CA1090250A - Pesticidally active compounds and their manufacture and use - Google Patents
Pesticidally active compounds and their manufacture and useInfo
- Publication number
- CA1090250A CA1090250A CA271,480A CA271480A CA1090250A CA 1090250 A CA1090250 A CA 1090250A CA 271480 A CA271480 A CA 271480A CA 1090250 A CA1090250 A CA 1090250A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compounds
- propynylamine
- general formula
- propynyl
- Prior art date
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 21
- 230000000361 pesticidal effect Effects 0.000 claims description 11
- 241000196324 Embryophyta Species 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims description 3
- 240000003259 Brassica oleracea var. botrytis Species 0.000 claims description 3
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- MHSYOEXUHOXGIY-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine Chemical compound C#CCN(C)CC1=CC=CC=C1Cl MHSYOEXUHOXGIY-UHFFFAOYSA-N 0.000 claims description 3
- BOVOUAAQVSTIKY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine Chemical compound C#CCN(C)CC1=CC=C(Cl)C=C1 BOVOUAAQVSTIKY-UHFFFAOYSA-N 0.000 claims description 3
- IVPRWAZFNPWWNW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine;hydrochloride Chemical compound Cl.C#CCN(C)CC1=CC=C(Cl)C=C1 IVPRWAZFNPWWNW-UHFFFAOYSA-N 0.000 claims description 3
- 230000002633 protecting effect Effects 0.000 claims description 3
- IPHOFQCLSFNFNX-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl-methyl-prop-2-ynylazanium chloride Chemical compound [Cl-].ClC=1C=C(C[NH+](CC#C)C)C=CC1Cl IPHOFQCLSFNFNX-UHFFFAOYSA-N 0.000 claims description 2
- HKCQJPAIGYTAPX-UHFFFAOYSA-N (3-methoxyphenyl)methyl-methyl-prop-2-ynylazanium chloride Chemical compound [Cl-].COC=1C=C(C[NH+](CC#C)C)C=CC1 HKCQJPAIGYTAPX-UHFFFAOYSA-N 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
- 240000007124 Brassica oleracea Species 0.000 claims description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 240000003768 Solanum lycopersicum Species 0.000 claims description 2
- 235000021536 Sugar beet Nutrition 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 235000005489 dwarf bean Nutrition 0.000 claims description 2
- 150000003840 hydrochlorides Chemical group 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- SEYXQIZJSTWOLR-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine Chemical compound C#CCN(C)CC1=CC=CC(Cl)=C1 SEYXQIZJSTWOLR-UHFFFAOYSA-N 0.000 claims description 2
- BUGSWGUOTWXJQG-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine;hydrochloride Chemical compound Cl.C#CCN(C)CC1=CC=CC(Cl)=C1 BUGSWGUOTWXJQG-UHFFFAOYSA-N 0.000 claims description 2
- UUJMAYTYTOVJRK-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-n-methylprop-2-yn-1-amine Chemical compound COC1=CC=CC(CN(C)CC#C)=C1 UUJMAYTYTOVJRK-UHFFFAOYSA-N 0.000 claims description 2
- BCXCABRDBBWWGY-UHFFFAOYSA-N n-benzyl-n-methylprop-2-yn-1-amine;hydrochloride Chemical compound Cl.C#CCN(C)CC1=CC=CC=C1 BCXCABRDBBWWGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- FEEKWCTWUPMUBX-UHFFFAOYSA-N (2,4-dichlorophenyl)methyl-methyl-prop-2-ynylazanium chloride Chemical compound [Cl-].ClC1=C(C[NH+](CC#C)C)C=CC(=C1)Cl FEEKWCTWUPMUBX-UHFFFAOYSA-N 0.000 claims 1
- UUKAIKMRUWNTOP-UHFFFAOYSA-N N-[(2,4-dichlorophenyl)methyl]-N-methylprop-2-yn-1-amine Chemical compound ClC1=C(CN(C)CC#C)C=CC(=C1)Cl UUKAIKMRUWNTOP-UHFFFAOYSA-N 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- ODDKTLPZJHMKMI-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-n-methylprop-2-yn-1-amine;hydrochloride Chemical compound [Cl-].C#CC[NH+](C)CC1=CC=CC=C1Cl ODDKTLPZJHMKMI-UHFFFAOYSA-N 0.000 claims 1
- FUXVQBGOEGOXFZ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-n-methylprop-2-yn-1-amine Chemical compound C#CCN(C)CC1=CC=C(Cl)C(Cl)=C1 FUXVQBGOEGOXFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- -1 carboxylic acid nitriles Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical class NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- AELCINSCMGFISI-DTWKUNHWSA-N (1R,2S)-tranylcypromine Chemical compound N[C@@H]1C[C@H]1C1=CC=CC=C1 AELCINSCMGFISI-DTWKUNHWSA-N 0.000 description 2
- BTHVHSMCHJCPFU-OULXEKPRSA-N (1r,2s)-2-phenylcyclopropan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.N[C@@H]1C[C@H]1C1=CC=CC=C1 BTHVHSMCHJCPFU-OULXEKPRSA-N 0.000 description 2
- 241001606185 Ascia monuste Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000000047 Gossypium barbadense Species 0.000 description 2
- 235000009429 Gossypium barbadense Nutrition 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LMBUJNXYGGNSAH-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=C(Cl)C=C1 LMBUJNXYGGNSAH-UHFFFAOYSA-N 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- ZQTQPYJGMWHXMO-UHFFFAOYSA-N OOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOO ZQTQPYJGMWHXMO-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 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 1
- 239000006028 limestone Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YPDVTKJXVHYWFY-UHFFFAOYSA-N phosphoric acid;n'-propan-2-ylpyridine-4-carbohydrazide Chemical compound OP(O)(O)=O.CC(C)NNC(=O)C1=CC=NC=C1 YPDVTKJXVHYWFY-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RTWCHRMHGXBETA-UHFFFAOYSA-N prop-1-yn-1-amine Chemical compound CC#CN RTWCHRMHGXBETA-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2609280.8 | 1976-03-04 | ||
| DE19762609280 DE2609280A1 (de) | 1976-03-04 | 1976-03-04 | Schaedlingsbekaempfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090250A true CA1090250A (en) | 1980-11-25 |
Family
ID=5971660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA271,480A Expired CA1090250A (en) | 1976-03-04 | 1977-02-10 | Pesticidally active compounds and their manufacture and use |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS52108022A (cs) |
| AU (1) | AU508246B2 (cs) |
| BE (1) | BE852088A (cs) |
| CA (1) | CA1090250A (cs) |
| CS (1) | CS193084B2 (cs) |
| DD (1) | DD129611A5 (cs) |
| DE (1) | DE2609280A1 (cs) |
| DK (1) | DK50977A (cs) |
| FR (1) | FR2342661A1 (cs) |
| GB (1) | GB1578852A (cs) |
| HU (1) | HU177907B (cs) |
| IE (1) | IE45599B1 (cs) |
| IL (1) | IL51463A (cs) |
| IT (1) | IT1143638B (cs) |
| LU (1) | LU76644A1 (cs) |
| NL (1) | NL7701575A (cs) |
| SU (1) | SU656462A3 (cs) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3582060D1 (de) * | 1984-11-22 | 1991-04-11 | Sandoz Ag | Homopropargylamine. |
| US5030625A (en) * | 1984-11-22 | 1991-07-09 | Sandoz Ltd. | Anti-fungal homopropargylamine compounds |
| US4933413A (en) * | 1989-04-10 | 1990-06-12 | Dow Corning Corporation | Process for synthesis of acylamino organosilicon compounds |
| ES2354993T3 (es) * | 2007-09-07 | 2011-03-21 | Cutech S.R.L. | Composiciones que comprenden pargilina . |
| US9113347B2 (en) | 2012-12-05 | 2015-08-18 | At&T Intellectual Property I, Lp | Backhaul link for distributed antenna system |
| US9768833B2 (en) | 2014-09-15 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for sensing a condition in a transmission medium of electromagnetic waves |
| US9762289B2 (en) | 2014-10-14 | 2017-09-12 | At&T Intellectual Property I, L.P. | Method and apparatus for transmitting or receiving signals in a transportation system |
| US9769020B2 (en) | 2014-10-21 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for responding to events affecting communications in a communication network |
| US9780834B2 (en) | 2014-10-21 | 2017-10-03 | At&T Intellectual Property I, L.P. | Method and apparatus for transmitting electromagnetic waves |
| US9312919B1 (en) | 2014-10-21 | 2016-04-12 | At&T Intellectual Property I, Lp | Transmission device with impairment compensation and methods for use therewith |
| US9544006B2 (en) | 2014-11-20 | 2017-01-10 | At&T Intellectual Property I, L.P. | Transmission device with mode division multiplexing and methods for use therewith |
| US9742462B2 (en) | 2014-12-04 | 2017-08-22 | At&T Intellectual Property I, L.P. | Transmission medium and communication interfaces and methods for use therewith |
| US9680670B2 (en) | 2014-11-20 | 2017-06-13 | At&T Intellectual Property I, L.P. | Transmission device with channel equalization and control and methods for use therewith |
| US10650940B2 (en) | 2015-05-15 | 2020-05-12 | At&T Intellectual Property I, L.P. | Transmission medium having a conductive material and methods for use therewith |
| US10812174B2 (en) | 2015-06-03 | 2020-10-20 | At&T Intellectual Property I, L.P. | Client node device and methods for use therewith |
| US9509415B1 (en) | 2015-06-25 | 2016-11-29 | At&T Intellectual Property I, L.P. | Methods and apparatus for inducing a fundamental wave mode on a transmission medium |
| US9722318B2 (en) | 2015-07-14 | 2017-08-01 | At&T Intellectual Property I, L.P. | Method and apparatus for coupling an antenna to a device |
| US10784670B2 (en) | 2015-07-23 | 2020-09-22 | At&T Intellectual Property I, L.P. | Antenna support for aligning an antenna |
| US9735833B2 (en) | 2015-07-31 | 2017-08-15 | At&T Intellectual Property I, L.P. | Method and apparatus for communications management in a neighborhood network |
| US9769128B2 (en) | 2015-09-28 | 2017-09-19 | At&T Intellectual Property I, L.P. | Method and apparatus for encryption of communications over a network |
| US9729197B2 (en) | 2015-10-01 | 2017-08-08 | At&T Intellectual Property I, L.P. | Method and apparatus for communicating network management traffic over a network |
| US10665942B2 (en) | 2015-10-16 | 2020-05-26 | At&T Intellectual Property I, L.P. | Method and apparatus for adjusting wireless communications |
| US11032819B2 (en) | 2016-09-15 | 2021-06-08 | At&T Intellectual Property I, L.P. | Method and apparatus for use with a radio distributed antenna system having a control channel reference signal |
| US10811767B2 (en) | 2016-10-21 | 2020-10-20 | At&T Intellectual Property I, L.P. | System and dielectric antenna with convex dielectric radome |
| US10755542B2 (en) | 2016-12-06 | 2020-08-25 | At&T Intellectual Property I, L.P. | Method and apparatus for surveillance via guided wave communication |
| US10694379B2 (en) | 2016-12-06 | 2020-06-23 | At&T Intellectual Property I, L.P. | Waveguide system with device-based authentication and methods for use therewith |
| US10727599B2 (en) | 2016-12-06 | 2020-07-28 | At&T Intellectual Property I, L.P. | Launcher with slot antenna and methods for use therewith |
| US10819035B2 (en) | 2016-12-06 | 2020-10-27 | At&T Intellectual Property I, L.P. | Launcher with helical antenna and methods for use therewith |
| US10637149B2 (en) | 2016-12-06 | 2020-04-28 | At&T Intellectual Property I, L.P. | Injection molded dielectric antenna and methods for use therewith |
| US10938108B2 (en) | 2016-12-08 | 2021-03-02 | At&T Intellectual Property I, L.P. | Frequency selective multi-feed dielectric antenna system and methods for use therewith |
| US10601494B2 (en) | 2016-12-08 | 2020-03-24 | At&T Intellectual Property I, L.P. | Dual-band communication device and method for use therewith |
| US10777873B2 (en) | 2016-12-08 | 2020-09-15 | At&T Intellectual Property I, L.P. | Method and apparatus for mounting network devices |
| US10916969B2 (en) | 2016-12-08 | 2021-02-09 | At&T Intellectual Property I, L.P. | Method and apparatus for providing power using an inductive coupling |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB918217A (cs) * | 1900-01-01 | |||
| BE591650A (fr) * | 1959-06-10 | 1960-10-03 | Abbott Lab | Procédé pour inhiber l'action de la mono-amine-oxydase chez les animaux à sang chaud |
| US3121745A (en) * | 1961-03-23 | 1964-02-18 | Dow Chemical Co | Propynly p-nitroanilines |
| US3149160A (en) * | 1961-03-23 | 1964-09-15 | Dow Chemical Co | Nu-(2-propynyl) omiron-bromoaniline |
| US3231614A (en) * | 1963-12-26 | 1966-01-25 | Dow Chemical Co | N-2-propynyl and n, n-di(2-propynyl)-(2-propynyloxy)-anilines |
| US3781443A (en) * | 1971-10-26 | 1973-12-25 | Lilly Co Eli | Phenethanolamine n-methyl transferase inhibiting benzylamines |
-
1976
- 1976-03-04 DE DE19762609280 patent/DE2609280A1/de not_active Withdrawn
-
1977
- 1977-01-26 LU LU76644A patent/LU76644A1/xx unknown
- 1977-02-04 CS CS77749A patent/CS193084B2/cs unknown
- 1977-02-08 DK DK50977A patent/DK50977A/da not_active Application Discontinuation
- 1977-02-10 CA CA271,480A patent/CA1090250A/en not_active Expired
- 1977-02-15 NL NL7701575A patent/NL7701575A/xx not_active Application Discontinuation
- 1977-02-16 IL IL51463A patent/IL51463A/xx unknown
- 1977-02-21 GB GB7195/77A patent/GB1578852A/en not_active Expired
- 1977-03-02 IE IE450/77A patent/IE45599B1/en unknown
- 1977-03-03 HU HU77SCHE596A patent/HU177907B/hu unknown
- 1977-03-03 SU SU772456551A patent/SU656462A3/ru active
- 1977-03-03 AU AU22897/77A patent/AU508246B2/en not_active Expired
- 1977-03-04 DD DD7700197682A patent/DD129611A5/xx unknown
- 1977-03-04 BE BE175468A patent/BE852088A/xx not_active IP Right Cessation
- 1977-03-04 JP JP2370277A patent/JPS52108022A/ja active Granted
- 1977-03-04 FR FR7706455A patent/FR2342661A1/fr active Granted
- 1977-03-04 IT IT20932/77A patent/IT1143638B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| HU177907B (en) | 1982-01-28 |
| IL51463A0 (en) | 1977-04-29 |
| IT1143638B (it) | 1986-10-22 |
| JPS52108022A (en) | 1977-09-10 |
| IE45599B1 (en) | 1982-10-06 |
| IL51463A (en) | 1980-11-30 |
| AU2289777A (en) | 1978-09-07 |
| LU76644A1 (cs) | 1977-06-24 |
| FR2342661A1 (fr) | 1977-09-30 |
| AU508246B2 (en) | 1980-03-13 |
| GB1578852A (en) | 1980-11-12 |
| FR2342661B1 (cs) | 1980-06-27 |
| SU656462A3 (ru) | 1979-04-05 |
| JPS574601B2 (cs) | 1982-01-27 |
| NL7701575A (nl) | 1977-09-06 |
| DD129611A5 (de) | 1978-02-01 |
| DE2609280A1 (de) | 1977-09-15 |
| DK50977A (da) | 1977-09-05 |
| BE852088A (fr) | 1977-09-05 |
| CS193084B2 (en) | 1979-09-17 |
| IE45599L (en) | 1977-09-04 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |