US2225573A - Insecticide, fungicide, and the like - Google Patents
Insecticide, fungicide, and the like Download PDFInfo
- Publication number
- US2225573A US2225573A US133185A US13318537A US2225573A US 2225573 A US2225573 A US 2225573A US 133185 A US133185 A US 133185A US 13318537 A US13318537 A US 13318537A US 2225573 A US2225573 A US 2225573A
- Authority
- US
- United States
- Prior art keywords
- sulfide
- sulfides
- insecticide
- ethylene
- fungicide
- 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 - Lifetime
Links
- 239000002917 insecticide Substances 0.000 title description 10
- 230000000855 fungicidal effect Effects 0.000 title description 7
- 239000000417 fungicide Substances 0.000 title description 5
- 150000003568 thioethers Chemical class 0.000 description 19
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 7
- -1 alicyclic hydrocarbons Chemical class 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 239000002316 fumigant Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- ZMJBHCIEMIVIFZ-UHFFFAOYSA-N 2,3-dimethylthiirane Chemical compound CC1SC1C ZMJBHCIEMIVIFZ-UHFFFAOYSA-N 0.000 description 1
- XIVQIMJXNTVZJM-UHFFFAOYSA-N 2-ethyl-2-methylthiirane Chemical compound CCC1(C)CS1 XIVQIMJXNTVZJM-UHFFFAOYSA-N 0.000 description 1
- OQOIYECUXDNABI-UHFFFAOYSA-N 2-phenylthiirane Chemical compound C1SC1C1=CC=CC=C1 OQOIYECUXDNABI-UHFFFAOYSA-N 0.000 description 1
- WANYALBJJNAUTC-UHFFFAOYSA-N 2-prop-1-en-2-ylthiirane Chemical compound CC(=C)C1CS1 WANYALBJJNAUTC-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- ALSDAQUNVROJFE-UHFFFAOYSA-N 3-methyloxathietane Chemical compound CC1COS1 ALSDAQUNVROJFE-UHFFFAOYSA-N 0.000 description 1
- 102100022144 Achaete-scute homolog 2 Human genes 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000510672 Cuminum Species 0.000 description 1
- 235000007129 Cuminum cyminum Nutrition 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 101000901109 Homo sapiens Achaete-scute homolog 2 Proteins 0.000 description 1
- 101000703089 Homo sapiens Set1/Ash2 histone methyltransferase complex subunit ASH2 Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- CXYRUNPLKGGUJF-OZVSTBQFSA-M pamine Chemical compound [Br-].C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-OZVSTBQFSA-M 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- One object of the invention is toprovide a s 5 material which is convenient to ship, store and I handle and which can be effectively used for inmmethyl fm sulfide secticidal ⁇ fungicidal and bactericidal purposes.
- 2 sulfides of this type may be derived from either p s g0 unsaturated aliphatic or alicyclic hydrocarbons and not only may the sulfides themselves be used 3 but also suitable-derivatives thereofand homologous saturated aliphatic sulfides, as
- cordance with my invention include, for example, such as butadlene monosumde an alkyl sulfides, such as ethylene sulfide s a propylene smnde isoprene monosulfide 80 cn,-cH-cm V 5 I taupe-05 021- symmetrical dimethyl ethylene sulfide s I CI-Ir-CH-CH-CH; and the like, and the corresponding polysulfides 35 f as butadiene disulfide isobutylene sulfide 3 7 57 CH, SV 8 40 CHw-t'J-CH.
- butadlene monosumde an alkyl sulfides such as ethylene sulfide s a propylene smnde isoprene monosulfide 80 cn,-cH-cm V 5 I taupe-05 021- symmetrical dimethyl ethylene sulfide s I CI-Ir-CH
- analogous sulfides of 40 cyclic compounds including both aliphatic alnd m 1e, as c c od butylene sulfide gigriggisutlagniiiounds, such for exa p y I cm p 0 cm cm-Jm-cm-cn.
- This invention relates to materials useful for isopropyl ethylene sulfidedestroying vermin and other noxious organisms CHr-CH--CHCHr-CH: I u s and the like.
- substituents 2 such as halogen, #41112, on, COOH, --CN, ASH2, etc., as oxypropylene sulfide I nof-cnrcn-s- -cm monochlor ethylene sulfide CIS-7C;H' C
- sulfides may be applied as the chemical individuals or as mixtures thereof or as crude materials containing other compounds which may or may not have a similar action under the conditions of application, such, for example, as the mixtures of sulfides and dithlocyanates obtainable as crude products in one method of manufacturing thesulfides.
- Other substances which ma act solely as diluents or carriers, such as hydrocarbons, kieselguhr, etc., or which may possess desirable insecticidal, fungicidal or bactericidal properties, as HCN, CS2, epoxyethane or the like, may be added to the sulfide or sulfides chosen,.either before or at the time of application.
- the sulfides used in my insecticidal preparations may be manufactured by reaction of suitable dithiocyanates with a solution of NazS containing NaHS, a process described, for example, by Delpine in the Bull. Soc. Chim. (4) 27, 740 (1920). It has been found desirable to avoid as much as possible any substantial rise in temperature during the process, and not as generally recommended in the literature, to separate the product from the reaction mixture by distillation with steam, but to isolate it from the re: action mixture by means of vacuum distillation at a low temperature. As the before mentioned sulfides, especially the lower sulfides are somewhat unstable, they are preferably used'together with suitable amounts of stabilizing agents such as phenols, etc.
- the lower molecular sulfides are in general volatile. substances which evaporate readily and have been found to be eminently suitable for use as so-called gassing insecticides. As such they may be effectively used in destroying insects in food stuffs and in fumigating warehouses, dwellings and ships as well as for the destruction of vermin on 'human beings and animals.
- the higher molecular sulfides are less volatile and may, therefore, be more suitably used as contacting. or stomachal insecticides, e. g. for combating plant lice and in orchardsprays, etc'., for protection against aphids, scale, etc.
- ethylene sulfide is especially useful for insecticidal and analogous purposes. "Its activity is such that it may be used effectively at. lo'w'concentrations which lie outside the explosive limits. For this reason it makes a desirable substitute for carbon disulfide fumigants and cumin fact be safely employed where the fire hazard of the latter makes it too dangerous to use.
- ethylene sulfide was found to be about'twenty times as effective as ethylene oxide.
- ethylene sulfide was introduced into a closed volume of airto a concentration of only 0.1%. At this low concentration the cockroaches My invention is not only capable of wide variation with respect tothe type of organic sulfide having a sulfur atom attached to two carbon atoms joined in a saturated carbon chain,
- v Asan insecticide, fungicide, bactericide and the like, a preparation containing as an active ingredient an organic sulfide having at least one 'sulfur atom attached to two directly-connected carbon atoms.
- An insecticide composition containing an effective amount of an alkyl sulfide having a sulfur atom attached to two directly connected saturated carbon atoms.
- a fumigant comprising an effective amount of ethylene sulfide.
- a fumigant comprising an effective amount of a butylene sulfide.
Description
and deals with a new class of compounds which E are particularly advantageous for such uses. I 7 V 9 One object of the invention is toprovide a s 5 material which is convenient to ship, store and I handle and which can be effectively used for inmmethyl fm sulfide secticidal} fungicidal and bactericidal purposes. CE:
I haveiound that sulfides containing at least it) one sulfur atom attached to two carbon atoms 10 which are joined in a saturated carbon chain, S and especially those having a sulfur atom attetramethyl ethylene sulfide tached to two directly connected carbon atoms CH CH e. g. sulfides containing the group \C CHr- V Cl 3a I 15 v \B I trime vlene sulfide are particularly effective for the said. purposes. 2 sulfides of this type may be derived from either p s g0 unsaturated aliphatic or alicyclic hydrocarbons and not only may the sulfides themselves be used 3 but also suitable-derivatives thereofand homologous saturated aliphatic sulfides, as
Typical sulfides which may be used in well as the similar unsaturated aliphatic-sulfides 25. cordance with my invention include, for example, such as butadlene monosumde an alkyl sulfides, such as ethylene sulfide s a propylene smnde isoprene monosulfide 80 cn,-cH-cm V 5 I taupe-05 021- symmetrical dimethyl ethylene sulfide s I CI-Ir-CH-CH-CH; and the like, and the corresponding polysulfides 35 f as butadiene disulfide isobutylene sulfide 3 7 57 CH, SV 8 40 CHw-t'J-CH. etc. Also suitable are the analogous sulfides of 40 cyclic compounds including both aliphatic alnd m 1e, as c c od butylene sulfide gigriggisutlagniiiounds, such for exa p y I cm p 0 cm cm-Jm-cm-cn.
v c e11.
CHr-CH a amylene sulfide ';7 styrene sulfide 7 g symmetrical methyl ethyl ethylene sulfide ogj n Patented Dec. 194) I I i I UNITED STATES PATENT OFFICE INSECTICIDE, FUNGICIDE, AND THE Henrlcus Jacobus Charles Tendeloo, The Hague, Netherlands, assignor to Shell Development Company, San Francisco, Calif., a corporation of Delaware j 1 A NmDrawing. Application March 26, 1-937, Sell'gzlsNo. 133,185. In the Netherlands April 20,
8 Claims. (01. 167-33) This invention relates to materials useful for isopropyl ethylene sulfidedestroying vermin and other noxious organisms CHr-CH--CHCHr-CH: I u s and the like. sulfides containing substituents 2 such as halogen, #41112, on, COOH, --CN, ASH2, etc., as oxypropylene sulfide I nof-cnrcn-s- -cm monochlor ethylene sulfide CIS-7C;H' C| andthe like, may be used in place of or admixed with, the unsubstituted sulfide or sulfides chosen. These sulfides may be applied as the chemical individuals or as mixtures thereof or as crude materials containing other compounds which may or may not have a similar action under the conditions of application, such, for example, as the mixtures of sulfides and dithlocyanates obtainable as crude products in one method of manufacturing thesulfides. Other substances, which ma act solely as diluents or carriers, such as hydrocarbons, kieselguhr, etc., or which may possess desirable insecticidal, fungicidal or bactericidal properties, as HCN, CS2, epoxyethane or the like, may be added to the sulfide or sulfides chosen,.either before or at the time of application. In general, the sulfides used in my insecticidal preparations, may be manufactured by reaction of suitable dithiocyanates with a solution of NazS containing NaHS, a process described, for example, by Delpine in the Bull. Soc. Chim. (4) 27, 740 (1920). It has been found desirable to avoid as much as possible any substantial rise in temperature during the process, and not as generally recommended in the literature, to separate the product from the reaction mixture by distillation with steam, but to isolate it from the re: action mixture by means of vacuum distillation at a low temperature. As the before mentioned sulfides, especially the lower sulfides are somewhat unstable, they are preferably used'together with suitable amounts of stabilizing agents such as phenols, etc.
The lower molecular sulfides are in general volatile. substances which evaporate readily and have been found to be eminently suitable for use as so-called gassing insecticides. As such they may be effectively used in destroying insects in food stuffs and in fumigating warehouses, dwellings and ships as well as for the destruction of vermin on 'human beings and animals. The higher molecular sulfides are less volatile and may, therefore, be more suitably used as contacting. or stomachal insecticides, e. g. for combating plant lice and in orchardsprays, etc'., for protection against aphids, scale, etc.
For the purpose of making my invention more clear itwill be further described with more parti ular reference to the use of ethylene sulfide awn me sulfides. It will be understood that this imp e's no limitation on my invention. however, as the other sulfides already referred to are also eflective in similar and other suitable applications. a
Because of its low boiling point (55 C.) and its exceptional activity ethylene sulfide is especially useful for insecticidal and analogous purposes. "Its activity is such that it may be used effectively at. lo'w'concentrations which lie outside the explosive limits. For this reason it makes a desirable substitute for carbon disulfide fumigants and cumin fact be safely employed where the fire hazard of the latter makes it too dangerous to use. In comparative tests on cockroaches. ethylene sulfide was found to be about'twenty times as effective as ethylene oxide. In a representative test ethylene sulfide was introduced into a closed volume of airto a concentration of only 0.1%. At this low concentration the cockroaches My invention is not only capable of wide variation with respect tothe type of organic sulfide having a sulfur atom attached to two carbon atoms joined in a saturated carbon chain,
which may be used, but also with respect to the 3 character of organisms whichinay be controlled therewith, asl these also include flies, gnats, mosquitoes, weevils, beetles and the like. It will therefore be clear that my invention is not to be regarded as limited to'the details of operation described, but only by the terms of the accompanying claims, in which it is my intention to claim all novelty inherent therein as bro 3 as is possible in view of the prior art.
I claim as my invention; v 1. Asan insecticide, fungicide, bactericide and the like, a preparation containing as an active ingredient an organic sulfide having at least one 'sulfur atom attached to two directly-connected carbon atoms.
- 2. As an insecticide, fungicide, bactericide and the like, a preparation containing as an active.
ingredient an aliphatic monomeric organic sulfide liaving a sulfur atom attached to two directly connected carbon atoms which are joined in a saturated carbon chain.
'3. An insecticide composition containing an effective amount of an alkyl sulfide having a sulfur atom attached to two directly connected saturated carbon atoms.
-, 4. An insecticide containing as an active ingredient an unsaturated aliphatic sulfide having a sulfur atom attached totwo directly connected saturated carbon atoms.
5. An insecticide containing asan active ingradient a carbocyclic sulfide having a sulfur atom attached to two'directly connected saturated carbon atoms. I
- 6. A fumigant comprising an effective amount of ethylene sulfide.
. 7. A fumigant comprising an effective amount of a butylene sulfide.
8. As an insecticide, fungicide, bactericide and the like, a preparation containing as an active ingredient an aliphatic monomeric organic sulfide having a sulfur atom attached to two carbon atoms which are joined in a saturated carbon chain through an ethylene radical.
' unisia-Ices JACOBUS CHARLES'TENDELOQ'
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2225573X | 1936-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2225573A true US2225573A (en) | 1940-12-17 |
Family
ID=19873914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US133185A Expired - Lifetime US2225573A (en) | 1936-04-20 | 1937-03-26 | Insecticide, fungicide, and the like |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2225573A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2481140A (en) * | 1946-09-16 | 1949-09-06 | Shell Dev | Process and products of sulfurization of linear methylpentadiene polymers |
| US2505870A (en) * | 1947-05-09 | 1950-05-02 | Phillips Petroleum Co | Secondary and tertiary alkylthiol amines and their production |
| US2542832A (en) * | 1945-10-23 | 1951-02-20 | Socony Vacuum Oil Co Inc | Alkyl sulfo-alkenyl phenols and salts thereof |
| US2676131A (en) * | 1948-12-04 | 1954-04-20 | Shell Dev | Halogenated heterocyclic insect toxicants |
| US2824845A (en) * | 1954-02-26 | 1958-02-25 | Monsanto Chemicals | Episulfide compounds and stabilized polymer compositions containing same |
| US3324148A (en) * | 1963-06-05 | 1967-06-06 | Union Carbide Corp | Organic azidoformates and methods of preparing same |
| US3357991A (en) * | 1962-06-06 | 1967-12-12 | Standard Oil Co | Alkylenemonothiolcarbonate preparation |
| US3372089A (en) * | 1966-08-15 | 1968-03-05 | Allied Chem | Combating staphylococcus aureus with 3-thietanol |
| US3382094A (en) * | 1964-05-19 | 1968-05-07 | Thiokol Chemical Corp | Fluid and mold resistant cellulosic materials and process therefor |
| US3403166A (en) * | 1964-08-01 | 1968-09-24 | Dunlop Co Ltd | Episulfide production |
-
1937
- 1937-03-26 US US133185A patent/US2225573A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542832A (en) * | 1945-10-23 | 1951-02-20 | Socony Vacuum Oil Co Inc | Alkyl sulfo-alkenyl phenols and salts thereof |
| US2481140A (en) * | 1946-09-16 | 1949-09-06 | Shell Dev | Process and products of sulfurization of linear methylpentadiene polymers |
| US2505870A (en) * | 1947-05-09 | 1950-05-02 | Phillips Petroleum Co | Secondary and tertiary alkylthiol amines and their production |
| US2676131A (en) * | 1948-12-04 | 1954-04-20 | Shell Dev | Halogenated heterocyclic insect toxicants |
| US2824845A (en) * | 1954-02-26 | 1958-02-25 | Monsanto Chemicals | Episulfide compounds and stabilized polymer compositions containing same |
| US3357991A (en) * | 1962-06-06 | 1967-12-12 | Standard Oil Co | Alkylenemonothiolcarbonate preparation |
| US3324148A (en) * | 1963-06-05 | 1967-06-06 | Union Carbide Corp | Organic azidoformates and methods of preparing same |
| US3382094A (en) * | 1964-05-19 | 1968-05-07 | Thiokol Chemical Corp | Fluid and mold resistant cellulosic materials and process therefor |
| US3403166A (en) * | 1964-08-01 | 1968-09-24 | Dunlop Co Ltd | Episulfide production |
| US3372089A (en) * | 1966-08-15 | 1968-03-05 | Allied Chem | Combating staphylococcus aureus with 3-thietanol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2225573A (en) | Insecticide, fungicide, and the like | |
| US2302388A (en) | Insecticidal composition containing an amine having one alkoxyalkylene group | |
| US3679733A (en) | N-substituted arylcarbamoyl sulfides | |
| US2420928A (en) | Dialkoxyaryl trichloromethyl methane compounds as insecticides | |
| US2352078A (en) | Insecticidal composition | |
| HU184676B (en) | Pesticide preparation containing organic phosphorus compound and pyretroide derivative | |
| US3652770A (en) | Combatting phytopathogenic fungi on plants with sub-phytotoxic fungicidally effective amounts of herbicidal oximes of 3 5-dihalosalicylaldehyde | |
| US2651579A (en) | Halogenated thiophene pesticide | |
| US3105000A (en) | Organo-tin and organo-sulphur parasiticides | |
| US3721741A (en) | Combatting phytopathogenic fungi on plants with sub-phytoloxic fungicidally effective amounts of herbicidal n-phenyl derivatives of 3,5-dihalo-salicylaldehyde | |
| US3446843A (en) | Beta-dialkylaminoalkyl ethers and thioethers | |
| US2588997A (en) | 2, 3, 4, 4, 5, 5-hexachloro-2-cyclopentenone insecticidal compositions | |
| US3266982A (en) | Process for controlling pests | |
| US3803159A (en) | Fluorine containing cyanopyridines | |
| US3097998A (en) | Haloacrylate pesticides | |
| US3116335A (en) | Organic sulfur-containing compounds | |
| US3723534A (en) | Aryl methyl phenacyl sulfonium tetrafluoroborates | |
| US2267587A (en) | Insecticide | |
| US3849571A (en) | Insecticidal compositions containing certain terpene ethers and pyrethrinoids | |
| US3051614A (en) | Heavy oil for tree spray | |
| US3064025A (en) | Alkyl thioether and dithioether-heavy metal cyanide addition compounds | |
| US3228954A (en) | Certain 3-(substituted allyl)-rhodanines | |
| US3715436A (en) | Formimido-esters and pesticidal preparations containing them | |
| US3375157A (en) | Controlling and eradicating agricultural nematodes with halogenated phenyl propynyl ethers | |
| US3287211A (en) | Controlling mites with certain alkyl-(2, 4-dinitrophenyl) carbonates |