DE2434922A1 - Isothiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide - Google Patents
Isothiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizideInfo
- Publication number
- DE2434922A1 DE2434922A1 DE2434922A DE2434922A DE2434922A1 DE 2434922 A1 DE2434922 A1 DE 2434922A1 DE 2434922 A DE2434922 A DE 2434922A DE 2434922 A DE2434922 A DE 2434922A DE 2434922 A1 DE2434922 A1 DE 2434922A1
- Authority
- DE
- Germany
- Prior art keywords
- isothiazolyl
- cyano
- carbamoyl
- methyl
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 ISOTHIAZOLYL Chemical class 0.000 title claims description 50
- 239000004009 herbicide Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- FMIRBTBZSHSEOT-UHFFFAOYSA-N CC(C)(C)C1=NSC(NC(N(C)C)=O)=C1C#N Chemical compound CC(C)(C)C1=NSC(NC(N(C)C)=O)=C1C#N FMIRBTBZSHSEOT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 210000002700 urine Anatomy 0.000 claims 2
- RYMMXRRHLLHGHL-UHFFFAOYSA-N 1-(4-cyano-3-methyl-1,2-thiazol-5-yl)-3-methylurea Chemical compound CNC(=O)Nc1snc(C)c1C#N RYMMXRRHLLHGHL-UHFFFAOYSA-N 0.000 claims 1
- ZHYAQFYUMZNLAH-UHFFFAOYSA-N 3-(4-cyano-3-methyl-1,2-thiazol-5-yl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC=1SN=C(C)C=1C#N ZHYAQFYUMZNLAH-UHFFFAOYSA-N 0.000 claims 1
- WFMZEPCUHOISAQ-UHFFFAOYSA-N NC(NC1=NSC=C1C#N)=O Chemical compound NC(NC1=NSC=C1C#N)=O WFMZEPCUHOISAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- TXVNVGVZRRHVBG-UHFFFAOYSA-N phenyl N-(1,2-thiazol-3-yl)carbamate Chemical compound O=C(Nc1ccsn1)Oc1ccccc1 TXVNVGVZRRHVBG-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
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- 239000004480 active ingredient Substances 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000000155 melt Substances 0.000 description 5
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
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- 239000012047 saturated solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
- 235000003228 Lactuca sativa Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
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- 239000003995 emulsifying agent Substances 0.000 description 3
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- GMOKXEFUQJHUOP-UHFFFAOYSA-N 3-amino-2-cyano-4-methylpent-2-enethioamide Chemical compound CC(C)C(N)=C(C#N)C(N)=S GMOKXEFUQJHUOP-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- 239000003337 fertilizer Substances 0.000 description 2
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- 230000002363 herbicidal effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
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- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000100170 Phaseolus lunatus Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960000892 attapulgite Drugs 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
- 239000006227 byproduct Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-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
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- QBPGOTKMBASIAG-UHFFFAOYSA-N phenyl n-(4-cyano-3-methyl-1,2-thiazol-5-yl)carbamate Chemical compound CC1=NSC(NC(=O)OC=2C=CC=CC=2)=C1C#N QBPGOTKMBASIAG-UHFFFAOYSA-N 0.000 description 1
- DJXGJYCSPXRZAK-UHFFFAOYSA-N phenyl n-(sulfanylidenemethylidene)carbamate Chemical compound S=C=NC(=O)OC1=CC=CC=C1 DJXGJYCSPXRZAK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38089373A | 1973-07-19 | 1973-07-19 | |
| US47777874A | 1974-06-10 | 1974-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2434922A1 true DE2434922A1 (de) | 1975-01-30 |
Family
ID=27009154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2434922A Pending DE2434922A1 (de) | 1973-07-19 | 1974-07-19 | Isothiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Country Status (15)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0327981A1 (de) * | 1988-02-12 | 1989-08-16 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-Cyano-3-aminoacrylnitril-Derivaten |
| US5538939A (en) * | 1993-08-24 | 1996-07-23 | Basf Aktiengesellschaft | Acylamino-substituted isoxazole or isothiazole derivatives, their preparation and their use |
| WO2001040223A3 (en) * | 1999-12-02 | 2001-12-20 | Novartis Ag | Aminoheterocyclylamides as pesticides and antiparasitic agents |
| WO2010086118A1 (de) | 2009-02-02 | 2010-08-05 | Bayer Cropscience Ag | Isothiazolyloxyphenylamidine und deren verwendung als fungizide |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58153668U (ja) * | 1982-04-09 | 1983-10-14 | 上田 春野 | 開き戸止め具 |
| JPH0248357U (enrdf_load_stackoverflow) * | 1988-09-29 | 1990-04-04 |
-
1974
- 1974-07-09 AU AU71039/74A patent/AU7103974A/en not_active Expired
- 1974-07-09 IN IN1535/CAL/74A patent/IN140035B/en unknown
- 1974-07-10 IL IL45230A patent/IL45230A0/xx unknown
- 1974-07-16 AT AT588374A patent/AT336944B/de not_active IP Right Cessation
- 1974-07-17 LU LU70547A patent/LU70547A1/xx unknown
- 1974-07-17 FR FR7424919A patent/FR2237893A1/fr not_active Withdrawn
- 1974-07-18 BR BR5962/74A patent/BR7405962D0/pt unknown
- 1974-07-18 DK DK387374A patent/DK387374A/da unknown
- 1974-07-18 NL NL7409735A patent/NL7409735A/xx unknown
- 1974-07-18 IT IT25332/74A patent/IT1048182B/it active
- 1974-07-19 PH PH16064A patent/PH10517A/en unknown
- 1974-07-19 DE DE2434922A patent/DE2434922A1/de active Pending
- 1974-07-19 ES ES428446A patent/ES428446A1/es not_active Expired
- 1974-07-19 JP JP49082337A patent/JPS5031043A/ja active Pending
- 1974-07-20 EG EG290/74A patent/EG11086A/xx active
-
1975
- 1975-05-31 ES ES448389A patent/ES448389A1/es not_active Expired
- 1975-05-31 ES ES448390A patent/ES448390A1/es not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0327981A1 (de) * | 1988-02-12 | 1989-08-16 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 2-Cyano-3-aminoacrylnitril-Derivaten |
| US5047570A (en) * | 1988-02-12 | 1991-09-10 | Basf Aktiengesellschaft | Preparation of 2-cyano-3-aminoacrylonitrile derivatives |
| US5538939A (en) * | 1993-08-24 | 1996-07-23 | Basf Aktiengesellschaft | Acylamino-substituted isoxazole or isothiazole derivatives, their preparation and their use |
| WO2001040223A3 (en) * | 1999-12-02 | 2001-12-20 | Novartis Ag | Aminoheterocyclylamides as pesticides and antiparasitic agents |
| AU765618B2 (en) * | 1999-12-02 | 2003-09-25 | Novartis Ag | Aminoheterocyclylamides as pesticides and antiparasitic agents |
| US6673820B2 (en) | 1999-12-02 | 2004-01-06 | Novartis Animal Health Us, Inc. | Aminoheterocyclylamides as pesticides and antiparasitic agents |
| WO2010086118A1 (de) | 2009-02-02 | 2010-08-05 | Bayer Cropscience Ag | Isothiazolyloxyphenylamidine und deren verwendung als fungizide |
| EP2223917A1 (de) | 2009-02-02 | 2010-09-01 | Bayer CropScience AG | Isothiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| US8138211B2 (en) | 2009-02-02 | 2012-03-20 | Bayer Cropscience Ag | Isothiazolyloxyphenylamidines and their use as fungicides |
| US8470739B2 (en) | 2009-02-02 | 2013-06-25 | Bayer Cropsciene Ag | Isothiazolyloxyphenylamidines and their use as fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5031043A (enrdf_load_stackoverflow) | 1975-03-27 |
| AT336944B (de) | 1977-06-10 |
| FR2237893A1 (en) | 1975-02-14 |
| IN140035B (enrdf_load_stackoverflow) | 1976-09-04 |
| EG11086A (en) | 1976-11-30 |
| AU7103974A (en) | 1976-01-15 |
| ES448390A1 (es) | 1977-08-01 |
| NL7409735A (nl) | 1975-01-21 |
| LU70547A1 (enrdf_load_stackoverflow) | 1975-03-27 |
| ES428446A1 (es) | 1976-12-16 |
| ES448389A1 (es) | 1977-08-01 |
| BR7405962D0 (pt) | 1975-05-06 |
| DK387374A (enrdf_load_stackoverflow) | 1975-03-10 |
| ATA588374A (de) | 1976-09-15 |
| PH10517A (en) | 1977-05-26 |
| IT1048182B (it) | 1980-11-20 |
| IL45230A0 (en) | 1974-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |