CO 2 -i-Bu, NHCH(Me)CO 2 -t-Bu, NHCH(Me)CO 2 -t-Am, NHCH(Me)CO 2 -n-Am, NHCH(Me)CO 2 -n-Hex, NHCH(Me)CO 2 CH 2 (CH 2 ) 6 Me, NHCH(Me)CO 2 CH 2 Ph, NHCH(Me)CO 2 Ph, NHCH(Me)CO 2 CH 2 CO 2 Me, NHCH(Me)CO 2 CH 2 CO 2 Et, NHCH(Me)CO 2 CH(Me)CO 2 Me, NHCH(Me)CO 2 CH(Me)CO 2 Et, N(Me)CH(Me)CO 2 Me, N(Me)CH (Me)CO 2 Et, N(Et)CH(Me)CO 2 Me, N(Et)CH(Me)CO 2 Et, N(COMe)CH(Me)CO 2 Me, N(COMe)CH(Me)CO 2 Et, N(COPh)CH(Me)CO 2 Me, N(COPh)CH(Me)CO 2 Et, NHCH(Et)CO 2 H, NHCH(Et)CO 2 Me, NHCH(Et)CO 2 Et, NHCH(Et)CO 2 -n-Pr, NHCH(Et)CO 2 -i-Pr, NHCH(Et)CO 2 -n-Bu, NHCH(Et)CO 2 -s-Bu, NHCH(Et)CO 2 -i-Bu, NHCH(Et)CO 2 -t-Bu, NHCH(Et)CO 2 -t-Am, NHCH(Et)CO 2 -n-Am, NHCH(Et)CO 2 -n-Hex, NHCH(Et)CO 2 CH 2 (CH 2 ) 6 Me, NHCH(Et)CO 2 CH 2 Ph, NHCH(Et)CO 2 Ph, NHCH(CH 2 OMe)CO 2 H, NHCH(CH 2 OMe)CO 2 Me, NHCH(CH 2 OMe)CO 2 Et, NHCH(CH 2 OMe)CO 2 -n-Pr, NHCH(CH 2 OMe)CO 2 -i-Pr, NHCH(CH 2 OMe)CO 2 -n-Bu, NHCH(CH 2 OMe)CO 2 -s-Bu, NHCH(CH 2 OMe)CO 2 -i-Bu, NHCH(CH 2 OMe)CO 2 -t-Bu, NHCH(CH 2 OMe)CO 2 -t-Am, NHCH(CH 2 OMe)CO 2 -n-Am, NHCH(CH 2 OMe)CO 2 -n-Hex, NHCH(CH 2 OMe)CO 2 CH 2 (CH 2 ) 6 Me, NHCH(CH 2 OMe)CO 2 CH 2 Ph, NHCH(CH 2 OMe)CO 2 Ph, NHCH(CH 2 OEt)CO 2 H, NHCH(CH 2 OEt)CO 2 Me, NHCH(CH 2 OEt)CO 2 Et, NHCH(CH 2 OEt)CO 2 -n-Pr, NHCH(CH 2 OEt)CO 2 -i-Pr, NHCH(CH 2 OEt)CO 2 -n-Bu, NHCH(CH 2 OEt)CO 2 -s-Bu, NHCH(CH 2 OEt)CO 2 -i-Bu, NHCH(CH 2 OEt)CO 2 -t-Bu, NHCH(CH 2 OEt) CO 2 -t-Am, NHCH(CH 2 OEt)CO 2 -n-Am, NHCH(CH 2 OEt)CO 2 -n-Hex, NHCH(CH 2 OEt)CO 2 CH 2 (CH 2 ) 6 Me, NHCH(CH 2 OEt)CO 2 CH 2 Ph, NHCH(CH 2 OEt)CO 2 Ph, NHCH(SMe)CO 2 H, NHCH(SMe)CO 2 Me, NHCH(SMe)CO 2 Et, NHCH(SMe)CO 2 -n-Pr, NHCH(SMe)CO 2 -i-Pr, NHCH(SMe)CO 2 -n-Bu, NHCH(SMe)CO 2 -s-Bu, NHCH(SMe)CO 2 -i-Bu, NHCH(SMe)CO 2 -t-Bu, NHCH(SMe)CO 2 -t-Am , NHCH(SMe)CO 2 -n-Am, NHCH(SMe)CO 2 -n-Hex, NHCH(SMe)CO 2 CH 2 (CH 2 ) 6 Me, NHCH(SMe)CO 2 CH 2 Ph, NHCH(SMe)CO 2 Ph, NHCH(i-Pr)CO 2 Me, NHCH(i-Pr)CO 2 Et, NHCH(i-Pr)CO 2 -n-Pr, NHCH(i-Pr)CO 2 -i-Pr, NHCH(n-Pr)CO 2 Me, NHCH(n-Pr)CO 2 Et, NHCH(n-Pr)CO 2 -n-Pr, NHCH(n-Pr)CO 2 -i-Pr , NHCH(Ph)CO 2 Me, NHCH(Ph)CO 2 Et, NHCH(Ph)CO 2 -n-Pr, NHCH(Ph)CO 2 -i-Pr, NHCH 2 CONH 2 , NHCH 2 CONHMe, NHCH 2 CONHEt, NHCH 2 CONH-n-Pr, NHCH 2 CONH-i-Pr, NHCH 2 CONH-n-Bu, NHCH 2 CONH-s-Bu, NHCH 2 CONH-i-Bu, NHCH 2 CONH-t-Bu, NHCH 2 CONH-t-Am, NHCH 2 CONH-n-Am, NHCH 2 CONH-n-Hex, NHCH 2 CONHCH 2 (CH 2 ) 6 Me, NHCH 2 CONHCH 2 Ph, NHCH 2 CONHPh, NHCH 2 CONHCH 2 CO 2 Me, NHCH 2 CONHCH 2 CO 2 Et, NHCH 2 CONHCH(Me)CO 2 Me, NHCH 2 CONHCH(Me)CO 2 Et, N(Me)CH 2 CONHMe, N(Me)CH 2 CONHEt, N(Et)CH 2 CONHMe, N(Et)CH 2 CONHEt, N(COMe)CH 2 CONHMe, N(COMe)CH 2 CONHEt, N(COPh)CH 2 CONHMe, N(COPh)CH 2 CONHEt, NHCH(Me)CONH 2 , NHCH(Me)CONHMe, NHCH(Me)CONHEt, NHCH(Me)CONH-n-Pr, NHCH(Me)CONH-i-Pr, NHCH(Me)CONH-n-Bu, NHCH(Me)CONH-s-Bu , NHCH(Me)CONH-i-Bu, NHCH(Me)CONH-t-Bu, NHCH(Me)CONH-t-Am, NHCH(Me)CONH-n-Am, NHCH(Me)CONH-n-Hex, NHCH(Me)CONHCH 2 (CH 2 ) 6 Me, NHCH(Me)CONHCH 2 Ph, NHCH(Me)CONHPh, NHCH(Me)CONHCH 2 CO 2 Me, NHCH(Me)CONHCH 2 CO 2 Et, NHCH(Me)CONHCH(Me)CO 2 Me, NHCH(Me)CONHCH (Me)CO 2 Et, NHCH(Me)CONHCH(Me)Ph, N(Me)CH(He)CONHMe, N(Me)CH(Me)CONHEt, N(Et)CH(Me)CONHMe, N(Et)CH(Me)CONHEt, N(COMe)CH(Me)CONHMe, N(COMe)CH (Me)CONHEt, N(COPh)CH(Me)CONHMe, N(COPh)CH(Me)CONHEt, NHCH(Et)CONH 2 , NHCH(Et)CONHMe, NHCH(Et)CONHEt, NHCH(Et)CONH-n-Pr, NHCH(Et)CONH-i-Pr, NHCH(Et)CONH-n-Bu, NHCH(Et)CONH-s-Bu, NHCH(Et)CONH-i-Bu, NHCH(Et)CONH-t-Bu, NHCH(Et)CONH-t-Am, NHCH(Et)CONH-n-Am, NHCH(Et)CONH-n-Hex, NHCH(Et)CONHCH 2 (CH 2 ) 6 Me, NHCH(Et)CONHCH 2 Ph, NHCH(Et)CONHPh, NHCH(CH 2 OMe)CONH 2 , NHCH(CH 2 OMe)CONHMe, NHCH(CH 2 OMe)CONHEt, NHCH(CH 2 OMe)CONH-n-Pr, NHCH(CH 2 OMe)CONH-i-Pr , NHCH(CH 2 OMe)CONH-n-Bu, NHCH(CH 2 OMe)CONH-s-Bu, NHCH(CH 2 OMe)CONH-i-Bu, NHCH(CH 2 OMe)CONH-t-Bu, NHCH(CH 2 OMe)CONH-t-Am, NHCH(CH 2 OMe)CONH-n-Am, NHCH(CH 2 OMe)CONH-n-Hex, NHCH(CH 2 OMe)CONHCH 2 (CH 2 ) 6 Me, NHCH(CH 2 OMe)CONHCH 2 Ph, NHCH(CH 2 OMe)CONHPh, NHCH(CH 2 OEt)CONH 2 , NHCH(CH 2 OEt)CONHMe, NHCH(CH 2 OEt)CONHEt, NHCH(CH 2 OEt)CONH-n-Pr, NHCH(CH 2 OEt)CONH-i-Pr, NHCH(CH 2 OEt)CONH-n-Bu, NHCH(CH 2 OEt)CONH-s-Bu, NHCH(CH 2 OEt)CONH-i-Bu, NHCH(CH 2 OEt)CONH-t-Bu , NHCH(CH 2 OEt)CONH-t-Am, NHCH(CH 2 OEt)CONH-n-Am , NHCH(CH 2 OEt)CONH-n-Hex, NHCH(CH 2 OEt)CONHCH 2 (CH 2 ) 6 Me, NHCH(CH 2 OEt)CONHCH 2 Ph, NHCH(CH 2 OEt)CONHPh, NHCH(SMe)CONH 2 , NHCH(SMe)CONHMe, NHCH(SMe)CONHEt, NHCH(SMe)CONH-n-Pt, NHCH(SMe)CONH-i-Pr, NHCH(SMe)CONH-n-Bu, NHCH(SMe)CONH-s-Bu, NHCH(SMe)CONH-i-Bu, NHCH(SMe)CONH-t-Bu, NHCH(SMe)CONH-t-Am, NHCH(SMe)CONH-n-Am, NHCH(SMe)CONH-n-Hex, NHCH(SMe)CONHCH 2 (CH 2 ) 6 Me, NHCH(SMe)CONHCH 2 Ph, NHCH(SMe)CONHPh, NHCH(i-Pr)CONHMe, NHCH(i-Pr)CONHEt, NHCH(i-Pr)CONH-n-Pr, NHCH(i-Pr)CONH-i-Pr, NHCH(n-Pr)CONHMe, NHCH(n-Pr)CONHEt, NHCH(n-Pr)CONH-n-Pr, NHCH(n-Pr)CONH-i-Pr, NHCH(Ph)CONHMe, NHCH(Ph)CONHEt, NHCH(Ph)CONH-n-Pr, NHCH(Ph)CONH-i-Pr, NHCH 2 CN, NHCH(Me)CN, NHC(Me) 2 CN, N(Me)CH 2 CN, N(Me)CH(Me)CN, N(Me)C(Me) 2 CN, NHCH 2 CH 2 CO 2 Me, NHCH(Me)CH 2 CO 2 Me, NHCH 2 CH 2 CH 2 CO 2 Me, NHCH 2 CH 2 CH 2 CH 2 CO 2 Me, NHCH 2 CH 2 CO 2 Et, NHCH(Me)CH 2 CO 2 Et, NHCH 2 CH 2 CH 2 CO 2 Et, NHCH 2 CH 2 CH 2 CH 2 CO 2 Et, NHCH 2 P(O)(OMe) 2 , NHCH 2 P(O)(OEt) 2 , NHCH 2 P(O)(O-i-Pr) 2 , NHCH 2 P(O)(O-n-Pr) 2 , NHCH 2 P(S)(OMe) 2 , NHCH 2 P (S)(OEt) 2 , NHCH 2 P(S)(O-i-Pr) 2 , NHCH 2 P(S)(O-n-Pr) 2 , NHCH 2 P(O)(OMe)Me, NHCH 2 P(O)(OEt)Me, NHCH 2 P(O)(O-i-Pr)Me, NHCH 2 P(O)(O-n-Pr)Me, NHCH 2 P (S)(OMe)Me, NHCH 2 P(S)(OEt)Me, NHCH 2 P(S)(O-i-Pr)Me, NHCH 2 P(S)(O-n-Pr)Me, NHCH 2 P(O)(OMe)OH, NHCH 2 P(O)(OEt)OH, NHCH 2 P(O)(OH) 2 , NHCH 2 CH 2 P(O)(OMe) 2 , NHCH 2 CH 2 P(O)(OEt) 2 , NHCH 2 CH 2 P(O)(O-i-Pr) 2 , NHCH 2 CH 2 P(O)(O-n-Pr) 2 , NHCH 2 CH 2 P (S)(OMe) 2 , NHCH 2 CH 2 P (S)(OEt) 2 , NHCH 2 CH 2 P(S)(O-i-Pr) 2 , NHCH 2 CH 2 P(S)(O-n-r) 2 , NHCH 2 CH 2 P(O)(OMe)Me, NHCH 2 CH 2 P (O)(OEt)Me, NHCH 2 CH 2 P (O)(O-i-Pr)Me, NHCH 2 CH 2 P (O)(O-n-Pr)Me, NHCH 2 CH 2 P (S)(OMe)Me, NHCH 2 CH 2 P (S)(OEt)Me, NHCH 2 CH 2 P (S)(O-i-Pr)Me, NHCH 2 CH 2 P (S)(O-n-Pr)Me, NHCH 2 CH 2 P (O)(OMe)OH, NHCH 2 CH 2 P(O)(OEt)OH, NHCH 2 CH 2 P(O)(OH) 2 , NHCH(P (O)(OMe) 2 ) 2 , NHCH(P(O)(OEt) 2 ) 2 , NHCH(P(O)(O-i-Pr) 2 ) 2 , NHCH(P (O)(O-n-Pr) 2 ) 2 , NHCH(P(O)(OH) 2 ) 2 , NHCH (P (O)(OMe) 2 )(P(O)(OH) 2 ), NHCH(P(O)(OEt) 2 )(P(O)(OH) 2 ), NHCH(P(O)(O-i-Pr) 2 )(P (O)(OH) 2 ), NHCH(P(O)(O-n-Pr) 2 )(P (O)(OH) 2 ), NHC(Me)(P(O)(OMe) 2 ) 2 , NHC(Me)(P (O)(OEt) 2 ) 2 , NHC(Me)(P(O)(O-i-Pr) 2 ) 2 , NHC(Me)(P (O)(O-n-Pr) 2 ) 2 , NHC(Me)(P(O)(OH) 2 ) 2 , NHC(Me)(P(O)(OMe) 2 )(P(O)(OH) 2 ), NHC(Me)(P(O)(OEt) 2 (P(O)(OH) 2 ), NHC(Me)(P(O)(O-i-Pr) 2 (P(O)(OH) 2 ), NHC(Me)(P(O)(O-n-Pr) 2 )(P(O)(OH) 2 ), N(SO 2 Me)CH 2 CO 2 H, N(SO 2 Me)CH 2 CO 2 Me, N(SO 2 Me)CH 2 CO 2 Et, N(SO 2 Me)CH 2 CO 2 -n-Pr, N(SO 2 Me)CH 2 CO 2 -i-Pr, N(SO 2 Me)CH 2 CO 2 -n-Bu, N(SO 2 Me)CH 2 CO 2 -s-Bu, N(SO 2 Me)CH 2 CO 2 -i-Bu, N(SO 2 Me)CH 2 CO 2 -t-Bu, N(SO 2 Me)CH 2 CO 2 -t-Am, N(SO 2 Me)CH 2 CO 2 -n-Am, N(SO 2 Me)CH 2 CO 2 -n-Hex, N(SO 2 Me)CH 2 CO 2 CH 2 (CH 2 ) 6 Me, N (SO 2 Me)CH 2 CO 2 CH 2 Ph, N(SO 2 Me)CH 2 CO 2 Ph, N(SO 2 Me)CH 2 CONH 2 , N(SO 2 Me)CH 2 CONHMe, N(SO 2 Me)CH 2 CONHEt, N(SO 2 Me)CH 2 CONH-n-Pr, N(SO 2 Me)CH 2 CONH-i-Pr, N(SO 2 Me)CH 2 CONH-n-Bu, N(SO 2 Me)CH 2 CONH-s-Bu, N(SO 2 Me)CH 2 CONH-i-Bu, N(SO 2 Me)CH 2 CONH-t-Bu, N(SO 2 Me)CH 2 CONH-t-Am, N(SO 2 Me)CH 2 CONH-n-Am, N(SO 2 Me) CH 2 CONH-n-Hex, N(SO 2 Me)CH 2 CONHCH 2 (CH 2 ) 6 Me, N(SO 2 Me)CH 2 CONHCH 2 Ph, N(SO 2 Me)CH 2 CONHPh, N(SO 2 Me)CH(Me)CO 2 H, N(SO 2 Me)CH(Me)CO 2 Me, N(SO 2 Me)CH(Me)CO 2 Et, N(SO 2 Me) CH(Me)CO 2 -n-Pr, N(SO 2 Me)CH(Me)CO 2 -i-Pr, N(SO 2 Me)CH(Me)CO 2 -n-Bu, N(SO 2 Me)CH(Me)CO 2 -s-Bu, N(SO 2 Me)CH(Me)CO 2 -i-Bu, N(SO 2 Me)CH(Me)CO 2 -t-Bu, N(SO 2 Me)CH(Me)CO 2 -1-Am, N(SO 2 Me)CH(Me)CO 2 -n-Am, N(SO 2 Me)CH(Me)CO 2 -n-Hex, N(SO 2 Me)CH(Me)CO 2 CH 2 (CH 2 ) 6 Me, N(SO 2 Me)CH(Me)CO 2 CH 2 Ph, N(SO 2 Me)CH(Me)CO 2 Ph, N(SO 2 Me)CH(Me)CONH 2 , N(SO 2 Me)CH(Me)CONHMe, N(SO 2 Me)CH(Me)CONHEt, N(SO 2 Me)CH(Me)CONH-n-Pr, N(SO 2 Me)CH(Me)CONH-i-Pr, N(SO 2 Me)CH(Me)CONH-n-Bu, N(SO 2 Me)CH(Me)CONH-s-Bu, N(SO 2 Me)CH(Me) CONH-i-Bu, N(SO 2 Me)CH(Me)CONH-t-Bu, N(SO 2 Me)CH(Me)CONH-t-Am, N(SO 2 Me)CH(Me)CONH-n-Am, N(SO 2 Me)CH(Me)CONH-n-Hex, N(SO 2 Me)CH(Me)CONHCH 2 (CH 2 ) 6 Me, N(SO 2 Me)CH(Me)CONHCH 2 Ph, N(SO 2 Me)CH(Me) CONHPh, N(SO 2 Et)CH 2 CO 2 H, N(SO 2 Et)CH 2 CO 2 Me, N(SO 2 Et)CH 2 CO 2 Et, N(SO 2 Et)CH 2 CO 2 -n-Pr, N(SO 2 Et)CH 2 CO 2 -i-Pr, N(SO 2 Et)CH 2 CO 2 -n-Bu, N(SO 2 Et)CH 2 CO 2 -s-Bu, N(SO 2 Et)CH 2 CO 2 -i-Bu, N(SO 2 Et)CH 2 CO 2 -t-Bu, N(SO 2 Et)CH 2 CO 2 -t-Am, N(SO 2 Et)CH 2 CO 2 -n-Am, N(SO 2 Et)CH 2 CO 2 -n-Hex, N (SO 2 Et)CH 2 CO 2 CH 2 (CH 2 ) 6 Me, N(SO 2 Et)CH 2 CO 2 CH 2 Ph, N(SO 2 Et)CH 2 CO 2 Ph, N(SO 2 Et)CH 2 CONH 2 , N(SO 2 Et)CH 2 CONHMe, N(SO 2 Et)CH 2 CONHEt, N(SO 2 Et)CH 2 CONH-n-Pr, N(SO 2 Et)CH 2 CONH-i-Pr, N(SO 2 Et)CH 2 CONH-n-Bu, N(SO 2 Et)CH 2 CONH-s-Bu, N(SO 2 Et)CH 2 CONH-i-Bu , N(SO 2 Et)CH 2 CONH-t-Bu, N(SO 2 Et)CH 2 CONH-t-Am, N(SO 2 Et)CH 2 CONH-n-Am, N(SO 2 Et)CH 2 CONH-n-Hex, N(SO 2 Et)CH 2 CONHCH 2 (CH 2 ) 6 Me, N(SO 2 Et)CH 2 CONHCH 2 Ph, N(SO 2 Et)CH 2 CONHPh, N(SO 2 Et)CH(Me)CO 2 H, N(SO 2 Et) CH (Me)CO 2 Me, N(SO 2 Et) CH (Me)CO 2 Et, N(SO 2 Et)CH (Me)CO 2 -n-Pr, N(SO 2 Et)CH(Me)CO 2 -i-Pr, N(SO 2 Et)CH(Me)CO 2 -n-Bu, N(SO 2 Et)CH(Me)CO 2 -s-Bu, N(SO 2 Et)CH(Me)CO 2 -i-Bu, N(SO 2 Et)CH(Me)CO 2 -t-Bu, N(SO 2 Et)CH(Me)CO 2 -t-Am, N(SO 2 Et)CH(Me)CO 2 -n-Am, N(SO 2 Et)CH(Me)CO 2 -n-Hex, N(SO 2 Et)CH(Me)CO 2 CH 2 (CH 2 ) 6 Me, N(SO 2 Et)CH(Me)CO 2 CH 2 Ph, N(SO 2 Et)CH(Me)CO 2 Ph, N(SO 2 Et)CH(Me)CONH 2 , N(SO 2 Et) CH(Me)CONHMe, N(SO 2 Et)CH(Me)CONHEt, N(SO 2 Et)CH(Me)CONH-n-Pt, N(SO 2 Et) CH(Me)CONH-i-Pr, N(SO 2 Et)CH(Me)CONH-n-Bu, N(SO 2 Et)CH(Me)CONH-s-Bu, N(SO 2 Et )CH (Me)CONH-i-Bu, N(SO 2 Et)CH(Me)CONH-t-Bu , N(SO 2 Et)CH(Me)CONH-t-Am, N(SO 2 Et)CH(Me)CONH-n-Am, N(SO 2 Et)CH(Me)CONH-n-Hex, N(SO 2 Et)CH(Me)CONHCH 2 (CH 2 ) 6 Me, N(SO 2 Et)CH(Me)CONHCH 2 Ph, N(SO 2 Et)CH(Me)CONHPh, NHMe, NHEt, NH-n-Pr, NH-i-Pr, NH-n-Bu, NH-s-Bu, NH-i-Bu , NH-t-Bu, NH-t-Am, NH-n-Am, NH-n-Hex, NHCH 2 (CH 2 ) 6 Me, NHCH 2 Ph, NHPh, NH-(2-NO 2 -Ph), NH-(4-NO 2 -Ph), NH-(2,4-di-NO 2 -Ph), NH-(2-NO 2 -4-CF 3 -Ph), NH-(4-NO 2 -2-CF 3 -Ph), NH-(2,6-di-NO 2 -4-CF 3 -Ph), NH-(2,4-di-NO 2 -6-C F 3 -Ph), NH-(2,4,6-tri-NO 2 -Ph), NH-(2,6-di-NO 2 -4-CF 3 -5-Cℓ-Ph) , NHCH 2 -(2-F-Ph), NHCH 2 -(3-F-Ph), NHCH 2 -(4-F-Ph), NHCH 2 -(2-Cℓ-Ph), NHCH 2 -(3-Cℓ-Ph), NHCH 2 -(4-Cℓ-Ph), NHCH 2 -(2-Br-Ph), NHCH 2 -(3-Br-Ph), NHCH 2 -(4-Br-Ph), NHCH 2 -(2-l-Ph), NHCH 2 -(3-l-Ph), NHCH 2 -(4-l-Ph), NHCH 2 -(2-Me-Ph), NHCH 2 -(3-Me-Ph), NHCH 2 -(4-Me-Ph), NHCH 2 -(2-MeO-Ph), NHCH 2 -(3-MeO-Pn), NHCH 2 -(4-MeO-Ph), NHCH 2 -(4-Et-Ph), NHCH 2 -(4-n-Pr-Ph), NHCH 2 -(4-i-Pr-Ph), NHCH 2 -(4-n-Bu-Ph), NHCH 2 -(4-s-Bu-Ph), NHCH 2 -(4-i-Bu-Ph), NHCH 2 -(4-t-Bu-Ph), NHCH 2 -(4-t-Am-Ph), NHCH 2 -(4-n-Hex-Ph), NHCH 2 -(2-NO 2 -Ph), NHCH 2 -(3-NO 2 -Ph), NHCH 2 -(4-NO 2 -Ph), NHCH 2 -(2-MeOCO-Ph), NHCH 2 -(3-MeOCO-Ph), NHCH 2 -(4-MeOCO-Ph), NHCH 2 -(2-CF 3 -Ph), NHCH 2 -(3-CF 3 -Ph), NHCH 2 -(4-CF 3 -Ph), NHCH 2 -(2-CF 3 O-Ph), NHCH 2 -(3-CF 3 O-Ph), NHCH 2 -(4-CF 3 O-Ph), NHCH 2 -(4-CF 3 CF 2 O-Ph), NHCH 2 -(3-MeCO-Ph), NHCH 2 -(3-HOCO-Ph), NHCH 2 -(4-HOCO-Ph), NHCH(Me)Ph, NHCH 2 CH 2 Ph, N(Me) 2 , N(Et) 2 , N(n-Pr) 2 , N(i-Pr) 2 , N(Me)Et, N(n-Bu) 2 , N(s-Bu) 2 , N(i-Bu) 2 , NHt-Bu) 2 , N(t-Am) 2 , N(n-Am) 2 , NHCF 3 , NHCH 2 CF 3 , NHCH 2 CH 2 CF 3 , NHCH(Me)CF 3 , NHCH(CF 3 ) 2 , NHCH(F)CF 3 , NH(CF 2 ) 3 CF 3 , NH(CF 2 ) 5 CF 3 , NH(CF 2 ) 7 CF 3 , NHCCℓ 3 , NHCHCℓ 2 , NHCH 2 CCℓ 3 , NHCH 2 C ℓ, NHCH 2 CH 2 C ℓ, NHCH 2 CH 2 CH 2 Cℓ, NHCH 2 CH (Cℓ)Me , NHCH 2 C(Cℓ)=CH 2 , NHCH (OH)CCℓ 3 , NHCH=CH 2 , NHCH 2 CH=CH 2 , NHCH (Me) CH=CH 2 , NHC(Me) 2 CH=CH 2 , NHCH 2 C≡CH, NHCH (Me)C≡CH, NHC(Me) 2 C≡CH, NHCH 2 C(Me)=CH 2 , N(CH 2 CH=CH 2 ) 2 , N(CH 2 C≡CH) 2 , NH-c-Pr, NH-c-Bu, NH-c-Pen, NH-c-Hex, NHCH 2 -c-Pr, NHCH 2 -c-Bu, NHCH 2 -c-Pen, NHCH 2 -c-Hex, NHCH 2 OMe, NHCH 2 OEt, NHCH 2 O-n-Pr, NHCH 2 O-i-Pr, NHCH 2 O-n-Bu, NHCH 2 O-s-Bu, NHCH 2 O-i-Bu, NHCH 2 O-t-Bu, NHCH 2 O-t-Am, NHCH 2 O-n-Am, NHCH 2 O-n-Hex, NHCH 2 0C H 2 (CH 2 ) 6 Me, NHCH 2 OCH 2 Ph, NHCH 2 OPh, NHCH 2 CH 2 OMe , NHCH 2 CH 2 OEt, NHCH 2 CH 2 O-n-Pr, NHCH 2 CH 2 O-i-Pr, NHCH 2 CH 2 O-n-Bu, NHCH 2 CH 2 O-s-Bu, NHCH 2 CH 2 O-i-Bu, NHCH 2 CH 2 O-t-Bu, NHCH 2 CH 2 O-t-Am, NHCH 2 CH 2 O-n-Am, NHCH 2 CH 2 O-n-Hex, NHCH 2 CH 2 OCH 2 (CH 2 ) 6 Me, NHCH 2 CH 2 OCH 2 Ph, NHCH 2 CH 2 OPh, NHCH(Me)CH 2 OMe, NHCH(Me)CH 2 OEt, NHCH(Me)CH 2 O-n-Pr, NHCH(Me)CH 2 O-i-Pt, NHCH(Me)CH 2 O-n-Bu, NHCH(Me)CH 2 O-s-Bu, NHCH(Me)CH 2 O-i-Bu, NHCH(Me)CH 2 O-t-Bu, NHCH(Me)CH 2 O-t-Am, NHCH(Me)CH 2 O-n-Am, NHCH(Me)CH 2 O-n-Hex, NHCH(Me)CH 2 OCH 2 (CH 2 ) 6 Me, NHCH (Me)CH 2 OCH 2 Ph, NHCH(Me)CH 2 OPh, NHOCH 2 CO 2 Me, NHOCH 2 CO 2 Et, N(Me)OCH 2 CO 2 Me, N(Me)OCH 2 CO 2 Et, NHNH 2 , NHNHSO 2 Me, NHNHSO 2 Et, NHNHSO 2 -n-Pr, NHNHSO 2 -i-Pr , NHNHSO 2 -n-Bu, NHNHSO 2 -s-Bu, NHNHSO 2 -i-Bu, NHNHSO 2 -t-Bu, NHNHSO 2 -t-Am, NHNHSO 2 -n-Am, NHNHSO 2 -n-Hex, NHNHSO 2 CH 2 (CH 2 ) 6 Me, NHNHSO 2 CH 2 Ph, NHNHSO 2 Ph, NHN(SO 2 Me) 2 , NHN(SO 2 Et) 2 , NHNHSO 2 -n-Pr) 2 , NHN(SO 2 -i-Pr) 2 , NHN(SO 2 -n-Bu) 2 , NHN(SO 2 -s-Bu) 2 , NHN(SO 2 -i-Bu) 2 , NHN(SO 2 -t-Bu) 2 , NHN(SO 2 -t-Am) 2 , NHN(SO 2 -n-Am) 2 NHN(SO 2 -n-Hex) 2 , NHN(SO 2 CH 2 (CH 2 ) 6 Me) 2 , NHN(SO 2 CH 2 Ph) 2 , NHN(SO 2 Ph) 2 , N(NH 2 )SO 2 Me, N(NH 2 )SO 2 Et, N(NH 2 )SO 2 -n-Pr, N(NH 2 )SO 2 -i-Pr, N(NH 2 )SO 2 -n-Bu, N(NH 2 )SO 2 -s-Bu, N(NH 2 )SO 2 -i-Bu, N(NH 2 )SO 2 -t-Bu, N(NH 2 )SO 2 -t-Am, N(NH 2 )SO 2 -n-Am, N(NH 2 )SO 2 -n-Hex, N(NH 2 )SO 2 CH 2 (CH 2 ) 6 Me, N(NH 2 )SO 2 CH 2 Ph, N(NH 2 ) SO 2 Ph, N(COCH 2 Cℓ)CH 2 OEt, N(COCH 2 Br)CH 2 OEt, N(COCH 2 Cℓ)CH 2 O-i-Pr, N(COCH 2 Br)CH 2 O-i-Pr, N(COCH 2 Cℓ)CH 2 O-n-Bu, N(COCH 2 Br)CH 2 O-n-Bu, N(COCH 2 Cℓ)CH 2 O-i-Bu, N(COCH 2 Br)CH 2 O-i-Bu, N(COCH 2 Cℓ) CH 2 CO 2 Me, N(COCH 2 Br)CH 2 CO 2 Et, N(COCH 2 Cℓ)CH(Me)CH 2 OMe, N(COCH 2 Br)CH(Me)CH 2 OMe, N(COCH 2 OMe)CH (Me)CO 2 Me, N(COCH 2 OMe)CH (Me)CO 2 Et, N(COCH 2 OMe)-Q15, N(COCH 2 OMe)-Q15, N(COCH 2 OMe)-Q17, N(COCH 2 OMe)-Q17, N(COCH 2 OMe)-Q19, N(COCH 2 OMe)-Q19, N(CO-Q16)CH(Me)CO 2 Me, N(COCH 2 Cℓ)-Q17, N(COCH 2 Br)-Q17, N(COCH 2 Cℓ)-Q15, N(COCH 2 Br)-Q15, N(COCH 2 Cℓ)CH(Me)CO 2 Me, N(COCH 2 Br)CH(Me)CO 2 Et, N(COCH 2 Ph)CH(Me)CO 2 Me, N(COCH 2 Ph)CH(Me)CO 2 Et, N(CO-c-Pr)-Q15, N (CO-c-Pr)-Q15, NHCO-Q18)CH(Me)CO 2 Me, N(CO-Q18)CH(Me)CO 2 Et, NHCOCH 2 OMe, NHCOCH 2 OEt, NHCH=NOMe, NHCH=NOEt, NHCH 2 CON(Me)-(6-MeO-Q1), NHCH 2 CON(Me)-(6-Me-Q1), NHCH 2 CON(Me)Ph, NHCOCH 2 CH(Me)CH 2 CO 2 H, NHCOCH 2 C(Me)CH 2 CO 2 Me, NHCOCH 2 CH(Me)CH 2 CO 2 Et, NHCOCH 2 CH (CF 3 )CH 2 CO 2 H, NHCOCH 2 CH(CF 3 )CH 2 CO 2 Me, NHCOCH 2 CH(CF 3 )CH 2 CO 2 Et, NHCH 2 SMe , NHCH 2 SO 2 Me, NHCH 2 SEt , NHCH 2 SO 2 Et, NHCH 2 CN in which Q 1 to Q 47 are as shown below. Next, formulation examples of preparations using the compound of the present invention are shown specifically. The formulation examples of the present invention are not limited only to these. In the following formulation examples, all "part"s mean part by weight. [Wettable powder] The compound of the present invention 5 - 80 parts Solid carrier 10 - 85 parts Surfactant 1 - 10 parts Others 1 - 5 parts As the others, there may be mentioned, for example, an anticaking agent. [Emulsifiable concentrate] The compound of the present invention 1 - 30 parts Liquid carrier 30 - 95 parts Surfactant 5 - 15 parts [Flowable formulation] The compound of the present invention 5 - 70 parts Liquid carrier 15 - 65 parts Surfactant 5 - 12 parts Others 5 - 30 parts As the others, there may be mentioned, for example, an antifreezing agent, a thickening agent, etc. [Granular wettable formulation (Dry flowable formulation)] The compound of the present invention 20 - 90 parts Solid carrier 10 - 60 parts Surfactant 1 - 20 parts [Granule] The compound of the present invention 0.01 - 10 parts Solid carrier 90 - 99.99 parts Others 0 - 5 parts [Formulation example 1] Wettable powder Present compound D-12 50 parts Zeeklite PFP 43 parts (Kaolin series clay: produced by Zeeklite Kogyo K.K., tradename) Sorpol 5050 2 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Runox 1000C 3 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Carplex #80 (Anticaking agent) 2 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and pulverized to prepare a wettable powder. [Formulation example 2] Emulsifiable concentrate Present compound D-12 3 parts Xylene 76 parts Isophorone 15 parts Sorpol 3005X 6 parts (Mixture of an nonionic surfactant and an anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) The above components were uniformly mixed to prepare an emulsifiable concentrate. [Formulation example 3] Flowable formulation Present compound D-12 35 parts Agrizole S-711 8 parts (Nonionic surfactant: produced by Kao Corporation, tradename) Runox 1000C 0.5 part (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) 1 % Rodopole water 20 parts (Thickening agent: produced by Rhone-Poulenc S.A., tradename) Ethylene glycol (Antifreezing agent) 8 parts Water 28.5 parts The above components were uniformly mixed to prepare a flowable formulation. [Formulation example 4] Granular wettable powder (Dry flowable formulation) Present compound D-12 75 parts Isobam No. 1 10 parts (Anionic surfactant: produced by Kuraray Isoprene Chemical Co., Ltd., tradename) Vanilex N 5 parts (Anionic surfactant: produced by Sanyo Kokusaku Pulp Co., Ltd., tradename) Carplex #80 10 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and finely pulverized to prepare a dry flowable formulation. [Formulation example 5] Granule Present compound D-12 0.1 part Bentonite 55.0 parts Talc 44.9 parts The above components were uniformly mixed and pulverized, and then a small amount of water was added and the mixture was stirred, mixed and kneaded, and granulated by an extrusion type granulating machine and dried to prepare granule. [Formulation example 6] Wettable powder Present compound D-15 50 parts Zeeklite PFP 43 parts (Kaolin series clay: produced by Zeeklite Kogyo K.K., tradename) Sorpol 5050 2 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Runox 1000C 3 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Carplex #80 (Anticaking agent) 2 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and pulverized to prepare a wettable powder. [Formulation example 7] Emulsifiable concentrate Present compound D-15 3 parts Xylene 76 parts Isophorone 15 parts Sorpol 3005x 6 parts (Mixture of an nonionic surfactant and an anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) The above components were uniformly mixed to prepare an emulsifiable concentrate. [Formulation example 8] Flowable formulation Present compound D-15 35 parts Agrizole S-711 8 parts (Nonionic surfactant: produced by Kao Corporation, tradename) Runox 1000C 0.5 part (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) 1 % Rodopole water 20 parts (Thickening agent: produced by Rhone-Poulenc S.A., tradename) Ethylene glycol (Antifreezing agent) 8 parts Water 28.5 parts The above components were uniformly mixed to prepare a flowable formulation. [Formulation example 9] Granular wettable powder (Dry flowable formulation) Present compound D-15 75 parts Isobam No. 1 10 parts (Anionic surfactant: produced by Kuraray Isoprene Chemical Co., Ltd., tradename) Vanilex N 5 parts (Anionic surfactant: produced by Sanyo Kokusaku Pulp Co., Ltd., tradename) Carplex #80 10 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and finely pulverized to prepare a dry flowable formulation. [Formulation example 10] Granule Present compound D-15 0.1 part Bentonite 55.0 parts Talc 44.9 parts The above components were uniformly mixed and pulverized, and then a small amount of water was added and the mixture was stirred, mixed and kneaded, and granulated by an extrusion type granulating machine and dried to prepare granule. [Formulation example 11] Wettable powder Present compound D-16 50 parts Zeeklite PFP 43 parts (Kaolin series clay: produced by Zeeklite Kogyo K.K., tradename) Sorpol 5050 2 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Runox 1000C 3 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Carplex #80 (Anticaking agent) 2 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and pulverized to prepare a wettable powder. [Formulation example 12] Emulsifiable concentrate Present compound D-16 3 parts Xylene 76 parts Isophorone 15 parts Sorpol 3005X 6 parts (Mixture of an nonionic surfactant and an anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) The above components were uniformly mixed to prepare an emulsifiable concentrate. [Formulation example 13] Flowable formulation Present compound D-16 35 parts Agrizole S-711 8 parts (Nonionic surfactant: produced by Kao Corporation, tradename) Runox 1000C 0.5 part (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) 1 % Rodopole water 20 parts (Thickening agent: produced by Rhone-Poulenc S.A., tradename) Ethylene glycol (Antifreezing agent) 8 parts Water 28.5 parts The above components were uniformly mixed to prepare a flowable formulation. [Formulation example 14] Granular wettable powder (Dry flowable formulation) Present compound D-16 75 parts Isobam No. 1 10 parts (Anionic surfactant: produced by Kuraray Isoprene Chemical Co., Ltd., tradename) Vanilex N 5 parts (Anionic surfactant: produced by Sanyo Kokusaku Pulp Co., Ltd., tradename) Carplex #80 10 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and finely pulverized to prepare a wettable powder. [Formulation example 15] Granule Present compound D-16 0.1 part Bentonite 55.0 parts Talc 44.9 parts The above components were uniformly mixed and pulverized, and then a small amount of water was added and the mixture was stirred, mixed and kneaded, and granulated by an extrusion type granulating machine and dried to prepare granule. [Formulation example 16] Wettable powder Present compound D-22 50 parts Zeeklite PFP 43 parts (Kaolin series clay: produced by Zeeklite Kogyo K.K., tradename) Sorpol 5050 2 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Runox 1000C 3 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Carplex #80 (Anticaking agent) 2 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and pulverized to prepare a wettable powder. [Formulation example 17] Emulsifiable concentrate Present compound D-22 3 parts Xylene 76 parts Isophorone 15 parts Sorpol 3005X 6 parts (Mixture of an nonionic surfactant and an anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) The above components were uniformly mixed to prepare an emulsifiable concentrate. [Formulation example 18] Flowable formulation Present compound D-22 35 parts Agrizole S-711 8 parts (Nonionic surfactant: produced by Kao Corporation, tradename) Runox 1000C 0.5 part (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) 1 % Rodopole water 20 parts (Thickening agent: produced by Rhone-Poulenc S.A., tradename) Ethylene glycol (Antifreezing agent) 8 parts Water 28.5 parts The above components were uniformly mixed to prepare a flowable formulation. [Formulation example 19] Granular wettable powder (Dry flowable formulation) Present compound D-22 75 parts Isobam No. 1 10 parts (Anionic surfactant: produced by Kuraray Isoprene Chemical Co., Ltd., tradename) Vanilex N 5 parts (Anionic surfactant: produced by Sanyo Kokusaku Pulp Co., Ltd., tradename) Carplex #80 10 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and finely pulverized to prepare a wettable powder. [Formulation example 20] Granule Present compound D-16 0.1 part Bentonite 55.0 parts Talc 44.9 parts The above components were uniformly mixed and pulverized, and then a small amount of water was added and the mixture was stirred, mixed and kneaded, and granulated by an extrusion type granulating machine and dried to prepare granule. [Formulation example 21] Wettable powder Present compound D-24 50 parts Zeeklite PFP 43 parts (Kaolin series clay: produced by Zeeklite Kogyo K.K., tradename) Sorpol 5050 2 parts , (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Runox 1000C 3 parts (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) Carplex #80 (Anticaking agent) 2 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and pulverized to prepare a wettable powder. [Formulation example 22] Emulsifiable concentrate Present compound D-24 3 parts Xylene 76 parts Isophorone 15 parts Sorpol 3005X 6 parts (Mixture of an nonionic surfactant and an anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) The above components were uniformly mixed to prepare an emulsifiable concentrate. [Formulation example 23] Flowable formulation Present compound D-24 35 parts Agrizole S-711 8 parts (Nonionic surfactant: produced by Kao Corporation, tradename) Runox 1000C 0.5 part (Anionic surfactant: produced by Toho Chemical Industry Co., Ltd., tradename) 1 %. Rodopole water 20 parts (Thickening agent: produced by Rhone-Poulenc S.A., tradename) Ethylene glycol (Antifreezing agent) 8 parts Water 28.5 parts The above components were uniformly mixed to prepare a flowable formulation. Present compound D-24 75 parts Isobam No. 1 10 parts (Anionic surfactant: produced by Kuraray Isoprene Chemical Co., Ltd., tradename) Vanilex N 5 parts (Anionic surfactant: produced by Sanyo Kokusaku Pulp Co., Ltd., tradename) Carplex #80 10 parts (White carbon: produced by Shionogi & Co., Ltd., tradename) The above components were uniformly mixed and finely pulverized to prepare a wettable powder. Present compound D-24 0.1 part Bentonite 55.0 parts Talc 44.9 parts The above components were uniformly mixed and pulverized, and then a small amount of water was added and the mixture was stirred, mixed and kneaded, and granulated by an extrusion type granulating machine and dried to prepare granule. For practical use, the wettable powder, the emulsifiable concentrate, the flowable formulation and the granular wettable powder are diluted 50 to 1000-fold with water and applied so that the dose of an effective component is 0.0001 to 10 kg per one hectare (ha). Next, availability of the compounds of the present invention as a herbicide is explained specifically by referring to the following test examples. [Test example 1] Test of herbicidal effect by soil treatment In a plastic box having a length of 15 cm, a width of 22 cm and a depth of 6 cm was charged a sterilized diluvial soil, and Echinochloa crus-galli (barnyardgrass), Digitaria adscendens (Crabgrass), Cyperus microira (annual sedge), Solanum nigrum (black nightshade), Galinsoga ciliata (hairy galinsoga), Rorippa indica (indian field cress), rice, corn, wheat, soybean and cotton were sewed mixedly and after covering with soil about 1 cm, chemicals were applied uniformly using a small sized spray on the surface of the soil so that the dose of the effective ingredient is as predetermined. The chemical liquor at applying was used by diluting the preparation prepared according to the above formulation examples, etc., with water and this was applied. After 3 weeks from the application of the chemical liquor, herbicidal effect against respective weeds and crops were examined according to the following judgement standard. The results are shown in Table 3. Judgement standard 5 - Weed killing rate 90 % or more (substantially completely killed) 4 - Weed killing rate 70 to 90 % 3 - Weed killing rate 40 to 70 % 2 - Weed killing rate 20 to 40 % 1 - Weed killing rate 5 to 20 % 0 - Weed killing rate 5 % or lower (substantially no effect) The above weed killing rate was obtained by the following equation by after measuring an above-ground green forage weight in the chemical treated area and an above-ground green forage weight in the non-treated area. Weed killing rate = (1 - (above-ground green forage weight in chemical treated area/above-ground green forage weight in non-treated area)) x 100 [Test example 2] Test of herbicidal effect by foliar treatment In a plastic box having a length of 15 cm, a width of 22 cm and a depth of 6 cm was charged a sterilized diluvial soil, and seeds of Echinochloa crus-galli (barnyardgrass), Digitaria adscendens (Crabgrass), Cyperus microira (annual sedge), Solanum nigrum (black nightshade), Galinsoga ciliata (hairy galinsoga), Rorippa indica (indian field cress), rice, corn, wheat, soybean, cotton and sugar beet were spot-sewed and after covering with soil about 1 cm. Each kinds of plants were reached to 2 to 3-leaf stage, chemicals were applied uniformly to the foliar portion so that the dose of the effective ingredient is as predetermined. The chemical liquor at applying was used by diluting the preparation prepared according to the above formulation examples, etc., with water and this was applied using a small sized spray to whole surface of the foilar portion. After 4 weeks from the application of the chemical liquor, herbicidal effect against respective weeds and crops were examined according to the judgement standard in Test example 1. The results are shown in Table 4. [Test example 3] Test of herbicidal effect under watering condition In 1/5000 are Wagner pot was placed a diluvial soil and water was charged therein and mixed to make a watering condition with a water depth of 2 cm. Each seed of Echinochloa crus-galli (barnyardgrass), Monochoria vaginalis (ducksalad), Rotala indica (toothcap) and Scirpus juncoides (bulrush) was sewed mixedly in the above pot. Also, root of Sagittaria pygmaea (arrowhead) and Cyperus serotinus (perennial flat sedge) were placed therein and rice seedlings at 2.5-leaf stage was transplanted. The pot was placed in a green house at 25 to 30 °C to grow plants, and 2 days after sewing, diluted chemical solution was added dropwise to the water surface with a messpipet so that the dose of the chemical as predetermined. After 3 weeks from the dropping of the chemical liquor, herbicidal effect against respective weeds and crops were examined according to the judgement standard in Test example 1. The results are shown in Table 5. Symbols in the respective tables mean as shown below. N: Echinochloa crus-galli (barnyardgrass) M: Digitaria adscendens (crabgrass) K: Cyperus microiria (annual sedge) H: Solanum nigrum (black nightshade) D: Galinsoga ciliata (hairy galinsoga) I: Rorippa indica (Indian field grass) R: rice T: corn W: wheat S: soybean C: cotton B: sugar beet a: Scirpus juncoides (bulrush) b: Monochoria vaginalis (ducksalad) c: Rotala indica (toothcap) d: Sagittaria pygmaea (arrowhead) e: Cyperus serotinus (perennial flat sedge) f: transplanted rice Compound No. Dose (g/a) N M K H D I R T W S C D- 1 0.4 3 2 5 5 5 5 0 0 0 0 1 D- 2 0.4 3 2 5 5 2 5 1 0 0 0 0 D- 3 0.4 2 3 5 5 5 5 0 0 0 0 0 D- 4 0.4 4 5 5 5 5 5 0 0 0 0 0 D- 5 0.4 2 4 5 5 5 5 1 0 0 0 1 D- 6 0.4 2 3 4 5 5 5 0 0 0 0 1 D- 7 0.4 4 3 5 5 5 5 1 0 0 0 0 D-8 0.4 2 2 4 5 5 5 0 0 0 0 0 D-9 0.4 2 4 5 5 5 5 0 0 0 0 0 D-10 0.4 1 2 4 5 5 5 0 0 0 0 0 D-11 0.4 2 2 3 5 5 5 0 0 0 0 0 D-12 0.4 4 5 5 5 5 5 1 0 0 0 2 D-13 0.4 2 4 4 5 5 5 0 0 0 0 1 D-14 0.1 5 5 5 5 5 5 1 0 0 0 0 D-15 0.4 4 5 5 5 5 5 1 1 0 1 2 D-16 0.1 1 3 5 5 5 5 1 0 0 0 0 D-17 0.4 1 2 1 5 4 5 0 0 0 0 1 D-18 0.4 2 1 5 5 5 5 0 0 0 0 0 D-19 0.4 3 4 5 5 5 5 0 0 0 0 0 D-20 0.1 3 5 5 5 5 5 1 0 0 0 1 D-21 0.4 3 5 5 5 5 5 0 0 0 1 2 D-22 0.1 5 5 5 5 5 5 1 1 1 0 0 D-23 0.1 4 5 5 5 5 5 0 1 0 0 1 D-24 0.1 4 5 5 5 5 5 1 0 1 0 1 D-25 0.1 3 4 5 5 5 5 1 0 0 0 1 D-26 0.1 3 4 5 5 5 5 0 0 0 0 0 D-27 0.1 4 3 5 5 5 5 0 1 0 0 1 D-28 0.1 3 4 5 5 5 5 0 0 0 0 0 D-29 0.4 1 2 2 5 5 5 0 0 0 0 0 D-30 0.4 3 4 5 5 5 5 1 0 1 0 1 D-31 0.4 4 5 5 5 5 5 0 0 0 0 0 D-32 0.4 2 3 5 5 5 5 0 0 0 0 0 D-33 0.4 1 2 3 4 5 5 0 0 0 0 0 D-34 0.4 1 2 4 5 5 5 0 0 0 0 0 D-35 0.4 1 3 5 5 3 5 0 0 0 0 0 D-36 1.6 1 2 5 5 3 5 0 0 0 0 0 D-37 1.6 2 3 5 5 5 5 1 0 0 0 0 D-38 1.6 2 4 5 5 5 5 0 0 0 0 0 D-39 1.6 4 5 5 5 5 5 0 0 0 1 1 D-40 1.6 3 4 5 5 5 5 0 1 1 0 1 D-41 0.4 3 4 5 5 5 5 0 0 0 0 0 D-42 1.6 2 4 5 5 5 5 0 0 0 0 0 D-43 1.6 3 4 5 5 5 5 0 0 0 0 0 D-44 0.4 3 4 5 5 5 5 0 0 0 0 0 D-48 0.4 1 1 5 5 5 5 0 0 0 0 0 D-49 0.4 1 3 5 5 5 5 1 0 0 0 0 D-50 0.4 4 4 5 5 5 5 2 0 1 0 0 D-51 0.4 3 3 5 5 5 5 0 0 0 0 0 D-52 0.4 2 2 5 5 2 5 0 0 0 0 0 D-53 0.4 3 3 5 5 5 5 1 0 1 0 0 D-54 0.4 1 2 4 5 5 5 0 1 1 1 0 D-55 0.4 0 1 2 5 5 5 0 0 0 0 0 D-56 0.4 1 1 5 5 5 5 0 0 0 0 0 D-57 0.4 1 1 5 5 5 5 0 0 0 0 0 D-58 0.4 4 5 5 5 5 5 0 0 1 1 1 D-59 0.4 4 5 5 5 5 5 0 1 1 1 1 D-60 0.4 2 4 5 5 3 5 0 0 0 0 0 D-61 0.1 5 5 5 5 5 5 3 2 2 1 2 D-62 0.4 4 4 5 5 5 5 1 0 0 0 2 D-63 0.4 3 2 5 5 5 5 0 0 0 0 0 D-64 0.4 2 1 5 5 5 5 0 0 0 0 0 D-65 0.4 1 2 5 5 5 5 0 0 1 0 0 D-66 0.1 5 5 5 5 5 5 0 0 0 0 0 D-67 0.1 1 2 5 5 5 5 0 0 0 0 0 D-68 0.4 5 5 5 5 5 5 1 0 0 2 2 D-69 0.4 5 5 5 5 5 5 0 0 3 0 3 D-70 1.6 4 5 5 5 5 5 0 0 0 0 0 D-71 1.6 0 2 5 5 5 5 0 0 0 0 1 D-72 1.6 4 4 5 5 5 5 0 0 0 0 0 D-73 1.6 5 5 5 5 5 5 0 0 1 0 0 D-74 0.4 5 5 5 5 5 5 1 1 0 1 1 D-75 1.6 5 5 5 5 5 5 1 1 1 1 1 D-76 0.4 5 5 5 5 5 5 0 0 0 0 0 D-77 0.4 5 5 5 5 5 5 0 0 0 0 0 D-78 0.4 5 5 5 5 5 5 1 2 1 3 3 D-79 1.6 5 5 5 5 5 5 2 1 0 3 1 D-80 0.4 5 5 5 5 5 5 0 0 0 0 0 0 D-81 1.6 2 3 5 5 5 5 1 0 0 0 0 0 D-82 0.4 5 5 5 5 5 5 3 1 2 1 0 D-83 1.6 2 5 5 5 5 5 0 0 0 3 3 D-84 1.6 3 5 5 5 5 5 1 0 0 0 0 D-85 1.6 4 4 5 5 4 5 0 0 0 0 0 D-86 0.4 5 5 5 5 5 5 0 1 0 0 0 D-87 1.6 2 2 4 5 3 5 0 0 0 0 0 D-88 0.4 1 2 5 5 5 5 0 0 0 0 0 D-89 0.1 2 4 5 5 5 5 0 0 0 0 0 D-90 1.6 5 5 5 5 5 5 0 0 0 0 0 D-91 0.4 5 5 5 5 5 5 1 1 0 1 1 D-92 0.4 3 1 5 5 5 5 0 0 0 0 1 D-93 1.6 5 5 5 5 5 5 0 0 0 0 0 D-94 1.6 2 5 5 5 5 5 1 0 1 0 0 D-95 6.3 2 5 5 5 5 5 1 0 0 0 5 D-96 1.6 5 5 5 5 5 5 2 0 2 2 2 D-97 0.4 5 5 5 5 5 5 0 0 0 0 3 D-98 0.4 5 5 5 5 5 5 0 0 0 0 1 Compound No. Dose (g/a) N M K H D I R T W S C B D- 1 0.4 2 1 5 5 5 5 1 1 0 4 5 5 D- 2 0.4 2 1 5 5 3 2 0 2 0 3 4 5 D- 3 0.4 2 1 5 5 5 5 0 1 0 3 5 5 D-4 0.4 4 5 5 5 5 5 1 3 0 5 5 5 D-5 0.4 2 3 5 5 5 5 1 2 0 4 4 5 D- 6 0.4 2 3 5 5 5 5 1 1 0 4 5 5 D- 7 0.4 3 3 5 5 5 5 2 2 0 5 5 5 D- 8 0.4 2 1 5 5 5 5 0 0 0 3 5 5 D-9 0.4 2 3 5 5 5 5 1 2 0 3 4 5 D-10 0.4 2 2 5 5 5 5 0 0 0 2 5 5 D-11 0.4 3 3 5 5 5 4 1 2 1 4 4 4 D-12 0.1 4 3 5 5 5 5 0 2 0 3 4 5 D-13 0.4 2 1 5 5 5 4 0 2 1 2 5 5 D-14 0.1 3 2 5 5 5 5 1 2 1 5 5 5 D-15 0.4 2 3 5 5 5 5 1 2 0 5 5 5 D-16 0.1 2 2 4 5 5 2 1 1 0 2 5 5 D-17 1.6 1 2 1 5 5 5 0 0 0 3 2 3 D-18 0.4 2 2 5 5 5 5 0 0 0 3 5 5 D-19 1.6 4 2 3 5 5 5 0 1 2 4 5 4 D-20 0.4 3 4 5 5 5 5 2 3 1 3 4 4 D-21 0.4 2 2 2 5 5 3 0 0 0 3 2 3 D-22 0.1 2 3 5 5 5 5 1 2 0 5 5 5 D-23 0.1 2 5 5 5 5 5 1 2 0 5 5 5 D-24 0.1 2 3 5 5 5 4 1 1 2 4 5 5 D-25 0.1 2 4 5 5 5 4 1 2 1 4 5 5 D-26 0.1 2 3 5 5 5 4 1 1 0 4 5 5 D-27 0.1 3 3 5 5 5 4 1 1 1 5 5 5 D-28 0.1 2 3 5 5 5 5 1 1 0 5 5 5 D-29 0.4 2 3 5 5 5 5 0 0 0 2 4 3 D-30 0.4 4 3 5 5 5 5 1 1 0 4 5 5 D-31 0.4 3 2 5 5 5 5 0 1 0 3 5 5 D-32 0.4 2 2 5 5 5 5 0 1 0 2 5 4 D-33 1.6 4 2 2 5 5 5 1 0 0 4 5 5 D-34 1.6 2 2 5 5 5 5 1 2 1 4 5 5 D-35 0.4 2 3 5 5 5 5 0 0 0 3 2 2 D-36 0.4 2 2 5 5 5 3 0 0 0 3 5 3 D-37 0.4 2 3 5 5 5 2 0 0 0 3 5 5 D-38 0.4 2 2 5 5 5 4 0 1 0 4 5 5 D-39 1.6 3 4 5 5 5 5 0 2 0 5 5 5 D-40 1.6 2 3 5 5 5 5 0 2 1 4 5 5 D-41 0.4 3 4 2 5 5 5 1 3 0 5 4 3 D-42 1.6 2 2 2 5 5 5 5 0 1 2 4 3 D-43 1.6 3 2 5 5 5 4 1 1 0 2 5 5 D-44 0.4 1 2 2 5 5 5 0 0 0 2 3 3 D-48 0.4 1 1 5 5 5 5 0 0 0 2 5 3 D-49 0.4 2 1 5 5 5 5 1 2 1 5 5 5 D-50 0.4 2 1 5 5 5 5 2 2 1 4 5 5 D-51 0.4 5 2 5 5 5 5 1 4 4 5 5 5 D-52 0.4 4 2 5 5 5 5 1 3 1 5 5 5 D-53 0.4 5 2 5 5 5 5 1 3 1 5 5 5 D-54 0.4 2 1 5 5 5 5 1 3 1 5 5 5 D-56 0.4 1 1 5 5 5 2 0 0 0 3 5 5 D-57 1.6 1 1 5 5 5 5 0 1 1 1 5 4 D-58 0.4 2 4 5 5 5 5 0 1 1 4 5 5 D-59 1.6 3 4 5 5 5 5 2 2 1 5 5 5 D-60 1.6 2 3 5 5 4 3 1 2 1 5 5 5 D-61 0.1 2 1 5 5 5 5 2 3 2 3 5 5 D-62 0.4 2 1 5 5 5 5 1 2 1 5 5 5 D-63 0.4 2 2 5 5 5 5 1 2 1 3 5 2 D-64 0.4 2 1 5 5 5 5 1 3 1 4 5 4 D-65 0.4 2 1 5 5 5 5 1 3 2 5 5 5 D-66 0.1 3 2 5 5 5 5 1 2 0 5 3 5 D-67 0.1 1 1 5 5 5 5 0 2 1 4 5 5 D-68 0.4 3 1 2 5 5 5 0 0 0 3 3 2 D-69 0.4 4 0 2 5 5 5 1 3 3 5 5 1 D-70 1.6 1 1 2 5 5 5 1 3 0 1 2 1 D-71 1.6 0 0 2 5 5 5 0 2 0 4 3 1 D-72 1.6 2 0 2 5 5 4 1 1 0 3 3 1 D-73 1.6 3 0 2 5 5 5 1 2 1 3 3 3 D-74 0.4 2 0 1 5 5 5 1 1 1 3 3 2 D-75 1.6 4 0 0 5 4 4 1 3 1 3 3 0 D-76 0.4 2 0 1 5 5 5 0 2 0 2 4 0 D-77 0.4 3 0 2 5 5 5 0 2 0 5 3 2 D-78 0.4 3 0 2 5 5 5 1 3 1 3 3 2 D-79 1.6 5 1 5 5 5 5 2 4 1 4 5 2 D-80 0.4 4 0 3 5 5 5 1 2 0 3 3 1 D-81 1.6 1 0 1 5 5 5 1 1 0 3 3 1 D-82 0.4 4 1 2 5 5 4 2 3 1 4 3 1 D-83 1.6 1 1 3 5 5 5 1 2 0 4 4 1 D-84 1.6 2 1 0 5 5 5 3 1 1 2 3 2 D-85 1.6 0 0 0 5 4 5 0 0 0 1 0 0 D-86 0.4 1 0 1 5 4 3 0 2 0 1 2 0 D-87 1.6 0 0 1 5 4 5 0 1 0 0 1 0 D-88 0.4 1 1 4 5 5 5 0 0 0 2 2 2 D-89 0.1 2 1 4 5 5 5 0 0 0 4 3 2 D-90 1.6 1 1 2 5 5 5 1 1 0 3 3 3 D-91 0.4 4 1 2 5 5 5 1 1 0 4 3 2 D-92 0.4 1 1 2 5 5 5 0 1 0 2 5 2 D-93 1.6 1 1 1 5 5 5 0 0 0 3 3 3 D-94 1.6 2 3 3 5 5 5 1 1 2 3 5 0 D-95 6.3 2 1 3 5 5 5 0 0 0 2 5 2 D-96 1.6 5 2 5 5 5 5 2 0 2 3 5 3 D-97 0.4 5 2 5 5 5 5 5 0 4 5 5 5 D-98 0.4 5 3 5 5 5 5 5 0 5 4 5 5 Compound No. Dose (g/a) N a b c d e f D-31 0.4 5 5 5 5 4 5 0 D-53 0.4 5 5 5 5 4 5 0 D-54 0.4 5 5 5 5 5 5 0 D-61 0.4 5 5 5 5 5 5 0 D-62 0.4 5 5 5 5 5 5 0 D-63 0.4 5 5 5 5 5 5 0 D-64 0.4 5 5 5 5 5 5 0 D-65 0.4 5 5 5 5 5 5 0 D-66 0.4 5 5 5 5 5 5 0 D-67 0.4 5 5 5 5 5 5 0 D-69 0.4 5 5 5 5 5 5 0 D-70 0.4 5 5 5 5 4 5 0 D-76 0.4 5 5 5 5 4 5 0 D-77 0.4 5 5 5 5 5 5 0 D-80 0.4 5 4 5 5 5 5 0 D-82 0.4 5 5 5 5 5 4 0 D-89 0.4 5 4 5 5 5 5 0 D-91 0.4 5 5 5 5 5 4 0 D-96 0.4 5 3 5 5 5 4 0 <Utilizability in industry> The uracil derivative represented by the formula (I) of the present invention can be used for important crops with safety and shows high herbicidal effect agains many weeds with low dose, and is available as an active ingredient for a selective herbicide.

Claims: A uracil derivative represented by the formula (1): wherein: R 1 is hydrogen, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl R 2 is C 1 -C 6 haloalkyl R 3 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxymethyl, a halogen or nitro; R 4 is a hydrogen atom or a halogen; R 5 is a halogen, nitro or cyano; X is an oxygen atom; D a and D b each independently represents hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl C 3 -C 8 alkynyl, -L 2 -D 52 in which D 52 is hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 3 -C 8 cycloalkyl(C 1 -C 4 ) alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, Ar which is a phenyl group which is unsubstituted or substituted by one or two or more substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, a halogen, nitro, C 1 -C 4 alkoxy and C 1 -C 4 alkoxycarbonyl, -L 1 -Ar wherein Ar is as defined above and L 1 is a C 2 to C 6 alkyl chain, a C 2 to C 6 alkenyl chain or a C 2 to C 6 alkynyl chain each of which may be branched, or -L 1 -Het wherein L 1 is as defined above, Het is a pyridine or thiophene ring, and L 2 represents -C(O)-, -SO 2 -, -S(O)-, -S-, -C(O)O-, -C(O)S- or -C(O)C(O)O-, -L 3 -C(O)O-D 52 in which D 52 is C 1 -C 20 alkyl and L 3 is a C 1 -C 6 alkyl chain, -C(O) -ND 52 D 53 in which D 52 is hydrogen and D 53 is C 1 -C 8 alkyl or C 1 -C 6 alkylsulfonyl, =CD 54 -ND 52 D 53 in which D 52 and D 53 are C 1 -C 6 alkyl and D 54 is hydrogen, or alternatively D a and D b together with a nitrogen atom to which they are attached form a 3- to 8-membered ring represented by provided that the cases where (a) D a and D b both represent hydrogen, and where one of D a and D b represents -L 2 -D 52 (L 2 represents -SO 2 -, and D 52 represents C 1 -C 4 alkyl or C 1 -C 3 haloalkyl), and the other of D a and D b is hydrogen, C 1 -C 4 alkyl, C 2 -C 5 alkenyl, or C 3 -C 5 alkynyl; and (b) one of D a and D b is -L 2 -D 52 in which L 2 is -SO 2 - and D 52 is a C 1 -C 4 alkyl or C 1 -C 3 haloalkyl group; are excluded. A uracil derivative according to claim 1 wherein R 1 is methyl; R 2 is trifluoromethyl; R 3 is hydrogen; R 4 is a hydrogen atom or a halogen; R 5 is a halogen; X is an oxygen atom; Da and Db each independently represent hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, -L 2 -D 52 in which D 52 is hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 3 -C 8 cycloalkyl (C 1 -C 4 ) alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl C 1 -C 4 alkoxy (C 1 -C 4 ) alkyl, Ar as defined in claim 1, L 1 -Ar as defined in claim 1 or L 1 -Het as defined in claim 1, and L 2 is as defined in claim 1, -L 3 -C(O)0-D 52 in which D 52 is C 1 -C 20 alkyl and L 3 is a C 1 -C 6 alkyl chain, -C(O) -ND 52 D 53 in which D 52 is hydrogen and D 53 is C 1 -C 8 alkyl or C 1 -C 6 alkylsulphonyl, or =CD 54 -ND 52 D 53 as defined in claim 1. A herbicide comprising a suitable carrier and, as an effective ingredient, a uracil derivative as defined in claim 1 or 2. A herbicide according to claim 3 which is in the form of a liquid formulation, an emulsifiable concentrate, a wettable powder, a dry flowable formulation, a flowable formulation, a dust or granules. A herbicide according to claim 3 or 4 which further comprises an insecticide, a plant growth regulator or a synergist. A method for killing weeds or inhibiting their growth, which comprises applying thereto a uracil derivative as defined in claim 1 or 2 or a herbicide as defined in any one of claims 3 to 5 in an amount effective for killing the weeds. A method according to claim 6 wherein the dosage of the uracil derivative is from 0.001 to 5 kg per hectare. A process for producing the uracil derivative as defined in claim 1 or 2, which process comprises reacting a β-acrylate ester of the formula (5): in which G 1 is C 1 -C 4 alkyl or an N-alkyl-β-acrylate ester of formula (8): with a phenyliso(thio)cyanate of formula (6): or an N-phenyl(thio)carbamate represented by the formula (7) : in which G 2 is C 1 -C 4 alkyl or a phenyl group, and, if necessary, reacting the resulting product with an alkylating agent. A process for producing a uracil derivative as defined in Claim 1 or 2, which process comprises reacting an aminoaryl uracil compound represented by the formula (9) : with a D a -halogen compound, and then reacting the resulting product with a D b -halogen compound in which D a and D b are as defined in claim 1.

Inventors: ENDO TOSHIHARU, FUKUDA KENZOU, ISHIKAWA KIMIHIRO, ITOH KAORU, KAWAMURA YASUO, KITA HIROSHI, NAWAMAKI TSUTOMU, SATOW JUN, SUZUKI KOICHI, WATANABE SHIGEOMI, ENDO, TOSHIHARU, FUKUDA, KENZOU, ISHIKAWA, KIMIHIRO, ITOH, KAORU, KAWAMURA, YASUO, KITA, HIROSHI, NAWAMAKI, TSUTOMU, SATOW, JUN, SUZUKI, KOICHI, WATANABE, SHIGEOMI, ENDO, TOSHIHARU, NISSAN CHEM. IND. LTD., FUKUDA, KENZOU, NISSAN CHEM. IND. LTD., ISHIKAWA, KIMIHIRO, NISSAN CHEM. IND. LTD., ITOH, KAORU, NISSAN CHEM. IND. LTD., KAWAMURA, YASUO, NISSAN CHEM. IND. LTD., KITA, HIROSHI, NISSAN CHEM. IND. LTD., NAWAMAKI, TSUTOMU, NISSAN CHEM. IND. LTD., SATOW, JUN, NISSAN CHEM. IND. LTD., SUZUKI, KOICHI, NISSAN CHEM. IND. LTD., WATANABE, SHIGEOMI, NISSAN CHEM. IND. LTD.
Applicants: NISSAN CHEMICAL IND LTD, NISSAN CHEMICAL INDUSTRIES, LIMITED
Application year: 1991
Main classification: C07D239
IPC codes: C07D403, C07D401, C07F9, C07D239, A01N47, A01N43, A01N57, C07D417, C07D409