WO1992020226A1 - Composition a usage agricole pour lutter contre les maladies provoquees par les actinomycetes - Google Patents

Composition a usage agricole pour lutter contre les maladies provoquees par les actinomycetes Download PDF

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Publication number
WO1992020226A1
WO1992020226A1 PCT/JP1992/000661 JP9200661W WO9220226A1 WO 1992020226 A1 WO1992020226 A1 WO 1992020226A1 JP 9200661 W JP9200661 W JP 9200661W WO 9220226 A1 WO9220226 A1 WO 9220226A1
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WIPO (PCT)
Prior art keywords
sample
actinomycetes
soil
composition
ether
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PCT/JP1992/000661
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English (en)
Japanese (ja)
Inventor
Naoki Akiyama
Tadao Hasegawa
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Mitsubishikasei Polytec Co.
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Publication date
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Publication of WO1992020226A1 publication Critical patent/WO1992020226A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur

Definitions

  • the present invention relates to an agricultural composition for controlling disease caused by actinomycetes, such as scab, which is caused by Masaru, sweet potato, sugar beet, radish, ginseng and the like and causes great damage.
  • the scab disease caused by actinomycetes is caused by horse bell, sweet potato, sugar beet, radish, carrot, etc. and causes great damage.
  • actinomycetes when the scab is infected, raised spots are formed on the surface of the tuber, which gradually expands and the surface becomes rough and rigid, giving a scab. For this reason, not only does the appearance become unsightly, the commercial value is reduced, but also the potatoes that have been infected with scabs have a reduced starch content. Give a big blow.
  • seeds such as potatoes are immersed in a mixture of an antibiotic such as streptomycin and a copper wettable powder, or immersed in a PCNB agent. Have been disinfected.
  • an antibiotic such as streptomycin and a copper wettable powder
  • a PCNB agent such as a copper wettable powder
  • the soil where scabs have developed is generally fumigated with Kokulpicrin.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide an agent effective against plant diseases caused by actinomycetes represented by scabs.
  • an object of the present invention is to provide an agent effective against plant diseases caused by actinomycetes represented by scabs.
  • R!, R 2, R 3 and R 4 are hydrogen or Chokukusaria Rui branched alkyl group having a carbon. 1 to 3, A is linear or branched chain alkyl group having from 1 to 6 carbon, n represents 0 An integer from 5 to 5)
  • the present invention relates to an agricultural composition for controlling a disease caused by actinomycetes, which comprises one or more selected from the group as an active ingredient.
  • General formula which is a raw material of the polymer or copolymer which is the active ingredient of the present invention
  • R j, R 2 , R. and R 4 are hydrogen or a linear or branched alkyl group having 1 to 3 carbon atoms, A is a linear or branched alkyl group having 1 to 6 carbon atoms, and n is 0 An integer from 5 to 5)
  • the epihalohydrin which reacts with the amine is represented by the general formula:
  • halogen may be any of fluorine, chlorine, bromine and iodine, but is preferably epichlorohydrin for economic reasons.
  • alkylene dihalide a general formula
  • dichloroethane Specifically, dichloroethane, dichloroprononone, dichlorobutane, dichlorohexane, dibromoethane, and promochloroproha.
  • Dibromopropane Dibutenemohexane, dichlorononane and the like.
  • 1,3-dichloropropane are preferred due to their reactivity with amines and economic reasons.
  • (D is absent, or a linear or branched alkylene group having 1 to 4 carbon atoms, or a group represented by one (CH 2 -0-CH 2 ) m , where m is 1 to 4)
  • the following are specifically used: 1,3-butadiene japoxide, 1,4-pentadiene japoxide, 1,5-hexadienpoxide, 1,6 — ⁇ Butadiene japoxide, 1,7-year-old kuta jenpoxide, ethylene glycol glycidyl ether, triethylene dalicydyl ether, etc.
  • the dihalogeno alkyl ether is represented by the general formula:
  • R 5 and R g are a linear or branched alkylene group having 1 to 4 carbon atoms, X is a halogen, and d is an integer of 1 to 12)
  • ⁇ 1, 2,2′—dichloroethyl ether, 2,2, dibromoethyl ether, 3,3, dichloromethyl propyl ether, 2,3-dichloro mouth propyl ether, 4,4'-dichlorobutyl ether, 4,4'-dibromobutylbutyl ether and the like.
  • the degree of polymerization is up to 10 Examples include dihalogenoethyl ether which can be obtained by a dehydration reaction or the like from an ethylene oxide polymer and an alkyl alcohol halide.
  • dichloroethyl ether 2,2, -dichloroethyl ether
  • dichloroethyl ether 2,2, -dichloroethyl ether
  • the above-mentioned ephalohydrin, alkylenedihalide, japoxide and dihalogenoalkyl ether may be used alone or in combination of two or more kinds for each component. In the case of mixing two or more kinds, there is no particular limitation as long as the sum of the number of moles of the mixture is substantially equal to the number of moles of the amide.
  • a closed type reaction vessel equipped with a stirrer was prepared by making the sum of the moles of one compound selected from the group consisting of the epoxides and dihalogenoalkyl ethers, or the sum of the moles of the mixture approximately equal to the moles of the amine.
  • the reaction is preferably performed under an inert gas atmosphere with the temperature inside the reaction vessel in the range of 30 to 100.
  • a 20 to 70% aqueous solution of the above-described amine is charged into a closed reaction vessel equipped with a stirrer, a reflux condenser, a thermometer, and the like, and the atmosphere in the vessel is replaced with nitrogen gas. Then, while stirring, the temperature in the reaction vessel is adjusted to a predetermined temperature, and a single compound selected from the group consisting of epihalohydrin, alkylenedihalide, gepoxide, and dihalogenoalkyl ether, or a mixture thereof is continuously fed. It may be added in a targeted or batch manner. However, 100% amine can be used as an amine. Water is mainly used as the reaction solvent, but methyl alcohol, ethyl alcohol or dimethylformamide may be used in consideration of the solubility of the raw materials and the reaction products.
  • the water-soluble polymer thus obtained is further processed to convert a halogen (derived from epihalohydrin, alkylenedihalide and dihalogenoalkyl ether) as a counterion into another anion, for example, may be used instead of so 4 — or remove counter ions
  • a halogen derived from epihalohydrin, alkylenedihalide and dihalogenoalkyl ether
  • the leverage polymer may be a hydroxide.
  • These water-soluble polymers can be made into a solid by removing the solvent (usually water), or can be produced as an aqueous solution as it is, or by diluting or concentrating as needed. Can also be used.
  • the alkyleneimine polymer has the general formula:
  • R 7 is an alkylene group, preferably a straight-chain or branched-chain alkylene group having 1 to 8 carbon atoms. A plurality of R 7 may be the same or different. The degree of polymerization of is shown.
  • a polymer represented by the formula is used, but these aldimylene polymers do not necessarily have to have a completely linear structure as shown in the above general formula, and may have a branch. No problem. Also, a quaternary salt of an alkyleneimine polymer obtained by adding hydrochloric acid or the like to the alkyleneimine polymer may be used.
  • alkyleneimine polymer examples include an ethyleneimine polymer, a propyleneimine polymer, a trimethyleneimine polymer, a tetramethyleneimine polymer, and a hexamethyleneimine polymer.
  • ethyleneimine polymer examples include an ethyleneimine polymer, a propyleneimine polymer, a trimethyleneimine polymer, a tetramethyleneimine polymer, and a hexamethyleneimine polymer.
  • polymers of ethyleneimine are particularly preferred for economic reasons. This is generally obtained by ring-opening polymerization using ethyleneimine and cation catalysts, but also other reactions such as the reaction of ethyleneimine with ethylenedihalide or ammonia, the condensation reaction of ethanolamine, etc. Can also be obtained.
  • the above amine reactant and alkyleneimine polymer are dissolved in 2 mol / ⁇ of KBr aqueous solution and measured and calculated.
  • the intrinsic viscosity at 25 ° C is calculated.
  • the magnitude of the molecular weight can be determined.
  • the limiting viscosity [7?] Is less than 1 Zg, preferably less than 0.6 dZg, more preferably less than 0.4 d, since the effect on actinomycetes is stronger in the lower molecular weight range.
  • ⁇ Z g or less is desirable, but is not particularly limited to that range.
  • the active ingredient of the present invention can be used not only in each of the above polymers but also in a copolymer. That is, a copolymer obtained by reacting at least one compound selected from the group consisting of ephalohydrin, alkylenedihalide, epoxide, and dihalogenoalkyl ether with an amine represented by the above general formula, alkylene imide It may be a copolymer, or a copolymer of the above-mentioned polymer or the above-mentioned copolymer and the above-mentioned alkylene imide polymer.
  • the active ingredient of the present invention When cultivating a crop susceptible to actinomycetes, such as potato, such as potato, the active ingredient of the present invention alone or in the soil at an appropriate time from 1 to 2 months before the planting of the crop and immediately before planting.
  • the mixture is diluted with water and other solvents to 110-: LZ 100,000 Diluted as it is, or mixed with other pesticides, fertilizers, etc., and sprayed or dropped Mix.
  • the application rate of the present composition is preferably 0.2 to 20 kg per 10 ares, but is not limited to this range.
  • the aqueous solution of the composition When spraying on soil, the aqueous solution of the composition is mixed relatively thickly with the soil itself, or absorbed into formic lime, calcium carbonate, chemical fertilizer, and other inorganic diatomaceous earth zeolites. After that, there is a method of mixing with the cultivation soil.
  • the seeds or seed potatoes of the crop are immersed or applied to a solution obtained by diluting the active ingredient of the present invention to 1Z10 to 1Z10,000 with a solvent such as water, or a mixture thereof with other pesticides. Then, bringing the seeds and the like into sufficient contact with the drug is also effective in preventing the disease.
  • the use ratio of the present composition in soil admixture or seed disinfection is not limited to a limited range, but a small amount has a sufficient effect, so that a use amount of about 1/50 to 1Z1000 is appropriate.
  • composition of the present invention When the composition of the present invention is applied in this manner, plant scabs and other plant diseases caused by actinomycetes can be easily suppressed, and the yield of crops increases. In addition, since it is not necessary to cultivate under conditions that are not suitable for cultivation (pH, etc.) in order to avoid disease as in the past, the yield can be increased in this respect, and continuous cultivation is possible. .
  • composition of the present invention can be said to be completely breakthrough against diseases caused by actinomycetes.o
  • the present invention also has the following effects, and is extremely high in practical value.
  • composition of the present invention is substantially non-volatile, there is no need to pay attention to the surrounding safety when using the composition.
  • composition of the present invention has no effect on the germination rate, leaf bud rate, etc. of the crop, and has no adverse effects on cultivation.
  • composition of the present invention is extremely safe, non-irritating to warm-blooded animals, and extremely simple to use.
  • composition of the present invention is substantially harmful to useful soil microorganisms. As it does not lose the balance of soil microorganisms, crops can be grown using normal cultivation methods.
  • the active ingredient of the composition of the present invention was known as a settling accelerator or a flocculant, but such an effect on agricultural crops was completely unexpected.
  • composition of the present invention has been described for scabs occurring in crops such as potatoes such as potatoes, potatoes, radishes, and carrots.
  • Diseases caused by actinomycetes are not limited to scabs. Can be controlled.
  • Example 1 effects on actinomycetes Streptomyces (Streptomyces) and other microorganisms, in Example 2, results from pot tests, and in Example 3, experiments on experimental farms In Example 4, the effect of seed disinfection will be described.
  • a mixture of epichlorohydrin and propylene dichloride in a 40% aqueous solution of the amide mixture was maintained at a reaction temperature of 90 ° C until the molar ratio of the mixture of chlorides was almost 1: 1.
  • a 50% aqueous solution of a mixture of dimethylamine and ⁇ , ⁇ , ⁇ , ,, ⁇ , ⁇ -tetramethylethylenediamine prepared in a molar ratio of 1: 0.3 in advance, and a molar ratio of 0,5 : Ethylene glycol glycidyl ether and dichloroethyl ether in an aqueous mixed amine solution until the molar ratio of the mixture of ethylene glycol glycidyl ether and dichloroethyl ether prepared in the ratio of 1: 1 becomes approximately 1: 1.
  • the mixture was added while maintaining the reaction temperature at 70 ° C, and mixed by stirring.
  • the resulting mixed reaction composition (intrinsic viscosity [??] measured with a 2 mol / ⁇ KBr aqueous solution) was 0.33.
  • a 50% aqueous solution of a mixture of dimethylamine and N, N, N,, ⁇ , ⁇ , 1-tetramethylethylenediamine prepared in a molar ratio of 1: 0.3 in advance, and a molar ratio of 1: 1
  • the mixture of epichlorohydrin and propylene dichloride was added to the mixed amine aqueous solution while maintaining the reaction temperature at 80 ° C, and mixed by stirring.
  • a sample having a limiting viscosity force of 0.23 di / g measured with an aqueous KBr solution of the above) was diluted with water to obtain a sample having a purity of 50% by weight, which was designated as Sample D.
  • This sample A was sprayed and mixed on calcium carbonate for soil admixture, dried at 60 ° C, and a sample of this composition: calcium carbonate 1: 9 was prepared, and this sample F was obtained.
  • Streptomyces MAFF 03-01524 was obtained from the Agricultural and Biological Resources Institute, Ministry of Agriculture, Forestry and Forestry, and the bacteria were Staphylococcus aureus ATCC 6538 and Pseudodomo. Using Pseudomonas aeruginosa P2, the fungus Aureobas idium H 2627 and Candida albicans IF 01594, MIC (minimum inhibitory concentration) and MCC (minimum sterilization) in the medium Concentration) was measured.
  • Bacteria Pre-cultured in 5 m of SCD pros at 35 ° C. for 24 hours and adjusted to a bacterial count of about 10 6 / m 2 was used as a test bacterial solution.
  • Yeast GP broth 5 precultured for 48 hours at 3 5 ° C in m, prepared in as saline give a cell number 1 X 1 0 6 Zm, was tested bacterial solution.
  • Mold Potato dextroses were inoculated on slant medium and pre-cultured at 30 ° C for 10 days. Its slope to 0.0 5% preparative window I over emissions (Twe en) Put 8 0 saline, and adjusted to be spore number 1 XI 0 6 / m &, and a test bacterial solution.
  • MIC and MCC were measured by the liquid medium dilution method.
  • each test tube is inoculated with 0.1 ⁇ m of the test bacterial solution, cultured for 5 days at 25 ° C for actinomycetes, cultured for 48 hours at 35 ° C for bacteria and yeast, and for 7 days at 30 ° C for mold. After culturing, the MIC value was determined based on the minimum sample concentration in the test tube where no turbidity was visually observed.
  • Stapn lococcus MIC 750 1,500 3,000 1,500 1,500 ' ⁇ aureus MCC 1,500 3,000 3,000 3,000 3,000;
  • the pots were laid outdoors and grown, and 70 days after planting, the tubers were dug up and examined for tubers weighing about 15 g or more.
  • the diseased potatoes were also regarded as diseased potatoes, and the diseased potatoes were divided by the harvest amount, and the lesion area ratio (the disease area divided by the harvested potato amount) was determined.
  • the granular compound fertilizer and calcium carbonate (0. Triple mass%) were mixed to flare section of scab, and divided into 6 m 2, and the experimental group.
  • the experimental plots were divided into 1 to 21 plots, and three plots were randomly selected from the plots. The whole plot was designated as test plots 1 to 7, and the above three plots were tested under the same conditions.
  • Test zone 1 was used as a control, and the ridges were raised in the same manner as in the general cultivation method. .
  • test plot 2 sample A was diluted with water to make an aqueous solution with a pure content of 1Z200, and cultivated while spraying 720 g per plot, so that sample A was mixed with the soil. After three weeks, the ridges were raised and planted in the same manner as in Test Zone 1.
  • test plot 3 dilute sample A with water to make an aqueous solution with a pure content of 1Z200, plow it while spraying 144 g per plot, and mix sample A with soil. The test was performed in the same manner as in Test Zone 2.
  • Test plot 4 was the same as test plot 1. However, two weeks after planting, the aqueous solution used in the test area 2 was injected into a tube (insert the tube into the soil, and pour the aqueous solution near the place where the horse was planted by Masaru). The dose is 144 g.
  • test plot 5 sample D was diluted with water to make an aqueous solution with a pure content of 1Z200, and cultivated while spraying 720 g per plot in the test plot to mix sample D into the soil. After three weeks, the ridges were raised and planted in the same manner as in Test Zone 1.
  • test plot 6 900 g of sample F was added to the soil per test plot, mixed well, and after 3 weeks, the ridges were raised and planted in the same manner as test plot 1.
  • sample G was diluted with water to make an aqueous solution with a purity of 1200, and cultivated while spraying 720 g per plot to mix sample G in the soil. Same as 5.
  • the field was disinfected with chlorpicrin at a ratio of 30 / 10a, and each 6 m2'-division was divided into experimental plots.
  • test plot 17 plots The experimental plot is divided into 121 plots, and three plots are randomly selected from the plots, and the whole is designated as test plot 17 plots.
  • Test zone 1 was set as a control (target zone), and ridges were raised in the same manner as in the general cultivation method. In the plot, the so-called “harvest” was harvested from the field where scabs occurred and no lesions were visually observed. Potatoes (apparently healthy potatoes) (two types of Yutaka) were planted as seed potatoes.
  • test plot 2 the same potato as in test plot 1 which was immersed for about 3 seconds in 1 aqueous solution of sample A diluted to 1100 with water for 1 second after disinfection of seeds was used as seed potato. Planting was performed in the same manner as in test plot 1.
  • Test plots 3, 4, 5, 6, and 7 were performed in the same manner as test plot 2, except that samples B, C, D, E, and G were used for seed disinfection, respectively.
  • tubers were dug up, and the tuber weight of about 20 g or more, the total tuber count and the diseased tuber rate (disease of about 2 mm. (Divided by the yield) 3 ⁇ 4 ⁇
  • the composition of the present invention has an excellent control effect on the disease caused by actinomycetes on plants represented by scab, and is not as toxic as conventional drugs against scab. Since it is not volatile, it is highly safe to the surrounding environment and its application method is simple. Furthermore, it does not cause phytotoxicity to cultivated crops.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composition à usage agricole efficace contre les maladies végétales provoquées par les actinomycètes, et présentant une très grande sécurité pour l'environnement. Ladite composition renferme comme substance active au moins un élément sélectionné parmi les polymères suivant: (A) un polymère azoté hydrosoluble préparé par la réaction d'au moins un composé choisi dans le groupe constitué d'épihalohydrine, d'halogénure d'alkylène, de diépoxy et d'éther de dihalogénoalkyle, avec une amine représentée par la formule générale (I) où R1, R2, R3 et R4 représentent chacun hydrogène, alkyle linéaire C1 à C3 ou alkyle ramifié; A représente alkyle C1 à C6 linéaire ou ramifié; et n représente un entier de 0 à 5, B un polymère d'alkylène imine, et C un copolymère de ceux-ci
PCT/JP1992/000661 1991-05-24 1992-05-22 Composition a usage agricole pour lutter contre les maladies provoquees par les actinomycetes WO1992020226A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP12002391A JPH04346903A (ja) 1991-05-24 1991-05-24 放線菌による病害を防除する農業用組成物
JP3/120023 1991-05-24

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WO1992020226A1 true WO1992020226A1 (fr) 1992-11-26

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1002194C2 (nl) * 1995-01-31 1999-01-26 Mitsubishi Chem Corp Middel en werkwijze voor het bewaren van de versheid van snijbloemen.
WO1999012418A1 (fr) * 1997-09-08 1999-03-18 Basf Aktiengesellschaft UTILISATION COMME BIOCIDES DE POLYMERISATS CONTENANT DES UNITES β-HYDROXYALKYLVINYLAMINE

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4909518B2 (ja) * 2005-02-08 2012-04-04 日鉄環境エンジニアリング株式会社 連作障害の制御方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51138799A (en) * 1975-04-14 1976-11-30 Buckman Labor Inc Polymer composite constituted with amine and epichlorhydrine and process for preparing said composite
JPS6118750A (ja) * 1982-09-02 1986-01-27 バツクマン・ラボラトリ−ズ・インコ−ポレ−テツド イオネン型重合体
JPH02306905A (ja) * 1989-05-19 1990-12-20 Dow Corning Kk 繊維体用抗菌剤
JPH03186391A (ja) * 1989-12-14 1991-08-14 Mitsubishi Kasei Poritetsuku Kk スライムコントロール剤及びスライムコントロール方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51138799A (en) * 1975-04-14 1976-11-30 Buckman Labor Inc Polymer composite constituted with amine and epichlorhydrine and process for preparing said composite
JPS6118750A (ja) * 1982-09-02 1986-01-27 バツクマン・ラボラトリ−ズ・インコ−ポレ−テツド イオネン型重合体
JPH02306905A (ja) * 1989-05-19 1990-12-20 Dow Corning Kk 繊維体用抗菌剤
JPH03186391A (ja) * 1989-12-14 1991-08-14 Mitsubishi Kasei Poritetsuku Kk スライムコントロール剤及びスライムコントロール方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1002194C2 (nl) * 1995-01-31 1999-01-26 Mitsubishi Chem Corp Middel en werkwijze voor het bewaren van de versheid van snijbloemen.
WO1999012418A1 (fr) * 1997-09-08 1999-03-18 Basf Aktiengesellschaft UTILISATION COMME BIOCIDES DE POLYMERISATS CONTENANT DES UNITES β-HYDROXYALKYLVINYLAMINE
US6214885B1 (en) 1997-09-08 2001-04-10 Basf Aktiengesellschaft Use of polymers containing β-hydroxyalkylvinylamine units as biocides

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