CA1171426A - Copper complexes, their preparation, their use in controlling plant pests, and agents for such control - Google Patents
Copper complexes, their preparation, their use in controlling plant pests, and agents for such controlInfo
- Publication number
- CA1171426A CA1171426A CA000375391A CA375391A CA1171426A CA 1171426 A CA1171426 A CA 1171426A CA 000375391 A CA000375391 A CA 000375391A CA 375391 A CA375391 A CA 375391A CA 1171426 A CA1171426 A CA 1171426A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- water
- solution
- copper
- acid
- 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.)
- Expired
Links
- 150000001879 copper Chemical class 0.000 title description 10
- 239000003795 chemical substances by application Substances 0.000 title description 5
- 241000607479 Yersinia pestis Species 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 25
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052802 copper Inorganic materials 0.000 claims abstract description 23
- 239000010949 copper Substances 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005396 acrylic acid ester group Chemical group 0.000 claims abstract description 5
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims abstract description 4
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims description 19
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- -1 copper amine salt Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 66
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 24
- 235000011114 ammonium hydroxide Nutrition 0.000 description 24
- 229960000510 ammonia Drugs 0.000 description 21
- 229910021529 ammonia Inorganic materials 0.000 description 21
- 238000001035 drying Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 239000011814 protection agent Substances 0.000 description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
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- 239000006185 dispersion Substances 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 239000005749 Copper compound Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
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- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
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- 240000008790 Musa x paradisiaca Species 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 240000003768 Solanum lycopersicum Species 0.000 description 2
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- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
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- 235000011037 adipic acid Nutrition 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 235000021015 bananas Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
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- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- QWCXWGSRBNHCAB-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate;3-oxobutanoic acid Chemical compound CC(=O)CC(O)=O.OCCCOC(=O)C=C QWCXWGSRBNHCAB-UHFFFAOYSA-N 0.000 description 1
- WZISPVCKWGNITO-UHFFFAOYSA-N 4-(diethylamino)-2-methylidenebutanamide Chemical compound CCN(CC)CCC(=C)C(N)=O WZISPVCKWGNITO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241001464977 Clavibacter michiganensis subsp. michiganensis Species 0.000 description 1
- 239000005752 Copper oxychloride Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
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- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 241001661371 Exobasidium vexans Species 0.000 description 1
- 241001181532 Hemileia vastatrix Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
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- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000588701 Pectobacterium carotovorum Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 241000521936 Pseudomonas amygdali pv. lachrymans Species 0.000 description 1
- 241000589613 Pseudomonas savastanoi pv. phaseolicola Species 0.000 description 1
- 241000589615 Pseudomonas syringae Species 0.000 description 1
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- 241000589771 Ralstonia solanacearum Species 0.000 description 1
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- 241000228452 Venturia inaequalis Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000589636 Xanthomonas campestris Species 0.000 description 1
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- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940048053 acrylate Drugs 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
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- 239000003630 growth substance Substances 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010912 leaf Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/145—Maleic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3017123.4 | 1980-05-03 | ||
| DE19803017123 DE3017123A1 (de) | 1980-05-03 | 1980-05-03 | Fungizid |
| DE19803022432 DE3022432A1 (de) | 1980-06-14 | 1980-06-14 | Fungizid |
| DEP3022432.9 | 1980-06-14 | ||
| DEP3039409.3 | 1980-10-18 | ||
| DE19803039409 DE3039409A1 (de) | 1980-10-18 | 1980-10-18 | Mittel zur bekaempfung von pflanzenbakteriosen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171426A true CA1171426A (en) | 1984-07-24 |
Family
ID=27188610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375391A Expired CA1171426A (en) | 1980-05-03 | 1981-04-14 | Copper complexes, their preparation, their use in controlling plant pests, and agents for such control |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4409358A (en, 2012) |
| EP (1) | EP0039788B1 (en, 2012) |
| AU (1) | AU538632B2 (en, 2012) |
| BR (1) | BR8102689A (en, 2012) |
| CA (1) | CA1171426A (en, 2012) |
| DE (1) | DE3161008D1 (en, 2012) |
| DK (1) | DK160910C (en, 2012) |
| ES (1) | ES8300003A1 (en, 2012) |
| GB (1) | GB2077740B (en, 2012) |
| GR (1) | GR75196B (en, 2012) |
| IE (1) | IE51149B1 (en, 2012) |
| IL (1) | IL62645A (en, 2012) |
| KE (1) | KE3432A (en, 2012) |
| MA (1) | MA19132A1 (en, 2012) |
| MY (1) | MY8600469A (en, 2012) |
| PT (1) | PT72950B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI70682C (fi) * | 1984-06-20 | 1987-08-05 | Kemira Oy | Traeskyddsmedel och dess anvaendning som ytbehandlingsmedel. |
| US4851557A (en) * | 1985-06-20 | 1989-07-25 | Benckiser-Knapsack Gmbh | Copper-containing polymers, a process for their preparation and their use as fungicides |
| EP0208858B1 (de) * | 1985-06-20 | 1989-02-08 | Benckiser-Knapsack GmbH | Kupferhaltige Polymere, Verfahren zur ihrer Herstellung und ihre Anwendung als Fungizide |
| US5242685A (en) * | 1986-03-15 | 1993-09-07 | Basf Aktiengesellschaft | Copper-containing agent for controlling fungi and bacteria |
| DE3608681A1 (de) * | 1986-03-15 | 1987-09-17 | Basf Ag | Kupferhaltiges mittel zur bekaempfung von pilzen und bakterien |
| US4808407A (en) * | 1987-08-14 | 1989-02-28 | Mooney Chemicals, Inc. | Water-soluble copper salts |
| US6471976B1 (en) | 1990-10-01 | 2002-10-29 | Evelyn J. Taylor | Copper complex bactericide/fungicide and method of making same |
| CA2051716C (en) * | 1990-10-01 | 2002-05-14 | James H. Lefiles | Copper hydroxide dry flowable bactericide/fungicide and method of making and using same |
| ZA931681B (en) * | 1992-04-03 | 1993-12-07 | Griffin Corp | Copper complex bactericide/fungicide and method of making same |
| US5665679A (en) * | 1995-10-18 | 1997-09-09 | Griffin Corporation | Method of desiccating potato vines with copper alkylenediamine |
| EG22120A (en) * | 1999-11-02 | 2002-08-30 | Delta Agro Chemical | Fungicide formulations contain copper and their method for preparation |
| JP4599780B2 (ja) * | 2001-09-13 | 2010-12-15 | ダイキン工業株式会社 | 含フッ素アルコール化合物の製造用触媒及び含フッ素アルコールの製造方法 |
| AUPR809001A0 (en) * | 2001-10-04 | 2001-10-25 | Bioacumen Pty Limited | Compositions for the treatment and prevention of plant pathogens |
| AU2002331462B2 (en) * | 2001-10-04 | 2008-01-10 | Bioacumen Pty Limited | Compositions for the treatment and prevention of plant pathogens |
| TW200528030A (en) * | 2003-10-17 | 2005-09-01 | Basf Ag | Novel copper-containing formulations |
| DE10351004A1 (de) | 2003-10-30 | 2005-05-25 | Basf Ag | Nanopartikuläre Wirkstoffformulierungen |
| WO2006108835A2 (de) * | 2005-04-15 | 2006-10-19 | Basf Aktiengesellschaft | Verwendung von polylysin in kupferhaltigen bioziden formulierungen |
| MX2007012575A (es) * | 2005-04-18 | 2007-11-16 | Basf Ag | Preparacion que contiene por lo menos un fungicida conazolico. |
| ES2265280B1 (es) * | 2005-06-23 | 2008-03-16 | Universitat Jaume I | Aplicacion de acidos monocarboxilicos de cadena corta para la proteccion de plantas frente a estres biotico y abiotico. |
| EP1961306A4 (en) * | 2005-12-16 | 2012-03-28 | Riken | BACTERICIDE FOR USE IN AGRICULTURE AND GARDENING CONTAINING AN INORGANIC COPPER COMPOUND AS AN ACTIVE SUBSTANCE |
| US7497901B2 (en) | 2005-12-30 | 2009-03-03 | E. I. Dupont De Nemours And Company | Tungstate and molybate wood preservatives |
| US7462227B2 (en) * | 2005-12-30 | 2008-12-09 | E.I. Du Pont De Nemours And Company | Ibuprofen complexes as wood preservatives |
| US7427316B2 (en) * | 2005-12-30 | 2008-09-23 | E.I. Du Pont De Nemours And Company | Tropolone complexes as wood preservatives |
| US7540906B2 (en) * | 2005-12-30 | 2009-06-02 | E.I. Du Pont De Nemours & Company | Metal salts of hydrolyzed olefin/maleic anhydride copolymers and their use as wood preservatives |
| US8221796B2 (en) | 2006-04-25 | 2012-07-17 | Albaugh, Inc. | Copper-based fungicide/bactericide |
| US8192766B2 (en) * | 2006-04-25 | 2012-06-05 | Albaugh, Inc. | Copper-based fungicide/bactericide |
| US9474282B2 (en) * | 2013-12-13 | 2016-10-25 | Tony John Hall | Acid-solubilized copper-ammonium complexes and copper-zinc-ammonium complexes, compositions, preparations, methods, and uses |
| WO2015185994A1 (en) * | 2014-06-03 | 2015-12-10 | Myco Sciences Limited | Anti-microbial compositions, preparations, methods, and uses |
| MX2017015797A (es) | 2015-06-08 | 2018-11-09 | Myco Sciences Ltd | Composiciones antimicrobianas y agroquimicas. |
| WO2017112848A1 (en) | 2015-12-23 | 2017-06-29 | American Chemet Corporation | Methods for enhancing the preservation of cellulosic materials and cellulosic materials prepared thereby |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB599443A (en) * | 1945-06-01 | 1948-03-12 | Stevensons Dyers Ltd | A new or improved method of rot proofing textile materials |
| GB420533A (en) | 1932-06-02 | 1934-12-03 | Ig Farbenindustrie Ag | Manufacture of metal salts of polymeric carboxylic acids and the production of shaped articles therefrom |
| GB420589A (en) | 1933-06-01 | 1934-12-03 | Ig Farbenindustrie Ag | Manufacture of metal salts of polymeric carboxylic acids and the production of shaped articles therefrom |
| GB593416A (en) * | 1943-11-10 | 1947-10-16 | Nuodex Products Co Inc | Improvements in methods of preparing copper fungicide solutions |
| BE484394A (en, 2012) * | 1947-08-15 | |||
| FR1590623A (en, 2012) * | 1968-06-05 | 1970-04-20 | ||
| SE374686B (en, 2012) * | 1971-01-26 | 1975-03-17 | B O Heger | |
| GB1394990A (en) * | 1971-08-12 | 1975-05-21 | Hydrophilics Int Inc | Copolymers and compositions containing copolymers |
| US3842000A (en) | 1971-10-07 | 1974-10-15 | Battelle Development Corp | Process for removal of ammonia from aqueous streams |
| US3900504A (en) * | 1972-02-04 | 1975-08-19 | Mineral Research & Dev Corp | Cuprammonium acetate complex and method of preparing |
| US4020180A (en) * | 1972-02-04 | 1977-04-26 | Mineral Research & Development Corporation | Noncorrosive cuprammonia fungicide and method for using same |
| GB1587307A (en) * | 1977-03-04 | 1981-04-01 | Nitto Electric Ind Co | Antibacterial and antifungal material |
| GB1574939A (en) * | 1977-05-12 | 1980-09-10 | Cuprinol Ltd | Compositions containing preservative metals and their use for the preservation of wood and like materials and as fungicides |
| DE2807293A1 (de) * | 1978-02-21 | 1979-08-23 | Bp Chem Int Ltd | Homogenes, fluessiges, einen cuprammonium-komplex umfassendes praeparat |
| US4175090A (en) * | 1978-02-23 | 1979-11-20 | Bp Chemicals Limited | Chemical composition |
-
1981
- 1981-04-08 GR GR64628A patent/GR75196B/el unknown
- 1981-04-10 US US06/252,800 patent/US4409358A/en not_active Expired - Lifetime
- 1981-04-10 EP EP81102722A patent/EP0039788B1/de not_active Expired
- 1981-04-10 DE DE8181102722T patent/DE3161008D1/de not_active Expired
- 1981-04-14 CA CA000375391A patent/CA1171426A/en not_active Expired
- 1981-04-14 IL IL62645A patent/IL62645A/xx not_active IP Right Cessation
- 1981-04-23 GB GB8112616A patent/GB2077740B/en not_active Expired
- 1981-04-29 PT PT72950A patent/PT72950B/pt not_active IP Right Cessation
- 1981-04-29 MA MA19338A patent/MA19132A1/fr unknown
- 1981-04-29 IE IE950/81A patent/IE51149B1/en not_active IP Right Cessation
- 1981-04-30 BR BR8102689A patent/BR8102689A/pt not_active IP Right Cessation
- 1981-04-30 AU AU70015/81A patent/AU538632B2/en not_active Ceased
- 1981-04-30 ES ES501820A patent/ES8300003A1/es not_active Expired
- 1981-05-01 DK DK194181A patent/DK160910C/da not_active IP Right Cessation
-
1983
- 1983-03-11 US US06/474,309 patent/US4528185A/en not_active Expired - Fee Related
-
1984
- 1984-07-26 KE KE3432A patent/KE3432A/xx unknown
-
1986
- 1986-12-30 MY MY469/86A patent/MY8600469A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KE3432A (en) | 1984-08-17 |
| US4528185A (en) | 1985-07-09 |
| AU7001581A (en) | 1981-12-03 |
| MA19132A1 (fr) | 1981-12-31 |
| MY8600469A (en) | 1986-12-31 |
| PT72950A (en) | 1981-05-01 |
| BR8102689A (pt) | 1982-01-26 |
| US4409358A (en) | 1983-10-11 |
| ES501820A0 (es) | 1982-10-01 |
| DE3161008D1 (en) | 1983-11-03 |
| EP0039788A3 (en) | 1981-11-25 |
| GR75196B (en, 2012) | 1984-07-13 |
| EP0039788B1 (de) | 1983-09-28 |
| DK194181A (da) | 1981-11-04 |
| DK160910C (da) | 1991-10-21 |
| ES8300003A1 (es) | 1982-10-01 |
| PT72950B (en) | 1982-03-26 |
| IL62645A (en) | 1984-04-30 |
| DK160910B (da) | 1991-05-06 |
| AU538632B2 (en) | 1984-08-23 |
| GB2077740A (en) | 1981-12-23 |
| IL62645A0 (en) | 1981-06-29 |
| EP0039788A2 (de) | 1981-11-18 |
| GB2077740B (en) | 1984-04-11 |
| IE51149B1 (en) | 1986-10-15 |
| IE810950L (en) | 1981-11-13 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |