DD264842A5 - Schaedlingsbekaempfungsmittel - Google Patents

Schaedlingsbekaempfungsmittel Download PDF

Info

Publication number: DD264842A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; optionally; substituted; methyl; chain
Prior art date: 1986-12-22

Application number

DD87310860A

Other languages

German (de)

English (en)

Inventor

Joachim Weissmueller

Dieter Berg

Stefan Dutzmann

Paul Reinecke

Wilhelm Stendel

Original Assignee

��@��k��

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.)

1986-12-22

Filing date

1987-12-21

Publication date

1989-02-15

1987-12-21 Application filed by ��@��k�� filed Critical ��@��k��

1989-02-15 Publication of DD264842A5 publication Critical patent/DD264842A5/de

Links

239000002253 acid Substances 0.000 claims abstract description 17
LKRPQZOVEFZODS-UHFFFAOYSA-N 2-methyl-1,2-oxazolidine Chemical class CN1CCCO1 LKRPQZOVEFZODS-UHFFFAOYSA-N 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 10
230000003287 optical effect Effects 0.000 claims abstract description 5
239000000575 pesticide Substances 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 57
-1 piperidin-1-yl-methyl Chemical group 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 44
238000000034 method Methods 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004438 haloalkoxy group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000004995 haloalkylthio group Chemical group 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000003710 aryl alkyl 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
125000001072 heteroaryl group Chemical group 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
FCIHAZDUCCAMJI-UHFFFAOYSA-N 2-methyl-3-phenyl-5-(piperidin-1-ylmethyl)-1,2-oxazolidine Chemical compound C1C(C=2C=CC=CC=2)N(C)OC1CN1CCCCC1 FCIHAZDUCCAMJI-UHFFFAOYSA-N 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
239000004606 Fillers/Extenders Substances 0.000 claims 2
125000006163 5-membered heteroaryl group Chemical class 0.000 claims 1
125000006164 6-membered heteroaryl group Chemical class 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
238000009950 felting Methods 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000009472 formulation Methods 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
241000196324 Embryophyta Species 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
239000003085 diluting agent Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
241000238876 Acari Species 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000000417 fungicide Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
241000894007 species Species 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
231100000676 disease causative agent Toxicity 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 3
PRJUQXMARIPBGC-UHFFFAOYSA-N 4-[(2-methyl-3-phenyl-1,2-oxazolidin-5-yl)methyl]morpholine Chemical compound C1C(C=2C=CC=CC=2)N(C)OC1CN1CCOCC1 PRJUQXMARIPBGC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000221787 Erysiphe Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000258937 Hemiptera Species 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000011161 development Methods 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002546 isoxazolidines Chemical class 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
244000144972 livestock Species 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 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
230000001681 protective effect Effects 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KYGMSGYKSGNPHM-UHFFFAOYSA-N 1-prop-2-enylpiperidine Chemical compound C=CCN1CCCCC1 KYGMSGYKSGNPHM-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical compound OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
241000239223 Arachnida Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241001157813 Cercospora Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000371644 Curvularia ravenelii Species 0.000 description 2
241000255925 Diptera Species 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000257303 Hymenoptera Species 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
241000228456 Leptosphaeria Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
241000233614 Phytophthora Species 0.000 description 2
241000233626 Plasmopara 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
241001281802 Pseudoperonospora Species 0.000 description 2
241001649230 Psoroptes ovis Species 0.000 description 2
241000221300 Puccinia Species 0.000 description 2
241000228453 Pyrenophora Species 0.000 description 2
241000231139 Pyricularia Species 0.000 description 2
241000233639 Pythium Species 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
241000258242 Siphonaptera Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000579741 Sphaerotheca <fungi> Species 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000003630 growth substance Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
201000002266 mite infestation Diseases 0.000 description 2
238000002156 mixing Methods 0.000 description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
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239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 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
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960000448 lactic acid Drugs 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 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
238000004519 manufacturing process Methods 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003595 mist Substances 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
229940028444 muse Drugs 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
244000052769 pathogen Species 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008262 pumice Substances 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
239000010453 quartz 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
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000009938 salting Methods 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
230000000391 smoking effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002023 wood Substances 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- 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
- A01N43/80—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 1,2

Landscapes

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

DD87310860A 1986-12-22 1987-12-21 Schaedlingsbekaempfungsmittel DD264842A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863643957 DE3643957A1 (de)	1986-12-22	1986-12-22	Substituierte n-methylisoxazolidine

Publications (1)

Publication Number	Publication Date
DD264842A5 true DD264842A5 (de)	1989-02-15

Family

ID=6316911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87310860A DD264842A5 (de)	1986-12-22	1987-12-21	Schaedlingsbekaempfungsmittel

Country Status (11)

Country	Link
EP (1)	EP0273265A1 (da)
JP (1)	JPS63166872A (da)
KR (1)	KR880007526A (da)
AU (1)	AU8268787A (da)
BR (1)	BR8706971A (da)
DD (1)	DD264842A5 (da)
DE (1)	DE3643957A1 (da)
DK (1)	DK675687A (da)
HU (1)	HUT46691A (da)
IL (1)	IL84881A0 (da)
ZA (1)	ZA879548B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3643012A1 (de) *	1986-12-17	1988-06-30	Hoechst Ag	2,3-disubstituierte isoxazolidine, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung
DE3902615A1 (de) *	1988-08-27	1990-03-08	Bayer Ag	Aminomethyl-peptide, verfahren zur herstellung und ihre verwendung in arzneimitteln
PT97888B (pt) *	1990-06-07	1998-12-31	Zeneca Ltd	Processo para a preparacao de compostos heterociclicos derivados de indol e de composicoes farmaceuticas que os contem
US5760243A (en) *	1997-07-25	1998-06-02	Albemarle Corporation	Preparation and use of 2-methyl-5-phenylisoxazolidine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1540580A (en) *	1975-09-02	1979-02-14	Shell Int Research	Fungicidal isoxazolidines
DE3418395A1 (de) *	1984-05-17	1985-11-21	Bayer Ag, 5090 Leverkusen	Biologisch aktive mittel enthaltend substituierte isoxazolidine sowie neue isoxazolidine und ihre herstellung

1986
- 1986-12-22 DE DE19863643957 patent/DE3643957A1/de not_active Withdrawn
1987
- 1987-12-10 EP EP87118290A patent/EP0273265A1/de not_active Withdrawn
- 1987-12-16 AU AU82687/87A patent/AU8268787A/en not_active Abandoned
- 1987-12-18 JP JP62319088A patent/JPS63166872A/ja active Pending
- 1987-12-21 ZA ZA879548A patent/ZA879548B/xx unknown
- 1987-12-21 BR BR8706971A patent/BR8706971A/pt unknown
- 1987-12-21 DD DD87310860A patent/DD264842A5/de not_active IP Right Cessation
- 1987-12-21 HU HU875908A patent/HUT46691A/hu unknown
- 1987-12-21 DK DK675687A patent/DK675687A/da not_active Application Discontinuation
- 1987-12-21 IL IL84881A patent/IL84881A0/xx unknown
- 1987-12-22 KR KR870014671A patent/KR880007526A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
BR8706971A (pt)	1988-07-26
DK675687A (da)	1988-06-23
DE3643957A1 (de)	1988-06-30
KR880007526A (ko)	1988-08-27
AU8268787A (en)	1988-06-23
HUT46691A (en)	1988-11-28
DK675687D0 (da)	1987-12-21
IL84881A0 (en)	1988-06-30
ZA879548B (en)	1988-06-16
EP0273265A1 (de)	1988-07-06
JPS63166872A (ja)	1988-07-11

Legal Events

Date	Code	Title	Description
1994-12-08	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

Publication	Publication Date	Title
DE3639877A1 (de)	1988-05-26	Hetarylalkyl substituierte 5- und 6-ringheterocyclen
EP0745067A1 (de)	1996-12-04	N-pyrazolylaniline und n-pyrazolylaminopyridine als schädlingsbekämpfungsmittel
EP0300218A1 (de)	1989-01-25	Verwendung von substituierten 1,4-naphthochinonen zur Bekämpfung von Spinnentieren und Pilzen
DE4428380A1 (de)	1996-02-15	4-Trifluormethylbenzamide
EP0292822B1 (de)	1994-01-12	Substituierte Nitroalkene
EP0429968B1 (de)	1994-07-27	Heterocyclisch sustituierte Acrylsäureester
EP0421102B1 (de)	1995-03-29	Substituierte Acrylsäureester
EP0439785B1 (de)	1995-09-27	Substituierte 2-[6-(Pyrimidinyl)-indol-1-yl]-acrylsäureester
EP0373425A2 (de)	1990-06-20	Substituierte Pyridazinone, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE3642452A1 (de)	1988-06-23	Substituierte 4-amino-pyrimidine
EP0546387B1 (de)	1996-01-31	Substituierte Oximetheramide
DD264842A5 (de)	1989-02-15	Schaedlingsbekaempfungsmittel
EP0595125B1 (de)	1996-05-15	Substituierte Aza(cyclo) Alkane und ihre Verwendung als Schadlingsbekampfungsmittel
EP0545204A1 (de)	1993-06-09	2-Cyanobenzimidazole, ein Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft und neue Vorprodukte
DE4327596A1 (de)	1995-02-23	3-Methoxy-2-phenyl-acrylsäuremethylester
EP0453837B1 (de)	1996-06-19	Substituierte Pyridazinone, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
EP0572440B1 (de)	1995-08-02	Substituierte pyridylpyrimidine, deren herstellung, ihre verwendung und neue zwischenprodukte
DE4303658A1 (de)	1994-08-11	Substituierte Tetrahydropyridazincarboxamide
EP0579908B1 (de)	1997-09-10	Pyridyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
DE4227751A1 (de)	1994-02-24	1,2,4-Dithiazolium-iodide und neue Ausgangsverbindungen
EP0258631A2 (de)	1988-03-09	Alkoximinoalyklamide
DE19528778A1 (de)	1997-02-06	4-Alkyl-1,3-oxa(thia)zolin-Derivate
EP0201032A2 (de)	1986-11-12	N-Halogenalkylsulfenyl-(thio)-carbamate