JPS6013783A - Thiophene derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (X and Y are CH3 or Cl; m and n are 0 or 1). EXAMPLE:Phenyl N-[1-methyl-1-(2-thienyl)ethyl]carbamate. USE:A herbicide having excellent herbicidal activity against wide range of weeds, and exhibiting especially high controlling effect when applied to the surface of the soil or the leaf of the weed or in the water of the paddy field just before or after the sprout of the weeds. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II with the compound of formula III in a solvent such as benzene in the presence of a base such as a tertiary amine, preferably at a temperature between the room temperature and the refluxing temperature of the solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a thiophene derivative represented by the following general formula and a herbicide containing the compound as an active ingredient.

(However, X, Y are CH3 or CLS m, n are 0 or *j
21 is shown. ) The thiophene derivative of the present invention represented by the above general formula is a new compound that has not been published in literature, patents, etc., and as a result of synthesizing it and conducting detailed research, it was found that it can be used as a herbicide. It was recognized that it had a positive effect.

That is, the compound of the present invention exhibits strong herbicidal activity against a wide range of weeds, and the effective amount of the compound can be applied to 0.5 to 20 kli per hectare before the weeds germinate or at the early stage of their growth. When applied, after about 1 to 2 weeks, the area will become wider as described below! It can kill four weeds.

In addition, by applying the present compound in a limited amount or by applying an appropriate application method, it can be applied to corn, potatoes, sugar cane, peanuts, soybeans, sunflowers, and other crops.

Typical examples of the compounds of the present invention include those shown in Table 1.

In addition, the compound is indicated by the symbol in the above general formula. In addition, the value in the physical property column is the nuclear magnetic resonance waves, the value in 0 is the solvent,
mp indicates the melting point, and the display method followed the conventional method.

Table-1 The compound of the present invention can be synthesized, for example, according to the following formula.

The compound of the above general formula is synthesized by route a) or route b). In b), the reaction is promoted by adding a catalytic amount of a tertiary amine such as triethylamine.

As the solvent, for example, an inert solvent such as benzene, toluene, chloroform, dichloromethane, dioxane, ethyl ether, tetrahydrofuran, acetone, methyl ethyl ketone, dimethyl formamide, dimethyl sulfoxide, acetonitrile, or a tertiary amine used as a base can be used. preferable.

The reaction temperature is generally from room temperature to the reflux temperature of the solvent.

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

<Synthesis example> 1-methyl-1-(2-chenyl)ethyl isocyanate 1. 0.94% of phenol in a solution of 5Qm of cyclohexane. ! ? Add 3 drops of triethylamine while shaking well. After standing overnight at room temperature, the obtained crystals were recrystallized from benzene-cyclohexane to obtain 2.2 g of the target compound (A1).

1.1 g of O-cresol was added to a solution of 1.7 g of 1-methyl-1-(2-chenyl)ethyl isocyanate in 50 ml of benzene, and while shaking well, triethylamine 3
Add drops. After standing overnight at room temperature, the mixture was heated under reflux for 4 hours, and the solvent was distilled off under reduced pressure. The resulting residual liquid is purified by florisil column chromatography (toluene solvent) to obtain 1.8 g of the target compound (A2) as white crystals.

The active compounds according to the invention can be formulated into dosage forms such as emulsions, aqueous preparations, pastes, flowable powders, granules, 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. "Department" in the description
indicates parts by weight.

Example 1. As active ingredients for a wettable powder, 50 parts of the compounds shown in Table 1, 10 parts of diatom, 35 parts of clay, 3 parts of sodium polyoxyethylene alkyl allyl ether sulfonate, and 2 parts of sodium alkylnaphthalene sulfonate were mixed and ground. A hydrating powder containing 50 active ingredient compounds is obtained.

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

Example 20 Granules 10 parts of the compound in Table 1, 20 parts of bentonite, Ri V 68
1 part and 2 parts of sodium dodecylbenzenesulfonate are mixed together, 20 parts of honsuri is added and kneaded in a kneading machine, then granulated through a granulator, and then dried and sized to contain 10% of the active ingredient. Obtain granules.

Example 3. An emulsion containing 15 □ parts of the active ingredient, 40 parts dimethylacetamide, 40 parts xylene, and 5 parts polyoxyethylene alkyl allyl ether, is mixed to form a homogeneous solution, and contains 15 parts of the active ingredient. get.

Before use, dilute with water to the specified concentration and spray.

The new thiophene derivatives of general formula I have a herbicidal action and are therefore suitable for controlling weeds growing in rice fields, fields, orchards, non-agricultural lands, etc.

When this active compound is applied to the soil surface or mixed into the soil, it can significantly inhibit the growth of weeds and cause them to die. It can also be used to control weeds by spraying it on the stems and leaves of weeds that are still growing.

Regulate the dosage of this compound and apply the amount per hectare! 1
l11~1'Okl? When selected, it can be used as a selective herbicide in cultivated fields such as paddy rice, corn, wheat, barley, sugarcane, soybean, peanuts, sunflower, potato, cotton, or fruit trees. 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, dicotyledonous plants, such as chickweed (Stallarmedia), ciconia (C.
henopodium), Sagima'
japonica), Chonopodiu
m fialfollum ), Japanese knotweed (Pol
ygonum nodosum), Spellhyu (Po
r-tulace oleracea), shepherd's purse (C
apsella bursapas-toria)
l Lepidium virgin
icum), Porippa 1ndic
a ), Cardmmine I (o
xuoaa) 1ichibi (Abutllonavic)
ennae ), American Golden Deer (5ldaspl
nosa), Malpa morning glory (Ipomoea pu)
rpurea) S Iderogik (5eneeio, v
ulgarig), Oninodashi (5onchus a)
sper), Bidens
frondosa), pigweed ('Ambrosia)
artemisiaefolia), Houkidasa (A
ster 5ubu-1atus) s Hotokenoza (Lamium amplvxlcavle), Oxalis (Oxalla cornlcolate),
Aobi 1 (Amaranthus retroflex)
us ), Vicla 5ativ
a), Gallumspurium
, dogbeast (5olanurn nigrum)
.

Datura stramonl
um ) 1 Monochoria vag
Poa annu & ), Poaceae plants such as Poa annu & , Poa annu &
Alopeculus aequalis), Mehishi i4 (Digitaria adsendang)
, Ohishi/Z (FJleuslneindiaa)
, eno=+ogusa (5etaria viridis
), Inubi'L (Kehinochlor crua
-galli), Agropyron
tsukughiensig), Hosomugi (Loll)
um perenne) 1 Dogwheat (Bromu@
eatharticos), oat (Aven
a tatua), Polypogon
Hlgegaweri), Pan
ieum dlchotornifloram), Cyperaceae weeds such as Cyperus
s m1crol-ria), Cyprus vulgaris (Cyp
erus 1r1a), Eleocha
ris aaicularla), etc. The compounds of the present invention have excellent herbicidal efficacy against a wide range of weeds such as those mentioned above, and are especially effective against a wide range of weeds such as those mentioned above, especially when applied to the field surface or the foliage surface of plants immediately before or after the weeds germinate. Alternatively, when sprayed in flooded areas, an extremely high pesticidal effect can be obtained.

Also, 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-emergent soil treatment (pre-emergenae 5oi
Weeding effect on plants when using volcanic ash soil in a dead area of 1006 nm, and
ig), Golden millet (Echlnochloa cru
s-galli), Polygonu
m nodosum), Amaranth
usretroflexus), corn (Ze
a mayg), wheat (Triticum aes)
tivum), Phaaeolus ra
dlatua) sow yuzu, about 5. Immediately after that, prepare the compounds listed in Table 1 into a wettable powder according to Example 1, dilute this with water, and prepare a drug with an active ingredient equivalent to 101ψ per hectare. amount was applied 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 on a 6-level index from O: no effect to 5: complete death.

Test Example 2 Foliar 5play treat
herbicidal effect on plants when
), dogfish (Echlnochloa krug-
galli), Polygonum
nodosum), Amaranthus
retroflexus ) )) Zea
maye )% wheat (Triticum nest
lvum), Yaenari (Phaseolus ra)
diatus) seeds are sown, covered with soil of about ILyn, placed in a greenhouse, and when the weeds have one or two leaves, an irrigation agent of the compound of the present invention is applied at a dose of 1000 jj+10 kg per hectare. It was diluted with 1/ha of water 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 field weeds and phytotoxicity test on paddy rice A pot with surface g1206n2 was filled with paddy soil,
Eehinoehoa arus-galli),
Monoohoria vaginalll@)
The seeds of Maipai (E
leocharis aaieularis) and two-leaf stage rice weeds were transplanted to two locations each, and the water depth was approximately 3 cm.
Keep it at rn. Three days later, an aquarium containing the compound of the present invention prepared according to Example 1 was administered into the water in an amount equivalent to 10 kg per hectare (IJ).

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.

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

Table 2 Pre-germination soil treatment

Claims (1)

[Claims] 1) A thiophene derivative represented by the general formula % (where X and Y are CH3 or CL, and mon is O or 1). 2) A herbicide containing a thiophene derivative represented by the general formula % (wherein, X and Y are CH5 or CtN, and m*n is O or 1) as an active ingredient.