CA1041093A - Agent insecticides (nitromethylene),2-diazacycloalkanes,1,3 - Google Patents

Agent insecticides (nitromethylene),2-diazacycloalkanes,1,3

Info

Publication number: CA1041093A
Authority: CA; Canada
Prior art keywords: nitromethylene; derivative according; imidazolidine; carbon atoms; methyl
Prior art date: 1973-11-01
Legal status (The legal status 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 status listed.): Expired

Application number

CA209,936A

Other languages

English (en)

Other versions

CA209936S (en

Inventor

Charles H. Tieman

Steven A. Roman

Willy D. Kollmeyer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada 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.)

1973-11-01

Filing date

1974-09-24

Publication date

1978-10-24

1974-09-24 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1978-10-24 Application granted granted Critical

1978-10-24 Publication of CA1041093A publication Critical patent/CA1041093A/fr

Status Expired legal-status Critical Current

Links

241000238631 Hexapoda Species 0.000 title claims description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
-1 epoxyalkyl Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 7
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
AWPUGPLRCFPMGN-UHFFFAOYSA-N 2-[dibromo(nitro)methyl]-1-methyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C(Br)(Br)[N+]([O-])=O AWPUGPLRCFPMGN-UHFFFAOYSA-N 0.000 claims description 3
ZJRUHCYDSXYQOY-UHFFFAOYSA-N 1-methyl-2-(nitromethylidene)-1,3-diazepane Chemical compound CN1CCCCNC1=C[N+]([O-])=O ZJRUHCYDSXYQOY-UHFFFAOYSA-N 0.000 claims description 2
KCZLNVXIIPCLQE-UHFFFAOYSA-N 1-methyl-2-(nitromethylidene)imidazolidine Chemical compound CN1CCNC1=C[N+]([O-])=O KCZLNVXIIPCLQE-UHFFFAOYSA-N 0.000 claims description 2
IXWPODLEYISYAA-UHFFFAOYSA-N 2-(nitromethylidene)-1-prop-2-ynylimidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1CC#C IXWPODLEYISYAA-UHFFFAOYSA-N 0.000 claims description 2
KAIVLPUTBJRDAD-UHFFFAOYSA-N 2-[bromo(nitro)methylidene]-1-methylimidazolidine Chemical compound CN1CCNC1=C(Br)[N+]([O-])=O KAIVLPUTBJRDAD-UHFFFAOYSA-N 0.000 claims description 2
241000607479 Yersinia pestis Species 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
CKCZUVCFXDRIQD-UHFFFAOYSA-N 1-(2-chloroprop-2-enyl)-2-(nitromethylidene)imidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1CC(Cl)=C CKCZUVCFXDRIQD-UHFFFAOYSA-N 0.000 claims 1
NWTAFJPVDKNLOZ-UHFFFAOYSA-N 1-ethyl-2-(nitromethylidene)imidazolidine Chemical compound CCN1CCNC1=C[N+]([O-])=O NWTAFJPVDKNLOZ-UHFFFAOYSA-N 0.000 claims 1
ZSQOWZCJWILHLO-UHFFFAOYSA-N 1-methyl-2-(nitromethylidene)-1,3-diazinane Chemical compound CN1CCCNC1=C[N+]([O-])=O ZSQOWZCJWILHLO-UHFFFAOYSA-N 0.000 claims 1
ALZPTDSNSHKIJR-UHFFFAOYSA-N 2-(nitromethylidene)-1-prop-2-enyl-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1CC=C ALZPTDSNSHKIJR-UHFFFAOYSA-N 0.000 claims 1
BWJPKQVFWNVTLY-UHFFFAOYSA-N 2-(nitromethylidene)-1-prop-2-enylimidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1CC=C BWJPKQVFWNVTLY-UHFFFAOYSA-N 0.000 claims 1
QEKKMCBDCNTMEE-UHFFFAOYSA-N 2-(nitromethylidene)-1-prop-2-ynyl-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1CC#C QEKKMCBDCNTMEE-UHFFFAOYSA-N 0.000 claims 1
GSUYFUSILQIUQV-UHFFFAOYSA-N 2-(nitromethylidene)-1-propylimidazolidine Chemical compound CCCN1CCNC1=C[N+]([O-])=O GSUYFUSILQIUQV-UHFFFAOYSA-N 0.000 claims 1
FENMETGERHGZHQ-UHFFFAOYSA-N 2-[dibromo(nitro)methyl]-1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1C(Br)(Br)[N+]([O-])=O FENMETGERHGZHQ-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 30
239000002917 insecticide Substances 0.000 abstract description 6
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
150000002431 hydrogen Chemical group 0.000 abstract 2
125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000002904 solvent Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
150000004985 diamines Chemical class 0.000 description 8
231100000167 toxic agent Toxicity 0.000 description 7
239000003440 toxic substance Substances 0.000 description 7
241000255967 Helicoverpa zea Species 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
241000894007 species Species 0.000 description 4
OHXNZFJZRFHBLX-UHFFFAOYSA-N 2-(nitromethylidene)imidazolidine Chemical compound [O-][N+](=O)C=C1NCCN1 OHXNZFJZRFHBLX-UHFFFAOYSA-N 0.000 description 3
241000218475 Agrotis segetum Species 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
239000002253 acid Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical compound N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 3
UOORRWUZONOOLO-UHFFFAOYSA-N 1,3-dichloropropene Chemical compound ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 2
HXXJFHPDGDGEIG-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-diazepane Chemical compound [O-][N+](=O)C=C1NCCCCN1 HXXJFHPDGDGEIG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000253994 Acyrthosiphon pisum Species 0.000 description 2
241000239290 Araneae Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
241001147381 Helicoverpa armigera Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000254152 Sitophilus oryzae Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000255993 Trichoplusia ni Species 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
BKOLIJBSENFKNE-UHFFFAOYSA-N 1,1,2-trichloro-2-nitroethene Chemical group [O-][N+](=O)C(Cl)=C(Cl)Cl BKOLIJBSENFKNE-UHFFFAOYSA-N 0.000 description 1
YQOUONFYROBORG-UHFFFAOYSA-N 1-(2-methoxyethyl)-2-(nitromethylidene)imidazolidine Chemical compound COCCN1CCNC1=C[N+]([O-])=O YQOUONFYROBORG-UHFFFAOYSA-N 0.000 description 1
LFKVFDBOPAWOHN-UHFFFAOYSA-N 1-chloro-2-(nitromethylidene)imidazolidine Chemical compound ClN1C(NCC1)=C[N+](=O)[O-] LFKVFDBOPAWOHN-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
FCDVAWSOIPXPJY-UHFFFAOYSA-N 2-(nitromethylidene)imidazolidin-1-amine Chemical compound NN1CCNC1=C[N+]([O-])=O FCDVAWSOIPXPJY-UHFFFAOYSA-N 0.000 description 1
AZXZBPZPSMNJBI-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-1-methylimidazolidine Chemical compound CN1CCNC1=C(Cl)[N+]([O-])=O AZXZBPZPSMNJBI-UHFFFAOYSA-N 0.000 description 1
FOMYXNXQHHHHGQ-UHFFFAOYSA-N 4-methyl-2-(nitromethylidene)imidazolidine Chemical compound CC1CNC(=C[N+]([O-])=O)N1 FOMYXNXQHHHHGQ-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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101100001675 Emericella variicolor andJ gene Proteins 0.000 description 1
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
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IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
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ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
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MPVXINJRXRIDDB-VCDGYCQFSA-N dodecanoic acid;(2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol Polymers OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCC(O)=O MPVXINJRXRIDDB-VCDGYCQFSA-N 0.000 description 1
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235000019341 magnesium sulphate Nutrition 0.000 description 1
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KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
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AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 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
239000003016 pheromone Substances 0.000 description 1
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JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

CA209,936A 1973-11-01 1974-09-24 Agent insecticides (nitromethylene),2-diazacycloalkanes,1,3 Expired CA1041093A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US41237373A	1973-11-01	1973-11-01

Publications (1)

Publication Number	Publication Date
CA1041093A true CA1041093A (fr)	1978-10-24

Family

ID=23632730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA209,936A Expired CA1041093A (fr)	1973-11-01	1974-09-24	Agent insecticides (nitromethylene),2-diazacycloalkanes,1,3

Country Status (17)

Country	Link
JP (1)	JPS5838402B2 (fr)
BE (1)	BE821282A (fr)
BR (1)	BR7409077D0 (fr)
CA (1)	CA1041093A (fr)
CH (1)	CH611127A5 (fr)
DD (1)	DD115420A5 (fr)
DE (1)	DE2445421C2 (fr)
EG (1)	EG11523A (fr)
FR (1)	FR2249880B1 (fr)
GB (1)	GB1483633A (fr)
HU (1)	HU171829B (fr)
IL (1)	IL45966A (fr)
IT (1)	IT1046795B (fr)
NL (1)	NL179106C (fr)
OA (1)	OA04952A (fr)
PL (1)	PL93656B1 (fr)
TR (1)	TR18285A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0629256B2 (ja) *	1983-10-06	1994-04-20	日本バイエルアグロケム株式会社	ニトロメチレン−テトラヒドロピリミジン誘導体，その製法及び殺虫，殺ダニ，殺センチユウ剤
WO1991017659A1 (fr) *	1990-05-17	1991-11-28	E.I. Du Pont De Nemours And Company	Nitroethyelenes et nitroguanidines arthropodicides
JPH05310650A (ja) *	1991-08-22	1993-11-22	Nippon Soda Co Ltd	新規なアミン誘導体、その製造方法及び殺虫剤
EP0636122A1 (fr) *	1992-04-13	1995-02-01	E.I. Du Pont De Nemours And Company	Nitroguanidines et nitroethylenes arthropodicides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE798930A (fr) *	1972-05-04	1973-10-30	Shell Int Research	2-(nitromethylene)-piperidines et leur application comme insecticides

1974
- 1974-09-23 DE DE2445421A patent/DE2445421C2/de not_active Expired
- 1974-09-24 CA CA209,936A patent/CA1041093A/fr not_active Expired
- 1974-10-13 EG EG461/74A patent/EG11523A/xx active
- 1974-10-21 BE BE1006240A patent/BE821282A/xx not_active IP Right Cessation
- 1974-10-30 JP JP49124522A patent/JPS5838402B2/ja not_active Expired
- 1974-10-30 PL PL1974175255A patent/PL93656B1/pl unknown
- 1974-10-30 HU HU74SE00001749A patent/HU171829B/hu not_active IP Right Cessation
- 1974-10-30 CH CH1453374A patent/CH611127A5/xx not_active IP Right Cessation
- 1974-10-30 IT IT28993/74A patent/IT1046795B/it active
- 1974-10-30 GB GB46952/74A patent/GB1483633A/en not_active Expired
- 1974-10-30 IL IL45966A patent/IL45966A/xx unknown
- 1974-10-30 BR BR9077/74A patent/BR7409077D0/pt unknown
- 1974-10-30 FR FR7436297A patent/FR2249880B1/fr not_active Expired
- 1974-10-30 NL NLAANVRAGE7414165,A patent/NL179106C/xx not_active IP Right Cessation
- 1974-10-31 DD DD182071A patent/DD115420A5/xx unknown
- 1974-10-31 TR TR18285A patent/TR18285A/xx unknown
- 1974-12-02 OA OA55353A patent/OA04952A/fr unknown

Also Published As

Publication number	Publication date
AU7486774A (en)	1976-05-06
DE2445421A1 (de)	1975-05-07
DE2445421C2 (de)	1985-07-11
JPS5071676A (fr)	1975-06-13
DD115420A5 (fr)	1975-10-05
BR7409077D0 (pt)	1975-08-26
IL45966A (en)	1978-04-30
IL45966A0 (en)	1974-12-31
JPS5838402B2 (ja)	1983-08-23
IT1046795B (it)	1980-07-31
OA04952A (fr)	1980-10-31
CH611127A5 (en)	1979-05-31
BE821282A (nl)	1975-04-21
NL179106C (nl)	1986-07-16
FR2249880A1 (fr)	1975-05-30
GB1483633A (en)	1977-08-24
EG11523A (en)	1977-08-15
NL7414165A (nl)	1975-05-06
TR18285A (tr)	1976-11-22
PL93656B1 (fr)	1977-06-30
HU171829B (hu)	1978-03-28
FR2249880B1 (fr)	1976-10-22
NL179106B (nl)	1986-02-17

Publication	Publication Date	Title
US3948934A (en)	1976-04-06	2-(Nitromethylene)-1,3-diazacycloalkane insect control agents
IL44710A (en)	1977-12-30	1-phenyl-2-azolyl-formamidines their preparation and their use as herbicides
US3867384A (en)	1975-02-18	2-Amino-4(3H)-quinazolinones
CA1041093A (fr)	1978-10-24	Agent insecticides (nitromethylene),2-diazacycloalkanes,1,3
DE2263878A1 (de)	1973-07-05	Verfahren zur herstellung heterocyklischer verbindungen
US3969354A (en)	1976-07-13	2-(Nitromethylene)-hexahydropyrimidines
US4002765A (en)	1977-01-11	2-(Nitromethylene)-1,3-diazacycloalkane insect control agents
US3777024A (en)	1973-12-04	Synergistically activated biocidal compositions
US4297496A (en)	1981-10-27	Nitrimine derivatives
US3971774A (en)	1976-07-27	2-(Nitromethylene)-1,3-diazepines
US3962233A (en)	1976-06-08	2-(halonitro(organooxycarbonyl)methyl)-5,6-dihydro-4h-1,3-thiazines
DE1811409A1 (de)	1970-06-18	Mittel zur Bekaempfung von Insekten,Milben,Hasenartigen und Nagetieren
GB2073172A (en)	1981-10-14	Pesticidal Pyrazole Derivatives
US4237168A (en)	1980-12-02	N-(4-Chloro-2-methylphenyl)-N-hydroxy methanimidamide and its pesticidal use
US4160037A (en)	1979-07-03	Compounds, compositions and methods of combatting pest employing thioureas
EP0003081B1 (fr)	1981-12-30	Carbothioamides de thiazolidine, leur préparation, leurs compositions et leur application comme insecticides
US4006156A (en)	1977-02-01	3-Alkyl-2-(nitromethylene) thiazolidine
EP0117577B1 (fr)	1986-10-08	Dérivé nitrométhylénique pesticide
GB1603122A (en)	1981-11-18	Pesticidal sulphilimine derivatives
US4029791A (en)	1977-06-14	N-(Arylsulfonyl)-2-nitro-2-(1-methyl-2-(1,3-diazacycloalkylidene)acetamides
HU176427B (en)	1981-02-28	Pesticide compositions of thioamide base and process for producing the active agent
US3996372A (en)	1976-12-07	Insecticidal 1-acyl-3-substituted-2-(nitro(phenylthio)-methylene)imidazolidines
US3729485A (en)	1973-04-24	N-haloalkenylcycloamidines
US4034091A (en)	1977-07-05	N-(Arylsulfonyl)-2-nitro-2-(tetrahydro-2H-1,3-thiazin-2-ylidene)acetamides
US3206357A (en)	1965-09-14	Aminoaryltriazene pesticide