CH654835A5 - 1,2,4-thiadiazol-derivate und diese verbindungen enthaltendes fungizides mittel. - Google Patents

1,2,4-thiadiazol-derivate und diese verbindungen enthaltendes fungizides mittel. Download PDF

Info

Publication number: CH654835A5
Authority: CH; Switzerland
Prior art keywords: group; carbon atoms; halogen; phenyl; alkyl
Prior art date: 1982-06-24

Application number

CH3474/83A

Other languages

German (de)

English (en)

Inventor

Kenji Hagiwara

Keiichi Ishimitsu

Shou Hashimoto

Susumu Shimoda

Original Assignee

Nippon Soda Co

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.)

1982-06-24

Filing date

1983-06-24

Publication date

1986-03-14

1983-06-24 Application filed by Nippon Soda Co filed Critical Nippon Soda Co

1986-03-14 Publication of CH654835A5 publication Critical patent/CH654835A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 50
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 title claims description 7
239000000417 fungicide Substances 0.000 title description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
-1 N-methylanilino group Chemical group 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 18
230000000855 fungicidal effect Effects 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000005108 alkenylthio group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000004438 haloalkoxy group Chemical group 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000004660 phenylalkylthio group Chemical group 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 69
229910000042 hydrogen bromide Inorganic materials 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
238000000354 decomposition reaction Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
241000196324 Embryophyta Species 0.000 description 11
239000013078 crystal Substances 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
239000004563 wettable powder Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
240000008067 Cucumis sativus Species 0.000 description 6
239000000843 powder Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000428 dust Substances 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000220225 Malus Species 0.000 description 4
241000233679 Peronosporaceae Species 0.000 description 4
231100000674 Phytotoxicity Toxicity 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000335053 Beta vulgaris Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000918585 Pythium aphanidermatum Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000003449 preventive effect Effects 0.000 description 3
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 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
239000005745 Captan Substances 0.000 description 2
235000009849 Cucumis sativus Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
206010039509 Scab Diseases 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 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
235000021016 apples Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229940117949 captan Drugs 0.000 description 2
239000013043 chemical agent Substances 0.000 description 2
239000013065 commercial product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 2
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000003898 horticulture Methods 0.000 description 2
KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
WXBHKHTWAPLUSQ-UHFFFAOYSA-N (2-methyl-5-prop-2-ynylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=C(C)OC(CC#C)=C1 WXBHKHTWAPLUSQ-UHFFFAOYSA-N 0.000 description 1
CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-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
FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
JWPMHRXIIOEZRU-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole Chemical compound C1NC=NS1 JWPMHRXIIOEZRU-UHFFFAOYSA-N 0.000 description 1
YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
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URYAFVKLYSEINW-UHFFFAOYSA-N Chlorfenethol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1=CC=C(Cl)C=C1 URYAFVKLYSEINW-UHFFFAOYSA-N 0.000 description 1
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OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000010721 machine oil Substances 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
KFVKPSOJAAJVSR-UHFFFAOYSA-N n-methylbenzenecarboximidoyl chloride Chemical compound CN=C(Cl)C1=CC=CC=C1 KFVKPSOJAAJVSR-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical compound CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 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
239000003208 petroleum Substances 0.000 description 1
LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000011505 plaster 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
WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
229940108410 resmethrin Drugs 0.000 description 1
VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
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 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-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
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CH3474/83A 1982-06-24 1983-06-24 1,2,4-thiadiazol-derivate und diese verbindungen enthaltendes fungizides mittel. CH654835A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57108884A JPS58225077A (ja)	1982-06-24	1982-06-24	１，２，４−チアジアゾ−ル誘導体及び農園芸用殺菌剤

Publications (1)

Publication Number	Publication Date
CH654835A5 true CH654835A5 (de)	1986-03-14

Family

ID=14496031

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3474/83A CH654835A5 (de)	1982-06-24	1983-06-24	1,2,4-thiadiazol-derivate und diese verbindungen enthaltendes fungizides mittel.

Country Status (12)

Country	Link
JP (1)	JPS58225077A (fr)
KR (1)	KR840005119A (fr)
BE (1)	BE897119A (fr)
CH (1)	CH654835A5 (fr)
DE (1)	DE3322662A1 (fr)
ES (1)	ES8500922A1 (fr)
FR (1)	FR2529204A1 (fr)
GB (1)	GB2124212B (fr)
HU (1)	HU193169B (fr)
IL (1)	IL69021A (fr)
IT (1)	IT1174762B (fr)
NL (1)	NL8302260A (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3260725A (en) *	1961-03-15	1966-07-12	Olin Mathieson	3-trichloromethyl-5-substituted-1, 2, 4-thiadiazole
US3324141A (en) *	1965-08-12	1967-06-06	Olin Mathieson	3-trichloromethyl-5-amino-1, 2, 4-thiadiazoles
US3574226A (en) *	1967-05-19	1971-04-06	Ansul Co	Substituted delta**2-1,2,4-thiadiazolin-5-ones
DE1907116A1 (de) *	1969-02-13	1970-09-03	Bayer Ag	5-Chlor-3-oxo-1,2,4-thiadiazoline
DE1925995A1 (de) *	1969-05-21	1970-11-26	Bayer Ag	2-Alkyloxymethyl-3-chlor-1,2,4-thiaimidazol-5-one
US3764685A (en) *	1970-09-08	1973-10-09	Velsicol Chemical Corp	Certain thiadiazoles as fungicides
US3884929A (en) *	1970-12-14	1975-05-20	Eric Smith	Selected 3-trichloromethyl-5-substituted 1,2,4-thiadiazoles
BE788149A (fr) *	1971-08-31	1973-02-28	Ciba Geigy	Application de derives du thiadiazole a la conservation de nourritures pour animaux

1982
- 1982-06-24 JP JP57108884A patent/JPS58225077A/ja active Granted
1983
- 1983-06-17 IL IL69021A patent/IL69021A/xx unknown
- 1983-06-23 HU HU832231A patent/HU193169B/hu unknown
- 1983-06-23 DE DE19833322662 patent/DE3322662A1/de not_active Withdrawn
- 1983-06-23 IT IT48572/83A patent/IT1174762B/it active
- 1983-06-23 KR KR1019830002824A patent/KR840005119A/ko not_active Abandoned
- 1983-06-23 GB GB08317065A patent/GB2124212B/en not_active Expired
- 1983-06-23 ES ES523567A patent/ES8500922A1/es not_active Expired
- 1983-06-23 BE BE0/211056A patent/BE897119A/fr not_active IP Right Cessation
- 1983-06-23 FR FR8310414A patent/FR2529204A1/fr active Granted
- 1983-06-24 CH CH3474/83A patent/CH654835A5/de not_active IP Right Cessation
- 1983-06-24 NL NL8302260A patent/NL8302260A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
ES523567A0 (es)	1984-11-01
NL8302260A (nl)	1984-01-16
IT8348572A0 (it)	1983-06-23
JPS58225077A (ja)	1983-12-27
FR2529204A1 (fr)	1983-12-30
GB2124212B (en)	1985-10-09
GB8317065D0 (en)	1983-07-27
IL69021A (en)	1986-09-30
HU193169B (en)	1987-08-28
GB2124212A (en)	1984-02-15
BE897119A (fr)	1983-10-17
DE3322662A1 (de)	1983-12-29
IL69021A0 (en)	1983-10-31
FR2529204B1 (fr)	1985-05-17
KR840005119A (ko)	1984-11-03
JPH038347B2 (fr)	1991-02-05
ES8500922A1 (es)	1984-11-01
IT1174762B (it)	1987-07-01

Legal Events

Date	Code	Title	Description
1988-02-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0012158B1 (fr)	1984-08-15	Dérivés d'oxime et leur utilisation dans la protection des cultures de plantes
EP0011047A2 (fr)	1980-05-14	Dérivés d'oxime pour la protection de plantes cultivées
EP0010143B1 (fr)	1983-09-28	Dérivés d'oxime pour la protection de plantes cultivées
EP0010588B1 (fr)	1985-03-13	Composés d'oxime contenant du soufre et leur utilisation pour la protection des plantes cultivées
DD155384A5 (de)	1982-06-09	Fungizide und/oder bakterizide zusammensetzungen
CH637268A5 (de)	1983-07-29	Mittel zum schutz von pflanzenkulturen.
DE2801868C2 (de)	1986-09-25	Benzthiazolon- und Benzoxazolon-Derivate
EP0010058B1 (fr)	1983-06-22	Procédé et compositions pour la protection de cultures de plantes contre l'action phytotoxique des herbicides forts; dérivés d'oxime-éthers
DE2737298C2 (de)	1986-10-30	Verwendung von 4(1H)-Oxo-3-chinolincarbonsäure-Derivaten bei der Bekämpfung pflanzenpathogener Bakterien
CH644854A5 (de)	1984-08-31	Salze von thiazolyliden-oxo-propionitrilen, insektizides mittel, enthaltend diese salze sowie verfahren zu ihrer herstellung.
DE2123277A1 (de)	1971-12-02	Insektizide Mittel
EP0334812B1 (fr)	1994-04-06	Agents pour la protection de plants contre des maladies
DE3872634T2 (de)	1992-12-03	Thiadiazine, verfahren zu deren herstellung und insektizide.
CH654835A5 (de)	1986-03-14	1,2,4-thiadiazol-derivate und diese verbindungen enthaltendes fungizides mittel.
DE2902861A1 (de)	1979-08-02	Mikrobizide mittel
DE2557406A1 (de)	1976-07-08	Neue thioharnstoffverbindungen, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2833767C2 (fr)	1988-07-21
CH630614A5 (de)	1982-06-30	Verfahren zur herstellung von neuen 1-cycloalkylcarbonyl-3-(3,5-dihalogenphenyl)-imidazolidin-2,4-dionen.
DE3518520C2 (fr)	1992-11-05
DE2916611C2 (fr)	1988-03-24
EP0274988A2 (fr)	1988-07-20	Dihydrothiadiazoles
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
DE2132392A1 (de)	1973-01-11	2-mercapto-1,3-thiazol-5-carbonsaeureanilide, verfahren zu ihrer herstellung und ihre fungizide verwendung
DE2234466A1 (de)	1973-01-25	Thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide
DE2453210A1 (de)	1976-05-13	Fungizides mittel