CS411386A2 - Fungicide and method of its active substances production - Google Patents

Fungicide and method of its active substances production Download PDF

Info

Publication number: CS411386A2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compound; active ingredient; oxime; composition according
Prior art date: 1985-06-04

Application number

CS864113A

Other languages

Czech (cs)

English (en)

Inventor

Pal Dr Benko

Tibor Dr Zsolnai

Marta Kiniczky

Laszlo Dr Pallos

Iren Dr Zsolnai

Peter Dr Tetenyi

Jeno Dr Bernath

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date 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 date listed.)

1985-06-04

Filing date

1986-06-04

Publication date

1989-09-12

1986-06-04 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1987-10-30 Priority to CS877815A priority Critical patent/CS269996B2/cs

1989-09-12 Publication of CS411386A2 publication Critical patent/CS411386A2/cs

Links

238000000034 method Methods 0.000 title claims description 20
230000000855 fungicidal effect Effects 0.000 title claims description 19
238000004519 manufacturing process Methods 0.000 title claims 3
239000000417 fungicide Substances 0.000 title description 5
239000013543 active substance Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 40
239000004480 active ingredient Substances 0.000 claims description 29
-1 n-butylaminocarbonyl Chemical group 0.000 claims description 26
SFWCXJFWZCIEFJ-UHFFFAOYSA-N ON=C1C(=O)c2ccccc2-c2ccccc12 Chemical compound ON=C1C(=O)c2ccccc2-c2ccccc12 SFWCXJFWZCIEFJ-UHFFFAOYSA-N 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
150000002923 oximes Chemical class 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 4
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000012011 nucleophilic catalyst Substances 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000003512 tertiary amines Chemical group 0.000 claims description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
DCFPNYRFYJWOFR-UHFFFAOYSA-N [(10-oxophenanthren-9-ylidene)amino] n-methylcarbamate Chemical compound C1=CC=C2C(=NOC(=O)NC)C(=O)C3=CC=CC=C3C2=C1 DCFPNYRFYJWOFR-UHFFFAOYSA-N 0.000 claims 1
SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical class C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000008187 granular material Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 5
241000233866 Fungi Species 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000004563 wettable powder Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
241000221576 Uromyces Species 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
150000002987 phenanthrenes Chemical class 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
241000371644 Curvularia ravenelii Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000000440 bentonite Substances 0.000 description 3
229910000278 bentonite Inorganic materials 0.000 description 3
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 3
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 3
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 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
239000008262 pumice Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000123650 Botrytis cinerea Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241001480035 Epidermophyton Species 0.000 description 2
241000221785 Erysiphales Species 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000223238 Trichophyton Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
LFASDCHXZLMSPF-UHFFFAOYSA-N [(10-oxophenanthren-9-ylidene)amino] n-butylcarbamate Chemical compound C1=CC=C2C(=NOC(=O)NCCCC)C(=O)C3=CC=CC=C3C2=C1 LFASDCHXZLMSPF-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
150000008052 alkyl sulfonates Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
229940093476 ethylene glycol Drugs 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
230000001408 fungistatic effect Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000010451 perlite Substances 0.000 description 2
235000019362 perlite Nutrition 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000004576 sand Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229920005552 sodium lignosulfonate Polymers 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-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
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
HMJPSXRANHDJOF-UHFFFAOYSA-N 10-nitrosophenanthren-9-ol Chemical compound C1=CC=C2C(O)=C(N=O)C3=CC=CC=C3C2=C1 HMJPSXRANHDJOF-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
MSUOKLCPGNJGFW-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese;zinc Chemical compound [Mn].[Zn].NC(=S)SCCSC(N)=S MSUOKLCPGNJGFW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000223602 Alternaria alternata Species 0.000 description 1
241000266414 Alternaria crassa Species 0.000 description 1
241001171985 Alternaria papavericola Species 0.000 description 1
241000266345 Alternaria radicina Species 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
MGJGDVZONWZCJP-LGMDPLHJSA-N CCCCCCC(C)/C(\C)=C(\C(O)=O)/C(C([N+]([O-])=O)=C1)=CC=C1[N+]([O-])=O Chemical compound CCCCCCC(C)/C(\C)=C(\C(O)=O)/C(C([N+]([O-])=O)=C1)=CC=C1[N+]([O-])=O MGJGDVZONWZCJP-LGMDPLHJSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
241000222290 Cladosporium Species 0.000 description 1
241000222199 Colletotrichum Species 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
DYMNZCGFRHLNMT-UHFFFAOYSA-N Glyodin Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC1=NCCN1 DYMNZCGFRHLNMT-UHFFFAOYSA-N 0.000 description 1
YDNLKBDXQCHOTH-UHFFFAOYSA-N Halacrinate Chemical compound C1=CC=C2C(Cl)=CC(Br)=C(OC(=O)C=C)C2=N1 YDNLKBDXQCHOTH-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 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
239000005909 Kieselgur Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
241001518729 Monilinia Species 0.000 description 1
241001518836 Monilinia fructigena Species 0.000 description 1
241000862466 Monilinia laxa Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
241000893976 Nannizzia gypsea Species 0.000 description 1
241000189150 Nigrospora Species 0.000 description 1
WDVDKBHSQBLUND-UHFFFAOYSA-N O-[(10-oxophenanthren-9-ylidene)amino] butanethioate Chemical compound C(CC)C(=S)ON=C1C2=CC=CC=C2C=2C=CC=CC=2C1=O WDVDKBHSQBLUND-UHFFFAOYSA-N 0.000 description 1
PGAHJCKRBNDCFD-UHFFFAOYSA-N O-[(10-oxophenanthren-9-ylidene)amino] nonanethioate Chemical compound C(CCCCCCC)C(=S)ON=C1C2=CC=CC=C2C=2C=CC=CC=2C1=O PGAHJCKRBNDCFD-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
240000009164 Petroselinum crispum Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
229930182764 Polyoxin Natural products 0.000 description 1
239000006004 Quartz sand Substances 0.000 description 1
241000813090 Rhizoctonia solani Species 0.000 description 1
OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
241000371621 Stemphylium Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
241000893982 Trichophyton simii Species 0.000 description 1
241000221577 Uromyces appendiculatus Species 0.000 description 1
229930195482 Validamycin Natural products 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
MWDDCFPLFBFZKI-UHFFFAOYSA-N [(10-oxophenanthren-9-ylidene)amino] benzoate Chemical compound O=C1C2=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)C1=CC=CC=C1 MWDDCFPLFBFZKI-UHFFFAOYSA-N 0.000 description 1
QBSZYGVNFQKJEC-UHFFFAOYSA-N [(10-oxophenanthren-9-ylidene)amino] n-(3,4-dichlorophenyl)carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)ON=C1C2=CC=CC=C2C2=CC=CC=C2C1=O QBSZYGVNFQKJEC-UHFFFAOYSA-N 0.000 description 1
WRXXDADMLZZMRL-UHFFFAOYSA-N [1-(butylcarbamoyl)benzimidazol-2-yl] n-methylcarbamate Chemical compound C1=CC=C2N(C(=O)NCCCC)C(OC(=O)NC)=NC2=C1 WRXXDADMLZZMRL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001346 alkyl aryl ethers Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 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
229910052586 apatite Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
MQIVNMHALJNFMG-UHFFFAOYSA-N benquinox Chemical compound C1=CC(=NO)C=CC1=NNC(=O)C1=CC=CC=C1 MQIVNMHALJNFMG-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
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 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
239000004202 carbamide Substances 0.000 description 1
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-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
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012459 cleaning agent Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000002361 compost Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
244000038559 crop plants Species 0.000 description 1
QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
NFZJYJJVHFGPSI-UHFFFAOYSA-H dialuminum;ethyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Al+3].[Al+3].CCP([O-])([O-])=O.CCP([O-])([O-])=O.CCP([O-])([O-])=O NFZJYJJVHFGPSI-UHFFFAOYSA-H 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
LSJJJGKDLSPYCT-UHFFFAOYSA-N ethyl [(10-oxophenanthren-9-ylidene)amino] carbonate Chemical compound C1=CC=C2C(=NOC(=O)OCC)C(=O)C3=CC=CC=C3C2=C1 LSJJJGKDLSPYCT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VHOVSQVSAAQANU-UHFFFAOYSA-M mepiquat chloride Chemical compound [Cl-].C[N+]1(C)CCCCC1 VHOVSQVSAAQANU-UHFFFAOYSA-M 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
HIUQOPYPZTWSRN-UHFFFAOYSA-N o-[(10-oxophenanthren-9-ylidene)amino] propanethioate Chemical compound C1=CC=C2C(=NOC(=S)CC)C(=O)C3=CC=CC=C3C2=C1 HIUQOPYPZTWSRN-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
235000011197 perejil Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000000419 plant extract Substances 0.000 description 1
YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS864113A 1985-06-04 1986-06-04 Fungicide and method of its active substances production CS411386A2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS877815A CS269996B2 (en)	1985-06-04	1987-10-30	Method of phenantherene's new derivatives production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852194A HU196288B (en)	1985-06-04	1985-06-04	Fungicides containing as active substance new derivatives of fenantren and process for production of the active substance

Publications (1)

Publication Number	Publication Date
CS411386A2 true CS411386A2 (en)	1989-09-12

Family

ID=10958225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS864113A CS411386A2 (en)	1985-06-04	1986-06-04	Fungicide and method of its active substances production

Country Status (26)

Country	Link
US (1)	US4746678A (sv)
JP (1)	JPS6248661A (sv)
KR (1)	KR870011083A (sv)
CN (1)	CN86103679A (sv)
AU (1)	AU589637B2 (sv)
BE (1)	BE904865A (sv)
BR (1)	BR8602608A (sv)
CH (1)	CH667645A5 (sv)
CS (1)	CS411386A2 (sv)
DD (2)	DD248357A5 (sv)
DE (1)	DE3618715A1 (sv)
DK (1)	DK262286A (sv)
ES (1)	ES8707711A1 (sv)
FI (1)	FI862382A (sv)
FR (1)	FR2582647B1 (sv)
GB (1)	GB2176186B (sv)
GR (1)	GR861451B (sv)
HU (1)	HU196288B (sv)
IL (1)	IL79029A0 (sv)
IT (1)	IT1204376B (sv)
NL (1)	NL8601435A (sv)
NO (1)	NO862231L (sv)
PL (1)	PL147246B1 (sv)
PT (1)	PT82713B (sv)
SE (1)	SE8602525L (sv)
SU (1)	SU1450737A3 (sv)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3708320A1 (de) *	1987-03-14	1988-09-22	Bayer Ag	Benzaldoxim-derivate
EP1242363B1 (en) *	1999-12-21	2005-11-02	AstraZeneca AB	Cd45 inhibitors
WO2001045680A2 (en) *	1999-12-21	2001-06-28	Astrazeneca Ab	Cd45 inhibitors
KR20090104877A (ko) *	2007-01-23	2009-10-06	후지필름 가부시키가이샤	옥심 화합물, 감광성 조성물, 컬러 필터, 그 제조방법 및 액정표시소자
AR108745A1 (es) *	2016-06-21	2018-09-19	Syngenta Participations Ag	Derivados de oxadiazol microbiocidas
CN106565536B (zh) *	2016-07-15	2018-05-08	广西民族大学	异长叶烯酮肟醚衍生物及其制备方法和应用
CN110156867B (zh) *	2019-06-27	2022-03-25	南京神奇科技开发有限公司	一种氨基甲酸黄柏酮肟酯及其制备方法与应用
GB202014840D0 (en) *	2020-09-21	2020-11-04	Syngenta Crop Protection Ag	Microbiocidal compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL275195A (sv) *	1961-02-28
US3547621A (en) *	1967-05-29	1970-12-15	Gulf Research Development Co	Method of combating weeds
GB1180846A (en) *	1967-08-08	1970-02-11	Agfa Gevaert Nv	Photopolymerisation of Ethylenically Unsaturated Organic Compounds

1985
- 1985-06-04 HU HU852194A patent/HU196288B/hu not_active IP Right Cessation
1986
- 1986-05-31 CN CN198686103679A patent/CN86103679A/zh active Pending
- 1986-06-03 CH CH2249/86A patent/CH667645A5/de not_active IP Right Cessation
- 1986-06-03 BE BE0/216735A patent/BE904865A/fr not_active IP Right Cessation
- 1986-06-04 DD DD86290957A patent/DD248357A5/de not_active IP Right Cessation
- 1986-06-04 GR GR861451A patent/GR861451B/el unknown
- 1986-06-04 GB GB8613531A patent/GB2176186B/en not_active Expired
- 1986-06-04 NO NO862231A patent/NO862231L/no unknown
- 1986-06-04 SU SU864027579A patent/SU1450737A3/ru active
- 1986-06-04 DD DD86301000A patent/DD261083A5/de not_active IP Right Cessation
- 1986-06-04 DE DE19863618715 patent/DE3618715A1/de not_active Withdrawn
- 1986-06-04 CS CS864113A patent/CS411386A2/cs unknown
- 1986-06-04 US US06/870,402 patent/US4746678A/en not_active Expired - Fee Related
- 1986-06-04 PL PL1986259870A patent/PL147246B1/pl unknown
- 1986-06-04 FI FI862382A patent/FI862382A/fi not_active IP Right Cessation
- 1986-06-04 IT IT20666/86A patent/IT1204376B/it active
- 1986-06-04 FR FR8608040A patent/FR2582647B1/fr not_active Expired
- 1986-06-04 SE SE8602525A patent/SE8602525L/sv not_active Application Discontinuation
- 1986-06-04 JP JP61130007A patent/JPS6248661A/ja active Pending
- 1986-06-04 DK DK262286A patent/DK262286A/da not_active Application Discontinuation
- 1986-06-04 IL IL79029A patent/IL79029A0/xx unknown
- 1986-06-04 BR BR8602608A patent/BR8602608A/pt unknown
- 1986-06-04 KR KR1019860004449A patent/KR870011083A/ko not_active Application Discontinuation
- 1986-06-04 PT PT82713A patent/PT82713B/pt unknown
- 1986-06-04 ES ES555709A patent/ES8707711A1/es not_active Expired
- 1986-06-04 AU AU58340/86A patent/AU589637B2/en not_active Ceased
- 1986-06-04 NL NL8601435A patent/NL8601435A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
GR861451B (en)	1986-10-03
DD261083A5 (de)	1988-10-19
IL79029A0 (en)	1986-09-30
FR2582647B1 (fr)	1988-11-18
KR870011083A (ko)	1987-12-19
NL8601435A (nl)	1987-01-02
CN86103679A (zh)	1987-04-08
GB8613531D0 (en)	1986-07-09
SE8602525L (sv)	1986-12-05
GB2176186A (en)	1986-12-17
FI862382A (fi)	1986-12-05
PT82713A (en)	1986-07-01
PT82713B (en)	1987-10-14
IT1204376B (it)	1989-03-01
DE3618715A1 (de)	1986-12-04
DK262286A (da)	1986-12-05
AU5834086A (en)	1986-12-11
IT8620666A0 (it)	1986-06-04
SE8602525D0 (sv)	1986-06-04
NO862231D0 (no)	1986-06-04
BE904865A (fr)	1986-12-03
US4746678A (en)	1988-05-24
GB2176186B (en)	1989-07-05
PL147246B1 (en)	1989-05-31
HU196288B (en)	1988-11-28
ES555709A0 (es)	1987-08-16
BR8602608A (pt)	1987-02-03
HUT40551A (en)	1987-01-28
JPS6248661A (ja)	1987-03-03
FR2582647A1 (fr)	1986-12-05
DK262286D0 (da)	1986-06-04
DD248357A5 (de)	1987-08-05
NO862231L (no)	1986-12-05
ES8707711A1 (es)	1987-08-16
AU589637B2 (en)	1989-10-19
SU1450737A3 (ru)	1989-01-07
FI862382A0 (fi)	1986-06-04
CH667645A5 (de)	1988-10-31

Publication	Publication Date	Title
EP0126254B1 (de)	1987-11-11	N-(2-Nitrophenyl)-4-aminopyrimidin-Derivate als Mikrobizide
EP0135472A2 (de)	1985-03-27	N-(2-Nitrophenyl)-2-aminopyrimidin-Derivate, deren Herstellung und Verwendung
PL112140B1 (en)	1980-09-30	Insecticide
JPS6128668B2 (sv)	1986-07-01
EP0139613A1 (de)	1985-05-02	N-(2-Nitrophenyl)-4-aminopyrimidin-Derivate, deren Herstellung und Verwendung
JPS62212306A (ja)	1987-09-18	殺菌剤としてのシアノピロ−ル誘導体の使用方法
JPS61229876A (ja)	1986-10-14	新規なアニリノベンゾオキソール化合物、その製造方法、及び該化合物を含有する組成物、並びに前記化合物の使用方法
JPH0249281B2 (sv)	1990-10-29
CS411386A2 (en)	1989-09-12	Fungicide and method of its active substances production
HU203270B (en)	1991-07-29	Herbicide compositions containing substituted 2-phenyl-imino-oxazolidines as active components and process for producing the active components
JPH058161B2 (sv)	1993-02-01
JPH0125740B2 (sv)	1989-05-19
JPS635080A (ja)	1988-01-11	２−トリフルオロメチル−ベンズイミダゾ−ル
JPH0421672B2 (sv)	1992-04-13
JPH11508569A (ja)	1999-07-27	トリアゾリン及びイソキサゾリンビス−オキシム誘導体並びに殺虫剤としてのその用途
JPH10509156A (ja)	1998-09-08	Ｏ−ベンジルオキシムエーテル誘導体および有害生物防除剤としてのそれらの使用
CS240991B2 (en)	1986-03-13	Insekticide and akaricide agent and method of effective substances preparation
US4457930A (en)	1984-07-03	Todopropargylsulphamides, microbicidal compositions and use
JPH0248572A (ja)	1990-02-19	新規なチアゾール化合物及びその製造方法並びに該化合物を有効成分とする殺菌剤組成物
FR2590573A1 (fr)	1987-05-29	Composes heterocycliques, leur procede de production et leurs applications fongicides
JPS6026109B2 (ja)	1985-06-21	新規１−アシルオキシ−１−フエニル−２−アゾリル−エタンまたはその塩、その製造方法およびそれを活性成分として含有する殺菌剤若しくは殺線虫剤組成物
US6423730B1 (en)	2002-07-23	Method to control termites
IL34742A (en)	1973-01-30	Benzimidazole derivatives,their preparation and their use as fungicides
HU206022B (en)	1992-08-28	Fungicidal composition comprising imidazole derivative as active ingredient, process for producing the active ingredient and for applying the composition
JPS6333368A (ja)	1988-02-13	イミダゾ−ル誘導体