JPH01186868A - Pyrazole compound and herbicide containing said compound as active ingredient - Google Patents

Abstract

NEW MATERIAL:A pyrazole compound expressed by formula I (X is halogen). EXAMPLE:5-tert-Butyl-3-(N-dimethylcarbamoyl-N-methylamino)pyrazole. USE:useful as a herbicide, capable of remarkably inhibiting growth of weeds and killing the weeds by spraying on the soil surface or mixing in soil and also controlling the weeds by spraying on foliar parts of the weeds during growth, effective against broad-leaved weeds, such as chickweed, gramineous weds, such as annual bluegrass, and cyperaceous weeds, such as flat-sedge, with low phytotoxicity to crops. PREPARATION:As shown in the reaction formula, a compound expressed by formula II is reacted with N,N-dimethylcarbamoyl chloride in the presence of an inorganic base, such as sodium carbonate, in an organic solvent, such as benzene, at 30-120 deg.C to afford the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel pyrazole compound and a herbicide containing the same as an active ingredient.

[Prior art and problems to be solved by the invention] Conventionally, 3-(N-alkylamino)-5-tert-butylpyrazole derivatives and their herbicidal activity are known in JP-A-80-4171. . but,
The pyrazole compound related to the present invention is a compound having a urea structure, and is a novel compound having a different functional group from the amide structure or carbamate structure of the above-mentioned known compounds.

Furthermore, 3-(5-tert-butylpyrazolyl)urea□ derivatives are known from JP-A-58-144372. However, these known urea derivatives have a problem in herbicidal effect at low doses.

The present invention aims to provide novel pyrazole compounds exhibiting excellent herbicidal activity.

[Means for Solving the Problems and Summary of the Invention] The present invention is based on the general formula I [wherein X represents hydrogen or a halogen atom]. The present invention provides a pyrazole compound, which is a new compound not described in literature, represented by the following formula, and a herbicide containing the compound as an active ingredient.

X represents a hydrogen atom or a)rogen atom. Here, examples of the halogen atom include a chlorine atom, a fluorine atom, and a bromine atom, and preferably a chlorine atom and a fluorine atom.

Although the compound of formula (1) has tautomers such as the following formula (1'), in the following explanation, both are represented by one formula.

The compound of the present invention is characterized by having a tert-butyl group at the 5-position of the pyrazole ring, as shown in formula (1), and has a very significant herbicidal activity.

The compound of general formula (I) exhibits strong herbicidal activity against a wide range of weeds, and the active ingredient is applied at a rate of 0.1 per hectare just before the weeds germinate or at an early stage of their growth.
When 10 kg to 10 kg is applied, a wide range of weeds as described below can be killed within about 1 to 2 weeks.

In addition, by limiting the amount of this compound applied or by applying an appropriate application method, it is possible to cultivate specific crops such as corn, potatoes, sugarcane, peanuts, soybeans, sunflowers, barley, wheat, turgid, cotton, and fruit trees. Weeds can be selectively controlled in the field.

The compound of the present invention can be produced, for example, according to the following reaction formula. (In the formula, lu is as described above.) This reaction is usually carried out using 5-tart-butyl-3 in an organic solvent such as benzene, toluene, xylene, carbon tetrachloride, methylene chloride, dioxane, acetonitrile, or acetone.
-(N-methylamino)aminopyrazole (n) is dissolved in the presence of an inorganic base such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate,
Add N-dimethylcarbamoyl chloride and add 30 to 12
The mixture is heated to 0°C and stirred.

Compound (1) produced by the above reaction is generally sparingly soluble in water, but relatively easily soluble in ordinary organic solvents, and particularly well soluble in alcohols, acetone, and the like. However, it is difficult to dissolve in petroleum solvents such as hexane and pentane.

The raw material compound (n) used in the above reaction can be produced by reducing formylamino pyrazole, for example, according to JP-A-80-4171.

Next, the method for producing the compound of the present invention will be specifically described.

Production example 1゜5-tert-butyl-3-(N-dimethylcarbamoyl-N-methylaminopyrazole (compound magnetic 1) (I
:X■H) 5-tert-butyl-3-(N-methylamino)pyrazole a, oeg was dissolved in 50ml of acetone, and 3.00ml of anhydrous potassium carbonate was added. added. 246 g of N,N-dimethylcarbamoyl chloride was added dropwise to this mixed solution while stirring. After the addition, the mixture was heated and circulated for 7 hours. After cooling to room temperature, insoluble materials were filtered, and the slaked solution was concentrated under reduced pressure. Water was added to this and extracted with ethyl acetate, and the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting pale brown oil was subjected to silica gel column chromatography, and the white solid obtained by elution with ethyl acetate was recrystallized from a mixed solvent of ethyl acetate and n-hexane to obtain the target compound &1. 2.3 g of colorless crystals were obtained. (51% of theoretical yield) 1H-NMR60MHz CDCj! 3δ t, 3
0(911,s, -C(CII3)3).

2.75 (611,a, -N(CH3)2).

3.20(3H2s, -NCH3)- 5,68 (IH, s, Aros, H).

9.90 (LH, br, s, NH).

Melting point 115-116℃ Production example 2゜5-tert-butyl-4-chloro o-3-(N-dimethylcarbamoyl N-methylamino)pyrazole (compound 2><1:X-Cl>Compound No., 1 4 .5g
was dissolved in 50 ml of methylene chloride, 4.0 g of sulfuryl chloride was added, and the mixture was heated under reflux for 3 hours. After cooling to room temperature, an aqueous sodium carbonate solution was added, stirred, and then separated, and the organic layer was washed with water. This organic layer is taken, dried over anhydrous sodium sulfate, concentrated, and crystallized by adding hexane. filter,
By washing the crystals with hexane and drying, 4.8 g
The desired compound magnetic compound 2 is obtained.

'H-NMR60MHz CDCl! 361.40 (
91,S, -C(CH3)3).

2.66 (8H1s, -N(CH3)2).

3.11(3H,S,-NCH3).

Melting point: 153-154°C The compound of the present invention can be made into dosage forms such as emulsions, wettable powders, pastes, flowable powders, powders, etc. by applying ordinary 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 compound of the present invention, 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 50 parts of the active ingredient compound. A hydrating agent containing % is obtained.

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

Example 2. Granules 5 parts of the compound of the present invention, 20 parts of bentonite, 73 parts of clay and 2 parts of sodium dodecylbenzenesulfonate are mixed, 20 parts of honsuri is added and kneaded with a mixer, and then granulated with a granulator. Then, the mixture is dried and sized to obtain granules containing 5% of the active ingredient.

Example 3. Emulsion As active ingredients, 15 parts of the compound of the present invention, 80 parts of xylene and 5 parts of polyoxyethylene alkyl allyl ether are mixed to form a homogeneous solution to obtain an emulsion containing 15% of the active ingredients. When using, dilute with water to the specified concentration and spray.

- The new pyrazole derivative of formula (R) has excellent herbicidal activity and is suitable for controlling weeds growing in fields, orchards, non-agricultural lands, etc. This active compound can be sprayed on the soil surface or Alternatively, when mixed into the soil, it can significantly inhibit the growth of weeds and cause them to die.Also, the agent can be sprayed on the foliage of growing weeds to control weeds.

The dosage of this compound is regulated to reduce the application amount to 0 per hectare.
．． If you select 1 to 10 kg, corn, wheat,
Barley, sugar cane, soybean, peanut, sunflower,
It can be used as a selective herbicide in fields where potatoes, cotton or fruit trees are grown. 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 Stellaria media, Ch.
enopodlus album), Sag
lnajapanica) S Koakaza (Chenop
odlumflclfo11us+).

Polygonus nodosus
, Portulaca virginlucus)
Rollppa 1nd1ea) S Tanetsukebana (C
ardasine flexuosa), Ichibi (A
butllon theophrasti), SIda 5pinosa, Ipog+oeapurpurea, Seneculo vulgars, Sonchus asperus, B. ldens frondosa), pigweed (Ambrosia artesisiaefoll)
a) Aster 5ubulatus
) - Hotokenoza (Lamluwawplex1caul
e) Oxalis cornlcula
ta), Amaranthus retro
flexus), crow tree pea (Vlcla 5
ativa), Yaemugura (Galiusapari)
ne), Dogweed (SOIanul nlgrul)
), Datura st.
Poa annua, Poa annua, Poa annua, Poa annua, etc.
lopecurus aequalls)% crabgrass (
Digitalia adscendens), E.
chinochloa crus-galli), Agropyron-Kasojl-, Lollum perenne s Dogwheat (
Bro*usunioloides), oat (
Avena fatua), Polypo
gon Higegaveri) s.
anicus dlchotomlflorum), Cyperaceae weeds such as Cyperus
s 51erolrla)S Cype
rus 1ria), Eleochari
s aelculars), etc.

The compounds of the present invention have excellent weed efficacy against a wide range of weeds as described above, and are particularly effective when applied to the field surface or the foliage surface of plants just before or after weed germination. High pest control 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. In addition,
In the test examples, herbicidal effects and phytotoxicity were observed with the naked eye and expressed on an 11-level index from 0: no effect or phytotoxicity to IO: complete death. Moreover, compound A is disclosed in JP-A No. 58-144372.
The compound described in No.

Test example 1゜Pre-emergence soil treatment (pre-emergence 5oi
Weeding effect on plants when using ltreat■ent) A pot with an area of 150 cj was filled with volcanic ash soil.
s Golden millet (Echlnochloa crus-ga)
Rusex obtus
ifolius), Aobiyu (A+*aranthu)
sretroflexus), corn (Zea
5ays), Chrysanthemus
Coronarium) seeds were sown, covered with about 5 II m of soil, and immediately after that, the compounds listed in Table 1 were prepared into a wettable powder according to Example 1, and this was diluted with water.
A dose corresponding to 4.2 kg of active ingredient per hectare was applied to the soil surface of each pot. The herbicidal effect on plants was investigated two weeks after treatment. Table 1 shows that the compounds of the present invention have high herbicidal activity when treated with soil before germination.

Test example 2° Follar 5play treat
ment) Herbicidal effect on plants in the case of Dlgitaria adscendens Fill a pot with a surface area of 150 C with volcanic ash soil,
Golden millet (Behlnochloa crus-gal)
ll) %Rusex obtusi
folius) S Aobiyu (Amaranthusr)
etroflexus), corn (Zea 5a
ys), Chrysanthemum c
oronarlus) seeds, covered with about 1 cm of soil and placed in a greenhouse, and when the weeds had one or two leaves, a hydrating agent of the compound of the present invention was applied at a dose of 1000 I, equivalent to 4.2 kg per 1 hectare. /ha of water and sprayed using a sprayer. Mouths were examined 2 weeks after treatment. The test results are shown in Table-2. Table 2 shows that the compounds of the present invention have high herbicidal activity even in foliage contact treatment.

Test Example 3゜Herbicidal effect on paddy field weeds and phytotoxicity test on paddy rice A pot with a surface area of 120 cm was filled with paddy soil,
Chlnochloa crus-gall), Monochorla vaglnalls s
Amsannia 1ultiflor
a), Firefly (Scirpus juncoides)
) seeds were mixed into the superficial 2 cm of soil, and the seeds of E.
leocharis acliculars) and 2
Transplant paddy rice weeds in the leaf stage to two locations each, and raise the water depth to approximately 3.
Keep it at cm. Two days later, a hydrating powder containing the compound of the present invention prepared according to Example 1 was administered into water at a dosage equivalent to 4.2 kg per hectare.

Three weeks after chemical treatment, the herbicidal effect and chemical damage to paddy rice were investigated. The test results are shown in Table-3.

From Table 3, it can be seen that the compounds of the present invention are effective in killing weeds, which are important weeds in rice fields, such as Japanese grasshopper, Japanese grasshopper, Japanese commonweed, Japanese bulrush, and Japanese grasshopper. However, there is a considerable amount of chemical damage to rice.

Test example 4゜Pre-emergence soil treatment
1 treatg+ent) Weeding effect on plants Fill a pot with an area of 325cj with volcanic ash soil,
Corn (Zca 5ays), Tsurugum (So
rghuablcolor), rice (Oryza 5a
tiva), rhubarb (Glycine wax), tomato (Lyeopersicone sculentu)
m), Chrysanthemumco
ronarluts), crabgrass (Digltari)
a adscendens)S Inubi” (Echin)
ochloa crus-gall), Polygonua nodosust, Portulaca oleracea, Chenopodluwalbum, Ichibi (Chenopodluwalbum)
Butllon theophrasti), Golden Deer (Slda 5pinosa), Fulva Morning Glory (Iposoa purpurea),
Onamomi (Xanthiugastruwariuw)
Sow the seeds, cover with soil to a thickness of about 5 mm, and immediately after that,
The compounds listed above were prepared into a wettable powder according to Example 1, and this was diluted with water to obtain a drug containing the active ingredient equivalent to 6.4.2.1° s kg per hectare. amount was applied to the soil surface of each pot. Three weeks after treatment, the herbicidal effect on plants was investigated. Table 4 shows that the compounds of the present invention have low phytotoxicity to crops and high herbicidal activity when treated with soil before germination.

Test example 5° foliage contact treatment (Foliar 5play treat
ment) Herbicidal effect on plants when soiled Pots with a surface area of 825 cJ were filled with volcanic ash soil and
usbicolor), rice (Oryza 5atlv
a) Glycine wax, tomato
(Lycopers lconeculentus)
, Chrysanthemum coron
arius), Dlgltaria ad
scendens), Golden Millet (EchinochFo
a crus-gall) s giant knotweed (Pol
ygonus nodosum), purslane (Por
tulaca oleracea), Shiroza (Che
nopodlumalbu@), Ichibi (Abutll)
on theophrasti), American golden deer (3ida 5p1nosa), Malva morning glory (
Ipomoea purpurea), Onamomi (X
anthlumstrusarlus) seeds,
When the weeds have grown to 1 to 2 leaves, cover the soil with about 1.3 kg of soil and place it in the greenhouse.
,4゜2, 1. 1000 doses equivalent to 0.5 kg
It was diluted with water equivalent to II/ha and sprayed using a sprayer. Three weeks after the treatment, an investigation was conducted using the same criteria as Test Example 1. The test results are shown in Table-5.

From Table 5, it can be seen that the compounds of the present invention have low phytotoxicity to crops, but high herbicidal activity when subjected to foliage contact treatment.

Claims (1)

[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X represents hydrogen or a halogen atom. ] A pyrazole compound represented by 2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents hydrogen or a halogen atom. A herbicide containing a pyrazole compound represented by ] as an active ingredient.