US3127311A - Fungicidal compositions - Google Patents
Fungicidal compositions Download PDFInfo
- Publication number
- US3127311A US3127311A US3127311DA US3127311A US 3127311 A US3127311 A US 3127311A US 3127311D A US3127311D A US 3127311DA US 3127311 A US3127311 A US 3127311A
- Authority
- US
- United States
- Prior art keywords
- acid
- fatty
- compositions
- polyglycol
- organic
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 38
- 230000000855 fungicidal effect Effects 0.000 title claims description 15
- 229920000151 polyglycol Polymers 0.000 claims description 27
- 239000010695 polyglycol Substances 0.000 claims description 27
- 239000000417 fungicide Substances 0.000 claims description 25
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 150000002170 ethers Chemical class 0.000 claims description 11
- 150000004665 fatty acids Chemical class 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- -1 PHENYL HYDROXY Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 229920001522 polyglycol ester Polymers 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 26
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 235000019359 magnesium stearate Nutrition 0.000 description 13
- 235000012239 silicon dioxide Nutrition 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
- 229960004889 salicylic acid Drugs 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 5
- 229960002447 thiram Drugs 0.000 description 5
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000003827 glycol group Chemical group 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 150000004653 carbonic acids Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GJJSIBHNXGFVAA-FOCLMDBBSA-N (E)-3-(dinitromethyl)-4-methyl-2-phenyldec-2-enoic acid Chemical compound CCCCCCC(C)C(\C([N+]([O-])=O)[N+]([O-])=O)=C(/C(O)=O)C1=CC=CC=C1 GJJSIBHNXGFVAA-FOCLMDBBSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SKKUAUZTZZRYPW-UHFFFAOYSA-N 1-chloro-2,4-dinitronaphthalene Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CC([N+]([O-])=O)=C21 SKKUAUZTZZRYPW-UHFFFAOYSA-N 0.000 description 1
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- GFOIDJBFWHYEIU-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;sodium Chemical compound [Na].[Na].NC(=S)SCCSC(N)=S GFOIDJBFWHYEIU-UHFFFAOYSA-N 0.000 description 1
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- KKADPXVIOXHVKN-UHFFFAOYSA-N 4-hydroxyphenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=C(O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 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
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000010933 magnesium salts of fatty acid Nutrition 0.000 description 1
- 239000001778 magnesium salts of fatty acids 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [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
- 230000007246 mechanism Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl 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])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
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide 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
- 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
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N25/12—Powders or granules
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/09—Fish posts
Definitions
- the present invention relates to and has as its objects new and useful compositions of organic fungicides, which contain in addition to known active fungicides certain special emulsifiers and other adjectives which render the inventive compositions highly active and especially stable.
- the special ingredients contained in the inventively improved fungicidal compositions are fatty alcohol polyglycol ethers or fatty acid polyglycol esters, metal salts, special magnesium salts of fatty acids and lower aliphatic or aromatic poly-basic carbonic acids or hydroxy carbonic acids.
- auxiliary agents in fungicidal compositions especially detergents, emulsifiers, hydrophobating agents, adhesives act on the time of action and rapidity of action in a negative way.
- a theoretical example is the following: If an organic fungicide which acts by its decomposition products is brought into stable formulations, the particles are covered by water impenetrable layers and thereby the micro-particles are not able to be decomposed and there- The purpose of improving 3,127,311 Patented Mar. 31, 1964 by they become inert or less biologically active on the plant.
- compositions of organic fungicides especially improved fungicidal spray compositions broadly may be obtained, if as auxiliary solvents fatty acid metal salts and fatty acid polyglycol esters or fatty alcohol polyglycol ethers or aryl-polyglycol ethers are used. Additionally a certain amount of a solid lower aliphatic dior polycarboxylic acid or an aromatic carboxylic acid should be present in the inventive fungicidal compositions.
- Compositions of the above said type not only have a highly acute activity (rapid action), but they also render the organic fungicides a long lasting activity.
- the compositions of the present invention also secure a good distribution on the plants. A redistribution on the sprayed plant organs by rain water also does not lead to such an amount as this is the case with other known fungicidal compositions.
- the above mentioned polyglycol ethers may be an aryloxypolyglycol ether such as the reaction product of ethylene oxide or propylene oxide or mixtures thereof with phenol, the different cresols, and the like, hydroxy diphenyls (especially 0- or p-hydroxydiphenyl), with benzyl hydroxydiphenyl, and the like.
- aryloxypolyglycol ether such as the reaction product of ethylene oxide or propylene oxide or mixtures thereof with phenol, the different cresols, and the like, hydroxy diphenyls (especially 0- or p-hydroxydiphenyl), with benzyl hydroxydiphenyl, and the like.
- fatty alcohol polyglycol ethers such as the reaction products of C to C alcohols especially C to C alcohols with ethylene oxide or propylene oxide or mixture thereof.
- Those reaction products are e.g. lauryl, stearyl, palmityl or oleyl polyglycol ethers.
- polyglycol ethers there is to be understood a reaction product containing more than at least 2 glycol radicals in the molecule and usually not more than about glycol radicals. Most suitable are the commercially available polyglycol ethers containing average between about 8 to 20 glycol radicals.
- the fatty acid glycerol esters as above mentioned should contain at least one unesterified OH-group. As examples there may be mentioned the lauric acid-glycerol-monoand -diesters, the palmitic acid-glycerol-monoand -diesters, the stearic acid-glyceroldiester (Emocithin) and the like.
- Metal salts of fatty acids in the meaning of this invention are especially salts of C to C carbonic acids and should contain as a salt forming metal especially an alkaline earth metal (magnesium, calcium and the like), zinc, manganese, aluminium, iron, copper and the like.
- Especially useful organic acids are lauric, stearic, palmitic, margaric, oleic, linoleic acid and the like.
- Especially suitable solid lower aliphatic dior polybasic acids which are useful for the inventively used compositions are oxalic acid, maleic acid, succinic acid, adipic acid, malic acid, citric acid, and the like.
- Aromatic acids are especially phthalic acid, salicylic acid, and the like.
- Organic fungicides which may be formulated with the inventively used compositions are broadly the known compounds used in the field of plant protection as yet.
- TMTD tetramethyl-thiuram disulfide, ferric dimethyl dithiocarbamate, manganese ethylene bis-dithiocarbamate, disodium ethylene bis-dithiocarbamate, zinc ethylene bis-dithiocarbamate, zinc dimethyl dithiocarbamate).
- N-trichloromethyl mercaptoA-cyclohexene-l.Z-dicarboximide 2.3-dichloro-l.4-naphthoquinone
- Z-heptadecyl glyoxalidine acetate dinitro-( l-methyl heptyl)-phenyl-crotonate.
- a special advantage of the inventively used combinations is the fact that this combination does not decrease the biological activity, but protects the active compound against influences which ordinarily make the active compound less efiicient. It has even been found that the biological activity is greater than the activity of formulations of known constituents used as yet for practical purposes. A further advantage is the increased period of activity of the inventively used compositions.
- the inventive compositions usually contain the active ingredient in an amount of 5 to 95%, the balance being inert materials and the inventively used additional compounds.
- the polyglycol ether or polyglycol ester compound is present in an amount of 1 to 25% more specifically 2 to 8%.
- the fatty acid salt in the inventively used compositions should be present in an amount of 1 to 15%, especially 2 to 10%.
- the solid hydroxy carboxylic, dicarboxylic or polycarboxylic acid at last is present in an amount up to 10%, es ecially in an amount of 2 to 8%.
- Inert materials used for the inventively described compositions are talc, chalk, kaoline, bentonite, kieselguhr and especially finely divided highly dispersable silicic acids in the form of their various commercially available brands.
- N trichloro methyl-thic-(dimethyl-arninosulfonicacid-anilide) (a) 50.0% of N-trichloro-methyl-thio-(dimethylamino-sulfonic-acid-anilide) 4.0% of oleyl-polyglycol other 1.0% of magnesium stearate 8.0% of salicylic acid Rest finely divided silicic acid 50.0% of N-trichloro-methyl-thio-(dimethylamino sulfonic acid anilide) 10.0% of magnesium stearate 5.0% of decyl-polyglycol ether 8.0% of salicylic acid Rest finely divided silicic acid
- An identical composition may be prepared from: N- tric-hloro-methyl mercapto 4-cyclo-hexene-1.Z-di-carboximide.
- EXAMPLE 5 N-Tric/zlol'o-Methyl-Thio-(Dinlet/1ylamino-Sulfonic Acid Anilide) the same as described before. 5 Active Evaluation number ingredient l3 concc-ntra EXAMPL 1 tion, Un- Sprayed Tcti'amethyl-Thiul'am-D sulfide (TMTD) percent sprayed TEST ([0 Normal formulation (with emulsifier 0.025 7 31 only) 0.0125 2t 50 g t E 1 gg25 3; I; lngrc len va uaconcentration Imeunve combmanon g g numb Non-treated control 100 100 W l 0.025 25 e claim:
- a ⁇ I a G V 1 0.0125 34 59 (0) up to 10% of a solid organic acid this acid being Inventive combmqfion 16 8-83 2 a member selected from the group consisting of a Q 010125 17 43 lower aliphatic dicarboxylic acid, a lower aliphatic Non'tmted comm 100 100 hydroxy-carboxylic acid and salicylic acid,
- EXAMPLE 2 Fungicidal compositions containing an organic 35 fungicide in an amount from 5 to 95 together with r F L Zznc Ethylen BIS Dzthzoca bamate (ZINEB) (a) 2 to 10% OI fatty alcohol p yg y ethers, the fatty alcohol having 12 to 18 carbon atoms and g 'g Evaluatlon numb" being etherified with up to 50 glycol residues, and concentra- (b) 1 to 10% of fatty acid metal salts, the fatty acid g l gg' Sprawl 40 having 12 to 18 carbon atoms and the metal being a member selected from the group consisting of Normal formulation (commercially 0.05 5 15 9319mm, magneslum, Z1I1C and alumlruurn, and I available i 29 (c) up to 10% of a solid organic acid, this acid being 88 g 3 a member selected from the group
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27907A DE1139696B (de) | 1959-03-10 | 1959-03-10 | Fungizide Spritzmittelpulverzubereitungen auf der Basis organischer Wirkstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3127311A true US3127311A (en) | 1964-03-31 |
Family
ID=7092649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3127311D Expired - Lifetime US3127311A (en) | 1959-03-10 | Fungicidal compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3127311A (en)) |
| BE (1) | BE588509A (en)) |
| CH (1) | CH386766A (en)) |
| DE (1) | DE1139696B (en)) |
| GB (1) | GB905695A (en)) |
| NL (1) | NL249291A (en)) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766153A (en) * | 1986-04-30 | 1988-08-23 | Sandoz Ltd. | Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same |
| WO2019077460A1 (en) * | 2017-10-17 | 2019-04-25 | Upl Ltd | NEW AGROCHEMICAL COMBINATIONS |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2696453A (en) * | 1952-05-27 | 1954-12-07 | Herbert L Sanders | Emulsifiers and toxicants containing the same |
| US2731338A (en) * | 1951-01-05 | 1956-01-17 | Monsanto Chemicals | Emulsifying and dispersing agents |
| US2913372A (en) * | 1954-07-23 | 1959-11-17 | Atlas Powder Co | Compositions for dispersing powders in water |
| US2946721A (en) * | 1954-12-17 | 1960-07-26 | Gen Aniline & Film Corp | Emulsification of water-insoluble organic solvents |
-
0
- NL NL249291D patent/NL249291A/xx unknown
- BE BE588509D patent/BE588509A/xx unknown
- US US3127311D patent/US3127311A/en not_active Expired - Lifetime
-
1959
- 1959-03-10 DE DEF27907A patent/DE1139696B/de active Pending
-
1960
- 1960-02-26 CH CH216960A patent/CH386766A/de unknown
- 1960-03-09 GB GB8384/60A patent/GB905695A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731338A (en) * | 1951-01-05 | 1956-01-17 | Monsanto Chemicals | Emulsifying and dispersing agents |
| US2696453A (en) * | 1952-05-27 | 1954-12-07 | Herbert L Sanders | Emulsifiers and toxicants containing the same |
| US2913372A (en) * | 1954-07-23 | 1959-11-17 | Atlas Powder Co | Compositions for dispersing powders in water |
| US2946721A (en) * | 1954-12-17 | 1960-07-26 | Gen Aniline & Film Corp | Emulsification of water-insoluble organic solvents |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766153A (en) * | 1986-04-30 | 1988-08-23 | Sandoz Ltd. | Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same |
| WO2019077460A1 (en) * | 2017-10-17 | 2019-04-25 | Upl Ltd | NEW AGROCHEMICAL COMBINATIONS |
| CN111683531A (zh) * | 2017-10-17 | 2020-09-18 | Upl有限公司 | 新型农用化学品组合 |
| CN115530175A (zh) * | 2017-10-17 | 2022-12-30 | Upl有限公司 | 农用化学品组合 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH386766A (de) | 1965-01-15 |
| BE588509A (en)) | |
| GB905695A (en) | 1962-09-12 |
| DE1139696B (de) | 1962-11-15 |
| NL249291A (en)) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4193993A (en) | Compositions containing preservative metals and their use for the preservation of wood and like materials and as fungicides | |
| US4783221A (en) | Compositions and process for preserving wood | |
| BG37521A3 (bg) | Фунгицидно средство и метод за борба с фунги | |
| US3140977A (en) | Fungicidal compositions containing triphenyl compounds | |
| DE2853040A1 (de) | Mittel zur bekaempfung von phytopathogenen bakterien und pilzen | |
| US3127311A (en) | Fungicidal compositions | |
| DE3023612A1 (de) | Verfahren und fungizides mittel zum konservieren von holz | |
| US2789060A (en) | Pesticidal composition | |
| DE2545148A1 (de) | Fungizide zusammensetzungen auf phosphitbasis | |
| US2338791A (en) | Composition of matter | |
| US2546895A (en) | Aerial disinfectants and method of using the same | |
| PL80654B1 (en)) | ||
| US2204009A (en) | Insecticidal agent | |
| US2631962A (en) | Insecticidal composition comprising a glycol and an insecticidal phosphate | |
| US4870102A (en) | Miticidal composition | |
| US2913369A (en) | Fungicide | |
| DE2515428C2 (de) | Fungicide Zusammensetzungen auf der Basis von Monoaminophosphiten | |
| DD202379A5 (de) | Neue acarizid-zusammensetzung, verfahren zur herstellung und deren verwendung | |
| DE2512556C2 (de) | Cyclische Diphosphorverbindungen, ihre Herstellung und diese enthaltende fungizide Zusammensetzungen | |
| US3417185A (en) | Synergistic biocidal compositions and methods | |
| US3814803A (en) | Stabilized pesticidal compositions containing alkyl dinitrophenyl esters | |
| US2967798A (en) | Insecticidal repellent | |
| DE2805941C2 (de) | Hydraziniumphosphite, ihre Herstellung und funigzide Zusammensetzungen | |
| DE2545150C2 (de) | Fungicide Zusammensetzungen | |
| US4503042A (en) | Acaricide compositions |