DD147612A5 - Mittel mit fungizider und nematizider wirkung - Google Patents

Mittel mit fungizider und nematizider wirkung Download PDF

Info

Publication number: DD147612A5
Authority: DD; German Democratic Republic
Prior art keywords: thiadiazole; carboxylic acid; thiadiazol; methylsulfonyl; ethylsulfonyl
Prior art date: 1978-12-07

Application number

DD79217423A

Other languages

German (de)

English (en)

Inventor

Ludwig Nuesslein

Dietrich Baumert

Ernst A Pieroh

Original Assignee

Schering Ag

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.)

1978-12-07

Filing date

1979-12-06

Publication date

1981-04-15

1979-12-06 Application filed by Schering Ag filed Critical Schering Ag

1981-04-15 Publication of DD147612A5 publication Critical patent/DD147612A5/de

Links

230000000694 effects Effects 0.000 title claims abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 96
-1 cyclohexylmethylaminocarbonyl Chemical group 0.000 claims abstract description 61
239000003795 chemical substances by application Substances 0.000 claims abstract description 22
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
230000000855 fungicidal effect Effects 0.000 claims abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 12
230000001069 nematicidal effect Effects 0.000 claims abstract description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 22
241000233866 Fungi Species 0.000 abstract description 10
239000000417 fungicide Substances 0.000 abstract description 6
239000005645 nematicide Substances 0.000 abstract description 6
241000244206 Nematoda Species 0.000 abstract description 5
239000000969 carrier Substances 0.000 abstract description 5
230000003032 phytopathogenic effect Effects 0.000 abstract description 4
238000003898 horticulture Methods 0.000 abstract description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract description 2
DERHNSJVDWFDKZ-UHFFFAOYSA-N 1,3,4-thiadiazole-2-carboxylic acid Chemical class OC(=O)C1=NN=CS1 DERHNSJVDWFDKZ-UHFFFAOYSA-N 0.000 abstract description 2
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 abstract description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
206010061217 Infestation Diseases 0.000 description 33
239000000243 solution Substances 0.000 description 30
239000013543 active substance Substances 0.000 description 28
239000002689 soil Substances 0.000 description 28
YIPJMDZMSVOAEN-UHFFFAOYSA-N 3h-thiadiazole-2-carboxylic acid Chemical compound OC(=O)N1NC=CS1 YIPJMDZMSVOAEN-UHFFFAOYSA-N 0.000 description 26
229910052757 nitrogen Inorganic materials 0.000 description 25
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 24
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 24
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 22
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 22
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MNBHOTWLXYVFRZ-UHFFFAOYSA-N 5-ethylsulfonyl-1,3,4-thiadiazole-2-carboxylic acid Chemical compound CCS(=O)(=O)C1=NN=C(C(O)=O)S1 MNBHOTWLXYVFRZ-UHFFFAOYSA-N 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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SMBLWULGZRYNDQ-UHFFFAOYSA-N 5-propan-2-ylsulfonyl-1,3,4-thiadiazole-2-carbonitrile Chemical compound CC(C)S(=O)(=O)C1=NN=C(C#N)S1 SMBLWULGZRYNDQ-UHFFFAOYSA-N 0.000 description 6
241000122692 Fusarium avenaceum Species 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000003857 carboxamides Chemical class 0.000 description 6
238000001816 cooling Methods 0.000 description 6
MMTYIHMWXABODP-UHFFFAOYSA-N n-methyl-5-methylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CNC(=O)C1=NN=C(S(C)(=O)=O)S1 MMTYIHMWXABODP-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
DJJCYOYLXJYHLY-UHFFFAOYSA-N 2-butylsulfinyl-1,3,4-thiadiazole Chemical compound C(CCC)S(=O)C1=NN=CS1 DJJCYOYLXJYHLY-UHFFFAOYSA-N 0.000 description 5
HYEZRRSICGHJRB-UHFFFAOYSA-N 2-butylsulfonyl-1,3,4-thiadiazole Chemical compound C(CCC)S(=O)(=O)C1=NN=CS1 HYEZRRSICGHJRB-UHFFFAOYSA-N 0.000 description 5
LFAKMZVLPIKVTJ-UHFFFAOYSA-N 2-ethylsulfonyl-1,3,4-thiadiazole Chemical compound CCS(=O)(=O)C1=NN=CS1 LFAKMZVLPIKVTJ-UHFFFAOYSA-N 0.000 description 5
QAAKTAOMRUFATF-UHFFFAOYSA-N 2-hexylsulfinyl-1,3,4-thiadiazole Chemical compound CCCCCCS(=O)C1=NN=CS1 QAAKTAOMRUFATF-UHFFFAOYSA-N 0.000 description 5
AEVQNXLAQTWNRC-UHFFFAOYSA-N 2-propan-2-ylsulfonyl-1,3,4-thiadiazole Chemical compound C(C)(C)S(=O)(=O)C1=NN=CS1 AEVQNXLAQTWNRC-UHFFFAOYSA-N 0.000 description 5
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239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
HBMLYMATMZAVBP-UHFFFAOYSA-N ethyl 2-sulfanylidene-3h-1,3,4-thiadiazole-5-carboxylate Chemical compound CCOC(=O)C1=NN=C(S)S1 HBMLYMATMZAVBP-UHFFFAOYSA-N 0.000 description 1
OJMFXKZCYFWXEQ-UHFFFAOYSA-N ethyl 5-ethylsulfanyl-1,3,4-thiadiazole-2-carboxylate Chemical compound CCOC(=O)C1=NN=C(SCC)S1 OJMFXKZCYFWXEQ-UHFFFAOYSA-N 0.000 description 1
SBVIHIUZFIVBKH-UHFFFAOYSA-N ethyl 5-ethylsulfonyl-1,3,4-thiadiazole-2-carboxylate Chemical compound CCOC(=O)C1=NN=C(S(=O)(=O)CC)S1 SBVIHIUZFIVBKH-UHFFFAOYSA-N 0.000 description 1
WOLABNPMNWDQHR-UHFFFAOYSA-N ethyl 5-prop-2-enylsulfanyl-1,3,4-thiadiazole-2-carboxylate Chemical compound CCOC(=O)C1=NN=C(SCC=C)S1 WOLABNPMNWDQHR-UHFFFAOYSA-N 0.000 description 1
KYSVKZDXOOLZRI-UHFFFAOYSA-N ethyl 5-propylsulfonyl-1,3,4-thiadiazole-2-carboxylate Chemical compound CCCS(=O)(=O)C1=NN=C(C(=O)OCC)S1 KYSVKZDXOOLZRI-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000002349 favourable effect Effects 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
235000015203 fruit juice Nutrition 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
235000019674 grape juice Nutrition 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
238000000034 method Methods 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
OWJAIXBAGAUFFZ-UHFFFAOYSA-N methyl 5-methylsulfonyl-1,3,4-thiadiazole-2-carboxylate Chemical compound COC(=O)C1=NN=C(S(C)(=O)=O)S1 OWJAIXBAGAUFFZ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 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
JAGPFHKKJBAMIT-UHFFFAOYSA-N n,n-dimethyl-5-methylsulfanyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CSC1=NN=C(C(=O)N(C)C)S1 JAGPFHKKJBAMIT-UHFFFAOYSA-N 0.000 description 1
QCTLFCKUOBINRD-UHFFFAOYSA-N n,n-dimethyl-5-propylsulfinyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCS(=O)C1=NN=C(C(=O)N(C)C)S1 QCTLFCKUOBINRD-UHFFFAOYSA-N 0.000 description 1
POSRVYLJVWTFQE-UHFFFAOYSA-N n-(2-methoxyethyl)-5-methylsulfinyl-1,3,4-thiadiazole-2-carboxamide Chemical compound COCCNC(=O)C1=NN=C(S(C)=O)S1 POSRVYLJVWTFQE-UHFFFAOYSA-N 0.000 description 1
SQOQCZMYVFCSLJ-UHFFFAOYSA-N n-(2-methylpropyl)-5-pentylsulfinyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCCCS(=O)C1=NN=C(C(=O)NCC(C)C)S1 SQOQCZMYVFCSLJ-UHFFFAOYSA-N 0.000 description 1
MMOBZMXKQJUZQX-UHFFFAOYSA-N n-(2-methylpropyl)-5-pentylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCCCS(=O)(=O)C1=NN=C(C(=O)NCC(C)C)S1 MMOBZMXKQJUZQX-UHFFFAOYSA-N 0.000 description 1
YXDNPQOBVKSJFN-UHFFFAOYSA-N n-(cyclohexylmethyl)-5-methylsulfanyl-1,3,4-thiadiazole-2-carboxamide Chemical compound S1C(SC)=NN=C1C(=O)NCC1CCCCC1 YXDNPQOBVKSJFN-UHFFFAOYSA-N 0.000 description 1
SALKGPHRLYNYBU-UHFFFAOYSA-N n-(cyclohexylmethyl)-5-methylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound S1C(S(=O)(=O)C)=NN=C1C(=O)NCC1CCCCC1 SALKGPHRLYNYBU-UHFFFAOYSA-N 0.000 description 1
VMWWKGRCBKRWOH-UHFFFAOYSA-N n-butyl-5-pentylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCCCS(=O)(=O)C1=NN=C(C(=O)NCCCC)S1 VMWWKGRCBKRWOH-UHFFFAOYSA-N 0.000 description 1
ZZADAJCQJBODMS-UHFFFAOYSA-N n-butyl-5-propylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCCNC(=O)C1=NN=C(S(=O)(=O)CCC)S1 ZZADAJCQJBODMS-UHFFFAOYSA-N 0.000 description 1
YHLUWFCJDBNPQM-UHFFFAOYSA-N n-cyclopropyl-5-pentylsulfinyl-1,3,4-thiadiazole-2-carboxamide Chemical compound S1C(S(=O)CCCCC)=NN=C1C(=O)NC1CC1 YHLUWFCJDBNPQM-UHFFFAOYSA-N 0.000 description 1
YRLGBCOHPWZFQR-UHFFFAOYSA-N n-cyclopropyl-5-pentylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound S1C(S(=O)(=O)CCCCC)=NN=C1C(=O)NC1CC1 YRLGBCOHPWZFQR-UHFFFAOYSA-N 0.000 description 1
DWJOXDKLMUUEJS-UHFFFAOYSA-N n-ethyl-5-methylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCNC(=O)C1=NN=C(S(C)(=O)=O)S1 DWJOXDKLMUUEJS-UHFFFAOYSA-N 0.000 description 1
RDNHGJGMFANMNE-UHFFFAOYSA-N n-ethyl-5-pentylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCCCS(=O)(=O)C1=NN=C(C(=O)NCC)S1 RDNHGJGMFANMNE-UHFFFAOYSA-N 0.000 description 1
NUYBFQFXRABULD-UHFFFAOYSA-N n-ethyl-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCNC(=O)C1=NN=C(SCC=C)S1 NUYBFQFXRABULD-UHFFFAOYSA-N 0.000 description 1
ARHGSBWHQSXKBR-UHFFFAOYSA-N n-ethyl-5-propylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCS(=O)(=O)C1=NN=C(C(=O)NCC)S1 ARHGSBWHQSXKBR-UHFFFAOYSA-N 0.000 description 1
CONOUJYBVLLMCB-UHFFFAOYSA-N n-methyl-5-propylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCS(=O)(=O)C1=NN=C(C(=O)NC)S1 CONOUJYBVLLMCB-UHFFFAOYSA-N 0.000 description 1
YUIYTWPXEKZDID-UHFFFAOYSA-N n-propan-2-yl-5-propylsulfinyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCS(=O)C1=NN=C(C(=O)NC(C)C)S1 YUIYTWPXEKZDID-UHFFFAOYSA-N 0.000 description 1
ITBODJYLXOZFGI-UHFFFAOYSA-N n-propan-2-yl-5-propylsulfonyl-1,3,4-thiadiazole-2-carboxamide Chemical compound CCCS(=O)(=O)C1=NN=C(C(=O)NC(C)C)S1 ITBODJYLXOZFGI-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000005554 pickling Methods 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DVLHGMFTRAFHPR-UHFFFAOYSA-N pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC=N1 DVLHGMFTRAFHPR-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
INWVNNCOIIHEPX-UHFFFAOYSA-N thiadiazole-4-carboxamide Chemical compound NC(=O)C1=CSN=N1 INWVNNCOIIHEPX-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052727 yttrium Inorganic materials 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- 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

Landscapes

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

DD79217423A 1978-12-07 1979-12-06 Mittel mit fungizider und nematizider wirkung DD147612A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782853196 DE2853196A1 (de)	1978-12-07	1978-12-07	1,3,4-thiadiazol-2-carbonsaeure-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide und nematizide mittel

Publications (1)

Publication Number	Publication Date
DD147612A5 true DD147612A5 (de)	1981-04-15

Family

ID=6056711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79217423A DD147612A5 (de)	1978-12-07	1979-12-06	Mittel mit fungizider und nematizider wirkung

Country Status (37)

Country	Link
US (2)	US4281121A (cs)
JP (1)	JPS5924980B2 (cs)
AR (1)	AR222510A1 (cs)
AT (1)	AT366233B (cs)
AU (1)	AU527930B2 (cs)
BE (1)	BE880477A (cs)
BG (1)	BG34607A3 (cs)
BR (1)	BR7907964A (cs)
CA (1)	CA1131223A (cs)
CH (1)	CH645108A5 (cs)
CS (1)	CS222290B2 (cs)
DD (1)	DD147612A5 (cs)
DE (1)	DE2853196A1 (cs)
DK (1)	DK521379A (cs)
EG (1)	EG14021A (cs)
ES (1)	ES486656A1 (cs)
FI (1)	FI793776A7 (cs)
FR (1)	FR2443464A1 (cs)
GB (1)	GB2037761B (cs)
HU (1)	HU186355B (cs)
IE (1)	IE49316B1 (cs)
IL (1)	IL58893A (cs)
IT (1)	IT1126495B (cs)
LU (1)	LU81958A1 (cs)
MA (1)	MA18667A1 (cs)
NL (1)	NL7908765A (cs)
NO (1)	NO150241C (cs)
NZ (1)	NZ192286A (cs)
PH (1)	PH20312A (cs)
PL (1)	PL119161B1 (cs)
PT (1)	PT70560A (cs)
RO (2)	RO78492A (cs)
SE (1)	SE435377B (cs)
SU (1)	SU886745A3 (cs)
TR (1)	TR20254A (cs)
YU (1)	YU296479A (cs)
ZA (1)	ZA796639B (cs)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4454147A (en) *	1982-05-27	1984-06-12	Fmc Corporation	Nematicidal 2-chloro-5-aryl-1,3,4-thiadiazoles
ES2058329T3 (es) *	1987-04-03	1994-11-01	Ciba Geigy Ag	2-mercapto-5-piridil-1,3,4-oxadiazoles y 1,3,4-tiadiazoles, procedimiento para su preparacion y su empleo como agentes nematicidas.
EP0290379A3 (de) *	1987-04-03	1989-02-22	Ciba-Geigy Ag	2-Mercapto-5-pyrazinyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel
DE3722320A1 (de) *	1987-07-07	1989-01-19	Bayer Ag	Mikrobizide mittel
US5591695A (en) *	1995-02-08	1997-01-07	American Cyanamid Co.	Herbicidal [1,3,4]oxadiazoles and thiadiazoles
JP2003026516A (ja) *	2001-07-11	2003-01-29	Mitsubishi Chemicals Corp	農園芸用殺菌剤
RU2447066C2 (ru) *	2010-04-15	2012-04-10	Александр Леонидович Гинцбург	Биологически активные вещества, подавляющие патогенные бактерии, и способ ингибирования секреции iii типа у патогенных бактерий

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4061645A (en) *	1969-12-08	1977-12-06	Schering Aktiengesellschaft	2-Trichloromethyl-5-methylsulfinyl-1,3,4-thiadiazole
US3903099A (en) *	1970-09-04	1975-09-02	Ciba Geigy Corp	Certain 2-halo-5-thio-1,3,4-thiadiazoles
DE2253863A1 (de) *	1972-11-03	1974-05-09	Basf Ag	Neue in 2- und 5-stellung substituierte 1,3,4-thiadiazole und verfahren zu ihrer herstellung
IL49200A0 (en) *	1975-03-27	1976-05-31	Pfizer	Novel heterocyclic thiols and their preparation

1978
- 1978-12-07 DE DE19782853196 patent/DE2853196A1/de not_active Withdrawn
1979
- 1979-11-30 NZ NZ192286A patent/NZ192286A/xx unknown
- 1979-12-03 FI FI793776A patent/FI793776A7/fi not_active Application Discontinuation
- 1979-12-04 SU SU792846651A patent/SU886745A3/ru active
- 1979-12-04 NL NL7908765A patent/NL7908765A/nl not_active Application Discontinuation
- 1979-12-05 CA CA341,276A patent/CA1131223A/en not_active Expired
- 1979-12-05 PL PL1979220157A patent/PL119161B1/pl unknown
- 1979-12-05 BG BG045807A patent/BG34607A3/xx unknown
- 1979-12-05 AT AT0770379A patent/AT366233B/de not_active IP Right Cessation
- 1979-12-05 LU LU81958A patent/LU81958A1/de unknown
- 1979-12-05 YU YU02964/79A patent/YU296479A/xx unknown
- 1979-12-05 EG EG723/79A patent/EG14021A/xx active
- 1979-12-06 SE SE7910061A patent/SE435377B/sv unknown
- 1979-12-06 BE BE0/198461A patent/BE880477A/fr not_active IP Right Cessation
- 1979-12-06 ES ES486656A patent/ES486656A1/es not_active Expired
- 1979-12-06 NO NO793974A patent/NO150241C/no unknown
- 1979-12-06 IL IL58893A patent/IL58893A/xx unknown
- 1979-12-06 US US06/101,061 patent/US4281121A/en not_active Expired - Lifetime
- 1979-12-06 AU AU53540/79A patent/AU527930B2/en not_active Ceased
- 1979-12-06 RO RO7999458A patent/RO78492A/ro unknown
- 1979-12-06 HU HU79SCHE705A patent/HU186355B/hu unknown
- 1979-12-06 DD DD79217423A patent/DD147612A5/de unknown
- 1979-12-06 TR TR20254A patent/TR20254A/xx unknown
- 1979-12-06 RO RO103233A patent/RO81506B/ro unknown
- 1979-12-06 BR BR7907964A patent/BR7907964A/pt unknown
- 1979-12-06 FR FR7929959A patent/FR2443464A1/fr active Granted
- 1979-12-07 IE IE2360/79A patent/IE49316B1/en unknown
- 1979-12-07 AR AR279192A patent/AR222510A1/es active
- 1979-12-07 GB GB7942344A patent/GB2037761B/en not_active Expired
- 1979-12-07 MA MA18869A patent/MA18667A1/fr unknown
- 1979-12-07 IT IT27903/79A patent/IT1126495B/it active
- 1979-12-07 CH CH1090379A patent/CH645108A5/de not_active IP Right Cessation
- 1979-12-07 PT PT70560A patent/PT70560A/pt unknown
- 1979-12-07 CS CS798550A patent/CS222290B2/cs unknown
- 1979-12-07 PH PH23388A patent/PH20312A/en unknown
- 1979-12-07 DK DK521379A patent/DK521379A/da not_active Application Discontinuation
- 1979-12-07 ZA ZA00796639A patent/ZA796639B/xx unknown
- 1979-12-07 JP JP54159033A patent/JPS5924980B2/ja not_active Expired
1980
- 1980-06-06 US US06/157,635 patent/US4279907A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK521379A (da)	1980-06-08
LU81958A1 (de)	1980-04-22
IL58893A0 (en)	1980-03-31
MA18667A1 (fr)	1980-07-01
FR2443464B1 (cs)	1983-08-26
CH645108A5 (de)	1984-09-14
ES486656A1 (es)	1980-10-01
IL58893A (en)	1984-02-29
NL7908765A (nl)	1980-06-10
PT70560A (de)	1980-01-01
SE7910061L (sv)	1980-06-08
GB2037761A (en)	1980-07-16
ATA770379A (de)	1981-08-15
PL220157A1 (cs)	1980-09-22
NZ192286A (en)	1981-07-13
IT1126495B (it)	1986-05-21
FR2443464A1 (fr)	1980-07-04
YU296479A (en)	1983-10-31
JPS55122773A (en)	1980-09-20
DE2853196A1 (de)	1980-06-26
HU186355B (en)	1985-07-29
ZA796639B (en)	1980-11-26
IE49316B1 (en)	1985-09-18
EG14021A (en)	1982-09-30
US4281121A (en)	1981-07-28
RO81506A (ro)	1983-04-29
IT7927903A0 (it)	1979-12-07
GB2037761B (en)	1983-04-13
PH20312A (en)	1986-11-25
SU886745A3 (ru)	1981-11-30
IE792360L (en)	1980-06-07
PL119161B1 (en)	1981-12-31
BR7907964A (pt)	1980-07-08
AU5354079A (en)	1980-06-12
US4279907A (en)	1981-07-21
JPS5924980B2 (ja)	1984-06-13
CA1131223A (en)	1982-09-07
NO793974L (no)	1980-06-10
BE880477A (fr)	1980-06-06
AR222510A1 (es)	1981-05-29
AT366233B (de)	1982-03-25
RO81506B (ro)	1983-04-30
RO78492A (ro)	1982-02-26
FI793776A7 (fi)	1981-01-01
BG34607A3 (bg)	1983-10-15
NO150241C (no)	1984-09-12
NO150241B (no)	1984-06-04
AU527930B2 (en)	1983-03-31
SE435377B (sv)	1984-09-24
CS222290B2 (en)	1983-06-24
TR20254A (tr)	1980-11-01

Publication	Publication Date	Title
EP0313512B1 (de)	1992-11-25	Benzothiadiazole und ihre Verwendung in Verfahren und Mitteln gegen Pflanzenkrankheiten
DE1695968C3 (de)	1979-04-12	4-Methylthiazolyl-5-carboxanilidverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als fungizide Mittel
EP0334809B1 (de)	1994-06-15	Mittel zum Schutz von Pflanzen gegen Krankheiten
DE2250077C2 (de)	1984-04-26	Pflanzenschutzmittel auf Basis eines s-Triazolo[3,4-b]benzoxazols oder s-Triazolo[3,4-b]benzthiazols und neue s-Triazolo[3,4-b]benzthiazole
EP0030676A1 (de)	1981-06-24	Phenoxybenzoesäure-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwuchsregulatoren
DD147612A5 (de)	1981-04-15	Mittel mit fungizider und nematizider wirkung
EP0387195B1 (de)	1994-07-27	Mittel zum Schutz von Pflanzen gegen Krankheiten
EP0420803B1 (de)	1994-03-09	Benzo-1,2,3-thiadiazol-Derivate und ihre Verwendung zum Schutz von Pflanzen gegen Krankheiten
GB2028319A (en)	1980-03-05	Biocidally active 1,2,3-triazole carboxylic acid amides a process for their manufacture and their use
EP0384889B1 (de)	1993-10-13	Mittel zum Schutz von Pflanzen gegen Krankheiten
EP0334812A2 (de)	1989-09-27	Mittel zum Schutz von Pflanzen gegen Krankheiten
EP0117482B1 (de)	1986-09-17	Substituierte Maleinsäureimide und deren Verwendung als Schädlingsbekämpfungsmittel
DE2310049A1 (de)	1973-09-13	Zusammensetzung und verfahren zur beeinflussung des wachstums von pflanzen
EP0502473B1 (de)	2000-04-26	Mikrobizide Benzo-1,2,3-thiadiazolderivate
DE2539396C3 (de)	1979-10-25	Pestizide
EP0780394A1 (de)	1997-06-25	Mikrobizide
JPH05194449A (ja)	1993-08-03	３−（４−ブロモフエニル）−５−メチルスルホニル−１，２，４−チアジアゾール
EP0040310A2 (de)	1981-11-25	Fungizide, heterocyclisch substituierte Thioglykolsäureanilide, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
KR830002816B1 (ko)	1983-12-26	1,3,4-티아디아졸-2-카복실산 유도체의 제조방법
DD145989A5 (de)	1981-01-21	Fungizides mittel
DD265315A5 (de)	1989-03-01	Fungizide und/oder bakterizide zusammensetzung
DD152468A5 (de)	1981-12-02	Fungizides mittel
DE3703213A1 (de)	1988-08-11	2-imino-1,3-dithietane, ihre herstellung und verwendung als schaedlingsbekaempfungsmittel
JPH04178362A (ja)	1992-06-25	尿素誘導体およびそれを含有する有害生物防除剤
DE2921141A1 (de)	1980-12-11	2-(1,3,4-thiadiazol-2-yl)-1,2,4oxadiazolidin-3,5-dione, verfahren zu ihrer herstellung und ihre verwendung als pflanzenbakterizide