JPS604160A - Carbamate derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:The compound of formula (X is O or S; R is methyl or ethyl). USE:A herbicide effective widely to broad-leaved weeds (white-bird's-eye, smooth pigweed, pearlwort, smartweed, common purslane, etc.), gramineous weeds (e.g. annual poa, foxtail, manna-grass, etc.), cypraceous weeds (e.g. chufa, slender spiderush, etc.), etc. it exhibits especially high activity when applied just before or after sprouting of the weeds. Rate of application: 1-20kg/1ha. PREPARATION:The compound of formula is obtained e.g. by reacting alpha,alpha-dimethylbenzylisocyanate with the corresponding phenolic compound in the presence of a catalyst such as triethylamine.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides carbamate derivatives represented by the general formula % (wherein, related to herbicides.

The carbamate derivative of the present invention represented by the above general formula is a new compound that has not been described in literature, patents, etc., and is a useful compound as a herbicide.

Representative examples of the compounds of the present invention are as follows. To synthesize the compounds of the present invention, for example, they can be easily synthesized from α,α-dimethylbenzyl isocyanate and the corresponding phenols according to a conventional method. be able to. Note that this reaction is promoted by adding a catalytic amount of a tertiary amine such as triethylamine.

Typical synthesis examples of the compounds of the present invention will be shown below and explained in more detail.

<Synthesis example> Compound No. 1 Ethyl (m-hydroxyphenyl) 3.
]9 α,α-dimethylbenzyl isocyanate 3.2
! Add y to 50 ml of dichloromethane, and add 8.1 ml of triethylamine while stirring well. After heating under reflux for 4 hours, the solvent was distilled off, and the obtained crystals were recrystallized from aqueous ethanol to obtain 6.1I of the target compound (NOI) as white crystals.

Methyl (m-hydroxyphenyl)carbame) 3.3
．． ! 9 and α,α-dimethylbenzyl isocyanate3.
Add 2I to 50 ml of chloroform, add 8.1 ml of triethylamine while stirring well, and add 1 ml of triethylamine at room temperature.
Stir for an hour. Thereafter, the mixture was heated under reflux for 2 hours, and the crystals obtained after distilling off the solvent were collected and washed with n-hexane to obtain the target compound (NO2) as white crystals.

Compound No. 3 S-ethyl (m-hydroxyphenyl) carbamate 4
．． 2.9 and α,α-dimethylbenzyl isocyanate 3
．． 2 g of triethylamine Q and 1 ml of triethylamine Q were added to 401 nl of dichloromethane, and the mixture was heated under reflux for 2 hours. The crystals obtained after evaporation of the solvent are collected and washed with n-hexane to give the target compound No. 3 as white crystals.
can get.

The compound of the general formula shows strong herbicidal activity against a wide range of weeds, and the active ingredient is applied at a rate of 1 to 20 kg per hectare just before the weeds germinate or at the early stage of their growth.
When applied, it is possible to kill a wide range of weeds as described below within about 1 to 2 weeks.

In addition, by limiting the amount of this compound applied or by applying an appropriate application method, specific crops such as corn, potato, sugarcane, peanuts, soybeans, sunflower, barley, wheat, turgsum, cotton, fruit trees, and paddy rice can be grown. 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. Furthermore, in order to expand the range of action, it 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. Parts in the description indicate parts by weight.

Example 1 Wettable powder active ingredients: 50 parts of the compounds shown in Table 1, 10 parts of diatomaceous earth, 35 parts of clay, 3 parts of sodium polyoxyethylene alkyl allyl ether sulfonate, and 2 parts of sodium alkylnaphthalene sulfonate. are mixed and ground to obtain a wettable powder containing 50% of J active ingredient compound.

present Before use, dilute with water to the desired concentration and leave for several minutes.

Example 20 grains 10 parts of the compound shown in Table 1, bentonite = 20 parts, clay 6
8m and 2 parts of sodium dodecylbenzenesulfonate were mixed, about 20 parts of water was added, and the mixture was kneaded with a mixer, then granulated through a granulator, and then dried and sized to obtain granules containing 10% of the active ingredient. get the agent.

Example 3 Milk agent Dilute to the specified concentration and spray.

The novel carbamate derivative of general formula 1 has excellent herbicidal activity and is therefore suitable for controlling weeds growing in fields, paddy fields, orchards, non-agricultural lands, etc.

When this active compound is sprayed on the soil surface, mixed into the soil, or sprayed into submerged water, it can significantly inhibit the growth of weeds and cause them to die.

Weeds can also be controlled by spraying the main agent on the stems and leaves of growing weeds.

If the &tiffi of this compound is regulated and the application rate is selected at 0.5-5 kg per hectare, it can be selected in fields where corn, wheat, barley, paddy rice, sugar cane, dice, peanuts, sunflower, potato, cotton, or fruit trees are grown. It can be used as a targeted herbicide. It can also be applied as a non-selective herbicide by increasing the application rate.

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), whiteweed (Che)
nopodium), Sagima jap
onica) %Coa Kaji (C11onopodium
ficifolium), Polyg.
onum nodosum), portulaca (Portu
laceoleracea), shepherd's purse (Capsel)
la bursapastoris), Lepidium virginicum (Lepidium virginicum)
), Porippa 1ndica, Cardamine Hexuosa, Abutilorl avicennae, Sida 5pinosa, Ipomoea purpurea. (Seneci.

vulgaris), Sonchus '
asper) z candy (Aster 5ubulatu)
s), Lamium amplexica
Oxalis cornicol
ate), Amaranthus retr
offlexus), crow pea (Vicia 5)
ativa), Yaemugura (Galium spuriu)
m), Solanum nigrurn
), Datura stramo
nium), Mochoria vagina
lis), grass family plants such as Poaceae (P. lis), etc.
oa annua), sparrow gnome (Alopec)
ulus aecualis), crabgrass (Digi
Tar 1aadsenden's), Ohishiba (El
eusine 1ndica), Enocologusa (Set
aria viridis), dogfish (Echino
chlor crus-galli), A.
gropyron tsukushiensis)S loliumperenne (Loliumperenne), barley (B
romus catharticos), oat (
Avena tatua)s Polyp
ogon Higegaweri), Ogon Higegaweri (Pa.
nicum dichotom-iflorom), Cyperaceae weeds, e.g.
s m1croiria), Cype
rus 1ria), Eleocharis
acicularia) etc.

The compounds of the present invention have excellent herbicidal efficacy against a wide range of weeds as mentioned above, and can be sprayed on the surface of fields, submerged water, or on the foliage of plants, especially just before or after the weeds germinate. When this is done, an extremely high pest control effect can be obtained.

Furthermore, 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-germination soil treatment (pr, e-energy 5
Weeding effect on plants when using oil treatment) Volcanic ash soil was filled with volcanic ash soil in a bomb with an area of 100 i.
Golden millet (Echinochloa crus-gal)
li), Polygonum nodo
sum), Aobiyu (Jma; anthusretr
offlexus), corn (Xea mays)
Seeds of , wheat (Tritium aestivum), and japonica (Phaseolus radiotus) were sown and covered with soil to a depth of about 5 m, and immediately after that, the compounds listed in Table 1 were prepared into a wettable powder according to Example 1. death,
This is diluted with water and the active ingredient is 10% per hectare.
kg of aHffi was applied to the soil surface of each pot. The herbicidal effect on plants was investigated two weeks after treatment. The herbicidal effect was observed with the naked eye and was 0. No effect to 5: Shown in Table 2 on a 6-level index of complete withering.

Test Example 2 Foliar 5play treat
ment) Herbicidal effect on plants when soiled. Fill a pot with volcanic ash soil with a surface area of 100 crl and plant Digitaria sanguinalis.
, Echinochloa crus-ga
'1li), Polygonum n.
Amaranthus r
etro-flexus), corn (Zeam
ays), wheat (Trjticum aestiv)
um),, Phaseolusradia
tus) seeds are sown, covered with soil of about JCIn and placed in a greenhouse. When the weeds have 1 to 2 leaves, a hydrating powder of the compound of the present invention is applied at a dose of 1.0 kg per hectare.
It was diluted with water equivalent to 00013/ha and sprayed using a sprayer. Ten days after the chemical spraying, the test was conducted using the same criteria as in Test Example 1, and the results were expressed using a 6-level index. The test results are shown in Table 3.

Test Example 3 Herbicidal effect on paddy weeds and phytotoxicity test on paddy rice A pot with a surface area of 120 Crl was filled with paddy soil, and Nobi-r
-(Echinochoa crus-galli),
Monochoria vaginalis
The seeds of E.
leocharis acicularis) and two-leaf stage rice weeds were transplanted to two locations each, and the water depth was approximately 3 cm.
Keep it IrL. Three days later, a hydrating powder containing the compound of the present invention prepared according to Example 1 was administered into water at a dose corresponding to IQI (g) per hectare.

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 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.

From Table 4, it can be seen that the compounds of the present invention are effective in killing weeds, which are important weeds in paddy fields, such as grasshoppers, Japanese grasshoppers, and Japanese grasshoppers.

Claims (1)

[Scope of Claims] 1) A carbamate derivative represented by the general formula (wherein X represents an oxygen or sulfur atom, and R represents a methyl or ethyl group). 2) A herbicide containing a carbamate derivative represented by the general formula (wherein X represents an oxygen or sulfur atom and R represents a methyl or ethyl group) as an active ingredient.