JPH0525173A - Condensed pyrimidinedione derivative and herbicide - Google Patents

Abstract

PURPOSE:To obtain the subject new compound useful as a selective herbicide with hardly any toxicity to crops. CONSTITUTION:A compound expressed by formula I [R<4> is H or halogen; R<5> is halogen or nitro; R<6> is H, halogne, mercapto, amino, CO2A<1> (A<1> is H, 1-6C alkyl, OA<2> (A<2> is H, 1-6C alkyl, 3-6C alkenyl, etc.), etc.; Q is formula II, III (q<1> to q<6> and q<15> to q<18> are H, halogen or methyl; X is O or S), etc.], e.g. 2-(4- chloro-5-ethoxycarbonyl-2-fluorophenyl)-5,6,7-trihydro-2H,8H-pyrrolo[1 ,2-C]- pyrimidine-1,3-dione. The compound expressed by formula I is obtained by reacting an isopropylidene malonate derivative expressed by formula IV with a phenyl iso(thio)cyanate expressed by formula V.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel fused pyrimidinedione derivative and a selective herbicide containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, many herbicides have been put into practical use in order to protect important crops such as rice, soybean, wheat, corn, cotton and beet from weeds and to improve the productivity of these important crops. . However, there is still a need for new and better herbicides. That is, those having a high herbicidal effect at a low dosage (especially, it is necessary to kill weeds by spraying as low a dosage as possible from the viewpoint of environmental protection), those having an appropriate residual effect (in recent years, soil). It has been a problem that long-term residual drugs damage the succeeding crops, and it is important that they show appropriate residual effects after spraying.) Those that kill weeds immediately after spraying (drug After treatment, the next crop can be sown and transplanted in a short period of time.) The number of times of chemical treatment is small (it is important for farmers to minimize the number of complicated weed control work). , A wide range of weed control targets (for broad-leaved weeds, gramineous weeds, perennial weeds, and other weed species with different properties, it is desirable to use a single agent to control these weeds), and many application methods (Soil treatment effect, foliage treatment effect, etc. A stronger weeding effect can be obtained by holding it.) Those that do not show harmful chemical damage to crops (only weeds can be selectively killed in arable land where crops and weeds are mixed) Those having high safety (those having low human-human toxicity and having little crop residue) are desired.

On the other hand, it is known that a specific compound of the uracil derivative exhibits herbicidal activity. For example, The Pesticide Manual No. 8
Edition, p. 89, The British Crop Protection Council
(1987) and the like describe bromacil as one of the herbicides having a uracil skeleton. In addition, JP-A-63-107967, JP-A-63-41466, and JP-A-61-221178.
U.S. Pat. No. 3,869,457, U.S. Pat. No. 39
No. 81715 and WO 88/10254 disclose uracil derivatives having a herbicidal action.

[0004]

In view of such a situation, the present inventors show selectivity for important crops and have excellent herbicidal effect against many weeds with a low dose. As a result of continued research to develop a herbicide having both soil treatment and foliar treatment effect, formula (I)

[0005]

[Chemical 5]

[In the formula, R ⁴ represents a hydrogen atom or a halogen atom, R ⁵ represents a halogen atom or a nitro group, and R ⁶ represents a hydrogen atom, a halogen atom, a mercapto group, an amino group, CO ₂ A ¹ (A ¹ Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), OA ² (A ² is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or 3 to 6 carbon atoms).
And an alkynyl group having 3 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. ), O
CHA ³ CO ₂ A ⁴ (A ³ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, A ⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), SCHA ³ CO
₂ A ⁴ (A ³ and A ⁴ have the same meanings as described above), NHCHA ³ CO ₂ A ⁴ (A ³ and A ⁴ have the same meanings as described above) or NHCO ₂ A ⁵ (A
⁵ represents an alkyl group having 1 to 6 carbon atoms, a phenyl group which may be substituted, or a benzyl group which may be substituted by a phenyl ring. ), And Q is the formula

[0007]

[Chemical 6]

(Wherein q ¹ , q ² , q ³ , q ⁴ , q ⁵ , q
⁶ , q ⁷ , q ⁸ , q ⁹ , q ¹⁰ , q ¹¹ , q ¹² , q ¹³ ,
q ¹⁴ , q ¹⁵ , q ¹⁶ , q ¹⁷ and q ¹⁸ each independently represent a hydrogen atom, a halogen atom or a methyl group, and X represents an oxygen atom or a sulfur atom. ) Represents. ] The condensed pyrimidinedione derivative represented by the following (hereinafter, referred to as the compound of the present invention) was found.

Next, the substituents of the formula (I) will be specifically described. R ⁴ includes a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a hydrogen atom,
Examples thereof include a fluorine atom and a chlorine atom. Examples of R ⁵ include nitro group, fluorine atom, chlorine atom, bromine atom and iodine atom, preferably chlorine atom and bromine atom.

Examples of R ⁶ include hydrogen atom, mercapto group, amino group, fluorine atom, chlorine atom, bromine atom and iodine atom. When R ⁶ is CO ₂ A ¹ , A ¹ is a hydrogen atom, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-
Butyl group, tert-butyl group, n-pentyl group, ne
Examples thereof include o-pentyl group and n-hexyl group.
When R ⁶ is OA ² , A ² is a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,
n-butyl group, iso-butyl group, sec-butyl group,
tert-butyl group, n-pentyl group, neo-pentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, allyl group, 1-methyl-2-propenyl group, propargyl group and 1- Examples thereof include a methyl-2-propynyl group, and preferably, an n-propyl group, an iso-propyl group, a cyclopentyl group, a propargyl group, and a 1-methyl-2-propynyl group. R ⁶ is OCHA ³ CO ₂ A ⁴ , S
In the case of CHA ³ CO ₂ A ⁴ or NHCHA ³ CO ₂ A ⁴ , A ³ is hydrogen atom, methyl group, ethyl group, n-
Propyl group and iso-propyl group and the like, A
Examples of ⁴ include a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group and an n-butyl group. When R ⁶ is NHCO ₂ A ⁵ , A ⁵ is a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a tert-butyl group, an n-pentyl group, a neo-pentyl group, n-hexyl group, optionally substituted fanyl group (substituents include methyl group, fluorine atom, chlorine atom, etc.) and phenyl group optionally substituted by phenyl group (substituent is methyl Group, fluorine atom, chlorine atom and the like.)
Etc.

As Q

[0012]

[Chemical 7]

[0013]

[Chemical 8]

And the like. The structural feature of the compound of the present invention is that it has a condensed heterocycle in which the 1-position and the 6-position of the pyrimidine ring are cyclized with a carbon chain, and R ⁴ and R ⁵ are used as substituents on the benzene ring substituting the nitrogen atom. And R ^{6 have} a unique combination. Therefore, the compound of the present invention has systemic migration and extremely high herbicidal activity. As a result, the compound of the present invention, compared to conventional herbicides,
It can be applied to various kinds of weeds including perennial weeds by both soil treatment and foliage treatment, and exhibits a high effect rapidly even though spraying with a very low dose, and has a moderate residual effect. It has the great feature of having together.

The compounds of the present invention are shown in, for example, Schemes 1 to 7.
Can be synthesized by the method. [R in Schemes 1 to 7^Four,
R^Five, R⁶, Q, q¹, Q², Q³, Q^Four, Q^Five,
q ⁶, Q⁷, Q⁸, Q⁹, Q^Ten, Q¹¹, Q¹², Q¹³, Q
¹⁴, Q¹⁵, Q¹⁶, Q¹⁷And q¹⁸Has the same meaning as above
Represent, X¹Represents an oxygen atom or a sulfur atom, and G¹Is charcoal
Represents an alkyl group having 1 to 4 elementary atoms, G²Is the number of carbon atoms
1 to 4 represents an alkyl group or a phenyl group, and Hal is
Represents a halogen atom, Y¹Is A²Or CHA³CO₂
A^Four(A², A³And A^FourMeans the same as above
You ), Y²Is CHA³CO₂A^Four(A³and
A^FourRepresents the same meaning as described above. ), Y³Is CHA
³CO₂A^FourOr CO₂A^Five(A³, A^FourAnd A^Five
Represents the same meaning as described above. ) Represents. ]

[0016]

[Chemical 9]

(1) Scheme 1 represents a method for producing a pyrimidine-1,3-dione derivative (I) by reacting an isopropylidene malonate derivative (IIa-c) with phenyliso (thio) cyanate (IIIa). . Normal (IIa ~
(IIIa) 0.5 to 1.5 equivalents, preferably 0.8 to 1.2 equivalents, relative to c) are used. The reaction proceeds even without solvent, but it is usually promoted by using a solvent. As the solvent, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene, xylene, aromatic hydrocarbons such as 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, pyridine, N, N-diethylaniline And the like, acid amides such as dimethylacetamide, N, N-dimethylformamide and N-methylpyrrolidone, sulfur-containing compounds such as dimethylsulfoxide and sulfolane, water and mixtures thereof, and preferably the above. And aliphatic hydrocarbons, aromatic hydrocarbons, acid amides, sulfur-containing compounds, and mixtures thereof.

The reaction proceeds without a base, but usually 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents are used with respect to (IIa to c). Pyridine, triethylamine, N, N-dimethylaniline, N, N-as a base
Nitrogen-containing organic bases such as diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane, sodium hydroxide, potassium hydride, sodium hydroxide, potassium hydroxide Inorganic bases such as sodium carbonate and potassium carbonate, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tert-butoxide are preferred, and sodium hydride, sodium hydroxide and potassium hydroxide are preferred.

The reaction temperature is usually -70 to 200 ° C, preferably -50 ° C to the reflux temperature of the reaction mixture.
The reaction time is usually 5 minutes to 72 hours, preferably 10 minutes to 12 hours.

[0020]

[Chemical 10]

(2) In Scheme 2, isopropylidene malonate derivatives (IIa-c) are reacted with N-phenyl (thio) carbamate (IIIb) to produce pyrimidine-1,3-.
It represents a method for producing a dione derivative (I). Normal (IIa
To (c), (IIIb) 0.5 to 1.5 equivalents, preferably 0.8 to 1.2 equivalents are used. The reaction usually requires a solvent, and as the solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, halogenated carbonization such as chloroform and methylene chloride. Hydrogen, 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 and N, N-diethylaniline, dimethyl Acid amides such as acetamide, N, N-dimethylformamide and N-methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, alcohols such as methanol, ethanol, propanol and butanol, water and mixtures thereof. Preferably aliphatic hydrocarbons mentioned above, aromatic hydrocarbons, acid amides, the sulfur-containing compounds and mixtures thereof.

Usually 0.5 to 1 bases (IIa to c)
0 equivalent, preferably 1.0 to 3.0 equivalent is used. 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 as a base Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tert-butoxide,
Metal alkyl mercaptides such as sodium methyl mercaptide, sodium ethyl mercaptide and the like,
Preferred are inorganic bases such as sodium hydride and metal alcoholates 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 24 hours.

[0024]

[Chemical 11]

(3) Scheme 3 is an acrylic acid derivative (IV
a) to c) phenyliso (thio) cyanate (IIIa)
Represents a method for producing the pyrimidine-1,3-dione derivative (I), and can be carried out under the same reaction conditions as in Scheme 1.

[0026]

[Chemical 12]

(4) Scheme 4 is an acrylic acid derivative (IV
N-phenyl (thio) carbamate (III
b) is reacted to produce a pyrimidine-1,3-dione derivative (I), which can be carried out under the same reaction conditions as in Scheme 2.

[0028]

[Chemical 13]

(5) Scheme 5 is a phenol derivative (V
a) is reacted with Hal-Y ¹ (VIa) to give pyrimidine-
1 shows a method for producing a 1,3-dione derivative (I). Usually, (VIa) is used in an amount of 0.5 to 10 equivalents, preferably 0.8 to 2.0 equivalents, relative to (Va). The reaction proceeds even without solvent, but it is usually promoted by using a solvent. Hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether as a solvent, benzene, toluene,
Aromatic hydrocarbons such as 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, acetonitrile and isobutyronitrile, etc. Tertiary amines such as nitriles, pyridine, N, N-diethylaniline, acid amides such as dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, sulfur-containing compounds such as dimethylsulfoxide and sulfolane, and These include mixtures.

The reaction proceeds even without a base, but usually 0.5 to 10 equivalents relative to (Va) are used. Moreover, you may use it as a solvent in large excess. Pyridine as a base,
Triethylamine, N, N-dimethylaniline, N, N
-Diethylaniline, 4- (N, N-dimethylamino)
Nitrogen-containing organic bases such as pyridine and 1,4-diazabicyclo [2.2.2] octane, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxy And metal alkoxides such as sodium ethoxide, potassium tert-butoxide and the like, and preferably the above-mentioned nitrogen-containing organic bases and inorganic bases.

The reaction temperature is usually -30 to 160 ° C, preferably -10 to 130 ° C. Reaction time is usually 1
It takes 0 minutes to 48 hours, preferably 30 minutes to 24 hours.

[0032]

[Chemical 14]

(6) Scheme 6 represents a method for producing a pyrimidine-1,3-dione derivative (I) by reacting a thiophenol derivative (Vb) with Hal-Y ² (VIb), and is similar to Scheme 5. It can be carried out under reaction conditions.

[0034]

[Chemical 15]

(7) Scheme 7 shows the aniline derivative (V
c) is reacted with Hal-Y ³ (VIc) to give pyrimidine-
It represents a method for producing the 1,3-dione derivative (I), and can be performed under the same reaction conditions as in Scheme 5.

[0036]

EXAMPLES The synthetic examples of the compounds of the present invention are specifically described below as Examples, but the present invention is not limited thereto. [Example 1] 2- (4-chloro-5-ethoxycarbonyl-2-fluorophenyl) -5,6,7-trihydro-2H, 8H-pyrrolo [1,2-C] pyrimidine-
Synthesis of 1,3-dione (Compound No. 1)

[0037]

[Chemical 16]

4-chloro-5-ethoxycarbonyl-2
3.00 g (13.8 mmol) of fluoroaniline were dissolved in 28 ml of ethyl acetate and 1.65 ml (13.8 mmol) of trichloromethyl chloroformate were added at 0 ° C. Thirty
After minutes, the reaction solution was heated to reflux temperature and reacted for 2 hours.
After the reaction, ethyl acetate was distilled off to synthesize an isocyanate derivative. Sodium hydride (55%)
1. To a mixed solution of 0.60 g (13.8 mmol) and N, N-dimethylformamide (29 ml) at 10 ° C. or lower, isopropylidene (pyrrolidin-2-ylidene) -malonate.2.
91 g (13.8 mmol) was added, and after 30 minutes, the mixture was cooled to -30 ° C., and the isocyanate derivative synthesized above was treated with N, N-.
It was dissolved in 21 ml of dimethylformamide and added dropwise. Thirty
After minutes, the temperature was returned to room temperature, and the reaction was further performed at 110 ° C. for 4 hours.
After distilling off N, N-dimethylformamide, it was dissolved in ethyl acetate and washed with water (3 times) and saturated brine. It was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off to obtain a group product. By purifying this by column chromatography (developing solvent: chloroform), 0.74 g of the desired product was obtained.
Was obtained as a colorless oil.

¹ H-NMR (CDCl ₃ ) δ (pp
m): 1.36 (3H, t, j = 7Hz), 2.16
(2H, tt, j = 7, 7Hz), 3.00 (2H,
t, j = 7 Hz), 4.01 (2H, t, j = 7H)
z), 4.38 (2H, q, j = 7 Hz), 5.75
(1H, s), 7.39 (1H, d, j = 8Hz),
7.92 (1 H, d, j = 7 Hz) [Example 2] 2- (4-chlorophenyl) -5, 6, 7
-Synthesis of trihydro-2H, 8H-pyrrolo [1,2-C] pyrimidine-1,3-dione (Compound No. 2)

[0040]

[Chemical 17]

0.62 g of sodium hydride (55%)
(14.2 mmol), N, N-dimethylformamide (2
5 ml) at a temperature of 10 ° C or lower, isopropylidene (pyrrolidine-2-ylidene) -malonate 3.00 g (1
(4.2 mmol) was added and after 30 minutes, cooled to -30 ° C.,
2.18 g of -chloro-phenyl isocyanate (14.
2 mmol) was dissolved in 21 ml of N, N-dimethylformamide and added dropwise. After 30 minutes, the mixture was returned to room temperature and further reacted at 110 ° C for 4 hours. After distilling off N, N-dimethylformamide, it was dissolved in ethyl acetate and washed with water (3 times) and saturated brine. It was dried over anhydrous sodium sulfate and ethyl acetate was distilled off to obtain a crude product. This was purified by column chromatography (developing solvent: chloroform) to obtain 0.74 g of the desired product as pale yellow crystals.

Melting point 182 to 184 ° C. ¹ H-NMR (CDCl ₃ ) δ (ppm): 2.14
(2H, tt, j = 7,7Hz), 2.96 (2H,
t, j = 7 Hz), 3.97 (2H, t, j = 7H)
z), 5.73 (1H, s), 7.05 (2H, d, j
= 8 Hz), 7.48 (2H, d, j = 8 Hz) [Example 3] 2- (4-chloro-2-fluorophenyl) -5,6,7-trihydro-2H, 8H-pyrrolo [1 , 2-C] Pyrimidine-1,3-dione (Compound N
o.3) synthesis

[0043]

[Chemical 18]

0.26 g of sodium hydride (55%)
(6.00 mmol), N, N-dimethylformamide (1
0ml) to a mixture of ethyl (pyrrolidine-2
-Ylidene) -acetate 0.93 g (6.00 mmol)
After 30 minutes from the addition of 1.3 g (6.00 mmol) of ethyl 4-chloro-2-fluorophenylcarbamate, the mixture was heated at 110 ° C. for 6 hours. After distilling off N, N-dimethylformamide, ice water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated saline and dried over anhydrous sodium sulfate. Ethyl acetate was distilled off to obtain a crude product. This was purified by preparative thin layer chromatography (developing solvent: hexane-ethyl acetate 2: 1) to obtain 0.17 g of the desired product as a colorless viscous oil.

¹ H-NMR (CDCl ₃ ) δ (pp
m): 2.10 (2H, tt, j = 7,7Hz), 2.
91 (2H, t, j = 7 Hz), 3.89 (2H, t,
j = 7 Hz), 5.60 (1 H, s), 6.92 to 7.
26 (3H, m) [Example 4]

[0046]

[Chemical 19]

In the same manner, the desired product was obtained as a colorless viscous oil. ¹ H-NMR (CDCl ₃ ) δ (ppm): 2.24
(2H, tt, j = 7.7Hz), 3.01 (2H,
t, j = 7 Hz), 3.78 (3H, s), 4.01
(2H, t, j = 7 Hz), 5.74 (1H, s),
7.21 (1H, brs), 7.29 (1H, d, j =
9 Hz), 8.20 (1 H, d, j = 7 Hz) The compounds of the present invention synthesized according to the scheme or the examples are shown in Table 1 including the compounds synthesized in the examples. Is not limited by. However, in Table 1, Me is a methyl group, Et is an ethyl group, Pr is a propyl group, Bu is a butyl group, and Pen is a
Represents a pentyl group, Hex represents a hexyl group, Ph represents a phenyl group, n- represents normal, i- represents iso, s- represents secondary, t- represents tertiary, and c- represents cyclo. Further, among the compounds included in the present invention, the compound having an asymmetric carbon includes an optically active compound (+) form and (−) form. Table 1

[0048]

[Chemical 20]

[0049]

[Chemical 21]

[0050]

[Chemical formula 22]

─────────────────────────── R ⁴ R ⁵ R ⁶ ────────────── ───────────── H Cl HH Cl FH Cl Cl H Cl Br H Cl IH Cl CO ₂ HH Cl CO ₂ Me H Cl CO ₂ Et H Cl CO ₂ n-Pr H Cl CO ₂ i-Pr H Cl CO ₂ n-Bu H Cl CO ₂ i-Bu H Cl CO ₂ s-Bu H Cl CO ₂ t-Bu H Cl CO ₂ n-Pen H Cl CO ₂ n-Hex H Cl OH H Cl OMe H Cl OEt H Cl On-Pr H Cl Oi-Pr H Cl On-Bu H Cl Oi-Bu H Cl Os-Bu H Cl Ot-Bu ──────────────── ───────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── H Cl On-Pen H Cl On-Hex H Cl Oc-Pr H Cl Oc-Pen H Cl Oc-Hex H Cl OCH ₂ CH = CH ₂ H Cl OCH ₂ C ≡ CH H Cl OCHMeC ≡ CH H Cl OCH ₂ CO ₂ Me H Cl OCH ₂ CO ₂ Et H Cl OCHMeCO ₂ Me H Cl OCHMeCO ₂ Et H Cl SCH ₂ CO ₂ Me H Cl SCH ₂ CO ₂ Et H Cl SCHMeCO ₂ Me H Cl SCHMeCO ₂ Et H Cl SH H Cl NH ₂ H Cl NHCH ₂ CO ₂ Me H Cl NHCH ₂ CO ₂ Et H Cl NHCHMeCO ₂ Me H Cl NHCHMeCO ₂ Et H Cl NHCO ₂ Me ── ─────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── H Cl NHCO ₂ Et H Cl NHCO ₂ n-Pr H Cl NHCO ₂ i-Pr H Cl NHCO ₂ n-Bu H Cl NHCO ₂ i -Bu H Cl NHCO ₂ s-Bu H Cl NHCO ₂ t-Bu H Cl NHCO ₂ n-Pen H Cl NHCO ₂ n-Hex H Cl NHCO ₂ Ph H Cl NHCO _2- (4-Cl-Ph) H Cl NHCO _2- (4-Me-Ph) H Cl NHCO ₂ CH ₂ Ph H Cl NHCO ₂ CH _2- (4-Me-Ph) H Cl NHCO ₂ CH _2- (4-Cl-Ph) H Cl NHCO ₂ CH ₂ -(4-Et-Ph) Cl Cl H Cl Cl F Cl Cl Cl Cl Cl Br Cl Cl I Cl Cl CO ₂ H Cl Cl CO ₂ Me ────────────────── ──────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Cl CO ₂ Et Cl Cl ₂ n-Pr Cl Cl CO ₂ i-Pr Cl Cl CO ₂ n-Bu Cl Cl CO ₂ i -Bu Cl Cl CO ₂ s-Bu Cl Cl CO ₂ t-Bu Cl Cl CO ₂ n-Pen Cl Cl CO ₂ n-Hex Cl Cl OH Cl Cl OMe Cl Cl OEt Cl Cl On-Pr Cl Cl Oi-Pr Cl Cl On-Bu Cl Cl Oi-Bu Cl Cl Os-Bu Cl Cl Ot-Bu Cl Cl On-Pen Cl Cl On-Hex Cl Cl Oc-Pr Cl Cl Oc-Pen Cl Cl Oc-Hex ─────── ─────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Cl OCH ₂ CH = CH ₂ Cl Cl OCH ₂ C ≡ CH Cl Cl OCHMeC ≡ CH Cl Cl OCH ₂ CO ₂ Me Cl Cl OCH ₂ CO ₂ Et Cl Cl OCHMeCO ₂ Me Cl Cl OCHMeCO ₂ Et Cl Cl SCH ₂ CO ₂ Me Cl Cl SCH ₂ CO ₂ Et Cl Cl SCHMeCO ₂ Me Cl Cl SCHMeCO ₂ Et Cl Cl SH Cl Cl NH ₂ Cl Cl NHCH ₂ CO ₂ Me Cl Cl NHCH ₂ CO ₂ Et Cl Cl NHCHMeCO ₂ Me Cl Cl NHCHMeCO ₂ Et Cl Cl NHCO ₂ Me Cl Cl NHCO ₂ Et Cl Cl NHCO ₂ n-Pr Cl Cl NHCO ₂ i-Pr Cl Cl NHCO ₂ n-Bu Cl Cl NHCO ₂ i-Bu ────────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Cl NHCO ₂ s-Bu Cl Cl NHCO ₂ t-Bu Cl Cl NHCO ₂ n-Pen Cl Cl NHCO ₂ n-Hex Cl Cl NHCO ₂ Ph Cl Cl NHCO _2- (4-Cl-Ph) Cl Cl NHCO _2- (4-Me-Ph) Cl Cl NHCO ₂ CH ₂ Ph Cl Cl NHCO ₂ CH _2- (4-Me-Ph) Cl Cl NHCO ₂ CH _2- (4-Cl-Ph) Cl Cl NHCO ₂ CH _2- (4-Et-Ph) F Cl HF Cl FF Cl Cl F Cl Br F Cl IF Cl CO ₂ HF Cl CO ₂ Me F Cl CO ₂ Et F Cl CO ₂ n-Pr F Cl CO ₂ i-Pr F Cl CO ₂ n-Bu F Cl CO ₂ i-Bu ────────────────────── ──────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F Cl CO ₂ s-Bu F Cl CO ₂ t-Bu F Cl CO ₂ n-Pen F Cl CO ₂ n-Hex F Cl OH F Cl OMe F Cl OEt F Cl On-Pr F Cl Oi-Pr F Cl On-Bu F Cl Oi-Bu F Cl Os-Bu F Cl Ot-Bu F Cl On-Pen F Cl On-Hex F Cl Oc- Pr F Cl Oc-Pen F Cl Oc-Hex F Cl OCH ₂ CH = CH ₂ F Cl OCH ₂ C ≡CH F Cl OCHMeC ≡CH F Cl OCH ₂ CO ₂ Me F Cl OCH ₂ CO ₂ Et ────── ──────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F Cl OCHMeCO ₂ Me F Cl OCHMeCO ₂ Et F Cl SCH ₂ CO ₂ Me F Cl SCH ₂ CO ₂ Et F Cl SCHMeCO ₂ Me F Cl SCHMeCO ₂ Et F Cl SH F Cl NH ₂ F Cl NHCH ₂ CO ₂ Me F Cl NHCH ₂ CO ₂ Et F Cl NHCHMeCO ₂ Me F Cl NHCHMeCO ₂ Et F Cl NHCO ₂ Me F Cl NHCO ₂ Et F Cl NHCO ₂ n- Pr F Cl NHCO ₂ i-Pr F Cl NHCO ₂ n-Bu F Cl NHCO ₂ i-Bu F Cl NHCO ₂ s-Bu F Cl NHCO ₂ t-Bu F Cl NHCO ₂ n-Pen F Cl NHCO ₂ n-Hex F Cl NHCO ₂ Ph ────────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F Cl NHCO _2- (4-Cl-Ph) F Cl NHCO _2- (4-Me-Ph) F Cl NHCO ₂ CH ₂ Ph F Cl NHCO ₂ CH _2- (4-Me-Ph) F Cl NHCO ₂ CH _2- (4-Cl-Ph) F Cl NHCO ₂ CH _2- (4-Et-Ph) H Br HH Br FH Br Cl H Br Br H Br IH Br CO ₂ HH Br CO ₂ Me H Br CO ₂ Et H Br CO ₂ n-Pr H Br CO ₂ i-Pr H Br CO ₂ n-Bu H Br CO ₂ i-Bu H Br CO ₂ s-Bu H Br CO ₂ t-Bu H Br CO ₂ n-Pen H Br CO ₂ n-Hex H Br OH ──────────────────────── ────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── H Br OMe H Br OEt H Br On-Pr H Br Oi-Pr H Br On-Bu H Br Oi-Bu H Br Os-Bu H Br Ot-Bu H Br On-Pen H Br On-Hex H Br Oc-Pr H Br Oc-Pen H Br Oc-Hex H Br OCH ₂ CH = CH ₂ H Br OCH ₂ C ≡CH H Br OCHMeC≡CH H Br OCH ₂ CO ₂ Me H Br OCH ₂ CO ₂ Et H Br OCHMeCO ₂ Me H Br OCHMeCO ₂ Et H Br SCH ₂ CO ₂ Me H Br SCH ₂ CO ₂ Et H Br SCHMeCO ₂ Me ──────── ────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── H Br SCHMeCO ₂ Et H Br SH H Br NH ₂ H Br NHCH ₂ CO ₂ Me H Br NHCH ₂ CO ₂ Et H Br NHCHMeCO ₂ Me H Br NHCHMeCO ₂ Et H Br NHCO ₂ Me H Br NHCO ₂ Et H Br NHCO ₂ n-Pr H Br NHCO ₂ i-Pr H Br NHCO ₂ n-Bu H Br NHCO ₂ i-Bu H Br NHCO ₂ s-Bu H Br NHCO ₂ t-Bu H Br NHCO ₂ n-Pen H Br NHCO ₂ n-Hex H Br NHCO ₂ Ph H Br NHCO _2- (4-Cl-Ph) H Br NHCO _2- (4-Me-Ph) H Br NHCO ₂ CH ₂ Ph H Br NHCO ₂ CH _2- (4-Me-Ph) H Br NHCO ₂ CH _2- (4-Cl-Ph) ──────────────── ─────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── H Br NHCO ₂ CH _2- (4-Et-Ph) F Br HF Br FF Br Cl F Br Br F Br IF Br CO ₂ HF Br CO ₂ Me F Br CO ₂ Et F Br CO ₂ n-Pr F Br CO ₂ i-Pr F Br CO ₂ n-Bu F Br CO ₂ i-Bu F Br CO ₂ s-Bu F Br CO ₂ t- Bu F Br CO ₂ n-Pen F Br CO ₂ n-Hex F Br OH F Br OMe F Br OEt F Br On-Pr F Br Oi-Pr F Br On-Bu ─────────── ────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F Br Oi-Bu F Br Os-Bu F Br Ot-Bu F Br On-Pen F Br On-Hex F Br Oc-Pr F Br Oc-Pen F Br Oc-Hex F Br OCH ₂ CH = CH ₂ F Br OCH ₂ C ≡CH F Br OCHMeC ≡CH F Br OCH ₂ CO ₂ Me F Br OCH ₂ CO ₂ Et F Br OCHMeCO ₂ Me F Br OCHMeCO ₂ Et F Br SCH ₂ CO ₂ Me F Br SCH ₂ CO ₂ Et F Br SCHMeCO ₂ Me F Br SCHMeCO ₂ Et F Br SH F Br NH ₂ F Br NHCH ₂ CO ₂ Me F Br NHCH ₂ CO ₂ Et ── ─────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F Br NHCHMeCO ₂ Me F Br NHCHMeCO ₂ Et F Br NHCO ₂ Me F Br NHCO ₂ Et F Br NHCO ₂ n-Pr F Br NHCO ₂ i-Pr F Br NHCO ₂ n-Bu F Br NHCO ₂ i-Bu F Br NHCO ₂ s-Bu F Br NHCO ₂ t-Bu F Br NHCO ₂ n-Pen F Br NHCO ₂ n-Hex F Br NHCO ₂ Ph F Br NHCO _2- (4-Cl-Ph) F Br NHCO _2- (4-Me-Ph) F Br NHCO ₂ CH ₂ Ph F Br NHCO ₂ CH _2- (4-Me-Ph) F Br NHCO ₂ CH _2- (4-Cl-Ph) F Br NHCO ₂ CH _2- (4-Et-Ph) Cl Br H Cl Br F Cl Br Cl Cl Br Br ──────────────── ─────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Br I Cl Br CO ₂ H Cl Br CO ₂ Me Cl Br CO ₂ Et Cl Br CO ₂ n-Pr Cl Br CO ₂ i- Pr Cl Br CO ₂ n-Bu Cl Br CO ₂ i-Bu Cl Br CO ₂ s-Bu Cl Br CO ₂ t-Bu Cl Br CO ₂ n-Pen Cl Br CO ₂ n-Hex Cl Br OH Cl Br OMe Cl Br OEt Cl Br On-Pr Cl Br Oi-Pr Cl Br On-Bu Cl Br Oi-Bu Cl Br Os-Bu Cl Br Ot-Bu Cl Br On-Pen Cl Br On-Hex ──────── ────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Br Oc-Pr Cl Br Oc-Pen Cl Br Oc-Hex Cl Br OCH ₂ CH = CH ₂ Cl Br OCH ₂ C ≡CH Cl Br OCHMeC≡CH Cl Br OCH ₂ CO ₂ Me Cl Br OCH ₂ CO ₂ Et Cl Br OCHMeCO ₂ Me Cl Br OCHMeCO ₂ Et Cl Br SCH ₂ CO ₂ Me Cl Br SCH ₂ CO ₂ Et Cl Br SCHMeCO ₂ Me Cl Br SCHMeCO ₂ Et Cl Br SH Cl Br NH ₂ Cl Br NHCH ₂ CO ₂ Me Cl Br NHCH ₂ CO ₂ Et Cl Br NHCHMeCO ₂ Me Cl Br NHCHMeCO ₂ Et Cl Br NHCO ₂ Me Cl Br NHCO ₂ Et Cl Br NHCO ₂ n-Pr ────────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── Cl Br NHCO ₂ i-Pr Cl Br NHCO ₂ n-Bu Cl Br NHCO ₂ i-Bu Cl Br NHCO ₂ s-Bu Cl Br NHCO ₂ t-Bu Cl Br NHCO ₂ n-Pen Cl Br NHCO ₂ n-Hex Cl Br NHCO ₂ Ph Cl Br NHCO _2- (4-Cl-Ph) Cl Br NHCO _2- (4-Me-Ph) Cl Br NHCO ₂ CH ₂ Ph Cl Br NHCO ₂ CH _2- (4-Me-Ph) Cl Br NHCO ₂ CH _2- (4-Cl-Ph) Cl Br NHCO ₂ CH _2- (4-Et-Ph) F NO ₂ HF NO ₂ FF NO ₂ Cl F NO ₂ Br F NO ₂ IF NO ₂ CO ₂ HF NO ₂ CO ₂ Me F NO ₂ CO ₂ Et F NO ₂ CO ₂ n-Pr ───────────── ───────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F NO ₂ CO ₂ i-Pr F NO ₂ CO ₂ n-Bu F NO ₂ CO ₂ i-Bu F NO ₂ CO ₂ s- Bu F NO ₂ CO ₂ t-Bu F NO ₂ CO ₂ n-Pen F NO ₂ CO ₂ n-Hex F NO ₂ OH F NO ₂ OMe F NO ₂ OEt F NO ₂ On-Pr F NO ₂ Oi-Pr F NO ₂ On-Bu F NO ₂ Oi-Bu F NO ₂ Os-Bu F NO ₂ Ot-Bu F NO ₂ On-Pen F NO ₂ On-Hex F NO ₂ Oc-Pr F NO ₂ Oc-Pen F NO ₂ Oc-Hex F NO ₂ OCH ₂ CH = CH ₂ F NO ₂ OCH ₂ C ≡CH ────────────────────────────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F NO ₂ OCHMeC≡CH F NO ₂ OCH ₂ CO ₂ Me F NO ₂ OCH ₂ CO ₂ Et F NO ₂ OCHMeCO ₂ Me F NO ₂ OCHMeCO ₂ Et F NO ₂ SCH ₂ CO ₂ Me F NO ₂ SCH ₂ CO ₂ Et F NO ₂ SCHMeCO ₂ Me F NO ₂ SCHMeCO ₂ Et F NO ₂ SH F NO ₂ NH ₂ F NO ₂ NHCH ₂ CO ₂ Me F NO ₂ NHCH ₂ CO ₂ Et F NO ₂ NHCHMeCO ₂ Me F NO ₂ NHCHMeCO ₂ Et F NO ₂ NHCO ₂ Me F NO ₂ NHCO ₂ Et F NO ₂ NHCO ₂ n-Pr F NO ₂ NHCO ₂ i-Pr F NO ₂ NHCO ₂ n-Bu F NO ₂ NHCO ₂ i-Bu F NO ₂ NHCO ₂ s-Bu F NO ₂ NHCO ₂ t-Bu ─────────────────────── ─────

Table 1 (continued) ─────────────────────────── R ⁴ R ⁵ R ⁶ ───────── ─────────────────── F NO ₂ NHCO ₂ n-Pen F NO ₂ NHCO ₂ n-Hex F NO ₂ NHCO ₂ Ph F NO ₂ NHCO _2- (4- Cl-Ph) F NO ₂ NHCO _2- (4-Me-Ph) F NO ₂ NHCO ₂ CH ₂ Ph F NO ₂ NHCO ₂ CH _2- (4-Me-Ph) F NO ₂ NHCO ₂ CH _2- (4 -Cl-Ph) F NO ₂ NHCO ₂ CH _2- (4-Et-Ph) ────────────────────────────

The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but generally 0.0001 to 10 per hectare (ha) as an active ingredient amount.
About kg, preferably about 0.001 to 5 kg is suitable. If necessary, the compound of the present invention may be mixed with other herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of formulation or spraying.

In particular, by applying it in combination with another herbicide, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicidal spectrum can be expanded by the synergistic action of the mixed drugs, and a higher herbicidal effect can be expected. At this time, it is possible to combine a plurality of known herbicides at the same time. The types of herbicides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook 1990.
There are compounds listed in the annual edition.

In particular, when the compound of the present invention is applied to soybean, preferred agents to be mixed with the compound of the present invention include trifluralin, pendimethalin, alachlor, metolachor. , Metribuzin, linuron, chlorimur-ethyl
on ethyl), imazaquin, imazethapyr (i
mazethapyr), dinoceb (dinoseb), bifenox (b
ifenox), clomazone, etc.

In applying the compound of the present invention as a herbicide, generally, a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth and white carbon, or water, alcohols (isopropanol, butanol, benzyl alcohol, fluroalcohol) is used. Furyl 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 other liquid carriers can be mixed and applied, and if desired, surfactants, emulsifiers, dispersants, penetrants, spreading agents, thickeners, antifreeze. Agents, anti-caking agents, stabilizers, etc., liquids, emulsions, wettable powders,
It can be put into practical use in any dosage form such as a dry flowable agent, a flowable agent, a powder agent, and a granule agent.

Next, formulation examples of preparations using the compound of the present invention will be shown concretely. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight. [Wettable powder] Compound of the present invention ─────── 5-80 parts Solid carrier ─────── 10-85 parts Surfactant ─────── 1-10 parts Others ─── ──── Examples of 1 to 5 parts and others include anti-caking agents.

[Emulsion] Compound of the present invention ─────── 1 to 30 parts Liquid carrier ─────── 30 to 95 parts Surfactant ─────── 5 to 15 parts [Flowable] Agent] Compound of the present invention ─────── 5-70 parts Liquid carrier ─────── 15-65 parts Surfactant ─────── 5-12 parts Others ────── -Other than 5 to 30 parts, for example, antifreezing agents, thickeners and the like can be mentioned.

[Granular wettable powder (dry flowable agent)] Compound of the present invention ─────── 20-90 parts Solid carrier ─────── 10-60 parts Surfactant ─────── 1-20 parts [Granule] Compound of the present invention ─────── 0.1-10 parts Solid carrier ─────── 90〜99.99 parts Other ─────── 1-5 parts [Formulation Example 1] Wettable powder Compound of the present invention No. 1 ───────── 50 parts Sieglite PFP ───────── 43 copies (Kaolin clay: product name of Siglite Industrial Co., Ltd.) Solpol 5050 ───────── Part 2 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000 C ──────── Part 3 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80 (anti-caking agent)-2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion compound of the present invention No. 1 ──────── 3 parts xylene ──────── 76 parts Isophorone ──────── 15 parts Sorpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Invention Compound No. 1 ──────── 35 parts Agrisol S-711 ──────── 8 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000 C ──────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water ──────── 20 copies (Thickener: Loan Poulin's trade name) Ethylene glycol (antifreeze) ── 8 parts Water ──────── 28.5 copies The above is uniformly mixed to obtain a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention No. 1 ───────── 75 parts Isoban No. 1 ───────── 10 parts (anionic Surfactant: Kuraray Isoprene Chemical Co., Ltd. product name Vanillex N ───────── 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd. product name) Carplex # 80 ───── ─── 10 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granules Compound of the present invention No. 1 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ─────── 44.9 parts After crushing, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

[Formulation Example 6] Wettable powder Inventive compound No. 2 ──────── 50 parts Sieglite PFP ───────── 43 copies (Kaolin clay: product name of Siglite Industrial Co., Ltd.) Solpol 5050 ───────── Part 2 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000 C ──────── Part 3 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80 (anti-caking agent)-2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 7] Milk compound No. 2 of the present invention ──────── 3 parts xylene ──────── 76 parts Isophorone ───────── 15 parts Solpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 8] Flowable agent Inventive Compound No. 2 ──────── 35 parts Agrisol S-711 ──────── 8 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000 C ──────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water ──────── 20 copies (Thickener: Loan Poulin's trade name) Ethylene glycol (antifreeze) ── 8 parts Water ──────── 28.5 copies The above is uniformly mixed to obtain a flowable agent.

[Formulation Example 9] Granular wettable powder (dry flowable agent) Compound of the present invention No. 2 ──────────────────────────────── 10 parts (anionic Surfactant: Kuraray Isoprene Chemical Co., Ltd. product name Vanillex N ───────── 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd. product name) Carplex # 80 ───── ─── 10 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 10] Granules Compound of the present invention No. 2 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ─────── 44.9 parts The above are uniformly mixed. After crushing, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

[Formulation Example 11] Wettable powder Inventive compound No. 3 ──────── 50 parts Sieglite PFP ───────── 43 copies (Kaolin clay: product name of Siglite Industrial Co., Ltd.) Solpol 5050 ───────── Part 2 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000 C ──────── Part 3 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80 (anti-caking agent)-2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 12] Emulsion Compound of the present invention No. 3 ──────── 3 parts xylene ──────── 76 parts Isophorone ───────── 15 parts Solpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 13] Flowable agent Inventive compound No. 3 ──────── 35 parts Agrisol S-711 ──────── 8 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000 C ──────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water ──────── 20 copies (Thickener: Loan Poulin's trade name) Ethylene glycol (antifreeze) ── 8 parts Water ──────── 28.5 copies The above is uniformly mixed to obtain a flowable agent.

[Formulation Example 14] Granular wettable powder (dry flowable agent) Compound of the present invention No. 3 ────────────────────────────── 10 parts Surfactant: Kuraray Isoprene Chemical Co., Ltd. product name Vanillex N ───────── 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd. product name) Carplex # 80 ───── ─── 10 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 15] Granules Compound of the present invention No. 3 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ─────── 44.9 parts After crushing, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

In use, the wettable powder, emulsion, flowable powder, and granular wettable powder are diluted 50 to 1000 times with water and sprayed so that the active ingredient is 0.0001 to 10 kg per hectare (ha). . The compound of the present invention can be used as a herbicide for upland fields in any treatment method such as soil treatment, soil admixture treatment, and foliage treatment. Examples of the field weeds (Cropland weeds) targeted by the compound of the present invention include, for example, Solanum nigrum and Datura ( Da ).
Solanacea represented by tura stramonium )
e) Malvaceae weeds represented by weeds, Abutilon theophrasti , American spine deer ( Side spinosa ), and Malaga morning glory ( Ipomoeapurpure)
a ) such as morning glory ( Ipomoea spps.) and bindweed ( C
Convolvaceae ( Convolvaceae) represented by alystegia spps.)
ulaceae) Weeds, Amaranthus lividus , Amaranthus retroflexus, and other Amaranthaceae weeds, Xanthium pensy
lvanicum ), ragweed ( Ambrosia artemisiaefolia ),
Sunflower (Helianthus annuu), galinsoga quadriradiata (Galins
oga ciliat) , Horse Chestnut ( Cirsium arvens)
e) , Nobogulhus ( Senecio vulgaris ), Himejeon ( Er
igeron annus ) and other weeds (Compositae) weeds, red peppers ( Rorippa indica ), and white-bellied peaches ( Si
napis arvensis ), Nazuna ( Capsella Bursapastris )
Cruciferae weeds represented by, etc., Polygonum Blumei, Polygonum convol
vulus ) and other weeds (Polygonaceae) weeds,
Portulacaceae weeds, such as Portulaca oleracea, are known as Chenopodium
album ), koa kaza ( Chenopodium ficifolium ), broom ( Kochia scoparia ), etc.
Enopodiaceae) Weeds, Caryophyllaceae weeds represented by Stellaria media, etc., Scrophulariaceae weeds represented by Veronica persica , Commerceae
Elina communis ) and other commissinaceae (Commelin
aceae) weeds, moss ( Lamium amplexicaule ),
Labiatae weeds represented by Lamium purpureum, etc., and Euphorbia su
pina ), Euphorbia maculata, and other Euphorbiaceae weeds, such as Euphorbia maculata, Galium spurium , and Galium
aparine ), Akane ( Rubia akane ), etc., and Rubiaceae weeds, violets ( Viola arvensis )
Weeds (Violaceae) represented by the same species, Sesbania exaltata , Ebisugusa ( Ca
Legumes (Leguminosa) represented by ssia obtusifolia )
e) Broad-leaved weeds such as weeds, wild sorghum ( Sorgham bicolor) , and giant millet ( Panicum di )
chotomiflorum ), Johnson grass ( Sorghum halepe
nse ), barnyard grass ( Echinochloa crus-galli ), crabgrass ( Digitaria adscendens ), oats ( Avena fatu )
a ), Steller's grass ( Eleusine indica ), Green foxtail ( Setaria viridis ), Sparrow ( Alopecurus )
aegualis ) and other grass weeds (Graminaceous)
weeds), Chinese nutsedge ( Cyperus rotundus , Cyperus escu
lentus ) and other Cyperaceae weeds (Cyperace)
ous weeds) etc.

Further, the compound of the present invention can be used as a herbicide for paddy field in any treatment method such as soil treatment under flooded water and foliage treatment. Examples of paddy weeds include paddy weeds ( Alisma canaliculatu).
m ), Modassus ( Sagittaria trifolia ), Urikawa ( S
agittaria pygmaea ), etc.
ataceae) weeds, Cyperus difformis ,
Cyperus serotinus , Firefly ( Scirp )
us juncoides ), Elegocharis kuroguwa
i ) Cyperaceae weeds typified by E. , etc., Scrothulariaceae weeds represented by Lindemia pyxidaria , Monochor
ia vaginalis ) and other species of water mallow (Potender
iaceae) weeds, hilus white ( Potamogeton distinctus )
Such as, for example, weeds (Potamogetonaceae), weeds (Lythraceae), represented by Rotala indica , Echinochloa ( Echinochloa )
crus-galli ) and other grass weeds (Gramineae).

Further, the compound of the present invention can be applied to the control of various weeds in non-agricultural fields such as athletic fields, open fields, and track ends as well as agricultural and horticultural fields such as upland fields, paddy fields and orchards. Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples. [Test Example 1] Herbicidal effect test by soil treatment Put sterilized diluvial soil in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm, and put Nobye, Mejiba, Cyperus japonicus, Pinegrass, Prickly pear, Pepper, rice,
Mixed sowing of corn, wheat, soybean and cotton, about 1 cm
After covering with soil, small amounts of spray were uniformly sprayed onto the soil surface so that the amount of active ingredient was a predetermined ratio. As a drug solution for spraying, a formulation appropriately adjusted according to the above-mentioned formulation example or the like was diluted with water and used. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds and crops was investigated according to the following criteria. The results are shown in Table 2.

Judgment Criteria 5-Hericidal rate 90% or more (almost complete death) 4-Hericidal rate 70-90% 3-Hericidal rate 40-70% 2-Hericidal rate 20-40% 1-Hericidal rate 5-20% 0 -Herbicidal rate 5% or less (almost no effect) However, the above-mentioned herbicidal rate is determined by the following formula by judging the above-ground vegetation weight of the chemical treatment area and the above-ground vegetation weight of the untreated area. is there. Herbicide rate = [1-above-ground fresh grass weight of treated area / above-ground fresh grass weight of untreated area] x 100 [Test Example 2] Herbicidal effect test by foliage treatment 15 cm long, 22 cm wide, 6 cm deep made of plastic Put the sterilized diluvial soil in the box, and then, Nobye, Crabgrass, Cyperaceae, dogwood, syringa, dog pepper, rice,
Seeds of corn, wheat, soybean, cotton, and beet were sown in spots, and the soil was covered by about 1 cm. When various plants reached the 2-3 leaf stage, the active ingredients were sprayed evenly on the foliage so that the amount of the active ingredient became a predetermined ratio.

As the drug solution for spraying, a formulation appropriately adjusted according to the above-mentioned formulation example, etc. was diluted with water and used, and this was sprayed on the entire surface of the foliage of various weeds with a small spray. 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 3. The compound No. in each table is the compound No. in the examples.
And the symbols have the following meanings.

N (Novier), M (Mexico), K (Cyperus vulgaris), H (Eggs), D (Beetle), I (Garden), R (Rice), T (Maize), W (Wheat), S ( Soybean), C (cotton), B
(beat)

[0098]                           Table 2 ────────────────────────────   Compound dose     No. (g / ha) N M K H D I R T W S C ────────────────────────────     1 40 5 5 5 5 5 5 5 1 3 0 0 ────────────────────────────     2 6 30 5 5 5 5 5 5 0 0 0 2 1 ────────────────────────────     3 6 30 5 5 5 5 5 5 4 4 4 4 2 ────────────────────────────

[0099]                           Table 3 ─────────────────────────────   Compound dose     No. (g / ha) N M K H D I R T W S C B ─────────────────────────────     1 160 5 5 5 5 5 5 5 4 5 4 5 5 ─────────────────────────────     2 630 2 0 2 5 4 5 0 0 0 3 3 0 ─────────────────────────────     3 6 30 5 5 5 5 5 5 5 4 3 4 4 1 ─────────────────────────────

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Kaoru Ito             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Hiroshi Kita             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Tsutomu Namaki             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory (72) Inventor Shigenomi Watanabe             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory (72) Inventor, Kimihiro Ishikawa             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory

Claims (4)

[Claims] 1. Formula (I): [Wherein R ⁴ represents a hydrogen atom or a halogen atom, and R 4
⁵ represents a halogen atom or a nitro group, R ⁶ represents a hydrogen atom, a halogen atom, a mercapto group, an amino group, CO ₂
A ¹ (A ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), OA ² (A ² is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl having 3 to 6 carbon atoms) Group, an alkynyl group having 3 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms), OCHA ³ CO
₂ A ⁴ (A ³ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, A ⁴ represents a hydrogen atom or 1 to 4 carbon atoms)
Represents an alkyl group. ), SCHA ³ CO ₂ A ⁴ (A ³
And A ⁴ have the same meanings as described above. ), NHCHA
³ CO ₂ A ⁴ (A ³ and A ⁴ have the same meanings as described above) or NHCO ₂ A ⁵ (A ⁵ has 1 to 1 carbon atoms).
6 represents an alkyl group of 6, a phenyl group which may be substituted, or a benzyl group which may be substituted by a phenyl ring. )
And Q is the formula (Wherein q ¹ , q ² , q ³ , q ⁴ , q ⁵ , q ⁶ , q ⁷ , q
⁸ , q ⁹ , q ¹⁰ , q ¹¹ , q ¹² , q ¹³ , q ¹⁴ , q ¹⁵ ,
q ¹⁶ , q ¹⁷ and q ¹⁸ each independently represent a hydrogen atom, a halogen atom or a methyl group, and X represents an oxygen atom or a sulfur atom. ) Represents. ] The condensed pyrimidinedione derivative represented by these. 2. Formula (I): [Wherein R ⁴ , R ⁵ and Q have the same meanings as in claim 1, R ⁶ represents a hydrogen atom, a halogen atom, a mercapto group,
CO ₂ A ¹ (A ¹ has the same meaning as in claim 1),
OA ² (A ² has the same meaning as in claim 1), OC
HA ³ CO ₂ A ⁴ (A ³ and A ⁴ have the same meanings as in claim 1) or SCHA ³ CO ₂ A ⁴ (A ³ and A ⁴ have the same meanings as in claim 1). Represent ]
The fused pyrimidinedione derivative according to claim 1, represented by: 3. Formula (I): [Wherein R ⁴ , R ⁵ and Q have the same meanings as in claim 1, R ⁶ is an amino group, NHCHA ³ CO ₂ A ⁴ (A ³
And A ⁴ have the same meanings as in claim 1. ) Or NHCO ₂ A ⁵ (R ⁵ has the same meaning as in claim 1). ] The condensed pyrimidinedione derivative of Claim 1 represented by these. 4. A herbicide containing the fused pyrimidinedione derivative according to claim 1.