JPS6011478A - Oxadiazolinon derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A 1,3,4-oxadiazolin-5-one derivative shown by the formula I (R1 is H, or CH3; R2 is H, or CH3; X and Y are Cl, or CH3; Z is CN, COOCH3, COOC2H5, phenyl, chlorophenyl, or tolyl). EXAMPLE:4-Benzyl-2(2,4-dichlorophenoxy)methyl-1,3,4-oxadiazolin-5-one. USE:A herbicide. PREPARATION:A compound shown by the formula II is reacted with a compound shown by the formula III in a solvent such as benzene, THF, DMF, etc. in the presence of a base such as a tertiary amine, etc. at room temperature - reflux temperature of the solvent, to give a compound shown by the formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a 1,3,4-oxadiazolin-5-A-one derivative represented by the following general formula and a herbicide containing the compound as an active ingredient.

General formula (where R1 is 1", or Cl-13; R2 is 1-1, or Cl-13:X, Y is C, or Icl-13:Z
accepts CN, C00CH3, COOG2H5, )1-nyl, chlorophenyl, or tolyl. ) 1, 3, 4. represented by the above general formula of the present invention. -Oxadiazolin-5-one derivatives are new compounds that have not been described in literature, patents, etc., and as a result of their synthesis and various studies, it has been found that they have excellent effects as herbicides.

In other words, Kibenmei's compound exhibits strong herbicidal activity against a wide range of weeds, and if 2 to 20 kg of the wood active ingredient is applied per hectare just before the weeds germinate or in the early stages of their growth, approximately 1. ~After 2 weeks,
Multiple rows of J and Una can kill a wide range of weeds.

In addition, it is possible to limit the application of this compound (1) or apply an appropriate application method to 1-1. Nagi-1 grass can be selectively controlled in fields where specific crops such as grass are cultivated.

Typical examples of the compounds of the present invention are as follows:
Examples include those shown in Table 1.

Incidentally, the compound is indicated by the symbol () in the above general formula.

Further, in the physical properties column, NMR indicates nuclear magnetic resonance spectrum, solvent nip in parentheses indicates fusion Jj+'+, 11] indicates refractive index, and the display method follows a conventional method.

(Blank below) Table 1 The compound of the present invention can be synthesized, for example, according to the following formula.

J, ); i to i, : pyridine, tertiary amines such as triearthylamine, potassium carbonate, thorium carbonate, etc., or thorium hydride.

Solvents: Inert ↑ such as bempine, 1-luconine, chloroform, dichloromethane, dioxane, ■] delether, te-1-rahydrofuran, ace-1-one, methylethyl-keyne, dimethylformamide, dimethyl sulfoxide, ace-1-nitrile 4r, etc. It dissolves A1, or a tertiary amine used as a base.

Reaction preparations: From room temperature to 1 Aif of solvent.

Typical synthesis examples are shown below and will be explained in more detail.

Synthesis example 2-(2,/l-diq[1[1)1-no4-cy)meso-1.3.4-Δquizadiazolinone-5-Δn 2.6 g, hensyl bromide 1 .7<1, t3 Q
l Potassium 1,4! 1 in acetonyl
Heat to reflux for 0 hours.

After cooling, insoluble matters are removed and the solvent is distilled off with the light turned off.

Dichloromethane and ice are added to the residue, and the IlIJ layer is separated and washed with water. Calcium chloride (after drying, the solvent is distilled off to obtain crude crystals. The crude crystals are recrystallized in a ben-U-hexane system to obtain 2.9 g of the target compound N07.

(2> 4-(3,4--JikIi +] Behenru)-
2,-[1-(2,4-jik [1 day) Jノ1-shi>'5
1]-1.3.4-J Kyridiazolin-5-one 2-
[1-(2,4-shik I'l rofeno↑shi)■pull]
-1,3,11-71 Gizadiasoline-5-'A2,
To a suspension of 10 me dimethylformamide containing 0.24 g of helium, add water-cooled C' little by little while stirring. After addition, return to room temperature and 3,4-
Add 1 Ride dropwise to Bensilk. After addition,
Stirring was continued at room temperature for 4 hours, and the reaction solution was poured into ice water, and crystals were deposited and covered. Dissipate the coarse crystals, add water and 10% carbonic acid.
- Rinse with an aqueous solution and water in that order, and dry, yielding 3.4 gfi of the target compound (?!+, 4).

:l'-[1-(2,4-diq]2J Cl-1noxy)1del]-1,3,4-A xadiazolin-5-one 2.8g in dimethyl containing 0.24q of sodium hydride Add it little by little to a suspension of 10% formamide under water cooling while avoiding stirring. After addition, chlorocarbonic acid 1
．． 2 g was removed and packed at room temperature; Pour the reaction solution into ice water and extract with 1-liter bottle. The toluene solution taken out from one column was converted into 11-lysylcarano, chroma-1-granoy, or sill-like [''
The target compound (NII, 5 > 3.20 is obtained.

The active compounds of the present invention can be formulated into dosage forms such as emulsions, wettable powders, bases, wobbles, powders, and granules by applying conventional formulation methods.

Furthermore, the compounds of the present invention can be combined with other decontamination agents. In addition, in order to expand the range of action, pesticides other than herbicides, such as insecticides, fungicides, and ii'X, II
can be written.

Examples of typical dosage forms are shown below. "Parts" in the explanatory text indicate parts by weight.Example 1. Compounds listed in Group 1 as hydrating agent strength components; A wettable powder containing 50% of the active ingredient compound is prepared by mixing and pulverizing 00 parts of diatomaceous acid, 35 parts of clay, 3 parts of polyoxyethylene alkylallyl needlesulfonic acid sorter, and 2 parts of sodium alkylnaphthalene sulfonate. obtain.

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

Example 2. Granules 5 parts of the compound in Table 1. Bentonai 1-20 parts, clay 73
1 part and 2 parts of sodium dodecylbenzenesulfonate were mixed together, about 20 parts of water was added, and the mixture was kneaded in a C mixer, passed through a granulator, and then dried and sized to form a powder containing 5% of the active ingredient. Obtain granules.

Example 3. Compound xylene 80 shown in Table 1 as an emulsion active ingredient
1 part and 5 parts of polyoxyethylene alkylaryl l-del are mixed to form a homogeneous solution to obtain an emulsion containing the active ingredient. When using, dilute with water to the specified concentration and spray.

Novel 1,3.4-,dxadiazoline-5 of general formula 1
Since -one derivatives have excellent herbicidal activity, they are suitable for controlling weeds growing in fields, orchards, non-agricultural lands, etc. When this active f/l-compound is sprayed on the soil surface or mixed into the soil, it can significantly inhibit the growth of 941 grass and cause it to wither. It is also possible to control miscellaneous Apex by spraying a water solution on the leaves of growing weeds.

If you select the drug M of this compound in November and apply the sheath to 1 to 5 kQ per 11 ktar, you will get 1 to 5 kQ of paddy rice.
shi, wheat, barley, ku 1 heu 1-bi, dice,
It can be used as a selective herbicide in cultivated fields such as peanuts, sunflowers, jaggery, cotton, and satin trees. In addition, when the application rate is increased, it can be applied as a selective herbicide.

The compounds of the present invention can be used, for example, to control the following weeds: f! IJ/-'5, twin eastern plants, such as chickweed (3tclaria media), whitebait (
Chenopodium), Tsumekoori (Sagima japo++1ca),
Chonopodiun + ficirol
Polygonum Qn), Polygonum Qn
(oddosum), slip I: l (portul
aceoleracec+), Booth' no (C
apsella bursapastoris ),
Gunpine pear (L cpidivm virgini)
cum), dogfish (PO white ppa 1nclica)
), Cardamine l-1ex
uosa), Ijibi (Δbutilon avicen)
nae), American Kingoji Power (Sida 5pi)
nosa), Pomoea p.
urpurea), Senecio v.
ulgaris), Oninogushi (3oncl+us
asper), 7 me') force 1 Danigusa ([3Idan
s rrondasa), Book 4 No. Δl1lLlr
O3ta arjQIll! S! aefOl! a)
, A 5ter 5ubulatus,
Hotokeno IJ' (1-amium amplexic
avle), oxalis (Qxalis cornico)
late), AA (Δ+narantl+vs
rctroflexus), crow tree pea (V
1cia 5ativa), Yaemugura (Qalt
um perenna), dog wheat (3romus
calharticos), oat (A van
a tatua), P olypoon
l-1igegaweri), 71Ari (nokibi (
Panicum t1icl+olo+nn-1Nor
o) CyBrus mrcror ()-family weeds, such as CyBrus mrcror J (CyBrus mrcror=a)
, Cyperus 1ria , Cyperus acicula ([E Ieocl+aris acicula)
ria) etc.

The compounds of the present invention have excellent herbicidal efficacy against a wide range of weeds as described above, and are effective against 9:Il+ on the ground surface or on the stems and leaves of plants at the time just before the weeds enter Bi or immediately after germination. 11 (Cloth-4 Rudosa) on the surface or submerged in water, has an extremely high pest control effect.

Also, when the compound of the present invention is mixed into soil, it has an extremely excellent weed control effect! t be beaten.

In order to demonstrate the herbicidal effect of the herbicide according to the present invention, some representative test examples will be given (described in detail below).

Test Example 1 Pre-emergence soil treatment (pre-emergence 5oi
l Reatme-nt) Removal effect on plants when soiled Fill volcanic J * soil + 1 in a pot with a pot area of 100 cn + 2, and add 1g of crabgrass (1) to 1 g of taria sa.
nguinalis), Golden millet (E ct+1noc)
l+loa crus-galli), Polygonum nodosum, Bluetail (Δl1laral mountain+us retroflexus)
), l-corn (Z ea mays ), IJ
lxgi(-1-riticu+n aestivum
), -17E Boo Ri (Phaseolus ra)
cliatus) seeds and cover with soil to a thickness of about 5 mm. Immediately thereafter, the compounds listed in Table 1 were prepared into a wettable powder according to Example 1, and this was diluted with water. 10 k (corresponding to I) per hectare was applied to the soil surface of each plant.The herbicidal effect on the plants was investigated 2 weeks after the treatment.The herbicidal effect was visually observed.
: No effect to 5 : Complete withering as indicated in Table 2 using a 6-level index.

Test Example 2 Stem and leaf contact treatment ([oliar Sl] I・ay tre
(atment) Herbicidal effect on plants when volcanic ash soil is filled in a container with a surface area of 100 cm2.
Kingfisher (D 1g1ta4a sanguinali)
s), Golden millet ('cl+1nocl+Ioa cru
s-galli), Japanese knotweed (l) 01y (JO
ITLIIll 110dO3Ull+), Aobiyu (
AmaranLhus retroflexus),
1 ~ Corn (Z ea mays), wheat (T
riticc+m aestevu+n), enter 7 e booli (pHaseollIs radiall
ls) seeds were sown, covered with about 1 cm of soil, and placed in a greenhouse until the weeds had grown to 1-2 leaves] 1.1. The amount of the drug was diluted with water equivalent to 1000 fL/ha and sprayed using a sprayer.After 10 sprays of the drug, it was investigated using the same criteria as in Test Example 1 and displayed on a 6-level index.The test results were As shown in Table 3.

Test Example 3 Herbicidal effect on paddy weeds and phytotoxicity test on paddy rice A bowl with a surface area of 120 cm 2 was filled with water DJ soil,
l l! ), Monochoria v.
Aginalis) seeds were mixed into the superficial soil of 20...
arls) and paddy rice weeds at the 2nd stage were transplanted to 2/7 locations, respectively, and the water depth was maintained at approximately 3 cm. After 3 days, a hydrating powder containing the compound of the present invention prepared according to Example 1 was poured into water in an amount equivalent to 10 kg per hectare. I did it.

Three weeks after the chemical treatment, the herbicidal effect and chemical damage to paddy rice were investigated. The herbicidal effect and the chemical damage to crops were determined in Test 1.
Column 1 was investigated using the same criteria and displayed on a 6-level index.

The test results are shown in Table 4 and d3.

Table 4 shows that the compounds of the present invention are effective in killing important weeds in paddy fields, such as weeds such as Japanese grasshopper, Japanese grasshopper 1', and Japanese grasshopper.

(Margin below) Table 2 Fe sprouting soil treatment Science 3: Stem and leaf processing Table 4 Flooding treatment

Claims (1)

[Claims] 1) General formula (where R1 is 1-1, or Cl-13:R2 is (-(,
or CH3; X, Y are 0 magazines, or CH3; Z is CN, C
OOC+-(3,000G 21-15, phenyl,
Does not indicate chlorophenyl or 1-lyl. ) A 1,3,4-oxadiazolin-5-one derivative represented by 2) General formula (where R1 is Hl or CI-f3; R2 is 1-1, or CHa:X, Y is C, or CH3; Z is CN, 000
Ct-13, COOC21-15, phenyl, chlorophenyl, or a 1,3.4-71kyrie-di)7zolin-5-one derivative represented by (~1.!) as an active ingredient. Contains a herbicide.