JP2894622B2 - Ｎ―アルキル―ラクタムの使用 - Google Patents
Ｎ―アルキル―ラクタムの使用Info
- Publication number
- JP2894622B2 JP2894622B2 JP2085085A JP8508590A JP2894622B2 JP 2894622 B2 JP2894622 B2 JP 2894622B2 JP 2085085 A JP2085085 A JP 2085085A JP 8508590 A JP8508590 A JP 8508590A JP 2894622 B2 JP2894622 B2 JP 2894622B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- dimethyl
- 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 48
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 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 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 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 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000007788 liquid Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 6
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical group CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 claims description 3
- LSCXTKOQDSGGPT-UHFFFAOYSA-N 6-(1,2,4-triazol-1-yl)hexan-3-ol Chemical compound CCC(O)CCCN1C=NC=N1 LSCXTKOQDSGGPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 239000013543 active substance Substances 0.000 abstract 2
- -1 4-chlorophenoxy Chemical group 0.000 description 20
- 125000006353 oxyethylene group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
- 238000002156 mixing Methods 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
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000004094 surface-active agent Substances 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005802 Mancozeb Substances 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 230000000875 corresponding effect Effects 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
- 239000012990 dithiocarbamate Substances 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
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
- SLBKGBQKBVOZRI-UHFFFAOYSA-N 1,2-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CC1(C)C(O)=O SLBKGBQKBVOZRI-UHFFFAOYSA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- LHTJITWSNBQNJM-UHFFFAOYSA-N 1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CCC(=O)CN1C=NC=N1 LHTJITWSNBQNJM-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
- 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
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- 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
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-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
- 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
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- 239000005777 Fenpropidin 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
- 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 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
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JYBGVFYNRAPJRJ-UHFFFAOYSA-N [1-(butylcarbamoyl)benzimidazol-2-yl]carbamic acid Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(O)=O)=NC2=C1 JYBGVFYNRAPJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N acetic acid heptyl ester Natural products CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 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
- 230000001276 controlling effect Effects 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 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
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 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
- 230000000855 fungicidal effect Effects 0.000 description 1
- JPXGPRBLTIYFQG-UHFFFAOYSA-N heptan-4-yl acetate Chemical compound CCCC(CCC)OC(C)=O JPXGPRBLTIYFQG-UHFFFAOYSA-N 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
- 239000004615 ingredient Substances 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
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000002480 mineral oil Substances 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
- 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
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 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
- 238000005086 pumping Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 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
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3910921A DE3910921C1 (en, 2012) | 1989-04-05 | 1989-04-05 | |
| DE3910921.6 | 1989-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02290802A JPH02290802A (ja) | 1990-11-30 |
| JP2894622B2 true JP2894622B2 (ja) | 1999-05-24 |
Family
ID=6377858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2085085A Expired - Lifetime JP2894622B2 (ja) | 1989-04-05 | 1990-04-02 | Ｎ―アルキル―ラクタムの使用 |
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) |
Families Citing this family (24)
| 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 |
| WO1992013454A1 (en) * | 1991-02-12 | 1992-08-20 | 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. |
| DE4436293A1 (de) | 1994-10-11 | 1996-04-18 | Basf Ag | Stabile Mischung, welche Wasser und Metazachlor enthält |
| IL148684A (en) * | 2002-03-14 | 2006-12-31 | Yoel Sasson | Pesticidal composition |
| BRPI0520511A2 (pt) * | 2005-09-05 | 2009-05-12 | Cheminova As | formulações lìquidas concentradas de fungicidas triazólicos |
| 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 |
| DE102009000505A1 (de) | 2009-01-30 | 2010-08-05 | Evonik Goldschmidt Gmbh | Zusammensetzungen enthaltend Reaktionsprodukte aus Alkylamidoaminen, Alkylaminoimidazolinen und freiem Amin sowie deren Verwendung |
| 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 |
| EP2335480A1 (en) * | 2009-12-15 | 2011-06-22 | Cognis IP Management GmbH | Biocide compositions comprising derivatives of pyroglutamic acid |
| US8900612B2 (en) * | 2009-12-30 | 2014-12-02 | Akzo Nobel Chemicals International B.V. | Amides, use of amides as solvents for organic compounds, compositions and emulsions containing amides, and method for treating a plant |
| DE212014000038U1 (de) * | 2013-02-01 | 2015-09-21 | Unilever N.V. | Zusammensetzung |
| 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 |
| EP3888464A1 (en) * | 2020-04-02 | 2021-10-06 | Rotam Agrochem International Company Limited | Plant protection composition having improved penetration |
| EP3888463A1 (en) * | 2020-04-02 | 2021-10-06 | Rotam Agrochem International Company Limited | Crystallization inhibitors for triazole pesticide formulations |
| AU2021301088A1 (en) | 2020-06-29 | 2023-02-02 | Basf Se | Biocide compositions |
| US20250008950A1 (en) | 2021-12-01 | 2025-01-09 | Basf Se | Biocide compositions |
| WO2024018453A1 (en) * | 2022-07-21 | 2024-01-25 | Adama Makhteshim Ltd. | Compositions of triazole fungicides |
Family Cites Families (12)
| 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 |
| US4762549A (en) * | 1982-09-30 | 1988-08-09 | Nelson Research & Development Co. | Delivery of plant growth regulators |
| 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 |
| EP0311632B1 (en) * | 1986-06-27 | 1996-05-29 | Isp Investments Inc. | Surface active lactams |
| 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 EP EP90105510A patent/EP0391168B1/de not_active Expired - Lifetime
- 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 DE DE9090105510T patent/DE59000129D1/de not_active Expired - Lifetime
- 1990-03-23 DK DK90105510.3T patent/DK0391168T3/da active
- 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 BR BR909001528A patent/BR9001528A/pt not_active IP Right Cessation
- 1990-04-03 CA CA002013729A patent/CA2013729C/en not_active Expired - Lifetime
- 1990-04-04 HU HU902078A patent/HU204406B/hu unknown
- 1990-04-04 AU AU52590/90A patent/AU618889B2/en not_active Expired
- 1990-04-04 ZA ZA902586A patent/ZA902586B/xx unknown
- 1990-04-28 MX MX020079A patent/MX171046B/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2013729C (en) | 2000-02-29 |
| MX171046B (es) | 1993-09-27 |
| DK0391168T3 (da) | 1992-07-13 |
| CA2013729A1 (en) | 1990-10-05 |
| ZA902586B (en) | 1991-01-30 |
| AU5259090A (en) | 1990-10-11 |
| EP0391168A1 (de) | 1990-10-10 |
| HUT53785A (en) | 1990-12-28 |
| BR9001528A (pt) | 1991-04-23 |
| DE59000129D1 (de) | 1992-06-25 |
| ES2043157T3 (es) | 1993-12-16 |
| EP0391168B1 (de) | 1992-05-20 |
| HU902078D0 (en) | 1990-07-28 |
| DE3910921C1 (en, 2012) | 1990-05-17 |
| AU618889B2 (en) | 1992-01-09 |
| JPH02290802A (ja) | 1990-11-30 |
| US5369118A (en) | 1994-11-29 |
| ATE76254T1 (de) | 1992-06-15 |
| HU204406B (en) | 1992-01-28 |
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