JPS608263A - Tetrahydroindole derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:2-Oxo-2,4,5,6-tetrahydroindole derivative of formula I (R1 is H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, 3-7c cycloalkyl, 1-4C halogenoalkyl, 2-4C halogenoalkenyl, 3-7C halogenocycloalkyl, benzyl, benzoyl, etc.; R2 is H, 1-4C alkyl, etc.). EXAMPLE:1-(1-Isopropyl-2-oxo-2,4,5,6-tetrahydroindol-3-yl)-3-methylurea. USE:Herbicide having excellent herbicidal activity against a wide variety of weeds, and especially effective when applied to the surface of the soil or water immediately before or after the sprouting of the weeds or applied directly to the surface of the leaf and stalk of the plant. PREPARATION:The compound of formula I can be prepared by reacting the compound of formula Cl-R1 or R1-NCO, etc. with the compound of formula II in an inert solvent or in the absence of solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R1 is a hydrogen atom, a C1-4 alkyl group, a C alkenyl group, a C2-4 alkynyl group, a C3-7 C-4 chloroalkyl group, a C1- 4) 10 canalkyl group, C
Represents a halokenyl alkenyl group, a C3-7 halogonic-40 alkyl group, a be/zyl group, a substituted benzyl group, a benzoyl group, a substituted benzoyl group, a C1-4 alkyl group having a heterocyclic group, or 2-oxy-2. The present invention relates to a 4,5,6-titrahydroindole derivative and a herbicide containing the compound as an active ingredient.

The compound of the present invention is prepared by adding a compound represented by CL-R1 or R1-NC0 to a suitable inert solvent, such as ethers such as tetrahydrofuran, dioxane, diisozolobyl ether, aromatic carbonization such as benzene, toluene, xylene, etc. Hydrogens, carbonated hydrocarbons such as carbon tetrachloride, chloroform, and ethylene dichloride, amines represented by 2 dissolved or suspended in acetonitrile, dimethylformamide, dimethyl sulfoxide, and sulfolane, or without a solvent. can be synthesized by reacting.

Typical synthesis methods for the compounds of the present invention will be shown below and explained in more detail, but as stated above, the methods are not limited in any way.

Synthesis example 1) 1-(1-isozorobyl-2-oxy-2.4.'
5.6-titrahydroindo-3-yl)-3-
Methylurea 3-amino-1-isopropyl-2-oxy-2.4,
5.6-Titrahydroindole 14.9 is dissolved in 50 ml of anhydrous Hensen and a few drops of triethylamine are added to catalyze. Methyl incyanate 5I is slowly added dropwise. After completion of the dropwise addition, the mixture was stirred at 30 to 40°C for 5 hours. After the reaction is completed, the precipitated crude crystals are filtered off and recrystallized from ether.

2) 1-(1-inpropyl-2-ogine-2.4,5
．． 6-titrahydroindol-3-yl) -3,
3-methylurea 3-amino-1-isopropyl-2-oxy-2.4,
14.9 g of 5.6-titrahydroindole and 9 g of triethylamine were dissolved in 50 ml of anhydrous benzene, and 9 g of dimethylcarbamoyl chloride and H were added.

After addition, stir at 30-40°C for 20 hours. After the reaction is completed, wash with 1T hydrochloric acid and water, and then remove the organic layer with sulfuric acid)
The crude crystals obtained by distilling off the solvent are recrystallized from ether.

Among the compounds of the present invention represented by the above general formula synthesized by a similar method, typical examples are summarized as shown in Table 1.

The compound of general formula 1 exhibits strong herbicidal activity against weeds,
Just before the weeds germinate or at the cutting stage of their growth,
When this active ingredient is applied 92 to 20 times per hectare, a wide range of weeds as described below can be killed in about 1 to 2 weeks.

By limiting the amount of Ushidamoto compound applied or by applying an appropriate application method, it can be used to control specific crops such as rice, corn, potatoes, sugarcane, peanuts, soybeans, sunflowers, barley, wheat, gum, cotton, and fruit trees. Weeds can be selectively controlled in cultivated fields.

The active compounds according to the invention can be formulated into dosage forms such as emulsions, wettable powders, pastes, flowable powders, powders, etc. by applying conventional formulation methods.

Furthermore, the compounds of the present invention can be mixed with other herbicides. In order to expand the range of herbicides, they can be used in combination with agricultural chemicals other than herbicides, such as insecticides and fungicides.

Next, examples of typical dosage forms will be given. "Department" in the description
indicates parts by weight.

Example 1 50 parts of the compounds shown in Table 1 as active ingredients for a wettable powder, 10 parts of diatomaceous earth, 35 parts of clay, 3 parts of sodium polyoxyethylene alkyl allyl ether sulfonate, and 2 parts of alkylnaphthalene sulfonic acid sorter were mixed. It is crushed to obtain a wettable powder containing 50% of the active ingredient compound.

When using, dilute with water to the specified concentration and spray.

Example 2 Granules 10 parts of the compound shown in Table 1, 20 parts of bentonite, 68 parts of clay
1 part and 2 parts of sodium dodecylbenzenesulfonate are mixed together, about 20 parts of water is added, and the mixture is kneaded with a mixer, then granulated through a granulator, and then dried and sized to produce granules containing 10 parts of the active ingredient. get the agent.

Example 3 Fifty of the compounds shown in Table 1 as emulsion active ingredients, 45 parts of toluene, and 5 parts of polyoxy 5-ethylene alkyl allyl ether were mixed to form a homogeneous solution, and the active ingredient
γ. Samurai 6. I; I; day (1) 1 (η゛ door rT Jaku 0 u tit 2 yote ゛ 搗 sung;
Eshi'ti exists I7'3゜Novel 2-oxo- of general formula 1
Since 2,4,5,6-titrahydroindole derivatives have excellent herbicidal activity, they are suitable for controlling weeds growing in paddy fields, orchards, etc. When this active compound is applied to the soil surface or treated during flooding, it is possible to significantly inhibit the growth of weeds and cause them to die.

Weeds can also be controlled by spraying a water solution on the stems and leaves of weeds that are slowly growing.

The dosage of this compound is regulated and the application amount is 92% per hectare.
When the amount is selected to be 20 kg, it can be used as a selective herbicide in fields where rice, corn, wheat, barley, sugar cane, soybeans, peanuts, sunflowers, wild yam, cotton, or fruit trees are cultivated.

The compounds of the present invention can be used, for example, to control the following weeds: That is, broad-leaved weeds, such as chickweed (Stellaria media), Ch.
enopodium) N Sagima
japonica), Chonopodiu
rn ficifolium), Japanese knotweed (Pol
ygonum nodosum), purslane (Por
tulace oleracea), shepherd's purse (Caps
ellabursa pastoris), Lepidium virginicum, Porippa 1ndica'.

Cardamine Hexuosa
, Avicennae (Abutilon avicennae)
, Sida 5pinosa
, Ipomoeapurpurea
Senecio vulgaris
), Sonchus asper, Bidens frondosa
, Ambrosia artemisiaef
olja), Aster 5ubulat
Lamium am plexic
avle), oxalis (Oxalis cornico)
late) ) Amaranthusret
rof 1exus), Crow Tree Pea (Vicia
satjva), Yaemgla (Galium spu)
rium), Solanum nigr
um), Datura stra
monium'), Konagi (Monochoriava)
Poaceae plants such as p'oa annua, Alopeculus aecualis, Digitaria adsendens, Eleusine 1ndica, and Eleusine annua. 5etaria viridis), dogfish (Echinochlor crus-galli)
, Agropyron tsukushi
ensjs), Lo liumperen
ne), Bromus cathartic
os), oat (Avena tatus), polypogon Higegaweri (Polypogon Higegaweri),
Panicum dichotom, Cyperus weeds such as Cyperus m1croiria, Cyperus 1ria, E.
leocbarisacicu Jaria)% 〇The compound of the present invention has excellent herbicidal efficacy against a wide range of weeds such as those mentioned above, and is especially effective when applied to the surface of fields, flooded areas, or in the period just before or after weeds germinate. Extremely high pesticidal effects can be obtained when sprayed on the foliage and foliage of plants.

Even when the compound of the present invention is mixed into soil, an extremely excellent weed control effect can be obtained.

In order to demonstrate the herbicidal effect of the herbicide according to the present invention, some representative test examples will be given and explained in more detail.

Test Example 1 Pre-emergence soil treatment (pre-emergence 5oi
Weeding effect on plants when using volcanic ash soil in pots with an area of 100 cm, and
Golden millet (Echinochloa crus-gal)
li), Polygonum nodo
sum), Amaranthus retro
flexus) ) corn (Xea mays)
Seeds of , wheat (Triticum aestivum), and japonica (Phaseo 1usradiatus) were sown and covered with soil to a thickness of about 5 mm, and immediately after that, the compounds listed in Table 1 were prepared into a wettable powder according to Example 1. ,
Dilute this with water to obtain 1 hectare of active ingredient iplO.
A dose corresponding to kg was administered to the soil surface of each pot.

The herbicidal effect on plants was investigated two weeks after treatment. The herbicidal effect was visually observed and expressed in Table 2 using a 6-level index from O: no effect to 5: complete death.

Test Example 2 Foliar contact treatment i (Foliar 5play trea
tment) Herbicidal effect on plants when L Fill pots with a surface area of 100 cm2 with volcanic ash soil, and incubate Digitaria sanguinalis.
Golden millet (Echinochloa crus-gal)
li), Polygonum no.
dosum), Aobi-i- (Amaranthus
retro-flexus) ,) corn (Zea)
mays), wheat (Triticum aestj)
Vum), Yae Buli (Phaseolus)
radiatus), cover it with about 1 kg of soil and place it in a greenhouse, and when the weeds have 1 to 2 leaves, apply a hydrating agent of the compound of the present invention per hectare, equivalent to 1 kg of soil. The mixture was diluted with water at an amount equivalent to 1.000 A/ha and sprayed using a sprayer. The results were investigated using the same criteria as in Test Example 1 after 10 days of chemical spraying, and the results were expressed using a 6-level index.

The test results are as shown in Table 3. - Test Example 3 Test of herbicidal effect on paddy weeds and chemical damage to paddy rice A pot with a surface area of 120 m2 was filled with paddy soil.
The seeds of Chigochoa crus-galli and Monochoria vaginalis were mixed into the soil with a surface layer of about 2 CrIL.
(ocharis acicularis) and two-leaf stage rice weeds were transplanted to two locations each, and the water depth was approximately 3 CII.
Keep it at L. Three days later, a hydrating powder containing the compound of the present invention prepared according to Example 1 was administered into the water at a dosage equivalent to 10 kg per hectare.

Three weeks after chemical treatment, the herbicidal effect and chemical damage to paddy rice were investigated. The herbicidal effect and the chemical damage to crops were determined by Test Example 1.
The survey was conducted using the same criteria as the above, and was expressed using a 6-level index. The test results are shown in Table 4.

Claims (1)

[Scope of Claims] 1) General formula [wherein R1 is a hydrogen atom, C1-4 alkyl C alkenyl group, C2-4 alkynyl-4 cycloalkyl group, C1-4)\location alkyl group,
C1 having a C-location alkenyl group, c,7-\location-40 alkyl group, be/zyl group, substituted pentyl group, benzoyl group, substituted benzoyl group, heterocyclic group -4 alkyl C alkyl group, R4, R5 are hydrogen or C1-4 alkyl
4-kyl group, and R2 represents hydrogen or a C1-4 alkyl group]. 2) General formula [wherein R1 is a hydrogen atom, a Cf-4 alkyl group, a C alkenyl &. , C2=furkynyl group, C3-7-4 cycloalkyl group, C1-4 halodaneargyl group, C
Indicates a halokenealkenyl group, a C6-7 halokenecyclo-40 alkyl group, a benyl group, a substituted benyl group, a benzoyl group, a substituted benzoyl group, and a C,-4 argyl group having a heterocyclic group. or 2-oxo-2,4,5,6-tetrahydro- A herbicide containing an indole derivative as an active ingredient.