GB823415A - Preparations containing phosphorus- and halogen-containing condensation products - Google Patents
Preparations containing phosphorus- and halogen-containing condensation productsInfo
- Publication number
- GB823415A GB823415A GB27801/56A GB2780156A GB823415A GB 823415 A GB823415 A GB 823415A GB 27801/56 A GB27801/56 A GB 27801/56A GB 2780156 A GB2780156 A GB 2780156A GB 823415 A GB823415 A GB 823415A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- condensation product
- formula
- methyl
- ester
- 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
- 239000007859 condensation product Substances 0.000 title abstract 11
- 238000002360 preparation method Methods 0.000 title abstract 3
- 229910052736 halogen Inorganic materials 0.000 title 1
- 150000002367 halogens Chemical class 0.000 title 1
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 abstract 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 239000003085 diluting agent Substances 0.000 abstract 4
- 239000000203 mixture Chemical group 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003208 petroleum Substances 0.000 abstract 3
- 229960004319 trichloroacetic acid Drugs 0.000 abstract 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000005995 Aluminium silicate Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 235000012211 aluminium silicate Nutrition 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 239000000440 bentonite Substances 0.000 abstract 2
- 229910000278 bentonite Inorganic materials 0.000 abstract 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 abstract 2
- UAMJIPWXLGMBPW-UHFFFAOYSA-N (4-chlorophenyl) 2,2,2-trichloroacetate Chemical compound ClC1=CC=C(OC(=O)C(Cl)(Cl)Cl)C=C1 UAMJIPWXLGMBPW-UHFFFAOYSA-N 0.000 abstract 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 abstract 1
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 abstract 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 abstract 1
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 abstract 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 abstract 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000005752 Copper oxychloride Substances 0.000 abstract 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 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 235000012216 bentonite Nutrition 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000010440 gypsum Substances 0.000 abstract 1
- 229910052602 gypsum Inorganic materials 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 229960004592 isopropanol Drugs 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 125000000486 o-cresyl group Chemical group [H]C1=C([H])C(O*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 125000000552 p-cresyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1O*)C([H])([H])[H] 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 239000000080 wetting agent Substances 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Condensation products of the probable general formula <FORM:0823415/IV (a)/1> (wherein R and R1 are aliphatic hydrocarbon radicals of 1 to 4 carbon atoms which may be substituted by chloro, cyano or thiocyano groups and R2 is an aryl radical which may be substituted by alkyl, alkoxy, cycloalkyl, chloro or nitro groups) are prepared by reacting a compound of the formula <FORM:0823415/IV (a)/2> with the appropriate trichloracetic acid aryl ester. The reaction may be performed in an inert solvent. In an example, trichloracetic acid p-chlorophenol ester is heated to 60 DEG C. with trimethyl phosphite in benzene, and subsequently to reflux temperature, giving a product of the probable formula (I) above wherein R and R1 are methyl and R2 is p-chlorophenyl. Further compounds of probable formula (I) are also described, wherein R and R1 are variously methyl and ethyl and R2 is phenyl, o-, m- and p-chlorophenyl, o-, m- and p-cresyl and mixtures thereof, 3-methyl-4-chlorophenyl, p-nitrophenyl, p - amyl - phenyl, p - methoxy - phenyl, p - cyclo - hexyl - phenyl, alpha- and beta-naphthyl and 2 : 4-dimethyl. Reference is also made to R and R1 being propyl, iso-propyl, butyl, allyl and 2-chloroethyl radicals and to R2 being a diphenyl radical. Specification 775,085 is referred to.ALSO:The invention comprises a pest combating preparation which contains as the active ingredient a condensation product of a phosphite of the general formula <FORM:0823415/VI/1> (wherein R and R1 are aliphatic hydrocarbon radicals of 1 to 4 carbon atoms which may be substituted by chloro, cyano or thiocyano groups) with an ester of the formula <FORM:0823415/VI/2> (wherein R2 is an aryl radical which may be substituted by alkyl, alkoxy, cycloalkyl, chloro or nitro groups) in admixture with a solid powdered diluent or a liquid diluent and an emulsifying or wetting agent. The condensation products have the probable formula <FORM:0823415/VI/3> Suitable liquid diluents are lower alkanols, acetone, methyl ethyl ketone, methyl cyclohexanol, benzene, toluene, kerosene, white spirit, petroleum and tar distillates and suitable solid diluents are kaolin, gypsum and bentonite and further additives such as sulphite cellulose waste liquor and cellulose derivatives. Suitable emulsifying agents are condensation products from aliphatic alcohols or amines or carboxylic acids which contain a long-chain hydrocarbon radical, e.g. octadecyl alcohol, soya oil fatty acid, oleylamine or dodecyl mercaptan, with ethylene oxide, the sodium salt of lauryl sulphonic acid or of dodecyl benzene sulphonic acid, the sodium or triethanolamine salt of oleic or abietic acid or mixtures of these, the sodium salt of petroleum sulphonic acid and dodecyl pyridinium chloride. Other insecticides and/or fungicides may also be added to the preparations which may take the form of powders, aqueous dispersions, pastes or self-dispersing oils. Examples describe the following compositions: (1) the condensation product of p-chlorophenyl trichloracetate and trimethyl phosphite, octylphenol polyglycol ether, oleic acid and mineral oil; (2) the condensation product of (1), the condensation product of dodecyl mercaptan and ethylene oxide and iso-propanol; (3) the condensation product of (1) and petroleum sulphonic acid sodium salt; (4) the condensation product from triethyl phosphite and trichloroacetic acid p-cresol ester and talcum or bentonite, kaolin or mixtures thereof; (5) the condensation product from trimethyl phosphite and trichloracetic acid p-cresol ester, sulphur and copper oxychloride. Specification 775,085 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH823415X | 1955-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB823415A true GB823415A (en) | 1959-11-11 |
Family
ID=4539681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27801/56A Expired GB823415A (en) | 1955-09-12 | 1956-09-11 | Preparations containing phosphorus- and halogen-containing condensation products |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1156652A (en) |
| GB (1) | GB823415A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141123A (en) * | 1983-05-17 | 1984-12-12 | Chinoin Gyogyszer Es Vegyeszet | Phosphorus substituted acetic acid derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK324778A (en) * | 1977-08-26 | 1979-02-27 | Du Pont | HERBICIDE PHOSPHONATES |
-
1956
- 1956-09-07 FR FR1156652D patent/FR1156652A/en not_active Expired
- 1956-09-11 GB GB27801/56A patent/GB823415A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141123A (en) * | 1983-05-17 | 1984-12-12 | Chinoin Gyogyszer Es Vegyeszet | Phosphorus substituted acetic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1156652A (en) | 1958-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB710515A (en) | Fuel oil compositions | |
| GB819850A (en) | New phosphoric esters, process for their preparation and compositions containing same | |
| GB792608A (en) | New organic thiophosphoric acid derivatives, process for their preparation and compositions containing same | |
| GB823415A (en) | Preparations containing phosphorus- and halogen-containing condensation products | |
| US2553778A (en) | Parasiticidal compositions containing reaction products of mercapto acetic acid esters and perchloromethylmercaptan | |
| US3781426A (en) | Phosphoric acid esters and pesticidal preparations containing them | |
| US3461132A (en) | Novel tin complexes | |
| GB944840A (en) | New dithiophosphoric esters and processes for their manufacture | |
| GB874570A (en) | Thiophosphoric acid esters | |
| GB742796A (en) | Organic derivatives of thiophosphoric acid | |
| GB775085A (en) | Preparations for combating pests | |
| US3185723A (en) | O-alkyl, s, 1-phenyl-2-alkoxycarbonylethyl alkylphosphonothioates | |
| GB758926A (en) | New sulphur containing compounds | |
| US2861914A (en) | New halogen and phosphor containing compounds and method for their use | |
| US3459857A (en) | Phospho-acid esters as fungitoxic agents | |
| US3634557A (en) | Oxime thiophosphates | |
| US3250826A (en) | Thiophosphate esters | |
| GB1033265A (en) | Cyano-phenyl ester derivatives of thio phosphorus acids | |
| US2409828A (en) | Aminomethyl amidothiazoles | |
| US3178338A (en) | Method of combating nematodes, and nematocidal preparations | |
| GB954234A (en) | Thiophosphoric acid esters, process of preparing same and insecticidal composition containing same | |
| US3136686A (en) | Omicron, omicron-dialkyl s-alkenyl phosphorothioates and insecticidal compositions and methods employing same | |
| US3756802A (en) | Method of defoliating plants | |
| GB795340A (en) | New insecticidal esters of dithiophosphoric acid | |
| GB819066A (en) | New compounds containing phosphorus and sulphur, their manufacture and use |