CS208682B2 - Insecticide,acaricide and nematocide means and method of making its active agent - Google Patents

Insecticide,acaricide and nematocide means and method of making its active agent Download PDF

Info

Publication number: CS208682B2
Authority: CS; Czechoslovakia
Prior art keywords: oxo; oxime; thiazoline; dimethyl; methylcarbamoyl
Prior art date: 1978-11-09

Application number

CS797593A

Other languages

Czech (cs)

English (en)

Inventor

Paul Winternitz

Original Assignee

Hoffmann La Roche

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.)

1978-11-09

Filing date

1979-11-07

Publication date

1981-09-15

1979-11-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1981-09-15 Publication of CS208682B2 publication Critical patent/CS208682B2/cs

Links

230000000895 acaricidal effect Effects 0.000 title claims description 6
230000001069 nematicidal effect Effects 0.000 title claims description 6
239000013543 active substance Substances 0.000 title description 15
238000004519 manufacturing process Methods 0.000 title description 3
239000000642 acaricide Substances 0.000 title 1
239000002917 insecticide Substances 0.000 title 1
239000005645 nematicide Substances 0.000 title 1
-1 methylcarbamoyl Chemical group 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 45
150000002923 oximes Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
150000002513 isocyanates Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
AVFWBHLRUVGEBN-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)ON=C1SC(C)(C)C(C)=N1 AVFWBHLRUVGEBN-UHFFFAOYSA-N 0.000 claims description 3
BGDCVXREYPNFKP-UHFFFAOYSA-N [(4,5-diethyl-5-methyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCC1=NC(=NOC(=O)NC)SC1(C)CC BGDCVXREYPNFKP-UHFFFAOYSA-N 0.000 claims description 3
NMGNALCSSWDZAY-UHFFFAOYSA-N [(5,5-dimethyl-4-phenyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(C)C(C=2C=CC=CC=2)=N1 NMGNALCSSWDZAY-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
OGWBDBQGRWCQEM-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n-cyclobutylcarbamate Chemical compound S1C(C)(C)C(C)=NC1=NOC(=O)NC1CCC1 OGWBDBQGRWCQEM-UHFFFAOYSA-N 0.000 claims description 2
YANQNGCPZCNXEE-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n-cyclopropylcarbamate Chemical compound S1C(C)(C)C(C)=NC1=NOC(=O)NC1CC1 YANQNGCPZCNXEE-UHFFFAOYSA-N 0.000 claims description 2
LDUPDAYJQGBFJZ-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n-ethylcarbamate Chemical compound CCNC(=O)ON=C1SC(C)(C)C(C)=N1 LDUPDAYJQGBFJZ-UHFFFAOYSA-N 0.000 claims description 2
YUNFCBKRBPUQHV-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(C)C(C)=N1 YUNFCBKRBPUQHV-UHFFFAOYSA-N 0.000 claims description 2
MUCLWMWCWBJELH-UHFFFAOYSA-N [(4,5-dimethyl-5-pentyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCCCC1(C)SC(=NOC(=O)NC)N=C1C MUCLWMWCWBJELH-UHFFFAOYSA-N 0.000 claims description 2
ORMVGNHPPUGQIL-UHFFFAOYSA-N [(4-ethyl-5,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCC1=NC(=NOC(=O)NC)SC1(C)C ORMVGNHPPUGQIL-UHFFFAOYSA-N 0.000 claims description 2
MVNNZYFBJNHMRC-UHFFFAOYSA-N [(5,5-dimethyl-4-propan-2-yl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(C)C(C(C)C)=N1 MVNNZYFBJNHMRC-UHFFFAOYSA-N 0.000 claims description 2
ZKLYVBMHKGFKHE-UHFFFAOYSA-N [[4,5-dimethyl-5-(2-methylpropyl)-1,3-thiazol-2-ylidene]amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(CC(C)C)C(C)=N1 ZKLYVBMHKGFKHE-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
HSJUWINNRZXMTO-UHFFFAOYSA-N [(4,5,5-trimethyl-1,3-thiazol-2-ylidene)amino] n-propan-2-ylcarbamate Chemical compound CC(C)NC(=O)ON=C1SC(C)(C)C(C)=N1 HSJUWINNRZXMTO-UHFFFAOYSA-N 0.000 claims 1
LBBPSJVCAZDELG-UHFFFAOYSA-N [(4,5-dimethyl-5-propyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCC1(C)SC(=NOC(=O)NC)N=C1C LBBPSJVCAZDELG-UHFFFAOYSA-N 0.000 claims 1
KPBPGMGANQUCTE-UHFFFAOYSA-N [(4-butyl-5,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCCC1=NC(=NOC(=O)NC)SC1(C)C KPBPGMGANQUCTE-UHFFFAOYSA-N 0.000 claims 1
XGSSVQXZAQBWLB-UHFFFAOYSA-N [(4-cyclohexyl-5,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(C)C(C2CCCCC2)=N1 XGSSVQXZAQBWLB-UHFFFAOYSA-N 0.000 claims 1
FINQJZYVXUUCIX-UHFFFAOYSA-N [(5,5-dimethyl-4-propyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCC1=NC(=NOC(=O)NC)SC1(C)C FINQJZYVXUUCIX-UHFFFAOYSA-N 0.000 claims 1
PVLDMWSGSSFODQ-UHFFFAOYSA-N [(5-butyl-4,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCCC1(C)SC(=NOC(=O)NC)N=C1C PVLDMWSGSSFODQ-UHFFFAOYSA-N 0.000 claims 1
SBXIJAIALBPVTR-UHFFFAOYSA-N [(5-ethyl-4,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCC1(C)SC(=NOC(=O)NC)N=C1C SBXIJAIALBPVTR-UHFFFAOYSA-N 0.000 claims 1
BDXUKJCGKUGDDQ-UHFFFAOYSA-N [(5-ethyl-5-methyl-4-propyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCC1=NC(=NOC(=O)NC)SC1(C)CC BDXUKJCGKUGDDQ-UHFFFAOYSA-N 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
239000007858 starting material Substances 0.000 description 20
239000000243 solution Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000002904 solvent Substances 0.000 description 16
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
241000244206 Nematoda Species 0.000 description 9
WXDSOCYXOXOMDK-UHFFFAOYSA-N n-(4,5,5-trimethyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CC1=NC(=NO)SC1(C)C WXDSOCYXOXOMDK-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241000238876 Acari Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000258916 Leptinotarsa decemlineata Species 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
241000239290 Araneae Species 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
241000258937 Hemiptera Species 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
235000013601 eggs Nutrition 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000011533 pre-incubation Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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238000007796 conventional method Methods 0.000 description 3
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235000012239 silicon dioxide Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
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150000007513 acids Chemical class 0.000 description 2
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150000001412 amines Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
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238000010992 reflux Methods 0.000 description 2
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229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000005507 spraying Methods 0.000 description 2
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239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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XTEGVFVZDVNBPF-UHFFFAOYSA-N 1,5-naphthalene disulfonic acid Natural products C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 1
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FLYPZWDELZKIOY-UHFFFAOYSA-O 2-carboxyethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(=O)O)C1=CC=CC=C1 FLYPZWDELZKIOY-UHFFFAOYSA-O 0.000 description 1
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FUOVXAUWUNNHOJ-UHFFFAOYSA-N n-[4,5-dimethyl-5-(2-methylpropyl)-1,3-thiazol-2-ylidene]hydroxylamine Chemical compound CC(C)CC1(C)SC(=NO)N=C1C FUOVXAUWUNNHOJ-UHFFFAOYSA-N 0.000 description 1
WVWIITMSOAASBJ-UHFFFAOYSA-N n-[4,5-dimethyl-5-(3-methylpent-2-enyl)-1,3-thiazol-2-ylidene]hydroxylamine Chemical compound CCC(C)=CCC1(C)SC(=NO)N=C1C WVWIITMSOAASBJ-UHFFFAOYSA-N 0.000 description 1
PGZUJUTYIZKSJC-UHFFFAOYSA-N n-benzyl-4,4-dimethylcyclohexan-1-amine Chemical compound C1CC(C)(C)CCC1NCC1=CC=CC=C1 PGZUJUTYIZKSJC-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
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FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010453 quartz Substances 0.000 description 1
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150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
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239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
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125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
239000002435 venom Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
231100000611 venom Toxicity 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms

Landscapes

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

CS797593A 1978-11-09 1979-11-07 Insecticide,acaricide and nematocide means and method of making its active agent CS208682B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1153178		1978-11-09
CH772879		1979-08-24

Publications (1)

Publication Number	Publication Date
CS208682B2 true CS208682B2 (en)	1981-09-15

Family

ID=25702045

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS797593A CS208682B2 (en)	1978-11-09	1979-11-07	Insecticide,acaricide and nematocide means and method of making its active agent

Country Status (15)

Country	Link
US (1)	US4255436A (tr)
EP (1)	EP0011221B1 (tr)
AR (1)	AR224136A1 (tr)
AU (1)	AU529272B2 (tr)
BR (1)	BR7907182A (tr)
CA (1)	CA1126278A (tr)
CS (1)	CS208682B2 (tr)
DD (1)	DD147195A5 (tr)
DE (1)	DE2965046D1 (tr)
DK (1)	DK474179A (tr)
EG (1)	EG13808A (tr)
ES (1)	ES485806A1 (tr)
IL (1)	IL58619A (tr)
PL (1)	PL219513A1 (tr)
TR (1)	TR20531A (tr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0039520B1 (de) *	1980-05-07	1984-04-11	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Carbamoyloxime, Verfahren und Mittel zu deren Herstellung, Schädlingsbekämpfungsmittel, enthaltend solche Verbindungen, sowie Verwendung solcher Verbindungen als Schädlingsbekämpfungsmittel
US4514566A (en) *	1981-04-24	1985-04-30	Hoffmann-La Roche Inc.	5-Oxo-3-thiazoline oxime and 2-oxo-5,6-dihydro-2H-1,4-thiazine oxime derivatives
US4427687A (en)	1981-04-24	1984-01-24	Hoffmann-La Roche Inc.	Thiazoline carbamoyl-oximes
US4640927A (en) *	1984-03-30	1987-02-03	Uniroyal Chemical Company, Inc.	Substituted oxime carbamates
DE3905714A1 (de) *	1989-02-24	1990-09-06	Bayer Ag	Sulfonylimino-azinylheteroazole, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3875232A (en) *	1971-04-08	1975-04-01	Diamond Shamrock Corp	AC Ketoxime carbamates
GB1357771A (en) *	1971-05-07	1974-06-26	Ici Ltd	Carbamoyloxime compounds and compositions and processes for pre paring them
US3966953A (en) *	1972-12-29	1976-06-29	Union Carbide Corporation	2-(Carbamoyloximino)-4-thiazolidinone compounds as insecticidal, miticidal or nematocidal agents
US4315928A (en) *	1975-06-26	1982-02-16	Union Carbide Corporation	N-Aminosulfenyl carbamate compounds, compositions and use
US4181661A (en) *	1976-05-03	1980-01-01	Merck & Co., Inc.	Derivatives of 2-iminothiazolidines and thiazolines

1979
- 1979-09-28 CA CA336,601A patent/CA1126278A/en not_active Expired
- 1979-10-31 US US06/089,793 patent/US4255436A/en not_active Expired - Lifetime
- 1979-11-02 IL IL58619A patent/IL58619A/xx unknown
- 1979-11-05 AU AU52483/79A patent/AU529272B2/en not_active Expired - Fee Related
- 1979-11-06 EP EP79104345A patent/EP0011221B1/de not_active Expired
- 1979-11-06 DE DE7979104345T patent/DE2965046D1/de not_active Expired
- 1979-11-06 BR BR7907182A patent/BR7907182A/pt unknown
- 1979-11-07 CS CS797593A patent/CS208682B2/cs unknown
- 1979-11-07 EG EG673/79A patent/EG13808A/xx active
- 1979-11-07 AR AR278807A patent/AR224136A1/es active
- 1979-11-07 TR TR20531A patent/TR20531A/tr unknown
- 1979-11-08 DK DK474179A patent/DK474179A/da not_active Application Discontinuation
- 1979-11-08 ES ES485806A patent/ES485806A1/es not_active Expired
- 1979-11-08 DD DD79216772A patent/DD147195A5/de unknown
- 1979-11-09 PL PL21951379A patent/PL219513A1/xx unknown

Also Published As

Publication number	Publication date
DE2965046D1 (en)	1983-04-21
DD147195A5 (de)	1981-03-25
TR20531A (tr)	1981-10-21
AU529272B2 (en)	1983-06-02
BR7907182A (pt)	1980-08-05
US4255436A (en)	1981-03-10
AU5248379A (en)	1980-05-15
IL58619A0 (en)	1980-02-29
DK474179A (da)	1980-05-10
IL58619A (en)	1982-12-31
ES485806A1 (es)	1980-10-01
CA1126278A (en)	1982-06-22
PL219513A1 (tr)	1980-12-15
EP0011221A1 (de)	1980-05-28
EP0011221B1 (de)	1983-03-16
EG13808A (en)	1982-06-30
AR224136A1 (es)	1981-10-30

Publication	Publication Date	Title
JPH02209868A (ja)	1990-08-21	殺虫性シアノ化合物
PL85051B1 (tr)	1976-04-30
CS197296B2 (en)	1980-04-30	Insecticide and fungicide means
PL99856B1 (pl)	1978-08-31	Srodek owadobojczy,roztoczobojczy i grzybobojczy
CS214681B2 (en)	1982-05-28	Fungicide means
CS208682B2 (en)	1981-09-15	Insecticide,acaricide and nematocide means and method of making its active agent
US4725302A (en)	1988-02-16	Substituted phenylhydrazines and phenyloxadiazolinones and pesticidal usage thereof
WO1998042683A1 (en)	1998-10-01	Triazole compounds, process for the preparation thereof, and insecticides and miticides
CS214830B2 (en)	1982-06-25	Insecticide means and method of making the active substances
US3678075A (en)	1972-07-18	Carbamoyloximino-alkenyl-dithiolanes
EP0100528A2 (de)	1984-02-15	Neue (Di)-thiophosphor- und -phosphonsäure-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung im Pflanzenschutz
KR920002794B1 (ko)	1992-04-03	치환된 벤질사이클로알케닐우레아 유도체의 제조방법
US4450157A (en)	1984-05-22	Thiazoline derivatives
CS199286B2 (en)	1980-07-31	Fungicides,insecticides,acaricides,nematocides and herbicides and method of producing active compounds
CS236670B2 (en)	1985-05-15	Insecticide,akaricide and nematocide agent and manufacturing of its efficion substance
CS215060B2 (en)	1982-07-30	Fungicide means
US4215122A (en)	1980-07-29	4-Alkyl- and 4-allyl-mercapto-, -sulfinyl- and -sulfonyl-methyl-2-amino-6-N,N-dimethylcarbamoyloxy-pyrimidines, processes for producing them, compositions containing these pyrimidines, and the use thereof for controlling insect pests
KR860000766B1 (ko)	1986-06-23	치환페닐(티오노)카바메이트의 제조방법
US4427687A (en)	1984-01-24	Thiazoline carbamoyl-oximes
CN116265461B (zh)	2024-08-16	咪唑并吡啶硫酮类化合物及其制备方法与应用
GB1580711A (en)	1980-12-03	Pyrazolone derivatives and their use as pesticides
US4514566A (en)	1985-04-30	5-Oxo-3-thiazoline oxime and 2-oxo-5,6-dihydro-2H-1,4-thiazine oxime derivatives
DE3203656A1 (de)	1983-08-11	Neue 1,2,3-thiadiazolymethyl-(di)thiophosphate, -phosphonate und phosphoramidate, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung als pestizide sowie neue thiadiazole als zwischenstufen und verfahren zu deren herstellung
US4254136A (en)	1981-03-03	Phenolic esters of N-trialkylureidothio-N-methyl carbamic acids useful as insecticides
CA1151190A (en)	1983-08-02	N-(2-isobutyronitrilesulfenyl)-n-methyl carbamates, processes for producing them, and their use in combating insect pests