DD209717A5 - Schaedlingsbekaempfungsmittel - Google Patents

Schaedlingsbekaempfungsmittel Download PDF

Info

Publication number: DD209717A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; halogen; alkyl; formula; haloalkyl
Prior art date: 1982-05-18

Application number

DD83250945A

Other languages

German (de)

English (en)

Inventor

Siegfried Oeckl

Paul Reinecke

Wilhelm Brandes

Karl-Heinz Kuck

Wilfried Paulus

Hermann Genth

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.)

1982-05-18

Filing date

1983-05-16

Publication date

1984-05-23

1983-05-16 Application filed by Bayer Ag filed Critical Bayer Ag

1984-05-23 Publication of DD209717A5 publication Critical patent/DD209717A5/de

Links

229910052736 halogen Inorganic materials 0.000 claims abstract description 21
150000002367 halogens Chemical class 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
238000002360 preparation method Methods 0.000 claims abstract description 14
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 7
241000607479 Yersinia pestis Species 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
239000000575 pesticide Substances 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 38
239000000460 chlorine Substances 0.000 claims description 32
-1 nitro, methyl Chemical group 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 19
239000000463 material Substances 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
241000251730 Chondrichthyes Species 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
125000000094 2-phenylethyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
230000000361 pesticidal effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 37
239000002904 solvent Substances 0.000 abstract description 12
239000000126 substance Substances 0.000 abstract description 10
MTEWKKSTWKALQI-UHFFFAOYSA-N n-prop-2-ynylformamide Chemical class O=CNCC#C MTEWKKSTWKALQI-UHFFFAOYSA-N 0.000 abstract description 8
239000003795 chemical substances by application Substances 0.000 abstract description 7
239000000417 fungicide Substances 0.000 abstract description 5
230000002140 halogenating effect Effects 0.000 abstract description 5
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
239000003899 bactericide agent Substances 0.000 abstract description 3
150000002431 hydrogen Chemical group 0.000 abstract 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000003995 emulsifying agent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000009472 formulation Methods 0.000 description 9
239000000243 solution Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
241000233866 Fungi Species 0.000 description 7
244000005700 microbiome Species 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000008272 agar Substances 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000005554 pickling Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002689 soil Substances 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000736122 Parastagonospora nodorum Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000589652 Xanthomonas oryzae Species 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
241001459558 Monographella nivalis Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
230000004075 alteration Effects 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
229910052796 boron Inorganic materials 0.000 description 2
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
239000011111 cardboard Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000003898 horticulture Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
230000003641 microbiacidal effect Effects 0.000 description 2
239000011707 mineral Substances 0.000 description 2
RKPTVPMKIIDNFM-UHFFFAOYSA-N n-phenylbut-3-ynamide Chemical compound C#CCC(=O)NC1=CC=CC=C1 RKPTVPMKIIDNFM-UHFFFAOYSA-N 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000000123 paper Substances 0.000 description 2
239000003495 polar organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
DHHKPEUQJIEKOA-UHFFFAOYSA-N tert-butyl 2-[6-(nitromethyl)-6-bicyclo[3.2.0]hept-3-enyl]acetate Chemical compound C1C=CC2C(CC(=O)OC(C)(C)C)(C[N+]([O-])=O)CC21 DHHKPEUQJIEKOA-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000002023 wood Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KANAPVJGZDNSCZ-UHFFFAOYSA-N 1,2-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)N=CC2=C1 KANAPVJGZDNSCZ-UHFFFAOYSA-N 0.000 description 1
JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
OMNGRPHPKWAMSY-UHFFFAOYSA-N 1-chloroprop-1-yne Chemical compound CC#CCl OMNGRPHPKWAMSY-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
KEBUEWXZQBMCNB-UHFFFAOYSA-N 1h-benzimidazol-2-yl carbamate Chemical class C1=CC=C2NC(OC(=O)N)=NC2=C1 KEBUEWXZQBMCNB-UHFFFAOYSA-N 0.000 description 1
229940061334 2-phenylphenol Drugs 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
RQCLKJICDPMGDH-UHFFFAOYSA-N 7-(dichloromethyl)-2-fluoro-3-sulfanylideneisoindol-1-one Chemical compound S=C1N(F)C(=O)C2=C1C=CC=C2C(Cl)Cl RQCLKJICDPMGDH-UHFFFAOYSA-N 0.000 description 1
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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
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
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239000005749 Copper compound Substances 0.000 description 1
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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229920000084 Gum arabic Polymers 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
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150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
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150000008052 alkyl sulfonates Chemical class 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
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239000001273 butane Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 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
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000002826 coolant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000005068 cooling lubricant Substances 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000006731 degradation reaction Methods 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
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-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
OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 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
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
239000000446 fuel Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012770 industrial material Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010985 leather Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [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
238000004519 manufacturing process Methods 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000155 melt 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
230000000813 microbial effect Effects 0.000 description 1
239000002855 microbicide agent Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
QPXDNETVBVKDEK-UHFFFAOYSA-N n-bromo-n-phenylbut-3-ynamide Chemical compound C#CCC(=O)N(Br)C1=CC=CC=C1 QPXDNETVBVKDEK-UHFFFAOYSA-N 0.000 description 1
IEUXQNMEVFIYKM-UHFFFAOYSA-N n-bromo-n-prop-2-ynylformamide Chemical compound O=CN(Br)CC#C IEUXQNMEVFIYKM-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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 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
235000010292 orthophenyl phenol Nutrition 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
229940070805 p-chloro-m-cresol Drugs 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LDAKDHFODVFZFV-UHFFFAOYSA-M potassium formylazanide Chemical compound [K]NC=O LDAKDHFODVFZFV-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000003531 protein hydrolysate Substances 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
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000000565 sealant Substances 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
235000019355 sepiolite Nutrition 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000009331 sowing Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009369 viticulture Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/88—Carboxylic acid amides having nitrogen atoms of carboxamide groups bound to an acyclic carbon atom and to a carbon atom of a six-membered aromatic ring wherein at least one ortho-hydrogen atom has been replaced
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/03—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to hydrogen atoms

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD83250945A 1982-05-18 1983-05-16 Schaedlingsbekaempfungsmittel DD209717A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3218611		1982-05-18
DE19823236522 DE3236522A1 (de)	1982-05-18	1982-10-02	Halogenpropargylformamide

Publications (1)

Publication Number	Publication Date
DD209717A5 true DD209717A5 (de)	1984-05-23

Family

ID=25801890

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83250945A DD209717A5 (de)	1982-05-18	1983-05-16	Schaedlingsbekaempfungsmittel

Country Status (14)

Country	Link
US (1)	US4661632A (fr)
EP (1)	EP0094539B1 (fr)
AU (1)	AU556630B2 (fr)
BR (1)	BR8302604A (fr)
CA (1)	CA1213612A (fr)
DD (1)	DD209717A5 (fr)
DE (2)	DE3236522A1 (fr)
DK (1)	DK218483A (fr)
ES (1)	ES8402812A1 (fr)
GR (1)	GR77484B (fr)
IL (1)	IL68708A0 (fr)
NZ (1)	NZ204239A (fr)
PL (1)	PL135140B1 (fr)
PT (1)	PT76660B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02504281A (ja) *	1988-05-18	1990-12-06	フセソユズニ　ナウチノ‐イススレドバテルスキ　インスティテュト　ヒミチェスキフ　スレドストフ　ザスチティ　ラステニ	置換されたフェニルアルキルホルムアミド類及びそれらを基材とする殺カビ製剤
US4945109A (en) *	1988-08-24	1990-07-31	Buckman Laboratories International, Inc.	Ester of carbamic acid useful as a microbicide and a preservative
US5321151A (en) *	1993-06-14	1994-06-14	Rohm And Haas Company	Process for preparation of iodopropargyl carbamates
US5326899A (en) *	1993-06-14	1994-07-05	Rohm And Haas Company	Process for preparation of iodopropargyl carbamates
US5733935A (en) *	1995-06-29	1998-03-31	Nihon Nohyaku Co., Ltd.	Hydroxylamine derivatives and fungicides containing the same
WO2005027635A1 (fr) *	2003-09-19	2005-03-31	Arch Chemicals, Inc.	Compositions d'halopropynyle stabilisees en tant qu'agents de conservation

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2251205A1 (de) *	1972-10-19	1974-05-02	Celamerck Gmbh & Co Kg	Formamidderivate und ihre herstellung
EP0010673B1 (fr) *	1978-10-31	1982-01-27	Bayer Ag	N-Propargyl-anilines substituées, procédé pour leur préparation et leur utilisation comme fongicides
DE2919196A1 (de) *	1979-05-12	1980-11-20	Bayer Ag	N-alkinyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide

1982
- 1982-10-02 DE DE19823236522 patent/DE3236522A1/de not_active Withdrawn
1983
- 1983-05-02 DE DE8383104270T patent/DE3360604D1/de not_active Expired
- 1983-05-02 EP EP83104270A patent/EP0094539B1/fr not_active Expired
- 1983-05-09 PT PT76660A patent/PT76660B/pt unknown
- 1983-05-16 DD DD83250945A patent/DD209717A5/de unknown
- 1983-05-16 NZ NZ204239A patent/NZ204239A/en unknown
- 1983-05-16 PL PL1983242011A patent/PL135140B1/pl unknown
- 1983-05-16 GR GR71358A patent/GR77484B/el unknown
- 1983-05-16 IL IL68708A patent/IL68708A0/xx unknown
- 1983-05-16 CA CA000428255A patent/CA1213612A/fr not_active Expired
- 1983-05-17 DK DK218483A patent/DK218483A/da not_active Application Discontinuation
- 1983-05-17 BR BR8302604A patent/BR8302604A/pt unknown
- 1983-05-17 ES ES522474A patent/ES8402812A1/es not_active Expired
- 1983-05-18 AU AU14636/83A patent/AU556630B2/en not_active Ceased
1985
- 1985-10-31 US US06/793,600 patent/US4661632A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3360604D1 (de)	1985-09-26
BR8302604A (pt)	1984-01-17
CA1213612A (fr)	1986-11-04
PT76660B (en)	1986-01-10
EP0094539B1 (fr)	1985-08-21
DK218483D0 (da)	1983-05-17
PT76660A (en)	1983-06-01
DK218483A (da)	1983-11-19
NZ204239A (en)	1985-03-20
ES522474A0 (es)	1984-03-01
ES8402812A1 (es)	1984-03-01
US4661632A (en)	1987-04-28
DE3236522A1 (de)	1983-11-24
PL242011A1 (en)	1984-07-02
GR77484B (fr)	1984-09-24
IL68708A0 (en)	1983-09-30
EP0094539A1 (fr)	1983-11-23
PL135140B1 (en)	1985-10-31
AU556630B2 (en)	1986-11-13
AU1463683A (en)	1983-11-24

Publication	Publication Date	Title
EP0165448B1 (fr)	1991-10-16	1-Hétéroaryl-4-aryl-pyrazolin-5-ones
EP0037971B1 (fr)	1983-12-21	Cyanoguanidines trisubstituées, procédé pour leur préparation et leur utilisation comme fongicides
EP0094552B1 (fr)	1985-07-24	Sels d'ammonium iodopropargyle, préparation et utilisation pesticide
EP0094539B1 (fr)	1985-08-21	Halogénopropargylformamides
EP0121054B1 (fr)	1986-12-03	N-sulfényl-hydantoines, procédé de leur préparation et leur application comme microbicide
EP0075172B1 (fr)	1985-05-29	N-Sulfényle benzylsulfonamides, préparation et utilisation microbicide
EP0106093B1 (fr)	1986-11-20	Iodopropargylsulfamide
DE3216416A1 (de)	1983-11-03	Heteroarylthiovinyl-verbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DE4004035A1 (de)	1991-06-27	Substituierte 1-aminomethyl-3-aryl-4-cyano-pyrrole
DE3413897A1 (de)	1985-10-17	(beta)-naphthylalkylamine
EP0046557B1 (fr)	1984-02-22	N-sulfénylurées, procédé de préparation, compositions fongicides et utilisation
EP0003975B1 (fr)	1981-05-13	Diamides de l'acide dichloromaléique, procédé pour les préparer et leur utilisation comme fongicides
EP0161480B1 (fr)	1987-06-03	N-iodepropargyl-chlorométhanesulfonamide
EP0014887B1 (fr)	1981-10-14	Dérivés spiro de 3-(3,5-dihalogénophényl)-oxazolidine-2-thion-4-ones, procédés pour leur préparation et leur utilisation comme fongicides
EP0195238B1 (fr)	1989-03-29	Indazoles N-sulfénylés fluorés, leur procédé de préparation et leur application
EP0055429B1 (fr)	1984-03-14	Allophanates N-sulfénylés, procédé pour leur préparation et leur utilisation comme fongicides
DE3414881A1 (de)	1985-10-24	Allophanat-derivate
EP0162366B1 (fr)	1988-06-22	Carbamates sulphénylés, préparation et utilisation
EP0012261A1 (fr)	1980-06-25	Dérivés spiro substitués de 3-(3,5-dichlorophényl)-2,4-oxazolidine diones, procédés pour leur préparation et leur utilisation comme fongicides
EP0529400A1 (fr)	1993-03-03	3-(2-chlor-3-trifluorméthyl)-4-cyanopyrrole, comme insecticides
DE3146231A1 (de)	1983-05-26	N-sulfenylierte biuret-n"-carbonsaeureester, ein verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
EP0013322A1 (fr)	1980-07-23	Oxydes de 3,4-dioxo-1,2,5-thiadiazolidine-1, (I), leur préparation et leur application comme fongicides, compositions fongicides contenant les composés (I) et la préparation de ces compositions
DE3122176A1 (de)	1982-12-30	"substituierte 1-jod-1-butin-4-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel"