DE3445853A1 - Selective fungicides - Google Patents
Selective fungicidesInfo
- Publication number
- DE3445853A1 DE3445853A1 DE19843445853 DE3445853A DE3445853A1 DE 3445853 A1 DE3445853 A1 DE 3445853A1 DE 19843445853 DE19843445853 DE 19843445853 DE 3445853 A DE3445853 A DE 3445853A DE 3445853 A1 DE3445853 A1 DE 3445853A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- chain
- stands
- straight
- fungicidal agents
- 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- Withdrawn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
- 239000000417 fungicide Substances 0.000 title claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims abstract description 14
- 241000233654 Oomycetes Species 0.000 claims abstract description 12
- 150000002170 ethers Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229920000151 polyglycol Polymers 0.000 claims abstract description 10
- 239000010695 polyglycol Substances 0.000 claims abstract description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- -1 that is Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 125000004804 1-methylmethylene group Chemical group [H]C([H])([H])C([H])([*:2])[*:1] 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
BAYER AKTIENGESELLSCHAFT 5090 Leverkusen, BayerwerkBAYER AKTIENGESELLSCHAFT 5090 Leverkusen, Bayerwerk
Konzernverwaltung RP 1 / ΠΓ7Group administration RP 1 / ΠΓ7
Patentabteilung Bas/Kü-c * ^· ULL" Patent department Bas / Kü-c * ^ · ULL "
II bII b
Selektiv-fungizide MittelSelective fungicidal agents
Die vorliegende Erfindung betrifft die Verwendung von bekannten Salzen von Benzolsulfonsäuren als selektivfungizide Mittel.The present invention relates to the use of known salts of benzenesulfonic acids as selective fungicides Middle.
Salze von Benzolsulfonsäuren sind als Emulgatoren bekannt, ihre Verwendung in Formulierungen im Pflanzenschutz
ist gängig. Außerdem ist bekannt, daß sie
bakterizide und fungizide Eigenschaften haben. So
zeigen sie eine Wirkung z.B. gegen den Erreger der
Blattfleckenkrankheit am Reis (vgl. z.B. Jap. Patent Publikation 55-111-403) oder gegen den Mosaikvirus an
Gurken (vgl. z.B. Jap. Patent Publikation 54-117-025).Salts of benzenesulfonic acids are known as emulsifiers; their use in formulations in crop protection is common. It is also known that
have bactericidal and fungicidal properties. So
do they show an effect e.g. against the causative agent of the
Leaf spot disease on rice (see, for example, Japanese patent publication 55-111-403) or against the mosaic virus on cucumbers (see, for example, Japanese patent publication 54-117-025).
Weiterhin ist bekannt, daß bestimmte Dithicarbamate,
besonders das Zink-(NrN' -propylen-1,2-bis-dithiocarbamat)
fungizide Wirkung aufweisen, sie werden besonders zur Bekämpfung von Oomyceten eingesetzt (vgl.It is also known that certain dithicarbamates,
in particular the zinc (N r N'-propylene-1,2-bis-dithiocarbamate) have fungicidal effects; they are used in particular to combat oomycetes (cf.
R. Wegler, "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel"
Bd. 6, Seiten 395-396 (1981),
Springer-Verlag, Berlin, Heidelberg, New York).R. Wegler, "Chemistry of Plant Protection and Pest Control Agents" Vol. 6, pages 395-396 (1981),
Springer-Verlag, Berlin, Heidelberg, New York).
Le A 23 287Le A 23 287
Gegenüber diesen Verbindungen zeigen die erfindungsgemäß angewendeten Stoffe den Vorteil, daß sie selektiv gegen Oomyceten wirken und nur ein Drittel der Aufwandmenge an Salzen von Benzolsulfonsäuren aufgewendet werden muß, um die Wirkungsgröße von den bekannten Carbamaten zu erreichen.Compared to these compounds, show those according to the invention applied substances have the advantage that they act selectively against Oomycetes and only a third of the application rate on salts of benzenesulfonic acids must be used in order to increase the effectiveness of the known carbamates to reach.
Es wurde gefunden, daß die bekannten Salze von Benzolsulfonsäuren der Formel (I)It has been found that the known salts of benzenesulfonic acids of the formula (I)
(I)(I)
in welcherin which
M für ein Alkali-, Erdalkali- oder gegebenenfalls substituiertes Ammoniumäquivalent stehtM represents an alkali, alkaline earth or optionally substituted ammonium equivalent
undand
für geradkettiges oder verzweigtes Alkyl steht, gegebenenfalls in Gegenwart von Alkylarylpolyglycolethern starke selektiv-fungizide Eigenschaften aufweisen.represents straight-chain or branched alkyl, optionally in the presence of alkylaryl polyglycol ethers have strong selective fungicidal properties.
Die Alkylarylpolyglykolether der Formel (II)The alkylaryl polyglycol ethers of the formula (II)
alkyleralkylers
(II)(II)
Le A 23 287Le A 23 287
mm Jf mmmm Jf mm
in welcherin which
R für geradkettiges oder verzweigtes Niederalkyl steht,R represents straight-chain or branched lower alkyl,
alkylen für geradkettiges oder verzweigtes Niederalkylen steht,alkylene stands for straight-chain or branched lower alkylene,
m für eine Zahl von 2 bis 7 und η für eine Zahl bis 30 stehen, kommen dafür infrage.m for a number from 2 to 7 and η for a number up to 30, come into question.
überraschenderweise zeigen die Salze von Benzölsulfonsäuren gegebenenfalls in Gegenwart von Alkylarylpolyglykolethern eine erheblich höhere selektiv-fungizide Wirkung bei der Bekämpfung von Oomyceten als aus dem Stand der Technik bekannte Oomyceten-Mittel das Zink-(N,N'-propylen-1,2-bis-dithiocarbamat). Surprisingly, show the salts of benzölsulfonic acids optionally in the presence of alkylaryl polyglycol ethers a significantly higher selective fungicidal Zinc (N, N'-propylene-1,2-bis-dithiocarbamate) has an effect in combating oomycetes as an oomycete agent known from the prior art.
Die erfindungsgemäß zu verwendenden Salze von Benzolsulfonsäuren und gegebenenfalls die Alkylarylpolyglykolether sind durch die Formel (I) bzw. (II) genau definiert und sind bereits bekannt (vgl. Jap. Patent Publikation 55-111-403). Die Verbindungen sind käuflieh auch im technischen Maßstab zu erwerben. Die Salze der Benzolsulfonsäuren können in einfacher Weise nach gängigen Methoden aus den Benzolsulfonsäuren durch Umsetzung mit entsprechenden Salzen gewonnen werden.The salts of benzenesulfonic acids to be used according to the invention and optionally the alkylaryl polyglycol ethers are specified by formula (I) and (II), respectively defined and are already known (see. Japanese Patent Publication 55-111-403). The connections are for sale also available on a technical scale. The salts of benzenesulfonic acids can easily be used common methods can be obtained from the benzenesulfonic acids by reaction with appropriate salts.
Le A 23 287Le A 23 287
-J·-J
Die Benzolsulfonsäuren können z.B. aus den entsprechenden Alkylbenzol mit Chlorsulfonsäure gewonnen werden (vgl. Jap. Patent Publikation 55-111-403).The benzenesulfonic acids can e.g. be obtained from the corresponding alkylbenzene with chlorosulfonic acid (see Japanese Patent Publication 55-111-403).
In der Formel (I) steht M vorzugsweise für ein Natrium-, Kalium-, Magnesium- oder Calciumäquivalent oder für ein substituiertes Ammoniumäquivalent, wie 2-Hydroxyethylammonium, und R steht für geradkettiges oder verzweigtes Alkyl mit 4 bis 14 Kohlenstoffatomen, insbesondere Decyl, Undecyl und Dodecyl.In the formula (I), M preferably stands for a sodium, potassium, magnesium or calcium equivalent or for substituted ammonium equivalent, such as 2-hydroxyethylammonium, and R is straight-chain or branched Alkyl with 4 to 14 carbon atoms, especially decyl, undecyl and dodecyl.
In der Formel (II) steht R vorzugsweise für geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen, insbesondere Methyl,In the formula (II), R preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, especially methyl,
alkylen für geradkettiges oder verzweigtes Alkylen mit 1 bis 4 Kohlenstoffatomen, insbesondere Methylen und 1-Methylmethylen,alkylene for straight-chain or branched alkylene with 1 to 4 carbon atoms, in particular methylene and 1-methylmethylene,
m für eine Zahl von 2,0 bis 5,0 undm for a number from 2.0 to 5.0 and
η für eine ganze Zahl von 15 bis 30, insbesondere 17 und 27.η for an integer from 15 to 30, especially 17 and 27.
Als Beispiele für erfindungsgemäß zu verwendende Wirkstoffe seien genannt:As examples of active ingredients to be used according to the invention are mentioned:
Le A 23 287Le A 23 287
1. Monoethanolaminsalz der p-Dodecylbenzolsulfon säure der Formel1. Monoethanolamine salt of p-dodecylbenzenesulfone acid of the formula
n~C12H25 \ /- n ~ C 12 H 25 \ / -
und
2. ßin Gemisch bestehend ausand
2. ßin mixture consisting of
1) 32 % des Calciumsalzes der p-Dodecylbenzol sulfonsäure der Formel1) 32% of the calcium salt of p-dodecylbenzene sulfonic acid of the formula
2) 16 % n-Butanol, 10 3) 4 % Xylol und2) 16% n-butanol, 10 3) 4% xylene and
4) 48 % Alkylary!polyglykolether der Formel4) 48% alkylaryl polyglycol ethers of the formula
CH3 CH 3
(H3C-/ ^-CH)2-η ^Λ-Ο- (C2H4O)-^ H.(H 3 C- / ^ -CH) 2 - η ^ Λ-Ο- (C 2 H 4 O) - ^ H.
Die erfindungsgemäß verwendbaren Wirkstoffe weisen starke, selektiv-fungizide Wirkungen zur Bekämpfung von Oomyceten auf. Sie können deshalb für den Gebrauch als Selektiv-Fungizide verwendet werden.The active ingredients which can be used according to the invention have strong, selective fungicidal effects for combating of Oomycetes on. They can therefore be used as selective fungicides for use.
Le A 23 287Le A 23 287
Beispielhaft aber.nicht begrenzend seien einige Erreger von pilzlichen Erkrankungen, die unter die Klasse der Oomyceten fallen, genannt:Some pathogens are exemplary but not limiting of fungal diseases that fall under the class of the Oomycetes called:
Pseudoperonospora cubensis und Phytophthora infestans.Pseudoperonospora cubensis and Phytophthora infestans.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen und von Pflanzgut.The fact that the active compounds are well tolerated by plants in those necessary for combating plant diseases Concentrations allow a treatment of above-ground parts of plants and of seedlings.
Die Wirkstoffe werden im allgemeinen in wäßriger Verdünnung ausgebracht. Sie können jedoch auch in die üblichen Formulierungen übergeführt werden, wie Lösungen, Pulver und Pasten, sowie ULV-Formulierungen.The active ingredients are generally applied in an aqueous dilution. However, you can also use the Conventional formulations are transferred, such as solutions, powders and pastes, as well as ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von weiteren oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugende Mitteln.These formulations are produced in a known manner, e.g. by mixing the active ingredients with extenders, that is, liquid solvents and / or solid carriers, optionally using further surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents Means.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aro-In the case of using water as an extender For example, organic solvents can also be used as auxiliary solvents be used. The main liquid solvents that can be used are: aromatics, such as Xylene, toluene or alkylnaphthalenes, chlorinated aromas
Le A 23 287Le A 23 287
- r- - r-
maten oder chlorierte aliphatisch^ Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid.mates or chlorinated aliphatic ^ hydrocarbons, such as chlorobenzenes, chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or Paraffins, e.g. petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or Cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide.
Als feste Trägerstoffe kommen in Frage: z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate.The following can be used as solid carriers: e.g. natural rock flour, such as kaolins, clays, talc, chalk, Quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic powdered rock, such as finely divided Silica, alumina and silicates.
Als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylary!polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate. Als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfatablaugen und Methylcellulose.Suitable emulsifiers and / or foam-generating agents are: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylary! polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates as well as protein hydrolysates. Possible dispersants are: e.g. lignin sulphate waste liquors and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-like polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and Lecithins and synthetic phospholipids. Further additives can be mineral and vegetable oils.
Le A 23 287Le A 23 287
-Ab-Away
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metal!phthalocyaninfarbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc be used.
Die erfindungsgemäßen Wirkstoffe können in den Formulierungen in Mischung mit anderen bekannten Wirkstoffen vorliegen, wie Fungizide, Insektizide, Akarizide und Herbizide, sowie in Mischungen mit Düngemitteln und Wachstumsregulatoren.The active compounds according to the invention can be used in the formulations be present as a mixture with other known active ingredients, such as fungicides, insecticides, acaricides and herbicides, as well as in mixtures with fertilizers and growth regulators.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, emulgierbare Konzentrate, Emulsionen, Schäume, Spritzpulver, Pasten, lösliche Pulver und Stäubemittel angewenset werden, Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volumen-Verfahren aus zubr ingen.The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, wettable powders, pastes, soluble ones Powder and dust are used, the application is done in the usual way, e.g. by pouring, Splashing, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible the active ingredients according to the ultra-low-volume method from zubr ingen.
Die erfindungsgemäßen selektiv-fungiziden Mittel enthalten im allgemeinen 10 bis 100 Gew.-%, bevorzugt 30 bis 100 Gew.-%, an Salzen der Formel (I) als Wirkstoff.The selective fungicidal agents according to the invention generally contain 10 to 100% by weight, preferably 30 to 100% by weight, of salts of the formula (I) as active ingredient.
Le A 23 287Le A 23 287
Bei der Behandlung von Pflanzenteilen können die Wirkstoff konzentrat ionen in den Anwendungsformen in einem größeren Bereich variiert werden. Sie liegen im allgemeinen zwischen 1 und 0,0001 Gew.-%, vorzugsweise zwischen 0,5 und 0,001 %.In the treatment of parts of plants, the active ingredient can concentrate ions in the use forms in one can be varied in a larger area. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
Le A 23 287Le A 23 287
3U5853 - xs -3U5853 - xs -
Als Vergleichssubstanz wird die folgende .Verbindung, die als Wirkstoff zur Bekämpfung von Oomyceten alt bekannt ist, herangezogen:The following compound is used as a comparison substance, which is used as an active ingredient to combat Oomycetes old is known, used:
?3? 3
(-S-CS-NH-CH2-CH-Nh-CS-S-)2Zn(-S-CS-NH-CH 2 -CH-Nh-CS-S-) 2 Zn
Zink-(N,N'-propylen-1,2-bis-dithiocarbamat).Zinc (N, N'-propylene-1,2-bis-dithiocarbamate).
Le A 23 287Le A 23 287
-TA--TA-
Falscher Mehltau-Test Pseudoperonospora cubensis Test (Gurke)Downy mildew test Pseudoperonospora cubensis test (cucumber)
Die gewünschte Wirkstoffkonzentration wird eingestellt, indem in einer vorgegebenen Wassermenge die erforderliche Substanzmenge gelöst wird.The desired concentration of active ingredient is set, by dissolving the required amount of substance in a given amount of water.
Mit der Spritzflüssigkeit bespritzt man Gurkenpflanzen bis zur Tropfnässe und setzt sie danach natürlichen Infektionsbedingungen aus. In jeweils 1-wöchigen Ab-The spray liquid is used to spray cucumber plants until they are dripping wet and then set them naturally Infection conditions. Every 1-week
10 ständen wird die Behandlung noch 2 mal wiederholt.The treatment is repeated two more times.
Eine Woche nach der letzten Behandlung wird der Befall der Pflanzen bestimmt. Die erhaltenen Boniturwerte werden in Prozent Befall ausgedrückt. 0 % bedeutet keinen Befall, 100 % bedeutet, daß die PflanzenThe infestation of the plants is determined one week after the last treatment. The obtained rating values are expressed as a percentage of infestation. 0% means no infestation, 100% means that the plants
15 vollständig befallen sind.15 are completely infected.
Le A 23 287Le A 23 287
WirkstoffActive ingredient
Pseudoperonospora cubensis-Test (Gurke)Pseudoperonospora cubensis test (cucumber)
Konzentration in ppm Befall in % der unbehandelten KontrolleConcentration in ppm infestation in% of the untreated control
unbehandeltuntreated
(-S-CS-NH-Ch2-CH-NH-CS-S-)2Zn (bekannt)(-S-CS-NH-Ch 2 -CH-NH-CS-S-) 2 Zn (known)
Wirkstoff gemäß Beispiel 2 Θ Wirkstoff gemäß Beispiel 1 ®Active ingredient according to Example 2 Θ Active ingredient according to Example 1 ®
13501350
400 400 100 0,1400 400 100 0.1
2,0 0,52.0 0.5
Zusammensetzung siehe Text SeiteComposition see text on page
Claims (10)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445853 DE3445853A1 (en) | 1984-12-15 | 1984-12-15 | Selective fungicides |
| IT23063/85A IT1201504B (en) | 1984-12-15 | 1985-12-03 | FUNGICID-SELECTIVE MEDIA |
| GR852978A GR852978B (en) | 1984-12-15 | 1985-12-12 | |
| FR8518503A FR2574626A1 (en) | 1984-12-15 | 1985-12-13 | Selective oomycetes control fungicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445853 DE3445853A1 (en) | 1984-12-15 | 1984-12-15 | Selective fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3445853A1 true DE3445853A1 (en) | 1986-06-19 |
Family
ID=6252900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843445853 Withdrawn DE3445853A1 (en) | 1984-12-15 | 1984-12-15 | Selective fungicides |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE3445853A1 (en) |
| FR (1) | FR2574626A1 (en) |
| GR (1) | GR852978B (en) |
| IT (1) | IT1201504B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080673A1 (en) * | 2001-04-06 | 2002-10-17 | Brouard, Rodney, Walter | Plant invigorator |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1462043A (en) * | 1973-02-22 | 1977-01-19 | Ici Ltd | Process for combating fungi |
| JPS55111403A (en) * | 1979-02-21 | 1980-08-28 | Rikagaku Kenkyusho | Antimicrobial for agriculture and horticulture |
| DE3111934A1 (en) * | 1981-03-26 | 1982-10-07 | Bayer Ag, 5090 Leverkusen | OIL-IN-WATER EMULSIONS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
-
1984
- 1984-12-15 DE DE19843445853 patent/DE3445853A1/en not_active Withdrawn
-
1985
- 1985-12-03 IT IT23063/85A patent/IT1201504B/en active
- 1985-12-12 GR GR852978A patent/GR852978B/el unknown
- 1985-12-13 FR FR8518503A patent/FR2574626A1/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080673A1 (en) * | 2001-04-06 | 2002-10-17 | Brouard, Rodney, Walter | Plant invigorator |
| AP1805A (en) * | 2001-04-06 | 2007-12-11 | Rodney Walter Brouard | Plant invigorator. |
| HRP20030897B1 (en) * | 2001-04-06 | 2012-03-31 | Brouard | Plant invigorator |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2574626A1 (en) | 1986-06-20 |
| IT1201504B (en) | 1989-02-02 |
| GR852978B (en) | 1986-04-08 |
| IT8523063A0 (en) | 1985-12-03 |
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