GB917924A - Improvements in or relating to organophosphorus insecticides - Google Patents
Improvements in or relating to organophosphorus insecticidesInfo
- Publication number
- GB917924A GB917924A GB13034/59A GB1303459A GB917924A GB 917924 A GB917924 A GB 917924A GB 13034/59 A GB13034/59 A GB 13034/59A GB 1303459 A GB1303459 A GB 1303459A GB 917924 A GB917924 A GB 917924A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- group
- aralkyl
- hcl
- 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
- 239000002917 insecticide Substances 0.000 title 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- 125000002723 alicyclic group Chemical group 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 239000011230 binding agent Substances 0.000 abstract 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000007530 organic bases Chemical class 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 abstract 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 abstract 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 abstract 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 1
- HFOBXJCKEJSWGH-UHFFFAOYSA-N [Cl-].ClCC(=O)NC[N+]1=CC=CC=C1 Chemical compound [Cl-].ClCC(=O)NC[N+]1=CC=CC=C1 HFOBXJCKEJSWGH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- AQIAIZBHFAKICS-UHFFFAOYSA-N methylaminomethyl Chemical compound [CH2]NC AQIAIZBHFAKICS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 239000006072 paste Substances 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 abstract 1
- 235000010234 sodium benzoate Nutrition 0.000 abstract 1
- 239000004299 sodium benzoate Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of formula <FORM:0917924/IV (b)/1> where X and Y are oxygen or sulphur, at least one being sulphur; R and R1 are C1-4 alkyl; R2 and R3 are hydrogen or unsubstituted or substituted alkyl; Z is one of the following groups:- (i) a hydroxyl group when R2 or R3 is alkyl or substituted alkyl and X and Y are different; (ii) the group OR4, where R4 is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkyl interrupted in the chain by, e.g. an oxygen or sulphur atom or a carbonyl group, aryl, substituted aryl, aralkyl, substituted aralkyl, an alicyclic group, a heterocyclic or substituted heterocyclic group, or an acyl group; (iii) a dithiocarbamoyl or substituted dithiocarbamoyl group; or (iv) the group NR5R6 where R5 is hydrogen, alkyl, substituted alkyl, aralkyl, substituted aralkyl or an alicyclic group and R6 is alkyl, substituted alkyl, aralkyl, substituted aralkyl or an alicyclic group or NR5R6 together form the residue of a heterocyclic ring together with acid addition and quaternary ammonium salts thereof. Specified substituents include halogen, alkoxy and alkylmercapto groups. They may be prepared by reacting a compound of formula <FORM:0917924/IV (b)/2> where M is hydrogen, alkali metal or ammonium in the presence of an inert solvent with a compound A-CHR2.CONH.CHR3.Z where A is chlorine, bromine or iodine, an acid binding agent being used when M is hydrogen. Alternatively a compound <FORM:0917924/IV (b)/3> may be treated by known methods to replace OH by Z. The products are pesticides (see Group VI). Compounds of the formula <FORM:0917924/IV (b)/4> are stabilized by admixture with an acid binding agent and/or an alkanol. Specified acid binding agents include aqueous ammonia, epichlorhydrin, epoxidised fatty acids, glycidyl ethers, and organic bases. The following are prepared as starting materials: (C2H5O)2P(S)SCH2CONHCH2OH and (C2H5O)2P(S)OCH2CONHCH2OH by reacting ClCH2CONHCH2OH with (C2H5O)P (S)SK and (C2H5O)2P(S)OK respectively; compounds ClCH2CONHCH2OR1 where R1 is methyl, ethyl, isopropyl, n-butyl, allyl, cyclohexyl, benzyl, chloroethyl and p-chlorophenyl by reacting R1OH with ClCH2CONHCH2OH in the presence of HCl; ClCH2CONHCH2 OCH2CH2OCH2CH3, ClCH2CONHCH2O-tetrahydrofurfuryl, ClCH2CONHCH2OCH2CH2N (C2H5)2, ClCH2CONHCH2OCOC6H5, ClCH2 CONHCH2SC(S)N(CH3)2, ClCH2CONHCH2N (C2H5)2.HCl, ClCH2CONHCH2N(CH3)2.HCl, ClCH2CONHCH2NHC2H5.HCl, ClCH2CONH CH2NHCH3.HCl, ClCH2CONHCH2NH.CH2 C6H5.HCl, ClCH2CONHCH2NHC6H11.HCl and ClCH2CONHCH2-morpholinyl.HCl are prepared by reacting ClCH2CONHCH2Cl with C2H5OCH2CH2OH, tetrahydrofurfuryl alcohol, (C2H5)2NCH2CH2OH, sodium benzoate, NaSC (S)N(CH3)2 and the appropriate amine respectively; N - (chloracetamidomethyl)pyridinium chloride from ClCH2CONHCH2Cl and pyridine; ClCH2CONHCH[SC(S)N(CH3)2]CCl3 from ClCH2CONHCHClCCl3 and NaSC(S)N(CH3)2; CH3CHClCONHCH2OH by the action of HCHO on CH3CHClCONH2; CH3CHClCONH CH2OCH3 and CH3CHClCONHCH2OC2H5\t by reacting CH3CHClCONHCH2OH with CH3OH and C2H5OH respectively in the presence of HCl; ClCH2CONHCH2Cl and ClCH2CONH CHClCCl3 from thionyl chloride and ClCH2 CONHCH2OH and ClCH2CONHCHOHCCl3 respectively; ClCH2CONHCH(OCH3)CCl3 from ClCH2CONHCHOHCCl3 and sodium methoxide; ClCH2CONHCHOHCCl3 from chloral and ClCH2CONH2. The Provisional Specification refers also to compounds in which Z is SR4, -S.C(S)OC2H5 or -S.C(O)OC2H5 and in which Z is hydroxyl when R2 and R3 are alkyl or substituted alkyl. Exemplified compounds are: (C2H5O)2P(S)SCH2 CONHCH2SC2H5; (C2H5O)2P(S)SCH2CONH CH2S-C6H4-p-Cl; and (C2H5O)2P(S)OCH2 CONHCH2SC2H5.ALSO:Pesticidal compositions comprise compounds of formula <FORM:0917924/VI/1> where X and Y are oxygen or sulphur, at least one being sulphur; R and R1 are C1-4 alkyl; R2 and R3 are hydrogen or unsubstituted or substituted alkyl; Z is one of the following groups: (i) a hydroxyl group when R2 or R3 is alkyl or substituted alkyl and X and Y are different; (ii) the group OR41, where R4 is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkyl interrupted in the chain by e.g. an oxygen or sulphur-atom or a carbonyl group, aryl, substituted aryl, aralkyl, substituted aralkyl, an alicyclic group, a heterocyclic or substituted heterocyclic group, or an acyl group; (iii) a dithiocarbamoyl or substituted dithiocarbamoyl group; or (iv) the group NR5R6, where R5 is hydrogen, alkyl, substituted alkyl, aralkyl, substituted aralkyl or an alicyclic group and R6 is alkyl substituted alkyl, aralkyl, substituted aralkyl or an alicyclic group or NR5R6 together form the residue of a heterocyclic ring together with acid addition and quaternary ammonium salts thereof, together with a carrier e.g. as emulsions, aerosols, dusts, wettable powders, granulates, pellets or pastes. Specified substituents include halogen, alkoxy and alkylmercapto groups. Additives include surface active agents and adhesives. The invention also comprises pesticidal compositions of improved stability comprising a compound of formula <FORM:0917924/VI/2> in admixture with an acid binding agent, e.g. aqueous ammonia, an organic base or an epoxy compound such as epichlorhydrin, phenyl glycidyl ether or epoxidised fatty acids, pyridine or ethylene diamine, preferably dissolved in an alkanol.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL258466D NL258466A (en) | 1959-04-16 | ||
| IT628077D IT628077A (en) | 1959-04-16 | ||
| BE597523D BE597523A (en) | 1959-04-16 | ||
| GB13034/59A GB917924A (en) | 1959-04-16 | 1959-04-16 | Improvements in or relating to organophosphorus insecticides |
| CH1628565A CH421609A (en) | 1959-04-16 | 1960-04-14 | Process for making a verminicide |
| DE19601693197D DE1693197B1 (en) | 1959-04-16 | 1960-04-14 | 0,0-Dialkyl-S- (or-0-) - (N-alkoxymethyl) -carbamoylmethyl-thionophosphoric acid ester and process for their preparation |
| CH428160A CH419723A (en) | 1959-04-16 | 1960-04-14 | Verminicide |
| FR824598A FR1269087A (en) | 1959-04-16 | 1960-04-16 | New phosphorothionates and phosphorothiolothionates, their applications as insecticides and their preparation process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13034/59A GB917924A (en) | 1959-04-16 | 1959-04-16 | Improvements in or relating to organophosphorus insecticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB917924A true GB917924A (en) | 1963-02-13 |
Family
ID=10015597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13034/59A Expired GB917924A (en) | 1959-04-16 | 1959-04-16 | Improvements in or relating to organophosphorus insecticides |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE597523A (en) |
| CH (2) | CH419723A (en) |
| DE (1) | DE1693197B1 (en) |
| GB (1) | GB917924A (en) |
| IT (1) | IT628077A (en) |
| NL (1) | NL258466A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442945A (en) * | 1967-05-22 | 1969-05-06 | Monsanto Co | Phytotoxic alpha-halo-acetanilides |
| FR2844264A1 (en) * | 2002-09-11 | 2004-03-12 | Rhodia Chimie Sa | New halogenated S-alpha-aminoalkyl thicarbonylsulfanyl compounds, useful as reagents in radical addition reactions, especially for the preparation of biologically active trifluoromethylamine compounds |
-
0
- IT IT628077D patent/IT628077A/it unknown
- NL NL258466D patent/NL258466A/xx unknown
- BE BE597523D patent/BE597523A/xx unknown
-
1959
- 1959-04-16 GB GB13034/59A patent/GB917924A/en not_active Expired
-
1960
- 1960-04-14 DE DE19601693197D patent/DE1693197B1/en active Pending
- 1960-04-14 CH CH428160A patent/CH419723A/en unknown
- 1960-04-14 CH CH1628565A patent/CH421609A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442945A (en) * | 1967-05-22 | 1969-05-06 | Monsanto Co | Phytotoxic alpha-halo-acetanilides |
| FR2844264A1 (en) * | 2002-09-11 | 2004-03-12 | Rhodia Chimie Sa | New halogenated S-alpha-aminoalkyl thicarbonylsulfanyl compounds, useful as reagents in radical addition reactions, especially for the preparation of biologically active trifluoromethylamine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CH421609A (en) | 1966-09-30 |
| BE597523A (en) | |
| DE1693197B1 (en) | 1972-07-06 |
| CH419723A (en) | 1966-08-31 |
| NL258466A (en) | |
| IT628077A (en) |
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