DK169321B1 - Insekticide N'-substituerede N,N'-disubstituerede hydraziner, insekticidt præparat samt fremgangsmåde til bekæmpelse af insekter - Google Patents

Insekticide N'-substituerede N,N'-disubstituerede hydraziner, insekticidt præparat samt fremgangsmåde til bekæmpelse af insekter Download PDF

Info

Publication number: DK169321B1
Authority: DK; Denmark
Prior art keywords: phenyl; methyl; same; alkyl; different
Prior art date: 1987-04-15

Application number

DK201487A

Other languages

Danish (da)

English (en)

Other versions

DK201487D0 (da

DK201487A (da

Inventor

Hsu Adam Chin-Tung

Donal Wesley Hamp

Original Assignee

Rohm & Haas

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.)

1987-04-15

Filing date

1987-04-15

Publication date

1994-10-10

1987-04-15 Application filed by Rohm & Haas filed Critical Rohm & Haas

1987-04-15 Publication of DK201487D0 publication Critical patent/DK201487D0/da

1988-10-16 Publication of DK201487A publication Critical patent/DK201487A/da

1994-10-10 Application granted granted Critical

1994-10-10 Publication of DK169321B1 publication Critical patent/DK169321B1/da

Links

239000000203 mixture Substances 0.000 title claims abstract description 112
238000000034 method Methods 0.000 title claims abstract description 98
-1 N'-substituted N, N'-disubstituted hydrazines Chemical class 0.000 title claims description 59
241000238631 Hexapoda Species 0.000 title claims description 31
230000000749 insecticidal effect Effects 0.000 title claims description 26
150000001875 compounds Chemical class 0.000 claims abstract description 132
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 31
125000001153 fluoro group Chemical group F* 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 15
125000001544 thienyl group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
239000003085 diluting agent Substances 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
150000002429 hydrazines Chemical class 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
241000255777 Lepidoptera Species 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000005103 alkyl silyl group Chemical group 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(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 4
241000254173 Coleoptera Species 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 abstract description 22
239000002904 solvent Substances 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000002585 base Substances 0.000 description 31
239000000243 solution Substances 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
238000002360 preparation method Methods 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
238000009472 formulation Methods 0.000 description 22
239000002253 acid Substances 0.000 description 20
231100000167 toxic agent Toxicity 0.000 description 20
239000003440 toxic substance Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
239000012442 inert solvent Substances 0.000 description 17
239000000047 product Substances 0.000 description 16
125000001424 substituent group Chemical group 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
150000001298 alcohols Chemical class 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
239000013543 active substance Substances 0.000 description 13
239000007788 liquid Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000004615 ingredient Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
150000002170 ethers Chemical class 0.000 description 9
239000012535 impurity Substances 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
239000008187 granular material Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
239000000969 carrier Substances 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
239000002917 insecticide Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
239000008096 xylene Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
239000000463 material Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
230000000361 pesticidal effect Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000779 smoke Substances 0.000 description 6
238000005507 spraying Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000012628 flowing agent Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 4
241001143309 Acanthoscelides obtectus Species 0.000 description 4
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000000975 dye Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
239000000376 reactant Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
241000894007 species Species 0.000 description 4
238000000967 suction filtration Methods 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
238000012360 testing method Methods 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
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 3
241001477931 Mythimna unipuncta Species 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
235000005687 corn oil Nutrition 0.000 description 3
239000012530 fluid Substances 0.000 description 3
150000007857 hydrazones Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
239000006072 paste Substances 0.000 description 3
125000003884 phenylalkyl group Chemical group 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
JCIDDVXYYNKJOV-UHFFFAOYSA-N trimethylsilylmethylhydrazine Chemical compound C[Si](C)(C)CNN JCIDDVXYYNKJOV-UHFFFAOYSA-N 0.000 description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
GRRIYLZJLGTQJX-UHFFFAOYSA-N 1,2-dibenzoylhydrazine Chemical compound C=1C=CC=CC=1C(=O)NNC(=O)C1=CC=CC=C1 GRRIYLZJLGTQJX-UHFFFAOYSA-N 0.000 description 2
ALHUXMDEZNLFTA-UHFFFAOYSA-N 2-methylquinoxaline Chemical compound C1=CC=CC2=NC(C)=CN=C21 ALHUXMDEZNLFTA-UHFFFAOYSA-N 0.000 description 2
YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 2
MFFVZXOPRXMVET-UHFFFAOYSA-N 4-methylbenzohydrazide Chemical compound CC1=CC=C(C(=O)NN)C=C1 MFFVZXOPRXMVET-UHFFFAOYSA-N 0.000 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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150000002731 mercury compounds Chemical class 0.000 description 1
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QWNADYWYMJGNAC-UHFFFAOYSA-N methyl(naphthalen-1-yl)carbamic acid Chemical class C1=CC=C2C(N(C(O)=O)C)=CC=CC2=C1 QWNADYWYMJGNAC-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 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
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
GPXSLAGFIDUFCU-UHFFFAOYSA-N n',n'-dibenzoylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NN(C(=O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 GPXSLAGFIDUFCU-UHFFFAOYSA-N 0.000 description 1
DOKUCVZILGCEES-UHFFFAOYSA-N n'-acetyl-n'-(4-nitrophenyl)benzohydrazide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(C(=O)C)NC(=O)C1=CC=CC=C1 DOKUCVZILGCEES-UHFFFAOYSA-N 0.000 description 1
QLFORKOADGIJGQ-UHFFFAOYSA-N n'-benzoyl-n'-(cyclohexylmethyl)benzohydrazide Chemical class C=1C=CC=CC=1C(=O)NN(C(=O)C=1C=CC=CC=1)CC1CCCCC1 QLFORKOADGIJGQ-UHFFFAOYSA-N 0.000 description 1
QNTKMJGJEUWGLG-UHFFFAOYSA-N n'-benzoyl-n'-cyclohexylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NN(C(=O)C=1C=CC=CC=1)C1CCCCC1 QNTKMJGJEUWGLG-UHFFFAOYSA-N 0.000 description 1
HSPCCASGCDMMSH-UHFFFAOYSA-N n'-benzoyl-n'-ethylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)N(CC)NC(=O)C1=CC=CC=C1 HSPCCASGCDMMSH-UHFFFAOYSA-N 0.000 description 1
FLFIIAUKAIRKFR-UHFFFAOYSA-N n'-benzoyl-n-tert-butyl-4-nitrobenzohydrazide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=CC=C1 FLFIIAUKAIRKFR-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
XYFMGGWVGACNEC-UHFFFAOYSA-N n-carbamoyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C(=O)N)C(=O)C1=CC=CC=C1 XYFMGGWVGACNEC-UHFFFAOYSA-N 0.000 description 1
ARDNTAZQAKTAJQ-UHFFFAOYSA-N n-cyclohexylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)N(N)C1CCCCC1 ARDNTAZQAKTAJQ-UHFFFAOYSA-N 0.000 description 1
WCWZBEKOCXYUAP-UHFFFAOYSA-N n-propan-2-ylbenzohydrazide Chemical compound CC(C)N(N)C(=O)C1=CC=CC=C1 WCWZBEKOCXYUAP-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100001160 nonlethal Toxicity 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
239000002245 particle Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000003090 pesticide formulation Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
XEBWQGVWTUSTLN-UHFFFAOYSA-M phenylmercury acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1 XEBWQGVWTUSTLN-UHFFFAOYSA-M 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
239000003128 rodenticide Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
229910052815 sulfur oxide Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000002641 tar oil Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- A01N37/28—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 containing the group; 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
- A01N37/34—Nitriles
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK201487A 1987-04-15 1987-04-15 Insekticide N'-substituerede N,N'-disubstituerede hydraziner, insekticidt præparat samt fremgangsmåde til bekæmpelse af insekter DK169321B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP87303296		1987-04-15
EP87303296A EP0286746B1 (de)	1987-04-15	1987-04-15	Insektizide N-(gegebenenfalls substituierte)-N'-substituierte-N,N'-disubstituierte Hydrazine

Publications (3)

Publication Number	Publication Date
DK201487D0 DK201487D0 (da)	1987-04-15
DK201487A DK201487A (da)	1988-10-16
DK169321B1 true DK169321B1 (da)	1994-10-10

Family

ID=8197862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK201487A DK169321B1 (da)	1987-04-15	1987-04-15	Insekticide N'-substituerede N,N'-disubstituerede hydraziner, insekticidt præparat samt fremgangsmåde til bekæmpelse af insekter

Country Status (9)

Country	Link
EP (1)	EP0286746B1 (de)
AT (1)	ATE61044T1 (de)
DE (1)	DE3768264D1 (de)
DK (1)	DK169321B1 (de)
ES (1)	ES2022342B3 (de)
GR (1)	GR3001522T3 (de)
HU (1)	HU202719B (de)
PT (1)	PT84965B (de)
TR (1)	TR23597A (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0398842A1 (de) *	1989-05-16	1990-11-22	Ciba-Geigy Ag	Hydrazid-derivate
CA2043775A1 (en) *	1990-06-14	1991-12-15	Dat P. Le	Dibenzoylakylcyanohydrazines
NZ240155A (en) *	1990-10-29	1992-10-28	Ishihara Sangyo Kaisha	Heterocyclyl acyl and (hexahydro) indanyl acyl substituted hydrazine derivatives, preparation thereof and pesticidal compositions
IL100643A (en) *	1991-01-25	1996-10-31	Nippon Kayaku Kk	History of hydrazine and pesticides containing these histories as an active ingredient
DE69400789T2 (de) *	1993-07-20	1997-02-20	Nippon Kayaku Kk	Verfahren zur Herstellung von in 2-Stellung substituierten 1-Acylhydrazinen
IL110427A (en) *	1993-08-11	1998-10-30	Rohm & Haas	Process for the preparation of 1,2-diacyl-T-2-alkyl hydrazides
US7304161B2 (en)	2003-02-10	2007-12-04	Intrexon Corporation	Diaclhydrazine ligands for modulating the expression of exogenous genes in mammalian systems via an ecdysone receptor complex
US7456315B2 (en)	2003-02-28	2008-11-25	Intrexon Corporation	Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
US9127024B2 (en)	2013-03-15	2015-09-08	Intrexon Corporation	Boron-containing diacylhydrazines
CN103274963B (zh) *	2013-06-28	2015-12-23	江苏倍达医药科技有限公司	一种合成1，1，1-三氟异丙基肼盐酸盐的方法
AU2015317862A1 (en)	2014-09-17	2017-04-06	Intrexon Corporation	Boron-containing diacylhydrazine compounds
CN107098894B (zh) *	2017-04-25	2019-07-09	西华大学	N-(2-噻吩基)亚甲基-2-氰基-3-杂环基丙烯酰肼类衍生物及其应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3228631A1 (de) *	1982-07-31	1984-02-02	Hoechst Ag, 6230 Frankfurt	Neue (di)-thiophosphor- und phosphonsaeure-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung im pflanzenschutz

1987
- 1987-04-15 AT AT87303296T patent/ATE61044T1/de not_active IP Right Cessation
- 1987-04-15 ES ES87303296T patent/ES2022342B3/es not_active Expired - Lifetime
- 1987-04-15 EP EP87303296A patent/EP0286746B1/de not_active Expired - Lifetime
- 1987-04-15 DE DE8787303296T patent/DE3768264D1/de not_active Expired - Lifetime
- 1987-04-15 DK DK201487A patent/DK169321B1/da not_active IP Right Cessation
- 1987-05-28 PT PT84965A patent/PT84965B/pt not_active IP Right Cessation
- 1987-06-18 TR TR411/87A patent/TR23597A/xx unknown
- 1987-07-16 HU HU873251A patent/HU202719B/hu not_active IP Right Cessation
1991
- 1991-02-28 GR GR90401183T patent/GR3001522T3/el unknown

Also Published As

Publication number	Publication date
DK201487D0 (da)	1987-04-15
EP0286746A1 (de)	1988-10-19
DE3768264D1 (de)	1991-04-04
GR3001522T3 (en)	1992-11-23
HUT47370A (en)	1989-03-28
TR23597A (tr)	1990-04-20
EP0286746B1 (de)	1991-02-27
ES2022342B3 (es)	1991-12-01
PT84965A (en)	1988-04-21
DK201487A (da)	1988-10-16
PT84965B (pt)	1992-07-31
ATE61044T1 (de)	1991-03-15
HU202719B (en)	1991-04-29

Legal Events

Date	Code	Title	Description
1994-10-10	B1	Patent granted (law 1993)
2007-04-30	PUP	Patent expired

Publication	Publication Date	Title
JP2509583B2 (ja)	1996-06-19	殺虫性化合物およびそれを含む殺虫組成物
AU602505B2 (en)	1990-10-18	Hydrazine derivatives
DK169321B1 (da)	1994-10-10	Insekticide N'-substituerede N,N'-disubstituerede hydraziner, insekticidt præparat samt fremgangsmåde til bekæmpelse af insekter
DE3779814T2 (de)	1993-02-04	Insektentoetende n-substituierte-n'-substituierte-n,n'-diacylhydrazine.
KR910000856B1 (ko)	1991-02-11	살충제 n'-치환-n-알킬카르보닐-n-아실히드라진
DE68908789T2 (de)	1994-04-14	Insectizide N'-substituierte-N-alkylcarbonyl-N'-acylhydrazine und N'-substituierte-N-acyl-N'-alkylcarbonyl hydrazine.
AU595303B2 (en)	1990-03-29	Six-membered n-heterocyclic derivatives of n'-substituted-n, n'-diacylhydrazines
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