EP0195054A1 - Pesticides a base de n-oxydes d'etain tricycloalkyl-(2-pyridylthio) - Google Patents
Pesticides a base de n-oxydes d'etain tricycloalkyl-(2-pyridylthio)Info
- Publication number
- EP0195054A1 EP0195054A1 EP85904775A EP85904775A EP0195054A1 EP 0195054 A1 EP0195054 A1 EP 0195054A1 EP 85904775 A EP85904775 A EP 85904775A EP 85904775 A EP85904775 A EP 85904775A EP 0195054 A1 EP0195054 A1 EP 0195054A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- effective amount
- plants
- compounds
- inert carrier
- 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- Withdrawn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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title description 3
- 230000000361 pesticidal effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 42
- 230000000855 fungicidal effect Effects 0.000 claims description 25
- 230000000749 insecticidal effect Effects 0.000 claims description 16
- 241000233866 Fungi Species 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 abstract description 16
- 239000000417 fungicide Substances 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 7
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 6
- 239000000642 acaricide Substances 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- 238000012360 testing method Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 231100000167 toxic agent Toxicity 0.000 description 19
- 239000003440 toxic substance Substances 0.000 description 19
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- 239000002270 dispersing agent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 240000003768 Solanum lycopersicum Species 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 8
- 239000012875 nonionic emulsifier Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- 240000007087 Apium graveolens Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 241000255993 Trichoplusia ni Species 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 230000007613 environmental effect Effects 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 6
- -1 i.e. Chemical group 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241001600408 Aphis gossypii Species 0.000 description 5
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 5
- 235000010591 Appio Nutrition 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001508566 Hypera postica Species 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241000238675 Periplaneta americana Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000238421 Arthropoda Species 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000045232 Canavalia ensiformis Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 241001597359 Septoria apiicola Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 241000221566 Ustilago Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 235000011160 magnesium carbonates Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000001965 potato dextrose agar Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 235000001508 sulfur Nutrition 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- XDFUNRTWHPWCKO-UHFFFAOYSA-N 4,5,9,10-tetrahydropyrene Chemical compound C1CC2=CC=CC3=C2C2=C1C=CC=C2CC3 XDFUNRTWHPWCKO-UHFFFAOYSA-N 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- YKFRAOGHWKADFJ-UHFFFAOYSA-N Aramite Chemical compound ClCCOS(=O)OC(C)COC1=CC=C(C(C)(C)C)C=C1 YKFRAOGHWKADFJ-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241001508570 Hypera brunneipennis Species 0.000 description 1
- 241000500891 Insecta Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241000918584 Pythium ultimum Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BIWJNBZANLAXMG-UHFFFAOYSA-N chlordane Chemical compound ClC1=C(Cl)C2(Cl)C3CC(Cl)C(Cl)C3C1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000877 morphologic effect Effects 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
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 102220047090 rs6152 Human genes 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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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
- 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
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
- A01N55/04—Tin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
Definitions
- the present invention relates to novel tricycloalkyl tin derivatives of 2-pyridyl N-oxide.
- R, R' , and R" are independently selected alkyl and preferably lower alkyl, i.e., alkyl having 1-4 carbon atoms; and aryl having 6-10 carbon atoms, preferably phenyl; n and m independently are 0-1 and r is 1-2, with the proviso that n plus m plus r is three, which are useful as heat stabilizers for vinyl chloride resins.
- R is cycloalkyl of 3 to 8 carbon atoms and show surprisingly good activity as miticides and insecticides, especially against lepidoptera. These compounds also exhibit good activity as a fungicide against a variety of fungi, particularly fungi which cause plant fungal diseases as well as an acaricide and insecticide.
- the present invention is based on my finding that the present compounds exhibit surprisingly good activity against mites and lepidoptera, and against certain plant fungicidal diseases. Moreover, it is believed these compounds do not exhibit phyto- toxicity, unlike other trialkyl and triaryl tin deriva ⁇ tives of 2-pyridyl N-oxides. Thus, lack of phytotoxicity is a distinct advantage in agricultural applications, since the compound may be used to protect plant crops from insect, acarine, and various plant fungal bests without herbicidal effects or damage to the plant itself.
- the present invention is also directed to fungicidal, insecticidal and acaricidal compositions containing and methods of using the compounds of the present invention. In addition, the present invention is directed to non- phytotoxic fungicidal, insecticidal and acaricidal compositions comprising these compounds which are not appreciably phytotoxic.
- cycloalkyl refers to cyclic alkyl groups and includes, for example, cyclopropyl, cyclopentyl, cyclohexyl , cycloheptyl , and the like.
- Preferred R groups include cyclopentyl, cyclohexyl, cycloheptyl, and the like.
- Especially preferred R groups include cyclohexyl.
- the compound of the present invention may be conveniently prepared according to the following reaction scheme:
- Reaction (1) is a conventional preparation of the mercaptide salt of a mercaptan. Reaction (1) is conducted by combining II and III in solvent. It is preferred to use a slight excess of III relative to II, on the order of up to about 1.1 equivalents III per equivalent II. Suitable solvents include low molecular weight alcohols. Especially preferred are such alcohols having 1 to 4 carbon atoms, such as methanol, ethanol, n-propanol, and the like. The reaction is conducted at a temperature of about 0°C to about 20°C preferably about 20°C, or, for convenience at ambient temperature. The reaction is generally complete within about 0.5 to about 1 hour.
- the product mercaptide salt is isolated by conventional procedures, such as stripping, and the like, or, after removal of the solvent may be used in reaction (2) without further isolation.
- Reaction (2) is conducted by combining approximately equimolar amounts of IV and V in solvent. Although the reactants may be combined in any order, it is preferred to add V to a stirred mixture of IV in solvent. Suitable solvents include inert organic solvents such as dimethoxyethane, and the like. The reaction is conducted at a temperature of about 0°C to about 80°C, preferably from about 20°C to about 80°C, or at reflux, and is generally complete within about 4 to about 8 hours.
- the product, I is isolated by conventional procedures such as stripping, extraction, filtration, and the like. Utility
- the compounds of the present invention are useful in controlling a wide variety of pests.
- These compounds are active as a fungicide and are particularly effective in controlling a variety fungi which are deleterious to plants, including plant fungal infections. These compounds are particularly effective in controlling leaf blights caused by organisms such as Phytophthora infestans and Septoria apii. In addition, they are useful in controlling downy mildews caused by organisms such as Plasmopara viticola, early blights caused by organisms such as Alternaria solani, and powdery mildews such as that caused by Erisiphe polygoni .
- These compounds are also effective as an insecticide and acaracide and may be used in controlling a variety of insect and arthropod pests. In particular, they are especially effective in controlling arachnids of the order Acarina such as mites, and in controlling
- the compounds are not usually applied " full strength, but are generally incorporated with conventional biologically inert extenders or carriers normally employed for
- the toxicants of this invention may be applied as sprays, dusts, or
- ⁇ ⁇ granules to the insects, their environment or hostages susceptible to insect attack. It may be formulated as granules of large particle size, powdery dusts, wettable powders, emulsifiable concentrates, solutions, or as any of several other known types of formulations, depending on the desired mode of application.
- Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersants. These compositions normally contain from about 5% to 80% insecticide, and the rest inert material, 0 which includes dispersing agents, emulsifying agents and wetting agents.
- the powder may be applied to the soil as a dry dust, or preferably as a suspension in water.
- Typical carriers include fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wettable, 5 inorganic diluents.
- Typical wetting, dispersing or emulsifying agents include, for example: the aryl and alkylaryl sulfonates and their sodium salts; alkylamide sulfonates, including fatty methyl taurides; alkylaryl polyether alcohols, sulfated higher alcohols and polyvinyl 0 alcohols; polyethylene oxides; sulfonated animal and vege ⁇ table oils; sulfonated petroleum oils; fatty acid esters
- the surface-active agent when used, normally 1 Q comprises from 1% to 15% by weight of the insecticidal composition.
- Dusts are freely flowing admixtures of the active insecticide with finely divided solids such as talc, natural clays, kieselguhr, pyrophyllite, chalk,
- diatomaceous earths 15 diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant.
- These finely divided solids have an average particle size of less than about
- a typical dust formulation useful herein contains 75% silica and 25% of toxicant.
- Useful liquid concentrates include the emulsifiable concentrates, which are homogeneous liquid or paste compositions which are readily dispersed in water or 5 other dispersant, and may consist entirely of the insecti ⁇ cide with a liquid or solid emulsifying agent, or may also contain a liquid carrier such as xylene, heavy aromatic naphthas, isophorone, and other nonvolatile organic solvents.
- these concentrates are 0 dispersed in water or other liquid carrier, and are normally applied as a spray to the area to be treated.
- compositions for insecticidal applications include simple solutions of the active insecticide in a dispersant in which it is completely 5 soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
- Granular formulations, wherein the insecticide is carried on relatively coarse particles, are of particular utility for aerial distribution or for penetration of cover-crop 0 canopy.
- Pressurized sprays typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low-boiling dispersant solvent carrier, such as the Freons, may also be used. All of those techniques for formulating and applying insecticides are well known in the art.
- the percentages by weight of the insecticide may vary according to the manner in which the composition is to be applied and the particular type of formulation, but in general comprise 0.5% to 95% of the toxicant by weight of the insecticidal composition.
- insecticidal compositions may be formulated and applied with other active ingredients, including nema- tocides, insecticides, fungicides, bactericides, plant- growth regulators, fertilizers, etc.
- active ingredients including nema- tocides, insecticides, fungicides, bactericides, plant- growth regulators, fertilizers, etc.
- an effective amount and concentration of the toxicant of this invention is, of course, employed.
- insects refer to their broad and commonly understood usage rather than to those creatures which, in the strict bio ⁇ logical sense, are classified as insects.
- insect is used not only to include small invertebrate animals belonging to the class "Insecta”, but also to other related classes of arthropods, whose members are segmented invertebrates having more or fewer than six legs, such as spiders, mites, ticks, centipedes, worms, and the like.
- the compounds of the invention When used as a fungicide, the compounds of the invention are applied in fungicidally effective amounts to fungi and/or their habitats, such as vegetative hosts and non-vegetative hosts, e.g., animal products.
- the amount used will, of course, depend on several factors such as the host, the type of fungus, and the particular compound of the invention.
- the fungicides of the invention are not usually applied full strength, but are generally incorporated with conven ⁇ tional, biologically inert extenders or carriers normally employed for facilitating dispersion of active fungicidal compounds, recognizing that the formulation and mode of application may affect the activity of the fungicide.
- the fungicide of this invention may be formulated and applied as granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions, or as any of several other known types of formulations, depending on the desired mode of application.
- Wettable powders are in the form of finely divided particles which disperse readily in water or other dispersants. These compositions normally contain from about 5% to 80% fungicide, and the rest inert material, which includes dispersing agents, emulsifying agents and wetting agents.
- the powder may be applied to the soil as a dry dust, or preferably as a suspension in water.
- Typical carriers include fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wettable, inorganic diluents.
- Typical wetting, dispersing or emul ⁇ sifying agents include, for example: the aryl and alkyl- aryl sulfonates and their sodium salts; alkylamide sulfonates, including fatty methyl taurides; alkylaryl polyether alcohols, sulfated higher alcohols and polyvinyl alcohols; polyethylene oxides; sulfonated animal and vege ⁇ table oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition products of long-chain mercaptans and ethylene oxide.
- Many other types of useful surface-active agents are available in commerce.
- the surface-active agent when used, normally comprises from 1% to 15% by weight of the fungicidal composition.
- Dusts are freely flowing admixtures of the active fungicide with finely divided solids such as talc, natural clays, kieselguhr, pyrophyllite, chalk, diatoma- ceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant.
- finely divided solids have an average particle size of less than about 50 microns.
- a typical dust formulation useful herein contains 75% silica and 25% of toxicant.
- Useful liquid concentrates include the emulsifiable concentrates, which are homogeneous liquid or paste compositions which are readily dispersed in water or other dispersant, and may consist entirely of the fungi ⁇ cide with a liquid or solid emulsifying agent, or may also contain a liquid carrier such as xylene, heavy aromatic naphthas, isophorone, and other nonvolatile organic sol ⁇ vents.
- these concentrates are dispersed in water or other liquid carrier, and are normally applied as a spray to the area to be treated.
- fungicidal applications include simple solutions of the active fungi ⁇ cide in a dispersant in which it is completely soluble at the desired concentration, such as acetone, alkylatsd naphthalenes, xylene, or other organic solvents.
- Granular formulations wherein the fungicide is carried on rela ⁇ tively coarse particles, are of particular utility for aerial distribution or for penetration of cover-crop canopy.
- Pressurized sprays typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low-boiling dispersant solvent carrier, such as the Freons, may also be used. All of those techniques for formulating and applying fungicides are well known in the art.
- the percentages by weight of the fungicide may vary according to the manner in which the composition is to be applied and the particular type of formulation, but in general comprise 0.5% to 95% of the toxicant by weight of the fungicidal composition.
- the fungicidal compositions may be formulated and applied with other active ingredients, including other fungicides, insecticides, nematocides, bactericides, plant-growth regulators, fertilizers, etc.
- ambient or “room temperature” refers to about 20°C to about 25°C.
- percent refers to gram moles.
- equivalent refers to a quantity of reagent equal in moles, to the moles of the preceding or succeeding reagent recited in that example in terms of finite moles or finite weight or volume. Also, unless expressly stated to the contrary, geometric isomer and racemic mixtures are used as starting materials and correspondingly, isomer mixtures are obtained as products.
- step (a) To a stirred mixture of 2.5 g (0.01966 mole) 2-mercaptopyridine-N-oxide in methanol which had been stirred for a few minutes at room temperature, 0.5 g- (0.022 mole) sodium metal was added slowly and stirred until all dissolved. The methanol was removed with reduced pressure and heat, using toluene to chase the methanol, yielding the sodium salt which was used in step (b) without further isolation.
- step (b) Dimethoxyethane (about 100 ml) was added to the sodium salt from step (a). To that stirred mixture, 6 g (0.01339 mole) tricyclohexyl tin bromide was added in one portion with stirring. The reaction mixture was refluxed for 8 hours.
- the dimethoxyethane was removed under reduced pressure and heat. Water (about 75 ml) and methylene chloride (about 125 ml) were added to the residue; the resulting mixture was stirred. The layers were phase separated. The methylene chloride layer was washed with water 2 times, dried with magnesium sulfate, filtered and stripped to give the crude product. The crude product was washed with hexane and ethyl ether, filtered and stripped to give about 4.8 g of the above- identified product as a liquid which upon standing gave an opaque solid.
- Mycelial Inhibition Compounds were evaluated for in vitro fungicidal effectiveness by means of a mycelial inhibition test. This test is designed to measure the fungitoxic activity of fungicidal chemicals in terms of their degree of inhi ⁇ bition of mycelium growth. Fungi used were Pythium ultimum, Rhizoctonia solani, Fusarium moniloforme, Botrytis cinerea, Aspergillus niger and Ustilago hordeii. Each compound to be tested was dissolved in acetone to 500 ppm concentration. Paper strips were infused with the particular mycelium growth by covering the paper with a potato dextrose broth culture of mycelial suspension.
- Example B Tomato Late Blight Compounds were tested for the preventative control of the Tomato Late Blight organism Phytophthora infestans. Five- to six-week-old tomato (cultivar Bonny Best) seedlings were used. The tomato plants were sprayed with a 200-ppm suspension of the test compound in acetone, water and a nonionic emulsifier. The sprayed plants were then inoculated 1 day later with the organism, placed in an environmental chamber and incubated at 66°F to 68°F and 100% relative humidity for at least 16 hours. Following the incubation, the plants were maintained in a greenhouse for approximately 7 days. The percent disease control provided by a given test compound was based on the percent disease reduction relative to untreated check plants. The results are tabulated in Table I.
- Example C Rice Blast Compounds of this invention were tested for control of the Rice Blast organism Piricularia oryzae, using 10- to 14-day-old rice plant seedlings (Calrose M-9 variety). Seedling plants were sprayed with a 625-ppm solution of the test compound in acetone, water and a non- ionic emulsifier (ORTHO X-77 spreader). The sprayed plants were inoculated 1 day later with the organism in an environmental chamber. After inoculation, the plants were kept in an environmental chamber for about 48 hours under conditions of about 72°F to 75°F and about 100% relative humidity. Following the incubation period, the plants were placed in a greenhouse with a temperature of about 72°F and maintained with bottom watering for about 12 to
- the percent disease control provided by a given test compound is based on a comparison of the percentage disease relative to the percent disease development on the untreated check plants: (% disease in treated plants)
- Example D Tomato Early Blight Compounds were tested for the control of the Tomato Early Blight organism Alternaria solani.
- Tomato (variety Bonny Best) seedlings of 6- to 7-weeks old were used.
- the tomato plants were sprayed with a 200-ppm solution of the test compound in an acetone-and-water solution containing a small amount of a nonionic emulsi ⁇ fier.
- the sprayed plants were inoculated 1 day later with the organism, placed in the environmental chamber and incubated at 66°F to 68°F and 100% relative humidity for 24 hours. Following the incubation, the plants were main ⁇ tained in a greenhouse for about 12 days. Percent disease control was based on the percent disease development on untreated check plants. The results are tabulated in Table I.
- Example E Celery Late Blight
- the Celery Late Blight tests were conducted using celery (Utah) plants 11 weeks old.
- the Celery Late Blight organism was Septoria apii.
- the celery plants were sprayed with 200-ppm solutions of the candidate toxicant mixed with acetone, water and a nonionic emulsifier.
- the plants were then inoculated with the organism and placed in an environmental chamber and incubated at 66°F to 68°F in 100% relative humidity for an extended period of time (approximately 48 hours). Following the incubation, the plants were allowed to dry and then were maintained in a greenhouse for approximately 14 days.
- the percent disease control provided by a given test compound is based on the percent disease reduction relative to untreated check plants. The results are reported in Table I.
- Bean Powdery Mildew organism Erysiphe polygoni Seedling bean plants were sprayed with a 250-ppm solution of the test compound in acetone, water and a nonionic emulsifier. The sprayed plants were then inoculated 1 day later with the organism. The plants were maintained for 10 days at temperatures of 68°F at night with daytime temperatures of 72°F to 80°F; relative humidity was maintained at 40% to 60%. The percent disease control provided by a given test compound was based on the percent disease reduction rela ⁇ tive to the untreated check plants. The results as percent control are tabulated in Table I.
- Example G Bean Rust Compounds were evaluated for their ability to eradicate Bean Rust caused by Uromyces phaseoli typica on pinto beans.
- Pinto bean plants, variety Idaho 1-11, 16 (summer) or 19 (winter) days old were inoculated with a 50-ppm suspension of uredospores in water containing a small amount of nonionic surfactant.
- the inoculated plants were placed in an environmental chamber immediately after inoculation and incubated 20 hours. Following the incubation period, the plants were removed from the cham ⁇ ber and placed in a greenhouse maintained at 66-68°F and 60-80% relative humidity. Two days after inoculation, the plants were treated by spraying with a 200-ppm solution of test compound in an acetone and water carrier formulation containing a small amount of nonionic surfactant.
- One or two replicate pots (each containing two plants) were used for each compound.
- one or two replicate pots were sprayed with the same carrier formulation (without a test compound) as a control (hereinafter "untreated Checks").
- the plants were kept in the greenhouse until evaluated.
- the plants were evaluated for disease control when disease symptoms were well developed on the untreated Checks, normally about 14 days after treatment.
- the per ⁇ centage disease control (or eradication) provided by a test compound was based on the percent disease reduction relative to the untreated Checks. The results are reported in Table I.
- Example H Example H
- the compounds of this invention were tested for their insecticidal activity against cotton aphids (Aphis gossypii Glover) .
- An acetone solution of the test com- pound containing a small amount of nonionic emulsifier was diluted with water to give a concentration of 40 ppm.
- Example I Aphid Systemic Evaluation This procedure is used to assess the ability of a candidate insecticide to be absorbed through the plant root system and translocate to the foliage and thus to show insecticidal activity against the cotton aphid (Aphis gossypii Glover) .
- Two cucumber plants planted in a 4-inch fiber r pot with a soil surface area of 80 cm'' are used. Forty ml of an 80-ppm solution of the candidate insecticide is poured around the plants in each pot. (This corresponds to 40 of actual toxicant.) The plants are maintained throughout in a greenhouse at 75-85°F.
- the treated plants are infested with aphids by placing well-colonized leaves over the treated leaves so as to allow the aphids to migrate easily from the inoculated leaf to the treated leaf. Three days after infestation, mortality readings were taken. The results are tabulated in Table II in terms of percent control.
- Example J Mite Adult Compounds of this invention were tested for their insecticidal activity against parathion-resistant Two-spotted Spider Mite [Tetranychus urticae Koch] .
- An acetone solution of the candidate toxicant containing a small amount of nonionic emulsifier was diluted with water to 40 ppm.
- Lima bean leaves which were infested with mites were dipped in the toxicant solution.
- the results are tabulated in Table II in terms of percent control.
- Example K Mite Egg Control Compounds of this invention were tested for their ovicidal activity against eggs of the two-spotted spider mite [Tetranychus urticae Koch] .
- Housefly Compounds of this invention were tested for their insecticidal activity against the Housefly (Musca domestica Linnaeus) .
- a 500-ppm acetone solution of the candidate toxicant was placed in a micro sprayer
- Example M American Cockroach Compounds of this invention were tested for their insecticidal activity against Chlorodane-resistant American Cockroaches (Periplaneta americana Linnaeus).
- a 500-ppm acetone solution of the candidate toxicant was placed in a micro sprayer (atomizer) .
- a random mixture of anesthetized male and female roaches was placed in a con- tainer and 55 mg of the above-described solution was sprayed on them.
- a lid was placed on the container.
- a mortality reading was made after 24 hours. The results are tabulated in Table II in terms of percent control.
- Example N Alfalfa Weevil The compounds of this invention were tested for their insecticidal activity against Alfalfa Weevil [Hypera brunneipennis (Boheman)].
- a 500-ppm acetone solution of the candidate toxicant was placed in a micro sprayer (atomizer).
- a random mixture of male and female weevils was placed in a container and 55 mg of the above-described acetone solution was sprayed on them.
- a lid was placed on the container.
- a mortality reading was made after
- Example O Cabbage Looper Control The compounds of this invention were tested for their insecticidal activity against Cabbage Looper [Trichoplusia ni (Hubner)]. An acetone solution of the - candidate toxicant containing a small amount of nonionic emulsifier was diluted with water to give a concentration of 500 ppm. Excised cucumber leaves were dipped in the toxicant solution and allowed to dry. The leaves were then infested with Cabbage Looper larvae. Mortality readings were taken after 24 hours. The results are tabulated in Table II in terms of percent control. Examples P and O
- Example P The compound was respectively tested for pre-emergent and post-emergent activity against a variety of grasses and broad-leaf plants including one grain crop and one broad-leaf crop.
- Example P The compound was respectively tested for pre-emergent and post-emergent activity against a variety of grasses and broad-leaf plants including one grain crop and one broad-leaf crop.
- An acetone solution of the test compound was prepared by mixing 750 mg of the test compound, 220 mg of a nonionic surfactant and 25 ml of acetone. This solution was added to approximately 125 ml of water containing 156 mg of surfactant.
- Seeds of the test vegetation were planted in a pot of soil and the test compound solution was sprayed uniformly onto the soil surface at a dose of 27.5 micro- grams/cm .
- the pot was watered and placed in a green- house.
- the pot was watered intermittently and was observed for seedling emergence, health of the emerging seedlings, etc., for a 3-week period.
- the herbicidal effectiveness of the test compound was rated based on the physiological observations.
- a O-to-100-scale was used, 0 representing no phytotoxicity and 100 representing complete kill. The results of these tests are summarized in Table III, hereinbelow.
- Example 0 Post-Emergent Test The test compound was formulated in the same manner as described above for the pre-emergent test. The concentration of the test compound in this formulation was 5000 ppm. This formulation was uniformly sprayed on 2 similar pots of 24-day-old plants (approximately 15 to 25 plants per pot) at a dose of 27.5 micrograms/cm 2 .
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Abstract
Composés de formule (I), où R est un cycloalkyle comportant de 3 à 8 atomes de carbone, présentant une bonne activité en tant que fongicides, acaricides et insecticides, sans phytotoxicité appréciable.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US65548584A | 1984-09-27 | 1984-09-27 | |
US655485 | 1991-02-14 |
Publications (1)
Publication Number | Publication Date |
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EP0195054A1 true EP0195054A1 (fr) | 1986-09-24 |
Family
ID=24629078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85904775A Withdrawn EP0195054A1 (fr) | 1984-09-27 | 1985-09-26 | Pesticides a base de n-oxydes d'etain tricycloalkyl-(2-pyridylthio) |
Country Status (2)
Country | Link |
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EP (1) | EP0195054A1 (fr) |
WO (1) | WO1986002075A1 (fr) |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CA501851A (fr) * | 1954-04-27 | C. Ladd Elbert | Fungicide contenant des pyridine-2-thiols ou leurs derives | |
US2809971A (en) * | 1955-11-22 | 1957-10-15 | Olin Mathieson | Heavy-metal derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same |
NL251247A (fr) * | 1959-05-04 | |||
DE1492287A1 (fr) * | 1963-02-21 | 1970-01-29 | ||
US3787417A (en) * | 1969-07-18 | 1974-01-22 | Olin Corp | Dialkyltin salts of substituted pyridine-1-oxides |
US3753990A (en) * | 1972-01-17 | 1973-08-21 | Procter & Gamble | Phenylbismuth bis(2-pyridinethiol 1-oxide) |
US3833565A (en) * | 1972-09-29 | 1974-09-03 | Procter & Gamble | Phenylantimony bis(2-pyridinethiol 1-oxide) |
US3832370A (en) * | 1972-10-19 | 1974-08-27 | Stauffer Chemical Co | Organotin miticidal and insecticidal compounds |
JPS5544744B2 (fr) * | 1973-08-24 | 1980-11-13 | ||
FR2398061A1 (fr) * | 1977-07-21 | 1979-02-16 | Oreal | Nouveau procede de preparation de sels organiques mixtes de l'aluminium |
-
1985
- 1985-09-26 EP EP85904775A patent/EP0195054A1/fr not_active Withdrawn
- 1985-09-26 WO PCT/US1985/001870 patent/WO1986002075A1/fr unknown
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Title |
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See references of WO8602075A1 * |
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