JPS6251684A - Thiazolyl alkyl or thienyl alkyl ester of aplha-imidazolinone nicotinic acid and aplha-imidazolinone benzoic acid - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides lfr-specific α-imidazolinone niconane modified and α-imidazolinone benzoic acid thiazolyl alkyl and chenyl alkyl esters and their respective The present invention relates to a method for producing a novel compound.

The present invention also relates to compositions containing the novel imidazolinone compounds and methods of using them for persistent control of weeds or regulation of plant growth. The thiazolyl alkyl and chenyl alkyl esters of α-imidanolino/butyrate of the present invention are represented by the general formula (I) (wherein A is a carbon atom having 1 to 6 carbon atoms). iA s+J1'!- or a branched alkylene chain, Q and Ql each independently represent a mochi atom or a methine group, R, and 16 each independently represent a hydrogen atom or carbon; 4c
; Represents an alcohol base having 1 to 4 atoms, X and Y
are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a fluorenyl group having 5 to 4 carbon atoms, and a fluorenyl group having 1 to 4 carbon atoms.
represents a haloalkyl group, or a halogen atom, or together represents a butadiene group. ).

In the above definitions, alkyl and alkylene groups are linear or branched, e.g. methyl, methylene, ethyl, ethylene, propyl, propylene, improvil, 1- or 2-
Methyl ethylene, butyl, petite/, secondary butyl, 1
-Methylpropylene, imbutyl, 2-methylpropylene/, tertiary butyl, 2,2-dimethylethylene and 1
．． It may be 2-dimethylethylene.

Halogen is fluorine, chlorine, bromine or iodine.

The production of such compounds can be represented by the following reaction formula.

11aill■ Base (1,8-diazobicyclo[5,4,O]]ampku7-nin■b11 1(1) The method of the present invention for the preparation of imidazolinone compounds of formula 1 (Ha) or ( flb) (wherein, Q,
and Y are the same as defined in formula (I). ) with thiazolyl alcohol or chenyl alcohol and an inert organic solvent. It is recommended that the reaction be carried out in the presence of a base in a selection agent.

Suitable bath media for these reactions are substantially anhydrous hydrocarbons, ethers or ketones such as benzene, toluene, xylene, hexane, cyclohexane diisozolobyl ether, tetrahydroctane and dioxane.

Examples of suitable bases are sodium hydride, 1,8-diazabicyclo(5,4,0]undec-7-ene, tertiary amines and alkali metal hydroxides.

These reactions are carried out in a temperature range of 0° to 200°C, generally at the center of the reaction mixture.

The starting materials of formula (■a) are known or they can be prepared by known methods, for example published European Patent Application No. 4.
No. 1623, N-(α-ingzolo-α-methylacetamide)-2,3-pyridinecarboximide or N-(
It is produced by condensing α-ingzolo-α-methylacetamide) 7talimide.

a N-(α-inpropyl-α-methylacetamide) 7
Thalimide can be obtained by condensing phthalic anhydride with 2-amino-(α-inpropyl-α-methylacetonitrile). The nitrile must then be converted to the diazide amide by heating in an aqueous acid. The viridi-7-2,5-dicarbonate-modified α-inzolobyl-α-methylacetamide of the formula (Foundation) is produced by converting unsaturated olehydrazone into 2-
Chloro- or 2-promo N-(α-ingzolo-α
- Methylacetonitrile) can be combined with succinimide and then subjected to hydrolysis to produce an ionic acid.

(In the above formula, R' and IL" are hydrogen or an alkyl group having 1 to 4 carbon atoms, Haj is a chlorine atom or a Mino atom, and X and Y are the same as defined in formula (I). ) The starting material of formula <l1b) is the above N-(α-ingzolo-α-methylacetamide)-2,3-pyridinecarboximide or N-(α-inpropyl-α-methylacetamide)phthalimide in water. 2-(4-isopropyl-4-methyl-5-oquinimidazolidine) nicotinic acid derivative in the presence of an aqueous solution, such as a sodium chloride solution, and then with gold, a condensing agent in an inert organic solvent. The starting material of 2nb (2-isopropyl-2-methyl-3ti-imidazo(p,2/:1.2)viaaa[5,4-b)viridiy-3, 5-dione), !7 can be obtained.

Such nicotinic acid esters and methods for their preparation are described in published European Patent Application No. 41625.

One of the suitable condensing agents for this cyclization is strong, for example! A water absorbent such as cyclohexanecarbodiimide, thionyl chloride or phosked in the presence of 1 mole of sulfuric acid or anhydride, or a small amount of dimethylformamide.

The condensation can also be carried out effectively by placing the reaction mixture in a water separator.

If the reaction cannot be carried out at room temperature, the reaction is carried out in the temperature range of 0°C to 200°C. For example, the reaction mixture is heated to its boiling point (if necessary) and then cooled (if safe) with water/water or water/rM water.

An appropriate group for these tightening reactions 1 or hydrolysis reactions 6 is, of course, sodium hydroxide, sodium carbonate, 7
Kg sodium oxide, calcium oxide, charcoal, calcium chloride, potassium chloride modified calicum, ammonia-free melon groups and trinium amines such as trinibulamines.

Suitable solvents are, for example, polar, neutral solvents which can be used on their own or in the form of a mixture of at least two solvents.

Among the novel esters of formula (I), the highly active nicotinic acid ester is characterized by the fact that Q and Ql are nitrogen atoms in coughing. Or, it is an alkyl group having 1 to 4 carbon atoms and has the linear formula (Ia).

and in particular the following compounds.

4-Methylthiazol-5-ylethyl 2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-imidacillin-2-yl)nicotinate, 4-methyldeanol-5-ylethyl 5-methyl- 2
-(5-isopropyl-5-methyl=4-oxo-4,
5-dihydroimitazolin-2-yl) nicotinate, 4-methylthiazol-5-ylethyl 5-〇-propyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazoline-2- yl) Nicotinate, 4-) Tiltia Sol-5-ylethyl 5-isopropyl-2-(5-inpropyl-5-methyl-4-okino-4,5-dihydroimidazolin-2-yl) Nicotinate (2 is nitrogen atom%) Qi is a methine group, IC1, X and Y are each hydrogen or an alkyl group having a number of 1 to 4, and the following formula (Ib) is represented by the following formula (Ib): It is also effective when using the following: Hitsukumono.

Thiophen-2-ylethyl 2-(5-isopropyl-
5-Methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate, 4-methylthiophene-
2-ylethyl 5-mether-2-(5-isopropyl-
5-Methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate, 4-Mefluteophen-2-ylethyl 5-ethyl-2
-(5-isopropyl-5-meth-4-ogine-4,
5-dihydrotazoli/-2-ylnicotate, 4-) fkfoffen-2-ylmethyl 5-methyl-2
-(5-isopropyl-5-methyl-4-oxo-4,
5-dihydroimidazolin-2-yl)nicotinate, 4-)f-ruthio7-en/-2-ylmethyl-5-en-2
-(5-inoprobyl-5-methyl-4-oxo-4.
5-dihydroimidazolin-2-yl) nicotinate.

Q must be a methine group, Ql is a nitrogen atom, and each of L, L, X and Y is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or X and Y The benzoic acid thiadiazolyl alkyl ester, which together represent a butadiene bridge, has the following formula (lc) 1%.

It is effective for seven days.

4-Methylthiadiazol-5-ylethyl 2-(5-
Isopropyl-5-methyl-4-oxo-4,5-dihydroimidazoli/-2-yl)pe/shade is particularly effective.

Good law 1! +: Q and Qt are methine groups,
R1+几3. Each of X and Y is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or X and Y together form a butadiene bridge, and the following formula (le) 几! Also, when Q is a nitrogen atom and Qt is S
M-chord atom or methine group, tb, R1 and R are water: IAlIA atom or alkyl group having 1 to 4 carbon atoms, X and Y together form a butadiene bridge, and the following formula (If ) and 3-quinolinic acid thiazolyl alkyl and hytheenyl alkyl esters. The present invention relates to all diastereoisomers and diastereoisomers of compounds of formula (I).

Compounds of formula (I) usually contain (105 to 4 snouts/ha,
In particular, it can be applied to neck I4 work at a time of (11 to 1 ha).

When used at low application rates, the compounds in the formula have good selective growth inhibition and selective herbicidal activity. He also goes through it to use it.

In some cases, it can cause problems even for weeds that could only be controlled by using all herbicides. The mode of action of these compounds is quite unusual.
jt't - can move. That is, the compound is absorbed by the plant, moves to other parts of the plant, and then develops its action there.

In this way, for example, it is possible to injure the roots of perennial weeds by surface treatment. Compared to other herbicides and plant growth regulators, the new compounds of formula (I) are effective even when used at very low application rates.

The compound represented by formula (I) has a so-called KIA plant growth inhibitory property. Inhibits the growth of monocotyledonous and dicotyledonous plants.

For example, compounds of formula (I) may be added to leguminosae, which is often planted as an intercrop in the tropics.
) selectively inhibits the growth of Thereby, intercropped plants are not able to compete with the cultivated plants, which prevents soil snacking between the cultivated plants. Suppression of plant height growth in many cultivated plants is
Planting more plants allows K sowing in the area.

As a result, higher convergence per unit area is possible.

The mechanism of increased convergence using growth regulators is as follows:
This is based on the fact that, because plant height growth is suppressed, nutrients are increasingly able to promote the formation of calluses and fruit set.

When the compound of formula (I) was applied at high rates, all test plants were stunted in their development and died.

The present invention also relates to weed control and growth regulating compositions containing the novel compounds of formula (I) for the control of weeds, pre- or post-emergence, and of monocotyledonous and dicotyledonous plants, especially umbrellas, The present invention relates to a method for inhibiting the growth of tropical intercropped crops and suckers of tobacco plants.

The compounds of formula l can be used in their neat form or, preferably, in the conventionally used bAi! Use with auxiliary agents. Therefore, in a known manner, emulsion concentrates,
direct sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, powders, granules and
They can also be formulated, for example, in capsules in polymeric materials. The method of application, such as spraying, scattering, scattering or injection, is selected in advance depending on the purpose and general circumstances, such as the nature of the formulation.

formulations, i.e. compositions containing a compound of formula I (one infant component) and, if appropriate, solid or liquid auxiliaries;
The preparations or mixtures are prepared in known manner, for example by homogeneous mixing and/or comminution of the active ingredient with fillers such as solvents, solid carriers and, if appropriate, surfactants.

Suitable solvents include aromatic hydrocarbons, preferably those containing 8 to 12 carbon atoms, such as xylene mixtures,
substituted naphthalenes, phthalates such as dibutyl 7-thalate or dioctyl phthalate, aliphatic hydrocarbons,
For example cyclohexane or paraffin, alcohol,
Glicol and its erthyl and esters.

Examples are ethanol, edene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ketones such as cyclohexanone, strong polar solvents such as haemether-2-pyrrolidone, dimethyl sulfoxide or dimethyl formamide, epoxidized vegetable oils such as epoxidized coconut, etc. Can be filled with oil, soybean oil, or water.

The solid carriers used, for example for dusts and dispersible powders, are usually natural mineral fillers, such as calcite, Merck, kaolin, montmorillonite or attapulgite. In order to improve the physical properties, it is also possible to add highly dispersed silicic acids or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous, for example pumice, brick chips, sepiolite or bentonite; suitable non-solvent carriers are materials such as calcite or sand. Very large amounts of pre-granulated inorganic and organic materials can be used, such as dolomite or powdered plant residues.

Depending on the nature of the compound represented by 2I to be formulated,
Suitable surface-active compounds are nonionic, cationic and/or anionic surfactants with good emulsifying, dispersing and water availability properties. The term "surfactants" is also enriched with a mixture of surfactants.

Suitable anionic surfactants 11 are both water-soluble fabrics and water-soluble synthetic surfactant compounds.

Suitable soaps are higher fatty acids (10 to 22 carbon atoms)
Alkali metal, alkaline earth gold m or unfl provided or! Ammonium salts such as oleic acid, stearic acid, or sodium and potassium salts of natural fatty acid mixtures obtained from beef tallow, for example, coconut oil fc. Mention may also be made of the preparation of fatty acids from methyltaurine salts.

However, so-called synthetic surfactants are used more often, especially fatty sulfonates, fatty sulfates, sulfonated penzimidanol derivatives or alkylaryl sulfonates.

Fatty sulfonates or sulfates are usually alkaline,
It is in the form of alkaline earth or unconverted ammonium salts containing alkyl groups having 8 to 22 carbon atoms, including the alkyl part of acyl groups, such as sulfonic acid, dodecyl sulfonate, etc. Sodium or calcium salts of acids or mixtures of fatty alcohol sulfates obtained from natural fatty acids. These compounds also include those consisting of sulfonate salts of fatty alcohol/ethylene oxide adducts and salts of (pItcW&esters).Sulfonated benzimidazole derivatives contain two sulfonic acid groups and one carbon atom. Examples of alkylaryl sulfonates include the sodium salt, calcium salt or triethanolamine salt of a condensation product of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or dibutylnaphthalenesulfonic acid and formaldehyde. Corresponding phosphorous salts, such as the salts of phosphoric esters of adducts of p-nonylphenol with 4 to 14 moles of ethylene oxide, are also passed.

Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or derivatives of saturated or unsaturated fatty acids and alkylphenols, these derivatives containing from 3 to 10 glycol ethers, 8 Preferably, the (aliphatic) hydrocarbon 1 contains from 6 to 20 carbon atoms, and the alkyl portion of the alkylphenol contains from 6 to 18 carbon atoms.

Preferred nonionic surfactants include polyethylene oxide and polypropylene glycol, ethylenediamine polypropylene glycol, and 1 to 1 alkyl group.
A water-soluble adduct with an alkylborizolopylene glycol containing 0 carbon atoms;
Contains 0 ethylene glycol ether groups, 10 to 1
00 zorobylene glycol ether group. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of nonionic surfactant j'+11 include nonylphenol-polyethoxyethanol, mustard oil polyglycol ether, polypropylene/polyethylene oxide adduct, tributylphenoxy7-bolyethoxyethanol, polyethylene glycol, and octylphenoxypolyethoxyethanol. It is. Fatty acid esters of polyoxyethylene norbitan, such as polyoxyethylene rubitan trioleate, are also suitable nonionic surfactant AIJs.

The cationic surfactant has at least one polyglycol ether or 8 carbon atoms as an f'J-Mt substituent.
Quaternary ammonium salts containing an alkyl group of 1 to 22 and a lower unsubstituted alkyl group, a benzyl group, or a lower hydroxyalkyl group as a central substituent are preferred.

These melons are preferably in the form of halides, methyl sulfate or ether sulfate, such as stearyltrimethylammonium chloride, chloride, or penzyl di(2-chloroethyl-ethylammonium fluorite).

Surfactants commonly used for formulations are:

For example, it is described in the following literature. McCutcheon's Annual Report on Detergents and Emulsifiers
ethergents and &xulsifiers
Annual”) x Musi Publishing (MCPubl)
isching corp, ), ridgewood, new jersey.
sey), 1981; [Surfactant Handbook] @ Ten5sd-Ta5chenbuch
” C,) lanser Verlag.

Munsch lit Vienna, 1981° Herbicides are usually [Ll to 95%, preferably α1 to 80%].
1 to 99.9
% of solid or liquid auxiliaries and 0 to 25%, preferably 1 to 25% of surfactant.

A preferred formulation is one having the following composition in % (Excellent represents *:tS).

Emulsifiable concentrate Compound of formula (I): 1-20%, preferably 5
~10 surfactant: 5~30≠, preferably
10-20% liquid carrier: 50-94%, preferably
70-85 multi-powder compound of formula (I): (11-10 minutes, preferably
Solid carrier for a1-1: 99.9-90%, preferably 99.9-99%. ^%W4. ．． U! Compound of formula (I): 5-75%, preferably 1
0-50% water: 94-25%, preferably 90%
~50% surfactant: 1-40%, preferably
2-30 hydrating powder formula (compound of υ: [L5-90 preferably 1-
80% surfactant: α5-20, preferably 1
~15 solid carriers 25 to 95 times, preferably 1
5 to 90 granules of formula (I): α5 to 30, preferably
3-15% solid carrier: 9? , 5-70 Vi, preferably 97-85% Although commercial products are preferably formulated as concentrates, the end user will usually use them in diluted form. The formulation can be diluted to a low concentration such as α001. The application rate is usually 0.0 of the active ingredient.
05-5 4+a, i, /ha.

The compositions can also contain further ingredients, such as stabilizers, defoamers, viscosity regulators, binders, adhesives, as well as fertilizer casings or other compounds, in order to obtain specific effects. .

The preparation of a number of compounds of formula (I) is illustrated by the following examples. The other compounds listed in the following tables are prepared by similar methods.

Example 1: 4-methylthiazol-5-ylethyl 2
-(5-(cyclovir-5-methyl-4-oxo-4,
5-Dihydroimidazolin-2-yl) Nicotinate Tetrahuman o7 Run 5 Orll, 9t(Q5.5-
Dioxo-2-isopropyl-2-methyl-2,3-dihydroimidazo (1', 2': 1.2]-5-)
1-pyrrolo L 3.4-b ]pyridine, 5.5f 5
-(2-Hydroxyethyl)-4-methylthiazole and 2 drops of 1,8-diazabicyclo(5,4,0)undec-7-ene in a sulfurized flask for 5 hours at NM
Reflux. 7. The solvent is then applied in vacuo and the initial oily residue is triturated with 50% ether.
72 products crystallize out. The remainder is obtained by concentrating the mother liquor and crystallizing from acetone/ether. The crystal melting point is 154-157°C, and the yield is a52.

3,5-dioquine-2-isopropyl-2-methyl-2,3-dihydroimidazo(1
', 2': 1.2)-5-)1-pyrrolo'C5°4-b] Pyridine is produced by the following pressure.

Under stirring, 2-(5-isopropyl-5-methyl)-2
-oxo-2-imidacillin-2-ylnicotine fi1
! &6j' (105 moles) are added to a solution of dicyclohexylcarbodiimide 11.1F in total dicyclohexylcarbodiimide. Stirring is continued for an additional 2 hours at room temperature.

The resulting dicyclohexylurea is removed by suction filtration,
The residue is washed with a small amount of methylene chloride. The P solution is concentrated by evaporation, and the remaining Fk is then recrystallized from ethyl acetate/compound. The title compound is obtained in a crystalline form that bath-melts at 152 DEG-153 DEG C. in a yield of 91 (12,1?).

The following starting materials are obtained in a similar manner.

nc3H7fi m, p, 152-135
℃CH(CH3)2 H+n, p, 145-
146℃CzHs k-1m, p, 156
-15+3℃n-C4Hg Hm, p, 1
16-119℃CH3Hm, p, 129-131℃
Run 5112: Chenyl-2-ylethyl 2-(5
-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazoli/-2-yl)nicotinate.

Under a nitrogen atmosphere, water is diluted with sodium chloride (80% in white oil).
%) f y slowly in 100 d of dry toluene.
Add (2-chenyl)to a solution of 10 t of ethanol.

6-isopropyl-3-methyl-3H-imidazol:1',2':1゜2]pyrrolo(3,4
-b) Pyridine-2,5-dione 109 is added and the mixture is then heated under sieve for 1 hour. ρ for finishing
, the reaction mixture is concentrated by evaporation in vacuo. The residue is chromatographed through a silica gel column (eluting with a 1=2 mixture of tetrahydrofuran and petroleum ether). The first portion contains excess chenylethanol. The product is evaporated from the subsequent oil and dried in vacuo.
It is removed in the form of white oil.

W The kernel oil is crystallized in a glass-filled container containing white oil. Yield: title compound 9f, melting at 84-87<0>C.

5-isopropyl-3-methyl-5H-imidazo(1', 2': 1.2)pyrrolo(3,4-b)pyridine-2,5-dione, which is recommended as a starting material, is prepared as follows. Manufactured.

5,7-dihydro-α-isopropyl-α-methyl- in powdered water-based sodium α5v and 100 mJ of toluene.
5,7-thioxo-6H-pyrrolo[3,4-b]pyridine-6-acetamide (iA!it point: 82°C) was added at the same time and heated under IWJ reflux for 2 hours in a water oven.

The reaction mixture is cooled, filtered through 7 liters of water, washed with ethyl acetate and concentrated by evaporation. When the residue is recrystallized from ethyl acetate/petroleum ether, 1
The title compound 151? at 16°C. is attended.

The following starting materials are obtained in a similar manner.

nc3H7Hm, p, 116℃ C! Ha Hrn, p, 119-120
℃n-C4H@ ) (m, p, 86-87
°CCl-1(OH,), H CH3Hm, p, 102-106 °C -(CH=C)i), -H HC)1°CH,CH.

CH(CHsnCtHsH) The compounds listed in the following table are obtained following a similar procedure to that of Examples 1 and 2 using the corresponding starting material JR.

1'\E E E E E E E E ○ Formulation example Example 3: Example of combination of Ij active ingredient expressed by formula 1 (%
(represented in a mold) Silver hydrating agent a) b). ) Table 1~
Compound 6 20% 60% 0.5
% Lignosulfone Sodium Sodium 5% 5%
5% lauryl fig 6 Sodium filtration% -- Highly dispersed silicic acid 5% 27
% 27% Kaolin 67% -- 1 Sodium Salt -- 59.5% After thoroughly combining the active ingredients with the auxiliaries, the mixture is thoroughly ground in a suitable mill, diluted with water, A wettable powder is obtained that allows a suspension of the desired concentration to be obtained.

b) Emulsifiable concentrates a) b) Compounds of Tables 1 to 6 10% 1% oxide 4-5 mol) '5% 3% Calcium dodecylbenzenesulfonate 6% 3%
Cyclohexanone 60% 10% Xylene mixture 50% 79% By diluting this concentrate with water, an emulsion of the desired concentration can be obtained.

Compounds of Tables 1 to 6 0.1% 1% Talc 999% -Kaolin
- 99% 9% active ingredient Mixed with carrier and milled the mixture in a suitable mill to obtain a ready-to-use powder.

d) Extruded granules a) b) Compounds of Tables 1 to 6 10% 1% Sodium lignosulfonate 2% 2% Carboxymethylcellulose 1% 1% Kaolin 87% 96% The active ingredient is mixed and ground with the adjuvant 2 and then the mixture moisten with water. The mixture is extruded and then dried in a stream of air.

e) Wave force granules Compounds of Tables 1 to 6 6% Polyethylene 'J:I-# (MG200) 3% Kaolin 94% The finely ground active ingredient is added to the kaolin moistened with polyethylene glycol in a mixer. Apply evenly. This method yields non-dusting granules.

f) Suspension Concentrate a) b) Compounds of Tables 1 to 6 4 [ ] % 5 %
1 tylene glycol 10% 10%
Sodium nonylphenol polyethylene lignosulfonate 10% 5
%Carboxymethylcellulose 1%
1% 37% formaldehyde aqueous solution 02%
02%75% aqueous emulsion type silicone oil 0.8% 0
．． 8% water 52%
77% finely ground If active ingredient is mixed homogeneously with auxiliary agents and diluted with water to obtain a suspension of the desired concentration.

Salt solution Compounds of Tables 1 to 6 5% Ingzololamine 1% Oxide 78 mol) 3% Water
91% Biological Test One Time 4: Pre-emergence Herbicidal Effect Immediately after sowing the test plants in flower pots in a greenhouse, the test compound obtained from a 25% emulsifying concentrate was applied to the soil surface. Treat with an aqueous fraction of Concentration JjJ of test compound a K7 per hectare is used.

The pots are placed in a greenhouse at 22-25°C and 50% relative humidity. The test is evaluated after 6 weeks according to the following scale: 0 1: plants do not germinate, first withering 2-3: very severe damage 4: severe damage 5: moderate damage, short twigs 6: damage; Plants can regenerate 7-8:
Slight damage 9: Growth following tV similar to that of untreated plants In this test, the compounds shown in Tables 1 to B showed strong herbicidal activity.The results are shown in Table 7. vinegar.

Table 7 Example 5: Post-emergence herbicidal action (contact action) Water-based herbicidal action was applied to a large number of weeds, both monocotyledonous and dicotyledonous, at the 4- to 6-leaf stage after germination at a pressure of 4 times per hectare. A dispersion of the active ingredient is sprayed, and the temperature is 45-60℃ at 24-26℃.
% relative humidity. The test was carried out after 15 days.Example 4
It is evaluated using the same scale.

In this test, the compounds of Tables 1 to 6 also exhibit strong to very resilient herbicidal activity. The results are shown in Table 8.

Table 8 Fruit M1 Example 6: Pre-emergence herbicidal action Plastic pot made of foamed vermiculite (density: o
, 155? Water absorption capacity: o565t/l)
Fill with. After saturating the non-adsorbing vermiculite with an aqueous emulsion of deionized water containing 70.8 ppm of the test compound 'jz concentrated I9, the following plants, Yuzu, were sprinkled on the surface. Orantakashi Na5-turtium
off 1cinalis), Azoroste, Isu
Agrostis tenuis, Ste-11aria media and Agrostis sankinari/F, (1) igi taria
sanguinaL is) pot, then at 20°C.
Place in a climatic chamber with approximately 20 lux lighting and 70% relative humidity. During the germination period of 4 to 6 days, the needles are covered with a light-transparent material and treated with deionized water to increase local humidity. Commercially available liquid fertilizer after 50 years (()reenzit■)
Add 0.05% to water. The test will evaluate pregnancy 12 days after eating one persimmon. The effect on plants can be evaluated according to the scale shown in Example 4. The results are shown in Table 9.

Example 8: Herbicidal action on wild (water) rice Submerged weeds, dog fin and grasshoppers were sown in a glass beaker (surface: 60 cWL2: volume: 500 d). After 1 yuzu, the beaker is filled with water in a trench that reaches the soil surface. Three days after sowing, the amount of water on the surface of the soil (3-5 pieces) will increase slightly.

Three days after sowing, the beakers are sprayed with an aqueous emulsion of the test compound. The rate of use is: concentration of active ingredient 4 K9 per hectare (concentration of spray mixture = 550 t
/ha).

The beaker is then placed in a greenhouse under optimal main branch conditions for rice weeds, i.e. 25-30°C and high humidity.
t<. Test J1: The test was carried out 3 hours after application. In this test, the test compounds in Tables 1 to 6 showed good activity.

Example 9: Inhibition of growth test plants (Centrosema putumieri and Centrosema pubescens) for resuminous intercropped plants in the tropics
f fully grown ox, then i' of 60c1n
Mow at h5. After 7 days, an aqueous emulsion of the test compound was added to the +t14 grain. The test plants were 70
% relative humidity 10.6000 lux of artificial light for 14 hours per day, [maintained at 7itx at 27°C during the day and 21°C at night. The test was conducted 4 hours after application compared to the control.
by evaluating new growth and measuring new growth and determining phytotoxicity.

In this test, a significant reduction in the growth of plants treated with compounds of groups 1 to 6 at concentrations of 50 to 3000 r/ha (20% of new growth vs. untreated)
(below), the test plants can be observed without inflicting puncture wounds.

Example 10: Growth control of soybean Soybean 'Hark' variety sweetened in a soil/beet/sand (6:3:1) mixture in a plastic container. This container is placed into a climatic chamber. This plant can be grown by f2b by adjusting temperature, light, fertilizer addition and water supply to the optimum conditions.
After a week, they will grow to the 5-6 trifoliate stage. The plant then has the formula (
Sprayed with an aqueous mixture of the compound of I) until completely wetted.

The concentration is 1oo 9 a, i, t per hectare.
ll win. The feedback will disappear after approximately 5 seconds after application. Group 1 of the invention compared to untreated control
The compounds of the above are extended! -) 4: Increase the number and weight of harvested siliques.

Example 11: Growth inhibition of cereals, spring wheat (Hordeum vulgare) and white wheat (5ecale) are sown in sterile soil in plastic beakers in a greenhouse and watered as required. Grass shoots are approximately 21 cm after adding 1 Pi+.
On day one, the patient is treated with an aqueous spray mixture of Groups 1-6 compounds. The concentration is ID0jF' of active ingredient per hectare!
It corresponds to Grain growth is evaluated by sowing on the 21st day after application. Comparison with untreated controls shows that new growth of treated cereal plants is reduced (60-90% of control) and in some cases stem diameter is increased. Example 12: Rice Inhibition of growth of grasses of the grass family Lolium bere 4 (Lolium pc -renn)
e), Poa pratensis)
, Ushinokegu G (Fe5tuca ovina)
, Kamokaya (Dactylis glomerate)
) $Cynodon dact 9Kishige (Cynodon dact
ylon) Mosquito, put soil/beet/sand (6:
3:1) of 2b' and fl:I was sprinkled on a plastic dish with the required amount of water.

So (V) Grass that grows larger should be cut at a height of 4 cm.

Approximately 50 days after sowing the yuzu 1 and 1 day after the last cutting, the yuzu is sprayed with 1 g of an aqueous spray mixture of compounds 1 to 6.

Concentration of test compound in trt L, 500 y/ha
3. It corresponds to the proportion for a in it.

Grass growth is 211 after application. The test compounds also cause a reduction in new growth in the range of 10-50% compared to untreated II controls.

13: Drying and defoliating effect deltafin (1,)61tapine) in %j (r
Grow it in a single-purpose container in a rjMiB+OIk greenhouse. After the capsules are formed, the plants are grown in Table 1. ',
The aqueous 'e:J combination of compounds of No. 6 can be sprayed in field applications at application rates corresponding to 1.2, 0.6 and Q, 3 Ky/ha. The evaluation of the test was based on the determination of the degree of defoliation (percentage of fallen leaves) and desiccation (drying from leaves remaining on the plant) on days 3, 7 and 14 after application of the active ingredient. It will be done.

In this study, test compounds of Groups 1 to 6, with 4', knee+, applied VNI of Q, 6 and t 2 kg/ha.
After 7 days, the plants treated with this treatment had only a few dry leaves (80% defoliated and dry).

1j fortune 1j fortune teller

Claims (23)

[Claims] (1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 are mutually R_1 and R_2 independently represent a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y independently represent a hydrogen atom, a carbon atom, Alkyl group having 1 to 4 atoms, 1 to 4 carbon atoms
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) Thiazolyl alkyl or thienyl alkyl esters of acids or alpha-imidazolinone benzoic acids. (2) The compound of formula (I) has the following formula (Ia) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ia) (In the formula, R_1, R_2 4) represents an alkyl group.
-Imidazolinone Nicotinic acid 2-thiazolyl alkyl ester. (3) 4-methylthiazol-5-ylethyl 2-(5
2. The compound according to claim 1, which is -isopropyl-5-methyl-4-oxo-4,5-di-hydroimidazolin-2-yl) nicotinate. (4) 4-Methylthiazol-5-ylethyl 5-methyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate Claim 1 Compounds described in Section. (5) 4-methylthiazol-5-ylethyl 5-n-
Propyl-2-(5-isopropyl-5-methyl-4-
The compound according to claim 1, which is oxo-4,5-dihydroimidazolin-2-yl)nicotinate. (6) 4-Methylthiazol-5-ylethyl 5-isopropyl-2-(5-isopropyl-5-methyl-4-
The compound according to claim 1, which is oxo-4,5-dihydroimidazolin-2-yl)nicotinate. (7) The compound of formula (I) has the following formula (I b) ▲Mathematical formula, chemical formula, table, etc.▼(I b) (In the formula, R_1, R_2, X and Y are hydrogen atoms or carbon atoms represents an alkyl group of 1 to 4)
-Imidazolinone Nicotinic acid 2-thienyl alkyl ester. (8) The compound according to claim 1, which is thiophen-2-ylethyl 2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate. (9) 4-Methylthiophen-2-ylethyl 5-methyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate Claim 1 Compounds described in Section. (10) 4-Methylthiophen-2-ylethyl 5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate Claim 1 Compounds described in Section. (11) 4-Methylthiophen-2-ylmethyl 5-methyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate Claim 1 Compounds described in Section. (12) 4-Methylthiophen-2-ylmethyl 5-ethyl-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydroimidazolin-2-yl)nicotinate Claim 1 Compounds described in Section. (13) The compound of formula (I) has the following formula (I c) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I c) (In the formula, R_1, R_2, X and Y are hydrogen atoms or have 1 carbon atom to 4 alkyl group, or X and Y together form a butadiene bridge)
-imidazolebenzoic acid 2-thiazolyl alkyl ester. (14) 4-methylthiadiazol-5-ylethyl 2
-(5-isopropyl-5-methyl-4-oxo-4,
The compound according to claim 1, which is 5-dihydroimidazolin-2-yl)benzoate. (15) The compound of formula (I) has the following formula (I d) ▲ formula,
There are chemical formulas, tables, etc. ▼ (I d) (In the formula, R_1, R_2 X and Y represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or X and Y together form a butadiene bridge. α expressed as
-Imidazolinonebenzoic acid 2-thienyl alkyl ester. (16) The compound of formula (I) has the following formula (I g) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I g) (In the formula, R_1 and R_2 are hydrogen atoms or carbon atoms of 1
4 represents an alkyl group. 2. The compound according to claim 1, which is a 2-thiazolyl alkyl ester or 2-thienylmethyl ester of α-imidazoliinone-quinone-3-carboxylic acid represented by the following formula. (17) General formula (IIa) or (IIb) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (IIa) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (IIb) (In the formula, Q represents a nitrogen atom or a methine group. In the expression, X and Y are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms.
represents an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together represents a butadiene group). III) ▲ Formula,
There are chemical formulas, tables, etc. ▼ (III) (In the formula, Q_1 represents a nitrogen atom or a methine group, and R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.) characterized in that it is reacted with the compound represented by the general formula (I
) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 each independently represent a nitrogen atom or a methine group.) R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Alkyl group, number of carbon atoms is 1 to 4
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) A method for producing a 2-thiazolyl alkyl or 2-thienyl alkyl ester of acid or α-imidazolinonebenzoic acid. (18) The active ingredients include the general formula (I) ▲mathematical formula, chemical formula, table, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 each independently represents a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y each independently represent a hydrogen atom or a methine group; Atom, alkyl group having 1 to 4 carbon atoms, having 1 to 4 carbon atoms
represents an alkoxy group, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together represents a butadiene group. Weeding and plant growth containing 2-thiazolyl alkyl or 2-thienyl alkyl ester of 2-α-imidazolinone nicotinic acid or 2-α-imidazolinone benzoic acid represented by ) together with carriers and/or other auxiliaries. Regulatory composition. (19) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 are mutually R_1 and R_2 independently represent a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y independently represent a hydrogen atom, a carbon atom, Alkyl group having 1 to 4 atoms, 1 to 4 carbon atoms
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) 1. A method for inhibiting unwanted plant growth, which comprises using a thiazolyl alkyl or thienyl alkyl ester of an acid or α-imidazolinone benzoic acid or a composition containing said compound. (20) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 are mutually R_1 and R_2 independently represent a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y independently represent a hydrogen atom, a carbon atom, Alkyl group having 1 to 4 atoms, 1 to 4 carbon atoms
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) A method for inhibiting plant growth, which comprises using a thiazolyl alkyl or thienyl alkyl ester of an acid or α-imidazolinone benzoic acid, or a composition containing the compound. (21) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 are mutually R_1 and R_2 independently represent a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y independently represent a hydrogen atom, a carbon atom, Alkyl group having 1 to 4 atoms, 1 to 4 carbon atoms
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) A method of influencing the growth of plants to increase yield, characterized in that it uses a thiazolyl or thienyl alkyl ester of an acid or alpha-imidazolinone benzoic acid or a composition comprising said compound. (22) The general formula ( I
) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 each independently represent a nitrogen atom or a methine atom. R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Alkyl group, number of carbon atoms is 4 to 4
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) Selection of pre- or post-emergent weeds in a crop of useful plants characterized by treatment with an effective amount of an acid or thiazolyl or thienyl alkyl ester of α-imidazolinone benzoic acid or a composition containing said compound. How to control the pest. (23) A growing plant is expressed by the general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a straight or branched alkylene chain having 1 to 6 carbon atoms, and Q and Q_1 each independently represent a nitrogen atom or a methine group, R_1 and R_2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X and Y each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and a hydrogen atom having 1 to 4 carbon atoms;
an alkoxy group having 3 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a halogen atom, or together representing a butadiene group) A method for inhibiting the growth of plants after the two-leaf stage, which comprises treating with an effective amount of an acid or a thiazolyl alkyl or thienyl alkyl ester of α-imidazolinone benzoic acid or a composition containing the compound.