IL91000A - תולדות 4-הלוגנו-5-ניטרותיאזול, הכנתן והשימוש בהן כקוטלי פיטריות וחיידקים - Google Patents

תולדות 4-הלוגנו-5-ניטרותיאזול, הכנתן והשימוש בהן כקוטלי פיטריות וחיידקים

Info

Publication number: IL91000A
Authority: IL; Israel
Prior art keywords: carbon atoms; alkyl; formula; phenyl; optionally substituted
Prior art date: 1988-07-20

Application number

IL9100089A

Other languages

English (en)

Other versions

IL91000A0 (en

Original Assignee

Bayer 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.)

1988-07-20

Filing date

1989-07-17

Publication date

1994-05-30

1989-07-17 Application filed by Bayer Ag filed Critical Bayer Ag

1990-02-09 Publication of IL91000A0 publication Critical patent/IL91000A0/xx

1994-05-30 Publication of IL91000A publication Critical patent/IL91000A/he

Links

238000002360 preparation method Methods 0.000 title claims description 16
239000000417 fungicide Substances 0.000 title description 6
230000003641 microbiacidal effect Effects 0.000 title description 6
229940124561 microbicide Drugs 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 151
-1 alkyl radical Chemical class 0.000 claims description 107
125000000217 alkyl group Chemical group 0.000 claims description 67
125000001424 substituent group Chemical group 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 32
238000000034 method Methods 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 16
239000012038 nucleophile Substances 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 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 14
241000233866 Fungi Species 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 11
239000007800 oxidant agent Substances 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000004442 acylamino group Chemical group 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000006193 alkinyl group Chemical group 0.000 claims description 8
125000003884 phenylalkyl group Chemical group 0.000 claims description 8
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
239000004606 Fillers/Extenders Substances 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
241000607479 Yersinia pestis Species 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 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
239000004094 surface-active agent Substances 0.000 claims description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
150000003568 thioethers Chemical class 0.000 claims description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
150000003851 azoles Chemical class 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 101
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 39
239000002904 solvent Substances 0.000 description 37
239000000243 solution Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
241000196324 Embryophyta Species 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
239000003208 petroleum Substances 0.000 description 17
239000000126 substance Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229910052740 iodine Inorganic materials 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000005457 ice water Substances 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
239000012770 industrial material Substances 0.000 description 10
235000015097 nutrients Nutrition 0.000 description 10
239000000047 product Substances 0.000 description 10
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
230000001681 protective effect Effects 0.000 description 8
241000894007 species Species 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000011230 binding agent Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004104 aryloxy group Chemical group 0.000 description 6
238000009472 formulation Methods 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
239000007788 liquid Substances 0.000 description 6
UNWUPQUTAGSGOA-UHFFFAOYSA-N 2,4-dichloro-5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C=1SC(Cl)=NC=1Cl UNWUPQUTAGSGOA-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
239000011630 iodine Substances 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000005507 spraying Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
241000195493 Cryptophyta Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000002102 aryl alkyloxo group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
244000005700 microbiome Species 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
241000222418 Lentinus Species 0.000 description 3
241000736122 Parastagonospora nodorum Species 0.000 description 3
241000233622 Phytophthora infestans Species 0.000 description 3
241000589516 Pseudomonas Species 0.000 description 3
241000228453 Pyrenophora Species 0.000 description 3
241000228452 Venturia inaequalis Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
239000008272 agar Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000004183 alkoxy alkyl group Chemical group 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
229910001512 metal fluoride Inorganic materials 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000002689 soil Substances 0.000 description 3
125000001174 sulfone group Chemical group 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
239000002023 wood Substances 0.000 description 3
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
241000223600 Alternaria Species 0.000 description 2
241000223602 Alternaria alternata Species 0.000 description 2
241000228245 Aspergillus niger Species 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241001515917 Chaetomium globosum Species 0.000 description 2
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588722 Escherichia Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
241001330975 Magnaporthe oryzae Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
241000233614 Phytophthora Species 0.000 description 2
241000233626 Plasmopara Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
241000896242 Podosphaera Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241000520648 Pyrenophora teres Species 0.000 description 2
206010039509 Scab Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
240000003768 Solanum lycopersicum Species 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
241000907561 Sydowia polyspora Species 0.000 description 2
241000221576 Uromyces Species 0.000 description 2
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229940039407 aniline Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000005068 cooling lubricant Substances 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000003292 glue Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
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 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010985 leather Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000000123 paper Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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150000002825 nitriles Chemical class 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229920001059 synthetic polymer Polymers 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
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
239000004753 textile 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
229960004546 thiabendazole Drugs 0.000 description 1
150000007979 thiazole derivatives Chemical class 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
229960002447 thiram Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/58—Nitro radicals
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

IL9100089A 1988-07-20 1989-07-17 תולדות 4-הלוגנו-5-ניטרותיאזול, הכנתן והשימוש בהן כקוטלי פיטריות וחיידקים IL91000A (he)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3824520		1988-07-20
DE3842970A DE3842970A1 (de)	1988-07-20	1988-12-21	4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung als schaedlingsbekaempfungsmittel und neue zwischenprodukte

Publications (2)

Publication Number	Publication Date
IL91000A0 IL91000A0 (en)	1990-02-09
IL91000A true IL91000A (he)	1994-05-30

Family

ID=25870267

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9100089A IL91000A (he)	1988-07-20	1989-07-17	תולדות 4-הלוגנו-5-ניטרותיאזול, הכנתן והשימוש בהן כקוטלי פיטריות וחיידקים

Country Status (10)

Country	Link
US (2)	US4962102A (he)
EP (1)	EP0351662A3 (he)
JP (1)	JPH0278672A (he)
KR (1)	KR910002820A (he)
BR (1)	BR8903574A (he)
DE (1)	DE3842970A1 (he)
DK (1)	DK358389A (he)
HU (1)	HU206249B (he)
IL (1)	IL91000A (he)
PT (1)	PT91112B (he)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3807232A1 (de) *	1988-03-05	1989-09-14	Bayer Ag	Substituierte acrylsaeureester
DE3842970A1 (de) *	1988-07-20	1990-01-25	Bayer Ag, 51373 Leverkusen	4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung als schaedlingsbekaempfungsmittel und neue zwischenprodukte
DE3919365A1 (de) *	1989-06-14	1990-12-20	Bayer Ag	2-acylamino-4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung in schaedlingsbekaempfungsmitteln und neue zwischenprodukte
NZ240313A (en) *	1990-10-22	1994-04-27	Res Corp Technologies Inc	Anti-retrovirus compositions containing aryl and heteroaryl derivatives
IL112721A0 (en) *	1994-03-10	1995-05-26	Zeneca Ltd	Azole derivatives
DE19545635A1 (de) *	1995-12-07	1997-06-12	Bayer Ag	Dithiazoldioxide
DE19721627A1 (de) *	1997-05-23	1998-11-26	Bayer Ag	S-Pyridyl-dithiazoldioxide
EP3968772A4 (en) *	2019-05-13	2023-05-24	Agrematch Ltd.	COMPOSITIONS FOR CROP PROTECTION

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2168182A1 (en) *	1972-01-19	1973-08-31	Aries Robert	Substd-thiazole (thio-or dithio) phosphates - as biodegradable insecticides with antifungal and bacteriostatic activity
DE2627328A1 (de) *	1976-06-18	1977-12-29	Hoechst Ag	2-alkylsulfinyl-5-nitro-thiazole, ihre herstellung und verwendung als fungizide und bakterizide
JPS6168479A (ja) *	1984-09-12	1986-04-08	Mitsui Toatsu Chem Inc	チアゾ−ル系化合物及びその製造方法
DE3518520A1 (de) *	1985-05-23	1986-11-27	Bayer Ag, 5090 Leverkusen	2,4-dichlor-5-nitro-thiazol
DE3842970A1 (de) *	1988-07-20	1990-01-25	Bayer Ag, 51373 Leverkusen	4-halogen-5-nitrothiazol-derivate, verfahren zu ihrer herstellung, ihre verwendung als schaedlingsbekaempfungsmittel und neue zwischenprodukte

1988
- 1988-12-21 DE DE3842970A patent/DE3842970A1/de not_active Withdrawn
1989
- 1989-07-07 EP EP89112403A patent/EP0351662A3/de not_active Withdrawn
- 1989-07-10 PT PT91112A patent/PT91112B/pt not_active IP Right Cessation
- 1989-07-12 US US07/378,894 patent/US4962102A/en not_active Expired - Fee Related
- 1989-07-17 IL IL9100089A patent/IL91000A/he not_active IP Right Cessation
- 1989-07-19 BR BR898903574A patent/BR8903574A/pt not_active Application Discontinuation
- 1989-07-19 HU HU893672A patent/HU206249B/hu not_active IP Right Cessation
- 1989-07-19 DK DK358389A patent/DK358389A/da not_active Application Discontinuation
- 1989-07-20 JP JP1186189A patent/JPH0278672A/ja active Pending
- 1989-07-20 KR KR1019890010263A patent/KR910002820A/ko not_active Ceased
1990
- 1990-04-24 US US07/513,745 patent/US5075326A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK358389D0 (da)	1989-07-19
HUT50591A (en)	1990-03-28
JPH0278672A (ja)	1990-03-19
PT91112A (pt)	1990-02-08
US4962102A (en)	1990-10-09
IL91000A0 (en)	1990-02-09
EP0351662A2 (de)	1990-01-24
KR910002820A (ko)	1991-02-26
HU206249B (en)	1992-10-28
EP0351662A3 (de)	1990-06-27
BR8903574A (pt)	1990-10-02
US5075326A (en)	1991-12-24
PT91112B (pt)	1995-05-04
DK358389A (da)	1990-01-21
DE3842970A1 (de)	1990-01-25

Publication	Publication Date	Title
US4785002A (en)	1988-11-15	Imidazo-pyrrolo-pyridines useful as fungicidal and growth-regulating agents
US4663327A (en)	1987-05-05	1-heteroaryl-4-aryl-pyrazolin-5-ones
US4927824A (en)	1990-05-22	Fungicidal trisubstituted 1,3,5-triazine-2,4,6-triones
EP0384211B1 (de)	1994-09-07	Substituierte Acrylsäureester
US5071865A (en)	1991-12-10	Pesticidal 2-acylamino-4-halogeno-5-nitrothiazoles
IL91000A (he)	1994-05-30	תולדות 4-הלוגנו-5-ניטרותיאזול, הכנתן והשימוש בהן כקוטלי פיטריות וחיידקים
US4894381A (en)	1990-01-16	Microbicidal (azolyl-vinyl)-phenol alkenyl ethers
US4737515A (en)	1988-04-12	Use of tetrahydrobenzothienylurea derivatives as fungicides
US4804673A (en)	1989-02-14	Fungicidal sulfonyl azoles
KR100297332B1 (ko)	2001-10-24	해충구제제로서의피리딜-1,2,4-티아디아졸
US4752607A (en)	1988-06-21	Alkoxycarbonyl-substituted hydroxythiophene-carboxamides, fungicidal compositions and use
US4871864A (en)	1989-10-03	Carbamoyloxythiophene fungicides
US4716176A (en)	1987-12-29	Benzaldoxime carbamate derivatives, their compositions and method of use
US4886832A (en)	1989-12-12	Fungicidal benzaldoxime derivatives
US4743615A (en)	1988-05-10	Substituted pyrazolin-5-ones, composition containing, and method of using them to combat fungi
US4610985A (en)	1986-09-09	Allophanate derivative, fungicidal compositions and use
CA1263863A (en)	1989-12-12	2,4-dichloro-5-nitro-thiazole
DE3419127A1 (de)	1985-11-28	1-heteroaryl-4-aryl-pyrazolin-5-one
US4729998A (en)	1988-03-08	Cyclic carbamates and fungicidal use
US5093345A (en)	1992-03-03	Pesticidal nitro-substituted benzothiazolones
US4824844A (en)	1989-04-25	Saccharine salts of substituted amines, fungicidal compositions and use
EP0189800A2 (de)	1986-08-06	Thiocyanatomethylthio-Gruppen enthaltende Verbindungen
US4910221A (en)	1990-03-20	Pesticidal alpha-methylsulphonyl-benzaldoxime derivatives
US4692461A (en)	1987-09-08	Fungicidal thienylurea derivatives
DE3933933A1 (de)	1991-04-18	Trisubstituierte 1,3,5-triazin-2,4,6-trione

Legal Events

Date	Code	Title	Description
1996-05-14	RH	Patent void