EP0228464A1 - Procede et compose microbiocide pour des plantes - Google Patents

Procede et compose microbiocide pour des plantes

Info

Publication number
EP0228464A1
EP0228464A1 EP86904660A EP86904660A EP0228464A1 EP 0228464 A1 EP0228464 A1 EP 0228464A1 EP 86904660 A EP86904660 A EP 86904660A EP 86904660 A EP86904660 A EP 86904660A EP 0228464 A1 EP0228464 A1 EP 0228464A1
Authority
EP
European Patent Office
Prior art keywords
plant
compound
plants
microbiocidal
organo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP86904660A
Other languages
German (de)
English (en)
Other versions
EP0228464A4 (fr
Inventor
Shirley Ann Schafer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AGRI-SHIELD Inc
Original Assignee
AGRI-SHIELD Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by AGRI-SHIELD Inc filed Critical AGRI-SHIELD Inc
Publication of EP0228464A1 publication Critical patent/EP0228464A1/fr
Publication of EP0228464A4 publication Critical patent/EP0228464A4/fr
Withdrawn legal-status Critical Current

Links

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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

  • the present invention relates to a microbiocidal method and compound for plants and more particularly a microbiocidal method and compound for protecting plants from infection by micro-organisms and for protecting plants from freezing due to the presence of ice nucleation- active bacteria.
  • Microbiocidal compounds of various chemical compositions have been used on plants to inhibit or kill microorganisms that have a detrimental effect on the plant These microorganisms include bacteria, yeasts and fungi.
  • conventional microbiocides have several drawbacks. Conventional microbiocides must be applied to the plant at frequent intervals because the compound is washed off the plant. This multiple application requirement is expensive because relatively large amounts of the compound must be used during the life of the plant. In addition, the labor required to apply the antimicrobial compounds is expensive.
  • Microbiocides that are used to treat fruits, vegetables and grains can be introduced into the food chain where they are eventually consumed by humans. As the concentration of these microbiocidal compounds increases in the food chain, the detrimental effect on humans and animals is increased.
  • the antimicrobial compounds currently available are often genus specific. A different chemical compound may be required to treat each genus of microorganism found on a plant. Each multiply-infected plant must
  • citrus canker bacterium Xanthomonas campestris pv citri
  • Xanthomonas campestris pv citri is an example of a
  • ice nucleation-active bacteria have been postulated to be responsible for frost injury to plants.
  • a short rapid decrease in temperature can destroy the newly developing buds or flowers when the sap within the plants freezes and ruptures cell walls.
  • the freezing point of the aqueous solution is lowered to less the -10°C.
  • ice nucleation-active bacteria such as Pseudomonas syringae
  • the bacteria provide nuclei for the formation of ice crystals which grow and spread rapidly throughout the cells of the plant, causing severe frost damage at temperatures as warm as - 2°C.
  • Another treatment for the reduction of ice nucleation-active bacteria is to treat the plant with an aqueous solution of Cu 2 (S0 4 ) 3 .
  • this treatment is effective in reducing the ice nucleation-active bacteria, the chemical is very water soluble and quickly washes off the plant to which it is applied. Thus, to be effective, the compound must be applied before each expected freeze. This is both labor intensive and is very expensive.
  • the plant microbiocidal compound of the present invention is an organo-silicon quaternary amine.
  • Organo-silicon quaternary amines have been used on many non-living surfaces and have been used in water to inhibit the growth of microorganisms. (See U.S. Pat. No. 3,730,701). However, it is believed that organo-silicon quaternary amines have heretofore never been
  • organo- silicon compounds can be safely applied to many classes of plants.
  • the plant microbiocidal compounds of the present invention are effective in killing or inhibiting a wide spectrum of microorganisms. These compounds covalently
  • the plant microbiocidal compound of the present invention effectively protects a plant from infection by a wide variety of microorganisms with only two to three applications of the organo-silicon compound per year.
  • the plant microbiocidal compound of the present invention is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)
  • the plant microbiocidal compounds of the present invention are applied to a plant in an aqueous mixture by any conventional means, such as by spraying. After the compound is applied to citrus trees, the trees are protected against infection by the X. campestris organism. Because 35 the plant microbiocidal compound of the present invention is covalently bound to the surface of the leaves, branches and other exposed parts of the a citrus tree, such as an orange tree, a single application of the compound will protect the entire orange tree.
  • the plant microbiocidal compound of the present invention is also effective against ice nucleation-active bacteria such as Pseudomonas syringae and Erwinia herbicola.
  • ice nucleation-active bacteria such as Pseudomonas syringae and Erwinia herbicola.
  • the plant microbiocidal compound of the present invention is an organo-silicon quaternary amine having the following structure:
  • Y is an anion selected from the group consisting of chlorine, bromine, fluorine and iodine; " is a methyl radical or an aliphatic hydrocarbon radical of from 11 to 22 carbon atoms;
  • R' is a divalent hydrocarbon radical of 1 to 10 carbon atoms
  • R is a monovalent hydrocarbon radical of 1 to 6 carbon atoms or the CF 3 CH 2 CH 2 — radical; n is an integer from 0 to 2; and a is an integer from 1 to 2.
  • Another object of the present invention is to provide an improved microbiocidal compound for plants. Another object of the present invention is to provide a microbiocidal compound for plants which will remain on the plant for a long period of time after a single application.
  • Still another object of the present invention is to provide a microbiocidal compound for plants which is effective against Pseudomonas syringae.
  • Another another object of the present invention is to provide a microbiocidal compound that is effective in protecting seeds against micro ⁇ organisms.
  • Still another object of the present invention is to provide a microbiocidal compound for plants which is effective against Xanthomonas campestris.
  • the plant microbiocidal compound of the present invention is an organo-silicon quaternary amine compound with the following structure:
  • Y is an anion selected from the group consisting of chlorine, bromine, fluorine and iodine;
  • R" is a methyl radical or an aliphatic hydrocarbon radical of from 11 to 22 carbon atoms
  • R is a divalent hydrocarbon radical of 1 to 10 carbon atoms
  • R is a monovalent hydrocarbon radical of 1 to 6 carbon atoms or the CF 3 CH 2 CH 2 — radical; n is an integer from 0 to 2; and a is an. integer from 1 to 2.
  • R 3 is an alkyl group having from 8 to 18 carbon atoms
  • X is an anion selected from the group consisting of chlorine, bromine, fluorine and iodine.
  • organo-silicon quaternary amine shown above is commercially available as Dow Coming 5772 Antimicrobial Agent (Dow Coming, Midland, MI).
  • the plant microbiocidal compound of the present invention is preferrably applied to plants as an aqueous solution.
  • concentration of the organo-silicon quaternary amine in an aqueous solution is between approximately 0.05% to 5.0% by weight with a preferable concentration of between approximately 0.1% and 2% by weight.
  • the plant microbiocidal compound of the present invention can be applied to a plant by conventional techniques, such as by spraying or by fogging.
  • the plant microbiocidal compound of the present invention can also be painted on a plant
  • a surfactant can be optionally added to an aqueous mixture of the plant microbiocidal compound of the present invention to improve the spreading of the plant microbiocidal compound over the surface of the plant. Addition of a surfactant causes the plant microbiocidal compound of the present invention to be uniformly distributed over the plant surface.
  • a surfactant which can be used with the plant microbiocidal compound of the present invention is a nonionic surfactant and wetting agent comprising alkyl aryl polyalkoxynate alcohol available as Amway All Purpose Spray Adjuvant ( Amway Corp., Ada, MI).
  • organo-silicon quaternary amine compound was tested for phytotoxicity against Citrus mitis trees.
  • the aqueous solution was prepared by adding the appropriate amount of the stock solution of the organo-silicon plant microbiocidal compound of the present invention (Dow Chemical Company, Midland MI) to water and thoroughly mixing the compound until it was unifo ⁇ nly distributed throughout the aqueous solution.
  • the organo-silicon plant microbiocidal compound of the present invention Dow Chemical Company, Midland MI
  • Three citrus mitis trees were purchased from The Golden Stem Florist and Plants in Atlanta, GA. Each tree was trimmed and lightly sprayed with tap water to wash any substances from the leaves. The trees were allowed to air dry before application of the organo-silicon compound.
  • a 25 ml of the plant microbiocidal compound of the present invention is poured on the soil around the plant -
  • This test showed eradication of the citris canker bacterium (Xanthomonas campestris pv. citri) from artificially inoculated test surfaces.
  • the plant microbiocidal compound from Example I was applied to several surfaces.
  • the surfaces used were kraft paper, which represents a porous inanimate surface, and unwashed Orlando tangelos to test sanitizing capability on a citrus fruit surface.
  • Inoculum concentration was 10 6 cells/ml in water, which is approximately the highest concentration of citrus canker organisms that can be expected to be found exuding from the natural lesions.
  • the bacterial inoculum was not washed.
  • the bacterial cells carry their natural extracellular polysaccharide layers. This extracellular polysaccharide may play a protective role against conventional microbiocidal agents. Since citrus canker bacteria are sensitive to drying, the inoculum was applied to the treated test surface and allowed to remain for 10 minutes while in a humid chamber.
  • test surfaces were swabbed with sterile cotton swabs and streaked out on nutrient agar. Untreated controls were also tested. In each test, the test surface was replicated three times. The percent kill figures are the mean of the three replicate experiments. A sterile water rinse was applied to the 1 surface of the fruits and checked for surviving X. campestris cells by transferring a small amount on a sterile cotton swab to nutrient agar. The results of this test are shown in Table B.
  • the 5% solution of the plant microbiocidal compound of the present invention is capable of killing all of the X. campestris both on the kraft paper and on the fruit
  • the plant microbiocidal compound from Example 1 was tested against the early peanut leaf spot fungus.
  • Formulations of the plant microbiocidal compound from Example I were applied to peanut plants grown in the greenhouse at the Coastal Plain Experimental Station, Tifton, GA. Three 0 peanut plants per group were sprayed one time according to the following schedule.
  • Peanut plants were sprayed with the formulation specified and are then - covered with plastic bags for 36 hours. The plants were then uncovered and allowed to remain in the normal greenhouse environment for the remainder of the experiment. Three peanut plants per group were sprayed one 0 time with a formulation of the plant microbiocidal compound from Example 1, allowed to dry, and then infected with the fungus Cercospora arachidicola. The infected plants were then covered with a plastic bag for 36 hours, uncovered and allowed to remain under greenhouse conditions for the duration of the experiment The results of the test are shown in Table C. 5
  • the formulation was highly effective in controlling the C. arachidicola infection at concentrations between 0.1% and 0.5% when compared to the control (no treatment with plant microbiocidal compound). In addition, there was very little phytotoxicity at concentrations of 0.5% and 0.1%.
  • Example V The following organo-silicon quaternary amine compound (Dow Coming, Midland, MI) was tested for microbiocidal activity against Xanthomonas campestris pv. citri. '
  • the plant microbiocidal compound was applied to several surfaces.
  • the surfaces used were kraft paper, which represents a porous inanimate surface, and unwashed Orlando tangelos to test sanitizing capability on a citrus fruit surface.
  • Inoculum concentration was 10 6 cells/ml in water This is approximately the highest concentration of citrus canker organisms that can be expected'to be found exuding from the natural lesions.
  • Bacterial inoculum was not washed.
  • the bacterial cells carry their natural extracellular polysaccharide layers. This extracellular polysaccharide may play a protective role against conventional microbiocidal agents. Since citrus canker bacteria are sensitive to drying, the inoculum was applied to the treated test surface and allowed to remain for 10 minutes while in a humid chamber.
  • test surfaces were swabbed with sterile cotton swabs and streaked out on nutrient agar. Untreated controls were also tested. In each test, the test surface was replicated three times. A sterile water rinse was applied to the surface of the fruits and checked for surviving X. campestris cells by transferring a small amount on a sterile cotton swab to nutrient agar.
  • a 1% aqueous solution of the plant microbiocdal compound of the present invention was found to kill greater than 99% of the X. campestris cells on both kraft paper and on the fruit surface..
  • the phytotoxicity of the plant microbiocidal compound of the present invention was tested on several species of plants.
  • the organo-silicon quaternary amine from Example I was applied at a concentration of 0.1 and

Landscapes

  • 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

Procédé et composé microbiocides à l'organo-silicium pour des plantes. Le composé microbiocide organo-silicique peut être mélangé à de l'eau et appliqué à une plante pour tuer ou inhiber une grande variété de micro-organismes. Ce procédé et ce composé microbiocides pour des plantes sont très efficaces pour combattre une grande variété de micro-organismes pathogènes, notamment la bactérie Xanthomonas campestris, à l'origine du chancre des agrumes, et les bactéries formant des noyaux de glace telles que Pseudomonas syringe et Erwinia herbicola. En outre, ce composé microbiocide est également efficace contre des champignons tels que les champignons à l'origine des taches blanches des feuilles d'arachides (Cercospora arachidicola).
EP19860904660 1985-07-09 1986-07-09 Procede et compose microbiocide pour des plantes. Withdrawn EP0228464A4 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US75325185A 1985-07-09 1985-07-09
US753251 1985-07-09
US87876086A 1986-07-02 1986-07-02
US878760 1986-07-02

Publications (2)

Publication Number Publication Date
EP0228464A1 true EP0228464A1 (fr) 1987-07-15
EP0228464A4 EP0228464A4 (fr) 1989-07-26

Family

ID=27115718

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19860904660 Withdrawn EP0228464A4 (fr) 1985-07-09 1986-07-09 Procede et compose microbiocide pour des plantes.

Country Status (10)

Country Link
EP (1) EP0228464A4 (fr)
BR (1) BR8606761A (fr)
DK (1) DK92487A (fr)
ES (1) ES2000656A6 (fr)
FI (1) FI870978A0 (fr)
GR (1) GR861797B (fr)
HU (1) HUT42293A (fr)
OA (1) OA08497A (fr)
PT (1) PT82952B (fr)
WO (1) WO1987000006A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2308308A1 (fr) 2006-12-14 2011-04-13 Church & Dwight Co., Inc. Solutions aqueuses stables de composés ammonium quaternaire silane

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3836757A1 (de) * 1988-10-28 1990-05-03 Basf Ag Verfahren und produkte fuer den protektiven pflanzenschutz
US9089138B2 (en) * 2007-03-07 2015-07-28 Thomas L. Higgins Organosilane-nonionic water stable quaternary ammonium compositions and methods
GB201108806D0 (en) * 2011-05-25 2011-07-06 Arcis Biotechnology Ltd Plant treatment method
CN105153140A (zh) * 2015-11-02 2015-12-16 许自协 一种抑制柑橘溃疡病菌生长的化合物
KR102443950B1 (ko) * 2020-03-11 2022-09-16 전재욱 병해충 예방 기능의 작물 보호제 및 이를 이용한 작물의 병해충 방제 방법
CN112568036B (zh) * 2020-12-10 2023-07-11 四川尚毅农业开发有限公司 猕猴桃溃疡病的防治方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169949A (en) * 1973-02-28 1979-10-02 Rohm And Haas Company Isothiazolidin-3-ones
JPS6048908B2 (ja) * 1981-09-17 1985-10-30 富士通株式会社 密着形イメ−ジセンサ

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No relevant documents have been disclosed. *
See also references of WO8700006A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2308308A1 (fr) 2006-12-14 2011-04-13 Church & Dwight Co., Inc. Solutions aqueuses stables de composés ammonium quaternaire silane

Also Published As

Publication number Publication date
PT82952A (en) 1986-08-01
EP0228464A4 (fr) 1989-07-26
WO1987000006A1 (fr) 1987-01-15
OA08497A (en) 1988-07-29
GR861797B (en) 1986-11-11
DK92487D0 (da) 1987-02-24
HUT42293A (en) 1987-07-28
BR8606761A (pt) 1987-10-13
FI870978A (fi) 1987-03-05
FI870978A0 (fi) 1987-03-05
DK92487A (da) 1987-02-24
PT82952B (pt) 1989-01-30
ES2000656A6 (es) 1988-03-16

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