JP2003055346A - Tetrahydrophalimide, use and synthetic intermediate thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide compounds having excellent herbicidal effect. SOLUTION: The tetrahydrophthalimide is presented by formula [VII] [wherein X is a halogen atom (e.g. fluorine, chlorine, bromine), Y is a halogen (e.g. fluorine, chlorine, bromine), R<5> is a 1-3C alkyl (e.g. methyl, ethyl, propyl) or a 1-3C haloalkyl (e.g. trifluoromethyl)] and a herbicide containing the compound as an active ingredient is provided.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a tetrahydrophthalimide compound and a herbicide containing the compound as an active ingredient.

[0002]

2. Description of the Related Art At present, many herbicides are commercially available and used, but since many kinds of weeds are controlled, and their outbreaks are long-term, the herbicidal effect is higher and the herbicidal spectrum is wide. However, there is a demand for a herbicide that does not cause a problem of chemical damage to crops. JP-A-63-280060
The publication discloses that certain tetrahydrophthalimide compounds have herbicidal activity, but the tetrahydrophthalimide compounds described herein do not always have sufficient performance in terms of herbicidal activity.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a compound having excellent herbicidal activity.

[0004]

Means for Solving the Problems As a result of intensive investigations by the present inventors to find a compound having excellent performance as a herbicide, a tetrahydrophthalimide compound represented by the following formula [VII] has excellent performance as a herbicide. The present invention has been completed, and has led to the present invention. That is, the present invention has the formula [VII] [In the formula, X represents a halogen atom, Y represents a halogen atom, and R ⁵ represents a C1-C3 alkyl group or a C1-C3 haloalkyl group. ] A tetrahydrophthalimide compound represented by the following (hereinafter referred to as the compound of the present invention) and a herbicide containing the same as an active ingredient are provided. The present invention further provides some novel compounds useful as intermediates for the preparation of the compounds of the present invention.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, the halogen atom represented by X means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the halogen atom represented by Y is a fluorine atom, a chlorine atom, R ⁵ means a bromine atom or an iodine atom.
The C1-C3 alkyl group represented by is a methyl group,
Ethyl group, propyl group, isopropyl group, and C
Examples of the 1-C3 haloalkyl group include a chloromethyl group, a bromomethyl group, a fluoroethyl group, a 2-chloroethyl group, a 1-chloroethyl group and a trifluoromethyl group, and as the C1-C6 alkyl group represented by R ⁶ ,
Examples of the C1-C6 alkoxy group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a t-butyl group (here, t- means tertiary).
Examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group and a butoxy group. In the compound of the present invention, X is a fluorine atom, and Y is a chlorine atom as a substituent preferable from the viewpoint of herbicidal effect.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention can be produced, for example, by the production method described in the following [Production Method 1] and / or [Production Method 2]. [Production Method 1] A method for producing the compound [VII] of the present invention from the compound [X] by the production route shown in the following scheme. [Wherein, X, Y and R ⁵ have the same meanings as described above, and R ⁶
Represents a C1-C6 alkyl group, a C1-C6 alkoxy group or a phenoxy group, L ¹ represents a fluorine atom or a chlorine atom, L ² represents a fluorine atom or a chlorine atom, L ³
Represents a chlorine atom or a bromine atom. ]

(Step 1-1) The reaction is carried out by reacting the compound represented by the formula [X] with the compound represented by the formula [VIII] in the presence of a base, usually in a solvent. Reaction temperature: 0 ° C to 50 ° C Reaction time: Instant to 48 hours Base: Organic bases such as pyridine, picoline, lutidine, dimethylaminopyridine, triethylamine, etc. Amount of base: 0.5 mol per 1 mol of compound [X] ~ 5
Mole ratio. Amount of the compound represented by the formula [VIII] used in the reaction: 0.5 mol to 2 mol per 1 mol of the compound [X]. Solvents used: N, N-dimethylformamide (hereinafter referred to as DMF), acid amides such as N, N-dimethylacetamide, hydrocarbons such as hexane, heptane, toluene, xylene, cyclohexane, tetrahydrofuran (hereinafter, THF), ethers such as 1,4-dioxane, dimethoxyethane, diethoxyethane, di (2-methoxyethyl) ether, tri (ethyleneglycol) dimethylether, and ketones such as acetone, methylethylketone, methylisobutylketone, and cyclohexanone. , Acetonitrile, nitrile compounds such as propionitrile, chlorobenzene, halogen compounds such as dichlorobenzene and the like after completion of the mixture reaction, water is added to the reaction mixture, or the resulting crystals are collected by filtration, or Water in the reaction mixture Adding performs normal post-treatment such as organic solvent extraction and concentration, it is possible to obtain the desired compound. The compound can also be purified by operations such as chromatography and recrystallization. Further, the compound represented by the formula [I] is the same as the compound represented by the formula [X] [In the formula, R ⁶ represents the same meaning as described above. ] The compound shown by the above can also be produced by reacting in the presence of a protic acid, usually in a solvent.

(Step 1-2) The reaction is carried out by reacting the compound represented by the formula [I] and the compound represented by the formula [II] in the presence of a base, usually in a solvent. Reaction temperature: 10 ° C to 50 ° C when L ¹ is a fluorine atom,
When L ¹ is a chlorine atom, it is preferably room temperature to 120 ° C. Reaction time: Instantaneous to 48 hours Amount of the compound represented by the formula [II] subjected to the reaction: relative to 1 mol of the compound represented by the formula [I] , 0.5 mol ~
2 mole ratio. Bases used: pyridine, picoline,
Organic bases such as lutidine, dimethylaminopyridine, triethylamine, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium hydride, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate,
Amount of inorganic base such as potassium fluoride: To 1 mol of the compound represented by the formula [I],
Ratio of 0.5 mol to 2 mol. Solvents used: acid amides such as DMF, N, N-dimethylacetamide, hydrocarbons such as hexane, heptane, toluene, xylene, cyclohexane, THF, 1,
Ethers such as 4-dioxane, diethoxyethane, di (2-methoxyethyl) ether and tri (ethyleneglycol) dimethylether, ketones such as acetone, methylethylketone, methylisobutylketone, cyclohexanone, nitriles such as acetonitrile and propionitrile. After completion of the reaction of the compounds, halogen compounds such as chlorobenzene and the mixture thereof, water is added to the reaction mixture and the resulting crystals are collected by filtration, or water is added to the reaction mixture and the mixture is extracted with an organic solvent and concentrated. The desired compound can be obtained by performing a usual post-treatment operation such as. The compound can also be purified by operations such as chromatography and recrystallization.

(Step 1-3) The reaction is carried out by hydrogenating the compound represented by the formula [III] in a solvent in the presence of a catalyst. Reaction temperature: room temperature to 50 ° C. Reaction time: Instant to 48 hours Catalyst: Palladium-carbon, nickel catalyst, ruthenium catalyst, etc. Solvents used: Hexane, heptane, toluene, xylene, hydrocarbons such as cyclohexane, THF, 1, Four
-Dioxane, diethyl ether, dibutyl ether,
Ethers such as diphenyl ether, dimethoxyethane, diethoxyethane, di (2-methoxyethyl) ether and tri (ethylene glycol) dimethyl ether; alcohols such as methanol, ethanol and isopropanol; organic acids such as formic acid, acetic acid and propionic acid, and After the completion of the reaction of these mixtures, water is added to the reaction mixture and the resulting crystals are collected by filtration, or ordinary post-treatment operations such as adding water to the reaction mixture and extracting and concentrating with an organic solvent are performed, The target compound can be obtained. The compound can also be purified by operations such as chromatography and recrystallization. The reaction can also be carried out according to the method described in "Reduction General", p159-266, 4th edition Experimental Chemistry Course 26 (Maruzen Co., Ltd.).

(Step 1-4) The reaction is carried out by reacting the compound represented by the formula [IV] with the compound represented by the formula [V] in the presence of a base, usually in a solvent. Reaction temperature: Room temperature to 120 ° C. Reaction time: Instantaneous to 48 hours Amount of compound represented by the formula [V] subjected to reaction: Formula [I
V] 0.5 mol to 2 mol with respect to 1 mol of the compound represented by
Mole ratio. Base used: organic base such as pyridine, picoline, lutidine, dimethylaminopyridine, triethylamine, etc. Amount of base: 1 mol of the compound represented by the formula [IV],
Ratio of 0.1 mol to 2 mol. Solvents used: acid amides such as DMF, N, N-dimethylacetamide, hydrocarbons such as hexane, heptane, toluene, xylene, cyclohexane, THF, 1,
Ethers such as 4-dioxane, diethoxyethane, di (2-methoxyethyl) ether, and tri (ethyleneglycol) dimethylether, nitrile compounds such as acetonitrile and propionitrile, halogen compounds such as chlorobenzene, and mixtures thereof. After completion of the reaction, water is added to the reaction mixture and the resulting crystals are collected by filtration, or ordinary post-treatment operations such as water addition to the reaction mixture and extraction with an organic solvent and concentration are carried out to obtain the target compound. be able to. The compound can also be purified by operations such as chromatography and recrystallization. In addition, the compound represented by the formula [VI] is the compound represented by the formula [IV] and the compound represented by the formula [V-1] [In the formula, R ⁵ represents the same meaning as described above. ] The compound shown by the above can also be produced by reacting with a compound usually in the presence of a base. In addition, steps 1-4
Can also be carried out according to the method described in US Pat. No. 5,990,315.

(Step 1-5) The reaction is carried out by reacting the compound represented by the formula [VI] in a solvent in the presence of an acid catalyst. Reaction temperature: room temperature to 120 ° C. Reaction time: Instant to 48 hours Acid catalyst: hydrochloric acid, sulfuric acid, boron trifluoride, etc. Amount of acid catalyst: catalytic amount to excess amount Solvent used: alcohols such as methanol, ethanol, isopropanol, etc. After the completion of the reaction with water, a mixture of these, water is added to the reaction mixture and the resulting crystals are collected by filtration, or water is added to the reaction mixture and the organic solvent is extracted and concentrated to perform an ordinary post-treatment operation. The desired compound can be obtained. The compound can also be purified by operations such as chromatography and recrystallization.

(Step 1-6) The reaction is carried out by reacting the compound represented by the formula [IX] with 3,4,5,6-tetrahydrophthalic anhydride. And are usually reacted in a solvent. Further, an acid catalyst (p-toluenesulfonic acid or the like) or an acid-base catalyst (p-toluenesulfonic acid and piperidine or the like) may be added. Reaction temperature: room temperature to 150 ° C. Reaction time: Instantaneous to 48 hours Amount of 3,4,5,6-tetrahydrophthalic anhydride used in the reaction: 0 with respect to 1 mol of the compound represented by the formula [IX] 0.5 mol to 2 mol ratio. Solvents used: Organic acids such as acetic acid and propionic acid, hydrocarbons such as hexane, heptane, toluene, xylene and cyclohexane, THF, 1,4-dioxane, diethoxyethane, di (2-methoxyethyl) ether, Ethers such as tri (ethylene glycol) dimethyl ether, nitrile compounds such as acetonitrile and propionitrile, halogen compounds such as chlorobenzene, and mixtures thereof. After the reaction is completed, water is added to the reaction mixture and the resulting crystals are filtered. The target compound can be obtained by collecting or performing usual post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent and concentrating. The compound can also be purified by operations such as chromatography and recrystallization.

[Production Method 2] From the compound [III] to the compound of the present invention [VII] according to the production route shown in the following scheme.
A method of manufacturing. [In the formula, X, Y, L ² , R ⁶ and R ⁵ have the same meanings as described above. ]

(Step 2-1) The reaction is carried out by reacting the compound represented by the formula [III] in a solvent in the presence of an acid catalyst. Reaction temperature: room temperature to 120 ° C. Reaction time: Instant to 48 hours Acid catalyst: hydrochloric acid, sulfuric acid, boron trifluoride, etc. Amount of acid catalyst: catalytic amount to excess amount Solvent used: alcohols such as methanol, ethanol, isopropanol, etc. After the completion of the reaction with water, a mixture of these, water is added to the reaction mixture and the resulting crystals are collected by filtration, or water is added to the reaction mixture and the organic solvent is extracted and concentrated to perform an ordinary post-treatment operation. The desired compound can be obtained. The compound can also be purified by operations such as chromatography and recrystallization.

(Step 2-2) The reaction is carried out by reacting the compound represented by the formula [XIV] with 3,4,5,6-tetrahydrophthalic anhydride in a solvent.
In addition, an acid catalyst (p-toluenesulfonic acid, etc.) or acid-
A base catalyst (p-toluenesulfonic acid, piperidine, etc.) may be added. Reaction temperature: room temperature to 150 ° C. Reaction time: Instantaneous to 48 hours Amount of 3,4,5,6-tetrahydrophthalic anhydride used in the reaction: 0 based on 1 mol of the compound represented by the formula [XIV] 0.5 mol to 2 mol ratio. Solvents used: Organic acids such as acetic acid and propionic acid, hydrocarbons such as hexane, heptane, toluene, xylene and cyclohexane, THF, 1,4-dioxane, diethoxyethane, di (2-methoxyethyl) ether, Ethers such as tri (ethylene glycol) dimethyl ether, nitrile compounds such as acetonitrile and propionitrile, halogen compounds such as chlorobenzene, and mixtures thereof. After the reaction is completed, water is added to the reaction mixture and the resulting crystals are filtered. The target compound can be obtained by collecting or performing usual post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent and concentrating. The compound can also be purified by operations such as chromatography and recrystallization.

(Step 2-3) The reaction is carried out by reacting the compound of the formula [XV] with iron powder in the presence of a protic acid in a solvent. Reaction temperature: Room temperature to 100 ° C. Reaction time: Instantaneous to 48 hours Protonic acid: Formic acid, acetic acid and other acids Amount: 2 to 1 mol of the compound represented by the formula [XV]
Molar to excess ratio. Amount of iron powder: relative to 1 mol of the compound represented by the formula [XV],
Ratio of 2 to 6 moles. Solvents used: Hydrocarbons such as hexane, heptane, toluene, xylene, cyclohexane, THF, 1,4
-Dioxane, diethyl ether, dibutyl ether,
Ethers such as diphenyl ether, dimethoxyethane, diethoxyethane, di (2-methoxyethyl) ether, tri (ethylene glycol) dimethyl ether, alcohols such as methanol, ethanol and isopropanol, organic acids such as formic acid, acetic acid and propionic acid, After completion of the reaction of esters such as dimethyl carbonate, diethyl carbonate, methyl acetate and ethyl acetate, water and a mixture thereof, water is added to the reaction mixture and the resulting crystals are collected by filtration, or water is added to the reaction mixture. In addition, ordinary post-treatment operations such as extraction with an organic solvent and concentration can be performed to obtain the target compound. The compound can also be purified by operations such as chromatography and recrystallization. The reaction can also be carried out according to the method described in "Reduction General", p159-266, 4th edition Experimental Chemistry Course 26 (Maruzen Co., Ltd.).

(Step 2-4) The reaction is carried out by reacting the compound represented by the formula [XVI] with the compound represented by the formula [V] in the presence of a base, usually in a solvent. Reaction temperature: room temperature to 120 ° C. Reaction time: Instant to 48 hours Base: organic base such as pyridine, picoline, lutidine, dimethylaminopyridine, triethylamine, etc. Amount of base: 1 mol of the compound represented by the formula [XVI], Ratio of 0.1 mol to 2 mol. Amount of the compound represented by the formula [V] to be subjected to the reaction: Formula [XV
I]] 0.5 mol to 2 mol with respect to 1 mol of the compound
Mole ratio. Solvents that may be used: acid amides such as DMF, N, N-dimethylacetamide, hydrocarbons such as hexane, heptane, toluene, xylene, cyclohexane, TH
F, 1,4-dioxane, diethoxyethane, di (2-
(Methoxyethyl) ether, ethers such as tri (ethylene glycol) dimethyl ether, acetonitrile, nitrile compounds such as propionitrile, halogen compounds such as chlorobenzene, and a mixture thereof After the reaction is completed, water is added to the reaction mixture, The resulting crystals can be collected by filtration or can be subjected to usual post-treatment operations such as adding water to the reaction mixture and extracting with an organic solvent and concentrating. The compound can also be purified by operations such as chromatography and recrystallization. Further, the compound represented by the formula [VII] is also produced by reacting the compound represented by the formula [XVI] with the compound represented by the formula [V-1] in the presence of a base, usually in a solvent. be able to. Moreover, steps 2-4 can also be performed according to the method described in US Pat. No. 5,990,315.

The phenol compound represented by the formula [I] is
According to the method described in JP-A-63-310855,
It can be manufactured.

The compound of the present invention has an excellent herbicidal effect,
Some also show excellent selectivity between crops and weeds. That is, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in foliage treatment and soil treatment of upland fields. Weeds of the family Acapulaceae: Oenothera
a erythrosepala), evening primrose (Oenothera biennis), evening primrose (Oenothera laciniata) Ranunculaceae weeds: Spodoptera frugiperda (Ranu)
nculus muricatus), wart buttercup (Ranunculus sardous) Polygonum weed: Polygonum con
volvulus), Sanaetade (Polygonum)
lapathifolium), American sandweed (Polygonum pensylvanicu)
m), Harutade (Polygonum persica)
ria), Japanese knotweed (Polygonum cuspi)
datum), willow (Polygonum av)
iculare), Rumex cress
ispus), Rumex obtu (Rumex obtu)
sifolius), Rumex ace (Rumex ace)
tosella) Purslane Weed: Purslane (Portulaca)
oleracea) Dianthus weed: Stellaria med
ia), the Netherlands Water Cerastium g.
lomeratum) Weeds of the family Chenopodiaceae: Shiroza (Chenopodium al)
Bum), Houkigi (Kochia scopari)
a) Amaranthaceae: Amaranthus r.
etroflexus), Long-tailed dragonfly (Ama)
ranthus hybridus), Amaranthus palmeri (Amaranthus palmeri),
Tallwater hemp (Amaranthus tu
berculatus), common water hemp (A
maranthus rudis Weed: Cruciferae: Wild radish (Raphan)
us raphanistrum), Peanut (S
inapis arvensis, Capsule (Caps)
ella bursa-pastoris, Lepidium virginicu
m) Leguminous weeds: S. paniculata (Sesbania)
exaltata), Ebisugusa (Cassia ob
tusifolia, Florida Beggarweed (De
smodium tortuosum, white clover (Trifolium repens), giant pea (Vicia sativa), rice sesame (Medicago lupulina) Weeds: poplar
s) Mallow family weeds: Abutilon theop
hrasti, American stag deer (Sida sp)
inosa), Ginseng (Hibiscus tri)
onum) Violet weed: Field pansy (Viola ar)
Vensis), wild pansies (Viola tr
Weeds of the Rubiaceae family: Galium apari
ne) Convolvulaceae weeds: American morning glory (Ipomoea)
hederacea), Malaba morning glory (Ipomoe)
a pururea), Malva american morning glory (I
pomoea hederacea var integ
riuscula, Yellow-faced morning glory (Ipomoea)
lacunosa), Convolvulus vulgaris (Convol)
vulus arvensis), Bindweed (C)
alystegia sepium) Lamiaceae weeds: Lamium pur
pureum), Hotokenoza (Lamium ampl)
exicaule) Solanaceous weed: White-billed morning glory (Dataur)
a stramonium), Japanese physalis (Sola)
num nigrum), warnabis (Solanum)
carolinense) Weed: Scutellaria baicalensis (Veroni)
ca persica), Tachiinoufuguri (Vero)
nica arvensis), Fraser grass (Ver)
onica hederaefolia Weed: Asteraceae (Xanthium strum)
Arium), wild sunflower (Helianthus)
annuus), chamomile (Matricaria c)
hammilla), dog chamomile (Matrica)
ria perforata or indora),
Mockingbird (Matricaria matricar)
ioides), corn marigold (Chrysa)
ntheum segetum), ragweed (Amb)
rosia artemisiifolia, Ambrosia trifida, Erigeron canadensi
s), mugwort (Artemisia princep)
s), Solidago alba (Solidago al)
tissima), goldenrod (Solidag)
o gigantea), dandelion (Tara)
xacum officinale)
enecio vulgaris), oyster bark (G
alinsogora cilita) Weeds of the family Musaceae: Forget-me-nots (Myosotis s)
corpioides), Noharamurasaki (Myoso)
tis arvensis) Weeds of the potato family: Asclepias
syriaca) Euphorbiaceae weeds: Euphorbi
a helioscopia), Hypericum perforatum (Eu)
phorbia maculata) Weeds of the family Furoaceae: American Furo (Geranium)
carolinianum) Oxalis c.
orymbosa) Cucurbitaceae weed: Areciuri (Sicyos angula)
tus) Gramineae weeds: Echinochloa cr
us-galli), Enocorogusa (Setaria)
viridis), Akinoe no Kologsa (Setari)
a Faberi), Digitaria s
anguinalis), Ohishiba (Eleusine)
indica), Poa annu (Poa annu)
a), Blackgrass (Alopecurus myo)
suroides), oats (Avena fat)
ua), silky bentgrass (Apera spic)
a-venti), Seiban Sorghum (Sorghum)
halpense), cedar (Agropyro)
n repens), Umanotahiki (Bromust)
ectorum), Cynodoned
actylon), giant millet (Panicum d)
ichotomiflorum), Texas Panicum (Panicum texanum), Shutter cane (Sorghum vulgare), Narcovie (E
riochloavillasa), Alopecurus geniculatus communis weeds: Commelina co
mmunis), Commelina
benghalensis Weed: Equisetum arve
nse) Cyperaceae weed: Cyperus cyperus (Cyperus)
iria), Chinese nutsedge (Cyperus rotund)
us), Yellow sedge (Cyperus esculen)
Moreover, some of the compounds of the present invention are corn (Z
ea mays), wheat (Triticum aest)
ivum), barley (Hordeum vulgar)
e), rye (Secale cereal), oats (Avena sativa), rice (Orys)
a sativa), sorghum (Sorghum bic)
color), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Bet)
a vulgaris), peanuts (Arachis)
hypogaea), sunflower (Helianthus)
annuus), rapeseed (Brassica napu)
s) and other major crops, flowers and horticultural crops such as vegetable and vegetable, do not show harmful chemical damage. Further, the compound of the present invention can effectively weed out various weeds that are problematic in non-tillage cultivation of soybean, corn, wheat and the like. Moreover, some of the compounds of the present invention do not show harmful phytotoxicity to crops.

Further, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in the flooding treatment of paddy fields. Gramineous weeds: Echinochloa o
lyzicola) Weeds of the genus Asteraceae: Adena (Lindernia p.
rocumbens, American Azena (Linder)
nia dubia var. major), Taketoazena (Lindernia dubia var. dub)
ia), Scutellaria baicalensis (Lindernia a)
nagallidea), red pepper (Linde)
rnia micrantha), Capsicum annuum (Lindernia antipoda) Weeds of the family Lythraceae: Riga indica (Rotala indi)
ca), Ambergrass (Ammannia multi)
Flora), Hisobahimeso Misohagi (Ammannia)
coccinea) Weeds of the family Mizochabe (Elatine tr)
iandra) Cyperaceae weed: Cyperus
difformis), firefly (Sirrpus j)
uncoides subsp. hotarui, Inu Firefly (Sirpus juncoides su
bsp. juncoides), Matsubai (Eleo)
charis acicularis), Cyperus serotonus, Eleocharis kuroguwai Weed mallow family: Monochoria v
aginalis) Weeds: Uritagawa (Sagittaria p)
ygmaea), Japanese sardine (Sagittaria t)
rifolia), Heramodeka (Alismacan)
aliculatum) Weeds of the family Amphiraceae: Potamogeto
n distinctus) Weeds of the Umbelliferae: Umbellifer (Oenthethe javanic)
a) Moreover, some of the compounds of the present invention do not show any harmful phytotoxicity to transplanted rice.

Further, the compound of the present invention can be used for industrial facilities such as levee slopes, riverbeds, shoulders and slopes of roads, railway floors, park greens, grounds, parking lots, airports, factories and storage facilities, and vacant land. Cultivated land, or non-cultivated land where it is necessary to control the growth of weeds such as unused land in the city, or
A wide range of weeds that occur in orchards, meadows, lawns, forests, etc. can be weeded. Further, the compound of the present invention is used in rivers, waterways,
Water hyacinth (Eichh) that occurs in canals, reservoirs, etc.
It has a herbicidal effect on aquatic weeds such as ornithia crassipes.

The compound of the present invention has properties similar to those of the herbicidal compound described in International Patent Application Publication No. WO95 / 34659, and the herbicide resistance gene and the like described therein are introduced. In the case of cultivating a crop to which the resistance to the herbicide is imparted, it is possible to use a larger amount of the compound of the present invention used in the cultivation of a normal crop to which the tolerance is not imparted, Other undesirable plants can be more effectively weeded.

When the compound of the present invention is used as an active ingredient of a herbicide, it is usually a solid carrier, a liquid carrier, a surfactant,
It is mixed with other auxiliaries for formulation to prepare emulsions, wettable powders, suspensions, granules, concentrated emulsions, wettable granules and the like.
In these formulations, the compound of the present invention as an active ingredient is contained in a weight ratio of 0.001 to 80%, preferably 0.005 to 7%.
Contains 0%. As the solid carrier, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, mineral fine powder such as calcite, organic fine powder such as walnut shell powder, water-soluble organic fine powder such as urea, Fine powders of inorganic salts such as ammonium sulfate and fine powders of synthetic hydrous silicon oxide can be mentioned.
Aromatic hydrocarbons such as alkylbenzenes such as methylnaphthalene, phenylxylylethane and xylene, alcohols such as isopropanol, ethylene glycol and 2-ethoxyethanol, esters such as dialkyl phthalates, acetone, cyclohexanone, isophorone, etc. Examples thereof include ketones, mineral oil such as machine oil, soybean oil, vegetable oil such as cottonseed oil, dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water and the like. Surfactants used for emulsification, dispersion, wet extension, etc. include alkyl sulfate ester salts, alkyl sulfonates, alkylaryl sulfonates, dialkylsulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and the like. . Other auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol,
Examples include gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like.

The compound of the present invention is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or after emergence of weeds. Soil treatment includes soil surface treatment, soil admixture treatment, etc., and foliage treatment includes treatment from above the plant,
There is a local treatment that treats only weeds so that they do not adhere to crops. In addition, the herbicidal effect may be enhanced by mixing with other herbicides. further,
It is also possible to mix or use together with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners and the like. Examples of such herbicides are shown below. Atrazine, cyanadine (cya)
nazine), dimetamethrin
trin), metribuzin,
Promethrin, Simazine (si
mazine), cimetrin, chlorotolururon, diuron, fluometuron.
uron), isoproturon (isoproturo)
n), linuron, metabenzziazuron, propanil, bentazone (bent)
azone), bromoxynil (bromoxyni)
l), ioxynil, pyridate butamifos, dithiopyr (d)
ithiopyr), ethalfluralin (ethalf)
luralin, pendimethalin
thalin), thiazopyr,
Trifluralin, acetochlor, alachlor
achlor), butachlor (butachlo)
r), dietatylethyl (diethyl-eth)
yl), dimethenamide
d), fluthiamide, mefenacet, metolachlor, pretilachlor (pr)
etilachlor), propachlor (propa)
chlor), symmethylin
n) Acifluorfen, acifluorfen Na salt (acifluorfen-so)
dium), benzfendizone (benzfendi)
zone), bifenox, butafenacil, chlomethoxynil, fomesafen, lactofen.
fen), oxadiazon, oxadialygyl, oxyfluorfen, carfentrazone-ethyl (carfentrazone-ethy)
l), fluazolate, flumicrolac-pentyl
ntyl), flumioxazine (flumioxazi)
ne), fluthiaset methyl
-Methyl), isopropazole (isoprop)
azol, sulfentrazone (sulfentra)
zone), thiadimine
n), azaphenidin, pyraflufen-ethyl
l), cinidon-ethyl diphenzoquat, diquat, paraquat
t) 2,4-D, 2,4-DB, clopyralid (clopy)
Ralid), dicamba, fluroxypyr, MCPA, MCP
B, mecoprop, quinclorac, triclopyr (tric)
lopyr) azimsulfuron, bensulfuron-meth
yl), chlorimuron ethyl
-Ethyl), chlorsulfuron
furon), chloransrum methyl
ulam-methyl), cyclosulfamurone (c
yclosulfamuron), jikurosurumu (di
Closulam), ethoxysulfuron (ethox)
ysulfuron), flazasulfuron (flaza)
sulfuron), flucarbazone (flucarb)
azone), flumetsula
m), flupyrsulfuron
on), halosulfuron methyl (halosulfur)
on-methyl), imazosulfuron (imazo)
sulfuron), iodosulfuron (iodos)
ulfuron), metsula
m), metsulfuron-
methyl), nicosulfuron
ron), oxasulfuron (oxasulfuro)
n), primisulfuron methyl (primisulfu)
ron-methyl), procarbazone Na salt (pr
ocarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl
l), sulfosulfuron
n), triasulfuron
n), tribenuron-methyl (tribenuron-
methyl), tritosulfuron (tritosul)
furon), thifensulfuron-methyl
nsulfuron-methyl), triflusulfuron-meth
yl), pyribenzoxime
m), bispyribac Na salt (bispyribac-
Sodium), Pyriminoback methyl (pyrimi)
nobac-methyl), pyrithiobac Na salt (pyrithiobac-sodium), imazameth, imazametabenz-methyl, imazamox, imazapic (i).
mazapic), imazapyr,
Imazaquin, imazethapyr (i
Mazethapyr) Tepraloxydim, aloxidim Na salt (aloxidim-sodiu)
m), clethodim, clodinahop propargyl (clodinafop-prop)
argyl), cyhalofop-butyl (cyhalofo)
p-butyl), diclofop-methyl (diclof)
op-methyl), phenoxaprop-ethyl, fenoxaprop-p-et.
hyl), fluazifop-butyl (fluazifop)
-Butyl), fluazifop-p-butyl (fl
uazifop-p-butyl), haloxyfop-methyl, quizalofop-p-eth.
yl), setoxydim, tralkoxydim, diflufenican, flurtamon, norflurazone, benzophenap (b).
enzofenap), isoxaflutole (isox)
aflutole), pyrazolate (pyrazola)
te), pyrazoxifene
n), sarcotrione, clomazone, mesotrione (me)
sotrione), isoxachlortole (isox)
achlortole) bialaphos, glufosinate ammonium salt (glufosinate-ammo)
nium), glyphosate (glyphosat)
e), sulphosate, dichlobenil, isoxaben, benthicarbo
carb, butyrate, dimepiperate, EPTC,
Esprocarb, molinate, pyribucur
ticarb), triallate
Diflufenzopyr bromobutide, DSMA,
MSMA, cafenstrol
l), daimuron, epoprodan, flupoxum
am), metobenzuron
n), pentoxazone, piperophos, triaziflam beflubutamide, benzobycyclone benzofluram (f), fentraflufenaf, clomeprozamide, clomeprozamide, clomeprozamide, clomepropz, clomepropa, clomepropz, phenometa, benzobycyclone, belombuturam, phenometa. flora
sulam), indanofa
n), isoxadifen, mesotrione, naproanilide, oxaziclomefone, pesoxyamide, phenothiamide.
nothiol), pyridafo (pyridafo)
l) The above compounds are available from Farm Chemicals Handbook (Meister Publishing Company) [Farm Chem
ical Handbook (Meister Publ
ISHING COMPANY)] 1995 edition catalog, Agchem New Compound Review 1995
Edition (Agchem Information Service) [AG C
HEM NEW COMPOUND REVIEW, VO
L. 13, 1995 (AG CHEM INFORMA
Tion Service)], Agchem New Compound Review 1997 Edition (Agchem Information Service) [AG CHEM NEW COMPOUN
D REVIEW, VOL. 15, 1997 (AG CH
EM INFORMATION SERVICE)], Agchem New Compound Review 1998 Edition (Agchem Information Service) [AG CHEM NE
W COMPOUND REVIEW, VOL. 16, 1
998 (AG CHEM INFORMATION SE
RVICE)], Agrow No. 296 page 22 (AG
ROW No. 296 p22), Agrow No. 297
21 (AGROW No. 297 p21), Agrow No. 308, p. 22 (AGROW No. 308 p.
22), Agrow No. 324, pages 26-27 (AGR
OW No. 324 pp26-27) or "Herbicides Research Guide (Hakuyusha)". When the compound of the present invention is used as an active ingredient of a herbicide, the treatment amount is
Weather conditions, formulation form, treatment time, treatment method, soil condition,
Depending on the target crop and target weed, it is usually 0.01 g to 20000 g per hectare, preferably 1 g
-12000 g, and emulsions, wettable powders, suspensions, concentrated emulsions, granular wettable powders, etc. usually have a predetermined amount of 10 liters to 1000 liters per hectare (adjuvants such as spreading agents if necessary). The granules and some suspensions are usually treated as they are without any dilution. As the auxiliary agent used here as needed, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate, abietic acid salt, dinaphthylmethane disulfonate, crop oil concentrate ( crop oil conc
and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil. In addition, the compound of the present invention is a defoliant / drying agent for cotton, and potato (Solanu).
It can be used as an active ingredient of a harvesting aid such as a drying agent for mtuberosum). In that case, the compound of the present invention is usually formulated as in the case of being used as an active ingredient of a herbicide, and foliar treatment is carried out before harvesting a crop, alone or in combination with another harvesting aid.

[0025]

EXAMPLES The present invention will be described in more detail with reference to production examples, but the present invention is not limited to these examples.
The compound numbers given to the compounds of the present invention are the numbers described in Table 1 below. First, production examples of the compound of the present invention will be shown. Production Example 1 [Production of Inventive Compound 1] First Step 5-Amino-2-chloro-4-fluorophenol 16
To a solution of g in 80 ml of acetic acid, 10.2 g of acetic anhydride was added dropwise under ice cooling. After stirring at room temperature for 1 hour, the reaction mixture was poured into water, and the generated crystals were collected by filtration. The crystals were washed with hexane and methyl t-butyl ether to give N-
19 g of (4-chloro-2-fluoro-5-hydroxyphenyl) acetamide was obtained. ¹ H-NMR (300 MHz, CD ₃ SOCD ₃ , TMS
δ (ppm): 2.07 (3H, s), 7.31 (1
H, d, J = 10.6 Hz), 7.73 (1H, d, J
= 7.4 Hz), 9.69 (1H, br), 10.14
(1H, br)

Second step 10 g of N- (4-chloro-2-fluoro-5-hydroxyphenyl) acetamide and 8.3 g of 2-fluoronitrobenzene were dissolved in 40 ml of DMF. 8.1 g of potassium carbonate was added to this solution, and the mixture was stirred at room temperature for 1 day. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (developing solvent; hexane: ethyl acetate = 1: 1), and the obtained crystals were washed with n-hexane, and then N- [4-chloro There were obtained 13.7 g of 2-fluoro-5- (2-nitrophenoxy) phenyl] acetamide. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (p
pm)): 2.18 to 2.21 (3H, m), 6.85
~ 6.90 (1H, dd, J = 1.3Hz, 5.0H
z), 7.01 to 7.30 (2H, m), 7.45 to
7.54 (1H, m), 7.98 (1H, dd, d =
1.9 Hz, 4.9 Hz), 8.17 (1H, br),
8.19 (1H, d, J = 8.8Hz) Melting point: 117.2 ° C

Third Step 10 g of N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] acetamide was added to 100 ml of a solution of boron trifluoride-methanol complex in methanol, and the mixture was refluxed for 4 hours. Heated and stirred. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue is subjected to silica gel column chromatography (developing solvent; hexane:
Ethyl acetate = 3: 1), 4-chloro-2-fluoro-5- (2-nitrophenoxy) aniline 10.1 g
Got ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (p
pm)): 3.85 (2H, br), 6.55 (1H,
d, J = 8.4 Hz), 6.83 (1H, d, J = 8.
7 Hz), 7.08 to 7.20 (2H, m), 7.44
~ 7.51 (1H, m), 7.95 (1H, dd, J =
1.5Hz, 8.1Hz)

Step 4 9 g of 4-chloro-2-fluoro-5- (2-nitrophenoxy) aniline and 5.2 g of 3,4,5,6-tetrahydrophthalic anhydride were added to 100 ml of acetic acid under reflux conditions. The mixture was heated and stirred for 8 hours. In addition, 3, 4
5.0 g of 5,6-tetrahydrophthalic anhydride was added, and the mixture was heated and stirred under reflux conditions for 4 hours. The reaction mixture was concentrated under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated. The resulting crystals were washed with hexane and methyl t-butyl ether to give N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] -3,
8.6 g of 4,5,6-tetrahydrophthalimide was obtained. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (p
pm)): 1.75 to 1.88 (4H, m), 2.38
~ 2.48 (4H, m), 6.94 (1H, dd, J =
1.1 Hz, 8.5 Hz), 7.03 (1H, d, J =
6.7 Hz), 7.20 to 7.27 (1 H, m), 7.
40 (1H, d, J = 8.7 Hz), 7.49 to 7.5
6 (1H, m), 7.98 (1H, dd, J = 1.4H
z, 8.2 Hz)

Step 5: A solution of 100 ml of acetic acid, 100 ml of water and 4.6 g of iron powder was added at 90 ° C. to N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] -3,4. ，
A solution of 8.6 g of 5,6-tetrahydrophthalimide in 100 ml of ethyl acetate was added dropwise. After stirring at 90 ° C. for 1 hour, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The resulting crystals were washed with hexane and methyl t-butyl ether to give N- [4-chloro-2-fluoro-5-
(2-Aminophenoxy) phenyl] -3,4,5,6
-6.4 g of tetrahydrophthalimide are obtained. Melting point: 266.3 ° C

Step 6 N- [4-chloro-2-fluoro-5- (2-aminophenoxy) phenyl] -3,4,5,6-tetrahydrophthalimide (1.0 g) and methanesulfonic acid chloride (0.1 g).
To a solution of 33 g and 20 ml of toluene was added dropwise 0.2 g of pyridine at 80 ° C. After heating and stirring under reflux conditions for 4 hours, the mixture was left at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent; hexane: ethyl acetate = 3: 1) to give N- [2- (2-chloro-4-fluoro-5-5.
0.63 g of (3,4,5,6-tetrahydrophthalimido-1-yl) phenoxy) phenyl] methanesulfonamide [invention compound 1] was obtained. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (p
pm)): 1.77-1.86 (4H, m), 2.36
~ 2.45 (4H, m), 3.04 (3H, s), 6.
79 (1H, dd, J = 2.1Hz, 7.5Hz),
6.89 (1H, br), 6.97 (1H, d, J =
6.4 Hz), 7.10 to 7.15 (2H, m), 7.
40 (1H, d, J = 9.1 Hz), 7.66 (1H,
dd, J = 2.1 Hz, 7.5 Hz)

Production Example 2 [Production of Compound 1 of the Present Invention] First Step 26 g of N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] acetamide was dissolved in 150 ml of ethyl acetate to obtain a catalytic amount. After adding 10% Pd / carbon, the reaction was carried out at room temperature for 3 hours in a hydrogen atmosphere. After the reaction was completed, the reaction mixture was filtered through Celite and concentrated under reduced pressure. The generated crystals were washed with n-hexane to obtain 24 g of N- [4-chloro-2-fluoro-5- (2-aminophenoxy) phenyl] acetamide. ¹ H-NMR (300 MHz, CDCl ₃ , TMSδ (p
pm)): 2.14 (3H, s), 3.80-4.15.
(2H, br), 6.66 to 6.99 (4H, m),
7.20 (1H, d, J = 10.3Hz), 7.36
(1H, br), 8.02 (1H, d, J = 7.4H
z)

Step 2 N- [4-chloro-2-fluoro-5- (2-aminophenoxy) phenyl] acetamide (1 equivalent) and pyridine (1)
1 equivalent of methanesulfonic acid chloride is added dropwise at 80 ° C. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography, and N- [4-chloro-2-fluoro-5 was used.
-(2-Methanesulfonylaminophenoxy) phenyl] acetamide is obtained.

Third Step N- [4-chloro-2-fluoro-5- (2-methanesulfonylaminophenoxy) phenyl] acetamide was added to a solution of boron trifluoride-methanol complex in methanol, and the mixture was heated and stirred under reflux conditions. To do. After completion of the reaction, the reaction mixture is concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution is added, and the mixture is extracted with ethyl acetate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and N-
[2- (5-Amino-2-chloro-4-fluorophenoxy) phenyl] methanesulfonamide is obtained.

Step 4 N- [2- (5-amino-2-chloro-4-fluorophenoxy) phenyl] methanesulfonamide (1 equivalent) and 3,4,5,6-tetrahydrophthalic anhydride (1 equivalent) were added. In addition to acetic acid, heat and stir under reflux conditions. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to give N- [2- (2-chloro-4-fluoro-5- (3,4,5,6-tetrahydro Phthalimido-1-yl) phenoxy) phenyl]
Obtain methanesulfonamide.

Production Example 3 [Production of N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] acetamide] N- (4-chloro-2-fluoro-5-hydroxyphenyl) acetamide 10 g And 2-chloronitrobenzene (10 g) are dissolved in DMF (100 ml), potassium carbonate (7.4 g) is added to the solution, and the mixture is stirred at room temperature for 2 hours.
The mixture was heated and stirred at 4 ° C for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography (developing solvent; hexane: ethyl acetate = 1: 1),
5.1 g of N- [4-chloro-2-fluoro-5- (2-nitrophenoxy) phenyl] acetamide was obtained.

Next, formulation examples are shown. The compounds of the present invention are shown by the compound numbers in Table 1 below. Parts represent parts by weight. Formulation Example 1 50 parts of each of the compounds 1 to 25 of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. Formulation Example 2 10 parts of each of the compounds 1 to 25 of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of cyclohexanone are mixed well to obtain each emulsion. Formulation Example 3 2 parts each of compounds 1 to 25 of the present invention, synthetic hydrous silicon oxide 2
Parts, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 64 parts of kaolin clay are well pulverized and mixed,
After adding water and kneading well, it is granulated and dried to obtain each granule. Formulation Example 4 25 parts of each of the compounds 1 to 25 of the present invention, 50 parts of a 10% aqueous solution of polyvinyl alcohol, and 25 parts of water are mixed, and wet pulverized until the average particle diameter becomes 5 μm or less to prepare each suspension agent. obtain.

Formulation Example 5 To 40 parts of a 10% aqueous solution of polyvinyl alcohol, 5 parts of each of the compounds 1 to 25 of the present invention were added, and the mixture was emulsified and dispersed by a homogenizer until the average particle size became 10 μm or less, and then 55 parts. Water is added to obtain a thick emulsion of each.

Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of a herbicide. Test Example 1 [Field and foliage treatment test] Soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and seeds of barnyard grass, blackgrass, and morning glory were sown and grown in a greenhouse for 10 days. Thereafter, the compound 1 of the present invention was made into an emulsion according to Formulation Example 2, a predetermined amount thereof was diluted with water containing 1000 liters of spreading agent per hectare, and the whole foliage was treated uniformly from above the plant with a sprayer. did. After the treatment, the plants were grown in a greenhouse for 3 days and the herbicidal efficacy was investigated. As a result, the compound 1 of the present invention completely suppressed the growth of barnyard grass, blackgrass, and morning glory at a dose of 500 g / ha.

Next, examples of the compounds of the present invention are shown in the table below together with the compound numbers, but the compounds of the present invention are not limited to these examples. The formula below Compound shown by

[Table 1]

[0040]

By using the compound of the present invention, an excellent herbicidal effect can be obtained.

─────────────────────────────────────────────────── ─── Continued Front Page (51) Int.Cl. ⁷ Identification Code FI Theme Coat (Reference) C07C 311/09 C07D 209/48 Z

Claims (7)

[Claims] 1. A formula [VII] [In the formula, X represents a halogen atom, Y represents a halogen atom, and R ⁵ represents a C1-C3 alkyl group or a C1-C3 haloalkyl group. ] The tetrahydrophthalimide compound shown by these. 2. In the formula [VII], X is a fluorine atom, Y
Is a chlorine atom, and R ⁵ is a C1-C3 alkyl group, The tetrahydrophthalimide compound according to claim 1. 3. A formula [XVI] [In the formula, X represents a halogen atom and Y represents a halogen atom. ] Or expression [XV] [In the formula, X and Y have the same meanings as described above. ] The tetrahydrophthalimide compound shown by these. 4. Formula [IX] [In the formula, X represents a halogen atom, Y represents a halogen atom, and R ⁵ represents a C1-C3 alkyl group or a C1-C3 haloalkyl group. ] Or the formula [XIV] [In the formula, X and Y have the same meanings as described above. ] The diphenyl ether compound shown by these. 5. The formula [VI] [In the formula, X represents a halogen atom, Y represents a halogen atom, R ⁵ represents a C1-C3 alkyl group or a C1-C3 haloalkyl group, R ⁶ represents a C1-C6 alkyl group, C
It represents a 1-C6 alkoxy group or a phenoxy group. ],
Formula [IV] [In the formula, X, Y and R ⁶ have the same meanings as described above. ]
Or formula [III] [In the formula, X, Y and R ⁶ have the same meanings as described above. ]
A diphenyl ether compound represented by. 6. The diphenyl ether compound according to claim 5, wherein in the formulas [III], [IV] and [VI], R ⁶ is a methyl group. 7. A herbicide containing the tetrahydrophthalimide compound according to claim 1 or 2 as an active ingredient.