SK281481B6 - Amidová zlúčenina a jej soli, spôsob jej prípravy a pesticídny prostriedok s jej obsahom - Google Patents

Amidová zlúčenina a jej soli, spôsob jej prípravy a pesticídny prostriedok s jej obsahom Download PDF

Info

Publication number: SK281481B6
Authority: SK; Slovakia
Prior art keywords: group; substituted; alkyl; alkoxy; unsubstituted
Prior art date: 1992-07-23

Application number

SK750-93A

Other languages

English (en)

Slovak (sk)

Other versions

SK75093A3 (en

Inventor

Tadaaki Toki

Toru Koyanagi

Masayuki Morita

Tetsuo Yoneda

Chiharu Kagimoto

Hiroshi Okada

Original Assignee

Ishihara Sangyo Kaisha Ltd.

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.)

1992-07-23

Filing date

1993-07-15

Publication date

2001-04-09

1993-07-15 Application filed by Ishihara Sangyo Kaisha Ltd. filed Critical Ishihara Sangyo Kaisha Ltd.

1994-06-08 Publication of SK75093A3 publication Critical patent/SK75093A3/sk

2001-04-09 Publication of SK281481B6 publication Critical patent/SK281481B6/sk

Links

-1 Amide compounds Chemical class 0.000 title claims abstract description 111
150000003839 salts Chemical class 0.000 title claims abstract description 30
238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 20
230000000361 pesticidal effect Effects 0.000 title claims description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 98
125000003545 alkoxy group Chemical group 0.000 claims abstract description 54
125000003118 aryl group Chemical group 0.000 claims abstract description 51
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 33
229910052717 sulfur Chemical group 0.000 claims abstract description 25
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 14
125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 83
239000000203 mixture Substances 0.000 claims description 55
239000004480 active ingredient Substances 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 29
241000238631 Hexapoda Species 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 22
125000005843 halogen group Chemical group 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
125000003277 amino group Chemical group 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
JUIWZYBJXUPIKF-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC=C1C(F)(F)F JUIWZYBJXUPIKF-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000005110 aryl thio group Chemical group 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
125000003739 carbamimidoyl group Chemical class C(N)(=N)* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical class Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000006387 trifluoromethyl pyridyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
LMRJHNFECNKDKH-UHFFFAOYSA-N 4-(trifluoromethyl)nicotinic acid Chemical compound OC(=O)C1=CN=CC=C1C(F)(F)F LMRJHNFECNKDKH-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
KXFDDTJTNOAVEK-UHFFFAOYSA-N n-acetyl-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC(=O)NC(=O)C1=CN=CC=C1C(F)(F)F KXFDDTJTNOAVEK-UHFFFAOYSA-N 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 10
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
125000003282 alkyl amino group Chemical group 0.000 claims 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
125000005103 alkyl silyl group Chemical group 0.000 claims 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
150000002431 hydrogen Chemical class 0.000 claims 3
MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical group NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 claims 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
150000005840 aryl radicals Chemical class 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims 1
TUXUVCWYZALXIE-UHFFFAOYSA-N n-(2-amino-2-sulfanylideneethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=S)CNC(=O)C1=CN=CC=C1C(F)(F)F TUXUVCWYZALXIE-UHFFFAOYSA-N 0.000 claims 1
NOHGVHNWHZMHJR-UHFFFAOYSA-N n-(piperidin-1-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCN1CCCCC1 NOHGVHNWHZMHJR-UHFFFAOYSA-N 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 60
239000002904 solvent Substances 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000009472 formulation Methods 0.000 description 20
239000000243 solution Substances 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
241000196324 Embryophyta Species 0.000 description 17
239000002585 base Substances 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000012360 testing method Methods 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
239000000575 pesticide Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241000721621 Myzus persicae Species 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000002917 insecticide Substances 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241001124076 Aphididae Species 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000011570 nicotinamide Substances 0.000 description 6
229960003966 nicotinamide Drugs 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
238000005507 spraying Methods 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
241000255925 Diptera Species 0.000 description 4
206010061217 Infestation Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000000642 acaricide Substances 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003905 agrochemical Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000005645 nematicide Substances 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 3
PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 3
WRXXBTBGBXYHSG-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC(Cl)=NC(Cl)=C1C#N WRXXBTBGBXYHSG-UHFFFAOYSA-N 0.000 description 3
KPMYDDLYJBPUEY-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=C(Cl)N=C(Cl)C=C1C(F)(F)F KPMYDDLYJBPUEY-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
XILYOLONIFWGMT-UHFFFAOYSA-N benzene;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC=C1 XILYOLONIFWGMT-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
239000012320 chlorinating reagent Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000000417 fungicide Substances 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
150000002903 organophosphorus compounds Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000002728 pyrethroid Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
241000894007 species Species 0.000 description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
230000009897 systematic effect Effects 0.000 description 3
LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 2
QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 2
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
VTIDQRMMPBLMGG-UHFFFAOYSA-N 1,4,2,3-dioxathiazolidin-5-one Chemical compound O=C1ONSO1 VTIDQRMMPBLMGG-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
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QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
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YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
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KAXZKCMZFQGCOH-UHFFFAOYSA-N ethyl 2-[[4-(trifluoromethyl)pyridine-3-carbonyl]amino]ethanimidate Chemical compound CCOC(=N)CNC(=O)C1=CN=CC=C1C(F)(F)F KAXZKCMZFQGCOH-UHFFFAOYSA-N 0.000 description 1
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ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 description 1
ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
239000000945 filler Substances 0.000 description 1
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UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
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DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 1
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125000004438 haloalkoxy group Chemical group 0.000 description 1
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QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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230000000366 juvenile effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
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ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
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FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
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GXQFNSNBDBARSW-UHFFFAOYSA-N n-[(propan-2-ylamino)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC(C)NCNC(=O)C1=CN=CC=C1C(F)(F)F GXQFNSNBDBARSW-UHFFFAOYSA-N 0.000 description 1
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QTNMPZJVQTWPCD-UHFFFAOYSA-N n-piperidin-1-yl-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NN1CCCCC1 QTNMPZJVQTWPCD-UHFFFAOYSA-N 0.000 description 1
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150000002894 organic compounds Chemical class 0.000 description 1
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239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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239000004848 polyfunctional curative Substances 0.000 description 1
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229920002635 polyurethane Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
235000008476 powdered milk Nutrition 0.000 description 1
QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
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238000001228 spectrum Methods 0.000 description 1
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101150035983 str1 gene Proteins 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000004552 water soluble powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000011845 white flour Nutrition 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/61—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

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

SK750-93A 1992-07-23 1993-07-15 Amidová zlúčenina a jej soli, spôsob jej prípravy a pesticídny prostriedok s jej obsahom SK281481B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP23880492		1992-07-23
JP5766893		1993-02-05
JP9642893		1993-03-17

Publications (2)

Publication Number	Publication Date
SK75093A3 SK75093A3 (en)	1994-06-08
SK281481B6 true SK281481B6 (sk)	2001-04-09

Family

ID=27296335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK750-93A SK281481B6 (sk)	1992-07-23	1993-07-15	Amidová zlúčenina a jej soli, spôsob jej prípravy a pesticídny prostriedok s jej obsahom

Country Status (23)

Country	Link
US (1)	US5360806A (da)
EP (1)	EP0580374B1 (da)
JP (1)	JP2994182B2 (da)
KR (1)	KR100282243B1 (da)
CN (1)	CN1044233C (da)
AT (1)	ATE132489T1 (da)
AU (1)	AU657056B2 (da)
BR (1)	BR9302960A (da)
CA (1)	CA2100011C (da)
CO (1)	CO4750587A1 (da)
CZ (1)	CZ286147B6 (da)
DE (1)	DE69301205T2 (da)
DK (1)	DK0580374T3 (da)
EG (1)	EG20154A (da)
ES (1)	ES2085118T3 (da)
GR (1)	GR3018953T3 (da)
HU (1)	HU214279B (da)
IL (1)	IL106340A (da)
MX (1)	MX9304425A (da)
NL (1)	NL350027I2 (da)
PL (1)	PL173611B1 (da)
SK (1)	SK281481B6 (da)
TW (1)	TW242554B (da)

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1993
- 1993-06-30 JP JP5214766A patent/JP2994182B2/ja not_active Expired - Lifetime
- 1993-07-06 TW TW082105377A patent/TW242554B/zh active
- 1993-07-07 CA CA002100011A patent/CA2100011C/en not_active Expired - Lifetime
- 1993-07-14 IL IL10634093A patent/IL106340A/en not_active IP Right Cessation
- 1993-07-15 SK SK750-93A patent/SK281481B6/sk active Protection Beyond IP Right Term
- 1993-07-16 DK DK93305622.8T patent/DK0580374T3/da active
- 1993-07-16 AT AT93305622T patent/ATE132489T1/de active
- 1993-07-16 ES ES93305622T patent/ES2085118T3/es not_active Expired - Lifetime
- 1993-07-16 EP EP93305622A patent/EP0580374B1/en not_active Expired - Lifetime
- 1993-07-16 DE DE69301205T patent/DE69301205T2/de not_active Expired - Lifetime
- 1993-07-21 EG EG45993A patent/EG20154A/xx active
- 1993-07-21 AU AU42106/93A patent/AU657056B2/en not_active Expired
- 1993-07-22 PL PL93299769A patent/PL173611B1/pl unknown
- 1993-07-22 BR BR9302960A patent/BR9302960A/pt not_active IP Right Cessation
- 1993-07-22 CO CO93397781A patent/CO4750587A1/es unknown
- 1993-07-22 KR KR1019930013885A patent/KR100282243B1/ko not_active Expired - Lifetime
- 1993-07-22 MX MX9304425A patent/MX9304425A/es unknown
- 1993-07-23 CZ CZ19931502A patent/CZ286147B6/cs not_active IP Right Cessation
- 1993-07-23 US US08/095,192 patent/US5360806A/en not_active Expired - Lifetime
- 1993-07-23 HU HU9302144A patent/HU214279B/hu active Protection Beyond IP Right Term
- 1993-07-23 CN CN93109092A patent/CN1044233C/zh not_active Expired - Lifetime
1996
- 1996-02-14 GR GR960400353T patent/GR3018953T3/el unknown
2006
- 2006-03-21 NL NL350027C patent/NL350027I2/nl unknown

Also Published As

Publication number	Publication date
KR100282243B1 (ko)	2001-02-15
IL106340A0 (en)	1993-11-15
HUT68334A (en)	1995-06-28
KR940005575A (ko)	1994-03-21
DE69301205T2 (de)	1996-09-05
SK75093A3 (en)	1994-06-08
EP0580374A1 (en)	1994-01-26
PL173611B1 (pl)	1998-04-30
ATE132489T1 (de)	1996-01-15
DE69301205D1 (de)	1996-02-15
CN1044233C (zh)	1999-07-21
TW242554B (da)	1995-03-11
CZ150293A3 (en)	1994-02-16
PL299769A1 (en)	1994-04-05
CA2100011C (en)	1998-02-03
NL350027I2 (nl)	2006-07-03
US5360806A (en)	1994-11-01
ES2085118T3 (es)	1996-05-16
GR3018953T3 (en)	1996-05-31
NL350027I1 (nl)	2006-06-01
CN1081670A (zh)	1994-02-09
EG20154A (en)	1997-07-31
HU214279B (hu)	1998-03-02
MX9304425A (es)	1994-02-28
JPH06321903A (ja)	1994-11-22
IL106340A (en)	1999-03-12
AU657056B2 (en)	1995-02-23
DK0580374T3 (da)	1996-05-20
HK1001896A1 (en)	1998-07-17
CA2100011A1 (en)	1994-01-24
HU9302144D0 (en)	1993-11-29
AU4210693A (en)	1994-02-03
CZ286147B6 (cs)	2000-01-12
BR9302960A (pt)	1994-02-16
EP0580374B1 (en)	1996-01-03
CO4750587A1 (es)	1999-03-31
JP2994182B2 (ja)	1999-12-27

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