CS199504B2 - Manufacturing method of 2-diacoxyphosphinylimino-1,3-dithiethans - Google Patents

Manufacturing method of 2-diacoxyphosphinylimino-1,3-dithiethans Download PDF

Info

Publication number: CS199504B2
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; reaction; alkyl group; salt; sodium
Prior art date: 1976-06-14

Application number

CS773840A

Other languages

Czech (cs)

English (en)

Inventor

David W Reger

Murray Garber

Don W Long

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-14

Filing date

1977-06-10

Publication date

1980-07-31

1977-06-10 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1979-03-06 Priority to CS791496A priority Critical patent/CS199505B2/cs

1980-07-31 Publication of CS199504B2 publication Critical patent/CS199504B2/cs

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
-1 methylene halide Chemical class 0.000 claims abstract description 6
239000012736 aqueous medium Substances 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 23
238000000034 method Methods 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 14
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 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
239000011734 sodium Substances 0.000 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
230000007704 transition Effects 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052700 potassium Inorganic materials 0.000 claims description 10
239000011591 potassium Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 8
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 5
NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 5
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
DLFKJPZBBCZWOO-UHFFFAOYSA-N 8-methyl-n,n-bis(8-methylnonyl)nonan-1-amine Chemical compound CC(C)CCCCCCCN(CCCCCCCC(C)C)CCCCCCCC(C)C DLFKJPZBBCZWOO-UHFFFAOYSA-N 0.000 claims description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
ZVKAMDSUUSMZES-NZQWGLPYSA-N OS II Natural products CC(=O)N[C@H]1[C@H](OC[C@@H](O)[C@@H](O)[C@@H](O)CO)O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O ZVKAMDSUUSMZES-NZQWGLPYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
RHJOIOVESMTJEK-UHFFFAOYSA-N Fosthietan Chemical compound CCOP(=O)(OCC)N=C1SCS1 RHJOIOVESMTJEK-UHFFFAOYSA-N 0.000 abstract description 12
YEQWRWPFBFBEKU-UHFFFAOYSA-N diethoxyphosphorylcarbamodithioic acid Chemical compound CCOP(=O)(NC(S)=S)OCC YEQWRWPFBFBEKU-UHFFFAOYSA-N 0.000 abstract description 2
239000003444 phase transfer catalyst Substances 0.000 abstract description 2
UPNNXUSUOSTIIM-UHFFFAOYSA-N 1,2-dithietane Chemical compound C1CSS1 UPNNXUSUOSTIIM-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000012074 organic phase Substances 0.000 description 15
239000012071 phase Substances 0.000 description 10
239000002689 soil Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000227653 Lycopersicon Species 0.000 description 6
241000244206 Nematoda Species 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
239000003849 aromatic solvent Substances 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 4
239000012990 dithiocarbamate Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VZPJECPLMDDSRB-UHFFFAOYSA-N 1-[ethoxy(isothiocyanato)phosphoryl]oxyethane Chemical compound CCOP(=O)(OCC)N=C=S VZPJECPLMDDSRB-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
XFUKEWWTUCXNCS-UHFFFAOYSA-N azanium;n-diethoxyphosphorylcarbamodithioate Chemical compound [NH4+].CCOP(=O)(NC([S-])=S)OCC XFUKEWWTUCXNCS-UHFFFAOYSA-N 0.000 description 3
239000012455 biphasic mixture Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
HLNJFEXZDGURGZ-UHFFFAOYSA-M 1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1 HLNJFEXZDGURGZ-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000243786 Meloidogyne incognita Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
235000002262 Lycopersicon Nutrition 0.000 description 1
241001143352 Meloidogyne Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
WVJHTDYCHXXKHZ-UHFFFAOYSA-N n-dimethoxyphosphoryl-1,3-dithietan-2-imine Chemical compound COP(=O)(OC)N=C1SCS1 WVJHTDYCHXXKHZ-UHFFFAOYSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
ITNAGXHTIOJJQY-UHFFFAOYSA-M sodium;n-diethoxyphosphorylcarbamodithioate Chemical compound [Na+].CCOP(=O)(NC([S-])=S)OCC ITNAGXHTIOJJQY-UHFFFAOYSA-M 0.000 description 1
WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
230000004580 weight loss Effects 0.000 description 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655327—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a four-membered ring

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS773840A 1976-06-14 1977-06-10 Manufacturing method of 2-diacoxyphosphinylimino-1,3-dithiethans CS199504B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS791496A CS199505B2 (cs)	1976-06-14	1979-03-06	Způsob výroby 2-dialkoxyío8řiuýlimino-l,3-dithietanů

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/695,691 US4067882A (en)	1976-06-14	1976-06-14	Process for the preparation of 2-dialkoxy phosphinylimino-1,3-dithietane

Publications (1)

Publication Number	Publication Date
CS199504B2 true CS199504B2 (en)	1980-07-31

Family

ID=24794091

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS773840A CS199504B2 (en)	1976-06-14	1977-06-10	Manufacturing method of 2-diacoxyphosphinylimino-1,3-dithiethans

Country Status (17)

Country	Link
US (1)	US4067882A (de)
JP (1)	JPS52153999A (de)
AR (1)	AR224720A1 (de)
AU (1)	AU506843B2 (de)
BR (1)	BR7703852A (de)
CA (1)	CA1080722A (de)
CH (1)	CH633295A5 (de)
CS (1)	CS199504B2 (de)
DD (1)	DD132345A5 (de)
DE (1)	DE2726129A1 (de)
DK (1)	DK146070C (de)
FR (1)	FR2355025A1 (de)
GB (1)	GB1564639A (de)
IL (1)	IL52159A (de)
IT (1)	IT1078493B (de)
NL (1)	NL7706547A (de)
YU (1)	YU147077A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4070372A (en) *	1976-06-14	1978-01-24	American Cyanamid Company	Process for the preparation of the 2-diethoxyphosphinylimino-1,3-dithietane

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES351113A1 (es) *	1967-03-01	1969-12-16	American Cyanamid Co	Procedimiento para preparar 2-imino-1,3-ditioetanos.
US3470207A (en) *	1967-04-21	1969-09-30	American Cyanamid Co	Imino-1,3-dithietanes and their preparation

1976
- 1976-06-14 US US05/695,691 patent/US4067882A/en not_active Expired - Lifetime
1977
- 1977-05-19 GB GB21219/77A patent/GB1564639A/en not_active Expired
- 1977-05-23 AU AU25384/77A patent/AU506843B2/en not_active Expired
- 1977-05-25 IL IL52159A patent/IL52159A/xx unknown
- 1977-05-31 AR AR267864A patent/AR224720A1/es active
- 1977-06-09 CA CA280,157A patent/CA1080722A/en not_active Expired
- 1977-06-10 CS CS773840A patent/CS199504B2/cs unknown
- 1977-06-10 DE DE19772726129 patent/DE2726129A1/de not_active Withdrawn
- 1977-06-13 CH CH724277A patent/CH633295A5/de not_active IP Right Cessation
- 1977-06-13 IT IT49795/77A patent/IT1078493B/it active
- 1977-06-13 YU YU01470/77A patent/YU147077A/xx unknown
- 1977-06-13 DK DK260777A patent/DK146070C/da not_active IP Right Cessation
- 1977-06-14 NL NL7706547A patent/NL7706547A/xx not_active Application Discontinuation
- 1977-06-14 DD DD7700199488A patent/DD132345A5/de unknown
- 1977-06-14 JP JP6954377A patent/JPS52153999A/ja active Pending
- 1977-06-14 FR FR7718213A patent/FR2355025A1/fr active Granted
- 1977-06-14 BR BR7703852A patent/BR7703852A/pt unknown

Also Published As

Publication number	Publication date
FR2355025B1 (de)	1982-04-02
DK146070C (da)	1983-11-14
NL7706547A (nl)	1977-12-16
DD132345A5 (de)	1978-09-20
IT1078493B (it)	1985-05-08
DE2726129A1 (de)	1977-12-22
CH633295A5 (de)	1982-11-30
US4067882A (en)	1978-01-10
YU147077A (en)	1982-10-31
FR2355025A1 (fr)	1978-01-13
CA1080722A (en)	1980-07-01
AR224720A1 (es)	1982-01-15
BR7703852A (pt)	1978-04-25
IL52159A0 (en)	1977-07-31
JPS52153999A (en)	1977-12-21
AU506843B2 (en)	1980-01-24
IL52159A (en)	1980-12-31
GB1564639A (en)	1980-04-10
DK260777A (da)	1977-12-15
AU2538477A (en)	1978-11-30
DK146070B (da)	1983-06-20

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US4147715A (en)	1979-04-03	Thiocarbamate preparation utilizing quaternary ammonium salt catalysts
CS199504B2 (en)	1980-07-31	Manufacturing method of 2-diacoxyphosphinylimino-1,3-dithiethans
KR840000891B1 (ko)	1984-06-26	비대칭 티오포스포네이트 화합물의 제조방법
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CS199505B2 (cs)	1980-07-31	Způsob výroby 2-dialkoxyío8řiuýlimino-l,3-dithietanů
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