DD273969A5 - Verwendung von halogenalkyl-, alkenyl- und alkinylazole als synergisten zur schaedlingsbekaempfung - Google Patents

Verwendung von halogenalkyl-, alkenyl- und alkinylazole als synergisten zur schaedlingsbekaempfung Download PDF

Info

Publication number: DD273969A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; halogen; formula; vii; carbon atoms
Prior art date: 1987-01-14

Application number

DD88312190A

Other languages

German (de)

English (en)

Inventor

Udo Kraatz

Wolfgang Behrenz

Carl Fedtke

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.)

1987-01-14

Filing date

1988-01-12

Publication date

1989-12-06

1988-01-12 Application filed by ��@��k�� filed Critical ��@��k��

1989-12-06 Publication of DD273969A5 publication Critical patent/DD273969A5/de

Links

150000003839 salts Chemical class 0.000 claims abstract description 36
239000001257 hydrogen Substances 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
125000005389 trialkylsiloxy group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
239000000460 chlorine Substances 0.000 claims description 81
-1 chloro, methyl Chemical group 0.000 claims description 59
125000004432 carbon atom Chemical group C* 0.000 claims description 46
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002367 halogens Chemical group 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
229910052801 chlorine Inorganic materials 0.000 claims description 28
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
241000607479 Yersinia pestis Species 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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 3
125000001495 ethyl group Chemical group [H]C([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 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
125000004966 cyanoalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 4
239000000575 pesticide Substances 0.000 abstract description 4
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract description 3
150000001875 compounds Chemical class 0.000 description 60
238000000034 method Methods 0.000 description 41
239000004480 active ingredient Substances 0.000 description 35
239000000203 mixture Substances 0.000 description 26
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
241000196324 Embryophyta Species 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 18
230000002363 herbicidal effect Effects 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
229910052794 bromium Inorganic materials 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000013543 active substance Substances 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
238000009472 formulation Methods 0.000 description 13
241001465754 Metazoa Species 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
239000003085 diluting agent Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
230000002195 synergetic effect Effects 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000004009 herbicide Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
125000004093 cyano group Chemical group *C#N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
229910052751 metal Chemical class 0.000 description 8
239000002184 metal Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
LEBXSRJXGRZVLM-UHFFFAOYSA-N 4-methoxy-2-propan-2-ylpyrimidine Chemical compound COC1=CC=NC(C(C)C)=N1 LEBXSRJXGRZVLM-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003814 drug Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
241000238421 Arthropoda Species 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 6
DKEKURXRUXRNES-UHFFFAOYSA-N bis(1h-pyrrol-2-yl)methanone Chemical class C=1C=CNC=1C(=O)C1=CC=CN1 DKEKURXRUXRNES-UHFFFAOYSA-N 0.000 description 6
238000003197 gene knockdown Methods 0.000 description 6
150000003014 phosphoric acid esters Chemical class 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000001733 carboxylic acid esters Chemical class 0.000 description 5
239000000890 drug combination Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
WELHGGCWMGGKGH-UHFFFAOYSA-N 1-(2-chloro-3,3-dimethylbut-1-enyl)-1,2,4-triazole Chemical compound CC(C)(C)C(Cl)=CN1C=NC=N1 WELHGGCWMGGKGH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000257229 Musca <genus> Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000000969 carrier Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
125000004663 dialkyl amino group Chemical group 0.000 description 4
239000011521 glass Substances 0.000 description 4
150000002366 halogen compounds Chemical class 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000003921 oil Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000000547 substituted alkyl group Chemical group 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
GNDDPQONHZKTJA-UHFFFAOYSA-N 2-(2-chloroethenyl)-1h-pyrrole Chemical class ClC=CC1=CC=CN1 GNDDPQONHZKTJA-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
229910000102 alkali metal hydride Inorganic materials 0.000 description 3
150000008046 alkali metal hydrides Chemical class 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000003973 alkyl amines Chemical group 0.000 description 3
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 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
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
229940008406 diethyl sulfate Drugs 0.000 description 3
150000003948 formamides Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
229910000105 potassium hydride Inorganic materials 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 2
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
241000239223 Arachnida Species 0.000 description 2
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 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
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241000258937 Hemiptera Species 0.000 description 2
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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 2
235000021506 Ipomoea Nutrition 0.000 description 2
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240000007218 Ipomoea hederacea Species 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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235000002634 Solanum Nutrition 0.000 description 2
241000207763 Solanum Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
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239000000642 acaricide Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical class 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
238000010171 animal model Methods 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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229910052796 boron Inorganic materials 0.000 description 2
239000001273 butane Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
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239000000706 filtrate Substances 0.000 description 2
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150000008282 halocarbons Chemical class 0.000 description 2
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
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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 2
239000002547 new drug Substances 0.000 description 2
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239000001301 oxygen Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
150000003008 phosphonic acid esters Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
230000029553 photosynthesis Effects 0.000 description 2
238000010672 photosynthesis Methods 0.000 description 2
230000000243 photosynthetic effect Effects 0.000 description 2
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229960005235 piperonyl butoxide Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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235000012976 tarts Nutrition 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

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Organic Chemistry (AREA)
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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)
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Plural Heterocyclic Compounds (AREA)

DD88312190A 1987-01-14 1988-01-12 Verwendung von halogenalkyl-, alkenyl- und alkinylazole als synergisten zur schaedlingsbekaempfung DD273969A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873700916 DE3700916A1 (de)	1987-01-14	1987-01-14	Halogenalkyl-, alkenyl- und alkinyl-azole

Publications (1)

Publication Number	Publication Date
DD273969A5 true DD273969A5 (de)	1989-12-06

Family

ID=6318820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88312190A DD273969A5 (de)	1987-01-14	1988-01-12	Verwendung von halogenalkyl-, alkenyl- und alkinylazole als synergisten zur schaedlingsbekaempfung

Country Status (10)

Country	Link
EP (1)	EP0275866A1 (da)
JP (1)	JPS63208577A (da)
KR (1)	KR880008992A (da)
AU (1)	AU1015088A (da)
BR (1)	BR8800112A (da)
DD (1)	DD273969A5 (da)
DE (1)	DE3700916A1 (da)
DK (1)	DK14288A (da)
IL (1)	IL85059A0 (da)
ZA (1)	ZA88206B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3819903A1 (de) *	1988-06-11	1989-12-21	Basf Ag	1-halogen-1-azolyl-ethan-derivate und diese enthaltende fungizide
DE3923151A1 (de) *	1989-07-13	1991-01-24	Basf Ag	1,2-dihalogenazolylethanderivate und diese enthaltende pflanzenschutzmittel
DE3913725A1 (de) *	1989-04-26	1990-10-31	Basf Ag	1-halogenvinyl-azole und diese enthaltende fungizide und wachstumsregulatoren
AU682711B2 (en) *	1993-10-07	1997-10-16	Shell Internationale Research Maatschappij B.V.	Pesticidal methods and compositions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE49744B1 (en) *	1979-02-22	1985-12-11	Wellcome Found	Imidazole derivatives and salts thereof,their synthesis,and pharmaceutical formulations
DE3362868D1 (en) *	1982-02-19	1986-05-15	Ciba Geigy Ag	Microbicidal and plant-growth regulating agents
DE3417468A1 (de) *	1984-05-11	1985-11-14	Bayer Ag, 5090 Leverkusen	Azolylvinylether
DE3525978A1 (de) *	1985-07-20	1987-01-29	Bayer Ag	Azolyl-alkene und -alkine

1987
- 1987-01-14 DE DE19873700916 patent/DE3700916A1/de not_active Withdrawn
1988
- 1988-01-05 EP EP88100037A patent/EP0275866A1/de not_active Withdrawn
- 1988-01-08 AU AU10150/88A patent/AU1015088A/en not_active Abandoned
- 1988-01-11 JP JP63002657A patent/JPS63208577A/ja active Pending
- 1988-01-11 IL IL85059A patent/IL85059A0/xx unknown
- 1988-01-12 DD DD88312190A patent/DD273969A5/de unknown
- 1988-01-13 KR KR1019880000164A patent/KR880008992A/ko not_active Withdrawn
- 1988-01-13 BR BR8800112A patent/BR8800112A/pt unknown
- 1988-01-13 ZA ZA880206A patent/ZA88206B/xx unknown
- 1988-01-13 DK DK014288A patent/DK14288A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK14288A (da)	1988-07-15
AU1015088A (en)	1988-07-21
DE3700916A1 (de)	1988-07-28
KR880008992A (ko)	1988-09-13
BR8800112A (pt)	1988-08-23
IL85059A0 (en)	1988-06-30
EP0275866A1 (de)	1988-07-27
JPS63208577A (ja)	1988-08-30
DK14288D0 (da)	1988-01-13
ZA88206B (en)	1988-06-30

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EP0126235A1 (de)	1984-11-28	Neue fünfgliedrige stickstoffhaltige Heterocyclen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Schädlingsbekämpfungsmittel
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US4783474A (en)	1988-11-08	Halogenoalkyl-, alkenyl- and alkinyl-azoles
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DE3525978A1 (de)	1987-01-29	Azolyl-alkene und -alkine