JPH03204865A - Uracil derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I [R<1> is H, 1-2C (halo)alkyl or hydroxymethyl; R<2> is 1-6C haloalkyl; R<3> is H, 1-6C (halo)alkyl, hydroxymethyl, halogen or NO2; R<4> is H or halogen; R<5> is halogen, NO2 or CN; R<6> is S-B<1> (B<1> is H, 1-5C alkyl, 3-6C cycloalkyl, 2-4C alkenyl, benzyl, etc.), group shown by formula II (D<21> is H, 1-3C alkyl, 1-3C alkoxy, etc.; D<22> is H, 1-4C alkyl, phenyl, etc.), etc., or R<5> and R<6> form ring; X is O or S]. EXAMPLE:3-(7-Fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-1-methyl-6- trifluoromethyl-2,4(1H,3H)-pyrimidinedione. USE:A herbicide. PREPARATION:For example, a beta-aminoacrylic ester shown by formula III is reacted with a phenyl (thio)isocyanate shown by formula IV and then alkylated to give a compound shown by formula I.

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a novel uracil derivative and a selective herbicide containing the derivative as an active ingredient. [Prior Art and Issues] Many herbicides have been put into practical use to protect important crops such as rice, soybeans, wheat, corn, cotton, beets, etc. from weeds and to increase the productivity of these important crops. It's here. These agents can be broadly classified into three categories depending on the application situation: upland cultivation, paddy field cultivation, and non-cultivated land cultivation. moreover,
Depending on the method of drug application, these can be classified into soil mixing treatment type, pre-emergence soil treatment type, post-emergence treatment (foliage treatment) type, etc. In recent years, as the world's population has increased, it is clear that the productivity of important crops is having an impact on the food economy of each country. Along with these changes, it is inevitable that traditional agricultural forms will change as we head into the 21st century. In fact, for farmers, there is an increasing need than ever before for the development of herbicides that can economically and efficiently kill or control weeds that become obstacles during crop cultivation. There is a strong desire to develop such herbicides that meet the following requirements. Those that have a high herbicidal effect at a low dose (particularly from the perspective of environmental protection, it is necessary to kill weeds by spraying as low a dose as possible), and those that have a moderate residual effect (in recent years, it is necessary to spray as low a dose as possible to kill weeds. It is a problem that long-lasting chemicals can damage subsequent crops, so it is important that they have a suitable residual effect after spraying. (After that, it is possible to sow and transplant the next crop in a short period of time), and those that require fewer chemical treatments (it is important for farmers to minimize the number of times they have to perform complicated weed control operations). , A wide range of weed control targets (it is desirable to use a single drug that can control weed species with different properties such as broad-leaved weeds, grass weeds, and perennial weeds), and there are many application methods. (By combining soil treatment effect, foliage treatment effect, etc., a more powerful herbicidal effect can be obtained.) Items that do not cause harmful chemical damage to crops (In cultivated land where crops and weeds coexist) It is preferable if it can selectively kill only weeds. However, existing herbicides do not meet all of these conditions. On the other hand, it is known that certain compounds of uracil derivatives exhibit herbicidal activity; for example, ThePesticide
e Manual 8th edition, page 89 The Br1t
ishCrop Protection Council
(1987) and others describe Bromacil as one of the herbicides having a uracil skeleton. [Means for Solving the Problems] In view of this situation, the present inventors have developed a compound that exhibits selectivity for important crops and has excellent herbicidal effects against many weeds at low doses. As a result of continuing research to develop a herbicide that has both soil treatment and foliage treatment effects, the formula (I) 1 was developed.

[In the formula, R1 represents a hydrogen atom, a 01-C3 alkyl group, a hydroxymethyl group, or a 01-C3 haloalkyl group, R2 represents a C5-C@haloalkyl group, and R3 represents a hydrogen atom, a C3-C6 alkyl group, 01 ~C6 represents a haloalkyl group, hydroxymethyl group, halogen atom or nitro group, R4 represents a hydrogen atom or a halogen atom, R5 represents a halogen atom, nitro group or cyano group, R6 represents -3-B' (however, B' is a hydrogen atom, C1~
C5 alkyl group, C3-C6 cycloalkyl group, C2-
C4 alkenyl group, C3-C4 alkynyl group, cyanomethyl group, hydroxymethyl group, chloromethyl group, benzyl group, 1 CO2B22 (however, B21 is a hydrogen atom, C7-C3 alkyl group, methylthio group, phenylthio group or methoxymethyl 1322 represents a hydrogen atom, sodium atom, potassium atom, ammonium group, isopropylammonium group, C1-C5 alkyl group, C2-C5 alkenyl group, C3-C5 alkynyl group, C3-C6 cycloalkyl group, (C, ~C6 cycloalkyl) 01-C2 alkyl group, 02-C3 haloalkyl group, phenethyl group,
α-Methylbenzyl group, 3-dimethylaminopropyl group, phenyl group optionally substituted with one or more substituents (however, the substituents are halogen atoms, 01-
C4 alkyl group, 01-C, alkoxy group, 01-C2
Alkylamino group, dimethylamino group, (C, ~C2 alkoxy)carbonyl group, C2~C, acyl group, C1~
Represents a C2 haloalkyl group or a C0 to C2 haloalkyloxy group. ) or a benzyl group which may be substituted with one or more substituents (however, the substituents are a halogen atom, 01-C, alkyl group, C, -C, alkoxy group, 01-C2 alkylamino group, dimethyl amino group,
02-C, acyl group, trifluoroacetylamino group,
(C, ~C2 alkoxy) carbonyl group, methylsulfonyl group, trifluoromethylsulfonyl group, C3 ~ C2
Represents a haloalkyl group, a C1-C2 haloalkyloxy group. ) represents. ], CH2(-CH2→=.CO2B2
2 [However, B 22 represents the same meaning as above, and n is 1
Represents an integer of ~4. ],]CH, -Y-B2'' However, B
22 represents a hydrogen atom, a C3-C5 alkyl group, a cyanomethyl group, a C2-C5 acyl group, a chloroacetyl group or a dimethylcarbamoyl group, and Y represents an oxygen atom or a sulfur atom. ), CH2-Y-CH(B”)CO2
B22 (However, B21B12 and Y represent the same meanings as above.) or CHl-CH2-(-CH2→
= Co2B22 (however, 1322 n and Y represent the same meanings as above)], D2' -C=NOCH2CO□D22 [however, [)21 is a hydrogen atom, 01-C3 alkyl group, C3- Represents a C3 alkoxy group or (01-C3 alkoxy) C1-C2 alkyl group, B22 is a hydrogen atom, 01-C4 alkyl group, 0
Represents a 3-C6 cycloalkyl group, a 02-C3 haloalkyl group, a phenyl group or a benzyl group. ], I)21
I) 23 -C=NN=CCO, D22 (however, B21 and 1
)22 represents the same meaning as above, and B22 represents a hydrogen atom or an 01-C3 alkyl group. ], [)24 represents a hydrogen atom, an 01-C3 alkyl group or a (C,-C3 alkoxy)C1-C2 alkyl group, and Z represents an oxygen atom, a sulfur atom or NH. ], 26 -N-3O2D" (however, D2S is a hydrogen atom, a sodium atom, a 01-C4 alkyl group, a C2-C, alkenyl group, a C3-C5 alkynyl group, a C2-C5 acyl group, a C3-C4 alkylsulfonyl group) or (C, ~C3
alkoxy)CI''-represents a C2 alkyl group, B26
represents an 01-C4 alkyl group or a 01-C3 haloalkyl group. ], (However, ]) 27 is a hydrogen atom, 01-C6 alkyl group,
03-C6 cycloalkyl group, 01-C3 haloalkyl group, C1-C4 alkoxy group, 01-C4 alkylthio group, (C3-C4 alkoxy)carbonyl group, mercapto group, hydroxyl group, (C,-C3 alkoxy)01-C2 alkyl group, C3-C4 alkyl/1,7mino group, ND"(
D”) (However, D”, !=D” are each independently C
Represents a 2-C4 alkyl group. ), dimethylcarbamoyl group, C0NH30□CH3,
C1-C4 alkylsulfonyl group or N(D',')
So□D31 (however, D30 represents a hydrogen atom, a sodium atom, a C2-C4 alkyl group, a C3-C4 alkylsulfonyl group, (C, ~C, C3 alkoxy 3-C, alkyl group, and D31 represents a C3-C4 alkyl group) group or C3~
Represents a C3 haloalkyl group. ) represents. ], [However, p22 is C2-C, alkyl group or 03-C
6 represents a cycloalkyl group. ], [However, D31, D34 and D25 each independently represent a hydrogen atom or a C3-C6 alkyl group. ]
, [However, D36 and D37 each independently represent a hydrogen atom, a C3-C6 alkyl group, or a dimethylamino group. ], [However, D″′ is a hydrogen atom, a halogen atom, a mercapto group, a hydroxyl group, a C3-C6 alkyl group, a 03-C6 cycloalkyl group, a C3-C3 haloalkyl group, a C3-C4 alkoxy group, a 01-C4 alkylthio group , (C3-C4
alkoxy) carbonyl group, dimethylcarbamoyl group,
(C, -C3 alkoxy)01-C2 alkyl group, CI
~C4 alkylamino group, ND"(D")CHoweverL,D"
and I) 29 represents the same meaning as above. ),C
0NH302CH3, C1-C4 alkylsulfonyl group, phenyl group, benzyl group or N(D29)SO□D
31 (However, D31 represents the same meaning as above, Do is a hydrogen atom, a CI-C4 alkyl group, a sodium atom, a potassium atom, a C1-C4 alkylsulfonyl group, or (
C3-C3 alkoxy) represents a C3-C2 alkyl group. ) represents. ], nitro group, amino group, cyano group, C1-C4 alkylamino group, N(D")D"C However, D2m and D2
9 represents the same meaning as above. ), represents a C3-C4 alkylcarbonyl group or a (C3-C4 alkoxy)carbonyl group. ], [However, D40 is a hydrogen atom, a CI-Ca alkyl group, 0
3-C6 cycloalkyl group, phenyl group, benzyl group or 2-pyridyl group, 1) 41 is hydrogen atom, halogen atom, mercapto group, hydroxyl group, amino group, C3-C
6 alkyl group, 01-C4 alkylamino group, ND''(
D") (however, D2g and ]2G represent the same meanings as above), C3-C4 alkylthio group, CO□D"
(However, 1) 21 represents the same meaning as above. ), C
1-C4 alkylsulfonyl group, C1-C4 alkoxy group or N(D'')SO□])31 (however, D31 and D2' represent the same meanings as above), D42
is a hydrogen atom, a halogen atom, [however, D4m represents a hydrogen atom, a hydroxyl group, a methoxy group, an amino group, a benzoyl group, or a 01-C4 alkyl group, and p44 represents a hydrogen atom, a cyano group, an acetyl group, a C1-C4 alkyl group , represents a carboxyl group or a (C, to C4 alkoxy) carbonyl group. ], [However, 1) 46 and p4g are each independently a hydrogen atom, a phenyl group, a hydroxyl group, a methoxy group, or a C5 to C4
Represents an alkyl group. ] or [However, D47 and D4g each independently represent a hydrogen atom or an 01-C4 alkyl group. ] represents. X represents an oxygen atom or a sulfur atom. However, when R5 and R6 form a ring, formula (II), formula (IV-1), formula (IV-2), formula (IV-3) or formula (IV-4) 1 [wherein, RI , R2, R2, R4 and X represent the same meanings as above, AI represents a hydrogen atom or c, -C4 alkyl group, A2 represents a hydrogen atom, a C3-C5 alkyl group, a C2-C5 alkenyl group, a C3- C5 alkynyl group, (C, ~C6 cycloalkyl > C, -C2 alkyl group, C1 ~ C6 haloalkyl group, C1 ~ C6 haloalkenyl group, C3 ~ C
6-haloalkynyl group, cyanomethyl group, hydroxymethyl group, tetraromethyl group, (C, ~C3 alkoxy)01
~C2 alkyl group, -CH2CO□A21 [However, A2
1 represents a hydrogen atom, an 01-C5 alkyl group, a sodium atom, a phenyl group optionally substituted with a halogen atom, or a benzyl group optionally substituted with a halogen atom. ), -CH2CON(A22)A23 (However, A2
2 and A23 are each independently a hydrogen atom or 01
~ Represents a C3 alkyl group. ], an optionally substituted phenyl group (however, the substituents are 01-C4 alkyl group, 0
Represents a 1-C4 haloalkyl group, a 01-C4 alkoxy group, and a halogen atom. ), an optionally substituted benzyl group (however, the substituent is a C3-C4 alkyl group, 01-C4
Haloalkyl group, C3-C4 alkoxy group, (C, ~C
4 alkoxy) carbonyl group, (C,~C3 alkoxy)01~C2 alkyl group, and a halogen atom. ) or -CH,A'' (where A24 is an optionally substituted 2-pyridyl group (however, the substituent represents a C3-C4 alkyl group or a halogen atom), an optionally substituted 2-pyridazyl group (however, the substituent represents a C3-C4 alkyl group or a halogen atom), a 3-isothiazole group or a 3-isoxazole group], J is a hydrogen atom, a 01-C4 alkyl group, a C2 -C4 alkenyl group, C3-C4 alkynyl group, hydroxymethyl group, tetraromethyl group, carbamoylmethyl group, cyanomethyl group, (C, -C4 alkoxy)carbonylmethyl group, -C2 alkyl group, (C1-C2 alkoxy)C ~C2
Alkyl group, optionally substituted phenyl group (however,
Substituents include 01-C4 alkyl group, C3-C4 alkoxy group, (01-C4 alkoxy)carbonyl group, (C+-
C4 alkoxy) represents a C3-C2 alkyl group or a halogen atom. ) or an optionally substituted benzyl group (however, the substituent is a C3 to C4 alkyl group, a C0 to C4 alkoxy group, a (C, to C4 alkoxy) carbonyl group, a (0
1-C4 alkoxy) represents a C1-C2 alkyl group and a halogen atom. ) represents. ] Represented by . ] We have found a uracil derivative (hereinafter referred to as the compound of the present invention) represented by The structural feature of the compound of the present invention is that it has a haloalkyl group at the 5-position of the uracil ring, and a unique combination of R', R' and R6 as substituents on the benzene ring at the 2-position of the uracil ring. be. As a result, the compound of the present invention has systemic transferability and extremely high herbicidal activity. As a result, compared to conventional herbicides, the compounds of the present invention can be applied to a wide variety of weeds, including perennial weeds, by either soil treatment or foliage treatment, and are rapidly effective despite being applied at extremely low doses. It has the major characteristics of being highly effective and having a moderate residual effect. The compound of the present invention can be used as a herbicide for upland fields, paddy fields, and non-cultivated land in both soil treatment and foliage treatment. Sunflowers, leaf-trimming plants, staghorn thistles, staghorn daisies, serpent daisies, doggrass, horned mustard, shepherd's purse, dogfish, freckles, purslane, whitewort, koakaza, broom tree, chickweed, stagweed, dayflower, hotokenoza, sycamore, keratinium, serpentine, japonica , Broad-leafed weeds such as madder, violet, American hornwort, and snailweed,
Weeds of the grass family, such as wild trumpet gum, japonica japonica, johnson grass, golden grass, grasshopper, oat, oat grass, foxtail grass, and grass gnome, cyperaceae weeds such as cyperus grass, cyperus spp. It has high herbicidal power against various paddy field weeds such as , Japanese grasshopper, Japanese grasshopper, Japanese grasshopper, etc. at a low dose. It can also be safely used on important crops such as wheat, corn, barley, soybeans, rice, cotton, beets, and turgid gum. The compounds of the present invention are also useful as defoliants. (Hereinafter, blank space) The compounds of the present invention can be synthesized, for example, by the methods shown in Schemes 1 to 4 (R1R2, R3, R
', R5, R' and X have the same meanings as above,
G1 represents a lower alkyl group, and G2 represents a lower alkyl group or a phenyl group. ). ■ (V) (■°) 1 (I) Scheme 1 (V) ■ (1゛) 1 (I) Scheme 2 (■) 1 (I) Scheme 3 Scheme 4 (1) Scheme 1 is the first step. β-aminoacrylic acid ester (V) is reacted with phenyliso(thio)cyanate (VI) to obtain a uracil derivative (■゛),
This represents a method for producing uracil derivative (I) by alkylating the 1-position of the uracil ring as a second step after isolating (ii) or without isolation. (1) First-stage reaction Usually, 0.5 to 1.5 equivalents, preferably 0.9 to 1.1 equivalents of Te (VI) are used relative to (V). Although the reaction proceeds without a solvent, it is usually accelerated by using a solvent. Hexane, heptane, as a solvent
Aliphatic hydrocarbons such as ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, tertiary amines such as pyridine, N,N-diethylaniline, formamide, N,N-dimethylformamide, N-methylpyrrolidone, etc. Examples include acid amides, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, water, and mixtures thereof, and preferably the above-mentioned aliphatic hydrocarbons, acid amides, sulfur-containing compounds, and mixtures thereof. The reaction proceeds with a base (although it can proceed with a base, usually 0.5 to 10 equivalents, preferably 1.0 to 2.0 equivalents relative to (V)). Examples of bases include pyridine, triethylamine, 1.
Nitrogen-containing organic bases such as 4-diazabicyclo[2,2,2]octane, inorganic bases such as hydrogenated potassium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide Examples include metal alcoholades such as sodium ethoxide and potassium tert-butoxide, preferably sodium hydride, sodium hydroxide, and potassium hydroxide. The reaction temperature is usually -40 to 200°C, preferably from room temperature to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes.
It takes from 1 minute to 24 hours. After the reaction is complete, add mineral acids such as hydrochloric acid, acetic acid, trifluoroacetic acid,
(I') can be isolated by acidification with an organic acid such as p-toluenesulfonic acid. (2) 1.0 to 10 equivalents, preferably 1.0 to 5.0 equivalents of alkylating agent are used for the second stage (I'). Alkyl sulfates such as dimethyl sulfate and diethyl sulfate as alkylating agents;
Examples include alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, methyl iodide, and ethyl iodide. Although the reaction proceeds without a solvent, it is usually accelerated by using a solvent. Hexane, heptane, as a solvent
Aliphatic hydrocarbons such as ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, tertiary amines such as pyridine, N,N-diethylaniline, formamide, N,N-dimethylformamide, N-methylpyrrolidone, etc. Examples include acid amides, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, water, and mixtures thereof, and preferably the above-mentioned aliphatic hydrocarbons, acid amides, sulfur-containing compounds, and mixtures thereof. Usually 1.0 to 10 equivalents of base to (■°), preferably 1. O~2.0 equivalents are used. Pyridine, triethylamine, 1,4-diazabicyclo[2,
2,2] Nitrogen-containing organic bases such as octane, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc., and preferably sodium hydride, potassium carbonate, etc. Examples include inorganic bases. The reaction temperature is usually θ to 150°C, preferably from room temperature to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 96 hours, preferably 30 minutes.
It takes from 1 minute to 48 hours. (2) Scheme 2 shows that N-phenyl carbamate (■) is added to β-aminoacrylic acid ester (V) in the first step.
to produce a uracil derivative (I), and after isolating (I'') or continuing without isolation, the 1-position of the uracil ring is alkylated as a second step to produce the uracil derivative (I). (■) 0.5 to 1.5 equivalents, preferably 0.9 to 1.1 equivalents, are used for the first-stage reaction (V). The reaction usually requires a solvent, As a solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, halogenated hydrocarbons such as chloroform, methylene chloride, diethyl ether, dioxane, etc.
Ethers such as tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, tertiary amines such as pyridine, N,N-diethylaniline, formamide, N,
Acid amides such as N-dimethylformamide and N-methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, methanol, ethanol, propatool,
Examples include alcohols such as butanol, water, and mixtures thereof, and preferably the above-mentioned aliphatic hydrocarbons, acid amides, sulfur-containing compounds, and mixtures thereof. Usually 0.5 to 10 equivalent to (V), preferably 1.
0 to 2.0 equivalents are used. As a base, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, potassium te
Examples include metal alcoholades such as rt-butoxide, metal alkylmercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide, and preferably inorganic bases such as sodium hydride and metal alcoholades such as sodium methoxide. . The reaction temperature is usually 0 to 200°C, preferably room temperature to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 12 hours. After the reaction is complete, add mineral acids such as hydrochloric acid, acetic acid, trifluoroacetic acid,
p-) (■°) can be isolated by acidification with an organic acid such as luenesulfonic acid. (2) Second stage The alkylation can be carried out under the same reaction conditions as in the second stage of Scheme 1. (3) Scheme 3 represents a method for producing uracil derivative (I) by reacting N-substituted-β-aminoacrylic acid ester (■) with phenyliso(thio)cyanate (■) in one step, and Scheme 1 It can be carried out under the same reaction conditions. (4) Scheme 4 combines N-substituted -β-aminoacrylic acid ester (■) with N-phenyl carbamate (
(2) represents a method for producing uracil derivative (I) by reacting, and can be carried out under the same reaction conditions as in Scheme 2. Synthesis examples of the compounds and intermediates of the present invention will be specifically described below as examples, but the present invention is not limited thereto. (Hereafter, blank space) Example A-1 3-(7-fluoro-3-oxo-4-propargyl-
2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2,4(IH,3H)
-Synthesis of pyrimidinedione (compound A-1) H1 3-(7-fluoro-3-oxo-4-propargyl-
28-1,4-benzoxazin-6-yl)-6-)
0.18 g of refluoromethyl-2,4(IH,3H)pyrimidinedione was dissolved in sodium hydride (purity 55%) 0
．． 02g suspended in dimethylformamide (2mj7
) solution at room temperature. After 20 minutes, dimethyl sulfate 0.0
9 g was added, and the mixture was stirred overnight. After dimethylformamide was distilled off, water was added and the mixture was extracted with ethyl acetate. After washing with saturated brine and drying over anhydrous sodium sulfate, ethyl acetate was distilled off to obtain a crude product. Preparative thin layer chromatography (developing solvent: hexane: ethyl acetate = 3.1
) to obtain 0.15 g of the target compound as a colorless viscous oil. It solidified when left alone. (Hereafter, blank space) Example A-2 3-(7-fluoro-3-oxo-4-propargyl-
2H-1,4-benzoxazin-6-yl') -6
Synthesis of -1-lyfluoromethyl-2,4(IH.3H)-pyrimidinedione (Compound A-2) 3-Amino-4,4,4-trifluoromethyl-3-amino-4,4,4-trifluoride was added to a mixture of 0.33 g of sodium methoxide and 5 mn of dimethylformamide. Ethyl fluorocrotonate 1. 1 Og was added at room temperature. After 20 minutes, 6-ethoxycarbonylamino-7-fluoro-3-oxo-4-propargyl-2H-1,4-
Add 1.76 g of benzoxazine and heat to 130°C.
heated for an hour. After cooling to room temperature, it was poured into ice water and extracted twice with diethyl ether. The aqueous layer was made acidic with dilute hydrochloric acid, and then extracted three times with ethyl acetate. The ethyl acetate extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled off with ethyl acetate, and then purified by column chromatography (developing solvent: chloroform) to obtain 0.20 g of the target compound as pale yellow crystals. Ta. (Hereafter, blank space) Example A-3 3-[7-fluoro-3-oxo-4-(2pyridylmethyl)-2H-1,4-benzoxazin-6-yl]
-1-methyl-6-trifluoromethyl-2,4(IH
,3H)-pyrimidinedione (compound A-3) 3-(7-fluoro-3-oxo-2H-1,4benzoxazin-6-yl)-1-methyl6-trifluoromethyl-2,4 (IH,3H)-pyrimidinedione 0.
20 g to 0.05 g of sodium hydride (purity 55%)
suspended in N,N-dimethylformamide (5 mA)
Added to solution at room temperature. After 20 minutes, 2-chloromethylpyridine hydrochloride 0,09
g and stirred for 4 hours. After N,N-dimethylformamide was distilled off, water was added and the mixture was extracted with ethyl acetate. After washing with saturated brine and drying over anhydrous sodium sulfate, ethyl acetate was distilled off to obtain a crude product. Preparative thin film chromatography (developing solvent: hexane: ethyl acetate = 2:
3) to obtain 0.09 g of the target compound as pale yellow crystals. (Hereinafter, blank space) Example A-4 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2,4(IH ,3H)-pyrimidinedione (compound A-4) synthesis 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-6
0.85 g of -trifluoromethyl-2,4(IH,3H)-pyrimidinedione was dissolved in 8.5 mj7 of N,N-dimethylformamide, and 0.17 g of anhydrous potassium carbonate was added.
g, 0.15 mI of methyl iodide! was added and stirred for 4 hours. After the reaction was completed, N,N-dimethylformamide was distilled off, water was added, and the mixture was extracted with ethyl acetate. After washing with saturated brine and drying over anhydrous sodium sulfate, ethyl acetate was distilled off to obtain a crude product. This was purified by column chromatography (developing solvent: chloroform) to obtain 0.53 g of the target compound as pale yellow crystals. (Hereinafter, blank spaces) Example B-1 3-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-1-methyl-6-trifluoromethyl-2,4(IH,3H)-pyrimidinedione Synthesis of (Compound B-1) Sodium hydride (purity 55%) Suspended in 5 ml of 0.1 methylformamide, 66 g of 3-(4-chloro-2-fluoro-5dicarbonylmethylthiophenyl)
To this solution, a solution of 1.5 g of methoxytrifluoromethyl-2,4(IH,3H)-pyrimidinedione and 10 mj7 of dimethylformamide was added dropwise at room temperature. After hydrogen generation was completed, 0.59 g of dimethyl sulfate was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 300 mf of water and extracted twice with ethyl acetate. After washing with saturated brine and drying over anhydrous sodium sulfate, ethyl acetate was distilled off to obtain a crude product. This was subjected to preparative thin layer chromatography (developing solvent CH (J's
) and then preparative high performance liquid chromatography (
Purification was performed using eluent CHCN:H20=5:1 to obtain 0.1 g of the target compound as a viscous oil. (Hereinafter, blank space) Example B-2 3-(4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl)-6-trifluoromethyl-2,4(IH,3H)-pyrimidinedione (Compound B
-2) Synthesis A solution of 4.75 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 50 ml of anhydrous toluene was mixed with dimethyl chloride in which 1.14 g of sodium hydride (purity 55%) was suspended. It was added dropwise to a solution of 110 mf of formamide over 15 minutes with stirring at 0°C, and the mixture was heated at O''C for 15 min.
The mixture was stirred for a minute. The reaction mixture was then cooled to -30°C,
A solution of 6.9 g of 4-chloro-2-fluoro-5-methoxycarbonylmethylthiophenyl isocyanate and 50 nH7 of anhydrous toluene was added dropwise. After the reaction mixture was returned to room temperature, it was stirred for 2 hours. After distilling off the solvent, add ethyl acetate and add 20ml of 2N hydrochloric acid! ! , twice with a 500 mA solution of water, then washed with saturated brine, dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain a crude product. This was roughly purified by silica gel column chromatography (developing solvent CHCj7.), and then purified by silica gel column chromatography (developing solvent ethyl acetate:hexane = 3:1) to obtain 1.5 g of the target compound as a viscous oil. Ta. (Hereafter, blank space) Example C-1 3-[4-chloro-2-fluoro-5-(5-methyl-
1,3,4-year-old xadiazol-2-yl)phenyl]
-1-methyl-6-trifluoromethyl-2,4(IH
, 3M)-pyrimidinedione (compound C-1) CH. 0.31 g of sodium hydride (oil, purity 55%),
Dimethylformamide 13mI! 3-[4-chloro-2-fluoro-5-(5-methyl-
(1,3,4-year-old xadiazol-2-yl)phenyl)
-6-trifluoromethyl-2゜4 (IH, 3H)
- 2.5 g of pyrimidinedione, N. A solution of 20ml of N-dimethylformamide was added dropwise. After hydrogen generation was completed, 1.02 g of dimethyl sulfate was added dropwise over 15 minutes. After stirring at room temperature for 2 hours, water was added and extracted with ethyl acetate. After drying with anhydrous sodium sulfate,
The solvent was distilled off and the residue was purified by preparative liquid chromatography (solvent: niacetonitrile:water=5=1) to obtain 0.78 g of the target product. (Hereinafter, blank space) Example C-2 3-[4-chloro-2-fluoro-5-(5-methyl-
1,3,4-oxadiazol-2-yl)phenyl)
-6-) Synthesis of lifluoromethyl-2,4(IH,3H)-pyrimidinedione (compound C-2) Sodium hydride 1.04 g (oil, purity 55%),
Dimethylformamide 75mjl! suspension at 0°C.
A solution of 4.3 g of ethyl 3-amino-4,4,4-trifluorocrotonate and 58 ml of toluene was added dropwise over 15 minutes. After the completion of dropping, stir at 0°C for 15 minutes, -30
Cool to °C and 4-chloro-2-fluoro-5-(5-
Methyl-1,3,4-oxadiazol-2-yl) phenyl isocyanate 5.7 g, toluene 60r++1
! solution was added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and 2N hydrochloric acid (13%) was added to the obtained oil.
．． 3mA, water 300m! ! A solution of was added thereto, and the mixture was extracted twice with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting crude product was purified by preparative liquid chromatography (solvent: acetonitrile:water = 5 = 1). By doing so, 1.78 g of the target product was obtained. Compound Nα 1st H3 A table Structural formula Next, the compounds of the present invention synthesized according to the above examples or schemes, including the compounds synthesized in the above examples, 1st -
The compounds of the present invention are shown in Table A, Table 1-B and Table 1-C, and their physical properties are shown in Table 2-A, Table 2-B and Table 2-C. It is not limited by. Table 1-A (continued) Table 1-A (continued) Compound Nα Structural formula Structural formula Table 1-A (continued) Compound Nα Structural formula () Structural formula Table 1-A (continued) Compound Nα Structural formula () Structural formula Table 1-A (continued) Compound Nα Structural formula Table 1-A (continued) Compound Nα Structural formula Table 1-A (continued) Compound Nα Structural formula () Structural formula ■ Table 1-B Compound Nα Structural formula ( ) Structural formula CH. Table 2-A (continued) Table 2-A (continued) Table 2-A (continued) -1 Table 2-A (continued) Table 2-A (continued) -23 -24 -25 Second Table A (Continued) 6 7 8 Table 2 B (Hereinafter, blank) Table 2-A (Continued) 8-30 Melting point 98 202℃ -33 Glassy Table 2-C Synthesized according to the above examples or schemes Tables 3-A-1 to 3-C-1 show the compounds of the present invention synthesized in the above Examples, but the present invention is not limited thereto. Table 3-A-1 H CH2CH3 CH2CH=CH2 CH2CE:CH CH2Cl. CH2CH=CH2 CH2CyoCH C) (, C3CH CH2C3CH Table 3-A-1 (continued) H20H CH,C* CH2CCH2C8 2CHIC,)2 CH, CH, CH, CH. cH(CH,)CH,CH. CH2Cl(CHs)z CH, C(CHI)I CH, (CH2), CH2 CH, CH2Cl(CH3)2 CH(CH3)CH, CH2Cl. CH2C)](CH-)CH=CH*CH(C2H5)2CH. CH(CHs)C=C)l Table 3-A-1 (continued) CH2C02C. CH2C0N(C)I-) 2 CH2C(hH CH2C02CHs CH2C02C, C5 CH2CO, CH, C, H6 CHzCOz(C-H4-2C1') CH2C02C
H2(C,t(4-4CI)OH, CN CH=CH2 2Hf -CH2(C6H44CIri-CH2(C4H6-2Cf) -cH2cclH4-3CIri cHzcO2Na Table 3-A-1 (continued) C(CHs)we YoCH cCH(CH,)CH= CH2 C(CH,)2CH=CH2 cCH,coNHcH. CH2C0NHCH- CHzCON(CJs) 2 CH,tcON(CH=CH2CH,)2CHzeON
(CH(CH3)z)z CH2CONHCH2CH2CH. CH2C0NHCH(CH-)z CH=CH2CJs CH,C02C)I2C82CH3 CHxC02CH(CI(z)2 CH2C02CH, (CH2)2CH3CH, CH=C
H2CH(CH,)2 CH2CO□CH(CH,)CH2Cl. Table 3-A-1 (continued) 2 CHzCOzC(CHs)z CH2CmiCCH. CH2C82C: CH CH2CmiCCH2CH. CH(CH,)CH2C: CH CH,CH(CH,)CmiCH CH2C0□CHCH, (cis) CH2CH= CHCH2(trans)CH2Cl,
CH=CH2 CH, CH2CH= CHCH. CH2CH2CH= CHCH. CH(CH2)CH=CHCH. CH(CH3)CH= CH2H= CHCH2CH=H2CH3 CH2CH= CH=H2CH. CH2CH2CH. (cis) (trans) (cis) (trans) (cis) (trans) Section 3-A Table 1 (continued) 2 CH, CONHC2H. CH2C0N(C2H5)I CH,C0N(CH,CH2Cl, ). CHzCON(CH(CHi)2)z CHzCONHCH2CHtCHs CH,C0NHCH(CHI)2 CH,CO,C,Hs CHzCOzCHtCHzCHs CH2C02CH(CHI)2 CH,C02CH,(CH2)2C H. CH2C0zCH2CH(CH-)- CH2CO,CH(CH,)CH,CH. CH2C0□C(CHz)s CH2CmiCCH2 CH2C02CHCH CHzC:CCH,CH. Table 3-A-1 (continued) 4 1 2 CH(CHI)2 CH2C02CH2CH. CH(CHa)CHzCH- CH2Cl(CH2)2 CH2C(CH2)I CH2(CH2)3CH2 CH2CH2CH(CH2)2 CH(CH,)CH2CH2CH. CH2Cl(CH,)CH,CH. CH(CJs)2 CH2 CH(CH2)CmiCH C(CH,)2CmiCH CH(CH2)CH= CH2 C(CH3)2cCH= CH2 CH2CONHCH. Table 3-A-1 (continued) 4 1 2 CH(CHriCH2C=CI( CH,CH(CL)CmiCHCH2CH= CHCH-(cis) CH2CH=CHCH2(trans)CH2CH2C
H=CH. C82CH2CH= CHCH5 CI(2CH2CH= CHCH. CH(CH,)CH=CH2H. CH(CHs)CH= CHCH- CH2CH= CHCt(, Cth CH2CH=CHCH2CIh CH2CH2 H2CEN CH2CH= CH2 CH(CHI)C3CH CH2CONH2 (cis ) (trans) (cis) (trans) (cis) (trans) CH3 CH2 CH3 0H. CHs Table 3-A-1 (continued) 2 CH2C=CH. CH2C02C2H. CH2C5Hs CH2C82CH2 CH(CH3)CH= CH2 CH2 C, H5 CH=CH2 Below, margin) Table 3 A-2 (continued) CH2CH=CH. CH,C:N CH2CH3 CH2CH2CH3 CH(CH3)C=CH CH,CH=CH2 CH2C:N CH2Cl. CH2Cl, CHI CH2( , :CH CH(CH,)C=CH CH2CH=CH2 CH2CmiN CH2Cl. CH2CH2CH3 CH2C=CH Table 3 1 2 J r NO. CH3 CH2Cl. CH2CH2CH3 CH(CH,). CF. 0CH2 Ci? CH2CE :CH CH,C:CH CH,CEC)I CH2C=CH CH2C=CH CH2C=CH C)12cECH CH2C:CH CH2C=CH CH2C=CH CH(CH,)C-1: CH Table 3-A-2 (continued) ) CH2C=CH CH, C=CH CH2C=CH CH, OCR. CH20C82CH. CH2C820CH3 o-CHs-benzy I! m-CHs-benzyI! p-CHz-benZyl o-CH3-benzy I! m-CH5-benzy ll p-CH2-benZyl2 o-CH30-benzy 12 m-CHzO-benzyβ p-CH30-benzy I2 Table 3-A-2 (continued) 2 CH, CF. CH3CF3 CH3CF. o-CF3-benzy l Hm-CFz-benzyβ Hp-CFs-benzy I! Section 3-A Table 2 (Continued) 1 2 C, H& o-CH, -pheny I! m-CH2-pheny 12 p-CHs-pheny, 17 o-CHzO-pheny l2 m-CHzO-pheny E Table 3-A-2 (continued) 1 CH3 2 CF. 3 4 1 2 co, -] CHs CH. CH. C.F. C.F. C.F. CH2-(I>CH2CH2< CH(CH,)be1 3rd-A 2 3 CF. CFs CF. CF. CF3 CF. CF3 CF, CF2 CF, CF2 CF, CF. CFzcp2 F2CF2 CFzcp. CF, CF2 CF3CF2 CF3CF 2Table 4 (continued) 1 2 p-cLo-pheny Jl' o-CI! -pheny 1! m-CA' -phenyf p-CA -pheny A O-CF 3-pheny 12 m CFz-phenyffi p-CFz -pheny 1! CH. H2GHz CH2Cl(2CH2 CH2CH=CH. CH,C=CH CH(CHI)CE CH C,HI C+oHt Table 3-A-2 (continued) 2 R'R' CF, CF2 H CF2CF2 C11 CF, CF2 CH. CF, CF, H CF, CF2 H CF, CH2H CF2CH2H CF, CH, H CF3CH2H CF, CH2H CF, CF2CF2 H CF3CF2CF2 H CF, CF, CF, H CF, CF2CF2 H CF2C F2CF2 H (CF,) 2CF H 1 2 CH,CmiCH CH,CmiCH CH,CmiCH CH2C=CH C82CECH CH2Cl. CH,CH2Cl. CH,CH=CH2 CH,C:CH CH2CH2 C)12cCH2cCH3 CH,C1(= CH7 CH , C: CH CH2C) 13 Table 3-A 2 (continued) HCF2 8 CF3) I CF, H CF, H CF, H CH3CH. CF3CF2 H CF3 H CF3CH2H (CF, ), CH)1 CH2CH2CH3 o-CL-benzy It m-CH3-benzy jl! p-CHz-benzy 12 CH20CH. CH2C:CH CH2C:CH CH2C=CH CH2C=CH C)1. cEcH (hereinafter, blank) Table 3-A-2 (continued) 1 R” R” CHs (CPs)zcF H CH,C(J?, H CH2CCz* H CHs CFs H CH,CF, H CH,CF, CHi CH2CPs H CH,CF2 H CH,CF, CH. CH,CF, H CH,CF, H C82CH,CFI H CH2HCF, H CH,HCF2 H CH3HCF2 H CH,HCF2 H 4 1 2 CH2C=CH CH2C :CH CH2C =CH CH,C=C)l C82CECH CH,C:CH CH2C=CH CH,CH. Section 3-B 1 Table 1 CH. CH3 CH3 CH2 CHi CH. CH. CH3 CH2CO2H CH2CO2Na C82CECH3 CH2C0□C21(S C82CECH(CHi)2 CH2Co□CH2CH2CH. CH2CO2CH2(CH2) 2CH2CH2CO□
CH2 (CH2)2CHff Part 3-B Table 1 (Continued) 1 4 5 1 CH3 CH3 CH3 CH3 CH3 CH3 2H5 CH20 day H2C7 H2Br H2I CH(CHI)CH2CH2 CH(CH3)C0□C2H6 CH2C02CH. CH(CH,)CH2CH2 CH20COCH3 CH2C02CH. CH2C0□CH3 CH(CH3)Co2CH3 CH2C0□CH3 CH(CH3)Co2CH3 CH2C=CH CH3 2H5 CH(CH3)2 CH(CH3)2 Table 3-B-1 (continued) 1 CH(SCH,)CO2CO. CH(SC6H5)CO□CH. CH(CH20CH3)CO2CO. CH(CH20CH3)Co□C2H3CH2CO,C
6H6 CH2C0□CH2C6Hs CH2CO□CH2CH2CH2N (CH,). CH2C02-(2-(J)-benzyl)CH2
CH2-(2-F-benzyl)CH2C02CH2
CH2 (CH2)3C02CH3 (CH2)4CO□CH3 (CH2)SCO□CH3 CH20CH. CH20C82CN CH20COCH3 CH20CH2CO□CH3 Table 3-B-1 (continued) I CH(CH,)2 CH2C=CH C) (, (, H6 CH20th CH, (J' H2CN Table 3-B-1 (continued) CH20CH(CH,)Co□CH. CH25CH2CO2CH3 CH2SCH2CH2CO□CH3 CH20CH2CH2Co□CH. CH2C02CH2CH2 CH(CH2)CH2CH2CH,l CH. CH(CH3)C02H CH (CH20CHs)CO2CO. CH(CH20CH3)CH2CH2CH. (Hereinafter, blank space) Chapter 3-B-2 Table R1 1 2 3 R' Rs CH2C0,CH. CH2C02CH2CH3 CH(CH,)CO2CH3 CH(CH3)Co, CH2CN3 CH. CH2C02CH. CH2C0□CH2CH. CH(CH3)C02CH. CH( CH,) CO2CH2CN3 CH. CH2C02CH. CH(CH2)CO2CH2C)l. Table 3-B-2 (continued) 1 2 R"R'R' 1 F2CF2 CF, CF2 CF3CF. CF, CF. CFICF. FsCP2 CFICF2 CH(CHs) 2 CH2C02CH3 CH2C0□CH2CN3 cH(cHw)co□CH1 CH(CH3)CO2CH2CN3 CH(CH2CN,)CO2CH3 CN(CH2CH3)CH3CH2CH. FaCFt CF3CF. CP, CF2CF2 C F, CF, CFI CF, CF, CF. (CF3), CF CH2CN CH20CH. CH. CH,C02CH. CH(CH,)CO2CH2CN. CH. 1 Table 3 B-2 ( 2 3 4 5 r r 02 NO□ 0CH2 0CH2 CH2CN. CH2CN3 CF. CF. Continued) 1 C H2C0□ CH3 CH(CH3)C02CH2CH. CH2C02CH. CH(CH2)CO,CH2CH3 CH2C02CH. CH(CH,)CO2CH,CH3 CH2C02CH. CH(CH2)CO2CH2CN. CH2C0□CH. CH(CH,) CO2CH2CN. CH2C0□CH3 CH( CH3)C0□CH2CH3 CH. CH2C0□CR. CH(CH3)C02CH2CH3 CH. Table 3-B-2 (continued) X R' 2 R3R' (CF,)2CF (CFs), CF CF, CH2 F2CH2 F2CH2 CCZ . CCj'2 Czi CF2 5 1 CH2CO2CH2 CH(CH3)CO2CH2CN3 H3 CH2C02CH3 CH(CH3)CO2CH2CN. CH2 CH2C02CH. CH(CH,)CH3CH2CH. CH2C02CH3 (hereinafter, blank) 3rd-C Rl 1 Table 6 CHNOCH2CO2CH. C(CH2)NOCH2CO□C2H3C(CH20C
H,)NOCH2CO2CH3C(OCH3)NOCH
2CO2C2HsC(CH3)NOCH2CO□C2H
3C(CH20CH,,)NOCH2CO,CH3C(
CH3)NOCH2CO2C2HsC(CH3)NOC
H2Co□C2H3C(CH3)NNC(CH3)Co
2CH3C(OCH3)NNC(CH,)Co2CH3
C(OCH3)NNCHCO2C2H5C(CH3)N
NC(CH3)COC2H5(CH3)NNC(CH3
)Co2CH. Section 3-C Table 1 (continued) 5 6 NH3O2C)(2CH2C)I. N(SO2CH3)2 N(SO2C2Hs)2 N(SO2CH2CH2CH3)2 N(SO2CHs)CHs N(SO2CHs)C4H, - N(SO2CH3)CH20CH3 N(SO2C2H5)CH20CH3 N(SO2C2H6)CH20CH3 N(SO2CH3)2 N(SO2CH3 )2 N(SO2C2H6) 2 N(SO2CHs)2 C(CH3)NOCH2C02CH3 C(CH20CH2)NOCH2CO□C2H3C(O
CHs)NOCH2CO2CHsTable 3-C-1 (continued) 1 4 5 6 C(CH3)NNC(CH2)Co2CH3CH,0C
H2CO□C2H. CH20CH(CH2)Go□C2H5CH20CH(
CH20CH,)CO,CH. CH, 5CH2CO□CH. CH23CH(CHs)CO2C2H5CH2NHCH
2CO2CH. CH2NHCH(CH,)CO2C2H. CH2NHCH(CH20CH,)CO2C2HsCH
20CH2CO2C2Hs CH23CH(CHs)CO2C2HsCH2NHCH
2CO2CH. CH20CH2CO2C2H5 CH2NHCH2Co2CH. NH30□CH. NH302C286 Table 3-C-1 (continued) 1 4 5 6 C(CH,)NOCH2CO,CH. C(CH20CH,)N0CH2CO2C2HsC(O
CH3)NOCH2CO2CH2CH20CH2CO2
CH. CH20CH(CH,)Co2CH. CH25CH, CO2C2H. CH25CH(CH3)Co□CH. CH2NHCH2C02C2H6 CH2NHCH(CH3)CO□CH. N(CH2CH= CH2)SO2CH3N(CH2C
H= CH2)SO2C2H6N(CH2C=CH)S
O□CH. N(CH2C=CH)SO2C2H5 N(COCHz)SO2CH3 N(COC2H5)SO2CH3 NH3O□CH2CH2CH2CH2 Table 3-C-1 (continued) NH3O,CH2Cl(CH,)2 NH3O□CH(,CH3') CH2CH3 N) IS
O□C(CHs)i NH3O,CF. N(So□CF=)z (hereinafter, blank) Table 3-C-1 (continued) Table 3-C-1 (continued) Table 3-C-1 (continued) Table 3-C-1 (continued) Table 3-C-1 (continued) Table 3-C-1 (continued) H3 l sHs Table 3-C-1 (continued) Table 3-C-1 (continued) R1 4 5 6 Table 3-C-1 (continued) 1 4 5 6 Table 3-C-1 (continued) 1 4 5 6 Table 3-C-1 (continued) Table 3-C-2 R1 2H5 C) (2C )I=CH2 CH2C=CH H2CEN CH2C,R5 CH2C=CH C,H. CH2C:CH Table 3-C-3 CH3 2H6 CH=CH2CH. CH2CH=CH2 CH2C=CH CH2CmiCCH8 CH2CmiN H20H H2Cz CH2CO2CH. CH2C02C2H5 C) I20CH3 Table 3-C-2 (continued) 1 4 CH20CH3 CH2C=CH CH=CH2CHs CH(CH,)C: CH CH20CH2CH. CH2CONH2 CH2C02CH3 CH2C02CH2CH3 CH(CH2)CH= CH. Table 3-C-3 (continued) 1 4 C,H. CH2C-R5 2Hs CH2CH=CH2 CH2C=CH CH20CH3 CH2C,R5 CH2C:CH cH2C,Hs Table 3 C-3 (continued) CH. CH. CH. CH. CH. CH. CH. CH3 CH3 CH. CH. CH. CH. CH. CH3 CH. CH(CH,)C: CH CH, CH2C: CH CH(CH3)CH2CH2 CH(CH2)CH= CH2 CH20CH2CH. CH2C820CH- CH(CH2)OCH3 CH(CH3)OCH2CH. o-CHs-benzy II m-CHz-benzyI! 1) -CL-benzy 12 o-CFs-benzy 1 m-CFa-benzy 12 p-CFs -benzy II o-CHz-pheny II m-CHz-pheny 12 3rd-C-4 Table 1 I CH. CH. CH. CH3 CH. CH3 CH. CH. CH3 CH3 CH2 CH. CH3 2Ha CH2CH=CH2 CH2C=CH CH2C,H5 C=Hs H2CEN 2H5 CH2C:CH CH2C,H. CH, CH=CH2 Table 3-C-3 (continued) 1 4 CH. CH. CH. CH3 CH. CH. CH. CH3 CH. CH. p-CHz-pheny II o-C1-phenyll m-(J'-phenyA p-CI!-phenyll o-CFz-pheny II m-CF, -pheny 1 p-CI'5-pheny 1 o-Cf-benzyI ! m-Cf -benzy It p-CII -benzy I Table 3-C-4 (continued) 1 4 CH. CHs CH. CH3 CH. CH. CH. CH. CH3 CH3 CH. CH3 CH. CH2C02C2H5 CH2C=CH CH(CH3)CE CH CH,C: CCH. CH=CH2CEE CH CH(CH3)CH= CH2 CH2CH2CH2 CH(CH,)CH2CH. o-CH3-benzy 1 m-CHz-benzyβ p-CH2-benz y II o- CII -Benzy 12 M -CJ7 -BENZYA P -CJ7 -BENZYJ? Third -C -4 Table CH. Ch. 113ch. CH. CH3ch. Ch. CH3 Ch. CHs-pheny 1! p-CHs-pheny 1 o-CII -pheny 1H m-Cj7-phenyA p-CII -pheny ll CH20CH3 CH20CH2CH. CH(CH,)OCH3 CH(CH,)OCH2CH. CH( CH,)C =CH CH2C:N CH2C,H5 3rd CH3 CH3 CH. CH. CH. CH3 CH. CHs CH. C-5 table (continued) 2H5 2H5 2Hs CH2C82CH. CH(CH3)C: CH CH(CH2)CHs CH2 CH2C0 2CH C,H5 o-CHz-benzy A' m-CHs-benzy II p-CH3-benzy z CH2C=CH. CH2C6H3 CH2C-:N 3-C-5 Table 1 1 CH3 CH. CH3 CH. CH. CH3 CH. CH3 CH3 CH3 CH2 2H- CH20H2CH* CH2C:CH CH20CH3 H2CEN CH20CH3 CH2CE:CH H2CJs CH20CH 3H2C=CH 3-C-6 Table 1 XR'R'R'R'R' 6 C( CH,)NOCH2CO, CI(,CH.C(OC)I*)NOCHzCOzCHzCH-C(C
H,) NNCHCO2CH2CH. CH20CH2COtCH2CH. CHJHCHzCO□CH,CH2 NH30,CH. NH30□C82Cl(.NH30,CH2CH,CH.C(CH,)NOC)I,C02CH,CH3C(CH
s)NOC)IzCOtCHzCHiC(CH20CH
3) NOCH2CO2CH2CH. Table 3 C-6 (continued) 1 2 3 4 5 6 C (CHz)NOCH2CO*CHzCHsNH3O□
CH, CH2Cl. CH20CH2CO2C) 12CHI C(CH3)NOCI(2CO,CH,CH2Table 3 7CF. CF. CF3 CF, CF2 CF 3CF 2 CF, CF2 CF. CF. CF. CF3 CH2C=CH CH2Cl. CH2CH=CH. C H2C: CH CH2CH3 CH2CH=CH2 CH2C=CH CH2C:CH CH2CH3 CH(CH,)C-=CH Part 3 Table C-6 (continued) Table 3-C-8 1 2 3 4 CH2C=CH CH2Cl. CH=CH2CH CH(CHI)C=CH CH20CH. CH2C-H5 CH2C=CH CH2C:CH CH2C=CH CH, CECH CH2C=:CH 3rd R2 CF. CF, CF2 CF3CF2 CF3CF2 CF3CF2 CF2CF2 CF, CF2 CF, CF2 p3cH2 F2CH2 CF , CH. CF, CH2 CF. CF. CF3CF2 czs CF2 8 Table (continued) R″ 4 CH2C=CH CH21,:CH cCH(CHs)C= CH CH2C)I= CH2 CH(CH,)CE CH CH2C4ECH CI( 2C: CH CH, CH2CH3 CH2C=CH CH (CH2)CE CH CH, CH. CH2C82C1h CH2C: CH CH2C-:CH CH2C=CH Table 3-C-9 (continued) CHs CH. CH3 CH3 CH3 CH. CH3 CF , CF2 CF, CF2 CF3 CF3 CF2 C (J'3 C73 CCZ. CH2C=CH CH2C=CH CH2C=CH CH2C::CH CH2C-=CH (hereinafter, blank) No. 3 1 9 Table 1 2 CH3 CH3 CH3 CH3 CH3 CH CH3 CH3 CH3 CH3 CH3 CH3 CF. CF3 CF. CF. CF. CF. CF. CF3 0F. CF3 CF. 3 4 CH2C=CH CH (CH,)C=CH CH2CH. 2 CH2C = CHCH2C = CH2C: CH CH2C: CH CL (2cm CH2C = CH 3 1-10 Table 1 CH3 CH3 CH3 CH3 CH3 CH. CI -F3 CH3 CH3 CH3 CH. CH3 2 CF. CF3 CF CF3 CF3 CF. CF. CF3CF2 CF2 Cz3 3 4 CH2C=CH CH2CH3 CH2C4ECH3 CH2C=CH CH2C=CH CH2C=CH CH2C=CH CH2C=CH CH2C=CH CH2CmiCH Invention When applying compounds as herbicides, Generally, suitable carriers are used, such as solid carriers such as clay, talc, bentonite, diatomaceous earth, and white carbon, or water, alcohols (isopropanol, butanol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, etc.), ethers (anisole, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (N-
methylpyrrolidone, etc.) or halogenated hydrocarbons (chlorobenzene, etc.), and optionally surfactants, emulsifiers, dispersants, penetrants, spreading agents, and thickeners. , an anti-freezing agent, an anti-caking agent, a stabilizer, etc. can be added, and it can be put to practical use in any desired dosage form such as a liquid, emulsion, wettable powder, dry flowable, flowable, powder, or granule preparation. In addition, the compound of the present invention may be used as necessary in formulation or spraying with other herbicides, various insecticides, fungicides, plant growth regulators, etc.
It may also be used in combination with a synergist. As for the types of herbicides to be mixed, for example, see the Farm Chemicals Handbook (Farm Chemicals Handbook).
s Handbook) 1989 edition. The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, cultivated crop, etc., but in general, the amount of active ingredient is 0, OO01-10 per hectare (ha).
Approximately 1 kg, preferably 0.001 to 5 kg. Next, specific formulation examples of formulations using the compounds of the present invention will be shown. However, the formulation examples of the present invention are not limited to these only. In addition, in the following formulation examples, "parts" mean parts by weight. Formulation example 1 Wettable powder Compound of the present invention A-1・・・・・・・・・・・・・・・
・・・・・・・・・・・・50 copies Sieglite PFP...
・・・・・・・・・・・・・・・・・・・・・・・・
Part 43 (Kaolin-based Kreichijikurite Kogyo ■Product name) Tsurupol 5050・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・ 2 parts (Anionic surfactant: Toho Chemical Industry ■Product name) Lunox 1000 C・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・ 3 parts (Anionic surfactant: Toho Chemical Industry ■Product name) Carplex #80 (Anti-caking agent)... 2 parts (White carbon: Shionogi Pharmaceutical ■Product name) Mix and grind the above ingredients uniformly to make a wettable powder. Formulation Example 2 Emulsion Invention Compound A-1・・・・・・・・・・・・・・・・
・・・・・・・・・・・・ Part 3
・・・・・・・・・・・・・・・・・・・・・・・・
...Part 76...
・・・・・・・・・・・・・・・・・・・・・・・・
Part 15 Tsurupol 3005X・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・ 6 parts (mixture of nonionic surfactant and anionic surfactant:
Toho Chemical Industry ■Product name) Mix the above ingredients uniformly to make an emulsion. Formulation example 3 Flowable agent Invention compound A-1・・・・・・・・・・・・・・・
・・・・・・・・・35 parts Ageli Seal S-711
・・・・・・・・・・・・・・・・・・・・・ Part 8 (
Nonionic surfactant: Kao ■Product name) Lunox 10
00 C・・・・・・・・・・・・・・・・・・
・・・・・・0.5 parts (Anionic surfactant: Toho Chemical Industry ■Product name) 1% Rhodobol water・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・20 parts (Thickener: Lawn・
Boulan product name) Ethylene glycol (antifreeze agent)
・・・・・・ 8 parts water・・・・・・・・・－・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
...... 28.5 parts or more are mixed uniformly to form a flowable agent. Formulation example 4 Granular hydrating agent (dry flowable agent) Compound A-1 of the present invention
・・・・・・75 parts isopane Nα1・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・10 parts (Anionic surfactant: Clareisobrene Chemical ■Product name) Vanillex N・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・ 5 parts (Anionic surfactant Nisanyo Kokusaku Valve ■Product name) Carplex #80・・・・・・・・・・・・・・・
...... 10 parts or more (white carbon: Shionogi & Co., Ltd. trade name) are uniformly mixed and pulverized to form a dry flowable agent. Formulation Example 5 Wettable powder Compound B-1 of the present invention...
・・・・・・・・・50 copies Sieglite PFP-・
・−・・−・・・・・・−・・・・−・・・・・・・・・・
・・Part 43 (Kaolin-based Kreichijikurite Kogyo ■Product name) Tsurupol 5050-・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・2 parts (Anionic surfactant: Toho Chemical Industry ■Product name) Lunox 100OC・・・・・・・・・・・・・・・・
・−・・・−・・−・・・・ 3 parts (anionic surfactant: Toho Chemical Industry ■Product name) Carplex #80 (anti-caking agent) 2 parts (
White carbon: Shionogi & Co., Ltd. ■Product name) The above is mixed and pulverized uniformly to make an irrigation agent. Formulation Example 6 Emulsion Compound of the Invention B-1-・・・・・・・・・・・・・
・・・−・・・−Tripartite xylene−・−・・・・・・−・
・・・−・・・−・・−・−・・−・−・76 parts isophorone・・・・−・・・・・・・−・−・・・・・・・・・
−・・−・・−・−・・15 part vine pole 30
05
-6 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■ trade name) or more are mixed uniformly to form an emulsion. Formulation Example 7 Flowable Agent Invention Compound B-1--
・・・・・・・・・・・・ 35 parts Ageli Seal S-
711・・・・・・−・・−・−・−−−−−・・・・
8 parts (Nonionic surfactant: Kao ■Product name) Lunox 100OC・-------------------------------------------------------------------
・−・・・・・・・・・・・0.5 part (anionic surfactant: Toho Chemical Industry ■Product name) 1960 Debord water・・・・・・・・・・・・−−−−−
−−・・−・−・・・20 parts (thickener: Lone Boulin product name) Ethylene glycol (antifreeze agent)・−・・8 parts water・−・・−・・−・・−・
・・・・・・・・・−・・−・・−・・・・・−−−−−
---28.5 parts or more are uniformly mixed to form a flowable agent. Formulation example 8 Granules Compound of the present invention B-1-・・・−・−・・・・・−・−
−−−1・・・−0,1 part bentonite ・・・・−・
−・・−・・・・・−−１−−−−・・・・・
・・・・・・−・55.0 part time −・・・・
・−・・・・・・−・・・・・−−−・・ ・・・・−
- After uniformly mixing and pulverizing 44.9 parts or more, a small amount of water is added and the mixture is stirred and kneaded, granulated using an extrusion granulator, and dried to form granules. Formulation Example 9 Granular hydrating agent (dry flowable agent) Compound B-1 of the present invention...
・・・−・ 75 parts Isopane Nα1・・・・・・−・
・・−・−・・・・・・・・・・・−・・・・・・・・・・
・−・・−10 parts (anionic surfactant: Clareisoprene Chemical ■Product name) Vanillex N・−・・・・・・・・・・・・・・・・・・・・・
・・・・・・−・・−・・ 5 parts (anionic surfactant: Yamaba Kokusaku valve side product name) Carplex #80・・・・・・・・・・・・・・・
..... 10 parts or more (white carbon: Shionogi & Co., Ltd. ■ trade name) are mixed and pulverized uniformly to form a dry flowable agent. Formulation Example 1O Wettable Dispersible Compound of the Invention C-1-----1-----
......1,50 copies Sieglite PFP ---
・・・－・・・・・・－・・・－・・1.・・43 parts (Kaolin-based Crazy Krite Kogyo ■Product name) Tsurupol 5050 ・・−・−・・・・・・・・・・−
・・・・−・・ 2 parts (Anionic surfactant: Toho Chemical Industry ■Product name) Lunox 100Oc ・・・−・−・−・・
-...3 parts (anionic surfactant: Toho Chemical Co., Ltd. ■trade name) Carplex #80 (anti-caking agent) ...2 parts (white carbon: Shionogi & Co., Ltd. ■trade name) or more Mix and grind it evenly to make an irrigation agent. Formulation Example 11 Emulsion Invention Compound C-1・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・3 parts xylene・
・・・−・、・・・−・・・・・・・−・・・・・・・−
・−・−・・・・・・・・・−・76 parts isophorone−・
・・・－・・・・・・－－－－１・・・・・・・・・－・・・
・・・・・・・・・・・・・・・ Part 15 Tsurupol 300
5X・－・・・・・・・・・−・・・・・・・・・・・・
... 6 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■ trade name) or more are mixed uniformly to form an emulsion. Formulation example 12 Flowable agent Invention compound C-1・・・・・・・・・・・・・・・
・・・・・・・・・・・・-35 parts Ageli Seal S-711
...
Nonionic surfactant: Kao ■Product name) Lunox 10
0OC・・・・・・−・・−・・・・・・・・・・・・・・・・
・0.5 part (anionic surfactant: Toho Chemical Industry ■Product name) 1% Rhodobol water -・・・・・・・・・・・・・・・
・・・−・・−・−−20 parts (thickener: Lone Boulin product name) Ethylene glycol (antifreeze agent) – 8 parts Water・・・・・・−・−・・・・・・・・・・・・・・・・
・−・・・・・・・・・・−・−・・・・・・・・・・
... 28.5 parts or more are mixed uniformly to form a flowable agent. Formulation example 13 Granules Compound of the present invention C-1・・・・・・・・・・・・・・・・・・・
・・・・・・・・・−0,1 part bentonite −・・・
・・・・・・−・−・・・・・・・・・・・・・・・・・・・
-55,0 parts talc-・-・・・・・・・・・・・・・・
・−・・−・−・−−−−−・−・・・・・・・・・・
- After uniformly mixing and pulverizing 44.9 parts or more, add a small amount of water, stir and knead, granulate with an extrusion granulator, and dry to form granules. Formulation Example 14 Granular hydrating agent (dry flowable agent) Compound C-1 of the present invention
・・・・−75 parts Isopane Nα1 ・−・・・・・・・
−・・・・・・−・・−−−−−−−・・−・−1
0 parts (Anionic surfactant: Clarei Sobrene Chemical ■Product name) Vanilex N・・・・・・・・・・・・・・・・・・・・・
・・・・・・−・・・−・・・・・・・・・・5 parts (Anionic surfactant: Sanyo Kokusaku Pulp ■Product name) Carplex #80 ・・・・・・・・・・・・−・・
・−・−−10 parts (White Carbon: Shionogi & Co., Ltd.■
Product name) The above is mixed and pulverized uniformly to make a dry flowable agent. When used, the above-mentioned wettable powders, emulsions, flowable powders, and granular wettable powders are diluted 50 to 1000 times with water and sprayed at a concentration of 0.0001 to 10 kg of the active ingredient per hectare (ha). Next, the usefulness of the compounds of the present invention as herbicides will be specifically explained in the following test examples. Test Example-1 Weeding effect test by soil treatment Sterilized diluvial soil was placed in a plastic box measuring 15 cm in length, 22 cm in width, and 6 cm in depth. Soybeans and cotton were mixed and covered with soil to a depth of about 1 cm, and then the active ingredients were uniformly sprayed onto the soil surface using a small sprayer in a predetermined ratio. The chemical solution used for spraying was a formulation suitably prepared according to the formulation example described above, diluted with water, and used for spraying. Three weeks after spraying the chemical solution, the herbicidal effects on various weeds and crops were investigated according to the following criteria. The results are shown in Table 4-A-1, Table 4-A-2, and Table 4-A-1.
It is shown in Table B, Table 4-C-1 and Table 4-C-2. Judgment Criterion 5: Weed killing rate 90% or more (almost complete death) 4.
...Weed killing rate 70-90% 3...Weed killing rate 40-70% 2...Weed killing rate 20-40% 1...Weed killing rate 5-20% 0...Weed killing rate 5% or less (dove) However, the above herbicide rate was determined by the following formula by determining the weight of above-ground plants in the chemical-treated area and the weight of above-ground plants in the untreated area. Test Example-2 Weeding effect test by foliar treatment Sterilized diluvial soil was placed in a plastic box measuring 15 cm long, 22 cm wide, and 6 cm deep, and the fields were placed in a plastic box measuring 15 cm in length, 22 cm in width, and 6 cm in depth. , soybean, cotton, and beet seeds were sown in spots and covered with soil to a depth of about 1 cm. When each plant reached the 2-3 leaf stage, the active ingredient was uniformly sprayed onto the stems and leaves so that the amount of the active ingredient was at a predetermined ratio. The chemical solution used for spraying was prepared as appropriate according to the formulation examples described above, diluted with water, and sprayed over the entire surface of the stems and leaves of various weeds using a small sprayer. Four weeks after spraying the chemical solution, the herbicidal effect on various weeds and crops was investigated according to the criteria of Test Example-1. The results are shown in Table 5-A-1, Table 5-A-2, Table 5-B, Table 5-C-1 and Table 5-C-2. Test Example-3 Weeding effect test under flooded conditions 115000
After putting alluvial soil in Earl's Hugner pot, water is added and mixed to create a freshwater condition with a water depth of 2 cm. Seeds of Japanese millet, Konagi, Gikashigusa, and Firefly were mixedly sown in the above pots, and tubers of Mizukayatsu and Urikawa were placed in the beds, and then rice seedlings at the 2.5-leaf stage were transplanted. The pots were placed in a greenhouse at 25 to 30°C to grow the plants, and 28 days after sowing, a diluted drug solution was dropped onto the water surface using a measuring pipette to a predetermined dose. Test example-1: Herbicidal effect on rice and various weeds 3 weeks after dropping the chemical solution
The investigation was conducted according to the criteria. The results are shown in Table 6. The symbols in each table have the following meanings. -1 Table 4-A-1 0 0 0 55555 55555 55555 (Hereafter, blank) B (Beat) Comparative control compounds are shown below. Table 4-A 2 Table 4 A-2 (continued) -3 0 0 0 55555521101 55555543202 5555555504 A-104022452501000 8034554512111 16035555524324 -4 0 0 0 55555 501022 55555512133 55555534344 -12 1033554533201 2044555544312 4055555555424 -6 0 0 55555533111 55555544222 55555555434 -14 10 5 5 5 5 5 5 5
5 5 2 420 5 5 5
5 5 5 5 5 5 3 540
5 5 5 5 5 5 5 5
5 4 5A-8 40 0 60 35555510000 45555521100 55555533212 -16 10 5 5 5 5 5 5 5
5 5 2 520 5 5 5 5
5 5 5 5 5 3 540
5 5 5 5 5 5 5 5 5
4 5 4th A Table 2 (continued) -20 0 0 0 55555523212 55555534323 55555545434 0 0 55555535503 55555545514 55555555535 -32 0 0 55355524102 554 55535214 55555545525 (hereinafter, blank space) Table 4-C-1 0 0 0 45555 55555 55555 4th -C-2 Table 0 0 55555501000 55555502100 55555513200 -B -1 10555555000024 20555555110035 (Hereafter, margin) 5-A-1 Table-1 0 0 0 55555 55555 55555 (Hereafter, margin ) Table 5-A-2 No. 5 -A-2 Table (continued) 0 0 0 535555442445 545555554555 555555555555 A-10402155321122528032554
4223353 160535555444453 -4 10345555422555 20455555533555 40555555544555 A-12104355552323542054555
5343455 40555555454555 -6 10225555322455 20445555432555 40555555543555 A-14105555555555552055555
5555555 40555555555555 40 0 60 025555010211 125555021222 235555132332 A-16105555555555552055555
5555555 40555555555555 Table 5-A-2 (continued) Table 5-B Table-20 -22 0 0 0 0 0 323554433353 434555544454 545555555555 333554545553 444555555554 5 55555555555 B-110555555210155 20555555321255 (below, margin) -32 0 0 335555445554 445555555555 555555555555 (below) , margin) Table 5-C-1 0 0 5 5 5 5 5 5 5 5 Comparative control compound 0 Table 5-C-2 0 0 215555020555 425555131555 535555332555 -1 2 -3 5 0 2,

Claims (5)

[Claims] (1) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 represents a hydrogen atom, a C_1 to C_3 alkyl group, a hydroxymethyl group, or a C_1 to C_3 haloalkyl group, and R ^2 represents a C_1 to C_6 haloalkyl group, R^3
is a hydrogen atom, C_1 to C_6 alkyl group, C_1 to C_
6 represents a haloalkyl group, hydroxymethyl group, halogen atom or nitro group, R^4 represents a hydrogen atom or a halogen atom, R^5 represents a halogen atom, nitro group or cyano group, R^6 represents -S- B^1 [However, B^1 is a hydrogen atom, C_
1-C_5 alkyl group, C_3-C_6 cycloalkyl group, C_2-C_4 alkenyl group, C_3-C_4 alkynyl group, cyanomethyl group, hydroxymethyl group, chloromethyl group, benzyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, B^2^1
represents a hydrogen atom, a C_1 to C_3 alkyl group, a methylthio group, a phenylthio group, or a methoxymethyl group, and B^
2^2 is a hydrogen atom, sodium atom, potassium atom, ammonium group, isopropylammonium group, C_1~
C_3 alkyl group, C_2-C_5 alkenyl group, C_
3-C_5 alkynyl group, C_3-C_6 cycloalkyl group, (C_3-C_6 cycloalkyl) C_1-C_
2-alkyl group, C_2-C_3 haloalkyl group, phenethyl group, α-methylbenzyl group, 3-dimethylaminopropyl group, phenyl group optionally substituted with one or more substituents (however, the substituent is a halogen atom) , C_1-C_4 alkyl group, C_1-C_3 alkoxy group, C_1-C_2 alkylamino group, dimethylamino group, (C_1-C_2 alkoxy) carbonyl group, C
Represents a _2-C_3 acyl group, a C_1-C_2 haloalkyl group, and a C_1-C_2 haloalkyloxy group. ) or a benzyl group which may be substituted with one or more substituents (however, the substituents are halogen atoms, C_1
~C_4 alkyl group, C_1-C_3 alkoxy group, C
_1-C_2 alkylamino group, dimethylamino group, C
_2-C_3 acyl group, trifluoroacetylamino group, (C_1-C_2 alkoxycarbonyl group, methylsulfonyl group, trifluoromethylsulfonyl group, C_1
~C_2 represents a haloalkyl group, C_1 to C_2 haloalkyloxy group. ) represents. ], ▲ Numerical formulas, chemical formulas, tables, etc. ▼CO_2B^2^2 [However, B^2^2 represents the same meaning as above, and n represents an integer from 1 to 4. ]
, CH_2-Y-B^2^3 [However, B^2^3 is a hydrogen atom, C_1 to C_5 alkyl group, cyanomethyl group, C
_2 to C_5 represents an acyl group, chloroacetyl group or dimethylcarbamoyl group, and Y represents an oxygen atom or a sulfur atom. ], CH_2-Y-CH(B^2^1)CO
_2B^2^2 [However, B^2^1, B^2^2 and Y represent the same meanings as above. ] or ▲ Numerical formulas, chemical formulas, tables, etc. ▼CO_2B^2^2 [However, B^2^2, n and Y represent the same meanings as above. ]
represents. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^1
is a hydrogen atom, C_1 to C_3 alkyl group, C_1 to C_
3 alkoxy group or (C_1-C_3 alkoxy)C
_1 to C_2 represents an alkyl group, and D^2^2 represents a hydrogen atom, a C_1 to C_4 alkyl group, a C_3 to C_6 cycloalkyl group, a C_2 to C_3 haloalkyl group, a phenyl group, or a benzyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼[However, D^2^1 and D^2^2 represent the same meanings as above, and D^2^3 represents a hydrogen atom or C_
1 to C_3 represents an alkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^2
represents the same meaning as above, D^2^4 is a hydrogen atom, C
It represents a _1-C_3 alkyl group or a (C_1-C_3 alkoxy)C_1-C_2 alkyl group, and Z represents an oxygen atom, a sulfur atom, or NH. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^5
represents a hydrogen atom, a sodium atom, a C_1-C_4 alkyl group, a C_2-C_5 alkenyl group, a C_3-C_5 alkynyl group, a C_2-C_5 acyl group, a C_1-C_4 alkylsulfonyl group, or a (C_1-C_3 alkoxy)C_1-C_2 alkyl group. represents, D^2^6 is C_
Represents a 1-C_4 alkyl group or a C_1-C_3 haloalkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^7 is a hydrogen atom, C_1 to C_6 alkyl group, C_3 to C_6 cycloalkyl group, C_1 to C_
3 haloalkyl group, C_1-C_4 alkoxy group, C_
1-C_4 alkylthio group, (C_1-C_4 alkoxy) carbonyl group, mercapto group, hydroxyl group, (C_1-
C_3 alkoxy) C_1-C_2 alkyl group, C_1
~C_4 alkylamino group, ND2^2^8 (D^2^
9) (However, D^2^8 and D^2^9 each independently represent a C_1 to C_4 alkyl group.), dimethylcarbamoyl group, CONHSO_2CH_
3, C_1-C_4 alkylsulfonyl group or N(D
^3^0) SO_2D^3^1 (However, D^3^0 is a hydrogen atom, a sodium atom, a C_1 to C_4 alkyl group,
C_1-C_4 alkylsulfonyl group, (C_1-C_
3 alkoxy) represents a C_1-C_2 alkyl group, D^
3^1 is a C_1 to C_4 alkyl group or C_1 to C_
Represents a 3-haloalkyl group. ) represents. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^2 represents a C_1 to C_6 alkyl group or a C_3 to C_6 cycloalkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^3, D^3^4 and D^3^5 each independently represent a hydrogen atom or a C_1 to C_6 alkyl group. ]、▲Mathematical formulas, chemical formulas, tables, etc.▼、▲
There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^6 and D^3^7 each independently represent a hydrogen atom, a C_1 to C_6 alkyl group, or a dimethylamino group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc.
C_6 cycloalkyl group, C_1-C_3 haloalkyl group, C_1-C_4 alkoxy group, C_1-C_4 alkylthio group, (C_1-C_4 alkoxy) carbonyl group, dimethylcarbamoyl group, (C_1-C_3 alkoxy)C_1-C_2 alkyl group, C_1- C_4 alkylamino group, ND^2^8 (D^2^9) (however, D
^2^8 and D^2^9 represent the same meanings as above. ), CONHSO_2CH_3, C_1-C_4 arlesulfonyl group, phenyl group, benzyl group or N(D^
3^9) SO_2D^3^1 (However, D^3^1 represents the same meaning as above, D^3^9 is a hydrogen atom, C_1~
C_4 alkyl group, sodium atom, potassium atom, C
_1-C_4 alkylsulfonyl group or (C_1-C
_3 alkoxy) represents a C_1-C_2 alkyl group. ) represents. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ [However, D^4^0 is a hydrogen atom, C_1 to C_6 alkyl group, C_3 to C_6 cycloalkyl group, phenyl group,
Represents a benzyl group or 2-pyridyl group, and D^4^1 is a hydrogen atom, a halogen atom, a mercapto group, a hydroxyl group, an amino group, a C_1 to C_6 alkyl group, a C_1 to C_4 alkylamino group, and ND^2^8 (D ^2^9) (However, D
^2^8 and D^2^9 represent the same meanings as above. ), C_1-C_4 alkylthio group, CO_2D^2^
8 (however, D^2^8 represents the same meaning as above),
C_1-C_4 alkylsulfonyl group, C_1-C_4
Alkoxy group or N(D^3^9)SO_2D^3^
1 (however, D^3^1 and D^3^9 represent the same meanings as above), and D^4^2 is a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, C_1 ~C_
4 alkylamino group, N(D^2^8)D^2^9 (however, D^2^8 and D^2^9 represent the same meanings as above), C_1 to C_4 alkylcarbonyl group, or (C_1-C_4 alkoxy) represents a carbonyl group. ]
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^4^3 is a hydrogen atom, a hydroxyl group, a methoxy group,
It represents an amino group, a benzoyl group, or a C_1-C_4 alkyl group, and D^4^4 represents a hydrogen atom, a cyano group, an acetyl group, a C_1-C_4 alkyl group, a carboxyl group, or a (C_1-C_4 alkoxy) carbonyl group. ]
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^4^5 and D^4^6 each independently represent a hydrogen atom, phenyl group, hydroxyl group, methoxy group, or C_1
~C_4 represents an alkyl group. ] or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, D^4^7 and D^4^8 are each independently,
Represents a hydrogen atom or a C_1 to C_4 alkyl group. ] represents. X represents an oxygen atom or a sulfur atom. However, when R^5 and R^6 form a ring, formula (II),
Formula (IV-1), Formula (IV-2), Formula (IV-3) or Formula (
IV-4) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-2) ▲ Mathematical formulas, There are chemical formulas, tables, etc. ▼ (IV-3) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-4) [In the formula, R^1, R^2, R^3, R^4 and X are the same as above. , A^1 represents a hydrogen atom or a C_1-C_4 alkyl group, and A^2 represents a hydrogen atom, a C_1-C_5 alkyl group, C_2
~C_5 alkenyl group, C_3-C_5 alkynyl group,
(C_3-C_6 cycloalkyl) C_1-C_2 alkyl group, C_1-C_6 haloalkyl group, C_1-C_
6-haloalkenyl group, C_1-C_6 haloalkynyl group, cyanomethyl group, hydroxymethyl group, chloromethyl group, (C_1-C_3 alkoxy)C_1-C_2 alkyl group, -CH_2CO_2A^2^1 [However, A^2
^1 represents a hydrogen atom, a C_1 to C_5 alkyl group, a sodium atom, a phenyl group optionally substituted with a halogen atom, or a benzyl group optionally substituted with a halogen atom. ], -CH_2CON(A^2^2)A^2
^3 [However, A^2^2 and A^2^3 each independently represent a hydrogen atom or an alkyl group of C_1 to C_3. ], an optionally substituted phenyl group (however, the substituent represents a C_1-C_4 alkyl group, a C_1-C_4 haloalkyl group, a C_1-C_4 alkoxy group, or a halogen atom), an optionally substituted benzyl group (However, substituents are C_1 to C_4 alkyl groups, C_1 to C_4
Haloalkyl group, C_1-C_4 alkoxy group, (C_
1-C_4 alkoxy) carbonyl group, (C_1-C_
3 alkoxy) C_1 to C_2 alkyl group, represents a halogen atom. ) or -CH_2A^2^4 [However, A^
2^4 is an optionally substituted 2-pyridyl group (however,
The substituent represents a C_1 to C_4 alkyl group or a halogen atom. ), an optionally substituted 2-pyridazyl group (
However, the substituent represents a C_1 to C_4 alkyl group or a halogen atom. ), represents a 3-isothiazole group or a 3-isoxazole group. ], J is a hydrogen atom, C_1-C_4 alkyl group, C_2-C
_4 alkenyl group, C_3-C_4 alkynyl group, hydroxymethyl group, chloromethyl group, carbamoylmethyl group, cyanomethyl group, (C_1-C_4 alkoxy)carbonylmethyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, C_3-C_6 cyclo There are alkyl groups, ▲mathematical formulas, chemical formulas, tables, etc.▼,
(C_3-C_6 cycloalkyl) C_1-C_2 alkyl group, (C_1-C_2 alkoxy) C_1-C_2
Alkyl group, optionally substituted phenyl group (however,
The substituent represents a C_1-C_4 alkyl group, a C_1-C_4 alkoxy group, a (C_1-C_4 alkoxy) carbonyl group, a (C_1-C_4 alkoxy)C_1-C_2 alkyl group, or a halogen atom. ) or an optionally substituted benzyl group (however, the substituent is a C_1-C_4 alkyl group, a C_1-C_4 alkoxy group, (C_1-C_
4 alkoxy) carbonyl group, (C_1-C_4 alkoxy) C_1-C_2 alkyl group, and a halogen atom. ) represents. ] Represented by . ] Uracil derivative represented by. (2) Formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, R^1 represents a hydrogen atom, a C_1 to C_3 alkyl group, a hydroxymethyl group, or a halomethyl group, and R^
2 represents a C_1 to C_6 haloalkyl group, R^3 represents a hydrogen atom, a C_1 to C_6 alkyl group, a C_1 to C_6 haloalkyl group, a hydroxymethyl group, a halogen atom or a nitro group, and R^4 represents a hydrogen atom or a halogen atom , A^1 represents a hydrogen atom or a C_1-C_4 alkyl group, A^2 represents a hydrogen atom, a C_1-C_5 alkyl group, C_2
~C_5 alkenyl group, C_3-C_5 alkynyl group,
(C_3-C_6 cycloalkyl) C_1-C_2 alkyl group, C_1-C_6 haloalkyl group, C_1-C_
6-haloalkenyl group, C_1-C_6 haloalkynyl group, cyanomethyl group, hydroxymethyl group, chloromethyl group, (C_1-C_3 alkoxy)C_1-C_2 alkyl group, -CH_2CO_2A^2^1 [However, A^2
^1 represents a hydrogen atom, a C_1 to C_5 alkyl group, a sodium atom, a phenyl group optionally substituted with a halogen atom, or a benzyl group optionally substituted with a halogen atom. ], -CH_2CON(A^2^2)A^2
^3 [However, A^2^2 and A^2^3 each independently represent a hydrogen atom or an alkyl group of C_1 to C_3. ], an optionally substituted phenyl group (however, the substituent represents a C_1-C_4 alkyl group, a C_1-C_4 haloalkyl group, a C_1-C_4 alkoxy group, or a halogen atom), an optionally substituted benzyl group ( however,
Substituents include C_1-C_4 alkyl group, C_1-C_4 haloalkyl group, C_1-C_4 alkoxy group, (C_1
~C_4 alkoxy) carbonyl group, (C_1~C_3
alkoxy) C_1 to C_2 alkyl group, represents a halogen atom. ) or -CH_2A^2^4 [However, A^2
^4 is an optionally substituted 2-pyridyl group (however, the substituent represents a C_1 to C_4 alkyl group or a halogen atom), an optionally substituted 2-pyridazyl group (however, the substituent is C_1 to C_4 represents an alkyl group or a halogen atom), a 3-isothiazole group or a 3-isoxazole group], and X represents an oxygen atom or a sulfur atom. The uracil derivative according to claim 1, which is represented by: (3) Formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) [In the formula, R^1 represents a hydrogen atom, a C_1 to C_3 alkyl group, a hydroxymethyl group, or a halomethyl group, and R^
2 represents a C_1 to C_6 haloalkyl group, R^3 represents a hydrogen atom, a C_1 to C_6 alkyl group, a C_1 to C_6 haloalkyl group, a hydroxymethyl group, a halogen atom or a nitro group, and R^4 represents a hydrogen atom or a halogen atom , R^5 represents a halogen atom, nitro group or cyano group, B^1 is a hydrogen atom, C_1 to C_5 alkyl group, C_3
~C_6 cycloalkyl group, C_2-C_4 alkenyl group, C_3-C_4 alkynyl group, cyanomethyl group, hydroxymethyl group, chloromethyl group, benzyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas, tables, etc. There are ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, B^2^1
represents a hydrogen atom, a C_1 to C_3 alkyl group, a methylthio group, a phenylthio group, or a methoxymethyl group, and B^
2^2 is a hydrogen atom, sodium atom, potassium atom, ammonium group, isopropylammonium group, C_1~
C_5 alkyl group, C_2-C_5 alkenyl group, C_
3-C_5 alkynyl group, C_3-C_6 cycloalkyl group, (C_3-C_6 cycloalkyl) C_1-C_
2-alkyl group, C_2-C_3 haloalkyl group, phenethyl group, α-methylbenzyl group, 3-dimethylaminopropyl group, phenyl group optionally substituted with one or more substituents (however, the substituent is a halogen atom) , C_1-C_4 alkyl group, C_1-C_3 alkoxy group, C_1-C_2 alkylamino group, dimethylamino group, (C_1-C_2 alkoxy) carbonyl group, C
Represents a _2-C_3 acyl group, a C_1-C_2 haloalkyl group, and a C_1-C_2 haloalkyloxy group. ) or a benzyl group which may be substituted with one or more substituents (however, the substituents are halogen atoms, C_1
~C_2 alkyl group, C_1-C_3 alkoxy group, C
_1-C_2 alkylamino group, dimethylamino group, C
_1-C_3 acyl group, trifluoroacetylamino group, (C_1-C_2 alkoxy)carbonyl group, methylsulfonyl group, trifluoromethylsulfonyl group, C_
Represents a 1-C_2 haloalkyl group and a C_1-C_2 haloalkyloxy group. ) represents. ]、▲There are mathematical formulas, chemical formulas, tables, etc.▼CO_2B^2^2 [However, B^2^2
represents the same meaning as above, and n represents an integer of 1 to 4. ], CH-Y-B^2^3 [However, B^2^3 is a hydrogen atom, C_1 to C_5 alkyl group, cyanomethyl group, C_
2 to C_5 represents an acyl group, chloroacetyl group or dimethylcarbamoyl group, and Y represents an oxygen atom or a sulfur atom. ], CH2-Y-CH (B^2^1CO_2B
^2^2 [However, B^2^1, B^2^2 and Y represent the same meanings as above. ] or ▲ Numerical formulas, chemical formulas, tables, etc. ▼CO_2B^2^2 [However, B^2^2, n and Y represent the same meanings as above. ]
, X represents an oxygen atom or a sulfur atom. The uracil derivative according to claim 1, which is represented by: (4) Formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) [In the formula, R^1 represents a hydrogen atom, a C_1 to C_3 alkyl group, or a C_1 to C_3 haloalkyl group, and R^2 represents C_1 ~C_6 represents a haloalkyl group, R^3 represents a hydrogen atom, a C_1 to C_6 alkyl group, a C_1 to C_6 haloalkyl group, a hydroxymethyl group, a halogen atom or a nitro group, R^4 represents a hydrogen atom or a halogen atom, R^5 represents a halogen atom, nitro group, or cyano group, and D^1 has a ▲ mathematical formula, chemical formula, table, etc. ▼ [However, D^2^1
is a hydrogen atom, C_1 to C_3 alkyl group, C_1 to C_
3 alkoxy group or (C_1-C_3 alkoxy)C
_1 to C_2 represents an alkyl group, and D^2^2 represents a hydrogen atom, a C_1 to C_4 alkyl group, a C_2 to C_6 cycloalkyl group, a C_2 to C_3 haloalkyl group, a phenyl group, or a benzyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼[However, D^2^1 and D^2^2 represent the same meanings as above, and D^2^3 represents a hydrogen atom or C_
Represents a 1-C_3 alkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^2
represents the same meaning as above, D^2^4 is a hydrogen atom, C
It represents a _1-C_3 alkyl group or a (C_1-C_3 alkoxy)C_1-C_2 alkyl group, and Z represents an oxygen atom, a sulfur atom, or NH. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^5
represents a hydrogen atom, a sodium atom, a C_1-C_4 alkyl group, a C_2-C_5 alkenyl group, a C_3-C_5 alkynyl group, a C_2-C_5 acyl group, a C_1-C_4 alkylsulfonyl group, or a (C_1-C_3 alkoxy)C_1-C_2 alkyl group. represents, D^2^6 is C_
Represents a 1-C_4 alkyl group or a C_1-C_3 haloalkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc.▼,▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^2^7 is a hydrogen atom, C_1 to C_6 alkyl group, C_1 to C_6 cycloalkyl group, C_1 to C_
3 haloalkyl group, C_1-C_4 alkoxy group, C_
1-C_4 alkylthio group, (C_1-C_4 alkoxy) carbonyl group, mercapto group, hydroxyl group, (C_1-
C_3 alkoxy) C_1-C_2 alkyl group, C_1
~C_4 alkylamino group, ND^2^8 (D^2^9
) (However, D^2^8 and D^2^9 each independently represent a C_1 to C_4 alkyl group. ), dimethylcarbamoyl group, CONHSO_2CH_
3, C_1-C_4 alkylsulfonyl group or N(D
^3^0) SO_2D^3^1 (However, D^3^0 is a hydrogen atom, a sodium atom, a C_1 to C_4 alkyl group,
C_1-C_4 alkylsulfonyl group, (C_1-C_
3 alkoxy) represents a C_1-C_2 alkyl group, D^
3^1 is a C_1 to C_4 alkyl group or C_1 to C_
Represents a 3-haloalkyl group. ) represents. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^2 represents a C_1 to C_6 alkyl group or a C_3 to C_6 cycloalkyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^3, D^3^4 and D^3^5 each independently represent a hydrogen atom or a C_1 to C_6 alkyl group. ]、▲Mathematical formulas, chemical formulas, tables, etc.▼、▲
There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^3^6 and D^3^7 each independently represent a hydrogen atom, a C_1 to C_6 alkyl group, or a dimethylamino group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc.
C_6 cycloalkyl group, C_1-C_3 haloalkyl group, C_1-C_4 alkoxy group, C_1-C_4 alkylthio group, (C_1-C_4 alkoxy) carbonyl group, dimethylcarbamoyl group, (C_1-C_3 alkoxy)C_1-C_2 alkyl group, C_1- C_4 alkylamino group, ND^2^8 (D^2^9) (however, D
^2^8 and D^2^9 represent the same meanings as above. ), CONHSO_2CH_3, C_1-C_4 alkylsulfonyl group, phenyl group, benzyl group or N(D
^3^9) SO_2D^3^1 (However, D^3^1 represents the same meaning as above, D^3^9 is a hydrogen atom, C_1
~C_4 alkyl group, sodium atom, potassium atom,
C_1-C_4 alkylsulfonyl group or (C_1-
C_3 alkoxy) represents a C_1-C_2 alkyl group. ) represents. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ [However, D^4^0 is a hydrogen atom, C_1 to C_6 alkyl group, C_3 to C_6 cycloalkyl group, phenyl group,
Represents a benzyl group or 2-pyridyl group, and D^4^1 is a hydrogen atom, a halogen atom, a mercapto group, a hydroxyl group, an amino group, a C_1 to C_6 alkyl group, a C_1 to C_4 alkylamino group, and ND^2^8 (D ^2^9) (However, D
^2^8 and D^2^9 represent the same meanings as above. ), C_1-C_4 alkylthio group, CO_2D^2^
8 (however, D^2^8 represents the same meaning as above),
C_1-C_4 alkylsulfonyl group, C_1-C_4
Alkoxy group or N(D^3^9)SO_2D^3^
1 (however, D^3^1 and D^3^9 represent the same meanings as above), and D^4^2 is a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, C_1 ~C_
4 arlylamino group, N(D^2^8)D^2^9 (however, D^2^8 and D^2^9 represent the same meanings as above), C_1 to C_4 alkylcarbonyl group, or (
Represents C_1-C_4 alkoxy) carbonyl group. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^4^3 is a hydrogen atom, a hydroxyl group, a methoxy group,
It represents an amino group, a benzoyl group, or a C_1-C_4 alkyl group, and D^4^4 represents a hydrogen atom, a cyano group, an acetyl group, a C_1-C_4 alkyl group, a carboxyl group, or a (C_1-C_4 alkoxy) carbonyl group. ]
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, D^4^5 and D^4^6 each independently represent a hydrogen atom, phenyl group, hydroxyl group, methoxy group, or C_1
~C_4 represents an alkyl group. ] or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [However, D^4^7 and D^4^8 are each independently,
Represents a hydrogen atom or a C_1 to C_4 alkyl group. ], and X represents an oxygen atom or a sulfur atom. However, when R^5 and D^1 form a ring, the formula (IV-1
), formula (IV-2), formula (IV-3) or formula (IV-4)▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-2) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV-3) ▲ Mathematical formulas, chemical formulas, tables, etc. etc.▼(IV-4) [In the formula, R^1, R^2, R^3, R^4 and X represent the same meanings as above, J is a hydrogen atom, C_1 to C_4
Alkyl group, C_2-C_4 alkenyl group, C_3-C
_4 Alkynyl group, hydroxymethyl group, chloromethyl group, carbamoylmethyl group, cyanomethyl group, (C_1
~ C_4 alkoxy) carbonylmethyl group, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, C_3 ~ C_6 cycloalkyl groups, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (C_3 ~ C
_6 cycloalkyl) C_1-C_2 alkyl group, (C
_1-C_2 alkoxy) C_1-C_2 alkyl group,
An optionally substituted phenyl group (however, the substituent is C_
1 to C_4 alkyl group, C_1 to C_4 alkoxy group,
(C_1-C_4 alkoxy) carbonyl group, (C_1
~C_4 alkoxy) C_1 to C_2 alkyl group, represents a halogen atom. ) or an optionally substituted benzyl group (however, the substituent is a C_1-C_4 alkyl group, C_
1-C_4 alkoxy group, (C_1-C_4 alkoxy) carbonyl group, (C_1-C_4 alkoxy)C_1
~C_2 represents an alkyl group or a halogen atom. ) represents. ] Represented by . The uracil derivative according to claim 1, which is represented by: (5) A herbicide containing the uracil derivative according to claim 1 as an active ingredient.