DE3910921C1 - - Google Patents
Info
- Publication number
- DE3910921C1 DE3910921C1 DE3910921A DE3910921A DE3910921C1 DE 3910921 C1 DE3910921 C1 DE 3910921C1 DE 3910921 A DE3910921 A DE 3910921A DE 3910921 A DE3910921 A DE 3910921A DE 3910921 C1 DE3910921 C1 DE 3910921C1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dimethyl
- dodecyl
- weight
- triazol
- 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
- 239000007921 spray Substances 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 31
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 7
- NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 claims description 3
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013543 active substance Substances 0.000 abstract description 6
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 abstract description 5
- -1 N-dodecyl pyrrolidone N-decyl pyrrolidone N-octyl pyrrolidone N-dodecyl valerolactam N-decyl valerolactam N-octyl valerolactam Chemical compound 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000006353 oxyethylene group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- FYEJWUXIXSNIDI-UHFFFAOYSA-N 2-aminoethanol;4-dodecylbenzenesulfonic acid Chemical compound NCCO.CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 FYEJWUXIXSNIDI-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000005086 pumping Methods 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N Heptyl acetate Chemical compound CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- IQAXZJZTCMIPCX-UHFFFAOYSA-L calcium;4-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 IQAXZJZTCMIPCX-UHFFFAOYSA-L 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- YUFSXAHJVSZFRA-NTSWFWBYSA-N (1s,2r)-2-n-(1,1,2,2-tetrachloroethylsulfanyl)cyclohex-4-ene-1,2-dicarboxamide Chemical compound NC(=O)[C@H]1CC=CC[C@H]1C(=O)NSC(Cl)(Cl)C(Cl)Cl YUFSXAHJVSZFRA-NTSWFWBYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- SFVAIECZMIFQIA-UHFFFAOYSA-N 1,3-dichloro-n-(2-chlorophenyl)-2h-1,2,4-triazin-5-amine Chemical compound ClN1NC(Cl)=NC(NC=2C(=CC=CC=2)Cl)=C1 SFVAIECZMIFQIA-UHFFFAOYSA-N 0.000 description 1
- QQJIRQMOCFESJB-UHFFFAOYSA-N 1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound CCC(O)CN1C=NC=N1 QQJIRQMOCFESJB-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- PASAPCUFEQGBFP-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(triazol-1-ylmethyl)pentan-3-ol Chemical compound ClC1=CC=C(C=C1)CCC(C(C)(C)C)(O)CN1N=NC=C1 PASAPCUFEQGBFP-UHFFFAOYSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- VKAMZEDHHWTTNZ-UHFFFAOYSA-N 1-octylazepan-2-one Chemical compound CCCCCCCCN1CCCCCC1=O VKAMZEDHHWTTNZ-UHFFFAOYSA-N 0.000 description 1
- KIHJEJVWUXTXPZ-UHFFFAOYSA-N 2-(3,5-dichlorophenylcarbamoyl)-1,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 KIHJEJVWUXTXPZ-UHFFFAOYSA-N 0.000 description 1
- VBSCXNZULFIXIJ-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-2-prop-2-enoxyethyl]-1h-imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CC1=NC=CN1 VBSCXNZULFIXIJ-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
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
- VYFCWUVTRWLLFW-UHFFFAOYSA-N 2-n-(trichloromethylsulfanyl)cyclohex-4-ene-1,2-dicarboxamide Chemical compound NC(=O)C1CC=CCC1C(=O)NSC(Cl)(Cl)Cl VYFCWUVTRWLLFW-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- JHWLWOYSFJIYQV-UHFFFAOYSA-N 4-dodecylbenzenesulfonate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHWLWOYSFJIYQV-UHFFFAOYSA-N 0.000 description 1
- ILSKETFHULOIOY-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid;2-(2-hydroxyethylamino)ethanol Chemical compound OCCNCCO.CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 ILSKETFHULOIOY-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- YCSMVPSDJIOXGN-UHFFFAOYSA-N CCCCCCCCCCCC[Na] Chemical compound CCCCCCCCCCCC[Na] YCSMVPSDJIOXGN-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005802 Mancozeb 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- WHHNSIKOZDDUTR-UHFFFAOYSA-N O(C)C=1NC2=C(N1)C=CC=C2C(=O)N Chemical compound O(C)C=1NC2=C(N1)C=CC=C2C(=O)N WHHNSIKOZDDUTR-UHFFFAOYSA-N 0.000 description 1
- ZJVKLBBPLUXEAC-UHFFFAOYSA-N Pipethanate hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(=O)OCC[NH+]1CCCCC1 ZJVKLBBPLUXEAC-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates 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
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- KKBKMPQHDSDUJI-UHFFFAOYSA-N azanium;4-dodecylbenzenesulfonate Chemical compound [NH4+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 KKBKMPQHDSDUJI-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 229920000940 maneb Polymers 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 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
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- XGIOPUDVLLKCFN-UHFFFAOYSA-M sodium;4-nonylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 XGIOPUDVLLKCFN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3910921A DE3910921C1 (en, 2012) | 1989-04-05 | 1989-04-05 | |
| AT90105510T ATE76254T1 (de) | 1989-04-05 | 1990-03-23 | Verwendung von n-alkyl-lactamen als kristallisationsinhibitoren. |
| EP90105510A EP0391168B1 (de) | 1989-04-05 | 1990-03-23 | Verwendung von N-Alkyl-lactamen als Kristallisationsinhibitoren |
| ES90105510T ES2043157T3 (es) | 1989-04-05 | 1990-03-23 | Empleo de n-alquil-lactamas como inhibidores de cristalizacion. |
| DE9090105510T DE59000129D1 (de) | 1989-04-05 | 1990-03-23 | Verwendung von n-alkyl-lactamen als kristallisationsinhibitoren. |
| DK90105510.3T DK0391168T3 (da) | 1989-04-05 | 1990-03-23 | Anvendelse af N-alkyl-lactamer som krystallisationsinhibitorer |
| US07/502,369 US5369118A (en) | 1989-04-05 | 1990-03-30 | N-alkyl-lactams as crystallization inhibitors |
| JP2085085A JP2894622B2 (ja) | 1989-04-05 | 1990-04-02 | Ｎ―アルキル―ラクタムの使用 |
| CA002013729A CA2013729C (en) | 1989-04-05 | 1990-04-03 | Use of n-alkyl-lactams as crystallization inhibitors |
| BR909001528A BR9001528A (pt) | 1989-04-05 | 1990-04-03 | Utilizacao de n-alquil-lactamas e processo para evitar a cristalizacao de substancias ativas |
| HU902078A HU204406B (en) | 1989-04-05 | 1990-04-04 | Fungicide spray composition containing inhibitor against cristallization and process for producing the spray composition |
| ZA902586A ZA902586B (en) | 1989-04-05 | 1990-04-04 | Use of n-alkyl-lactams as crystallization inhibitors |
| AU52590/90A AU618889B2 (en) | 1989-04-05 | 1990-04-04 | Use of n-alkyl-lactams as crystallization inhibitors |
| MX020079A MX171046B (es) | 1989-04-05 | 1990-04-28 | Procedimiento para impedir la cristalizacion de formulaciones acuosas a base de productos activos fungicidas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3910921A DE3910921C1 (en, 2012) | 1989-04-05 | 1989-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3910921C1 true DE3910921C1 (en, 2012) | 1990-05-17 |
Family
ID=6377858
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3910921A Expired - Lifetime DE3910921C1 (en, 2012) | 1989-04-05 | 1989-04-05 | |
| DE9090105510T Expired - Lifetime DE59000129D1 (de) | 1989-04-05 | 1990-03-23 | Verwendung von n-alkyl-lactamen als kristallisationsinhibitoren. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE9090105510T Expired - Lifetime DE59000129D1 (de) | 1989-04-05 | 1990-03-23 | Verwendung von n-alkyl-lactamen als kristallisationsinhibitoren. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5369118A (en, 2012) |
| EP (1) | EP0391168B1 (en, 2012) |
| JP (1) | JP2894622B2 (en, 2012) |
| AT (1) | ATE76254T1 (en, 2012) |
| AU (1) | AU618889B2 (en, 2012) |
| BR (1) | BR9001528A (en, 2012) |
| CA (1) | CA2013729C (en, 2012) |
| DE (2) | DE3910921C1 (en, 2012) |
| DK (1) | DK0391168T3 (en, 2012) |
| ES (1) | ES2043157T3 (en, 2012) |
| HU (1) | HU204406B (en, 2012) |
| MX (1) | MX171046B (en, 2012) |
| ZA (1) | ZA902586B (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT4301B (lt) | 1994-10-11 | 1998-03-25 | Basf Aktiengesellschaft | Stabilus vandeninis mišinys, turintis metazachloro |
| DE102009000505A1 (de) | 2009-01-30 | 2010-08-05 | Evonik Goldschmidt Gmbh | Zusammensetzungen enthaltend Reaktionsprodukte aus Alkylamidoaminen, Alkylaminoimidazolinen und freiem Amin sowie deren Verwendung |
| EP2335480A1 (en) * | 2009-12-15 | 2011-06-22 | Cognis IP Management GmbH | Biocide compositions comprising derivatives of pyroglutamic acid |
| WO2014118240A1 (en) * | 2013-02-01 | 2014-08-07 | Unilever Plc | Antimicrobial composition comprising a lactam and a hydrotrope |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3910992A1 (de) * | 1989-04-05 | 1990-11-08 | Boewe Passat Reinigung | Vorrichtung zum befuellen eines behaelters |
| US5156666A (en) * | 1989-12-11 | 1992-10-20 | Isp Investments Inc. | Delivery system for agricultural chemicals |
| DE4013523A1 (de) * | 1990-04-27 | 1991-10-31 | Bayer Ag | Verwendung von n-alkyl-lactamen als kristallisationsinhibitoren |
| DE4013522A1 (de) * | 1990-04-27 | 1991-10-31 | Bayer Ag | Verwendung von alkylcarbonsaeure-dimethylamiden als kristallisationsinhibitoren |
| DE4013524A1 (de) * | 1990-04-27 | 1991-10-31 | Bayer Ag | Verwendung von kupfersalzen als kristallisationsinhibitoren |
| EP0574492B1 (en) * | 1991-02-12 | 1999-05-12 | Isp Investments Inc. | Stabilization of microemulsions using hydrophobic acid buffers |
| DE4319263A1 (de) † | 1992-07-03 | 1994-01-05 | Schoenherr Joerg | Pflanzenbehandlungsmittel |
| ES2117748T3 (es) * | 1993-11-16 | 1998-08-16 | Bayer Ag | Empleo de esteres del acido fosforico como inhibidores de cristalizacion. |
| IL148684A (en) * | 2002-03-14 | 2006-12-31 | Yoel Sasson | Pesticidal composition |
| CA2619018A1 (en) * | 2005-09-05 | 2007-03-15 | Cheminova A/S | Concentrated liquid triazole-fungicide formulations |
| CN101069501A (zh) * | 2007-05-28 | 2007-11-14 | 江苏龙灯化学有限公司 | 双取代长链烷基酰胺类作为结晶抑制剂在唑类农药液剂中的应用 |
| JP5668281B2 (ja) * | 2009-09-10 | 2015-02-12 | 住友化学株式会社 | マイクロカプセルおよびその製造方法 |
| AR079732A1 (es) * | 2009-12-30 | 2012-02-15 | Akzo Nobel Chemicals Int Bv | Amidas, uso de amidas como solventes para compuestos organicos, composiciones y emulsiones que contienen amidas, y metodo de elaboracion |
| US10662151B1 (en) | 2017-12-30 | 2020-05-26 | Amsa, Inc. | Process for preparing DTEA HCl |
| AR121140A1 (es) * | 2020-01-28 | 2022-04-20 | Adama Makhteshim Ltd | Composición agroquímica de triazoles |
| EP3888463A1 (en) | 2020-04-02 | 2021-10-06 | Rotam Agrochem International Company Limited | Crystallization inhibitors for triazole pesticide formulations |
| EP3888464A1 (en) * | 2020-04-02 | 2021-10-06 | Rotam Agrochem International Company Limited | Plant protection composition having improved penetration |
| BR112022026637A2 (pt) | 2020-06-29 | 2023-01-24 | Basf Se | Composição, uso de um sistema solvente para preparar um concentrado emulsionável, métodos de preparação de uma composição e de tratamento de solo e plantas, composição de emulsão, processo para preparar uma composição de emulsão, e, uso da composição de emulsão |
| WO2023099366A1 (en) | 2021-12-01 | 2023-06-08 | Basf Se | Biocide compositions |
| WO2024018453A1 (en) * | 2022-07-21 | 2024-01-25 | Adama Makhteshim Ltd. | Compositions of triazole fungicides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988000184A1 (en) * | 1986-06-27 | 1988-01-14 | Gaf Corporation | Surface active lactams |
| US4762549A (en) * | 1982-09-30 | 1988-08-09 | Nelson Research & Development Co. | Delivery of plant growth regulators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1160268B (de) | 1954-02-27 | 1963-12-27 | Basf Ag | Mittel zum Schutz von Metalloberflaechen gegen Spannungskorrosion |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| US4525199A (en) | 1981-05-04 | 1985-06-25 | Nelson Research & Development Co. | Method of improved pest control |
| US4461638A (en) * | 1975-06-19 | 1984-07-24 | Nelson Research & Development Company | Delivery of plant nutrients |
| AU542623B2 (en) | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| US4348385A (en) * | 1980-11-17 | 1982-09-07 | Mobay Chemical Corporation | Flowable pesticides |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| DE3308850C2 (de) * | 1983-03-12 | 1985-03-07 | B. Braun Melsungen Ag, 3508 Melsungen | Bleich-, Reinigungs- und Desinfektionsmittel auf Hypohalitbasis mit verbesserter Lagerstabilität |
| DE3333411A1 (de) * | 1983-09-16 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
| DE3910992A1 (de) * | 1989-04-05 | 1990-11-08 | Boewe Passat Reinigung | Vorrichtung zum befuellen eines behaelters |
-
1989
- 1989-04-05 DE DE3910921A patent/DE3910921C1/de not_active Expired - Lifetime
-
1990
- 1990-03-23 ES ES90105510T patent/ES2043157T3/es not_active Expired - Lifetime
- 1990-03-23 AT AT90105510T patent/ATE76254T1/de not_active IP Right Cessation
- 1990-03-23 DK DK90105510.3T patent/DK0391168T3/da active
- 1990-03-23 DE DE9090105510T patent/DE59000129D1/de not_active Expired - Lifetime
- 1990-03-23 EP EP90105510A patent/EP0391168B1/de not_active Expired - Lifetime
- 1990-03-30 US US07/502,369 patent/US5369118A/en not_active Expired - Lifetime
- 1990-04-02 JP JP2085085A patent/JP2894622B2/ja not_active Expired - Lifetime
- 1990-04-03 CA CA002013729A patent/CA2013729C/en not_active Expired - Lifetime
- 1990-04-03 BR BR909001528A patent/BR9001528A/pt not_active IP Right Cessation
- 1990-04-04 ZA ZA902586A patent/ZA902586B/xx unknown
- 1990-04-04 HU HU902078A patent/HU204406B/hu unknown
- 1990-04-04 AU AU52590/90A patent/AU618889B2/en not_active Expired
- 1990-04-28 MX MX020079A patent/MX171046B/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762549A (en) * | 1982-09-30 | 1988-08-09 | Nelson Research & Development Co. | Delivery of plant growth regulators |
| WO1988000184A1 (en) * | 1986-06-27 | 1988-01-14 | Gaf Corporation | Surface active lactams |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT4301B (lt) | 1994-10-11 | 1998-03-25 | Basf Aktiengesellschaft | Stabilus vandeninis mišinys, turintis metazachloro |
| DE102009000505A1 (de) | 2009-01-30 | 2010-08-05 | Evonik Goldschmidt Gmbh | Zusammensetzungen enthaltend Reaktionsprodukte aus Alkylamidoaminen, Alkylaminoimidazolinen und freiem Amin sowie deren Verwendung |
| EP2223601A1 (de) | 2009-01-30 | 2010-09-01 | Evonik Goldschmidt GmbH | Zusammensetzungen enthaltend Reaktionsprodukte aus Alkylamidoaminen, Alkylaminoimidazolinen und freiem Amin sowie deren Verwendung |
| EP2335480A1 (en) * | 2009-12-15 | 2011-06-22 | Cognis IP Management GmbH | Biocide compositions comprising derivatives of pyroglutamic acid |
| WO2011072811A3 (en) * | 2009-12-15 | 2012-03-29 | Cognis Ip Management Gmbh | Biocide compositions comprising derivatives of pyroglutamic acid |
| US8927460B2 (en) | 2009-12-15 | 2015-01-06 | Cognis Ip Management Gmbh | Biocide compositions comprising derivatives of pyroglutamic acid |
| WO2014118240A1 (en) * | 2013-02-01 | 2014-08-07 | Unilever Plc | Antimicrobial composition comprising a lactam and a hydrotrope |
| US9930888B2 (en) | 2013-02-01 | 2018-04-03 | Conopco, Inc. | Composition |
Also Published As
| Publication number | Publication date |
|---|---|
| AU618889B2 (en) | 1992-01-09 |
| DK0391168T3 (da) | 1992-07-13 |
| MX171046B (es) | 1993-09-27 |
| JP2894622B2 (ja) | 1999-05-24 |
| ZA902586B (en) | 1991-01-30 |
| HU204406B (en) | 1992-01-28 |
| EP0391168B1 (de) | 1992-05-20 |
| JPH02290802A (ja) | 1990-11-30 |
| ES2043157T3 (es) | 1993-12-16 |
| US5369118A (en) | 1994-11-29 |
| ATE76254T1 (de) | 1992-06-15 |
| CA2013729C (en) | 2000-02-29 |
| EP0391168A1 (de) | 1990-10-10 |
| DE59000129D1 (de) | 1992-06-25 |
| HU902078D0 (en) | 1990-07-28 |
| AU5259090A (en) | 1990-10-11 |
| CA2013729A1 (en) | 1990-10-05 |
| BR9001528A (pt) | 1991-04-23 |
| HUT53785A (en) | 1990-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |