JPH0678339B2 - Fused heterocycle derivative - Google Patents

Description

The present invention relates to a novel fused heterocyclic derivative and a herbicide containing the compound as an active ingredient.

It is indispensable to use herbicides to protect important crops such as rice, wheat, cotton, beet, corn and soybean from weed damage and increase yield. Particularly in recent years, in arable land where these useful crops and weeds are mixed, a selective herbicide capable of selectively killing only the weeds without showing phytotoxicity to the crops even when the crops and the weeds are simultaneously treated is desired. . In addition, from the viewpoints of preventing environmental pollution, reducing economic costs for transportation, and spraying, research and exploration of compounds that show high herbicidal effect with a low dose is continued for many years. Although some of the compounds with such properties are currently used as selective herbicides, there is still a need for new compounds with these properties.

The present inventors have continued to study for many years to develop a herbicide having selectivity for important crops, and to produce a compound having higher herbicidal activity and selectivity, many compounds have herbicidal properties. Have been considering. as a result,
Formula (I) below [In the formula, X is a hydrogen atom or a halogen atom, Z is an oxygen atom or a sulfur atom, and J is -CO- or -CS.
-, - SO ₂ -, or a _{-CR 2 (R 2), R} 2 and R ₃ are each independently a hydrogen atom, an alkyl of 1 to 6 carbon atoms, -CO ₂ Ra (where, Ra is carbon Represents an alkyl having 1 to 6 atoms), -CONRc (Rd) (wherein Rc and Rd each independently represent hydrogen or alkyl having 1 to 6 carbon atoms), or a halogen atom or 1 carbon atom. ~ 6 haloalkyl, alkyl having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally substituted by an alkoxy or nitro group of ~ 6, L ₁ is -CO- or -CR ₄ (R
₅ )-, and R ₄ and R ₅ are each independently a hydrogen atom, alkyl having 1 to 6 carbon atoms, hydroxymethyl,
Haloalkyl having 1 to 6 carbon atoms, (the Ra as defined above.) Alkoxyalkyl, -CO ₂ Ra of 2 to 6 carbon atoms or a halogen atom, a haloalkyl having 1 to 6 carbon atoms, carbon atoms A phenyl group which may be substituted with 1 to 6 alkoxy or nitro group, R ₁
Is a hydrogen atom, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 3 to 6 carbon atoms,
Alkoxyalkyl having 2 to 6 carbon atoms, 1 carbon atom
~ 6 haloalkyl, C2-6 haloalkenyl, C3-6 haloalkynyl, C3
8 _{cycloalkyl, -CORb, -CO 2 Rb, -CH} 2 CO 2 Rb
(However, Rb is alkyl having 1 to 6 carbon atoms, and has 3 carbon atoms.
Represents cycloalkyl having 6 to 6, alkenyl having 3 to 6 carbon atoms, and alkynyl having 3 to 6 carbon atoms. ), −CON
_{(Rc) Rd, -CH 2 CON} (Rc) Rd, -CH 2 CN, -CH 2 P (Z) R
c (Rd) (provided that Rc, Rd and Z have the same meanings as described above), (However, Re and Rf each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, a nitro group, a haloalkyl having 1 to 6 carbon atoms or a halogen atom.) And W is , Q is a nitrogen atom or —CH, E is an oxygen atom or a sulfur atom, n is an integer of 1 to 3, and Y is
Is a halogen atom, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms or alkylsulfonyl having 1 to 6 carbon atoms, and A is a hydrogen atom or a carbon atom. Alkyl having 1 to 6 and R ₁₀ , R ₁₁ , R ₁₄ and R ₁₅ are each independently a hydrogen atom, a halogen atom, an alkyl having 1 to 6 carbon atoms,
Alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms, R ₁₂ is hydrogen atom when Q is a nitrogen atom, alkyl having 1 to 6 carbon atoms. Alternatively, it is a haloalkyl having 1 to 6 carbon atoms, and when Q is CH, a hydrogen atom and a carbon atom having 1 to 1
6 alkyl, haloalkyl having 1 to 6 carbon atoms or alkylene having 4 carbon atoms forming a 6-membered ring by bonding with Q, and when R ₁₃ is a nitrogen atom, hydrogen atom, 1 to 1 carbon atom 6 alkyl or haloalkyl having 1 to 6 carbon atoms, when Q is CH, hydrogen atom, 1 carbon atom
When alkyl of ˜6, haloalkyl having 1 to 6 carbon atoms or R ₁₂ is alkylene having 4 carbon atoms which is bonded to Q to form a 6-membered ring, it is bonded to this to form a 6-membered ring. ] Or the following formula (II) [Wherein, X, Z, L ₁ , J, R ₁ and W have the same meanings as described above, L ₂ is —CO— or CR ₆ (R ₇ ), and R ₆ and R ₇ are each independently 1 to 1 hydrogen atom or carbon atom
An alkyl of 6. ] The fused heterocyclic derivative represented by the following (hereinafter referred to as the compound of the present invention) has a strong herbicidal activity against many weeds in both cases of soil treatment and foliage treatment, and also for important crops. The present invention has been completed by finding that it has high safety.

In particular, some of these compounds have selectivity for soybean and beet. Further, some of the compounds of the present invention show selectivity to rice, wheat, cotton, corn, etc. as well as dies and beets.

On the other hand, the compound of the present invention exhibits a high herbicidal activity at a very low dose as compared with conventional herbicides, and is therefore also useful as a herbicide for orchards and non-arable land.

The compounds of the present invention represented by formulas (I) and (II) are described below in a) to
It can be easily synthesized by selecting the method of c). That is, a) Formula (III) (IV) (Wherein X, Z, L ₁ , L ₂ , J and R ₁ have the same meanings as described above), a compound represented by the formula (A) or (B) (In the formula, R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , E and Q have the same meanings as described above. R ₂₀ represents C _1-5 alkyl.
_1-5 has the meaning of having 1 to 5 carbon atoms, and will be abbreviated similarly hereinafter. ) By reacting with a compound of formula (Ia) and (IIa) [In the formula, Wa is selected from the groups (W1) and (W2) defined above, and X, Z, L ₁ , L ₂ , J and R ₁ have the same meanings as described above. ] The compound shown by these is obtained.

Further, a compound represented by the formula (Ia) or (IIa) (Wa is W
(In the case of 1) is reduced or further reduced and then alkylated to obtain the compound of formula (Ib) or (IIb) [Wherein _{W3, X, Z, L 1} , L 2, J and R ₁ are as defined above. ] The compound shown by these is obtained.

b) Formula (V) (VI) [In the formula, X, Z, E, L ₁ , L ₂ , J and R ₁ have the same meanings as described above. Wc is the formula (C) (In the formula, R ₁₂ , R ₁₃ , R ₂₀ and Q have the same meanings as described above.) The compounds (Ic) and (IIc) Or (wherein _{W2, X, Z, L 1} , L 2, J and R _1. Represent the same meanings as defined above) to obtain a compound represented by, or, c) formula (VII) (VIII) (Wherein X, Z, L ₁ , L ₂ , J and R ₁ have the same meanings as described above), and a compound represented by the formula (D) or (E) (In the formula, n and R ₂₀ have the same meanings as described above. R ₂₁ represents C _1-6.
(Representing alkyl) by reacting a compound of formula (Id) and (IId) [Wherein X, Z, L ₁ , L ₂ , J and R ₁ represent the same meaning as described above, Wd
Is the formula (F) or (G) (Wherein n and R ₂₁ have the same meanings as described above)]. Further, by reacting a compound represented by the formula (Id) or (IId) (when Wd is (F)] with a halogenating agent, the compound represented by the formula (Ie) or (IIe) [In the formula, X, Z, L ₁ , L ₂ , J and R ₁ have the same meanings as described above. W
e is the formula (H) (In the formula, X has the same meaning as described above, except for a hydrogen atom.)]. In addition, a compound represented by the formula (Id) or (IId) [when Wd is (F)] is
Formula (If) or (IIf) by reacting with an alkylating agent [Wherein X, Z, L ₁ , L ₂ , J or R ₁ has the same meaning as described above. W
f is the formula (J) (In the formula, n represents the same meaning as described above. R ₂₂ represents C _1-6 alkyl)].

Next, the synthesis methods a) to c) will be described in more detail.

The conditions for obtaining the compounds (Ia) and (IIa) from the compounds (III) (IV) by the reaction according to the method a) are as follows: room temperature to 200 ° C., for example, 100 ° C. or reflux temperature for 30 minutes to 24 hours. preferable. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as dioxane, ethylene glycol and diethyl ether, fatty acids such as formic acid and acetic acid, haloalkanes such as chloroform and methylene chloride, or a mixture thereof. To be When the reaction partner is the anhydride (A), it is preferable to carry out the reaction in the presence of an acid such as acetic acid.

The conditions for obtaining the compounds (Ib) and (IIb) from the compounds (Ia) and (IIa) are −70 ° C. to 100 ° C., for example, -10 ° C. to 30 ° C.
It is preferable that the reaction is carried out for 1 minute to 12 hours. As a solvent
Examples thereof include alkanes such as hexane and pentane, alcohols such as methanol and ethanol, ethers such as dioxane, diethyl ether and tetrahydrofuran, water and the like, or a mixture thereof. Na as a reduction method
Reduction of BH ₄ , KBH ₄ , LiAlH ₄ etc. can be mentioned. Preferably,
It is advisable to carry out the reduction with NaBH ₄ or KBH ₄ in a protic solvent.

The conditions for obtaining the compounds (Ic) and (IIc) from the compounds (V) and (VI) by the reaction according to the method b) are the compounds (V) and (VI).
0.01 to 1 equivalent of a base in a solvent at 10 ° C to 100
Intramolecular ring closure is preferably carried out by reacting at 10 ° C for 10 minutes to 24 hours.

As a solvent, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene, aromatic hydrocarbons such as xylene, chloroform, methylene chloride, halogenated hydrocarbons such as chlorobenzene, diethyl ether, Ethers such as dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol and ethanol, nitriles such as acetonitrile and isobutyronitrile, and tertiary amines such as pyridine and N, N-diethylaniline. Acid amides such as formamide and N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, and mixtures thereof.

Examples of the base include organic bases such as pyridine, triethylamine and N, N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, sodium methoxide, sodium ethoxide and the like. Examples thereof include alkali metal alkoxides.

The conditions for obtaining the compounds (Id), (IId) from the compounds (VII), (VIII) in the reaction according to the method c) are room temperature to 200 ° C., for example, 80 ° C. to 150 ° C., and reflux dehydration for 30 minutes to 48 hours. It is preferable. Benzene, toluene as solvent
Examples thereof include aromatic hydrocarbons such as xylene, alcohols such as methanol, ethanol and butanol, ethers such as dioxane and tetrahydrofuran, or a mixture thereof.

The conditions for obtaining compounds (Ie) and (IIe) from compounds (Id) and (IId) are as follows: 60 ° C to 180 ° C, 30 minutes to 24 hours, phosphorus oxychloride, phosphorus oxybromide, thionyl chloride, bromide. It is preferable to react with a halogenating agent such as thionyl or phosgene and optionally an inert solvent such as chloroform, methylene chloride or toluene. In this case, pyridine, N, N-dimethylaniline, N, N-dimethylformamide or the like can be added to accelerate the reaction.

Further, the conditions for obtaining (If) (IIf) from the compound (Id) (IId) [in this case, when Wd is (F)] are dimethylsulfate,
-10 ℃ with alkylating agents such as diethylsulfate and diazomethane
It is preferable to carry out the reaction at 1 to 80 ° C. for 1 to 24 hours. When an alkylsulfate such as dimethylsulfate or diethylsulfate is used as the solvent, an aqueous solution containing an inorganic base such as sodium hydroxide, potassium hydroxide or sodium carbonate is preferable. When diazomethane is used, ethers such as diethyl ether and dioxane, alcohols such as methanol and ethanol, or a mixture thereof is preferable.

The starting materials and reagents used in the above methods are known or are prepared by methods similar to those described above or known.

The synthesis examples of the compound of the present invention and the intermediate will be specifically described below as Examples and Reference Examples, but the present invention is not limited thereto.

Example 1 (Synthesis of compound No. 1-8 of the present invention) 6-amino-7-fluoro-4-propargyl-2H-1,
A mixture of 0.50 g of 4-benzoxazin-3 (4H) -one, 0.34 g of 2,3-dimethylmaleic anhydride and 5 ml of acetic acid was heated under reflux for 4 hours.

The acetic acid was distilled off under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and water in this order, dried, and concentrated. The residue thus obtained is reconstituted (benzene: chloroform: ethyl alcohol = 1
0: 4: 1) and N- (7'-fluoro-4'-propargyl-2'H-1 ', 4'-benzoxazine-3' (4 '
H) -On-6'-yl) -2,3-dimethylmaleimide
0.10 g was obtained. Melting point 234-235 ° C.

Example 2 (Synthesis of compound No. 5-5 of the present invention) N- (7'-fluoro-4'-propargyl-2'H-
1 ', 4'-Benzoxazin-3'(4'H) -one-
6'-yl) -2,3-dimethylmaleimide 0.35g in THF 30m
l, dissolved in 10 ml of methanol, sodium borohydride
0.50 g was added slowly at 0 ° C. After 30 minutes, the mixture was poured into ice water, extracted with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, and distilled off with ethyl acetate to give N- (7'-fluoro-4'-propargyl-2'H-1. 0.30 g of ', 4'-benzxazin-3'(4'H)-one-6'-yl) -3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole was obtained. Melting point 101.5-103.5 ° C.

Example 3 (Synthesis of Compound No. 1-31 of the present invention) 4-acetyl-6-amino-3,4-dihydro-7-fluoro-2H-1,4-benzoxazinne 1.00 g, 2,3-dimethyl A mixture of 0.60 g of maleic anhydride and 10 ml of acetic acid was heated under reflux for 6 hours. The acetic acid was distilled off under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated saline in this order, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was recrystallized from ethanol to give N- (4'-acetyl-3 ', 4'-dihydro-
0.76 g of 7'-fluoro-2'H-1 ', 4'-benzoxazin-6'-yl) -2,3-dimethylmaleimide was obtained as light brown crystals. Melting point 180-181 ° C.

Reference Example 1 (Synthesis of 3,4-dihydro-7-fluoro-2H-1,4-benzoxane) In a solution prepared by suspending 6.76 g of lithium aluminum hydride in 500 ml of THF, 7-fluoro-2H-1,4- A solution of 20 g of benzoxazin-3 (4H) -one in 200 ml of THF was added to 0.
The solution was gradually added dropwise at a temperature of not higher than 0 ° C. After the dropping, the mixture was heated and kept at the THF reflux temperature for 3 hours, then cooled again to 0 ° C. or lower, and excess lithium aluminum hydride was decomposed by adding water. A 10% aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off to obtain 17.0 g of the target compound as a brown oil.

Reference Example 2 (Synthesis of 4-acetyl-3,4-dihydro-7-fluoro-2H-1,4-benzoxazine) 3,4-dihydro-7-fluoro-2H-1,4-benzoxazine 16.7 g, Triethylamine 11.6g, chloroform 194m
The mixed solution of 1 is cooled to 5 ° C or lower, and acetyl chloride is added.
3.53 g was added dropwise. After 2 hours, water was added to separate the chloroform layer, which was then washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and distilled off chloroform to obtain 23.9 g of the target compound as a brown solid.

Reference Example 3 (Synthesis of 4-acetyl-3,4-dihydro-7-fluoro-6-nitro-2H-1,4-benzoxazine) 4-Acetyl-3,4-dihydro-7-fluoro-2H-1, Four
-23.9 g of benzoxazine was dissolved in 80% sulfuric acid, and 14.5 g of 60% nitric acid was added dropwise at 5 ° C or lower. After dropping, warm up to room temperature, 2
After a while, the reaction solution was poured into ice water. The resulting yellow crystals were filtered, washed with water and dried to obtain 22.4 g of the target compound. Melting point 158-160 ° C.

Reference Example 4 (Synthesis of 4-acetyl-6-amino-3,4-dihydro-7-fluoro-2H-1,4-benzoxazine) 4-Acetyl-3,4-dihydro-7-fluoro-6-nitro -2H-1,4-Benzoxazine 8.00g, acetic acid 34ml, ethyl acetate 34ml mixed solution, iron powder 18.6g and 5% acetic acid 36ml
Was gradually added dropwise to the mixed solution of about 80 ° C. After dropping, reflux 2
After 30 minutes, the iron powder was filtered and the ethyl acetate layer was separated.
The aqueous layer was extracted with ethyl acetate for 2 hours, combined, and washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and distilled to remove ethyl acetate to give crude crystals. Got This was washed with isopropyl ether to obtain 4.48 g of the target compound as brown crystals.

Melting point 105-107 ° C.

Next, examples of compounds included in the present invention are shown in Tables 1 to 8 and the compounds synthesized in the above Examples, but the compounds of the present invention are not limited to these.

When the compound of the present invention is applied as a herbicide, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene , Toluene, xylene, etc.), ethers, ketones, esters (ethyl acetates, etc.), acid amides (dimethylformamide, etc.), etc. A dispersant, a suspending agent, a penetrating agent, a spreading agent, a stabilizer, etc. may be added to the emulsion, a wettable powder, a powder, a granule, or the like for practical use.

In addition, various herbicides at the time of formulation or spraying [eg, Farm Chemical Handbook 70 . (1984)
Compounds described in 1), various insecticides, bactericides, synergists, and the like may be applied in mixture.

Next, specific examples of formulation of the preparation when the compound of the present invention is used are shown. Parts indicate weight. However, the compounding examples of the present invention are not limited to these.

Formulation Example 1 Wettable powder Compound of the present invention No.1-8 ...... 50 parts Diklite PFP ...... 43 parts (Kaolin clay: product name Sieglite Co., Ltd.) Solpol 5039 ...... 5 parts (Nonionic interface Mixture of activator and anionic surfactant: Toho Chemical Co., Ltd. trade name Carplex (anti-caking agent) …… 2 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) Crush into wettable powder.

Formulation Example 2 Emulsion Compound No. 5-5: 5 parts Xylene: 60 parts Dimethylformamide: 25 parts Solpol 2680: 10 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd. trade name) Mix the above uniformly to make an emulsion.

Formulation example 3 Flowable agent Compound of the present invention No.1-6 ...... 25 parts Agrizone S-710 ...... 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C ...... 0.5 part (Anionic Surfactant: Toho Kagaku Co., Ltd. product name) 1% Rhodball water ...... 20 parts (Thickener: Lone Poulean Company product name) Water ...... 44.5 parts Mix evenly to make a flowable agent.

Formulation Example 4 Granules Compound of the present invention No.1-8 ...... 0.5 parts Bentonite ...... 55.0 parts Talc ...... 44.5 parts After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is kneaded with stirring, and extruded. Granulate with a granulator and dry to make granules.

When using the above wettable powder, emulsion, flowable agent with water
Dilute 50 to 1000 times, 0.01 to 10k active ingredient per ha
Scatter so that the ratio is g.

The compound of the present invention can be applied to the removal of various weeds in non-agricultural fields such as fields, paddy fields, orchards as well as agricultural and horticultural fields, open spaces, track ends, etc. , 0.01 to 10 per hectare (ha), although there are differences depending on the application period, target grass species, cultivated crops, etc.
A rate of about kg is appropriate.

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 15 cm in height, 22 cm in width, and 6 cm in depth put sterilized diluvial soil in a plastic box, and then Novier, Crabgrass, Cyperus,
Codling of dogwood, Japanese barley, dogwood, rice, corn, wheat, soybean, and cotton was mixed and sown for about 1.5 cm, and then sprayed uniformly on the soil surface so that the amount of active ingredient was a predetermined ratio. The chemical solution was prepared by diluting the wettable powder, emulsion or flowable agent of the above formulation with water and spraying it over the entire surface with a small spray. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds was investigated according to the following criteria.

Judgment criteria 5 …… 90% or more of weeding (almost complete death) 4 …… 70 ~ 90% of weeding 3 ・ ・ ・ 40-70% of weeding 2 …… 20-40% of weeding 1 …… 5-20 of weeding % 0 ... 5% or less herbicidal rate (almost no effect) However, the above-mentioned herbicidal rate is obtained by measuring the above-ground weed weight of the chemical treatment area and the above-ground weed weight of the untreated area according to the following formula. It was.

In addition, the chemical damage to various crops was investigated according to the following criteria. The results are shown in Table 9.

Judgment criteria 5 ... Almost complete death of crops 4 ... Significant phytotoxicity on crops 3 ... Recognized phytotoxicity on crops 2 ... Some phytotoxicity on crops 1 ... Almost no phytotoxicity on crops 0 ... No phytotoxicity to crops Test Example-2 Herbicidal effect test by foliar treatment 30 cm long, 22 cm wide, and 6 cm deep put sterilized diluvial soil in a plastic box and cultivated Nobye, Crabgrass, Cyperus
Seeds of dogwood, Japanese barley, dogwood, and beet were sown in spots and covered with soil for about 1.5 cm.
When various value products reached the 2-3 leaf stage, they were uniformly sprayed on the foliage so that the amount of the active ingredient became a predetermined ratio.

The chemical solution for spraying was prepared by diluting the wettable powder, emulsion or flowable agent of the above formulation example with water and spraying it over the entire surface of the foliage of various weeds and crops with a small spray. The herbicidal effect against various weeds or the phytotoxicity against various crops was investigated 4 weeks after the chemical liquid cloth according to the criteria of Test Example-1. The results are shown in Table 10.

Continuation of front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07D 413/04 249 7602-4C 413/14 207 7602-4C 417/04 207 9051-4C 419/04 9051-4C (72) Shigeaki Akiyama 1 722, Tsuboi-cho, Funabashi-shi, Chiba Central Research Laboratory, Nissan Chemical Industry Co., Ltd. (72) Takashi Inokai 1470 Shiraoka, Shiraoka-cho, Minami Saitama-gun, Saitama Nissan Biochemical Research Institute ( 72) Inventor Tsutomu Namaki 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture Biochemical Research Institute, Nissan Chemical Industry Co., Ltd. Examiner Masato Ikeda

Claims (2)

[Claims] 1. A formula (I) [In the formula, X is a hydrogen atom or a halogen atom, Z is an oxygen atom or a sulfur atom, and J is -CO- or -CS.
-, - SO ₂ - or a -CR ₂ (R _3), R ₂ and R ₃ are independently a hydrogen atom, an alkyl of 1 to 6 carbon atoms, -CO ₂ Ra (where, Ra is a carbon atom Formula 1-6 alkyl), -CONRc (Rd) (wherein Rc and Rd each independently represent hydrogen or C1-6 alkyl), or a halogen atom, C1-6. Haloalkyl, alkyl having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally substituted by an alkoxy or nitro group of ~ 6, L ₁ is -CO- or -CR ₄ (R
₅ )-, and R ₄ and R ₅ are each independently a hydrogen atom, alkyl having 1 to 6 carbon atoms, hydroxymethyl,
Haloalkyl having 1 to 6 carbon atoms, (the Ra as defined above.) Alkoxyalkyl, -CO ₂ Ra of 2 to 6 carbon atoms or a halogen atom, a haloalkyl having 1 to 6 carbon atoms, carbon atoms A phenyl group which may be substituted with 1 to 6 alkoxy or nitro group, R ₁
Is a hydrogen atom, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 3 to 6 carbon atoms,
Alkoxyalkyl having 2 to 6 carbon atoms, 1 carbon atom
~ 6 haloalkyl, C2-6 haloalkenyl, C3-6 haloalkynyl, C3
8 _{cycloalkyl, -CORb, -CO 2 Rb, -CH} 2 CO 2 Rb
(However, Rb is alkyl having 1 to 6 carbon atoms, and has 3 carbon atoms.
Represents cycloalkyl having 6 to 6, alkenyl having 3 to 6 carbon atoms, and alkynyl having 3 to 6 carbon atoms. ), −CON
_{(Rc) Rd, -CH 2 CON} (RC) Rd, -CH 2 CN, -CH 2 P (Z) Rc (Rd) ( where Rc, Rd and Z are as defined above.), - CH ₂ Si (CH ₃ ) ₃ , (However, Re and Rf each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, a nitro group, a haloalkyl having 1 to 6 carbon atoms, or a halogen atom.) And W is , Q is a nitrogen atom or —CH, E is an oxygen atom or a sulfur atom, n is an integer of 1 to 3, and Y is
Is a halogen atom, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms or alkylsulfonyl having 1 to 6 carbon atoms, and A is a hydrogen atom or a carbon atom. Alkyl having 1 to 6 and R ₁₀ , R ₁₁ , R ₁₄ and R ₁₅ are each independently a hydrogen atom, a halogen atom, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, Alkylthio having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms, and when R ₁₂ is a nitrogen atom, hydrogen atom, alkyl having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms. And when Q is CH, a hydrogen atom and a carbon number of 1 to 6
Alkyl, haloalkyl having 1 to 6 carbon atoms or Q
Is a alkylene having 4 carbon atoms which forms a 6-membered ring by combining with, and R ₁₃ is hydrogen atom, alkyl having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms when Q is a nitrogen atom. , Q is CH, hydrogen atom, carbon atom 1
When ~ 6 alkyl, haloalkyl having 1 to 6 carbon atoms or R ₁₂ is alkylene having 4 carbon atoms which is bonded to Q to form a 6-membered ring, it is bonded to to form a 6-membered ring. ] Or formula (II) [Wherein, X, Z, L ₁ , J, R ₁ and W have the same meanings as described above, L ₂ is —CO— or CR ₆ (R ₇ ), and R ₆ and R ₇ are each independently And hydrogen atom or alkyl having 1 to 6 carbon atoms. ] The compound represented by these. 2. Formula (I) [In the formula, X is a hydrogen atom or a halogen atom, Z is an oxygen atom or a sulfur atom, and J is -CO- or -CS.
-, - SO ₂ -, or a _{-CR 2 (R 3), R} 2 and R ₃ are each independently a hydrogen atom, an alkyl of 1 to 6 carbon atoms, -CO ₂ Ra is 1 carbon atoms Represents an alkyl of 6. ), -CONRc (Rd) (wherein Rc and Rd each independently represent hydrogen or alkyl having 1 to 6 carbon atoms), or a halogen atom, haloalkyl having 1 to 6 carbon atoms, or 1 carbon atom. ~ 6 alkyls, 1 carbon atoms
A phenyl group optionally substituted by an alkoxy or nitro group of ~ 6, L ₁ is -CO- or -CR ₄ (R
₅ )-, and R ₄ and R ₅ are each independently a hydrogen atom, alkyl having 1 to 6 carbon atoms, hydroxymethyl,
Haloalkyl having 1 to 6 carbon atoms, (the Ra as defined above.) Alkoxyalkyl, -CO ₂ Ra of 2 to 6 carbon atoms or a halogen atom, a haloalkyl having 1 to 6 carbon atoms, carbon atoms A phenyl group which may be substituted with 1 to 6 alkoxy or nitro group, R ₁
Is a hydrogen atom, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 3 to 6 carbon atoms,
Alkoxyalkyl having 2 to 6 carbon atoms, 1 carbon atom
6 of haloalkynyl, haloalkenyl of 2 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, having 3 to 8 carbon atoms in the _{cycloalkyl, -CORb, -CO 2 Rb, -CH} 2 CO 2 R
b (however, Rb represents alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl having 3 to 6 carbon atoms, alkynyl having 3 to 6 carbon atoms), -CON.
_{(Rc) Rd, -CH 2 CON} (Rc) Rd, -CH 2 CN, -CH 2 (Z) Rc
(Rd) (provided that Rc, Rd and Z have the same meanings as described above), (However, Re and Rf each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, a nitro group, a haloalkyl having 1 to 6 carbon atoms or a halogen atom.) And W is , Q is a nitrogen atom or —CH, E is an oxygen atom or a sulfur atom, n is an integer of 1 to 3, and Y is
Is a halogen atom, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms or alkylsulfonyl having 1 to 6 carbon atoms, and A is hydrogen atom or carbon atom 1 to 6 alkyl, and R ₁₀ , R ₁₁ , R ₁₄ and R ₁₅ are each independently a hydrogen atom, a halogen atom, an alkyl having 1 to 6 carbon atoms, an alkoxy having 1 to 6 carbon atoms, a carbon atom. Alkylthio having 1 to 6 atoms or haloalkyl having 1 to 6 carbon atoms, R ₁₂ is hydrogen atom, alkyl having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms when Q is a nitrogen atom; , Q is CH, hydrogen atom, carbon atom number 1 to 6
Alkyl, haloalkyl having 1 to 6 carbon atoms or Q
Is a alkylene having 4 carbon atoms which forms a 6-membered ring by combining with, and R ₁₃ is hydrogen atom, alkyl having 1 to 6 carbon atoms or haloalkyl having 1 to 6 carbon atoms when Q is a nitrogen atom. , Q is CH, hydrogen atom, carbon atom 1
When alkyl of ˜6, haloalkyl having 1 to 6 carbon atoms or R ₁₂ is alkylene having 4 carbon atoms which is bonded to Q to form a 6-membered ring, it is bonded to this to form a 6-membered ring. ] Or formula (II) [Wherein, X, Z, L ₁ , J, R ₁ and W have the same meanings as described above, L ₂ is —CO— or CR ₆ (R ₇ ), and R ₆ and R ₇ are each independently And hydrogen atom or alkyl having 1 to 6 carbon atoms. ] The herbicide which contains the compound represented by these as an active ingredient.