DD229582A5 - Schaedlingsbekaempfungsmittel - Google Patents

Schaedlingsbekaempfungsmittel Download PDF

Info

Publication number: DD229582A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; dione; alkyl; thiolane; carbon atoms
Prior art date: 1983-12-09

Application number

DD84270458A

Other languages

German (de)

English (en)

Inventor

Herbert Gayer

Wilhelm Brandes

Gerd Haenssler

Paul Reinecke

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.)

1983-12-09

Filing date

1984-12-07

Publication date

1985-11-13

1984-12-07 Application filed by Bayer Ag filed Critical Bayer Ag

1985-11-13 Publication of DD229582A5 publication Critical patent/DD229582A5/de

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
PQCRAXZTPPJSCG-UHFFFAOYSA-N 2,4-dioxothiolane-3-carboxamide Chemical class NC(=O)C1C(=O)CSC1=O PQCRAXZTPPJSCG-UHFFFAOYSA-N 0.000 claims abstract description 9
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 17
238000000034 method Methods 0.000 claims description 10
239000000575 pesticide Substances 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 3
239000002855 microbicide agent Substances 0.000 claims description 2
241000607479 Yersinia pestis Species 0.000 claims 3
241000894006 Bacteria Species 0.000 claims 1
241000233866 Fungi Species 0.000 claims 1
230000000855 fungicidal effect Effects 0.000 abstract description 5
239000000460 chlorine Substances 0.000 description 38
150000001875 compounds Chemical class 0.000 description 35
125000004432 carbon atom Chemical group C* 0.000 description 20
241000196324 Embryophyta Species 0.000 description 19
239000002904 solvent Substances 0.000 description 18
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
-1 alkylene radical Chemical class 0.000 description 15
239000000203 mixture Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000003995 emulsifying agent Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 8
230000001681 protective effect Effects 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
238000005507 spraying Methods 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
JWZBKWNQNYDBBU-UHFFFAOYSA-N 2,4-dioxothiolane-3-carboxylic acid Chemical compound OC(=O)C1C(=O)CSC1=O JWZBKWNQNYDBBU-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
238000005554 pickling Methods 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000190150 Bipolaris sorokiniana Species 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
231100000676 disease causative agent Toxicity 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
GTLZBFQPQBLLPE-UHFFFAOYSA-N ethyl 5-methyl-2,4-dioxothiolane-3-carboxylate Chemical compound CCOC(=O)C1C(=O)SC(C)C1=O GTLZBFQPQBLLPE-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
CMNIWMBJUDZOQC-UHFFFAOYSA-N 2-methyl-3-oxobutanethioic s-acid Chemical compound CC(=O)C(C)C(S)=O CMNIWMBJUDZOQC-UHFFFAOYSA-N 0.000 description 2
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000233622 Phytophthora infestans Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000003899 bactericide agent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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 2
239000002270 dispersing agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 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
239000000417 fungicide Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000006072 paste Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
NLWLONVTAHYAPC-UHFFFAOYSA-N 2-methyl-3-oxobutanethioyl chloride Chemical compound CC(=O)C(C)C(Cl)=S NLWLONVTAHYAPC-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
VHBVBWVSCPLZQP-UHFFFAOYSA-N CC(C(C)=O)C(O)=S.Cl Chemical compound CC(C(C)=O)C(O)=S.Cl VHBVBWVSCPLZQP-UHFFFAOYSA-N 0.000 description 1
ZFAGXQVYYWOLNK-UHFFFAOYSA-N CCO[Mg] Chemical class CCO[Mg] ZFAGXQVYYWOLNK-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000760356 Chytridiomycetes Species 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000186031 Corynebacteriaceae Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000588921 Enterobacteriaceae Species 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
241000233654 Oomycetes Species 0.000 description 1
241000736122 Parastagonospora nodorum Species 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241001503460 Plasmodiophorida Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
241000947836 Pseudomonadaceae Species 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241000520648 Pyrenophora teres Species 0.000 description 1
241000231139 Pyricularia Species 0.000 description 1
241001633102 Rhizobiaceae Species 0.000 description 1
239000004113 Sepiolite Substances 0.000 description 1
241000204060 Streptomycetaceae Species 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
241001617088 Thanatephorus sasakii Species 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 description 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
150000002085 enols Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000012055 fruits and vegetables Nutrition 0.000 description 1
239000000446 fuel Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
229910052742 iron Inorganic materials 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer 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
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 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
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical class [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
239000007921 spray Substances 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
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010626 work up procedure Methods 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Detergent Compositions (AREA)
Polyurethanes Or Polyureas (AREA)
Glass Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

DD84270458A 1983-12-09 1984-12-07 Schaedlingsbekaempfungsmittel DD229582A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3344523		1983-12-09
DE19843427847 DE3427847A1 (de)	1983-12-09	1984-07-27	Thiolan-2,4-dion-3-carboxamide

Publications (1)

Publication Number	Publication Date
DD229582A5 true DD229582A5 (de)	1985-11-13

Family

ID=25816298

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84270458A DD229582A5 (de)	1983-12-09	1984-12-07	Schaedlingsbekaempfungsmittel

Country Status (19)

Country	Link
US (1)	US4599350A (cs)
EP (1)	EP0144895B1 (cs)
KR (1)	KR850004475A (cs)
AT (1)	ATE32070T1 (cs)
AU (1)	AU3588584A (cs)
BR (1)	BR8406255A (cs)
CA (1)	CA1233474A (cs)
CS (1)	CS246092B2 (cs)
DD (1)	DD229582A5 (cs)
DE (2)	DE3427847A1 (cs)
DK (1)	DK588484A (cs)
ES (1)	ES538398A0 (cs)
GR (1)	GR81206B (cs)
HU (1)	HUT37608A (cs)
IL (1)	IL73757A (cs)
NZ (1)	NZ210454A (cs)
PH (1)	PH20555A (cs)
PL (1)	PL250801A1 (cs)
PT (1)	PT79582B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1145362B (it) *	1980-03-06	1986-11-05	Sigma Tau Ind Farmaceuti	Classe di acil-derivati della carnitina procedimento per la loro preparazione e loro uso terapeutico
US4689343A (en) *	1983-12-09	1987-08-25	Bayer Aktiengesellschaft	Novel thiolane-2,4-dione-3-carboxamide fungicides
US5176738A (en) *	1990-09-17	1993-01-05	Eastman Kodak Company	Herbicidal thioparaconic acid derivatives
US5087288A (en) *	1990-09-17	1992-02-11	Eastman Kodak Company	Herbicidal thioparaconic acid derivatives
ZA200700024B (en) *	2004-05-26	2008-06-25	Fasgen Llc	Novel compounds, pharmaceutical compositions containing same, and methods of use for same
CN109415309B (zh) *	2016-06-16	2022-02-25	日产化学株式会社	磺酸酯化合物及其利用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1056268A (en) *	1963-03-06	1967-01-25	Ici Ltd	Esters of 2-oxothiophen-3-carboxylic acids
US3833610A (en) *	1972-04-21	1974-09-03	Sandoz Ag	3,5-dioxo-2,3,5,6-tetrahydro-(4h)-pyrane and thiopyrane-4-carboxanilides

1984
- 1984-07-27 DE DE19843427847 patent/DE3427847A1/de not_active Withdrawn
- 1984-11-26 AU AU35885/84A patent/AU3588584A/en not_active Abandoned
- 1984-11-27 US US06/675,159 patent/US4599350A/en not_active Expired - Fee Related
- 1984-11-27 EP EP84114309A patent/EP0144895B1/de not_active Expired
- 1984-11-27 AT AT84114309T patent/ATE32070T1/de not_active IP Right Cessation
- 1984-11-27 DE DE8484114309T patent/DE3468873D1/de not_active Expired
- 1984-11-29 PT PT79582A patent/PT79582B/pt unknown
- 1984-11-29 PH PH31512A patent/PH20555A/en unknown
- 1984-12-06 HU HU844538A patent/HUT37608A/hu not_active IP Right Cessation
- 1984-12-06 NZ NZ210454A patent/NZ210454A/en unknown
- 1984-12-06 GR GR81206A patent/GR81206B/el unknown
- 1984-12-06 IL IL73757A patent/IL73757A/xx unknown
- 1984-12-06 CS CS849449A patent/CS246092B2/cs unknown
- 1984-12-07 DK DK588484A patent/DK588484A/da not_active Application Discontinuation
- 1984-12-07 BR BR8406255A patent/BR8406255A/pt unknown
- 1984-12-07 DD DD84270458A patent/DD229582A5/de unknown
- 1984-12-07 ES ES538398A patent/ES538398A0/es active Granted
- 1984-12-07 CA CA000469552A patent/CA1233474A/en not_active Expired
- 1984-12-07 PL PL25080184A patent/PL250801A1/xx unknown
- 1984-12-08 KR KR1019840007781A patent/KR850004475A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
ES8601182A1 (es)	1985-11-01
ATE32070T1 (de)	1988-02-15
AU3588584A (en)	1985-06-13
DE3468873D1 (en)	1988-02-25
US4599350A (en)	1986-07-08
PT79582B (en)	1986-09-11
PH20555A (en)	1987-02-09
NZ210454A (en)	1987-09-30
IL73757A0 (en)	1985-03-31
IL73757A (en)	1987-11-30
HUT37608A (en)	1986-01-23
DK588484A (da)	1985-06-10
DE3427847A1 (de)	1985-06-13
CS246092B2 (en)	1986-10-16
ES538398A0 (es)	1985-11-01
EP0144895A3 (en)	1985-07-03
BR8406255A (pt)	1985-10-01
EP0144895A2 (de)	1985-06-19
DK588484D0 (da)	1984-12-07
PT79582A (en)	1984-12-01
EP0144895B1 (de)	1988-01-20
PL250801A1 (en)	1985-08-13
GR81206B (en)	1985-04-05
KR850004475A (ko)	1985-07-15
CA1233474A (en)	1988-03-01

Publication	Publication Date	Title
EP0384211B1 (de)	1994-09-07	Substituierte Acrylsäureester
DE4318917A1 (de)	1994-12-08	2-Oximino-2-phenyl-acetamide
EP0334134A1 (de)	1989-09-27	3,7-Disubstituierte Benzthiazolone
EP0331966B1 (de)	1992-09-23	Substituierte Acrylsäureester
EP0144895B1 (de)	1988-01-20	Thiolan-2,4-dion-3-carboxamide
DD140326A5 (de)	1980-02-27	Fungizide mittel
EP0277537B1 (de)	1990-09-26	1-Aminomethyl-3-aryl-4-cyano-pyrrole
DD222485A5 (de)	1985-05-22	Schaedlingsbekaempfungsmittel
DE4004035A1 (de)	1991-06-27	Substituierte 1-aminomethyl-3-aryl-4-cyano-pyrrole
EP0392286A1 (de)	1990-10-17	3-Cyano-4-phenyl-pyrrol-Derivate
EP0269916A1 (de)	1988-06-08	Saccharin-Salze von substituierten Hydroxypropylaminen
EP0274023A1 (de)	1988-07-13	Saccharin-Salze von substituierten Aminen
DD243848A5 (de)	1987-03-18	Pflanzenschutzmittel
DE3724554A1 (de)	1989-02-02	Substituierte 3-arylpyrrole
EP0319712A1 (de)	1989-06-14	N-Substituierte Dichlormaleinimide
EP0270971A2 (de)	1988-06-15	Substituierte Benzamide
EP0158957A2 (de)	1985-10-23	Allophanat-Derivate
DE3708320A1 (de)	1988-09-22	Benzaldoxim-derivate
EP0110243A1 (de)	1984-06-13	Pyrano-pyrazol-Derivate
DE3719225A1 (de)	1988-12-22	(2-cyan-2-methoximinoacetyl)-aminosaeure- derivate
DD149991A5 (de)	1981-08-12	Fungizide mittel
EP0185983A1 (de)	1986-07-02	N-(3-Chlor-1,2,4-oxadiazol-5-yl)-harnstoffe
DE3639900A1 (de)	1988-05-26	Saccharin-salze von substituierten aminen
DE3216415A1 (de)	1983-11-03	Substituierte vinyl-dithiocarbamate, ein verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DE3707687A1 (de)	1988-09-22	Benzaldoxim-carbamat-derivate