JPH07196425A - Agent for enhancing effectiveness of agrochemical - Google Patents

Abstract

PURPOSE:To obtain an agent for enhancing effectiveness, being safe to environment and capable of enhancing effects of existing herbicides. CONSTITUTION:This agent for enhancing effectiveness of herbicides is characterized by containing metabolites of Collectotrichumtabacum of a filamentous fungi.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a herbicide potency enhancer containing a metabolite of a filamentous fungus. Therefore, the chemical industry,
It is useful in the fields of agrochemical manufacturing, fermentation and agriculture.

[0002]

2. Description of the Related Art Although there are many descriptions about synergistic action written in patents, literatures, etc., in most cases, it is a description about a pesticide that the effect is superior or inferior when two kinds of pesticides are mixed. . Examples of substances having an effect of enhancing the efficacy of herbicides include dimethyl sulfoxide, nonionic surfactants, synthetic fats and oils, synthetic unsaturated fatty acids and esters,
Ammonium sulfate, etophane, urea, azacycloalkane, (thio) acylazacycloalkane, DEET
(N, N-diethyl-m-toluamide), ABT (aminobenzotriazole), 2,4-DP {(2,4 dichlorophenoxy) -1-propyne}, SKF525A
(Diethylaminoethyl-2,2-diphenylbutyric acid),
Diethyldithiocarbamate, 4-octyl-2-acetylphenol oxime, pyridine-2,6-dicarboxylic acid, di-2-ethylhexylphosphoric acid, tetraethylenepentamine, triethylenetetramine, Silwet
Enzymes such as L77, piperonyl butoxide, retinoid, casein and lipase, pectinase, cellulase and depolymerase are known.

Japanese Unexamined Patent Publication (Kokai) No. 1-117810 describes a method for increasing the pharmacological effect of agricultural chemicals using an enzyme. However, since the enzyme is used, the activity changes depending on the temperature, so There is a problem in stability, and there is a problem in practicality. Grassell et al. (Biotechno
logic for Crop Protection,
Am. Chem. Soc. Symposium Ser
ies 379, Chapter 1, Biorati
onal Herbicide Synergist
s, pp. 1-24) focuses on the fact that the herbicide incorporated into the weeds is decomposed and detoxified in the weeds, and describes chemical substances that inhibit the action of glutathione-S-transferase and monooxygenase detoxifying enzymes. ing. However, these compounds are not natural products existing in nature, and there is concern about their effects on the environment.

[0004]

Recently, there have been serious problems such as environmental pollution due to excessive use of organic synthetic herbicides, and reduction of control effect due to emergence of drug-resistant weeds. The concern over the effects of chemical herbicides on the human body and the natural environment has become a concern, and interest in biological pesticides has increased, leading to active research and development of biopesticides.
However, the pesticide-free cultivation method and the biological control method are still in the midst of research, and it is a fact that a stable control effect cannot be obtained by their single application and sufficient crop production cannot be expected. In any case, reducing the application amount of the organic synthetic herbicide is very significant from the viewpoint of safety.

In order to maximize the effect of the herbicide, techniques such as improvement of the formulation method and addition of a spreading agent have been used, and some effects have been achieved. The disadvantage is that it is a substance that is not found in nature, has no biodegradability, accumulates in nature, and is likely to lead to environmental damage. In addition, a so-called synergistic effect, which is more than expected when two different pesticides are mixed, was known.
Its effects are generally weak and not always synergistic.

In order to solve these problems of the prior art, the present invention searches for a stable compound that replaces an enzyme, and a metabolite of a microorganism that already exists in nature and can be expected to be biodegradable, and enhances the efficacy of herbicides. It is an object of the present invention to find a herbicide potency enhancer that has the above-mentioned properties and can be used even in actual use situations. Further, the present invention aims to improve the efficiency of absorption of herbicides to weeds, reduce the application dose of organic synthetic pesticides, and develop a potency enhancer that provides safer and sufficiently practical weed control. To do.

[0007]

[Means for Solving the Problems] The present inventors focused on the diversity of the metabolites of filamentous fungi, and by applying the metabolites of filamentous fungi to plants, the surface structure of the plant was changed and weeding The method of increasing the absorption efficiency of the herbicide into the organism and making the herbicide more effective with a smaller amount of herbicide was investigated. As a result, as a result of screening the metabolites of a wide variety of filamentous fungi, it was found that the extract containing the metabolites of choletotricham tabacum (hereinafter simply referred to as “extract”) has the effect of enhancing the efficacy of the herbicide, and the enhancement of the efficacy of the herbicide. The active substance was isolated and the chemical structure was determined, and it was found that orcinol and 4-chloroorcinol are the active substances. Then, by mixing the extract of choletotricum tabacum, orcinol or 4-chloroorcinol with a herbicide to treat weeds, a surprisingly potentiating effect is produced, and the herbicides are treated without affecting the crops. It was found that the expected excellent effect can be obtained even if the application rate is reduced, and the present invention has been completed.

The extract, orcinol and 4-chloroorcinol according to the present invention have no effect on crops, and when mixed with some chemical herbicides, they are harmless to crops. The herbicidal action can be dramatically improved. That is, the extract according to the present invention, orcinol and 4-chloroorcinol and chemical herbicides, atrazine, cotran, tolcan, photosynthesis-inhibiting herbicides such as bentazone, bensulfuron-methyl,
Pyrazosulfuron-ethyl, chlorosulfuron-methyl, imidazolidinone, glyphosate, bialaphos and other amino acid synthesis-inhibiting herbicides, fusilade, lasso, beacon, molinate, naproanilide, MCP, promethrin, benzophenap, propanil, NSK-850,
HW-52, chrome prop, esprocarb, bifenox, quinclorac, bromobutide, 2,4D
When mixed with etc., weeds can be controlled at an application rate which cannot be controlled by conventional chemical herbicides alone.

As a method of using the extract, orcinol and 4-chloroorcinol according to the present invention as a potency enhancer for herbicides, a method using a filtrate after culturing cells or a method using the extract is used. , Orcinol or 4-chloroorcinol, or a mixture of both. These may be mixed with a herbicide or treated separately. In order to further enhance the effect, it may be used by suspending it in an aqueous solution containing a surfactant or the like, or may be used as a mixture with other herbicides, fungicides, insecticides and other chemical pesticides that do not exhibit antagonistic properties.

In order to obtain the extract, orcinol and 4-chloroorcinol according to the present invention, they may be produced synthetically or they may be obtained by culturing choletotricum tabacum. Although its mechanism of action is not clear,
It is speculated that the extract, orcinol, or 4-chloroorcinol loosened the cuticle layer on the surface layer of the plant and enhanced absorption and transfer of the chemical herbicide.

In order to use the extract, orcinol and 4-chloroorcinol according to the present invention, these drug substances may be used as they are, but they are usually used in the form of oil, flowable or hydrated. It is desirable to use it after preparing it as a drug, emulsion, liquid, or the like. As the carrier, those commonly used for agricultural and horticultural chemicals can be used. For example, as a solid carrier, clay, talc, bentonite, zeolite, calcium carbonate, diatomaceous earth, mineral powder such as white carbon, soybean powder, plant powder such as starch, polyvinyl alcohol, polymer compounds such as polyalkylene glycol Etc. Examples of the liquid carrier include various organic solvents such as decane and dodecane, vegetable oil, mineral oil, paraffin and water.

The amount of the extract, orcinol and 4-chloroorcinol added according to the present invention is 1 ppm to 1
0% is preferably 10 to 10,000 ppm. When the extract of the present invention or orcinol or 4-chloroorcinol is used in the form of a preparation, the content thereof varies depending on the form of the preparation, but is usually 0.05 to 30 in an oil preparation.
% By weight, 1-50% by weight for flowable agent, 1-90% by weight for wettable powder, preferably 0.5-% for oil agent.
15% by weight, 10 to 30% by weight of flowable agent and 10 to 50% by weight of wettable powder, but are not limited to these values.

As the second auxiliary agent, surfactants, binders, stabilizers and the like which are usually used in agricultural and horticultural chemicals can be used alone or in combination as required. As the stabilizer, for example, an antioxidant, a pH adjusting agent or the like is used, and sometimes a light stabilizer can also be used. The content of the second auxiliary agent is 0 to 80% by weight, and the content of the carrier is 100% by weight minus the amount of the active ingredient and the amount of the auxiliary agent.

The efficacy enhancer according to the present invention may be used in combination with one or more of the following chemical herbicides, or pesticides such as fungicides, insecticides and plant growth regulators, fertilizers, soil conditioners and the like. Of course, mixing with these is also possible.
Herbicides that can be mixed include 2,4-dichlorophenoxyacetic acid (2,4-D), 2-methyl-4-chlorophenoxyacetic acid (MCPA), and 2,4,5-trichlorophenoxyacetic acid (2,4,4). 5-T), 2- (2,4-dichlorophenoxy) propionic acid (dichlorpro
p), 2- (2-methyl-4-chlorophenoxy) propionic acid (mecoprop), 2- (2,4,5-trichlorophenoxy) propionic acid (fenopro)
p), 4- (2,4-dichlorophenoxy) butyric acid (2,
4-DB), 4- (2-methyl-4-chlorophenoxy) butyric acid (MCPB), 2- (2-naphthoxy) propionanilide (naproanilide), 2- (1
-Naphthoxy) N, N-diethylpropionamide (n
apropamid), (+)-2- [4- (2,4-
Dichlorophenoxy) phenoxy] propionic acid methyl ester (diclofp-methyl), 2-
[4- (5-Trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid butyl ester (flu
azifop), 2- [4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid methyl ester (haloxyfop), 2-
[4- (3,5-Dichloro-2-pyridyloxy) phenoxy] propionic acid-2-propynyl ester (ch
lorazifop-propynyl), 2- [4-
(6-Chloro-2-quinoxanyloxy) phenoxy]
Propionic acid ethyl ester (quizalofop-
Ethyl), 2-[-4- (6-chloro-2-benzoxazolyl) phenoxy] propionic acid ethyl ester (fenoxaprop-ethyl), 2- [4-
(6-Chloro-2-benzothiazolyloxy) phenoxy] propionic acid ester (fenthiaprop-
Ethyl), 2,3,6-trichlorobenzoic acid (2,3,6-TBA), 3,6-dichloro-2
-Methoxybenzoic acid (dicamba),
2,5-Dichloro-3-aminobenzoic acid (amiben), 3,5,6-trichloro-2-methoxybenzoic acid (tricamba), 4-
Chloro-2,2-dimethyl barrel anilide (monal
ide), 3,4-dichloropropionanilide (pr
openil), 3,4-dichloro-2-methylacrylanilide (dicryl), 3,4-dichlorocyclopropanecarboxyanilide (cypromid),
3,4-dichloro-2-methyl-pentaneanilide (k
arsil), 3-chloro-2,4-dimethylpentaneanilide (solan), N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide (propy).
zamide), N, N-dimethyl-2,2-diphenylacetamide (diphenamide), N-naphthylphthalamic acid (naptalam), N- (1,1)
-Dimethylbenzyl (-2-bromo-ta-ash-butylacetamide (buromobutide), 2-benzothiazol-2-yloxy-N-methylacetanilide (mefenasate),

N- [3- (1-ethyl-1-methylpropyl) 5-isoxazolyl] -2,6-dimethoxybenzenamide, 1,1-dimethyl-3-phenylurea (fenuron), 3 −
(4-chlorophenyl) -1,1-dimethylurea (m
onuron), 3- (4-chlorophenyl) -2,
1,1-trimethylisourea (trimeturo)
n), 3- (4-chlorophenyl) -1-methoxy-1
-Methyl urea, 3- (4
-Chlorophenyl) -1-methyl-1- (1-methylpropyn-2-yl) urea, 3-
(4-Bromophenyl) -1-methoxy-1-methylurea (metobromuron), 1- (2-methylcyclohexyl) -3-phenylurea (siduro)
n), 1,1-dimethyl-3- (3-trifluoromethylphenyl) urea (fllumeturon), 3
-(3,4-Dichlorophenyl) -1,1-dimethylurea (diuron), 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea (linuro)
n), 3- (3,4-dichlorophenyl) -1-n-butyl-1-methylurea (neburon), 3- (3
-Chloro-4-methoxyphenyl) -1,1-dimethylurea, 3- (4-bromo-3)
-Chlorophenyl) -1-methoxy-1-methylurea, 1- (4-difluorochloromethylmercapto-3-chlorophenyl)-
3,3-dimethylurea,
3- (3-chloro-4-methylphenyl) -1,1-dimethylurea,

3- [4- (4-chlorophenoxy) phenyl] -1,1-dimethylurea (chloroxur)
on), 3- [4- (4-methoxyphenoxy) phenyl] -1,1-dimethylurea (difenoxuro)
n), 3- [3- (N-Tashari-butylcarbamoyloxy) phenyl] -1,1-dimethylurea (ka
rbutylate), 3-benzoyl-3- (3,4
-Dichlorophenyl) -1,1-dimethylurea (p
henobenzuron), 1- (α, α-dimethylbenzyl) -3- (4-methylphenyl) urea (dy
mron), 3- (4-isopropylphenyl) -1,
1-dimethylurea (isoproturon), 3-
(2-Benzothiazolyl) -1,3-dimethylurea, 3- (2
-Benzothiazolyl) 1-methylurea (benzth
iazuron), 3- (hexahydro-4,7-methanoindan-5-yl) -1,1-dimethylurea (noruron), 3-cyclooctyl-1,1-dimethylurea (cyclulon), 1,3-dimethyl -3- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) urea (thiazfluro)
n), 1- (5-ethylsulfonyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea, 3- [5- (1,1-dimethylethyl)- 1,3,4-thiadiazol-2-yl] -1,3-dimethylurea (tebuthiuro)
n), 3- (5-tashari-butylisoxazol-3-yl) -1,1-dimethylurea (isouro)
n), 4- [2-chloro-4- (3,3-dimethylureido) phenyl] -2-taashary-butyl-1,3.
4-oxadiazolin-5-one (dimefuro
n), 3- (5-tashari-butyl-1,3,4-thiadiazol-2-yl) -4-hydroxy-1-methyl-2-imidazolidone (buthidazol)
e), 2-chloro-4,6-bis (ethylamino)-
1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-
1,3,5-triazine, 2-chloro-4,6-bis (isopropylamino) -1,3
5-triazine,

2-chloro-4-diethylamino-6-ethylamino-1,3,5-triazine (trietaz)
ine), 2-chloro-4-ethylamino-6-taashary-butylamino-1,3,5-triazine (ter)
butylazine), 2- (2-chloro-4-ethylamino-1,3,5-tyrazin-6-ylamino)
-2-Methylpropionitrile (cyanazin)
e), 2-chloro-4-cyclopropylamino-6-isopropylamino-1,3,5-triazine (pref
ox), 2- [2-chloro-4- (cyclopropylamino) -1,3,5-triazin-6-ylamino] -2
-Methylpropionitrile, 2
-Methoxy-4-secondary-butylamino-6-ethylamino-1,3,5-triazine (secbumet)
on), 2-methoxy-4,6-bis (isopropylamino) -1,3,5-triazine (protome)
n), 2-methylthio-4,6-bis (ethylamino)
-1,3,5-triazine (simetryne), 2
-Methylthio-4,6-bis (isopropylamino)-
1,3,5-triazine (prometryne), 2
-Methylthio-4-methylamino-6-isopropylamino-1,3,5-triazine (ametrine), 2
-Methylthio-4-ethylamino-6-taashary-butylamino-1,3,5-triazine (terbutr)
yne), 2-methylthio-4-isopropylamino-
6- (3-methoxypropylamino) -1,3,5-triazine, 2-methylthio-4- (1,2-dimethylpropyl) -6-ethylamino-1,3,5-triazine (dimethame)
trine), 2-methylthio-4-isopropylamino-6-methylamino-1,3,5-triazine (de
smetryne), 4-amino-6-taashary-butyl-3-methylthio-1,2,4-triazine-5.
(4H) -one, 2-methylthio-4,6-bis (isopropylamino) -1,3,3
5-triazine, 2-taashary-butylamino-4-ethylamino-6-methoxyamino-1,3,5-triazine
on),

2-azido-4-isopropylamino-6
-Methylthio-1,3,5-triazine (azipro
trine), 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5 (4H) -one (met
amitron), 6-taashary-butyl-4-isobutylideneamino-1,2,4-triazine-5 (4
H) -one, 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,3
5-triazine-2,4- (1H, 3H) -dione (h
exazone), ethyl-N- (4-chloro-6)
-Ethylamino-1,3,5-triazin-2-yl)
-Aminoacetate, ethyl-N- (4-chloro-6-isopropylamino-1,
3,5-triazin-2-yl) -aminoacetate, 2-chloro-N-isopropylacetanilide (propachor), N
-Methoxymethyl-2 ', 6'-diethyl-2-chloroacetanilide (alachlor), 2-chloro-
2 ′, 6′-diethyl-N- (butoxymethyl) acetanilide (butachlor), 2-chloro-2′-ethyl-6′-methyl-N- (2-methoxy-1-methylethyl) acetanilide (metolachlor),
N, N-diallyl-2-chloroacetamide (alli
dochlor), 2-chloro-2 ′, 6′-dimethyl-N- (2-methoxyethyl) acetanilide (dim
Ethachlor), 2,6-dinitro-N, N-dipropyl-4-trifluoromethylaniline (trif)
luralin), N-butyl-N-ethyl-2,6-
Dinitro-4-trifluoromethylaniline (benf
luralin), 2,6-dinitro-N-propyl-
N-cyclopropyl-4-trifluoromethylaniline (profluralin), N, N-diethyl-2,
4-dinitro-6-trifluoromethyl-m-phenylenediamine (dinitramine), 4-isopropyl-2,6-dinitro-N, N-dipropylaniline (isopropaline), 2,6-dinitro-N
-Secondary-Butyl-4-Taashary-Butylaniline, 4- (Methylsulfonyl)
-2,6-Dinitro-N, N-dipropylaniline (n
italin), 3,4-dimethyl-2,6-dinitro-N-1-ethylpropylaniline (pendime)
Thalin), 3,5-dinitro-N, N-dipropylsulfanilamide (oryzalin), N-ethyl-N- (2-methylallyl) -2,6-dinitro-4.
-(Trifluoromethyl) aniline (ethalflu
ralin), N, N-diethyl-2,4-dinitro-
6-trifluoromethyl-m-phenylenediamine (d
iethamine),

2-chloro-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl) benzenesulfonamide (chlorosu)
lfuron), methyl-2- [3- (4-methoxy-
6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] benzoate (metsulfur)
one-methyl), methyl-2- [3- (4,6
-Dimethylpyrimidin-2-yl) ureidosulfonyl] benzoate (sulfometuron-met)
hyl), methyl-2- [3- (4-, 6-dimethoxypyrimidin-2-yl) ureidosulfonyl] benzoate, ethyl-2- [3
-(4-chloro-6-methoxypyrimidin-2-yl)
Ureidosulfonyl] benzoate (chlorin
uron), 3-[(4-methoxy-6-methyl-1,
3,5-Triazin-2-yl) ureidosulfonyl] -2-thiophenecarboxylic acid (thiametur
on), 3,7-dichloro-8-quinolinecarboxylic acid (quinchlorac), 3,6-dichloro-2-
Pyridinecarboxylic acid, α-
(2-chlorophenyl) -α- (4-chlorophenyl)
-5-pyrimidine methanol (fenarimol),
S, S-Dimethyl-2- (difluoromethyl) -4-
(2-Methylpropyl) -6-trifluoromethyl)-
3,5-pyridinedicarbothioate, 4-chloro-s
-(Methylamino) -2- (3- (trifluoromethyl) phenyl) 3 (2H) -pyridazinone (norfl
urazon), O, O-bis (1-methylethyl)-
S- [2-[(phenylsulfonyl) amino] ethyl] sulfodithioate (bensulide),
(+)-2- [4,5-Dihydro-4-methyl-4-
(1-Methylethyl) -5-oxo-1H-imidazo-
L-2-yl] -5-methyl-3-pyridinecarboxylic acid (imazamethapyr), 3- [5- (1,1
-Dimethylethyl) -3-isoxazolyl) -4-hydroxy-1-methyl-2-imidazolidione (buso
xynone), 2- [1- (ethoxyimino) -butyl] -3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl) -2-cyclohexen-1-one (cyclodydim).

In particular, when the potency enhancer according to the present invention is used in combination with a chemical herbicide such as urea-based, anilide-based, thiolcarbamate-based, sulfonylurea-based, triazine-based, etc., the herbicidal effect is applied individually. Has an unexpected synergistic effect, and it is possible to control weeds at a lower dose than expected.

[0021]

EXAMPLES The isolation method and biological activity of the substance according to the present invention will be specifically described below. Example 1 Cultivation of microorganisms 1) Method of culturing microorganisms Aseptic inoculation of a strain of choletotricum tabacum into a petri dish containing potato dextrose agar medium and oatmeal agar medium, precultured at 25 ° C for 7 days, and good growth is achieved. The medium was selected. For the main culture, a 500 ml Sakaguchi flask was used, and 100 ml of potato sucrose liquid medium, oatmeal liquid medium or modified zapek dox liquid medium was inoculated with 5 pieces of the mycelium disc of the above-mentioned preculture, and 10 strains per strain were used. Flask, total 1
The liter culture solution was subjected to reciprocal shaking culture at 25 ° C for 7 to 10 days. 2) Large-scale culture method of microorganisms Aseptic inoculation of a strain of Choletotricum tabacum into a petri dish containing potato dextrose agar medium was performed.
Preculture was carried out at 7 ° C for 7 days, and a medium with good growth was selected. For pre-culture, 500 ml Sakaguchi flask was used, 100 ml of modified Czapek Dox medium was inoculated with 5 pieces of mycelium disks, and 10 strains of Sakaguchi flask per strain, total 1 liter of culture solution was used at 7 to 10 at 25 ° C. Culture was performed by day-to-day reciprocal shaking.
In the main culture, a 10-liter jar fermenter was used, 8 liters of modified Czapek-Dox medium was filled, sterilized, cooled, and then inoculated with 400 ml of precultured mycelium. Culturing was performed at 25 ° C. under stirring conditions of 100 rpm,
The culture was carried out at pH 5.0 to 6.7 for 6 days, the culture was repeated twice, and a total of 16 liters was cultured.

Example 2 Preparation of Extract Extract One liter of the culture solution of each strain obtained in Example 1-1) was filtered with a quadruple gauze to separate the cells and the culture filtrate.
The culture filtrate was adjusted to pH 3 with hydrochloric acid, and then filtered with a Buchner funnel preliminarily covered with 3 cm of Celite to remove fine mycelium. This acidic solution was extracted with 2 liters of ethyl acetate and the layers were separated to obtain an ethyl acetate-soluble fraction. The ethyl acetate layer was washed with demineralized water, dried over anhydrous sodium sulfate overnight,
Ethyl acetate was removed by a rotary evaporator, and the solvent was removed by a vacuum pump to obtain the target extract.

Example 3 Assay Using Change in Conductivity as an Index 1 mM-M containing 1% sucrose in a dish having a diameter of 6 cm.
5 ml of ES buffer (pH 6.5) was placed in the leaf disc punched from cucumber cotyledons (diameter 4 m).
m) Floated 50 sheets. 50 μl of a methanol solution of a reagent having a predetermined concentration was added and preincubated for 18 hours in the dark. The next day, 50 μl of a methanol solution was added to the extract obtained in Example 2 so that the final concentration was 3000 ppm, and the electrical conductivity at 0 hours was measured.
The sample was left to stand under the light condition of 8 ° C. and 36000 lux, the conductivity was measured with time, and the change from 0 hours was examined. As a result, the conductivity increases with time, and after 5 hours 170
Reached μS / cm.

The active substances shown below were isolated by using the change in conductivity as an index for the change in the surface structure of the plant. That is, the extracted extract was separated by various chromatographies, each fraction was assayed using the conductivity as an index, and the active fraction was purified as follows. The fractions showing activity in each purification step are underlined in the fraction numbers in Tables 1 to 4. The final concentration of the sample was set to 300 ppm in the purification step after preparative thin layer chromatography.

Example 4 Preparation of Extraction Extraction and Isolation of Orcinol and 4-Chloroorcinol 16 liters of the culture solution obtained in Example 1-2) was filtered with a quadruple gauze to obtain cells and culture filtrate. separated. The culture filtrate was adjusted to pH 3 with hydrochloric acid, and then filtered with a Buchner funnel preliminarily covered with 3 cm of Celite to remove fine mycelium. This acidic solution was extracted with 16 liters of ethyl acetate and the layers were separated to obtain an ethyl acetate-soluble fraction. The ethyl acetate layer was washed with demineralized water, dried overnight with anhydrous sodium sulfate, ethyl acetate was removed with a rotary evaporator, and the solvent was removed with a vacuum pump to obtain 1.6 g of an extract.

The obtained medium acidic extract was purified by silica gel column chromatography. Wako gel C
-300 g of silica gel of -300 is packed in a column, and the extract is charged, and 500 ml of solvent is added so that the content of ethyl acetate is gradually increased from benzene to increase the polarity.
It was eluted one by one. Each of the obtained fractions was subjected to the assay described in Example 3 to determine an active fraction having an increased conductivity. The yield of each fraction is shown in Table 1 (Table 1), and the active fractions are underlined.

[0027]

[Table 1] Fractions 1 and 2 having activity were combined and further subjected to preparative thin layer chromatography of Kieselgel HF254 using a solvent system of benzene-acetone = 1: 1.
Each of the developed bands was separated into 6 fractions, and the assay shown in Example 3 was performed to determine the active fraction with increased conductivity.
Table 2 (Table 2) shows the Rf value and yield of each band. Also, activity was found in bands 1 and 2 as underlined.

[0028]

[Table 2] The active bands 1 and 2 were combined and further subjected to preparative thin-layer chromatography of Kieselgel HF254 using a solvent system of benzene-ethyl acetate = 1: 1 to obtain 5 fractions for each developed band. After separation, the assay described in Example 3 was performed to determine the active fraction with increased conductivity. Third
The Rf value and yield of each band are shown in the table (Table 3). The activity was also found in band 4, as underlined.

[0029]

[Table 3] Finally, the active band 4 was purified by preparative high performance liquid chromatography to obtain two active substances C.
T-1 and CT-4 were obtained. The following preparative conditions
The retention time and yield are shown in the table (Table 4). The active fraction of which the conductivity is increased by the assay shown in Example 3 is underlined. Preparative conditions: Column: Waters Micro Bonder Sphere (5 μC ₁₈ -100A ₁₉ mm × 15 cm) Elution solvent: Methanol: Water = 6: 4, 5 ml / min

[0030]

[Table 4]

Example 5 Active substances CT-1 and CT-
Chemical structure of 4 The physicochemical data of the active substances, CT-1 and CT-4, isolated in Example 4 were obtained from commercially available orcinol and 4-chlorooline obtained by the method shown in Synthesis Example 1 below. When comparing with Lucinol, all data including IR data were in agreement, so CT-1
Was identified as orcinol, and CT-4 as 4-chloroorcinol. IR of CT-1 in Figure 1 and CT-4 in Figure 2
The spectrum is shown.

Synthetic Example 1 Synthesis of 4-chloroorcinol A synthetic example of Duhkhaharan Chakravarti et al. (J. Indian Chem. Soc.,
14 , 730, 1937), and 4-chloroorcinol was synthesized. To 200 ml of an ether solution of 2.8 g of orcinol, an ether solution of 1.7 g of sulfanyl chloride was added dropwise with stirring under ice cooling. The reaction temperature was raised from 0 ° C. to 40 ° C. over 2 hours after the dropping, and then the temperature was returned to room temperature and left overnight to terminate the reaction. The reaction solution was freed from hydrogen chloride generated with sodium carbonate, washed with water, the ether layer was dried over sodium sulfate, the ether was removed under reduced pressure, and an oily product was obtained.
I got 2g. Purification by column chromatography on silica gel gave 1.5 g of 4-chloroorcinol.
(Mp. 115-117 ° C) Each physicochemical data is Du
It was in agreement with the data of hkhaharan et al.

Formulation Example Next, a formulation example of a mixed preparation with an agrochemical potency enhancer and a herbicide according to the present invention will be shown. Formulation Example 1 (Emulsion) Lecithin: 5% by weight, heavy white oil 90% by weight
Orcinol 4% by weight and 1% by weight Triton X
-100 was added and mixed to form an emulsion to obtain an emulsion.

Formulation Example 2 (Emulsion) Lecithin: 5% by weight, heavy white oil 90% by weight
4% by weight of 4-chloroorcinol and 1% by weight of Triton X-100 were mixed and emulsified to obtain an emulsion.

Formulation Example 3 (Emulsion) Chemical herbicide, 1% by weight of atrazine (A in the table), lecithin: 5% by weight, 89% by weight of heavy white oil, 4% by weight of orcinol and 1% by weight of Triton X-100.
Was added and mixed to form an emulsion to obtain an emulsion.

Formulation Example 4 (Emulsion) Chemical herbicide, 2% by weight of atrazine (A in the table), lecithin: 5% by weight, 4-fold in 88% by weight of heavy white oil.
4% by weight of chloroorcinol and 1% by weight of Triton X-100 were added and mixed to form an emulsion to obtain an emulsion. In addition to the above formulation examples, formulations were similarly prepared for combinations of either orcinol or 4-chloroorcinol and each pesticide. The formulation is not limited to the above examples.

Test Example 1 Effect of the present invention, potency enhancer on various crops 1 / 3000a planter was filled with field soil, and crops such as corn, soybean, wheat, cotton, mustard, rice and beet, and several seeds Was sown and seedlings were raised until the 1-2 leaf stage. Various herbicides and orcinol were foliar-treated at the mixing ratios shown in Table 5 and cultivated in a greenhouse. One, two, and three weeks after application, the herbicidal effect was observed and evaluated in the following 6 stages of 0 to 5 and shown in Table 5 (Table 5).

5: All individuals died 4: Immediately withered 3: Strikingly suppressed growth 2: Suppressed growth 1: Slightly suppressed growth 0: Untreated equivalent In addition, 4 or more is the practical control level, and 1 or less is toxic tolerant The range was set.

[0039]

[Table 5]

Test Example 2 Synergistic Action of the Present Invention, Potency Enhancer A planter of 1 / 3000a was filled with field soil, and then, such as the pearl fir, morning glory, Western species Datura, chickweed, white locust, white locust, hibiscus, blue millet, edible millet, green locust, and crabgrass. , Several seeds were sown from crops such as corn, soybean, wheat, cotton, mustard, rice and beet, and weeds, and seedlings were raised up to the 1-2 leaf stage. Various herbicides and orcinol were treated at the mixing ratios shown in Table 6 and grown in a greenhouse. One, two, and three weeks after application, the herbicidal effect was observed and evaluated in 6 stages of 0 to 5 shown in Test Example 1, and shown in Table 6 (Tables 6 and 7) and Table 7 (Table 8).

[0041]

[Table 6]

[0042]

[Table 7]

[0043]

[Table 8]

Test Example 3 Synergistic herbicidal action of the potency enhancer of the present invention and atrazine-1-1 / 3000a planters were filled with upland soil, and the moss, morning glory, western pearl hemlock, chickweed, white locust, velvetleaf, yellowfin millet. Several seeds were sown from crops such as edible millet, green locust, corngrass, corn, soybean, wheat, cotton, mustard, rice and beet, and weeds, and seedlings were raised up to the 1-2 leaf stage. Various herbicides and orcinol were treated at the mixing ratios shown in Table 8 (Table 9),
It was cultivated in a greenhouse. One, two, and three weeks after application, the herbicidal effect was observed and evaluated in 6 stages of 0 to 5 shown in Test Example 1 and shown in Table 8 (Table 9).

[0045]

[Table 9]

Test Example 4 Synergistic Herbicidal Action of the Present Invention, Potency Enhancer and Atrazine-2-1 / 3000a planters were filled with field soil, and morning glory, chickweed, velvetleaf, yellowfin millet, corn crops,
Several kinds of seeds were sown from the weeds, and seedlings were raised until the 1-2 leaf stage. Various herbicides and orcinol are listed in Table 9 (Table 1
It was treated at the mixing ratio shown in 0) and cultivated in a greenhouse. The herbicidal effect is shown in Test Example 1 after 1, 2 and 3 weeks from application.
Observation evaluation was carried out in 6 stages of 5 and summarized in Table 9 (Table 10) and FIG. The synergistic effect on morning glory was shown in Fig. 3. The herbicidal value of both atrazine and orcinol at a given concentration should theoretically be indicated by a thick solid line, but is indicated by a thin line. The measured value showed more synergistic effect than expected, and the morning glory was killed.

[0047]

[Table 10]

Test Example 5 Synergistic Herbicidal Action of Choletotricum Tabacum Extract Extract and Various Herbicides 1 / 3000a planters were filled with field soil, and morning glory, chickweed, velvetleaf, yellowtail, corn crops,
Several kinds of seeds were sown from the weeds, and seedlings were raised until the 1-2 leaf stage. Various herbicides and extracts of choletricum tabacum were treated at the mixing ratios shown in Table 10 (Table 11) and Table 11 (Table 12), and cultivated in a greenhouse. After application 1,
After 2-3 weeks, the herbicidal effect was observed and evaluated in 6 stages of 0 to 5 shown in Test Example 1, and shown in Table 10 (Table 11) and Table 11 (Table 12).

[0049]

[Table 11]

[0050]

[Table 12]

From the above Test Examples 1 to 5, the following is clear. 1) The present invention and the efficacy enhancer are safe for various crops,
The selectivity depends on the herbicide used. 2) Depending on the herbicide used, the efficacy enhancing effect is large or small. 3) It has a potentiating effect on a wide range of herbicides.

[0052]

EFFECTS OF THE INVENTION The agrochemical potency enhancer according to the present invention shows a remarkable synergistic effect on herbicides without affecting crops, and reduces the application amount of these organic synthetic agrochemicals. It has become possible. This is advantageous for producers in terms of the possibility of reducing production costs, and for farmers and consumers, safety is expected due to the effect of reducing the conventional pesticide usage.

The pesticidal potency enhancer according to the present invention is isolated from natural microorganisms, can be expected to be biodegradable in nature, and is free from the concern of environmental pollution which is a concern with organic synthetic pesticides. It's safe. Therefore, the agrochemical potency enhancer according to the present invention not only contributes to crop production, but also contributes to avoiding environmental pollution and the danger of new chemical substances, which have become problems in recent years.

[Brief description of drawings]

FIG. 1 is an IR spectrum of CT-1.

FIG. 2 is an IR spectrum of CT-4.

FIG. 3 is a diagram showing a synergistic effect on morning glory when atrazine and orcinol are mixed. The thin line shows the measured value, and the thick line shows the theoretical value.

Claims (5)

[Claims] 1. A filamentous fungus Choletotricum tabacum (Co
A herbicide potency enhancer, which comprises a metabolite of Lletotrichum tabacum). 2. A herbicide potency enhancer comprising orcinol and / or 4-chloroorcinol. 3. The filamentous fungus Choletotricum tabacum (Co
A herbicide comprising a metabolite of Lletotrichum tabacum) and a herbicide with an enhanced herbicidal effect. 4. A herbicide having an enhanced herbicidal effect, which comprises orcinol and / or 4-chloroorcinol and a herbicide. 5. Coletotricum Tabacum (Cole)
totrichutum tabacum) metabolite, orcinol and / or 4-chloroorcinol.