LT3209B - Amine derivatives - Google Patents

Amine derivatives Download PDF

Info

Publication number: LT3209B
Authority: LT; Lithuania
Prior art keywords: optionally substituted; formula; discretion; substituted; compound
Prior art date: 1989-10-06

Application number

LTIP342A

Other languages

English (en)

Lithuanian (lt)

Inventor

Keiichi Ishimitsu

Junji Suzuki

Haruhito Ohishi

Tomio Yamada

Renpei Hatano

Nobuo Takakusa

Jun Mitsui

Original Assignee

Nippon Soda Co

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.)

1989-10-06

Filing date

1993-02-13

Publication date

1995-03-27

1993-02-13 Application filed by Nippon Soda Co filed Critical Nippon Soda Co

1994-09-25 Publication of LTIP342A publication Critical patent/LTIP342A/xx

1995-03-27 Publication of LT3209B publication Critical patent/LT3209B/lt

Links

150000001412 amines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 62
-1 thiocarbamoyl Chemical group 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
230000000749 insecticidal effect Effects 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000003107 substituted aryl group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 claims 2
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000006396 nitration reaction Methods 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
125000005412 pyrazyl group Chemical group 0.000 claims 1
125000005495 pyridazyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
239000002917 insecticide Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
230000000052 comparative effect Effects 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
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235000007164 Oryza sativa Nutrition 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
235000009566 rice Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
230000000895 acaricidal effect Effects 0.000 description 4
239000000642 acaricide Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
101150065749 Churc1 gene Proteins 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000005949 Malathion Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229960000453 malathion Drugs 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000008096 xylene Substances 0.000 description 3
XPARFBOWIYMLMY-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanamine Chemical compound NCC1=CC=C(Cl)N=C1 XPARFBOWIYMLMY-UHFFFAOYSA-N 0.000 description 2
XALCOJXGWJXWBL-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-n-methylmethanamine Chemical compound CNCC1=CC=C(Cl)N=C1 XALCOJXGWJXWBL-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000931705 Cicada Species 0.000 description 2
241000592295 Cycadophyta Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241000255777 Lepidoptera Species 0.000 description 2
239000005916 Methomyl Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000000073 carbamate insecticide Substances 0.000 description 2
229960005286 carbaryl Drugs 0.000 description 2
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
235000021186 dishes Nutrition 0.000 description 2
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 2
230000000802 nitrating effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
239000010453 quartz Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
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239000012312 sodium hydride Substances 0.000 description 2
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239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
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125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
WGMHMVLZFAJNOT-UHFFFAOYSA-N 1-ethoxyethylideneazanium;chloride Chemical compound [Cl-].CCOC(C)=[NH2+] WGMHMVLZFAJNOT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
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FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
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WBXGFIGGYOXVMM-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-n-methyl-n'-nitroethanimidamide Chemical compound [O-][N+](=O)N=C(C)N(C)CC1=CC=C(Cl)N=C1 WBXGFIGGYOXVMM-UHFFFAOYSA-N 0.000 description 1
XVUORZBRKVSQMK-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-n-methylethanimidamide;hydrochloride Chemical compound Cl.CC(=N)N(C)CC1=CC=C(Cl)N=C1 XVUORZBRKVSQMK-UHFFFAOYSA-N 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
HPJZKYHLFXCFNU-UHFFFAOYSA-N n-cyano-n-methylethanimidamide Chemical compound N#CN(C)C(C)=N HPJZKYHLFXCFNU-UHFFFAOYSA-N 0.000 description 1
125000005461 organic phosphorous group Chemical group 0.000 description 1
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
229950005488 proclonol Drugs 0.000 description 1
WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-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
229910052903 pyrophyllite Inorganic materials 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-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
229960002447 thiram Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-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
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

LTIP342A 1989-10-06 1993-02-13 Amine derivatives LT3209B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP25996689		1989-10-06

Publications (2)

Publication Number	Publication Date
LTIP342A LTIP342A (en)	1994-09-25
LT3209B true LT3209B (en)	1995-03-27

Family

ID=17341404

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP342A LT3209B (en)	1989-10-06	1993-02-13	Amine derivatives

Country Status (4)

Country	Link
HU (1)	HU220083B (ru)
LT (1)	LT3209B (ru)
RU (1)	RU2038352C1 (ru)
ZA (1)	ZA907775B (ru)

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IL124128A (en) *	1998-03-02	2003-09-17	Yair Ben Ziony	Composition comprising a benzoylphenylurea for treatment of topical fungal infection
RU2185813C1 (ru) *	2001-02-26	2002-07-27	Всероссийский научно-исследовательский институт ветеринарной санитарии, гигиены и экологии	Инсектицидный состав
RU2329798C1 (ru) *	2007-02-09	2008-07-27	Общество с ограниченной ответственностью "Научно-внедренческий центр Агроветзащита"	Способ лечения и профилактики арахно-энтомозов млекопитающих животных и лекарственное средство для лечения и профилактики арахно-энтомозов млекопитающих животных
JP5417814B2 (ja) *	2008-11-25	2014-02-19	住友化学株式会社	植物病害防除用組成物及び植物病害の防除方法

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US4918088A (en)	1987-07-20	1990-04-17	Ciba-Geigy Corporation	Pest control

1990
- 1990-09-28 ZA ZA907775A patent/ZA907775B/xx unknown
- 1990-10-04 HU HU9802249A patent/HU220083B/hu unknown
1991
- 1991-06-05 RU SU914895590A patent/RU2038352C1/ru active
1993
- 1993-02-13 LT LTIP342A patent/LT3209B/lt not_active IP Right Cessation

Patent Citations (1)

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Publication number	Priority date	Publication date	Assignee	Title
US4918088A (en)	1987-07-20	1990-04-17	Ciba-Geigy Corporation	Pest control

Also Published As

Publication number	Publication date
RU2038352C1 (ru)	1995-06-27
LTIP342A (en)	1994-09-25
ZA907775B (en)	1991-07-31
HU220083B (hu)	2001-10-28
HU9802249D0 (en)	1998-12-28

Publication	Publication Date	Title
JP2926954B2 (ja)	1999-07-28	アミン誘導体、その製造方法及び殺虫剤
DE69029334T2 (de)	1997-04-30	Verfahren zur Herstellung von Alkoxyiminoacetamid-Derivaten und ein Zwischenproduckt dafür
DE3886467T2 (de)	1994-06-01	Alpha-ungesättigte Amine, ihre Herstellung und Verwendung.
DE69301205T2 (de)	1996-09-05	Pyridin-Amide und ihre Salze, Verfahren zur ihrer Herstellung und pestizide Zusammensetzungen davon
DE69119301T2 (de)	1996-10-17	Hydrazincarboxamidderivate, Verfahren für ihre Herstellung und ihre Verwendung
DE69311257T2 (de)	1998-01-15	Methoxyiminoessigsäure-Derivate und Fungizide für Landwirtschaft und Gartenbau, die diese als aktive Bestandteile enthalten
EP0212600B1 (de)	1991-11-27	Neue Nitromethylen-Derivate
JPS6310762A (ja)	1988-01-18	新規アルキレンジアミン類
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JP2943246B2 (ja)	1999-08-30	ニトロエチレン誘導体、その製造方法及び殺虫剤
DE2949342C2 (ru)	1989-08-31
KR890000367B1 (ko)	1989-03-14	살균성n-페닐카르바메이트의 제조방법
US4168319A (en)	1979-09-18	N-alkynyl-2-(substituted phenoxy) butyramides and their use as mildewicides
LT3209B (en)	1995-03-27	Amine derivatives
US5556885A (en)	1996-09-17	N-aryl- and N-heteroarylhydrazones of substituted thioacids and the s-oxides thereof as insecticidal and acaricidal agents
DE69010949T2 (de)	1994-11-24	Heterocyclische Verbindung, ihre Herstellung und Verwendung.
DE3872634T2 (de)	1992-12-03	Thiadiazine, verfahren zu deren herstellung und insektizide.
EP0392286B1 (de)	1993-11-18	3-Cyano-4-phenyl-pyrrol-Derivate
US4900354A (en)	1990-02-13	(Quinolinyl and quinoxalinyloxy)phenoxy alkenols and their use as post emergent herbicides
EP0003430B1 (en)	1982-01-06	Novel 2,6-dinitrobenzenamines, their preparation, composition containing them and their use as fungicides
DE69002792T2 (de)	1993-12-09	Crotonsäureamidderivate und sie enthaltende Insektizide.
US4976772A (en)	1990-12-11	4-((aryloxy)phenoxy)alkenol as intermediates and herbicides
JPS601315B2 (ja)	1985-01-14	イミダゾール誘導体、その製造方法及び農園芸用殺菌剤
DE3318648A1 (de)	1984-11-22	Substituierte tetrahydrothiopyran-3,5-dion-4-carboxamide
JPS61275271A (ja)	1986-12-05	１，２，４−オキサ（チア）ジアゾリン誘導体、その製造方法，殺虫剤及び農園芸用殺菌剤

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