EP0228464A4 - PROCESS AND MICROBIOCIDAL COMPOUND FOR PLANTS. - Google Patents
PROCESS AND MICROBIOCIDAL COMPOUND FOR PLANTS.Info
- Publication number
- EP0228464A4 EP0228464A4 EP19860904660 EP86904660A EP0228464A4 EP 0228464 A4 EP0228464 A4 EP 0228464A4 EP 19860904660 EP19860904660 EP 19860904660 EP 86904660 A EP86904660 A EP 86904660A EP 0228464 A4 EP0228464 A4 EP 0228464A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- plant
- compound
- organo
- microbiocidal
- plants
- 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- Withdrawn
Links
- 230000003641 microbiacidal effect Effects 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title abstract description 66
- 244000005700 microbiome Species 0.000 claims abstract description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 19
- 239000010703 silicon Substances 0.000 claims description 19
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 3
- 229920000053 polysorbate 80 Polymers 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 5
- 229940051841 polyoxyethylene ether Drugs 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 23
- 241000894006 Bacteria Species 0.000 abstract description 18
- 235000020971 citrus fruits Nutrition 0.000 abstract description 13
- 241000207199 Citrus Species 0.000 abstract description 11
- 241000589636 Xanthomonas campestris Species 0.000 abstract description 9
- 150000003961 organosilicon compounds Chemical class 0.000 abstract description 6
- 241000233866 Fungi Species 0.000 abstract description 4
- 241000589615 Pseudomonas syringae Species 0.000 abstract description 4
- 241000315044 Passalora arachidicola Species 0.000 abstract description 3
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 2
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 2
- 241000588912 Pantoea agglomerans Species 0.000 abstract description 2
- 235000020232 peanut Nutrition 0.000 abstract description 2
- 241001553178 Arachis glabrata Species 0.000 abstract 1
- 230000006910 ice nucleation Effects 0.000 abstract 1
- 244000000010 microbial pathogen Species 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 14
- 235000013399 edible fruits Nutrition 0.000 description 13
- 150000001412 amines Chemical group 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 231100000674 Phytotoxicity Toxicity 0.000 description 7
- 239000002054 inoculum Substances 0.000 description 6
- 244000105624 Arachis hypogaea Species 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 150000004676 glycans Chemical class 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000002655 kraft paper Substances 0.000 description 4
- 239000006916 nutrient agar Substances 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 244000144730 Amygdalus persica Species 0.000 description 2
- 244000007645 Citrus mitis Species 0.000 description 2
- 235000007438 Citrus mitis Nutrition 0.000 description 2
- 241000333459 Citrus x tangelo Species 0.000 description 2
- 240000008669 Hedera helix Species 0.000 description 2
- 241000589655 Xanthomonas citri Species 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000000805 cytoplasm Anatomy 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011012 sanitization Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 235000011446 Amygdalus persica Nutrition 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000816 effect on animals Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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)
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 EP0228464A1 (en) | 1987-07-15 |
| EP0228464A4 true EP0228464A4 (en) | 1989-07-26 |
Family
ID=27115718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19860904660 Withdrawn EP0228464A4 (en) | 1985-07-09 | 1986-07-09 | PROCESS AND MICROBIOCIDAL COMPOUND FOR PLANTS. |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0228464A4 (fi) |
| BR (1) | BR8606761A (fi) |
| DK (1) | DK92487A (fi) |
| ES (1) | ES2000656A6 (fi) |
| FI (1) | FI870978A0 (fi) |
| GR (1) | GR861797B (fi) |
| HU (1) | HUT42293A (fi) |
| OA (1) | OA08497A (fi) |
| PT (1) | PT82952B (fi) |
| WO (1) | WO1987000006A1 (fi) |
Families Citing this family (7)
| 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 |
| EP2107948A4 (en) | 2006-12-14 | 2010-08-04 | Church & Dwight Co Inc | AQUEOUS STABLE SOLUTIONS OF SILANE QUATERNARY AMMONIUM COMPOUNDS |
| WO2008109775A1 (en) * | 2007-03-07 | 2008-09-12 | Higgins Thomas L | 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)
| 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 |
-
1986
- 1986-07-09 BR BR86067612A patent/BR8606761A/pt unknown
- 1986-07-09 WO PCT/US1986/001457 patent/WO1987000006A1/en not_active Application Discontinuation
- 1986-07-09 PT PT82952A patent/PT82952B/pt not_active IP Right Cessation
- 1986-07-09 GR GR861797A patent/GR861797B/el unknown
- 1986-07-09 ES ES8600214A patent/ES2000656A6/es not_active Expired
- 1986-07-09 EP EP19860904660 patent/EP0228464A4/en not_active Withdrawn
- 1986-07-09 HU HU863556A patent/HUT42293A/hu unknown
-
1987
- 1987-02-24 DK DK092487A patent/DK92487A/da not_active Application Discontinuation
- 1987-03-05 OA OA59080A patent/OA08497A/xx unknown
- 1987-03-05 FI FI870978A patent/FI870978A0/fi not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| No relevant documents have been disclosed. * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK92487D0 (da) | 1987-02-24 |
| OA08497A (en) | 1988-07-29 |
| FI870978L (fi) | 1987-03-05 |
| HUT42293A (en) | 1987-07-28 |
| ES2000656A6 (es) | 1988-03-16 |
| PT82952B (pt) | 1989-01-30 |
| DK92487A (da) | 1987-02-24 |
| PT82952A (en) | 1986-08-01 |
| FI870978A0 (fi) | 1987-03-05 |
| WO1987000006A1 (en) | 1987-01-15 |
| GR861797B (en) | 1986-11-11 |
| EP0228464A1 (en) | 1987-07-15 |
| BR8606761A (pt) | 1987-10-13 |
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